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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (65) Show 65 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:48:15 UTC

HMDB ID

HMDB0000082

Secondary Accession Numbers

HMDB00082

Metabolite Identification

Common Name

Cytidine triphosphate

Description

Cytidine triphosphate (CTP), also known as 5'-CTP, is pyrimidine nucleoside triphosphate. Formally, CTP is an ester of cytidine and triphosphoric acid. It belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups. CTP, much like ATP, consists of a base (cytosine), a ribose sugar, and three phosphate groups. CTP is a high-energy molecule similar to ATP, but its role as an energy coupler is limited to a much smaller subset of metabolic reactions. CTP exists in all living species, ranging from bacteria to plants to humans and is used in the synthesis of RNA via RNA polymerase. Another enzyme known as cytidine triphosphate synthetase (CTPS) mediates the conversion of uridine triphosphate (UTP) into cytidine triphosphate (CTP) which is the rate-limiting step of de novo CTP biosynthesis. CTPS catalyzes a complex set of reactions that include the ATP-dependent transfer of the amide nitrogen from glutamine (i.e., glutaminase reaction) to the C-4 position of UTP to generate CTP. GTP stimulates the glutaminase reaction by accelerating the formation of a covalent glutaminyl enzyme intermediate. CTPS activity regulates the intracellular rates of RNA synthesis, DNA synthesis, and phospholipid synthesis. CTPS is an established target for a number of antiviral, antineoplastic, and antiparasitic drugs. CTP also acts as an inhibitor of the enzyme known as aspartate carbamoyltransferase, which is used in pyrimidine biosynthesis. CTP also reacts with nitrogen-containing alcohols to form coenzymes that participate in the formation of phospholipids. In particular, CTP is the direct precursor of the activated, phospholipid pathway intermediates CDP-diacylglycerol, CDP-choline, and CDP-ethanolamine ((PMID: 18439916 ). CDP-diacylglycerol is the source of the phosphatidyl moiety for phosphatidylserine, phosphatidylethanolamine, and phosphatidylcholine (synthesized by way of the CDP-diacylglycerol pathway) as well as phosphatidylglycerol, cardiolipin, and phosphatidylinositol (PMID: 18439916 ).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652308122017282D          

 29 30  0  0  1  0            999 V2000
    2.0728    0.1685    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8634    0.4296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4300    0.6428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8321   -0.6394    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4821   -0.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0352    1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7597    0.1478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0071   -0.6394    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3168   -1.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2693    0.1375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3171   -0.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8156    1.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275    0.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5156   -1.2994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4377    0.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359   -0.1478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2214    1.2031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575   -0.1478    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2790   -0.1478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609   -0.9728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609    0.6738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1040   -0.1443    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9255   -0.1443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074   -0.9660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    0.6772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7471   -0.1410    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7505   -0.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5687   -0.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7505    0.6807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  6  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  1  0  0  0
  8 14  1  6  0  0  0
 10 15  2  0  0  0  0
 13 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  2  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  2  0  0  0  0
  7  8  1  0  0  0  0
 12 15  1  0  0  0  0
M  END

     RDKit          3D

 45 46  0  0  0  0  0  0  0  0999 V2000
   -5.4298    3.5201   -1.8999 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8626    2.4101   -1.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6231    2.5998   -0.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0535    1.5219    0.0762 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6782    0.3321    0.1356 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0291   -0.7414    0.8534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9951   -0.2739    1.6168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0247   -1.2285    1.7200 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2496   -0.6497    1.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2911   -1.5693    1.1586 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6502   -0.8923    0.4636 P   0  0  2  0  0  5  0  0  0  0  0  0
    2.5189    0.6142    0.5051 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8707   -1.4343   -1.1405 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0744   -1.2819    1.2961 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3726   -1.0056    0.2272 P   0  0  1  0  0  5  0  0  0  0  0  0
    6.1942   -2.2604    0.0434 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8255   -0.5038   -1.2884 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3543    0.2392    0.8510 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1026    1.6745    0.0332 P   0  0  2  0  0  5  0  0  0  0  0  0
    7.3930    2.4820    0.0848 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8931    2.6017    0.7372 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7187    1.4501   -1.5939 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244   -2.4104    0.8746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1730   -3.3130    1.6216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3812   -1.7202   -0.1083 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2811   -2.6172   -0.6480 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8719    0.1838   -0.4683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4705   -0.9332   -0.4192 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4524    1.2088   -1.1322 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5011    4.4261   -1.3661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7617    3.4610   -2.8747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1194    3.5568   -0.6467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0947    1.6353    0.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7712   -1.3468    1.4420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229   -1.4885    2.7728 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0103   -0.3855    0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5421    0.3011    1.5783 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5699   -2.3882   -1.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4444   -0.8471   -1.9754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9258    3.5346    0.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5343    1.2867   -2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5791   -2.8762    0.3418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2304   -3.0032    2.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7946   -1.1643   -0.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1100   -2.7050   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 11 10  1  1
 11 12  2  0
 11 13  1  0
 11 14  1  0
 15 14  1  1
 15 16  2  0
 15 17  1  0
 15 18  1  0
 19 18  1  1
 19 20  2  0
 19 21  1  0
 19 22  1  0
  8 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  0
  5 27  1  0
 27 28  2  0
 27 29  1  0
 29  2  2  0
 25  6  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  4 33  1  0
  6 34  1  1
  8 35  1  1
  9 36  1  0
  9 37  1  0
 13 38  1  0
 17 39  1  0
 21 40  1  0
 22 41  1  0
 23 42  1  6
 24 43  1  0
 25 44  1  6
 26 45  1  0
M  END


  Mrv1652308122017282D          

 29 30  0  0  1  0            999 V2000
    2.0728    0.1685    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8634    0.4296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4300    0.6428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8321   -0.6394    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4821   -0.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0352    1.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7597    0.1478    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0071   -0.6394    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3168   -1.3028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2693    0.1375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3171   -0.9281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8156    1.4988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0275    0.4021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5156   -1.2994    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4377    0.9487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359   -0.1478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2214    1.2031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4575   -0.1478    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2790   -0.1478    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609   -0.9728    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4609    0.6738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1040   -0.1443    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9255   -0.1443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074   -0.9660    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    0.6772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7471   -0.1410    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7505   -0.9625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5687   -0.1375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7505    0.6807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
  4  9  1  6  0  0  0
  5 10  1  0  0  0  0
  5 11  2  0  0  0  0
  6 12  2  0  0  0  0
  7 13  1  1  0  0  0
  8 14  1  6  0  0  0
 10 15  2  0  0  0  0
 13 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 18 21  2  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  2  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 26 29  2  0  0  0  0
  7  8  1  0  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000082

> <DATABASE_NAME>
hmdb

> <SMILES>
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

> <INCHI_KEY>
PCDQPRRSZKQHHS-XVFCMESISA-N

> <FORMULA>
C9H16N3O14P3

> <MOLECULAR_WEIGHT>
483.1563

> <EXACT_MASS>
482.984511771

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
35.87464665037284

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <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)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid

> <ALOGPS_LOGP>
-0.34

> <JCHEM_LOGP>
-4.098699917086834

> <ALOGPS_LOGS>
-1.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
2.5325474649790083

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.9436292779809294

> <JCHEM_PKA_STRONGEST_BASIC>
-0.07552457534039747

> <JCHEM_POLAR_SURFACE_AREA>
268.19999999999993

> <JCHEM_REFRACTIVITY>
87.16349999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.12e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
CTP

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/NC1=NC(=O)N(C=C1)%5BC@@H%5D1O%5...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:44})
 45 46  0  0  0  0  0  0  0  0999 V2000
   -5.9086    4.5290   -1.0712 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4167    3.3542   -0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8779    2.4443   -1.3524 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3982    1.3036   -0.8600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9073    0.4829   -1.6171 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4458    1.0418    0.4592 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9903    1.9459    1.3211 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4770    3.1128    0.8366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9101   -0.2220    0.9711 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9352   -0.2303    2.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5605   -0.4243    0.4980 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3225   -1.8434    0.6221 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1046   -2.1023    1.6582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1686   -2.2714   -0.2868 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0475   -1.6821    0.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4676   -1.9180   -0.5432 P   0  0  1  0  0  0  0  0  0  0  0  0
    1.8823   -3.4686   -0.4173 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3624   -1.5500   -1.9728 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5876   -1.0038    0.1653 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0364   -0.4625   -0.2820 P   0  0  1  0  0  0  0  0  0  0  0  0
    5.1039   -1.6656   -0.2121 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9642    0.0532   -1.6674 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4961    0.7211    0.7079 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5717    1.9144    0.6007 P   0  0  0  0  0  0  0  0  0  0  0  0
    4.9469    3.1244   -0.2581 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9404    2.4389    2.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7957    1.4168   -0.0661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6420   -2.5061    0.1682 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5927   -2.7714   -0.8879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9203   -3.6620    0.9609 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7123   -1.4147    0.4055 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1919   -1.1396   -0.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6855   -1.8647    1.3500 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8620    4.6940   -2.0259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3056    5.1908   -0.4835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0290    1.7359    2.3798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9129    3.8435    1.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0759   -3.3574   -0.2694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3667   -1.9401   -1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9698   -3.7797    0.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2033   -2.0526    0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1406    3.5003    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5849    3.1596    2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7382   -4.1175    0.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1755   -2.6488    1.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  2  0  0  0  0
  7 36  1  0  0  0  0
  8 37  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  9 31  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 12 28  1  0  0  0  0
 14 15  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  6  0  0  0
 16 19  1  0  0  0  0
 17 40  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  6  0  0  0
 20 23  1  0  0  0  0
 21 41  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 42  1  0  0  0  0
 26 43  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 30 44  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 45  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 12-AUG-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-AUG-20         0                                  
HETATM    1  C   UNK     0       3.869   0.315   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       5.345   0.802   0.000  0.00  0.00           N+0
HETATM    3  O   UNK     0       2.669   1.200   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.420  -1.194   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.500  -0.225   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.666   2.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.418   0.276   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.880  -1.194   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.325  -2.432   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       7.969   0.257   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0       6.192  -1.732   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.122   2.798   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.051   0.751   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.962  -2.426   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.284   1.771   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.187  -0.276   0.000  0.00  0.00           O+0
HETATM   17  N   UNK     0       9.747   2.246   0.000  0.00  0.00           N+0
HETATM   18  P   UNK     0      -2.721  -0.276   0.000  0.00  0.00           P+0
HETATM   19  O   UNK     0      -4.254  -0.276   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.727  -1.816   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.727   1.258   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      -5.794  -0.269   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0      -7.328  -0.269   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.800  -1.803   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -5.800   1.264   0.000  0.00  0.00           O+0
HETATM   26  P   UNK     0      -8.861  -0.263   0.000  0.00  0.00           P+0
HETATM   27  O   UNK     0      -8.868  -1.797   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0     -10.395  -0.257   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -8.868   1.271   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1    8    9                                                  
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13    8                                                  
CONECT    8    4   14    7                                                  
CONECT    9    4                                                            
CONECT   10    5   15                                                       
CONECT   11    5                                                            
CONECT   12    6   15                                                       
CONECT   13    7   16                                                       
CONECT   14    8                                                            
CONECT   15   10   17   12                                                  
CONECT   16   13   18                                                       
CONECT   17   15                                                            
CONECT   18   16   19   20   21                                             
CONECT   19   18   22                                                       
CONECT   20   18                                                            
CONECT   21   18                                                            
CONECT   22   19   23   24   25                                             
CONECT   23   22   26                                                       
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   23   27   28   29                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   26                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   60    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/NC1=NC(=O)N(C=C1)%5BC@@H%5D1O%5... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  N   UNL     1      -5.909   4.529  -1.071  1.00  0.00           N  
HETATM    2  C   UNL     1      -5.417   3.354  -0.551  1.00  0.00           C  
HETATM    3  N   UNL     1      -4.878   2.444  -1.352  1.00  0.00           N  
HETATM    4  C   UNL     1      -4.398   1.304  -0.860  1.00  0.00           C  
HETATM    5  O   UNL     1      -3.907   0.483  -1.617  1.00  0.00           O  
HETATM    6  N   UNL     1      -4.446   1.042   0.459  1.00  0.00           N  
HETATM    7  C   UNL     1      -4.990   1.946   1.321  1.00  0.00           C  
HETATM    8  C   UNL     1      -5.477   3.113   0.837  1.00  0.00           C  
HETATM    9  C   UNL     1      -3.910  -0.222   0.971  1.00  0.00           C  
HETATM   10  H   UNL     1      -3.935  -0.230   2.061  1.00  0.00           H  
HETATM   11  O   UNL     1      -2.561  -0.424   0.498  1.00  0.00           O  
HETATM   12  C   UNL     1      -2.322  -1.843   0.622  1.00  0.00           C  
HETATM   13  H   UNL     1      -2.105  -2.102   1.658  1.00  0.00           H  
HETATM   14  C   UNL     1      -1.169  -2.271  -0.287  1.00  0.00           C  
HETATM   15  O   UNL     1       0.048  -1.682   0.178  1.00  0.00           O  
HETATM   16  P   UNL     1       1.468  -1.918  -0.543  1.00  0.00           P  
HETATM   17  O   UNL     1       1.882  -3.469  -0.417  1.00  0.00           O  
HETATM   18  O   UNL     1       1.362  -1.550  -1.973  1.00  0.00           O  
HETATM   19  O   UNL     1       2.588  -1.004   0.165  1.00  0.00           O  
HETATM   20  P   UNL     1       4.036  -0.463  -0.282  1.00  0.00           P  
HETATM   21  O   UNL     1       5.104  -1.666  -0.212  1.00  0.00           O  
HETATM   22  O   UNL     1       3.964   0.053  -1.667  1.00  0.00           O  
HETATM   23  O   UNL     1       4.496   0.721   0.708  1.00  0.00           O  
HETATM   24  P   UNL     1       5.572   1.914   0.601  1.00  0.00           P  
HETATM   25  O   UNL     1       4.947   3.124  -0.258  1.00  0.00           O  
HETATM   26  O   UNL     1       5.940   2.439   2.078  1.00  0.00           O  
HETATM   27  O   UNL     1       6.796   1.417  -0.066  1.00  0.00           O  
HETATM   28  C   UNL     1      -3.642  -2.506   0.168  1.00  0.00           C  
HETATM   29  H   UNL     1      -3.593  -2.771  -0.888  1.00  0.00           H  
HETATM   30  O   UNL     1      -3.920  -3.662   0.961  1.00  0.00           O  
HETATM   31  C   UNL     1      -4.712  -1.415   0.406  1.00  0.00           C  
HETATM   32  H   UNL     1      -5.192  -1.140  -0.534  1.00  0.00           H  
HETATM   33  O   UNL     1      -5.686  -1.865   1.350  1.00  0.00           O  
HETATM   34  H   UNL     1      -5.862   4.694  -2.026  1.00  0.00           H  
HETATM   35  H   UNL     1      -6.306   5.191  -0.483  1.00  0.00           H  
HETATM   36  H   UNL     1      -5.029   1.736   2.380  1.00  0.00           H  
HETATM   37  H   UNL     1      -5.913   3.844   1.502  1.00  0.00           H  
HETATM   38  H   UNL     1      -1.076  -3.357  -0.269  1.00  0.00           H  
HETATM   39  H   UNL     1      -1.367  -1.940  -1.306  1.00  0.00           H  
HETATM   40  H   UNL     1       1.970  -3.780   0.494  1.00  0.00           H  
HETATM   41  H   UNL     1       5.203  -2.053   0.668  1.00  0.00           H  
HETATM   42  H   UNL     1       4.141   3.500   0.121  1.00  0.00           H  
HETATM   43  H   UNL     1       6.585   3.160   2.089  1.00  0.00           H  
HETATM   44  H   UNL     1      -4.738  -4.117   0.719  1.00  0.00           H  
HETATM   45  H   UNL     1      -6.176  -2.649   1.067  1.00  0.00           H  
CONECT    1    2   34   35                                            
CONECT    2    1    3    3    8                                       
CONECT    3    2    2    4                                            
CONECT    4    3    5    5    6                                       
CONECT    5    4    4                                                 
CONECT    6    4    7    9                                            
CONECT    7    6    8    8   36                                       
CONECT    8    7    7    2   37                                       
CONECT    9    6   10   11   31                                       
CONECT   10    9                                                      
CONECT   11    9   12                                                 
CONECT   12   11   13   14   28                                       
CONECT   13   12                                                      
CONECT   14   12   15   38   39                                       
CONECT   15   14   16                                                 
CONECT   16   15   17   18   18                                       
CONECT   16   19                                                      
CONECT   17   16   40                                                 
CONECT   18   16   16                                                 
CONECT   19   16   20                                                 
CONECT   20   19   21   22   22                                       
CONECT   20   23                                                      
CONECT   21   20   41                                                 
CONECT   22   20   20                                                 
CONECT   23   20   24                                                 
CONECT   24   23   25   26   27                                       
CONECT   24   27                                                      
CONECT   25   24   42                                                 
CONECT   26   24   43                                                 
CONECT   27   24   24                                                 
CONECT   28   12   29   30   31                                       
CONECT   29   28                                                      
CONECT   30   28   44                                                 
CONECT   31   28   32    9   33                                       
CONECT   32   31                                                      
CONECT   33   31   45                                                 
CONECT   34    1                                                      
CONECT   35    1                                                      
CONECT   36    7                                                      
CONECT   37    8                                                      
CONECT   38   14                                                      
CONECT   39   14                                                      
CONECT   40   17                                                      
CONECT   41   21                                                      
CONECT   42   25                                                      
CONECT   43   26                                                      
CONECT   44   30                                                      
CONECT   45   33                                                      
MASTER        0    0    0    0    0    0    0    0   45    0   45    0
END

https://cactus.nci.nih.gov/chemical/structure/NC1=NC(=O)N(C=C1)%5BC@@H%5D1O%5...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:44})
 45 46  0  0  0  0  0  0  0  0999 V2000
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    4.1406    3.5003    0.1209 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5849    3.1596    2.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7382   -4.1175    0.7187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1755   -2.6488    1.0666 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  2  3  2  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  9  1  0  0  0  0
  7  8  2  0  0  0  0
  7 36  1  0  0  0  0
  8 37  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
  9 31  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 12 28  1  0  0  0  0
 14 15  1  0  0  0  0
 14 38  1  0  0  0  0
 14 39  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  6  0  0  0
 16 19  1  0  0  0  0
 17 40  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  6  0  0  0
 20 23  1  0  0  0  0
 21 41  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 42  1  0  0  0  0
 26 43  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 28 31  1  0  0  0  0
 30 44  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  0  0  0  0
 33 45  1  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
5'-CTP	ChEBI
Cytidine 5'-triphosphate	ChEBI
CYTIDINE-5'-triphosphATE	ChEBI
H4CTP	ChEBI
Cytidine 5'-triphosphoric acid	Generator
CYTIDINE-5'-triphosphoric acid	Generator
Cytidine triphosphoric acid	Generator
5'-(Tetrahydrogen triphosphate) cytidine	HMDB
CTP	HMDB
Cytidine 3'-triphosphate	HMDB
Cytidine 5'-(tetrahydrogen triphosphate)	HMDB
Cytidine 5-prime-triphosphate	HMDB
Cytidine mono	HMDB
Cytidine mono(tetrahydrogen triphosphate) (ester)	HMDB
Deoxycytosine triphosphate	HMDB
Triphosphate, cytidine	HMDB
CRPPP	HMDB
Magnesium CTP	HMDB
MG CTP	HMDB

Chemical Formula

C₉H₁₆N₃O₁₄P₃

Average Molecular Weight

483.1563

Monoisotopic Molecular Weight

482.984511771

IUPAC Name

({[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)phosphonic acid

Traditional Name

CTP

CAS Registry Number

65-47-4

SMILES

NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O

InChI Identifier

InChI=1S/C9H16N3O14P3/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(24-8)3-23-28(19,20)26-29(21,22)25-27(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H,21,22)(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1

InChI Key

PCDQPRRSZKQHHS-XVFCMESISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
Glycosyl compound
N-glycosyl compound
Monosaccharide phosphate
Hydroxypyrimidine
Monoalkyl phosphate
Hydropyrimidine
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Pyrimidine
Heteroaromatic compound
Tetrahydrofuran
1,2-diol
Secondary alcohol
Azacycle
Oxacycle
Organoheterocyclic compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

cytidine 5'-phosphate (CHEBI:17677 )
pyrimidine ribonucleoside 5'-triphosphate (CHEBI:17677 )
Ribonucleotides (C00063 )
Coenzymes (C00063 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Tissue and substructures:

All tissues

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical pathway:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	215 - 218 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	11.2 g/L	ALOGPS
logP	-0.34	ALOGPS
logP	-4.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	0.94	ChemAxon
pKa (Strongest Basic)	-0.076	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	268.2 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	87.16 m³·mol⁻¹	ChemAxon
Polarizability	35.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
AllCCS	[M-H]-	Experimental	Not Available	183.3	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000370
AllCCS	[M+H]+	Experimental	Not Available	188.6	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000370
DarkChem	[M+H]+	Predicted	Not Available	201.807	31661259
DarkChem	[M-H]-	Predicted	Not Available	189.757	31661259
AllCCS	[M+H]+	Predicted	Not Available	193.606	32859911
AllCCS	[M-H]-	Predicted	Not Available	185.69	32859911

Retention Indices

Underivatized

Not Available

Derivatized

Derivative	Value	Reference
Cytidine triphosphate,1TMS,#1	3871.4453	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,1TMS,#2	3859.8354	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,1TMS,#3	3913.1414	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,1TMS,#4	3926.6902	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,1TMS,#5	3913.664	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,1TMS,#6	3904.549	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#1	3744.235	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#2	3813.9766	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#3	3831.0823	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#4	3802.841	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#5	3835.5525	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#6	3801.7559	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#7	3821.0437	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#8	3791.473	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#9	3828.058	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#10	3865.1682	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#11	3858.1191	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#12	3895.3542	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#13	3863.7505	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#14	3908.7397	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#15	3845.8035	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#16	3878.8867	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TMS,#17	3873.6501	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,1TBDMS,#1	4109.4434	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,1TBDMS,#2	4104.9805	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,1TBDMS,#3	4163.832	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,1TBDMS,#4	4177.9116	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,1TBDMS,#5	4157.2856	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,1TBDMS,#6	4181.29	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#1	4158.0093	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#2	4222.3013	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#3	4232.1294	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#4	4225.54	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#5	4289.976	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#6	4222.1924	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#7	4234.958	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#8	4228.3086	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#9	4292.2437	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#10	4271.2637	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#11	4262.6343	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#12	4341.135	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#13	4263.6924	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#14	4348.305	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#15	4254.26	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#16	4343.573	https://arxiv.org/abs/1905.12712
Cytidine triphosphate,2TBDMS,#17	4258.7197	https://arxiv.org/abs/1905.12712

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-002b-8965400000-028238d320c37d90d959	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-03l3-4529211000-fc9c3bce80ab4bd56bec	2017-10-06	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00b9-5685900000-b067d3b0af4c194d5224	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-0309200000-33e695326ec0d28103b4	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-057j-1926700000-417741bbe965170223c0	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 10V, negative	splash10-001i-0201900000-d0f4b76212c986ba5256	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 15V, negative	splash10-053r-0602900000-3b15e1314bb085815ee1	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 17V, negative	splash10-053r-0913800000-a9781bf9478c1556ea6f	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 20V, negative	splash10-0a59-1903500000-ca05dcfb3a7e6249de5f	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 23V, negative	splash10-0a59-1912200000-ed35edf8dd897cfb189f	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 25V, negative	splash10-0a4i-1912100000-02368a767858b532e343	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 27V, negative	splash10-0a4i-1901100000-7e158597e6539f859f18	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 30V, negative	splash10-0a4i-2901000000-e6ffe54064813cca999a	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 33V, negative	splash10-0a4i-2901000000-878ed1a77bece120cab0	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 35V, negative	splash10-0a4i-3900000000-5609836a3262551e3f22	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 40V, negative	splash10-0a6r-4900000000-25ee9e049ac582f88998	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QTOF 45V, negative	splash10-0a6r-6900000000-df141b7c324466d11ca1	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 33V, negative	splash10-001i-0109000000-e4e73cfc21a26fa84c94	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, negative	splash10-001i-0100900000-1d8f337531a62dff2aef	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 23V, negative	splash10-053r-0703900000-43af4aa75af7c1b90a19	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 29V, negative	splash10-0a4i-0902200000-9cabc619fb140d01b9d7	2020-07-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0901100000-c35d289f50f6f03e2607	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-2901000000-52ceb0833c1f651ee73e	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-5900000000-b2b882bb438556aea202	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01q9-0520900000-0e5b8be0fa0c2178439b	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0bwi-9660200000-4db67ca241ce3068a27f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9200000000-1f093b0fe69d03ecea98	2016-09-12	View Spectrum

NMR

Spectrum Type	Description	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	2016-10-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	View Spectrum
2D NMR	[¹H, ¹H] 2D NMR Spectrum (predicted)	2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, H₂O, predicted)	2012-12-04	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria
Nucleus

Biospecimen Locations

Cellular Cytoplasm

Tissue Locations

All Tissues

Pathways

Name	SMPDB/Pathwhiz	KEGG
Pyrimidine Metabolism
Transcription/Translation	SMP00019	Not Available
DNA Replication Fork	SMP00477	Not Available
Amino Sugar Metabolism
Sialuria or French Type Sialuria		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cellular Cytoplasm	Detected and Quantified	10 uM	Adult (>18 years old)	Both	Normal	4025817	details
Cellular Cytoplasm	Detected and Quantified	28 uM	Adult (>18 years old)	Both	Normal	4025817	details
Cellular Cytoplasm	Detected and Quantified	15 uM	Adult (>18 years old)	Both	Normal	4025817	details
Cellular Cytoplasm	Detected and Quantified	23 uM	Adult (>18 years old)	Both	Normal	4025817	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02431

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Cytidine triphosphate

METLIN ID

5136

PubChem Compound

6176

PDB ID

Not Available

ChEBI ID

17677

Food Biomarker Ontology

Not Available

VMH ID

CTP

MarkerDB ID

Not Available

References

Synthesis Reference

Simon, Ethan S.; Bednarski, Mark D.; Whitesides, George M. Synthesis of CMP-NeuAc from N-acetylglucosamine: generation of CTP from CMP using adenylate kinase. Journal of the American Chemical Society (1988), 110(21), 7159-63.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Watanabe T, Oguchi K, Ebara S, Fukui T: Measurement of 3-hydroxyisovaleric acid in urine of biotin-deficient infants and mice by HPLC. J Nutr. 2005 Mar;135(3):615-8. [PubMed:15735103 ]
Kondo T, Ohtsuka Y, Shimada M, Kawakami Y, Hiyoshi Y, Tsuji Y, Fujii H, Miwa S: Erythrocyte-oxidized glutathione transport in pyrimidine 5'-nucleotidase deficiency. Am J Hematol. 1987 Sep;26(1):37-45. [PubMed:2888306 ]
Kallander CF, Gronowitz JS, Olding-Stenkvist E: Varicella zoster virus deoxythymidine kinase is present in serum before the onset of varicella. Scand J Infect Dis. 1989;21(3):255-7. [PubMed:2547243 ]
de Korte D, Haverkort WA, van Gennip AH, Roos D: Nucleotide profiles of normal human blood cells determined by high-performance liquid chromatography. Anal Biochem. 1985 May 15;147(1):197-209. [PubMed:4025817 ]
Verschuur AC, Brinkman J, Van Gennip AH, Leen R, Vet RJ, Evers LM, Voute PA, Van Kuilenburg AB: Cyclopentenyl cytosine induces apoptosis and increases cytarabine-induced apoptosis in a T-lymphoblastic leukemic cell-line. Leuk Res. 2001 Oct;25(10):891-900. [PubMed:11532523 ]
Cornell RB, Northwood IC: Regulation of CTP:phosphocholine cytidylyltransferase by amphitropism and relocalization. Trends Biochem Sci. 2000 Sep;25(9):441-7. [PubMed:10973058 ]
Chang YF, Carman GM: CTP synthetase and its role in phospholipid synthesis in the yeast Saccharomyces cerevisiae. Prog Lipid Res. 2008 Sep;47(5):333-9. doi: 10.1016/j.plipres.2008.03.004. Epub 2008 Apr 7. [PubMed:18439916 ]

Only showing the first 10 proteins. There are 65 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Ectonucleoside triphosphate diphosphohydrolase 1

General function:: Involved in hydrolase activity
Specific function:: In the nervous system, could hydrolyze ATP and other nucleotides to regulate purinergic neurotransmission. Could also be implicated in the prevention of platelet aggregation by hydrolyzing platelet-activating ADP to AMP. Hydrolyzes ATP and ADP equally well.
Gene Name:: ENTPD1
Uniprot ID:: P49961
Molecular weight:: 58706.0

Reactions

Cytidine triphosphate + Water → CDP + Phosphate	details

Enzyme Details

2. Soluble calcium-activated nucleotidase 1

General function:: Involved in calcium ion binding
Specific function:: Calcium-dependent nucleotidase with a preference for UDP. The order of activity with different substrates is UDP > GDP > UTP > GTP. Has very low activity towards ADP and even lower activity towards ATP. Does not hydrolyze AMP and GMP. Involved in proteoglycan synthesis.
Gene Name:: CANT1
Uniprot ID:: Q8WVQ1
Molecular weight:: 44839.24

Enzyme Details

3. Ectonucleoside triphosphate diphosphohydrolase 3

General function:: Involved in hydrolase activity
Specific function:: Has a threefold preference for the hydrolysis of ATP over ADP.
Gene Name:: ENTPD3
Uniprot ID:: O75355
Molecular weight:: 59104.76

Reactions

Cytidine triphosphate + Water → CDP + Phosphate	details

Enzyme Details

4. Nucleoside diphosphate kinase, mitochondrial

General function:: Involved in nucleoside diphosphate kinase activity
Specific function:: Major role in the synthesis of nucleoside triphosphates other than ATP (By similarity).
Gene Name:: NME4
Uniprot ID:: O00746
Molecular weight:: 20658.45

Reactions

Adenosine triphosphate + CDP → ADP + Cytidine triphosphate	details

Enzyme Details

5. Nucleoside diphosphate kinase A

General function:: Involved in nucleoside diphosphate kinase activity
Specific function:: Major role in the synthesis of nucleoside triphosphates other than ATP. Possesses nucleoside-diphosphate kinase, serine/threonine-specific protein kinase, geranyl and farnesyl pyrophosphate kinase, histidine protein kinase and 3'-5' exonuclease activities. Involved in cell proliferation, differentiation and development, signal transduction, G protein-coupled receptor endocytosis, and gene expression. Required for neural development including neural patterning and cell fate determination.
Gene Name:: NME1
Uniprot ID:: P15531
Molecular weight:: 17148.635

Reactions

Adenosine triphosphate + CDP → ADP + Cytidine triphosphate	details

Enzyme Details

6. Nucleoside diphosphate kinase 7

General function:: Involved in nucleoside diphosphate kinase activity
Specific function:: Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate.
Gene Name:: NME7
Uniprot ID:: Q9Y5B8
Molecular weight:: 42491.365

Reactions

Adenosine triphosphate + CDP → ADP + Cytidine triphosphate	details

Enzyme Details

7. Nucleoside diphosphate kinase B

General function:: Involved in nucleoside diphosphate kinase activity
Specific function:: Major role in the synthesis of nucleoside triphosphates other than ATP. Negatively regulates Rho activity by interacting with AKAP13/LBC. Acts as a transcriptional activator of the MYC gene; binds DNA non-specifically (PubMed:8392752). Exhibits histidine protein kinase activity.
Gene Name:: NME2
Uniprot ID:: P22392
Molecular weight:: 30136.92

Reactions

Adenosine triphosphate + CDP → ADP + Cytidine triphosphate	details

Enzyme Details

8. Nucleoside diphosphate kinase 3

General function:: Involved in nucleoside diphosphate kinase activity
Specific function:: Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate. Probably has a role in normal hematopoiesis by inhibition of granulocyte differentiation and induction of apoptosis.
Gene Name:: NME3
Uniprot ID:: Q13232
Molecular weight:: 19014.85

Reactions

Adenosine triphosphate + CDP → ADP + Cytidine triphosphate	details

Enzyme Details

9. Nucleoside diphosphate kinase 6

General function:: Involved in nucleoside diphosphate kinase activity
Specific function:: Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-site intermediate. Inhibitor of p53-induced apoptosis.
Gene Name:: NME6
Uniprot ID:: O75414
Molecular weight:: 22002.965

Reactions

Adenosine triphosphate + CDP → ADP + Cytidine triphosphate	details

Enzyme Details

10. N-acylneuraminate cytidylyltransferase

General function:: Involved in lipopolysaccharide biosynthetic process
Specific function:: Catalyzes the activation of N-acetylneuraminic acid (NeuNAc) to cytidine 5'-monophosphate N-acetylneuraminic acid (CMP-NeuNAc), a substrate required for the addition of sialic acid. Has some activity toward NeuNAc, N-glycolylneuraminic acid (Neu5Gc) or 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN).
Gene Name:: CMAS
Uniprot ID:: Q8NFW8
Molecular weight:: 48378.835

Reactions

Cytidine triphosphate + N-acylneuraminate → Pyrophosphate + Cytidine 5'-monophosphate-N-acetylneuraminic acid	details
Cytidine triphosphate + N-Acetylneuraminic acid → Pyrophosphate + Cytidine 5'-monophosphate-N-acetylneuraminic acid	details
Cytidine triphosphate + N-Glycolylneuraminic acid → Pyrophosphate + CMP-N-glycoloylneuraminate	details

Only showing the first 10 proteins. There are 65 proteins in total.

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Showing metabocard for Cytidine triphosphate (HMDB0000082)

MOL for HMDB0000082 (Cytidine triphosphate)

3D MOL for HMDB0000082 (Cytidine triphosphate)

3D SDF for HMDB0000082 (Cytidine triphosphate)

3D-SDF for HMDB0000082 (Cytidine triphosphate)

PDB for HMDB0000082 (Cytidine triphosphate)

3D PDB for HMDB0000082 (Cytidine triphosphate)

SMILES for HMDB0000082 (Cytidine triphosphate)

INCHI for HMDB0000082 (Cytidine triphosphate)

Structure for HMDB0000082 (Cytidine triphosphate)

3D Structure for HMDB0000082 (Cytidine triphosphate)

Collision Cross Sections

Retention Indices

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