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Showing metabocard for Citicoline (HMDB0001413)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (7) Show 7 proteinsXML
enzymes (7) Show 7 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2021-09-14 14:59:39 UTC
HMDB IDHMDB0001413
Secondary Accession Numbers
  • HMDB01413
Metabolite Identification
Common NameCiticoline
DescriptionCiticoline is an essential intermediate in the biosynthetic pathway of structural phospholipids in cell membranes, particularly phosphatidylcholine. Once absorbed, citicoline is widely distributed throughout the body, crosses the blood-brain barrier and reaches the central nervous system (CNS), where it is incorporated into the membrane and microsomal phospholipid fraction. Citicoline activates biosynthesis of structural phospholipids of neuronal membranes, increases brain metabolism, and acts upon the levels of different neurotransmitters. Thus, citicoline has been experimentally shown to increase norepinephrine and dopamine levels in the CNS. Owing to these pharmacological mechanisms, citicoline has a neuroprotective effect in hypoxic and ischemic conditions, decreasing the volume of ischemic lesion, and also improves learning and memory performance in animal models of brain aging. In addition, citicoline has been shown to restore the activity of mitochondrial ATPase and membrane Na+/K+ATPase, to inhibit activation of certain phospholipases, and to accelerate reabsorption of cerebral edema in various experimental models. Citicoline has also been shown to be able to inhibit mechanisms of apoptosis associated to cerebral ischemia and in certain neurodegeneration models, and to potentiate neuroplasticity mechanisms. Citicoline is a safe drug, as shown by the toxicological tests conducted, that has no significant systemic cholinergic effects and is a well tolerated product. (PMID:17171187 ).
Structure
Data?1600457051
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0001413 (Citicoline)


  Mrv1652309182018092D          

 31 32  0  0  0  0            999 V2000
10001.6951 9996.3152    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10000.9729 9996.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1056 9995.6001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2803 9995.6001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.2570 9996.3030    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10000.6717 9995.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8465 9995.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4089 9996.7289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1222 9996.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.8377 9996.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5510 9996.3159    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10005.2644 9996.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5510 9995.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2644 9995.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5770 9998.1618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3650 9998.1536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8315 9996.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3558 9997.5392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5453 9996.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9260 9995.0659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0690 9996.3035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3545 9996.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6400 9996.3034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6399 9995.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3544 9995.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0690 9995.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4531 9996.2204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7857 9996.7054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.0406 9997.4900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8656 9997.4900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.1205 9996.7054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
  8  1  1  0  0  0  0
 17 19  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 21 22  1  0  0  0  0
 26 21  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 28  1  0  0  0  0
 27 31  1  0  0  0  0
 22 18  2  0  0  0  0
 24 20  1  0  0  0  0
 29 15  1  6  0  0  0
 28 21  1  1  0  0  0
 30 16  1  6  0  0  0
 31 17  1  1  0  0  0
  5 19  1  0  0  0  0
M  CHG  1  11   1
M  END
Download

3D MOL for HMDB0001413 (Citicoline)

HMDB0001413
     RDKit          3D
Citicoline
 58 59  0  0  0  0  0  0  0  0999 V2000
    6.5876   -0.9333   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6614    0.3734   -0.3822 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.9241    1.3173   -1.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8451    0.4499    0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4689    0.7951    0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3945   -0.2692    0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0211   -0.6464   -0.9596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8346   -1.8222   -0.9655 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.4075   -2.0381   -2.4084 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4489   -3.3277   -0.4351 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5294   -1.4415    0.0098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4861   -0.3237   -0.7107 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.3030    0.9263   -1.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454   -0.8884   -2.1664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7141    0.1012    0.3837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8071   -0.7296    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8216   -0.2771    1.3464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2932    1.0019    1.1596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6089    1.0641    1.5283 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4489    1.2827    0.3442 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7973    1.2258    0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5995    1.4289   -0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0484    1.6973   -1.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8445    1.9108   -3.0542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6970    1.7486   -1.9650 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9351    1.5450   -0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620    1.5988   -0.9509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0190   -0.2769    2.0973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7254   -0.2427    3.4589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0443   -1.1860    1.3764 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8136   -2.3622    2.0444 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1331   -1.6966   -0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1380   -0.8983   -1.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6505   -1.2699   -1.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4963    0.9243   -2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0243    1.4603   -1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4802    2.3077   -1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6346    1.0054    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1594   -0.5846    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7160    0.8773   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0198    1.7164   -0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6981    1.0657    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6663   -1.1179    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4992    0.2085    0.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5479   -3.2272    0.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0749   -1.8391   -2.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859   -0.7642   -0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5466   -1.7793    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3426   -0.3855    2.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8242    1.8854    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2736    1.0178    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6633    1.3799   -0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9516    1.1440   -3.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3270    2.8094   -3.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0667   -0.5406    1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762   -0.9848    3.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3678   -1.3071    0.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0000   -3.1089    1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 19 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 17  1  0
 26 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
 10 45  1  0
 14 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  1
 19 50  1  1
 21 51  1  0
 22 52  1  0
 24 53  1  0
 24 54  1  0
 28 55  1  1
 29 56  1  0
 30 57  1  6
 31 58  1  0
M  CHG  1   2   1
M  END
Download

3D SDF for HMDB0001413 (Citicoline)


  Mrv1652309182018092D          

 31 32  0  0  0  0            999 V2000
10001.6951 9996.3152    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10000.9729 9996.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.1056 9995.6001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2803 9995.6001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.2570 9996.3030    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
10000.6717 9995.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8465 9995.5878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.4089 9996.7289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1222 9996.3159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.8377 9996.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5510 9996.3159    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
10005.2644 9996.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.5510 9995.3401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.2644 9995.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.5770 9998.1618    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.3650 9998.1536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8315 9996.3036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3558 9997.5392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5453 9996.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9993.9260 9995.0659    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0690 9996.3035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3545 9996.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6400 9996.3034    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9994.6399 9995.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.3544 9995.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0690 9995.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4531 9996.2204    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7857 9996.7054    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.0406 9997.4900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8656 9997.4900    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.1205 9996.7054    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
  8  1  1  0  0  0  0
 17 19  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 21 22  1  0  0  0  0
 26 21  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 28  1  0  0  0  0
 27 31  1  0  0  0  0
 22 18  2  0  0  0  0
 24 20  1  0  0  0  0
 29 15  1  6  0  0  0
 28 21  1  1  0  0  0
 30 16  1  6  0  0  0
 31 17  1  1  0  0  0
  5 19  1  0  0  0  0
M  CHG  1  11   1
M  END
> <DATABASE_ID>
HMDB0001413

> <DATABASE_NAME>
hmdb

> <SMILES>
C[N+](C)(C)CCOP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/p+1/t9-,11-,12-,13-/m1/s1

> <INCHI_KEY>
RZZPDXZPRHQOCG-OJAKKHQRSA-O

> <FORMULA>
C14H27N4O11P2

> <MOLECULAR_WEIGHT>
489.3319

> <EXACT_MASS>
489.11515575

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
42.66540842325586

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[2-(trimethylazaniumyl)ethoxy]phosphoryl}oxy)phosphinic acid

> <ALOGPS_LOGP>
-1.12

> <JCHEM_LOGP>
-7.108613166138413

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.2590685279371496

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.849943564850884

> <JCHEM_PKA_STRONGEST_BASIC>
-0.03216635969834636

> <JCHEM_POLAR_SURFACE_AREA>
210.67

> <JCHEM_REFRACTIVITY>
114.70559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cdp-choline(1+)

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0001413 (Citicoline)

HMDB0001413
     RDKit          3D
Citicoline
 58 59  0  0  0  0  0  0  0  0999 V2000
    6.5876   -0.9333   -0.9666 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6614    0.3734   -0.3822 N   0  0  0  0  0  4  0  0  0  0  0  0
    6.9241    1.3173   -1.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8451    0.4499    0.4838 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4689    0.7951    0.2859 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3945   -0.2692    0.3306 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0211   -0.6464   -0.9596 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8346   -1.8222   -0.9655 P   0  0  0  0  0  5  0  0  0  0  0  0
    2.4075   -2.0381   -2.4084 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4489   -3.3277   -0.4351 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5294   -1.4415    0.0098 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4861   -0.3237   -0.7107 P   0  0  0  0  0  5  0  0  0  0  0  0
    1.3030    0.9263   -1.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1454   -0.8884   -2.1664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7141    0.1012    0.3837 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8071   -0.7296    0.3418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8216   -0.2771    1.3464 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2932    1.0019    1.1596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6089    1.0641    1.5283 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.4489    1.2827    0.3442 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7973    1.2258    0.4357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5995    1.4289   -0.6670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0484    1.6973   -1.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8445    1.9108   -3.0542 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6970    1.7486   -1.9650 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9351    1.5450   -0.8650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6620    1.5988   -0.9509 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0190   -0.2769    2.0973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7254   -0.2427    3.4589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0443   -1.1860    1.3764 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8136   -2.3622    2.0444 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1331   -1.6966   -0.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1380   -0.8983   -1.9839 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6505   -1.2699   -1.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4963    0.9243   -2.4306 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0243    1.4603   -1.6080 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4802    2.3077   -1.2433 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6346    1.0054    1.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1594   -0.5846    0.7874 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7160    0.8773   -0.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0198    1.7164   -0.1566 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6981    1.0657    1.3487 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6663   -1.1179    0.9715 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4992    0.2085    0.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5479   -3.2272    0.5649 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0749   -1.8391   -2.3197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859   -0.7642   -0.6628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5466   -1.7793    0.5866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3426   -0.3855    2.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8242    1.8854    2.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2736    1.0178    1.3893 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6633    1.3799   -0.5745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9516    1.1440   -3.7431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3270    2.8094   -3.2372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0667   -0.5406    1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1762   -0.9848    3.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3678   -1.3071    0.3299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0000   -3.1089    1.3971 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 19 28  1  0
 28 29  1  0
 28 30  1  0
 30 31  1  0
 30 17  1  0
 26 20  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  3 35  1  0
  3 36  1  0
  3 37  1  0
  4 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
 10 45  1  0
 14 46  1  0
 16 47  1  0
 16 48  1  0
 17 49  1  1
 19 50  1  1
 21 51  1  0
 22 52  1  0
 24 53  1  0
 24 54  1  0
 28 55  1  1
 29 56  1  0
 30 57  1  6
 31 58  1  0
M  CHG  1   2   1
M  END
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PDB for HMDB0001413 (Citicoline)

HEADER    PROTEIN                                 18-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-SEP-20         0                                  
HETATM    1  P   UNK     0    8669.8318659.788   0.000  0.00  0.00           P+0
HETATM    2  O   UNK     0    8668.4838660.534   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8670.5978658.454   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8669.0578658.454   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0    8667.1468659.766   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0    8667.9218658.431   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8666.3808658.431   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8671.1638660.561   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8672.4958659.790   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8673.8308660.561   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0    8675.1628659.790   0.000  0.00  0.00           N+1
HETATM   12  C   UNK     0    8676.4948660.561   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8675.1628657.968   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8676.4948659.022   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0    8660.2778663.235   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0    8663.6158663.220   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0    8664.4858659.767   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0    8657.9978662.073   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    8665.8188660.534   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0    8655.3298657.456   0.000  0.00  0.00           N+0
HETATM   21  N   UNK     0    8659.3298659.767   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0    8657.9958660.536   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0    8656.6618659.766   0.000  0.00  0.00           N+0
HETATM   24  C   UNK     0    8656.6618658.226   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8657.9958657.456   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8659.3298658.227   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0    8661.9128659.611   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0    8660.6678660.517   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8661.1428661.981   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8662.6828661.981   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8663.1588660.517   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    8                                             
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4    1                                                            
CONECT    5    2    6    7   19                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    9    1                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11                                                            
CONECT   15   29                                                            
CONECT   16   30                                                            
CONECT   17   19   31                                                       
CONECT   18   22                                                            
CONECT   19   17    5                                                       
CONECT   20   24                                                            
CONECT   21   22   26   28                                                  
CONECT   22   23   21   18                                                  
CONECT   23   22   24                                                       
CONECT   24   25   23   20                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21                                                       
CONECT   27   28   31                                                       
CONECT   28   29   27   21                                                  
CONECT   29   28   30   15                                                  
CONECT   30   29   31   16                                                  
CONECT   31   30   27   17                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   64    0
END
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3D PDB for HMDB0001413 (Citicoline)

COMPND    HMDB0001413
HETATM    1  C1  UNL     1       6.588  -0.933  -0.967  1.00  0.00           C  
HETATM    2  N1  UNL     1       6.661   0.373  -0.382  1.00  0.00           N1+
HETATM    3  C2  UNL     1       6.924   1.317  -1.477  1.00  0.00           C  
HETATM    4  C3  UNL     1       7.845   0.450   0.484  1.00  0.00           C  
HETATM    5  C4  UNL     1       5.469   0.795   0.286  1.00  0.00           C  
HETATM    6  C5  UNL     1       4.395  -0.269   0.331  1.00  0.00           C  
HETATM    7  O1  UNL     1       4.021  -0.646  -0.960  1.00  0.00           O  
HETATM    8  P1  UNL     1       2.835  -1.822  -0.965  1.00  0.00           P  
HETATM    9  O2  UNL     1       2.407  -2.038  -2.408  1.00  0.00           O  
HETATM   10  O3  UNL     1       3.449  -3.328  -0.435  1.00  0.00           O  
HETATM   11  O4  UNL     1       1.529  -1.442   0.010  1.00  0.00           O  
HETATM   12  P2  UNL     1       0.486  -0.324  -0.711  1.00  0.00           P  
HETATM   13  O5  UNL     1       1.303   0.926  -1.025  1.00  0.00           O  
HETATM   14  O6  UNL     1      -0.145  -0.888  -2.166  1.00  0.00           O  
HETATM   15  O7  UNL     1      -0.714   0.101   0.384  1.00  0.00           O  
HETATM   16  C6  UNL     1      -1.807  -0.730   0.342  1.00  0.00           C  
HETATM   17  C7  UNL     1      -2.822  -0.277   1.346  1.00  0.00           C  
HETATM   18  O8  UNL     1      -3.293   1.002   1.160  1.00  0.00           O  
HETATM   19  C8  UNL     1      -4.609   1.064   1.528  1.00  0.00           C  
HETATM   20  N2  UNL     1      -5.449   1.283   0.344  1.00  0.00           N  
HETATM   21  C9  UNL     1      -6.797   1.226   0.436  1.00  0.00           C  
HETATM   22  C10 UNL     1      -7.599   1.429  -0.667  1.00  0.00           C  
HETATM   23  C11 UNL     1      -7.048   1.697  -1.901  1.00  0.00           C  
HETATM   24  N3  UNL     1      -7.844   1.911  -3.054  1.00  0.00           N  
HETATM   25  N4  UNL     1      -5.697   1.749  -1.965  1.00  0.00           N  
HETATM   26  C12 UNL     1      -4.935   1.545  -0.865  1.00  0.00           C  
HETATM   27  O9  UNL     1      -3.662   1.599  -0.951  1.00  0.00           O  
HETATM   28  C13 UNL     1      -5.019  -0.277   2.097  1.00  0.00           C  
HETATM   29  O10 UNL     1      -4.725  -0.243   3.459  1.00  0.00           O  
HETATM   30  C14 UNL     1      -4.044  -1.186   1.376  1.00  0.00           C  
HETATM   31  O11 UNL     1      -3.814  -2.362   2.044  1.00  0.00           O  
HETATM   32  H1  UNL     1       6.133  -1.697  -0.323  1.00  0.00           H  
HETATM   33  H2  UNL     1       6.138  -0.898  -1.984  1.00  0.00           H  
HETATM   34  H3  UNL     1       7.651  -1.270  -1.138  1.00  0.00           H  
HETATM   35  H4  UNL     1       6.496   0.924  -2.431  1.00  0.00           H  
HETATM   36  H5  UNL     1       8.024   1.460  -1.608  1.00  0.00           H  
HETATM   37  H6  UNL     1       6.480   2.308  -1.243  1.00  0.00           H  
HETATM   38  H7  UNL     1       7.635   1.005   1.404  1.00  0.00           H  
HETATM   39  H8  UNL     1       8.159  -0.585   0.787  1.00  0.00           H  
HETATM   40  H9  UNL     1       8.716   0.877  -0.057  1.00  0.00           H  
HETATM   41  H10 UNL     1       5.020   1.716  -0.157  1.00  0.00           H  
HETATM   42  H11 UNL     1       5.698   1.066   1.349  1.00  0.00           H  
HETATM   43  H12 UNL     1       4.666  -1.118   0.972  1.00  0.00           H  
HETATM   44  H13 UNL     1       3.499   0.209   0.790  1.00  0.00           H  
HETATM   45  H14 UNL     1       3.548  -3.227   0.565  1.00  0.00           H  
HETATM   46  H15 UNL     1       0.075  -1.839  -2.320  1.00  0.00           H  
HETATM   47  H16 UNL     1      -2.286  -0.764  -0.663  1.00  0.00           H  
HETATM   48  H17 UNL     1      -1.547  -1.779   0.587  1.00  0.00           H  
HETATM   49  H18 UNL     1      -2.343  -0.386   2.359  1.00  0.00           H  
HETATM   50  H19 UNL     1      -4.824   1.885   2.253  1.00  0.00           H  
HETATM   51  H20 UNL     1      -7.274   1.018   1.389  1.00  0.00           H  
HETATM   52  H21 UNL     1      -8.663   1.380  -0.575  1.00  0.00           H  
HETATM   53  H22 UNL     1      -7.952   1.144  -3.743  1.00  0.00           H  
HETATM   54  H23 UNL     1      -8.327   2.809  -3.237  1.00  0.00           H  
HETATM   55  H24 UNL     1      -6.067  -0.541   1.896  1.00  0.00           H  
HETATM   56  H25 UNL     1      -4.176  -0.985   3.766  1.00  0.00           H  
HETATM   57  H26 UNL     1      -4.368  -1.307   0.330  1.00  0.00           H  
HETATM   58  H27 UNL     1      -4.000  -3.109   1.397  1.00  0.00           H  
CONECT    1    2   32   33   34
CONECT    2    3    4    5
CONECT    3   35   36   37
CONECT    4   38   39   40
CONECT    5    6   41   42
CONECT    6    7   43   44
CONECT    7    8
CONECT    8    9    9   10   11
CONECT   10   45
CONECT   11   12
CONECT   12   13   13   14   15
CONECT   14   46
CONECT   15   16
CONECT   16   17   47   48
CONECT   17   18   30   49
CONECT   18   19
CONECT   19   20   28   50
CONECT   20   21   26
CONECT   21   22   22   51
CONECT   22   23   52
CONECT   23   24   25   25
CONECT   24   53   54
CONECT   25   26
CONECT   26   27   27
CONECT   28   29   30   55
CONECT   29   56
CONECT   30   31   57
CONECT   31   58
END
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SMILES for HMDB0001413 (Citicoline)

C[N+](C)(C)CCOP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O
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INCHI for HMDB0001413 (Citicoline)

InChI=1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/p+1/t9-,11-,12-,13-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
Cytidine 5'-(trihydrogen diphosphate), mono(2-(trimethylammonio)ethyl) esterChEBI
Cytidine 5'-(trihydrogen diphosphoric acid), mono(2-(trimethylammonio)ethyl) esterGenerator
CidifosMeSH
Diphosphate choline, cytidineMeSH
5'-Diphosphocholine, cytidineMeSH
Choline, cytidine diphosphateMeSH
CiticholineMeSH
Choline, CDPMeSH
CiticolineMeSH
CyticholineMeSH
Cytidine 5'-diphosphocholineMeSH
Cytidine diphosphate cholineMeSH
CDP CholineMeSH
Cytidine 5' diphosphocholineMeSH
CDP-cholineHMDB
Choline 5'-cytidine diphosphateHMDB
Choline 5’-cytidine diphosphateHMDB
Choline cytidine diphosphateHMDB
Cytidine 5'-(choline diphosphate)HMDB
Cytidine 5'-(cholinyl pyrophosphate)HMDB
Cytidine 5'-diphosphate cholineHMDB
Cytidine 5’-(choline diphosphate)HMDB
Cytidine 5’-(cholinyl pyrophosphate)HMDB
Cytidine 5’-diphosphate cholineHMDB
Cytidine 5’-diphosphocholineHMDB
Cytidine choline diphosphateHMDB
Cytidine diphosphate choline esterHMDB
Cytidine diphosphocholineHMDB
Cytidine diphosphorylcholineHMDB
Chemical FormulaC14H27N4O11P2
Average Molecular Weight489.3319
Monoisotopic Molecular Weight489.11515575
IUPAC Name{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({hydroxy[2-(trimethylazaniumyl)ethoxy]phosphoryl}oxy)phosphinic acid
Traditional Namecdp-choline(1+)
CAS Registry Number987-78-0
SMILES
C[N+](C)(C)CCOP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O
InChI Identifier
InChI=1S/C14H26N4O11P2/c1-18(2,3)6-7-26-30(22,23)29-31(24,25)27-8-9-11(19)12(20)13(28-9)17-5-4-10(15)16-14(17)21/h4-5,9,11-13,19-20H,6-8H2,1-3H3,(H3-,15,16,21,22,23,24,25)/p+1/t9-,11-,12-,13-/m1/s1
InChI KeyRZZPDXZPRHQOCG-OJAKKHQRSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pterins and derivatives. These are polycyclic aromatic compounds containing a pterin moiety, which consist of a pteridine ring bearing a ketone and an amine group to form 2-aminopteridin-4(3H)-one.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPteridines and derivatives
Sub ClassPterins and derivatives
Direct ParentPterins and derivatives
Alternative Parents
Substituents
  • Pterin
  • Aminobenzoic acid
  • Aminobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzoic acid
  • Benzoyl
  • Aniline or substituted anilines
  • Phenylalkylamine
  • Hydroxypyrimidine
  • Secondary aliphatic/aromatic amine
  • Monocyclic benzene moiety
  • Pyrimidine
  • Benzenoid
  • Heteroaromatic compound
  • Amino acid or derivatives
  • Amino acid
  • Ketimine
  • Azacycle
  • Secondary amine
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Imine
  • Organonitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available205.2http://allccs.zhulab.cn/database/detail?ID=AllCCS00000123
[M+H]+Not Available198.7http://allccs.zhulab.cn/database/detail?ID=AllCCS00000123
Predicted Molecular Properties
PropertyValueSource
Water Solubility7.99 g/LALOGPS
logP-1.1ALOGPS
logP-7.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)1.85ChemAxon
pKa (Strongest Basic)-0.032ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area210.67 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity114.71 m³·mol⁻¹ChemAxon
Polarizability42.67 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+180.26130932474
DeepCCS[M-H]-178.17930932474
DeepCCS[M-2H]-211.41730932474
DeepCCS[M+Na]+186.16930932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.42 minutes32390414
Predicted by Siyang on May 30, 20229.4965 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20229.04 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid548.6 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid388.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid235.0 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid69.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid182.7 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid52.9 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid284.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid300.1 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)1066.0 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid569.9 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid52.7 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid594.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid210.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid319.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate978.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA594.2 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water467.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CiticolineC[N+](C)(C)CCOP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O4193.4Standard polar33892256
CiticolineC[N+](C)(C)CCOP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O2744.9Standard non polar33892256
CiticolineC[N+](C)(C)CCOP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O3931.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citicoline,1TMS,isomer #1C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O3566.2Semi standard non polar33892256
Citicoline,1TMS,isomer #2C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C3570.2Semi standard non polar33892256
Citicoline,1TMS,isomer #3C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O3616.6Semi standard non polar33892256
Citicoline,1TMS,isomer #4C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C3613.0Semi standard non polar33892256
Citicoline,1TMS,isomer #5C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O3661.5Semi standard non polar33892256
Citicoline,2TMS,isomer #1C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3476.0Semi standard non polar33892256
Citicoline,2TMS,isomer #10C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C3627.4Semi standard non polar33892256
Citicoline,2TMS,isomer #11C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O3585.0Semi standard non polar33892256
Citicoline,2TMS,isomer #2C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O3506.3Semi standard non polar33892256
Citicoline,2TMS,isomer #3C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3506.4Semi standard non polar33892256
Citicoline,2TMS,isomer #4C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O3573.2Semi standard non polar33892256
Citicoline,2TMS,isomer #5C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C3515.4Semi standard non polar33892256
Citicoline,2TMS,isomer #6C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3516.6Semi standard non polar33892256
Citicoline,2TMS,isomer #7C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C3573.5Semi standard non polar33892256
Citicoline,2TMS,isomer #8C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C3541.8Semi standard non polar33892256
Citicoline,2TMS,isomer #9C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O3626.3Semi standard non polar33892256
Citicoline,3TMS,isomer #1C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3440.4Semi standard non polar33892256
Citicoline,3TMS,isomer #1C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3319.1Standard non polar33892256
Citicoline,3TMS,isomer #1C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C5262.7Standard polar33892256
Citicoline,3TMS,isomer #10C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3556.1Semi standard non polar33892256
Citicoline,3TMS,isomer #10C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3401.3Standard non polar33892256
Citicoline,3TMS,isomer #10C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C4953.8Standard polar33892256
Citicoline,3TMS,isomer #11C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C3496.9Semi standard non polar33892256
Citicoline,3TMS,isomer #11C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C3428.1Standard non polar33892256
Citicoline,3TMS,isomer #11C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C5133.5Standard polar33892256
Citicoline,3TMS,isomer #12C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C3587.4Semi standard non polar33892256
Citicoline,3TMS,isomer #12C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C3457.1Standard non polar33892256
Citicoline,3TMS,isomer #12C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C4756.1Standard polar33892256
Citicoline,3TMS,isomer #13C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O3546.0Semi standard non polar33892256
Citicoline,3TMS,isomer #13C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O3467.5Standard non polar33892256
Citicoline,3TMS,isomer #13C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O4920.0Standard polar33892256
Citicoline,3TMS,isomer #14C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C3548.2Semi standard non polar33892256
Citicoline,3TMS,isomer #14C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C3462.7Standard non polar33892256
Citicoline,3TMS,isomer #14C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C4923.4Standard polar33892256
Citicoline,3TMS,isomer #2C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3442.8Semi standard non polar33892256
Citicoline,3TMS,isomer #2C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3313.9Standard non polar33892256
Citicoline,3TMS,isomer #2C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C5267.3Standard polar33892256
Citicoline,3TMS,isomer #3C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3515.4Semi standard non polar33892256
Citicoline,3TMS,isomer #3C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3398.2Standard non polar33892256
Citicoline,3TMS,isomer #3C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C5232.6Standard polar33892256
Citicoline,3TMS,isomer #4C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3452.2Semi standard non polar33892256
Citicoline,3TMS,isomer #4C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3360.2Standard non polar33892256
Citicoline,3TMS,isomer #4C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C5046.5Standard polar33892256
Citicoline,3TMS,isomer #5C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O3552.6Semi standard non polar33892256
Citicoline,3TMS,isomer #5C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O3429.7Standard non polar33892256
Citicoline,3TMS,isomer #5C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O4975.0Standard polar33892256
Citicoline,3TMS,isomer #6C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3556.0Semi standard non polar33892256
Citicoline,3TMS,isomer #6C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3425.1Standard non polar33892256
Citicoline,3TMS,isomer #6C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C4977.4Standard polar33892256
Citicoline,3TMS,isomer #7C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O3497.3Semi standard non polar33892256
Citicoline,3TMS,isomer #7C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O3446.2Standard non polar33892256
Citicoline,3TMS,isomer #7C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O5149.8Standard polar33892256
Citicoline,3TMS,isomer #8C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3460.5Semi standard non polar33892256
Citicoline,3TMS,isomer #8C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3337.3Standard non polar33892256
Citicoline,3TMS,isomer #8C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C5027.1Standard polar33892256
Citicoline,3TMS,isomer #9C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C3552.5Semi standard non polar33892256
Citicoline,3TMS,isomer #9C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C3408.8Standard non polar33892256
Citicoline,3TMS,isomer #9C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C4959.3Standard polar33892256
Citicoline,4TMS,isomer #1C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3408.3Semi standard non polar33892256
Citicoline,4TMS,isomer #1C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3276.1Standard non polar33892256
Citicoline,4TMS,isomer #1C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C4858.4Standard polar33892256
Citicoline,4TMS,isomer #10C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3510.6Semi standard non polar33892256
Citicoline,4TMS,isomer #10C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3375.9Standard non polar33892256
Citicoline,4TMS,isomer #10C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C4571.8Standard polar33892256
Citicoline,4TMS,isomer #11C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C3538.6Semi standard non polar33892256
Citicoline,4TMS,isomer #11C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C3422.6Standard non polar33892256
Citicoline,4TMS,isomer #11C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C4377.1Standard polar33892256
Citicoline,4TMS,isomer #2C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3504.7Semi standard non polar33892256
Citicoline,4TMS,isomer #2C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3368.1Standard non polar33892256
Citicoline,4TMS,isomer #2C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C4694.3Standard polar33892256
Citicoline,4TMS,isomer #3C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3509.8Semi standard non polar33892256
Citicoline,4TMS,isomer #3C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3361.9Standard non polar33892256
Citicoline,4TMS,isomer #3C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C4684.9Standard polar33892256
Citicoline,4TMS,isomer #4C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3469.1Semi standard non polar33892256
Citicoline,4TMS,isomer #4C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3379.8Standard non polar33892256
Citicoline,4TMS,isomer #4C[N+](C)(C)CCOP(=O)(O)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C4842.8Standard polar33892256
Citicoline,4TMS,isomer #5C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3533.7Semi standard non polar33892256
Citicoline,4TMS,isomer #5C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3392.4Standard non polar33892256
Citicoline,4TMS,isomer #5C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C4459.0Standard polar33892256
Citicoline,4TMS,isomer #6C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O3502.0Semi standard non polar33892256
Citicoline,4TMS,isomer #6C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O3401.8Standard non polar33892256
Citicoline,4TMS,isomer #6C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O4599.5Standard polar33892256
Citicoline,4TMS,isomer #7C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3507.0Semi standard non polar33892256
Citicoline,4TMS,isomer #7C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3395.4Standard non polar33892256
Citicoline,4TMS,isomer #7C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C4599.0Standard polar33892256
Citicoline,4TMS,isomer #8C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3535.9Semi standard non polar33892256
Citicoline,4TMS,isomer #8C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3365.6Standard non polar33892256
Citicoline,4TMS,isomer #8C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C4428.8Standard polar33892256
Citicoline,4TMS,isomer #9C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C3504.8Semi standard non polar33892256
Citicoline,4TMS,isomer #9C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C3382.2Standard non polar33892256
Citicoline,4TMS,isomer #9C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C4579.8Standard polar33892256
Citicoline,5TMS,isomer #1C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3504.9Semi standard non polar33892256
Citicoline,5TMS,isomer #1C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3339.4Standard non polar33892256
Citicoline,5TMS,isomer #1C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C4213.2Standard polar33892256
Citicoline,5TMS,isomer #2C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3481.3Semi standard non polar33892256
Citicoline,5TMS,isomer #2C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C3345.4Standard non polar33892256
Citicoline,5TMS,isomer #2C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C4354.7Standard polar33892256
Citicoline,5TMS,isomer #3C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3488.3Semi standard non polar33892256
Citicoline,5TMS,isomer #3C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3340.5Standard non polar33892256
Citicoline,5TMS,isomer #3C[N+](C)(C)CCOP(=O)(O)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C4342.4Standard polar33892256
Citicoline,5TMS,isomer #4C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3510.9Semi standard non polar33892256
Citicoline,5TMS,isomer #4C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C3359.7Standard non polar33892256
Citicoline,5TMS,isomer #4C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O[Si](C)(C)C)[C@@H]1O)O[Si](C)(C)C4134.3Standard polar33892256
Citicoline,5TMS,isomer #5C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3519.2Semi standard non polar33892256
Citicoline,5TMS,isomer #5C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C3340.9Standard non polar33892256
Citicoline,5TMS,isomer #5C[N+](C)(C)CCOP(=O)(O[Si](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C)[Si](C)(C)C)=NC2=O)[C@H](O)[C@@H]1O[Si](C)(C)C)O[Si](C)(C)C4103.8Standard polar33892256
Citicoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)O[C@H]1N1C=CC(N)=NC1=O3794.5Semi standard non polar33892256
Citicoline,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O3796.9Semi standard non polar33892256
Citicoline,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OP(=O)(OCC[N+](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O3827.4Semi standard non polar33892256
Citicoline,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O)OP(=O)(O)OCC[N+](C)(C)C3825.0Semi standard non polar33892256
Citicoline,1TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O)[C@H]2O)C=C13922.6Semi standard non polar33892256
Citicoline,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3907.3Semi standard non polar33892256
Citicoline,2TBDMS,isomer #10CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O)[C@H]2O)C=C14072.2Semi standard non polar33892256
Citicoline,2TBDMS,isomer #11CC(C)(C)[Si](C)(C)N(C1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O)[C@H]2O)C=C1)[Si](C)(C)C(C)(C)C3992.0Semi standard non polar33892256
Citicoline,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[N+](C)(C)C)O[C@H]1N1C=CC(N)=NC1=O3930.8Semi standard non polar33892256
Citicoline,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=CC(N)=NC1=O3933.1Semi standard non polar33892256
Citicoline,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C14038.9Semi standard non polar33892256
Citicoline,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[N+](C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O3935.2Semi standard non polar33892256
Citicoline,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O3935.6Semi standard non polar33892256
Citicoline,2TBDMS,isomer #7CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C14036.1Semi standard non polar33892256
Citicoline,2TBDMS,isomer #8CC(C)(C)[Si](C)(C)OP(=O)(OCC[N+](C)(C)C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@H](O)[C@@H]1O)O[Si](C)(C)C(C)(C)C3952.2Semi standard non polar33892256
Citicoline,2TBDMS,isomer #9CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=C14074.5Semi standard non polar33892256
Citicoline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[N+](C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C4057.2Semi standard non polar33892256
Citicoline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[N+](C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3778.8Standard non polar33892256
Citicoline,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[N+](C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C5289.5Standard polar33892256
Citicoline,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C14185.4Semi standard non polar33892256
Citicoline,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C13874.1Standard non polar33892256
Citicoline,3TBDMS,isomer #10CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C14964.8Standard polar33892256
Citicoline,3TBDMS,isomer #11CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]1O4113.3Semi standard non polar33892256
Citicoline,3TBDMS,isomer #11CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]1O3945.7Standard non polar33892256
Citicoline,3TBDMS,isomer #11CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@@H]1O5081.5Standard polar33892256
Citicoline,3TBDMS,isomer #12CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=C14200.2Semi standard non polar33892256
Citicoline,3TBDMS,isomer #12CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=C13884.8Standard non polar33892256
Citicoline,3TBDMS,isomer #12CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O)C=C14781.9Standard polar33892256
Citicoline,3TBDMS,isomer #13CC(C)(C)[Si](C)(C)OP(=O)(OCC[N+](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O4144.2Semi standard non polar33892256
Citicoline,3TBDMS,isomer #13CC(C)(C)[Si](C)(C)OP(=O)(OCC[N+](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O3947.1Standard non polar33892256
Citicoline,3TBDMS,isomer #13CC(C)(C)[Si](C)(C)OP(=O)(OCC[N+](C)(C)C)OP(=O)(O)OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O4901.5Standard polar33892256
Citicoline,3TBDMS,isomer #14CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)OP(=O)(O)OCC[N+](C)(C)C4144.1Semi standard non polar33892256
Citicoline,3TBDMS,isomer #14CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)OP(=O)(O)OCC[N+](C)(C)C3945.2Standard non polar33892256
Citicoline,3TBDMS,isomer #14CC(C)(C)[Si](C)(C)OP(=O)(OC[C@H]1O[C@@H](N2C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC2=O)[C@H](O)[C@@H]1O)OP(=O)(O)OCC[N+](C)(C)C4901.5Standard polar33892256
Citicoline,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C4055.5Semi standard non polar33892256
Citicoline,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C3780.7Standard non polar33892256
Citicoline,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O[Si](C)(C)C(C)(C)C5289.2Standard polar33892256
Citicoline,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C14150.5Semi standard non polar33892256
Citicoline,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13902.1Standard non polar33892256
Citicoline,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O[Si](C)(C)C(C)(C)C)C=C15198.4Standard polar33892256
Citicoline,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=CC(N)=NC1=O4053.9Semi standard non polar33892256
Citicoline,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=CC(N)=NC1=O3784.2Standard non polar33892256
Citicoline,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@H]1N1C=CC(N)=NC1=O5087.7Standard polar33892256
Citicoline,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C14184.7Semi standard non polar33892256
Citicoline,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13900.4Standard non polar33892256
Citicoline,3TBDMS,isomer #5CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C14982.3Standard polar33892256
Citicoline,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C14184.6Semi standard non polar33892256
Citicoline,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C13901.3Standard non polar33892256
Citicoline,3TBDMS,isomer #6CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H]2O[Si](C)(C)C(C)(C)C)C=C14983.2Standard polar33892256
Citicoline,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)O[C@H]1N1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O4112.9Semi standard non polar33892256
Citicoline,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)O[C@H]1N1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O3966.6Standard non polar33892256
Citicoline,3TBDMS,isomer #7CC(C)(C)[Si](C)(C)O[C@@H]1[C@H](O)[C@@H](COP(=O)(O)OP(=O)(O)OCC[N+](C)(C)C)O[C@H]1N1C=CC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=NC1=O5096.5Standard polar33892256
Citicoline,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O4055.7Semi standard non polar33892256
Citicoline,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O3755.6Standard non polar33892256
Citicoline,3TBDMS,isomer #8CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C(C)(C)C)O[C@@H](N2C=CC(N)=NC2=O)[C@@H]1O5064.4Standard polar33892256
Citicoline,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C14187.0Semi standard non polar33892256
Citicoline,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C13871.7Standard non polar33892256
Citicoline,3TBDMS,isomer #9CC(C)(C)[Si](C)(C)NC1=NC(=O)N([C@@H]2O[C@H](COP(=O)(O[Si](C)(C)C(C)(C)C)OP(=O)(O)OCC[N+](C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]2O)C=C14956.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citicoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-0006-0001900000-a9f38ff6b185b45f04b32020-09-18HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-03e9-0590000000-b021677d064d65810ee02020-09-18HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-001i-0900000000-7570bbb10dd9fa2884422020-09-18HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-000i-0000900000-8b411373962b073b4d222020-09-18HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive-QTOFsplash10-000i-0001900000-6e7cc437ad79eb13c0322020-09-18HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-01qi-1932200000-9c3803cefdd9c6285a7c2020-09-18HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-004i-6505900000-3d534aab6e40915c36422020-09-18HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-004i-6505900000-fc13e5ad403e7faf82182020-09-18HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline LC-ESI-QTOF , negative-QTOFsplash10-004i-6505900000-3d534aab6e40915c36422020-09-18HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline LC-ESI-QTOF , negative-QTOFsplash10-004i-6505900000-fc13e5ad403e7faf82182020-09-18HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline LC-ESI-QTOF , positive-QTOFsplash10-000i-0000900000-8b411373962b073b4d222020-09-18HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline LC-ESI-QTOF , positive-QTOFsplash10-000i-0001900000-6e7cc437ad79eb13c0322020-09-18HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citicoline LC-ESI-QTOF , positive-QTOFsplash10-01qi-1932200000-4a7ae92c6e127d2ce4532020-09-18HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citicoline 10V, Positive-QTOFsplash10-03di-2910000000-16739ec448981ed6c8062019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citicoline 20V, Positive-QTOFsplash10-03di-4900000000-ebcd1f8663a2ad408f472019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citicoline 40V, Positive-QTOFsplash10-03di-9700000000-626eb1582def7bb92bdf2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citicoline 10V, Positive-QTOFsplash10-000i-0203900000-5a3407661bff891d49f12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citicoline 20V, Positive-QTOFsplash10-000i-0521900000-69ce5c8e8a3a904999e12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citicoline 40V, Positive-QTOFsplash10-01t9-8930000000-30f725e6639e920d882b2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2020-09-18Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2020-09-18Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen LocationsNot Available
Tissue Locations
  • Brain
  • Erythrocyte
  • Intestine
  • Placenta
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12153
Phenol Explorer Compound IDNot Available
FooDB IDFDB022608
KNApSAcK IDC00007231
Chemspider ID13208
KEGG Compound IDC00307
BioCyc IDCDP-CHOLINE
BiGG IDNot Available
Wikipedia LinkCiticoline
METLIN ID6229
PubChem Compound13805
PDB IDNot Available
ChEBI ID49086
Food Biomarker OntologyNot Available
VMH IDCDPCHOL
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceFujio, Tatsuro. New production method of useful substances using ATP regeneration system. Kiraru Tekunoroji no Shintenkai (2001), 187-198.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Porciatti V, Schiavi C, Benedetti P, Baldi A, Campos EC: Cytidine-5'-diphosphocholine improves visual acuity, contrast sensitivity and visually-evoked potentials of amblyopic subjects. Curr Eye Res. 1998 Feb;17(2):141-8. [PubMed:9523091 ]
  2. Babb SM, Wald LL, Cohen BM, Villafuerte RA, Gruber SA, Yurgelun-Todd DA, Renshaw PF: Chronic citicoline increases phosphodiesters in the brains of healthy older subjects: an in vivo phosphorus magnetic resonance spectroscopy study. Psychopharmacology (Berl). 2002 May;161(3):248-54. Epub 2002 Mar 22. [PubMed:12021827 ]
  3. Alvarez XA, Mouzo R, Pichel V, Perez P, Laredo M, Fernandez-Novoa L, Corzo L, Zas R, Alcaraz M, Secades JJ, Lozano R, Cacabelos R: Double-blind placebo-controlled study with citicoline in APOE genotyped Alzheimer's disease patients. Effects on cognitive performance, brain bioelectrical activity and cerebral perfusion. Methods Find Exp Clin Pharmacol. 1999 Nov;21(9):633-44. [PubMed:10669911 ]
  4. Laurence AD, Layton M, Duley JA, Simmonds HA: Elevated erythrocyte CDP-choline levels associated with beta-thalassaemia in patients with transfusion independent anaemia. Nucleosides Nucleotides Nucleic Acids. 2004 Oct;23(8-9):1265-7. [PubMed:15571243 ]
  5. Friedman D, Cycowicz YM, Bersick M: The late negative episodic memory effect: the effect of recapitulating study details at test. Brain Res Cogn Brain Res. 2005 May;23(2-3):185-98. Epub 2004 Nov 21. [PubMed:15820627 ]
  6. Alvarez XA, Laredo M, Corzo D, Fernandez-Novoa L, Mouzo R, Perea JE, Daniele D, Cacabelos R: Citicoline improves memory performance in elderly subjects. Methods Find Exp Clin Pharmacol. 1997 Apr;19(3):201-10. [PubMed:9203170 ]
  7. Paglia DE, Valentine WN, Nakatani M, Rauth BJ: Selective accumulation of cytosol CDP-choline as an isolated erythrocyte defect in chronic hemolysis. Proc Natl Acad Sci U S A. 1983 May;80(10):3081-5. [PubMed:6574471 ]
  8. Hayashida K: [Usefulness of SPECT images in helping radiologists understand brain diseases]. Nihon Igaku Hoshasen Gakkai Zasshi. 2001 Apr;61(5):208-14. [PubMed:11398344 ]
  9. Renshaw PF, Daniels S, Lundahl LH, Rogers V, Lukas SE: Short-term treatment with citicoline (CDP-choline) attenuates some measures of craving in cocaine-dependent subjects: a preliminary report. Psychopharmacology (Berl). 1999 Feb;142(2):132-8. [PubMed:10102764 ]
  10. Weiss GB: Metabolism and actions of CDP-choline as an endogenous compound and administered exogenously as citicoline. Life Sci. 1995;56(9):637-60. [PubMed:7869846 ]
  11. Petersen A, Borregaard N: A family with chronic haemolysis and selective accumulation of erythrocyte CDP-choline. Leukemia. 1997 Aug;11(8):1373-6. [PubMed:9264395 ]
  12. de la Morena E: Efficacy of CDP-choline in the treatment of senile alterations in memory. Ann N Y Acad Sci. 1991;640:233-6. [PubMed:1776744 ]
  13. Secades JJ, Lorenzo JL: Citicoline: pharmacological and clinical review, 2006 update. Methods Find Exp Clin Pharmacol. 2006 Sep;28 Suppl B:1-56. [PubMed:17171187 ]
  14. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Enzymes

Enzyme Details
1. Choline-phosphate cytidylyltransferase B
General function:
Involved in catalytic activity
Specific function:
Controls phosphatidylcholine synthesis.
Gene Name:
PCYT1B
Uniprot ID:
Q9Y5K3
Molecular weight:
40228.99
Reactions
Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + Citicolinedetails
Enzyme Details
2. Choline-phosphate cytidylyltransferase A
General function:
Involved in catalytic activity
Specific function:
Controls phosphatidylcholine synthesis.
Gene Name:
PCYT1A
Uniprot ID:
P49585
Molecular weight:
41730.67
Reactions
Cytidine triphosphate + Phosphorylcholine → Pyrophosphate + Citicolinedetails
Enzyme Details
3. Phosphatidylcholine:ceramide cholinephosphotransferase 2
General function:
Involved in catalytic activity
Specific function:
Bidirectional lipid cholinephosphotransferase capable of converting phosphatidylcholine (PC) and ceramide to sphingomyelin (SM) and diacylglycerol (DAG) and vice versa. Direction is dependent on the relative concentrations of DAG and ceramide as phosphocholine acceptors. Directly and specifically recognizes the choline head group on the substrate. Also requires two fatty chains on the choline-P donor molecule in order to be recognized efficiently as a substrate. Does not function strictly as a SM synthase. Required for cell growth
Gene Name:
SGMS2
Uniprot ID:
Q8NHU3
Molecular weight:
42279.8
Enzyme Details
4. Phosphatidylcholine:ceramide cholinephosphotransferase 1
General function:
Involved in catalytic activity
Specific function:
Bidirectional lipid cholinephosphotransferase capable of converting phosphatidylcholine (PC) and ceramide to sphingomyelin (SM) and diacylglycerol (DAG) and vice versa. Direction is dependent on the relative concentrations of DAG and ceramide as phosphocholine acceptors. Directly and specifically recognizes the choline head group on the substrate. Also requires two fatty chains on the choline-P donor molecule in order to be recognized efficiently as a substrate. Does not function strictly as a SM synthase. Suppresses BAX-mediated apoptosis and also prevents cell death in response to stimuli such as hydrogen peroxide, osmotic stress, elevated temperature and exogenously supplied sphingolipids. May protect against cell death by reversing the stress-inducible increase in levels of proapoptotic ceramide. Required for cell growth
Gene Name:
SGMS1
Uniprot ID:
Q86VZ5
Molecular weight:
49207.3
Enzyme Details
5. Cholinephosphotransferase 1
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes phosphatidylcholine biosynthesis from CDP-choline. It thereby plays a central role in the formation and maintenance of vesicular membranes.
Gene Name:
CHPT1
Uniprot ID:
Q8WUD6
Molecular weight:
45096.535
Reactions
Citicoline + 1,2-diacylglycerol → Cytidine monophosphate + a phosphatidylcholinedetails
Citicoline + 1,2-Diacyl-sn-glycerol → Cytidine monophosphate + Phosphatidylcholinedetails
Citicoline + 1-Alkyl-2-acetyl-sn-glycerol → Cytidine monophosphate + 2-Acetyl-1-alkyl-sn-glycero-3-phosphocholinedetails
1-Alkyl-2-acylglycerol + Citicoline → 1-Radyl-2-acyl-sn-glycero-3-phosphocholine + Cytidine monophosphatedetails
Enzyme Details
6. Choline/ethanolaminephosphotransferase 1
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes both phosphatidylcholine and phosphatidylethanolamine biosynthesis from CDP-choline and CDP-ethanolamine, respectively. Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. Has a higher cholinephosphotransferase activity than ethanolaminephosphotransferase activity.
Gene Name:
CEPT1
Uniprot ID:
Q9Y6K0
Molecular weight:
46553.135
Reactions
Citicoline + 1,2-diacylglycerol → Cytidine monophosphate + a phosphatidylcholinedetails
Citicoline + 1,2-Diacyl-sn-glycerol → Cytidine monophosphate + Phosphatidylcholinedetails
Citicoline + 1-Alkyl-2-acetyl-sn-glycerol → Cytidine monophosphate + 2-Acetyl-1-alkyl-sn-glycero-3-phosphocholinedetails
1-Alkyl-2-acylglycerol + Citicoline → 1-Radyl-2-acyl-sn-glycero-3-phosphocholine + Cytidine monophosphatedetails
Enzyme Details
7. Manganese-dependent ADP-ribose/CDP-alcohol diphosphatase
General function:
Not Available
Specific function:
Hydrolyzes ADP-ribose, IDP-ribose, CDP-glycerol, CDP-choline and CDP-ethanolamine, but not other non-reducing ADP-sugars or CDP-glucose. May be involved in immune cell signaling as suggested by the second-messenger role of ADP-ribose, which activates TRPM2 as a mediator of oxidative/nitrosative stress (By similarity).
Gene Name:
ADPRM
Uniprot ID:
Q3LIE5
Molecular weight:
39529.105
Reactions
Citicoline + Water → Cytidine monophosphate + Phosphorylcholinedetails