NP-MRD: Showing NP-Card for gamma-Linolenoyl-CoA (NP0044528)

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Record Information

Version

2.0

Created at

2022-02-14 20:58:19 UTC

Updated at

2022-03-10 22:21:56 UTC

NP-MRD ID

NP0044528

Secondary Accession Numbers

None

Natural Product Identification

Common Name

gamma-Linolenoyl-CoA

Description

Gamma-linolenoyl-CoA, also known as gamolenoyl-CoA or gla-CoA, belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms. Thus, Gamma-linolenoyl-CoA is considered to be a fatty ester lipid molecule. Gamma-linolenoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Gamma-Linolenoyl-CoA is expected to be in Cannabis as all living plants are known to produce and metabolize it.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309042000322D          

 67 69  0  0  1  0            999 V2000
   18.9722   -5.2752    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6960   -4.9439    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    8.2702   -5.9666    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.6914   -5.8198    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -7.4223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1429   -5.5560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0854   -7.0061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6019   -6.4504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2491   -4.3318    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0838   -4.3908    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9383   -5.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3080   -5.4970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3690   -6.6762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4446   -6.1566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7864   -5.2984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7037   -7.1671    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0283   -5.0667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6982   -6.5729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2023   -5.0422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0449   -4.7484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8102   -6.4327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1379   -8.4600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1379   -9.7876    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6428   -8.2988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9284   -9.5364    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6428  -10.7738    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0402   -6.1997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8827   -5.9058    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3964   -6.3410    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9103   -7.0075    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1806   -6.5973    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.3941   -7.6759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.8488   -6.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3573   -8.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6193   -9.1239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3573   -9.5364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6428   -9.9488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8658   -6.0097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1127   -5.6729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6188   -6.3465    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9284   -8.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5289   -6.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2026   -5.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2870   -5.8629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7084   -5.7159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4614   -6.0528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1296   -5.5690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5510   -5.4222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3040   -5.7590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1466   -5.4651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2315   -6.2858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3936   -5.1284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5729   -3.8666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8197   -3.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9846   -6.6227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7253   -5.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6578   -4.6873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7349   -2.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0695   -7.4433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4110   -5.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9817   -2.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8227   -7.7802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4910   -7.2963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4958   -5.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8276   -6.3286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2441   -7.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9124   -7.1493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 49  1  0  0  0  0
  1 56  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2 12  2  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  3 13  1  0  0  0  0
  3 15  2  0  0  0  0
  4 11  1  0  0  0  0
  4 14  1  0  0  0  0
  4 17  1  0  0  0  0
  4 18  2  0  0  0  0
  5 31  1  0  0  0  0
  5 32  1  0  0  0  0
 29  6  1  6  0  0  0
 30  7  1  6  0  0  0
  8 33  1  0  0  0  0
 14 39  1  0  0  0  0
 40 16  1  6  0  0  0
 19 44  2  0  0  0  0
 20 47  2  0  0  0  0
 21 56  2  0  0  0  0
 32 22  1  1  0  0  0
 22 34  1  0  0  0  0
 22 35  1  0  0  0  0
 23 35  2  0  0  0  0
 23 36  1  0  0  0  0
 24 34  2  0  0  0  0
 24 41  1  0  0  0  0
 25 37  1  0  0  0  0
 25 41  2  0  0  0  0
 26 37  1  0  0  0  0
 27 44  1  0  0  0  0
 27 45  1  0  0  0  0
 28 47  1  0  0  0  0
 28 48  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  1  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 38 42  1  0  0  0  0
 38 43  1  0  0  0  0
 40 44  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 48 49  1  0  0  0  0
 50 51  1  0  0  0  0
 50 52  1  0  0  0  0
 51 55  1  0  0  0  0
 52 56  1  0  0  0  0
 53 54  1  0  0  0  0
 53 57  1  0  0  0  0
 54 58  1  0  0  0  0
 55 59  1  0  0  0  0
 57 60  1  0  0  0  0
 58 61  1  0  0  0  0
 59 62  2  0  0  0  0
 60 64  2  0  0  0  0
 62 63  1  0  0  0  0
 63 66  1  0  0  0  0
 64 65  1  0  0  0  0
 65 67  1  0  0  0  0
 66 67  2  0  0  0  0
M  END

     RDKit          3D

131133  0  0  0  0  0  0  0  0999 V2000
   12.1022    2.5615    0.9253 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9657    3.3119   -0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2153    2.6909   -0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1117    1.4493   -1.2901 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5673    0.2311   -0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4470   -0.1298    0.5239 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0491   -1.2717    0.6112 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0020   -2.4103   -0.3331 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5378   -3.5757    0.4278 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5067   -4.3011    0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4693   -4.2547   -0.7757 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3922   -3.3007   -1.8365 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3546   -2.4342   -1.9638 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2540   -2.4424   -0.9901 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9120   -2.8258   -1.5935 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8896   -2.8219   -0.5032 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6558   -1.4604    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8762   -0.0430   -1.6895 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3622   -0.0887   -0.8263 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -0.6600    0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1221    0.2607    1.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5492    1.5974    1.5753 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1103    1.6427    1.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4388    0.6673    2.0645 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4159    2.9358    1.4526 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0008    2.8323    1.9126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2115    1.8029    1.3078 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1412    1.6023    1.6945 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9406    0.5441    1.0934 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1701   -0.0792    0.0899 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2482    0.9441    0.4957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.9312   -0.2920   -0.0708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0817    1.9070   -0.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2075    1.5476    1.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3899    1.8651    0.7961 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5093    2.5593    1.8956 P   0  0  1  0  0  5  0  0  0  0  0  0
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  -17.7137   -3.1557    0.7608 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -16.2171   -1.3717    0.4799 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.6229   -0.9997   -2.7845 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5097    0.1997   -3.9769 P   0  0  1  0  0  5  0  0  0  0  0  0
  -10.1363    0.8654   -3.9416 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8269   -0.4157   -5.5043 O   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3002    3.6187   -0.8833 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2527    4.3114    0.4627 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8349    3.4661   -1.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
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   12.5330    0.3951   -0.2660 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.4620   -0.6095   -1.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
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   16.0956   -2.5735   -0.6396 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.4836   -2.1634   -1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2095   -3.8317    1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.3928   -5.1549    0.9937 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4682   -4.4325   -0.2535 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.5529   -5.3062   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.1635   -3.2490   -2.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.3872   -1.7415   -2.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1068   -1.3209   -0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4191   -2.8903   -0.0295 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

  Mrv1652309042000322D          

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M  END
> <DATABASE_ID>
NP0044528

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C39H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,14-15,26-28,32-34,38,49-50H,4-7,10,13,16-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8-,12-11-,15-14-/t28-,32-,33-,34+,38-/m1/s1

> <INCHI_KEY>
XZQYPTBYQYZGRU-FHDVEODPSA-N

> <FORMULA>
C39H64N7O17P3S

> <MOLECULAR_WEIGHT>
1027.948

> <EXACT_MASS>
1027.329223883

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
131

> <JCHEM_AVERAGE_POLARIZABILITY>
100.2041225943841

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
2.86

> <JCHEM_LOGP>
0.40168173885203723

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776185

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398193

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
363.6299999999998

> <JCHEM_REFRACTIVITY>
249.19970000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
33

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.36e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
gamma-linolenoyl-coa

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  S   UNK     0      35.415  -9.847   0.000  0.00  0.00           S+0
HETATM    2  P   UNK     0      10.633  -9.229   0.000  0.00  0.00           P+0
HETATM    3  P   UNK     0      15.438 -11.138   0.000  0.00  0.00           P+0
HETATM    4  P   UNK     0      18.091 -10.864   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0      11.535 -13.855   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       9.600 -10.371   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       7.626 -13.078   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      14.190 -12.041   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      11.665  -8.086   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       9.490  -8.196   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      16.685 -10.235   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      11.775 -10.261   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      15.622 -12.462   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      19.497 -11.492   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      14.535  -9.890   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      23.714 -13.379   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      18.719  -9.458   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      18.103 -12.269   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      24.644  -9.412   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      29.950  -8.864   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      36.979 -12.008   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0       9.591 -15.792   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0       9.591 -18.270   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0       6.800 -15.491   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0       5.466 -17.801   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0       6.800 -20.111   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      26.208 -11.573   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      31.514 -11.024   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      10.073 -11.837   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.166 -13.081   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.537 -12.315   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      10.069 -14.328   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      12.784 -11.412   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.134 -16.261   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.489 -17.031   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       8.134 -17.801   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       6.800 -18.571   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      22.149 -11.218   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      20.744 -10.589   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      23.555 -11.847   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       5.466 -16.261   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      21.521 -12.624   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      22.778  -9.812   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      24.802 -10.944   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      27.456 -10.670   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      28.861 -11.299   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      30.109 -10.395   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      32.762 -10.121   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      34.167 -10.750   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      39.474 -10.202   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      39.632 -11.733   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      38.068  -9.573   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      45.869  -7.218   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      44.463  -6.589   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      41.038 -12.362   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      36.821 -10.476   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      46.028  -8.750   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      44.305  -5.057   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      41.196 -13.894   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      47.434  -9.378   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      42.899  -4.428   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      42.602 -14.523   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      43.850 -13.620   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      47.592 -10.910   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      46.345 -11.813   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      45.256 -14.249   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0      46.503 -13.345   0.000  0.00  0.00           C+0
CONECT    1   49   56                                                       
CONECT    2    6    9   10   12                                             
CONECT    3    8   11   13   15                                             
CONECT    4   11   14   17   18                                             
CONECT    5   31   32                                                       
CONECT    6    2   29                                                       
CONECT    7   30                                                            
CONECT    8    3   33                                                       
CONECT    9    2                                                            
CONECT   10    2                                                            
CONECT   11    3    4                                                       
CONECT   12    2                                                            
CONECT   13    3                                                            
CONECT   14    4   39                                                       
CONECT   15    3                                                            
CONECT   16   40                                                            
CONECT   17    4                                                            
CONECT   18    4                                                            
CONECT   19   44                                                            
CONECT   20   47                                                            
CONECT   21   56                                                            
CONECT   22   32   34   35                                                  
CONECT   23   35   36                                                       
CONECT   24   34   41                                                       
CONECT   25   37   41                                                       
CONECT   26   37                                                            
CONECT   27   44   45                                                       
CONECT   28   47   48                                                       
CONECT   29    6   30   31                                                  
CONECT   30    7   29   32                                                  
CONECT   31    5   29   33                                                  
CONECT   32    5   22   30                                                  
CONECT   33    8   31                                                       
CONECT   34   22   24   36                                                  
CONECT   35   22   23                                                       
CONECT   36   23   34   37                                                  
CONECT   37   25   26   36                                                  
CONECT   38   39   40   42   43                                             
CONECT   39   14   38                                                       
CONECT   40   16   38   44                                                  
CONECT   41   24   25                                                       
CONECT   42   38                                                            
CONECT   43   38                                                            
CONECT   44   19   27   40                                                  
CONECT   45   27   46                                                       
CONECT   46   45   47                                                       
CONECT   47   20   28   46                                                  
CONECT   48   28   49                                                       
CONECT   49    1   48                                                       
CONECT   50   51   52                                                       
CONECT   51   50   55                                                       
CONECT   52   50   56                                                       
CONECT   53   54   57                                                       
CONECT   54   53   58                                                       
CONECT   55   51   59                                                       
CONECT   56    1   21   52                                                  
CONECT   57   53   60                                                       
CONECT   58   54   61                                                       
CONECT   59   55   62                                                       
CONECT   60   57   64                                                       
CONECT   61   58                                                            
CONECT   62   59   63                                                       
CONECT   63   62   66                                                       
CONECT   64   60   65                                                       
CONECT   65   64   67                                                       
CONECT   66   63   67                                                       
CONECT   67   65   66                                                       
MASTER        0    0    0    0    0    0    0    0   67    0  138    0
END

View in JSmol

Synonyms

Value	Source
(6Z,9Z,12Z)-6,9,12-Octadecatrienoyl-CoA	ChEBI
(Z,Z,Z)-6,9,12-Octadecatrienoyl-CoA	ChEBI
(Z,Z,Z)-6,9,12-Octadecatrienoyl-coenzyme A	ChEBI
6-cis,9-cis,12-cis-Octadecatrienoyl-CoA	ChEBI
6-cis,9-cis,12-cis-Octadecatrienoyl-coenzyme A	ChEBI
gamma-Linolenoyl-coenzyme A	ChEBI
Gamolenoyl-CoA	ChEBI
GLA-CoA	ChEBI
g-Linolenoyl-coenzyme A	Generator
Γ-linolenoyl-coenzyme A	Generator
g-Linolenoyl-CoA	Generator
Γ-linolenoyl-CoA	Generator

Chemical Formula

C₃₉H₆₄N₇O₁₇P₃S

Average Mass

1027.9480 Da

Monoisotopic Mass

1027.32922 Da

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(6Z,9Z,12Z)-octadeca-6,9,12-trienoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

gamma-linolenoyl-coa

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/C\C=C/CCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12

InChI Identifier

InChI=1S/C39H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h8-9,11-12,14-15,26-28,32-34,38,49-50H,4-7,10,13,16-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b9-8-,12-11-,15-14-/t28-,32-,33-,34+,38-/m1/s1

InChI Key

XZQYPTBYQYZGRU-FHDVEODPSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a long aliphatic chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-chain fatty acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

unsaturated fatty acyl-CoA (CHEBI:15508 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	2.86	ALOGPS
logP	0.4	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	33	ChemAxon
Refractivity	249.2 m³·mol⁻¹	ChemAxon
Polarizability	100.2 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0006368

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023905

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11966132

PDB ID

Not Available

ChEBI ID

15508

Good Scents ID

Not Available

References

General References

Mimouni V, Narce M, Poisson JP: Evidence for insulin dependent hepatic microsomal gamma-linolenic acid chain elongation in spontaneously diabetic Wistar BB rats. Biochim Biophys Acta. 1992 Jan 13;1133(2):187-92. doi: 10.1016/0167-4889(92)90068-m. [PubMed:1310052 ]
Suneja SK, Osei P, Cook L, Nagi MN, Cinti DL: Enzyme site-specific changes in hepatic microsomal fatty acid chain elongation in streptozotocin-induced diabetic rats. Biochim Biophys Acta. 1990 Jan 16;1042(1):81-5. doi: 10.1016/0005-2760(90)90059-7. [PubMed:2297524 ]
Prasad MR, Nagi MN, Ghesquier D, Cook L, Cinti DL: Evidence for multiple condensing enzymes in rat hepatic microsomes catalyzing the condensation of saturated, monounsaturated, and polyunsaturated acyl coenzyme A. J Biol Chem. 1986 Jun 25;261(18):8213-7. [PubMed:3722151 ]

Showing NP-Card for gamma-Linolenoyl-CoA (NP0044528)

MOL for NP0044528 (gamma-Linolenoyl-CoA)

3D MOL for NP0044528 (gamma-Linolenoyl-CoA)

3D SDF for NP0044528 (gamma-Linolenoyl-CoA)

3D-SDF for NP0044528 (gamma-Linolenoyl-CoA)

PDB for NP0044528 (gamma-Linolenoyl-CoA)

3D PDB for NP0044528 (gamma-Linolenoyl-CoA)

SMILES for NP0044528 (gamma-Linolenoyl-CoA)

INCHI for NP0044528 (gamma-Linolenoyl-CoA)

Structure for NP0044528 (gamma-Linolenoyl-CoA)

3D Structure for NP0044528 (gamma-Linolenoyl-CoA)