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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2019-11-25 22:07:39 UTC

Update Date

2022-03-07 03:18:20 UTC

HMDB ID

HMDB0240596

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Oleoylcholine

Description

Oleoylcholine, also known as choline oleate, belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH. Based on a literature review a small amount of articles have been published on Oleoylcholine.

Structure

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


  Mrv1652311251922562D          

 26 25  0  0  0  0            999 V2000
 9997.632310000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.347410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.062310000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.777210000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.492010000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.207110000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.922810000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.636310000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.461310000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.177010000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.892710000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.606310000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.322010000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.037710000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.751410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.467010000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.180610000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.915410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.200610000.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.485810000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.770910000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.055810000.9868    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9993.338910000.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.055810001.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.203810001.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.915410001.8113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 26  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
M  CHG  1  22   1
M  END

HMDB0240596
     RDKit          3D
Oleoylcholine
 72 71  0  0  0  0  0  0  0  0999 V2000
    9.8395   -0.5273   -0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5546   -1.7057   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -1.4753    1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2175   -1.1702    0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0078    0.0380   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5007    0.2264   -0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8021    0.4130    0.9202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891    0.6500    0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1926    1.8541   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6493    1.9082   -1.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0557    0.7351   -1.9818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5893    1.0805   -2.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    1.3428   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4770    1.6955   -0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1312    1.9663    0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0829    0.8079    1.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7389   -0.4380    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1814   -0.3164    0.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352    0.7976    0.7024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9742   -1.3370    0.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3444   -1.2423   -0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1795   -0.8482    0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5669   -0.7955    0.5214 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.6909   -0.1558   -0.7731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3465   -0.1380    1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0454   -2.1588    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5386    0.4467   -0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5043   -0.5890   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9772   -0.4201   -0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2034   -2.5614   -0.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5100   -2.1023    0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9572   -0.5834    1.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6191   -2.3540    1.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7433   -2.0323    0.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5859   -1.0585    1.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4518   -0.0786   -1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3628    0.9442    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1556   -0.6684   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4162    1.0843   -1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7888   -0.4871    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2434    1.2452    1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243   -0.2419    0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8395    0.9008    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6188    2.7951    0.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6213    2.8860   -1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4829    0.5763   -3.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0467   -0.1997   -1.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1020    0.2498   -2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834    2.0050   -2.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1520    0.4242   -0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4762    2.1797   -0.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0101    0.9249   -1.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159    2.6351   -1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    2.8023    0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1242    2.3739    0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177    0.5520    1.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5080    1.1458    2.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1709   -0.8752   -0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6432   -1.1889    1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7099   -2.1714   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4655   -0.4359   -0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1641   -1.6439    1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8769    0.1290    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7787    0.1315   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5168   -0.8725   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1143    0.7705   -0.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6934    0.3984    2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9576   -0.8440    2.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0086    0.5981    1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1534   -2.1728    0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5948   -2.8337    1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9449   -2.5535   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 22 63  1  0
 24 64  1  0
 24 65  1  0
 24 66  1  0
 25 67  1  0
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 26 72  1  0
M  CHG  1  23   1
M  END


  Mrv1652311251922562D          

 26 25  0  0  0  0            999 V2000
 9997.632310000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.347410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.062310000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.777210000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.492010000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.207110000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.922810000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.636310000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.461310000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.177010000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.892710000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.606310000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.322010000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.037710000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10007.751410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10008.467010000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.180610000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.915410000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.200610000.5751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9995.485810000.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.770910000.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.055810000.9868    0.0000 N   0  3  0  0  0  0  0  0  0  0  0  0
 9993.338910000.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.055810001.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9993.203810001.4814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.915410001.8113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 18  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  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
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 18 26  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 22 25  1  0  0  0  0
M  CHG  1  22   1
M  END
> <DATABASE_ID>
HMDB0240596

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C23H46NO2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(25)26-22-21-24(2,3)4/h12-13H,5-11,14-22H2,1-4H3/q+1/b13-12-

> <INCHI_KEY>
PVXGXBXEHLTWOE-SEYXRHQNSA-N

> <FORMULA>
C23H46NO2

> <MOLECULAR_WEIGHT>
368.625

> <EXACT_MASS>
368.352306145

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
48.714268926682635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
trimethyl({2-[(9Z)-octadec-9-enoyloxy]ethyl})azanium

> <ALOGPS_LOGP>
3.39

> <JCHEM_LOGP>
2.7860004128615885

> <ALOGPS_LOGS>
-7.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
-7.047174497735996

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
126.10399999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.38e-06 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trimethyl({2-[(9Z)-octadec-9-enoyloxy]ethyl})azanium

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0240596
     RDKit          3D
Oleoylcholine
 72 71  0  0  0  0  0  0  0  0999 V2000
    9.8395   -0.5273   -0.9011 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5546   -1.7057   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -1.4753    1.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2175   -1.1702    0.6910 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0078    0.0380   -0.1329 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5007    0.2264   -0.3721 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8021    0.4130    0.9202 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2891    0.6500    0.6869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1926    1.8541   -0.1323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6493    1.9082   -1.3162 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0557    0.7351   -1.9818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5893    1.0805   -2.2271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0115    1.3428   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4770    1.6955   -0.9936 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1312    1.9663    0.3322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0829    0.8079    1.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7389   -0.4380    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1814   -0.3164    0.5184 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7352    0.7976    0.7024 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9742   -1.3370    0.0660 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3444   -1.2423   -0.2074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1795   -0.8482    0.9712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5669   -0.7955    0.5214 N   0  0  0  0  0  4  0  0  0  0  0  0
   -8.6909   -0.1558   -0.7731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3465   -0.1380    1.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0454   -2.1588    0.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5386    0.4467   -0.4801 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5043   -0.5890   -1.9506 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9772   -0.4201   -0.9936 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2034   -2.5614   -0.7203 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5100   -2.1023    0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9572   -0.5834    1.7025 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6191   -2.3540    1.7934 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7433   -2.0323    0.0992 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5859   -1.0585    1.6221 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4518   -0.0786   -1.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3628    0.9442    0.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1556   -0.6684   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4162    1.0843   -1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7888   -0.4871    1.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2434    1.2452    1.4750 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243   -0.2419    0.2832 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8395    0.9008    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6188    2.7951    0.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6213    2.8860   -1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4829    0.5763   -3.0046 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0467   -0.1997   -1.4181 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1020    0.2498   -2.7323 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4834    2.0050   -2.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1520    0.4242   -0.2563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4762    2.1797   -0.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0101    0.9249   -1.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5159    2.6351   -1.5822 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5356    2.8023    0.8076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1242    2.3739    0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0177    0.5520    1.4982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5080    1.1458    2.2401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1709   -0.8752   -0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6432   -1.1889    1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7099   -2.1714   -0.6618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4655   -0.4359   -0.9750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1641   -1.6439    1.7666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8769    0.1290    1.3558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7787    0.1315   -0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5168   -0.8725   -1.6021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1143    0.7705   -0.8608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6934    0.3984    2.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9576   -0.8440    2.1322 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0086    0.5981    1.0632 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1534   -2.1728    0.6118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5948   -2.8337    1.1491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9449   -2.5535   -0.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  2 30  1  0
  2 31  1  0
  3 32  1  0
  3 33  1  0
  4 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  6 38  1  0
  6 39  1  0
  7 40  1  0
  7 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 10 45  1  0
 11 46  1  0
 11 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 14 52  1  0
 14 53  1  0
 15 54  1  0
 15 55  1  0
 16 56  1  0
 16 57  1  0
 17 58  1  0
 17 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 22 63  1  0
 24 64  1  0
 24 65  1  0
 24 66  1  0
 25 67  1  0
 25 68  1  0
 25 69  1  0
 26 70  1  0
 26 71  1  0
 26 72  1  0
M  CHG  1  23   1
M  END

HEADER    PROTEIN                                 25-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-NOV-19         0                                  
HETATM    1  C   UNK     0    8662.2478667.740   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8663.5828668.509   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8664.9168667.740   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8666.2518668.509   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8667.5858667.740   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8668.9208668.509   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8670.2568667.740   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8671.5888668.509   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8673.1288668.509   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8674.4648667.740   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8675.8008668.509   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8677.1328667.740   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8678.4688668.509   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8679.8048667.740   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8681.1368668.509   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8682.4728667.740   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8683.8048668.509   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8660.9098668.509   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0    8659.5748667.740   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8658.2408668.509   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8656.9068667.740   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0    8655.5718668.509   0.000  0.00  0.00           N+1
HETATM   23  C   UNK     0    8654.2338667.736   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8655.5718670.048   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8653.9808669.432   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0    8660.9098670.048   0.000  0.00  0.00           O+0
CONECT    1    2   18                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16                                                            
CONECT   18    1   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   18                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   50    0
END

COMPND    HMDB0240596
HETATM    1  C1  UNL     1       9.839  -0.527  -0.901  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.555  -1.706  -0.047  1.00  0.00           C  
HETATM    3  C3  UNL     1       8.607  -1.475   1.062  1.00  0.00           C  
HETATM    4  C4  UNL     1       7.218  -1.170   0.691  1.00  0.00           C  
HETATM    5  C5  UNL     1       7.008   0.038  -0.133  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.501   0.226  -0.372  1.00  0.00           C  
HETATM    7  C7  UNL     1       4.802   0.413   0.920  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.289   0.650   0.687  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.193   1.854  -0.132  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.649   1.908  -1.316  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.056   0.735  -1.982  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.589   1.080  -2.227  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.012   1.343  -0.844  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.477   1.695  -0.994  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.131   1.966   0.332  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.083   0.808   1.268  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.739  -0.438   0.800  1.00  0.00           C  
HETATM   18  C18 UNL     1      -4.181  -0.316   0.518  1.00  0.00           C  
HETATM   19  O1  UNL     1      -4.735   0.798   0.702  1.00  0.00           O  
HETATM   20  O2  UNL     1      -4.974  -1.337   0.066  1.00  0.00           O  
HETATM   21  C19 UNL     1      -6.344  -1.242  -0.207  1.00  0.00           C  
HETATM   22  C20 UNL     1      -7.179  -0.848   0.971  1.00  0.00           C  
HETATM   23  N1  UNL     1      -8.567  -0.796   0.521  1.00  0.00           N1+
HETATM   24  C21 UNL     1      -8.691  -0.156  -0.773  1.00  0.00           C  
HETATM   25  C22 UNL     1      -9.347  -0.138   1.538  1.00  0.00           C  
HETATM   26  C23 UNL     1      -9.045  -2.159   0.395  1.00  0.00           C  
HETATM   27  H1  UNL     1       9.539   0.447  -0.480  1.00  0.00           H  
HETATM   28  H2  UNL     1       9.504  -0.589  -1.951  1.00  0.00           H  
HETATM   29  H3  UNL     1      10.977  -0.420  -0.994  1.00  0.00           H  
HETATM   30  H4  UNL     1       9.203  -2.561  -0.720  1.00  0.00           H  
HETATM   31  H5  UNL     1      10.510  -2.102   0.428  1.00  0.00           H  
HETATM   32  H6  UNL     1       8.957  -0.583   1.703  1.00  0.00           H  
HETATM   33  H7  UNL     1       8.619  -2.354   1.793  1.00  0.00           H  
HETATM   34  H8  UNL     1       6.743  -2.032   0.099  1.00  0.00           H  
HETATM   35  H9  UNL     1       6.586  -1.058   1.622  1.00  0.00           H  
HETATM   36  H10 UNL     1       7.452  -0.079  -1.178  1.00  0.00           H  
HETATM   37  H11 UNL     1       7.363   0.944   0.366  1.00  0.00           H  
HETATM   38  H12 UNL     1       5.156  -0.668  -0.940  1.00  0.00           H  
HETATM   39  H13 UNL     1       5.416   1.084  -1.061  1.00  0.00           H  
HETATM   40  H14 UNL     1       4.789  -0.487   1.588  1.00  0.00           H  
HETATM   41  H15 UNL     1       5.243   1.245   1.475  1.00  0.00           H  
HETATM   42  H16 UNL     1       2.824  -0.242   0.283  1.00  0.00           H  
HETATM   43  H17 UNL     1       2.839   0.901   1.694  1.00  0.00           H  
HETATM   44  H18 UNL     1       3.619   2.795   0.295  1.00  0.00           H  
HETATM   45  H19 UNL     1       2.621   2.886  -1.873  1.00  0.00           H  
HETATM   46  H20 UNL     1       2.483   0.576  -3.005  1.00  0.00           H  
HETATM   47  H21 UNL     1       2.047  -0.200  -1.418  1.00  0.00           H  
HETATM   48  H22 UNL     1       0.102   0.250  -2.732  1.00  0.00           H  
HETATM   49  H23 UNL     1       0.483   2.005  -2.831  1.00  0.00           H  
HETATM   50  H24 UNL     1       0.152   0.424  -0.256  1.00  0.00           H  
HETATM   51  H25 UNL     1       0.476   2.180  -0.343  1.00  0.00           H  
HETATM   52  H26 UNL     1      -2.010   0.925  -1.571  1.00  0.00           H  
HETATM   53  H27 UNL     1      -1.516   2.635  -1.582  1.00  0.00           H  
HETATM   54  H28 UNL     1      -1.536   2.802   0.808  1.00  0.00           H  
HETATM   55  H29 UNL     1      -3.124   2.374   0.159  1.00  0.00           H  
HETATM   56  H30 UNL     1      -1.018   0.552   1.498  1.00  0.00           H  
HETATM   57  H31 UNL     1      -2.508   1.146   2.240  1.00  0.00           H  
HETATM   58  H32 UNL     1      -2.171  -0.875  -0.047  1.00  0.00           H  
HETATM   59  H33 UNL     1      -2.643  -1.189   1.631  1.00  0.00           H  
HETATM   60  H34 UNL     1      -6.710  -2.171  -0.662  1.00  0.00           H  
HETATM   61  H35 UNL     1      -6.466  -0.436  -0.975  1.00  0.00           H  
HETATM   62  H36 UNL     1      -7.164  -1.644   1.767  1.00  0.00           H  
HETATM   63  H37 UNL     1      -6.877   0.129   1.356  1.00  0.00           H  
HETATM   64  H38 UNL     1      -9.779   0.132  -0.868  1.00  0.00           H  
HETATM   65  H39 UNL     1      -8.517  -0.873  -1.602  1.00  0.00           H  
HETATM   66  H40 UNL     1      -8.114   0.771  -0.861  1.00  0.00           H  
HETATM   67  H41 UNL     1      -8.693   0.398   2.281  1.00  0.00           H  
HETATM   68  H42 UNL     1      -9.958  -0.844   2.132  1.00  0.00           H  
HETATM   69  H43 UNL     1     -10.009   0.598   1.063  1.00  0.00           H  
HETATM   70  H44 UNL     1     -10.153  -2.173   0.612  1.00  0.00           H  
HETATM   71  H45 UNL     1      -8.595  -2.834   1.149  1.00  0.00           H  
HETATM   72  H46 UNL     1      -8.945  -2.553  -0.637  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3   30   31
CONECT    3    4   32   33
CONECT    4    5   34   35
CONECT    5    6   36   37
CONECT    6    7   38   39
CONECT    7    8   40   41
CONECT    8    9   42   43
CONECT    9   10   10   44
CONECT   10   11   45
CONECT   11   12   46   47
CONECT   12   13   48   49
CONECT   13   14   50   51
CONECT   14   15   52   53
CONECT   15   16   54   55
CONECT   16   17   56   57
CONECT   17   18   58   59
CONECT   18   19   19   20
CONECT   20   21
CONECT   21   22   60   61
CONECT   22   23   62   63
CONECT   23   24   25   26
CONECT   24   64   65   66
CONECT   25   67   68   69
CONECT   26   70   71   72
END

HMDB0240596
     RDKit          3D
Oleoylcholine
 72 71  0  0  0  0  0  0  0  0999 V2000
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  1  2  1  0
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 26 72  1  0
M  CHG  1  23   1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9Z)-Octadecenoylcholine	ChEBI
Choline (9Z)-octadecenoate	ChEBI
Choline oleate	ChEBI
Choline (9Z)-octadecenoic acid	Generator
Choline oleic acid	Generator
Oleoylcholine	HMDB

Chemical Formula

C₂₃H₄₆NO₂

Average Molecular Weight

368.625

Monoisotopic Molecular Weight

368.352306145

IUPAC Name

trimethyl({2-[(9Z)-octadec-9-enoyloxy]ethyl})azanium

Traditional Name

trimethyl({2-[(9Z)-octadec-9-enoyloxy]ethyl})azanium

CAS Registry Number

127165-03-1

SMILES

CCCCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C23H46NO2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(25)26-22-21-24(2,3)4/h12-13H,5-11,14-22H2,1-4H3/q+1/b13-12-

InChI Key

PVXGXBXEHLTWOE-SEYXRHQNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Acyl cholines

Alternative Parents

Substituents

Acyl choline
Fatty acid ester
Fatty acyl
Tetraalkylammonium salt
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Amine
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.39	ALOGPS
logP	2.79	ChemAxon
logS	-7.8	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	126.1 m³·mol⁻¹	ChemAxon
Polarizability	48.71 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	200.407	30932474
DeepCCS	[M-H]-	197.857	30932474
DeepCCS	[M-2H]-	231.163	30932474
DeepCCS	[M+Na]+	207.794	30932474

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oleoylcholine	CCCCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C	2792.9	Standard polar	33892256
Oleoylcholine	CCCCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C	2303.9	Standard non polar	33892256
Oleoylcholine	CCCCCCCC\C=C/CCCCCCCC(=O)OCC[N+](C)(C)C	2534.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Oleoylcholine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Placenta

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	31396400	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58827254

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

59040790

PDB ID

Not Available

ChEBI ID

133693

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Zarei I, Oppel RC, Borresen EC, Brown RJ, Ryan EP: Modulation of plasma and urine metabolome in colorectal cancer survivors consuming rice bran. Integr Food Nutr Metab. 2019 May;6(3). doi: 10.15761/IFNM.1000252. Epub 2019 Apr 5. [PubMed:31396400 ]

Showing metabocard for Oleoylcholine (HMDB0240596)

MOL for HMDB0240596 (Oleoylcholine)

3D MOL for HMDB0240596 (Oleoylcholine)

3D SDF for HMDB0240596 (Oleoylcholine)

3D-SDF for HMDB0240596 (Oleoylcholine)

PDB for HMDB0240596 (Oleoylcholine)

3D PDB for HMDB0240596 (Oleoylcholine)

SMILES for HMDB0240596 (Oleoylcholine)

INCHI for HMDB0240596 (Oleoylcholine)

Structure for HMDB0240596 (Oleoylcholine)

3D Structure for HMDB0240596 (Oleoylcholine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra