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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (111)transporters (1) Show 112 proteins XML

enzymes (111)transporters (1) Show 112 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 15:12:14 UTC

Update Date

2021-09-14 15:00:02 UTC

HMDB ID

HMDB0002845

Secondary Accession Numbers

HMDB02845

Metabolite Identification

Common Name

Hexanoyl-CoA

Description

Hexanoyl-CoA, also known as hexanoyl-coenzyme A or caproyl-CoA, is a medium-chain fatty acyl-CoA having hexanoyl as the acyl group. Hexanoyl-CoA is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Within the cell, hexanoyl-CoA is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. Hexanoyl-CoA exists in all living organisms, ranging from bacteria to humans. In humans, hexanoyl-CoA is involved in the biosynthesis and oxidation of fatty acids as well as in ceramide formation. Hexanoyl-CoA is also involved in few metabolic disorders, such as fatty acid elongation in mitochondria, mitochondrial beta-oxidation of medium chain saturated fatty acids, and mitochondrial beta-oxidation of short chain saturated fatty acids.

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI

ChEBI
  Mrv1652305151820132D          

 55 57  0  0  1  0            999 V2000
   28.6532   -2.8824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.9858   -2.3975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3983   -3.6670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.3183   -2.8824    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.5733   -3.6670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.8832   -4.3345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9075   -6.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6503   -7.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1930   -7.3359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4785   -6.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7641   -7.3359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2214   -5.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4785   -6.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2214   -4.8609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7925   -4.8609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5069   -4.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9359   -3.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8089   -2.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2214   -3.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6339   -2.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5069   -3.6233    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.7924   -3.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6503   -3.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3003   -3.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9503   -3.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4753   -2.3857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4753   -4.0358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1253   -2.3857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1253   -4.0358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4753   -3.2108    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.1253   -3.2108    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.5337   -2.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0883   -4.3345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2633   -5.1595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9133   -5.1595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0883   -5.1595    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.0883   -5.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4378   -2.6275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0510   -3.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7733   -1.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7654   -2.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0510   -4.0045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5939   -1.9600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4799   -3.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7655   -4.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4799   -4.0044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3647   -6.9234    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.0793   -8.1609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0793   -7.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7938   -6.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5082   -7.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2227   -6.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9372   -7.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6517   -6.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1943   -2.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 47  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 46 45  1  0  0  0  0
 47 49  1  0  0  0  0
 49 48  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 44 55  1  0  0  0  0
M  END

ChEBI
  Mrv1652305151820132D          

 55 57  0  0  1  0            999 V2000
   28.6532   -2.8824    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   27.9858   -2.3975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3983   -3.6670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.3183   -2.8824    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   27.5733   -3.6670    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   28.8832   -4.3345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9075   -6.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6503   -7.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1930   -7.3359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4785   -6.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7641   -7.3359    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2214   -5.6859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4785   -6.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2214   -4.8609    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7925   -4.8609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5069   -4.4483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9359   -3.6233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8089   -2.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2214   -3.2108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6339   -2.4964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5069   -3.6233    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   19.7924   -3.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6503   -3.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3003   -3.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.9503   -3.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4753   -2.3857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4753   -4.0358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1253   -2.3857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1253   -4.0358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.4753   -3.2108    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.1253   -3.2108    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.5337   -2.6275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0883   -4.3345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2633   -5.1595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9133   -5.1595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.0883   -5.1595    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.0883   -5.9845    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4378   -2.6275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0510   -3.1795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7733   -1.8738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7654   -2.7670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0510   -4.0045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.5939   -1.9600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4799   -3.1793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7655   -4.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4799   -4.0044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3647   -6.9234    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.0793   -8.1609    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0793   -7.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7938   -6.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5082   -7.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2227   -6.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9372   -7.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6517   -6.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1943   -2.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 47  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 46 45  1  0  0  0  0
 47 49  1  0  0  0  0
 49 48  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 44 55  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002845

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC(=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=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C27H46N7O17P3S/c1-4-5-6-7-18(36)55-11-10-29-17(35)8-9-30-25(39)22(38)27(2,3)13-48-54(45,46)51-53(43,44)47-12-16-21(50-52(40,41)42)20(37)26(49-16)34-15-33-19-23(28)31-14-32-24(19)34/h14-16,20-22,26,37-38H,4-13H2,1-3H3,(H,29,35)(H,30,39)(H,43,44)(H,45,46)(H2,28,31,32)(H2,40,41,42)/t16-,20-,21-,22+,26-/m1/s1

> <INCHI_KEY>
OEXFMSFODMQEPE-HDRQGHTBSA-N

> <FORMULA>
C27H46N7O17P3S

> <MOLECULAR_WEIGHT>
865.677

> <EXACT_MASS>
865.188373307

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
101

> <JCHEM_AVERAGE_POLARIZABILITY>
80.880242118784

> <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)-2-({[({[(3R)-3-[(2-{[2-(hexanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
0.07

> <JCHEM_LOGP>
-3.8473772711479604

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.9001207347761846

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398228

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
363.6299999999999

> <JCHEM_REFRACTIVITY>
190.6379

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hexanoyl-coa

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/CCCCCC(=O)SCCNC(=O)CCNC(=O)%5BC...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:100})
101103  0  0  0  0  0  0  0  0999 V2000
  -19.1698    4.9856    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.9226    4.2039    1.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.1076    3.8420   -0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.8604    3.0603    0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0454    2.6984   -0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8170    1.9284   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.7832   -2.7669    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5975   -3.2627   -1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2647   -3.0017   -1.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0041   -4.6019   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5887   -2.0208    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741   -1.4361    0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9001   -1.6990   -0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840   -3.9748    2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948   -5.0450    0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4600   -1.1357    3.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9475   -0.8363    1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.7356    3.1065   -1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2930   -2.9176   -2.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5525   -1.8020   -4.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4200    2.6712    2.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
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 60101  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 15-MAY-18   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-18         0                                  
HETATM    1  C   UNK     0      53.486  -5.380   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      52.240  -4.475   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      53.010  -6.845   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      50.994  -5.380   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      51.470  -6.845   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      53.915  -8.091   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      40.894 -12.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      42.281 -13.694   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      39.560 -13.694   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      38.227 -12.924   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      36.893 -13.694   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      39.613 -10.614   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      38.227 -11.384   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      39.613  -9.074   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      36.946  -9.074   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      38.280  -8.303   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      40.947  -6.763   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.843  -4.660   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      39.613  -5.993   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      40.383  -4.660   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      38.280  -6.763   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      36.946  -5.993   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      42.281  -5.993   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      45.361  -5.993   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      48.441  -5.993   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      43.821  -4.453   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      43.821  -7.533   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      46.901  -4.453   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      46.901  -7.533   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      43.821  -5.993   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      46.901  -5.993   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      49.530  -4.905   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      50.565  -8.091   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      49.025  -9.631   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      52.105  -9.631   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      50.565  -9.631   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      50.565 -11.171   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      54.951  -4.905   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      56.095  -5.935   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      55.577  -3.498   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      57.429  -5.165   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      56.095  -7.475   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      57.109  -3.659   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      58.762  -5.935   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      57.429  -8.245   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      58.762  -7.475   0.000  0.00  0.00           N+0
HETATM   47  S   UNK     0      43.614 -12.924   0.000  0.00  0.00           S+0
HETATM   48  O   UNK     0      44.948 -15.234   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      44.948 -13.694   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      46.282 -12.924   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      47.615 -13.694   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      48.949 -12.924   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      50.283 -13.694   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      51.617 -12.924   0.000  0.00  0.00           C+0
HETATM   55  N   UNK     0      60.096  -5.165   0.000  0.00  0.00           N+0
CONECT    1   38    2    3                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2   32    5                                                  
CONECT    5    3    4   33                                                  
CONECT    6    3                                                            
CONECT    7    9    8                                                       
CONECT    8    7   47                                                       
CONECT    9    7   10                                                       
CONECT   10    9   13   11                                                  
CONECT   11   10                                                            
CONECT   12   14   13                                                       
CONECT   13   10   12                                                       
CONECT   14   12   16                                                       
CONECT   15   16                                                            
CONECT   16   14   15   21                                                  
CONECT   17   19   23                                                       
CONECT   18   19                                                            
CONECT   19   17   18   21   20                                             
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21                                                            
CONECT   23   17   30                                                       
CONECT   24   30   31                                                       
CONECT   25   31   32                                                       
CONECT   26   30                                                            
CONECT   27   30                                                            
CONECT   28   31                                                            
CONECT   29   31                                                            
CONECT   30   23   24   26   27                                             
CONECT   31   24   25   28   29                                             
CONECT   32    4   25                                                       
CONECT   33    5   36                                                       
CONECT   34   36                                                            
CONECT   35   36                                                            
CONECT   36   33   34   35   37                                             
CONECT   37   36                                                            
CONECT   38    1   39   40                                                  
CONECT   39   38   41   42                                                  
CONECT   40   38   43                                                       
CONECT   41   39   44   43                                                  
CONECT   42   39   45                                                       
CONECT   43   40   41                                                       
CONECT   44   41   46   55                                                  
CONECT   45   42   46                                                       
CONECT   46   44   45                                                       
CONECT   47    8   49                                                       
CONECT   48   49                                                            
CONECT   49   47   48   50                                                  
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53                                                            
CONECT   55   44                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/CCCCCC(=O)SCCNC(=O)CCNC(=O)%5BC... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1     -19.170   4.986   0.824  1.00  0.00           C  
HETATM    2  C   UNL     1     -17.923   4.204   1.241  1.00  0.00           C  
HETATM    3  C   UNL     1     -17.108   3.842  -0.002  1.00  0.00           C  
HETATM    4  C   UNL     1     -15.860   3.060   0.415  1.00  0.00           C  
HETATM    5  C   UNL     1     -15.045   2.698  -0.828  1.00  0.00           C  
HETATM    6  C   UNL     1     -13.817   1.928  -0.417  1.00  0.00           C  
HETATM    7  O   UNL     1     -13.613   1.692   0.756  1.00  0.00           O  
HETATM    8  S   UNL     1     -12.709   1.387  -1.604  1.00  0.00           S  
HETATM    9  C   UNL     1     -11.494   0.561  -0.547  1.00  0.00           C  
HETATM   10  C   UNL     1     -10.374  -0.018  -1.413  1.00  0.00           C  
HETATM   11  N   UNL     1      -9.390  -0.687  -0.557  1.00  0.00           N  
HETATM   12  C   UNL     1      -8.309  -1.275  -1.106  1.00  0.00           C  
HETATM   13  O   UNL     1      -8.150  -1.251  -2.308  1.00  0.00           O  
HETATM   14  C   UNL     1      -7.297  -1.962  -0.226  1.00  0.00           C  
HETATM   15  C   UNL     1      -6.178  -2.542  -1.092  1.00  0.00           C  
HETATM   16  N   UNL     1      -5.194  -3.211  -0.236  1.00  0.00           N  
HETATM   17  C   UNL     1      -4.113  -3.799  -0.785  1.00  0.00           C  
HETATM   18  O   UNL     1      -4.000  -3.857  -1.991  1.00  0.00           O  
HETATM   19  C   UNL     1      -3.043  -4.385   0.101  1.00  0.00           C  
HETATM   20  H   UNL     1      -2.799  -5.390  -0.242  1.00  0.00           H  
HETATM   21  O   UNL     1      -3.518  -4.442   1.447  1.00  0.00           O  
HETATM   22  C   UNL     1      -1.792  -3.507   0.039  1.00  0.00           C  
HETATM   23  C   UNL     1      -1.198  -3.564  -1.370  1.00  0.00           C  
HETATM   24  C   UNL     1      -2.166  -2.062   0.376  1.00  0.00           C  
HETATM   25  C   UNL     1      -0.761  -4.016   1.048  1.00  0.00           C  
HETATM   26  O   UNL     1       0.408  -3.196   0.990  1.00  0.00           O  
HETATM   27  P   UNL     1       1.700  -3.443   1.918  1.00  0.00           P  
HETATM   28  O   UNL     1       1.306  -3.201   3.461  1.00  0.00           O  
HETATM   29  O   UNL     1       2.175  -4.833   1.742  1.00  0.00           O  
HETATM   30  O   UNL     1       2.868  -2.419   1.496  1.00  0.00           O  
HETATM   31  P   UNL     1       4.464  -2.394   1.708  1.00  0.00           P  
HETATM   32  O   UNL     1       4.797  -2.002   3.233  1.00  0.00           O  
HETATM   33  O   UNL     1       5.022  -3.732   1.409  1.00  0.00           O  
HETATM   34  O   UNL     1       5.120  -1.306   0.719  1.00  0.00           O  
HETATM   35  C   UNL     1       6.531  -1.119   0.593  1.00  0.00           C  
HETATM   36  C   UNL     1       6.810  -0.012  -0.426  1.00  0.00           C  
HETATM   37  H   UNL     1       6.311  -0.241  -1.367  1.00  0.00           H  
HETATM   38  O   UNL     1       6.343   1.249   0.082  1.00  0.00           O  
HETATM   39  C   UNL     1       7.253   2.261  -0.400  1.00  0.00           C  
HETATM   40  H   UNL     1       7.039   2.505  -1.440  1.00  0.00           H  
HETATM   41  C   UNL     1       8.643   1.587  -0.273  1.00  0.00           C  
HETATM   42  H   UNL     1       9.015   1.653   0.750  1.00  0.00           H  
HETATM   43  O   UNL     1       9.575   2.164  -1.190  1.00  0.00           O  
HETATM   44  C   UNL     1       8.328   0.117  -0.656  1.00  0.00           C  
HETATM   45  H   UNL     1       8.872  -0.571  -0.009  1.00  0.00           H  
HETATM   46  O   UNL     1       8.655  -0.123  -2.026  1.00  0.00           O  
HETATM   47  P   UNL     1       9.709  -1.248  -2.492  1.00  0.00           P  
HETATM   48  O   UNL     1       9.139  -2.706  -2.115  1.00  0.00           O  
HETATM   49  O   UNL     1       9.928  -1.152  -4.084  1.00  0.00           O  
HETATM   50  O   UNL     1      11.000  -1.030  -1.802  1.00  0.00           O  
HETATM   51  N   UNL     1       7.179   3.461   0.436  1.00  0.00           N  
HETATM   52  C   UNL     1       6.758   3.518   1.731  1.00  0.00           C  
HETATM   53  N   UNL     1       6.822   4.743   2.167  1.00  0.00           N  
HETATM   54  C   UNL     1       7.288   5.547   1.181  1.00  0.00           C  
HETATM   55  C   UNL     1       7.528   4.734   0.061  1.00  0.00           C  
HETATM   56  N   UNL     1       7.995   5.290  -1.052  1.00  0.00           N  
HETATM   57  C   UNL     1       8.231   6.584  -1.108  1.00  0.00           C  
HETATM   58  N   UNL     1       8.021   7.388  -0.082  1.00  0.00           N  
HETATM   59  C   UNL     1       7.559   6.922   1.074  1.00  0.00           C  
HETATM   60  N   UNL     1       7.342   7.773   2.144  1.00  0.00           N  
HETATM   61  H   UNL     1     -19.750   5.243   1.709  1.00  0.00           H  
HETATM   62  H   UNL     1     -18.871   5.898   0.307  1.00  0.00           H  
HETATM   63  H   UNL     1     -19.777   4.373   0.157  1.00  0.00           H  
HETATM   64  H   UNL     1     -17.316   4.817   1.907  1.00  0.00           H  
HETATM   65  H   UNL     1     -18.221   3.292   1.758  1.00  0.00           H  
HETATM   66  H   UNL     1     -17.714   3.229  -0.669  1.00  0.00           H  
HETATM   67  H   UNL     1     -16.809   4.754  -0.519  1.00  0.00           H  
HETATM   68  H   UNL     1     -15.254   3.673   1.082  1.00  0.00           H  
HETATM   69  H   UNL     1     -16.159   2.148   0.932  1.00  0.00           H  
HETATM   70  H   UNL     1     -15.652   2.086  -1.495  1.00  0.00           H  
HETATM   71  H   UNL     1     -14.746   3.611  -1.345  1.00  0.00           H  
HETATM   72  H   UNL     1     -11.074   1.282   0.155  1.00  0.00           H  
HETATM   73  H   UNL     1     -11.979  -0.243   0.005  1.00  0.00           H  
HETATM   74  H   UNL     1     -10.794  -0.739  -2.115  1.00  0.00           H  
HETATM   75  H   UNL     1      -9.888   0.786  -1.965  1.00  0.00           H  
HETATM   76  H   UNL     1      -9.518  -0.706   0.404  1.00  0.00           H  
HETATM   77  H   UNL     1      -6.878  -1.242   0.476  1.00  0.00           H  
HETATM   78  H   UNL     1      -7.783  -2.767   0.327  1.00  0.00           H  
HETATM   79  H   UNL     1      -6.598  -3.263  -1.794  1.00  0.00           H  
HETATM   80  H   UNL     1      -5.692  -1.738  -1.644  1.00  0.00           H  
HETATM   81  H   UNL     1      -5.321  -3.229   0.725  1.00  0.00           H  
HETATM   82  H   UNL     1      -3.756  -3.581   1.818  1.00  0.00           H  
HETATM   83  H   UNL     1      -1.902  -3.129  -2.079  1.00  0.00           H  
HETATM   84  H   UNL     1      -0.265  -3.002  -1.394  1.00  0.00           H  
HETATM   85  H   UNL     1      -1.004  -4.602  -1.641  1.00  0.00           H  
HETATM   86  H   UNL     1      -2.589  -2.021   1.380  1.00  0.00           H  
HETATM   87  H   UNL     1      -1.274  -1.436   0.332  1.00  0.00           H  
HETATM   88  H   UNL     1      -2.900  -1.699  -0.343  1.00  0.00           H  
HETATM   89  H   UNL     1      -1.184  -3.975   2.051  1.00  0.00           H  
HETATM   90  H   UNL     1      -0.495  -5.045   0.807  1.00  0.00           H  
HETATM   91  H   UNL     1       0.986  -2.309   3.650  1.00  0.00           H  
HETATM   92  H   UNL     1       4.460  -1.136   3.499  1.00  0.00           H  
HETATM   93  H   UNL     1       6.947  -0.836   1.560  1.00  0.00           H  
HETATM   94  H   UNL     1       6.992  -2.047   0.256  1.00  0.00           H  
HETATM   95  H   UNL     1       9.736   3.107  -1.047  1.00  0.00           H  
HETATM   96  H   UNL     1       8.293  -2.918  -2.533  1.00  0.00           H  
HETATM   97  H   UNL     1      10.553  -1.802  -4.435  1.00  0.00           H  
HETATM   98  H   UNL     1       6.420   2.671   2.310  1.00  0.00           H  
HETATM   99  H   UNL     1       8.611   7.003  -2.028  1.00  0.00           H  
HETATM  100  H   UNL     1       7.528   8.721   2.055  1.00  0.00           H  
HETATM  101  H   UNL     1       7.004   7.421   2.982  1.00  0.00           H  
CONECT    1    2   61   62   63                                       
CONECT    2    1    3   64   65                                       
CONECT    3    2    4   66   67                                       
CONECT    4    3    5   68   69                                       
CONECT    5    4    6   70   71                                       
CONECT    6    5    7    7    8                                       
CONECT    7    6    6                                                 
CONECT    8    6    9                                                 
CONECT    9    8   10   72   73                                       
CONECT   10    9   11   74   75                                       
CONECT   11   10   12   76                                            
CONECT   12   11   13   13   14                                       
CONECT   13   12   12                                                 
CONECT   14   12   15   77   78                                       
CONECT   15   14   16   79   80                                       
CONECT   16   15   17   81                                            
CONECT   17   16   18   18   19                                       
CONECT   18   17   17                                                 
CONECT   19   17   20   21   22                                       
CONECT   20   19                                                      
CONECT   21   19   82                                                 
CONECT   22   19   23   24   25                                       
CONECT   23   22   83   84   85                                       
CONECT   24   22   86   87   88                                       
CONECT   25   22   26   89   90                                       
CONECT   26   25   27                                                 
CONECT   27   26   28   29   29                                       
CONECT   27   30                                                      
CONECT   28   27   91                                                 
CONECT   29   27   27                                                 
CONECT   30   27   31                                                 
CONECT   31   30   32   33   33                                       
CONECT   31   34                                                      
CONECT   32   31   92                                                 
CONECT   33   31   31                                                 
CONECT   34   31   35                                                 
CONECT   35   34   36   93   94                                       
CONECT   36   35   37   38   44                                       
CONECT   37   36                                                      
CONECT   38   36   39                                                 
CONECT   39   38   40   41   51                                       
CONECT   40   39                                                      
CONECT   41   39   42   43   44                                       
CONECT   42   41                                                      
CONECT   43   41   95                                                 
CONECT   44   41   45   36   46                                       
CONECT   45   44                                                      
CONECT   46   44   47                                                 
CONECT   47   46   48   49   50                                       
CONECT   47   50                                                      
CONECT   48   47   96                                                 
CONECT   49   47   97                                                 
CONECT   50   47   47                                                 
CONECT   51   39   52   55                                            
CONECT   52   51   53   53   98                                       
CONECT   53   52   52   54                                            
CONECT   54   53   55   55   59                                       
CONECT   55   54   54   51   56                                       
CONECT   56   55   57   57                                            
CONECT   57   56   56   58   99                                       
CONECT   58   57   59   59                                            
CONECT   59   58   58   54   60                                       
CONECT   60   59  100  101                                            
CONECT   61    1                                                      
CONECT   62    1                                                      
CONECT   63    1                                                      
CONECT   64    2                                                      
CONECT   65    2                                                      
CONECT   66    3                                                      
CONECT   67    3                                                      
CONECT   68    4                                                      
CONECT   69    4                                                      
CONECT   70    5                                                      
CONECT   71    5                                                      
CONECT   72    9                                                      
CONECT   73    9                                                      
CONECT   74   10                                                      
CONECT   75   10                                                      
CONECT   76   11                                                      
CONECT   77   14                                                      
CONECT   78   14                                                      
CONECT   79   15                                                      
CONECT   80   15                                                      
CONECT   81   16                                                      
CONECT   82   21                                                      
CONECT   83   23                                                      
CONECT   84   23                                                      
CONECT   85   23                                                      
CONECT   86   24                                                      
CONECT   87   24                                                      
CONECT   88   24                                                      
CONECT   89   25                                                      
CONECT   90   25                                                      
CONECT   91   28                                                      
CONECT   92   32                                                      
CONECT   93   35                                                      
CONECT   94   35                                                      
CONECT   95   43                                                      
CONECT   96   48                                                      
CONECT   97   49                                                      
CONECT   98   52                                                      
CONECT   99   57                                                      
CONECT  100   60                                                      
CONECT  101   60                                                      
MASTER        0    0    0    0    0    0    0    0  101    0  101    0
END

https://cactus.nci.nih.gov/chemical/structure/CCCCCC(=O)SCCNC(=O)CCNC(=O)%5BC...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:100})
101103  0  0  0  0  0  0  0  0999 V2000
  -19.1698    4.9856    0.8235 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.9226    4.2039    1.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
  -17.1076    3.8420   -0.0023 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.8604    3.0603    0.4152 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.0454    2.6984   -0.8282 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8170    1.9284   -0.4168 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.6133    1.6923    0.7557 O   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7088    1.3870   -1.6041 S   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4937    0.5614   -0.5467 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3739   -0.0185   -1.4132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3904   -0.6867   -0.5574 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3090   -1.2750   -1.1059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1501   -1.2513   -2.3080 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2973   -1.9624   -0.2255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1776   -2.5423   -1.0920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1941   -3.2105   -0.2362 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1127   -3.7988   -0.7847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0002   -3.8567   -1.9909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0433   -4.3848    0.1008 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7988   -5.3903   -0.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5184   -4.4423    1.4472 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7919   -3.5066    0.0386 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981   -3.5640   -1.3703 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1656   -2.0618    0.3760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7609   -4.0157    1.0478 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4078   -3.1955    0.9897 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6997   -3.4428    1.9182 P   0  0  1  0  0  0  0  0  0  0  0  0
    1.3063   -3.2012    3.4606 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1747   -4.8334    1.7423 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682   -2.4190    1.4957 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4641   -2.3942    1.7076 P   0  0  1  0  0  0  0  0  0  0  0  0
    4.7967   -2.0024    3.2333 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222   -3.7319    1.4088 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1198   -1.3059    0.7188 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5310   -1.1190    0.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8101   -0.0122   -0.4256 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3105   -0.2407   -1.3671 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3429    1.2488    0.0822 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2529    2.2606   -0.4001 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.0387    2.5051   -1.4405 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6431    1.5871   -0.2728 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.0149    1.6527    0.7499 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5751    2.1637   -1.1897 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3283    0.1171   -0.6560 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.8720   -0.5708   -0.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6553   -0.1235   -2.0261 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7091   -1.2483   -2.4916 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.1391   -2.7062   -2.1153 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9282   -1.1523   -4.0837 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0002   -1.0302   -1.8019 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1794    3.4614    0.4360 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7579    3.5179    1.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8223    4.7426    2.1665 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2878    5.5474    1.1814 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5277    4.7343    0.0610 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9951    5.2900   -1.0523 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2313    6.5836   -1.1084 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0215    7.3877   -0.0819 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5591    6.9222    1.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3420    7.7727    2.1436 N   0  0  0  0  0  0  0  0  0  0  0  0
  -19.7504    5.2434    1.7092 H   0  0  0  0  0  0  0  0  0  0  0  0
  -18.8709    5.8977    0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
  -19.7766    4.3728    0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
  -17.3158    4.8168    1.9075 H   0  0  0  0  0  0  0  0  0  0  0  0
  -18.2215    3.2918    1.7576 H   0  0  0  0  0  0  0  0  0  0  0  0
  -17.7144    3.2291   -0.6688 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.8087    4.7541   -0.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.2536    3.6732    1.0817 H   0  0  0  0  0  0  0  0  0  0  0  0
  -16.1593    2.1482    0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
  -15.6522    2.0855   -1.4946 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.7465    3.6106   -1.3447 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0738    1.2819    0.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.9795   -0.2431    0.0054 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7938   -0.7389   -2.1152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8881    0.7860   -1.9654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5176   -0.7057    0.4041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8775   -1.2419    0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7832   -2.7669    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5975   -3.2627   -1.7940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6918   -1.7377   -1.6441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3212   -3.2294    0.7253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7556   -3.5811    1.8178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9024   -3.1293   -2.0795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2647   -3.0017   -1.3943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0041   -4.6019   -1.6408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5887   -2.0208    1.3797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741   -1.4361    0.3317 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9001   -1.6990   -0.3430 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1840   -3.9748    2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4948   -5.0450    0.8074 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9857   -2.3086    3.6495 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4600   -1.1357    3.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9475   -0.8363    1.5600 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9919   -2.0475    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7356    3.1065   -1.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2930   -2.9176   -2.5330 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5525   -1.8020   -4.4347 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4200    2.6712    2.3104 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6113    7.0032   -2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5276    8.7206    2.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0041    7.4208    2.9821 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 61  1  0  0  0  0
  1 62  1  0  0  0  0
  1 63  1  0  0  0  0
  2  3  1  0  0  0  0
  2 64  1  0  0  0  0
  2 65  1  0  0  0  0
  3  4  1  0  0  0  0
  3 66  1  0  0  0  0
  3 67  1  0  0  0  0
  4  5  1  0  0  0  0
  4 68  1  0  0  0  0
  4 69  1  0  0  0  0
  5  6  1  0  0  0  0
  5 70  1  0  0  0  0
  5 71  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 72  1  0  0  0  0
  9 73  1  0  0  0  0
 10 11  1  0  0  0  0
 10 74  1  0  0  0  0
 10 75  1  0  0  0  0
 11 12  1  0  0  0  0
 11 76  1  0  0  0  0
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 25 89  1  0  0  0  0
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 60100  1  0  0  0  0
 60101  1  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
Caproyl-CoA	ChEBI
Caproyl-coenzyme A	ChEBI
coenzyme A, S-Hexanoate	ChEBI
Hexanoyl-coenzyme A	ChEBI
N-Hexanoyl-CoA	ChEBI
N-Hexanoyl-coenzyme A	ChEBI
S-Hexanoyl-CoA	ChEBI
S-Hexanoyl-coenzym-a	ChEBI
S-Hexanoyl-coenzyme A	ChEBI
coenzyme A, S-Hexanoic acid	Generator
CoA(6:0)	HMDB

Chemical Formula

C₂₇H₄₆N₇O₁₇P₃S

Average Molecular Weight

865.677

Monoisotopic Molecular Weight

865.188373307

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[(3R)-3-[(2-{[2-(hexanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

Traditional Name

hexanoyl-coa

CAS Registry Number

5060-32-2

SMILES

CCCCCC(=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=C1N=CN=C2N

InChI Identifier

InChI=1S/C27H46N7O17P3S/c1-4-5-6-7-18(36)55-11-10-29-17(35)8-9-30-25(39)22(38)27(2,3)13-48-54(45,46)51-53(43,44)47-12-16-21(50-52(40,41)42)20(37)26(49-16)34-15-33-19-23(28)31-14-32-24(19)34/h14-16,20-22,26,37-38H,4-13H2,1-3H3,(H,29,35)(H,30,39)(H,43,44)(H,45,46)(H2,28,31,32)(H2,40,41,42)/t16-,20-,21-,22+,26-/m1/s1

InChI Key

OEXFMSFODMQEPE-HDRQGHTBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,3,4-saturated fatty acyl coas. These are acyl-CoAs carrying a 2,3,4-saturated fatty acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

2,3,4-saturated 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

medium-chain fatty acyl-CoA (CHEBI:27540 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Cellular process:

Cell signaling

Biochemical pathway:

Biochemical process:

Role

Industrial application:

Biological role:

Physical Properties

State

Solid

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
Water Solubility	3.67 g/L	ALOGPS
logP	0.07	ALOGPS
logP	-3.8	ChemAxon
logS	-2.4	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	24	ChemAxon
Refractivity	190.64 m³·mol⁻¹	ChemAxon
Polarizability	80.88 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

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
MS	Mass Spectrum (Electron Ionization)	splash10-0002-8122294000-23a3db6d0ea2cdf0da39	2021-09-05	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000j-1931000110-940fe882d4b8cefb1914	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0079-1921000000-de60fcd8bc6f0c9bf08d	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0079-1910000000-29936f42a08315dcc8ff	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01rt-7911042450-6db5d278813c82f99785	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-4901110010-64b9e09e0fd795b938c8	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-8900100000-f1097e6a0dd8990fbfb7	2017-07-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0000000090-5cc3f6bd431e230faf4a	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03gj-9600204660-0d998b9d3d0254c489f4	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00p0-7104802930-08e206f3a7fa95fa94d3	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000000190-fde2b5c220974cde750c	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1901001680-96f2a80cee26fb36881b	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-0119000000-74dda344be4f5c2e3b01	2021-09-07	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Fatty acid Metabolism
Fatty Acid Elongation In Mitochondria
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids		Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB02563

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023074

KNApSAcK ID

Not Available

Chemspider ID

395736

KEGG Compound ID

C05270

BioCyc ID

HEXANOYL-COA

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

459

PubChem Compound

449118

PDB ID

Not Available

ChEBI ID

27540

Food Biomarker Ontology

Not Available

VMH ID

HXCOA

MarkerDB ID

Not Available

References

Synthesis Reference

Pullman, Maynard E. Convenient and versatile method for the purification of CoA thiol esters. Analytical Biochemistry (1973), 54(1), 188-98.

Material Safety Data Sheet (MSDS)

Not Available

General References

Dugan RE, Schmidt MJ, Hoganson GE, Steele J, Gilles BA, Shug AL: High-performance liquid chromatography of coenzyme A esters formed by transesterification of short-chain acylcarnitines: diagnosis of acidemias by urinary analysis. Anal Biochem. 1987 Feb 1;160(2):275-80. [PubMed:3578754 ]

Only showing the first 10 proteins. There are 112 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 3-ketoacyl-CoA thiolase, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:: ACAA2
Uniprot ID:: P42765
Molecular weight:: 41923.82

Reactions

Hexanoyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxooctanoyl-CoA	details

Enzyme Details

2. 3-ketoacyl-CoA thiolase, peroxisomal

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: ACAA1
Uniprot ID:: P09110
Molecular weight:: 34664.46

Reactions

Hexanoyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxooctanoyl-CoA	details

Enzyme Details

3. Trifunctional enzyme subunit beta, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: HADHB
Uniprot ID:: P55084
Molecular weight:: 51293.955

Reactions

Hexanoyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxooctanoyl-CoA	details

Enzyme Details

4. Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:: ALDH6A1
Uniprot ID:: Q02252
Molecular weight:: 57839.31

Enzyme Details

5. Long-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADL
Uniprot ID:: P28330
Molecular weight:: 47655.275

Reactions

Hexanoyl-CoA + FAD → trans-2-Hexenoyl-CoA + FADH	details

Enzyme Details

6. Short-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADS
Uniprot ID:: P16219
Molecular weight:: 44296.705

Reactions

Hexanoyl-CoA + FAD → trans-2-Hexenoyl-CoA + FADH	details

Enzyme Details

7. Medium-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:: ACADM
Uniprot ID:: P11310
Molecular weight:: 46587.98

Reactions

Hexanoyl-CoA + FAD → trans-2-Hexenoyl-CoA + FADH	details

Enzyme Details

8. Peroxisomal acyl-coenzyme A oxidase 1

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:: ACOX1
Uniprot ID:: Q15067
Molecular weight:: 70135.205

Reactions

Hexanoyl-CoA + FAD → trans-2-Hexenoyl-CoA + FADH	details

Enzyme Details

9. Peroxisomal acyl-coenzyme A oxidase 2

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Oxidizes the CoA esters of the bile acid intermediates di- and tri-hydroxycholestanoic acids.
Gene Name:: ACOX2
Uniprot ID:: Q99424
Molecular weight:: 76826.14

Enzyme Details

10. Isovaleryl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: IVD
Uniprot ID:: P26440
Molecular weight:: 43055.325

Transporters

Enzyme Details

1. Long-chain fatty acid transport protein 1

General function:: Lipid transport and metabolism
Specific function:: Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:: SLC27A1
Uniprot ID:: Q6PCB7
Molecular weight:: 71107.5

Only showing the first 10 proteins. There are 112 proteins in total.

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Showing metabocard for Hexanoyl-CoA (HMDB0002845)

MOL for HMDB0002845 (Hexanoyl-CoA)

3D MOL for HMDB0002845 (Hexanoyl-CoA)

3D SDF for HMDB0002845 (Hexanoyl-CoA)

3D-SDF for HMDB0002845 (Hexanoyl-CoA)

PDB for HMDB0002845 (Hexanoyl-CoA)

3D PDB for HMDB0002845 (Hexanoyl-CoA)

SMILES for HMDB0002845 (Hexanoyl-CoA)

INCHI for HMDB0002845 (Hexanoyl-CoA)

Structure for HMDB0002845 (Hexanoyl-CoA)

3D Structure for HMDB0002845 (Hexanoyl-CoA)

GC-MS

LC-MS/MS

Enzymes

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Transporters