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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 07:49:56 UTC

Update Date

2021-09-14 15:45:34 UTC

HMDB ID

HMDB0003942

Secondary Accession Numbers

HMDB03942

Metabolite Identification

Common Name

(S)-Hydroxyhexanoyl-CoA

Description

(S)-Hydroxyhexanoyl-CoA is an intermediate in fatty acid metabolism, being the substrate of the enzymes beta-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.211) and 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35). (S)-Hydroxyhexanoyl-CoA is also an intermediate in fatty acid elongation in mitochondria, the substrate of the enzymes enoyl-CoA hydratase (EC 4.2.1.17) and long-chain-enoyl-CoA hydratase (EC 4.2.1.74) (KEGG).

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI

ChEBI
  Mrv1652305151822572D          

 56 58  0  0  1  0            999 V2000
   31.5016  -15.8591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   30.8342  -15.3742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2467  -16.6437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.1667  -15.8591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.4217  -16.6437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   31.7316  -17.3112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7559  -19.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4987  -20.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0414  -20.3126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3270  -19.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6125  -20.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0698  -18.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3270  -19.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0698  -17.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6408  -17.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3553  -17.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7843  -16.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6573  -15.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0698  -16.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4823  -15.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3553  -16.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.6408  -16.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4987  -16.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1487  -16.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7987  -16.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3237  -15.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3237  -17.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9737  -15.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9737  -17.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3237  -16.1875    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.9737  -16.1875    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.3821  -15.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9367  -17.3112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1117  -18.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7617  -18.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9367  -18.1362    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.9367  -18.9612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2862  -15.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8994  -16.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6218  -14.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6138  -15.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8994  -16.9812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.4423  -14.9367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3283  -16.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6139  -17.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3283  -16.9811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2132  -19.9000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.9277  -21.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9277  -20.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6421  -19.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3566  -21.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3566  -20.3126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.0711  -19.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7856  -20.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5000  -19.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0427  -15.7435    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 52  1  0  0  0  0
 52 51  1  6  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 44 56  1  0  0  0  0
M  END

ChEBI
  Mrv1652305151822572D          

 56 58  0  0  1  0            999 V2000
   31.5016  -15.8591    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   30.8342  -15.3742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2467  -16.6437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.1667  -15.8591    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   30.4217  -16.6437    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   31.7316  -17.3112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7559  -19.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4987  -20.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0414  -20.3126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3270  -19.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6125  -20.3126    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0698  -18.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3270  -19.0751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0698  -17.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6408  -17.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3553  -17.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7843  -16.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6573  -15.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0698  -16.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4823  -15.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3553  -16.6000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.6408  -16.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4987  -16.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.1487  -16.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7987  -16.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3237  -15.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3237  -17.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9737  -15.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.9737  -17.0125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3237  -16.1875    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   27.9737  -16.1875    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.3821  -15.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9367  -17.3112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.1117  -18.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7617  -18.1362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9367  -18.1362    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.9367  -18.9612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.2862  -15.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.8994  -16.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6218  -14.8505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6138  -15.7437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8994  -16.9812    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.4423  -14.9367    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.3283  -16.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6139  -17.3936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3283  -16.9811    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.2132  -19.9000    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.9277  -21.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9277  -20.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6421  -19.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3566  -21.1376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.3566  -20.3126    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   29.0711  -19.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7856  -20.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5000  -19.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0427  -15.7435    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 52  1  0  0  0  0
 52 51  1  6  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 44 56  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0003942

> <DATABASE_NAME>
hmdb

> <SMILES>
CCC[C@H](O)CC(=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/C27H46N7O18P3S/c1-4-5-15(35)10-18(37)56-9-8-29-17(36)6-7-30-25(40)22(39)27(2,3)12-49-55(46,47)52-54(44,45)48-11-16-21(51-53(41,42)43)20(38)26(50-16)34-14-33-19-23(28)31-13-32-24(19)34/h13-16,20-22,26,35,38-39H,4-12H2,1-3H3,(H,29,36)(H,30,40)(H,44,45)(H,46,47)(H2,28,31,32)(H2,41,42,43)/t15-,16+,20+,21+,22-,26+/m0/s1

> <INCHI_KEY>
VAAHKRMGOFIORX-IKTBLOROSA-N

> <FORMULA>
C27H46N7O18P3S

> <MOLECULAR_WEIGHT>
881.68

> <EXACT_MASS>
881.183289837

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
102

> <JCHEM_AVERAGE_POLARIZABILITY>
79.9229882958216

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-{2-[(2-{[(3S)-3-hydroxyhexanoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid

> <ALOGPS_LOGP>
-0.28

> <JCHEM_LOGP>
-4.816559161484992

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.885963887863011

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8191119137286842

> <JCHEM_PKA_STRONGEST_BASIC>
6.417078595605377

> <JCHEM_POLAR_SURFACE_AREA>
390.8400000000001

> <JCHEM_REFRACTIVITY>
193.1968000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.71e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-hydroxyhexanoyl-coa

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/CCC%5BC@H%5D(O)CC(=O)SCCNC(=O)C...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:101})
102104  0  0  0  0  0  0  0  0999 V2000
   19.1292   -4.3372    0.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8146   -3.6869    1.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9362   -3.4400   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6216   -2.7896    0.3064 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8349   -1.8857    0.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9887    2.1213   -0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8576    2.6928   -1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.9827   -3.5643    1.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
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   18.0246   -2.7378    1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.4571   -2.7783   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7262   -4.3890   -0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6595   -4.5329    0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3922   -1.8027   -1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.5816    1.3897    0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0623    3.0743   -1.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    4.6863   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    2.1032    1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756    1.5090    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5950    1.7993   -0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8583    4.0326    2.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7406    1.1059    3.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2319    0.7881    1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2982    2.0088    0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9773   -3.1715   -1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6226    2.8831   -2.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6539   -2.7178    2.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
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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      58.803 -29.604   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      57.557 -28.699   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      58.327 -31.068   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      56.311 -29.604   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      56.787 -31.068   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      59.232 -32.314   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      46.211 -37.147   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      47.598 -37.917   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      44.877 -37.917   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      43.544 -37.147   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      42.210 -37.917   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      44.930 -34.837   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      43.544 -35.607   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      44.930 -33.297   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      42.263 -33.297   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      43.597 -32.527   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      46.264 -30.987   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      44.160 -28.883   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      44.930 -30.217   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      45.700 -28.883   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      43.597 -30.987   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      42.263 -30.217   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      47.598 -30.217   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      50.678 -30.217   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      53.758 -30.217   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      49.138 -28.677   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      49.138 -31.757   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      52.218 -28.677   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      52.218 -31.757   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      49.138 -30.217   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      52.218 -30.217   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      54.847 -29.128   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      55.882 -32.314   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      54.342 -33.854   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      57.422 -33.854   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      55.882 -33.854   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      55.882 -35.394   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      60.268 -29.128   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      61.412 -30.158   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      60.894 -27.721   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      62.746 -29.388   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      61.412 -31.698   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      62.426 -27.882   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      64.079 -30.158   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      62.746 -32.468   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      64.079 -31.698   0.000  0.00  0.00           N+0
HETATM   47  S   UNK     0      48.931 -37.147   0.000  0.00  0.00           S+0
HETATM   48  O   UNK     0      50.265 -39.457   0.000  0.00  0.00           O+0
HETATM   49  C   UNK     0      50.265 -37.917   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      51.599 -37.147   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      52.932 -39.457   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      52.932 -37.917   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      54.266 -37.147   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      55.600 -37.917   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      56.933 -37.147   0.000  0.00  0.00           C+0
HETATM   56  N   UNK     0      65.413 -29.388   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   56                                                  
CONECT   45   42   46                                                       
CONECT   46   44   45                                                       
CONECT   47    8   49                                                       
CONECT   48   49                                                            
CONECT   49   47   48   50                                                  
CONECT   50   49   52                                                       
CONECT   51   52                                                            
CONECT   52   50   51   53                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54                                                            
CONECT   56   44                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/CCC%5BC@H%5D(O)CC(=O)SCCNC(=O)C... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1      19.129  -4.337   0.663  1.00  0.00           C  
HETATM    2  C   UNL     1      17.815  -3.687   1.099  1.00  0.00           C  
HETATM    3  C   UNL     1      16.936  -3.440  -0.129  1.00  0.00           C  
HETATM    4  C   UNL     1      15.622  -2.790   0.306  1.00  0.00           C  
HETATM    5  H   UNL     1      15.835  -1.886   0.877  1.00  0.00           H  
HETATM    6  O   UNL     1      14.885  -3.704   1.121  1.00  0.00           O  
HETATM    7  C   UNL     1      14.797  -2.429  -0.931  1.00  0.00           C  
HETATM    8  C   UNL     1      13.559  -1.679  -0.508  1.00  0.00           C  
HETATM    9  O   UNL     1      13.358  -1.455   0.667  1.00  0.00           O  
HETATM   10  S   UNL     1      12.439  -1.143  -1.687  1.00  0.00           S  
HETATM   11  C   UNL     1      11.217  -0.343  -0.618  1.00  0.00           C  
HETATM   12  C   UNL     1      10.086   0.229  -1.475  1.00  0.00           C  
HETATM   13  N   UNL     1       9.098   0.877  -0.610  1.00  0.00           N  
HETATM   14  C   UNL     1       8.006   1.455  -1.149  1.00  0.00           C  
HETATM   15  O   UNL     1       7.842   1.438  -2.351  1.00  0.00           O  
HETATM   16  C   UNL     1       6.989   2.121  -0.260  1.00  0.00           C  
HETATM   17  C   UNL     1       5.858   2.693  -1.117  1.00  0.00           C  
HETATM   18  N   UNL     1       4.869   3.341  -0.252  1.00  0.00           N  
HETATM   19  C   UNL     1       3.777   3.919  -0.791  1.00  0.00           C  
HETATM   20  O   UNL     1       3.659   3.985  -1.996  1.00  0.00           O  
HETATM   21  C   UNL     1       2.704   4.483   0.103  1.00  0.00           C  
HETATM   22  H   UNL     1       2.444   5.488  -0.230  1.00  0.00           H  
HETATM   23  O   UNL     1       3.184   4.537   1.448  1.00  0.00           O  
HETATM   24  C   UNL     1       1.464   3.588   0.040  1.00  0.00           C  
HETATM   25  C   UNL     1       0.864   3.649  -1.367  1.00  0.00           C  
HETATM   26  C   UNL     1       1.859   2.146   0.364  1.00  0.00           C  
HETATM   27  C   UNL     1       0.430   4.076   1.057  1.00  0.00           C  
HETATM   28  O   UNL     1      -0.727   3.240   0.997  1.00  0.00           O  
HETATM   29  P   UNL     1      -2.018   3.463   1.933  1.00  0.00           P  
HETATM   30  O   UNL     1      -1.615   3.214   3.472  1.00  0.00           O  
HETATM   31  O   UNL     1      -2.513   4.848   1.770  1.00  0.00           O  
HETATM   32  O   UNL     1      -3.175   2.426   1.507  1.00  0.00           O  
HETATM   33  P   UNL     1      -4.769   2.378   1.725  1.00  0.00           P  
HETATM   34  O   UNL     1      -5.090   1.970   3.249  1.00  0.00           O  
HETATM   35  O   UNL     1      -5.347   3.711   1.439  1.00  0.00           O  
HETATM   36  O   UNL     1      -5.414   1.289   0.731  1.00  0.00           O  
HETATM   37  C   UNL     1      -6.823   1.084   0.609  1.00  0.00           C  
HETATM   38  C   UNL     1      -7.092  -0.018  -0.417  1.00  0.00           C  
HETATM   39  H   UNL     1      -6.599   0.224  -1.359  1.00  0.00           H  
HETATM   40  O   UNL     1      -6.605  -1.277   0.079  1.00  0.00           O  
HETATM   41  C   UNL     1      -7.504  -2.297  -0.408  1.00  0.00           C  
HETATM   42  H   UNL     1      -7.290  -2.530  -1.451  1.00  0.00           H  
HETATM   43  C   UNL     1      -8.902  -1.644  -0.270  1.00  0.00           C  
HETATM   44  H   UNL     1      -9.269  -1.722   0.754  1.00  0.00           H  
HETATM   45  O   UNL     1      -9.830  -2.226  -1.187  1.00  0.00           O  
HETATM   46  C   UNL     1      -8.609  -0.167  -0.642  1.00  0.00           C  
HETATM   47  H   UNL     1      -9.159   0.509   0.013  1.00  0.00           H  
HETATM   48  O   UNL     1      -8.945   0.081  -2.009  1.00  0.00           O  
HETATM   49  P   UNL     1     -10.016   1.194  -2.462  1.00  0.00           P  
HETATM   50  O   UNL     1      -9.464   2.657  -2.076  1.00  0.00           O  
HETATM   51  O   UNL     1     -10.240   1.108  -4.053  1.00  0.00           O  
HETATM   52  O   UNL     1     -11.301   0.954  -1.768  1.00  0.00           O  
HETATM   53  N   UNL     1      -7.410  -3.503   0.418  1.00  0.00           N  
HETATM   54  C   UNL     1      -6.983  -3.564   1.711  1.00  0.00           C  
HETATM   55  N   UNL     1      -7.029  -4.793   2.137  1.00  0.00           N  
HETATM   56  C   UNL     1      -7.487  -5.596   1.147  1.00  0.00           C  
HETATM   57  C   UNL     1      -7.743  -4.778   0.035  1.00  0.00           C  
HETATM   58  N   UNL     1      -8.208  -5.331  -1.081  1.00  0.00           N  
HETATM   59  C   UNL     1      -8.426  -6.627  -1.147  1.00  0.00           C  
HETATM   60  N   UNL     1      -8.201  -7.437  -0.128  1.00  0.00           N  
HETATM   61  C   UNL     1      -7.740  -6.974   1.030  1.00  0.00           C  
HETATM   62  N   UNL     1      -7.507  -7.830   2.092  1.00  0.00           N  
HETATM   63  H   UNL     1      18.919  -5.286   0.170  1.00  0.00           H  
HETATM   64  H   UNL     1      19.650  -3.676  -0.029  1.00  0.00           H  
HETATM   65  H   UNL     1      19.755  -4.513   1.538  1.00  0.00           H  
HETATM   66  H   UNL     1      17.294  -4.349   1.791  1.00  0.00           H  
HETATM   67  H   UNL     1      18.025  -2.738   1.592  1.00  0.00           H  
HETATM   68  H   UNL     1      17.457  -2.778  -0.821  1.00  0.00           H  
HETATM   69  H   UNL     1      16.726  -4.389  -0.622  1.00  0.00           H  
HETATM   70  H   UNL     1      14.659  -4.533   0.676  1.00  0.00           H  
HETATM   71  H   UNL     1      15.392  -1.803  -1.595  1.00  0.00           H  
HETATM   72  H   UNL     1      14.508  -3.341  -1.453  1.00  0.00           H  
HETATM   73  H   UNL     1      10.810  -1.074   0.080  1.00  0.00           H  
HETATM   74  H   UNL     1      11.695   0.464  -0.061  1.00  0.00           H  
HETATM   75  H   UNL     1      10.493   0.960  -2.173  1.00  0.00           H  
HETATM   76  H   UNL     1       9.609  -0.578  -2.032  1.00  0.00           H  
HETATM   77  H   UNL     1       9.228   0.890   0.351  1.00  0.00           H  
HETATM   78  H   UNL     1       6.582   1.390   0.439  1.00  0.00           H  
HETATM   79  H   UNL     1       7.466   2.928   0.297  1.00  0.00           H  
HETATM   80  H   UNL     1       6.265   3.424  -1.815  1.00  0.00           H  
HETATM   81  H   UNL     1       5.380   1.886  -1.673  1.00  0.00           H  
HETATM   82  H   UNL     1       5.000   3.354   0.710  1.00  0.00           H  
HETATM   83  H   UNL     1       3.434   3.676   1.811  1.00  0.00           H  
HETATM   84  H   UNL     1       1.571   3.229  -2.082  1.00  0.00           H  
HETATM   85  H   UNL     1      -0.062   3.074  -1.391  1.00  0.00           H  
HETATM   86  H   UNL     1       0.654   4.686  -1.628  1.00  0.00           H  
HETATM   87  H   UNL     1       2.287   2.103   1.365  1.00  0.00           H  
HETATM   88  H   UNL     1       0.976   1.509   0.318  1.00  0.00           H  
HETATM   89  H   UNL     1       2.595   1.799  -0.361  1.00  0.00           H  
HETATM   90  H   UNL     1       0.858   4.033   2.058  1.00  0.00           H  
HETATM   91  H   UNL     1       0.149   5.103   0.826  1.00  0.00           H  
HETATM   92  H   UNL     1      -1.282   2.325   3.652  1.00  0.00           H  
HETATM   93  H   UNL     1      -4.741   1.106   3.507  1.00  0.00           H  
HETATM   94  H   UNL     1      -7.232   0.788   1.575  1.00  0.00           H  
HETATM   95  H   UNL     1      -7.298   2.009   0.282  1.00  0.00           H  
HETATM   96  H   UNL     1      -9.977  -3.171  -1.051  1.00  0.00           H  
HETATM   97  H   UNL     1      -8.623   2.883  -2.495  1.00  0.00           H  
HETATM   98  H   UNL     1     -10.875   1.752  -4.397  1.00  0.00           H  
HETATM   99  H   UNL     1      -6.654  -2.718   2.296  1.00  0.00           H  
HETATM  100  H   UNL     1      -8.805  -7.045  -2.068  1.00  0.00           H  
HETATM  101  H   UNL     1      -7.681  -8.780   1.997  1.00  0.00           H  
HETATM  102  H   UNL     1      -7.171  -7.480   2.932  1.00  0.00           H  
CONECT    1    2   63   64   65                                       
CONECT    2    1    3   66   67                                       
CONECT    3    2    4   68   69                                       
CONECT    4    3    5    6    7                                       
CONECT    5    4                                                      
CONECT    6    4   70                                                 
CONECT    7    4    8   71   72                                       
CONECT    8    7    9    9   10                                       
CONECT    9    8    8                                                 
CONECT   10    8   11                                                 
CONECT   11   10   12   73   74                                       
CONECT   12   11   13   75   76                                       
CONECT   13   12   14   77                                            
CONECT   14   13   15   15   16                                       
CONECT   15   14   14                                                 
CONECT   16   14   17   78   79                                       
CONECT   17   16   18   80   81                                       
CONECT   18   17   19   82                                            
CONECT   19   18   20   20   21                                       
CONECT   20   19   19                                                 
CONECT   21   19   22   23   24                                       
CONECT   22   21                                                      
CONECT   23   21   83                                                 
CONECT   24   21   25   26   27                                       
CONECT   25   24   84   85   86                                       
CONECT   26   24   87   88   89                                       
CONECT   27   24   28   90   91                                       
CONECT   28   27   29                                                 
CONECT   29   28   30   31   31                                       
CONECT   29   32                                                      
CONECT   30   29   92                                                 
CONECT   31   29   29                                                 
CONECT   32   29   33                                                 
CONECT   33   32   34   35   35                                       
CONECT   33   36                                                      
CONECT   34   33   93                                                 
CONECT   35   33   33                                                 
CONECT   36   33   37                                                 
CONECT   37   36   38   94   95                                       
CONECT   38   37   39   40   46                                       
CONECT   39   38                                                      
CONECT   40   38   41                                                 
CONECT   41   40   42   43   53                                       
CONECT   42   41                                                      
CONECT   43   41   44   45   46                                       
CONECT   44   43                                                      
CONECT   45   43   96                                                 
CONECT   46   43   47   38   48                                       
CONECT   47   46                                                      
CONECT   48   46   49                                                 
CONECT   49   48   50   51   52                                       
CONECT   49   52                                                      
CONECT   50   49   97                                                 
CONECT   51   49   98                                                 
CONECT   52   49   49                                                 
CONECT   53   41   54   57                                            
CONECT   54   53   55   55   99                                       
CONECT   55   54   54   56                                            
CONECT   56   55   57   57   61                                       
CONECT   57   56   56   53   58                                       
CONECT   58   57   59   59                                            
CONECT   59   58   58   60  100                                       
CONECT   60   59   61   61                                            
CONECT   61   60   60   56   62                                       
CONECT   62   61  101  102                                            
CONECT   63    1                                                      
CONECT   64    1                                                      
CONECT   65    1                                                      
CONECT   66    2                                                      
CONECT   67    2                                                      
CONECT   68    3                                                      
CONECT   69    3                                                      
CONECT   70    6                                                      
CONECT   71    7                                                      
CONECT   72    7                                                      
CONECT   73   11                                                      
CONECT   74   11                                                      
CONECT   75   12                                                      
CONECT   76   12                                                      
CONECT   77   13                                                      
CONECT   78   16                                                      
CONECT   79   16                                                      
CONECT   80   17                                                      
CONECT   81   17                                                      
CONECT   82   18                                                      
CONECT   83   23                                                      
CONECT   84   25                                                      
CONECT   85   25                                                      
CONECT   86   25                                                      
CONECT   87   26                                                      
CONECT   88   26                                                      
CONECT   89   26                                                      
CONECT   90   27                                                      
CONECT   91   27                                                      
CONECT   92   30                                                      
CONECT   93   34                                                      
CONECT   94   37                                                      
CONECT   95   37                                                      
CONECT   96   45                                                      
CONECT   97   50                                                      
CONECT   98   51                                                      
CONECT   99   54                                                      
CONECT  100   59                                                      
CONECT  101   62                                                      
CONECT  102   62                                                      
MASTER        0    0    0    0    0    0    0    0  102    0  102    0
END

https://cactus.nci.nih.gov/chemical/structure/CCC%5BC@H%5D(O)CC(=O)SCCNC(=O)C...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:101})
102104  0  0  0  0  0  0  0  0999 V2000
   19.1292   -4.3372    0.6634 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8146   -3.6869    1.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9362   -3.4400   -0.1292 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6216   -2.7896    0.3064 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.8349   -1.8857    0.8769 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.8846   -3.7040    1.1205 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7966   -2.4290   -0.9307 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5595   -1.6791   -0.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3576   -1.4549    0.6669 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4392   -1.1433   -1.6867 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.2175   -0.3427   -0.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0863    0.2288   -1.4751 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0975    0.8768   -0.6100 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0059    1.4547   -1.1494 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8423    1.4383   -2.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9887    2.1213   -0.2595 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8576    2.6928   -1.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8688    3.3408   -0.2516 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7772    3.9187   -0.7909 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6589    3.9846   -1.9962 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7037    4.4831    0.1035 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4442    5.4879   -0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1836    4.5365    1.4484 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4641    3.5885    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    3.6490   -1.3665 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8587    2.1463    0.3639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4305    4.0757    1.0569 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7273    3.2402    0.9971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0184    3.4626    1.9328 P   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6153    3.2141    3.4716 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5130    4.8480    1.7699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1748    2.4264    1.5069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7692    2.3783    1.7251 P   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0901    1.9699    3.2491 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3467    3.7106    1.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4143    1.2890    0.7305 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8233    1.0840    0.6091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0918   -0.0184   -0.4173 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5993    0.2243   -1.3590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6054   -1.2769    0.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5037   -2.2972   -0.4080 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2905   -2.5305   -1.4512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9022   -1.6436   -0.2697 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.2689   -1.7223    0.7538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8302   -2.2256   -1.1874 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6090   -0.1665   -0.6425 C   0  0  2  0  0  0  0  0  0  0  0  0
   -9.1592    0.5089    0.0127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9450    0.0805   -2.0093 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0158    1.1945   -2.4616 P   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4640    2.6570   -2.0760 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2403    1.1081   -4.0535 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3010    0.9535   -1.7683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4103   -3.5035    0.4182 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9827   -3.5643    1.7111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0287   -4.7932    2.1370 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4874   -5.5965    1.1473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7430   -4.7780    0.0345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2076   -5.3311   -1.0813 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4264   -6.6273   -1.1467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2014   -7.4366   -0.1275 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7405   -6.9740    1.0299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5074   -7.8298    2.0921 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9191   -5.2863    0.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.6501   -3.6756   -0.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.7549   -4.5132    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.2937   -4.3486    1.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.0246   -2.7378    1.5922 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.4571   -2.7783   -0.8214 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7262   -4.3890   -0.6224 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6595   -4.5329    0.6761 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3922   -1.8027   -1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.5079   -3.3410   -1.4533 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8103   -1.0743    0.0801 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6947    0.4639   -0.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4935    0.9604   -2.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6091   -0.5779   -2.0316 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2284    0.8900    0.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5816    1.3897    0.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4660    2.9280    0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2647    3.4244   -1.8146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3804    1.8861   -1.6732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9997    3.3539    0.7095 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4340    3.6757    1.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5708    3.2295   -2.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0623    3.0743   -1.3911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    4.6863   -1.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2865    2.1032    1.3655 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9756    1.5090    0.3184 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5950    1.7993   -0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8583    4.0326    2.0585 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1494    5.1031    0.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2819    2.3245    3.6521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7406    1.1059    3.5067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2319    0.7881    1.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2982    2.0088    0.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9773   -3.1715   -1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6226    2.8831   -2.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8748    1.7520   -4.3968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6539   -2.7178    2.2956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8045   -7.0447   -2.0682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6806   -8.7795    1.9968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1709   -7.4801    2.9319 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 63  1  0  0  0  0
  1 64  1  0  0  0  0
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  2 66  1  0  0  0  0
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M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
(S)-3-Hydroxycaproyl-CoA	ChEBI
(S)-3-Hydroxycaproyl-coenzyme A	ChEBI
3-Hydroxyhexanoyl-coenzyme A	ChEBI
(S)-3-Hydroxyhexanoyl-CoA	Kegg
(S)-Hydroxyhexanoyl-CoA	ChEBI

Chemical Formula

C₂₇H₄₆N₇O₁₈P₃S

Average Molecular Weight

881.68

Monoisotopic Molecular Weight

881.183289837

IUPAC Name

4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-{2-[(2-{[(3S)-3-hydroxyhexanoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanimidic acid

Traditional Name

(S)-hydroxyhexanoyl-coa

CAS Registry Number

79171-47-4

SMILES

CCC[C@H](O)CC(=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/C27H46N7O18P3S/c1-4-5-15(35)10-18(37)56-9-8-29-17(36)6-7-30-25(40)22(39)27(2,3)12-49-55(46,47)52-54(44,45)48-11-16-21(51-53(41,42)43)20(38)26(50-16)34-14-33-19-23(28)31-13-32-24(19)34/h13-16,20-22,26,35,38-39H,4-12H2,1-3H3,(H,29,36)(H,30,40)(H,44,45)(H,46,47)(H2,28,31,32)(H2,41,42,43)/t15-,16+,20+,21+,22-,26+/m0/s1

InChI Key

VAAHKRMGOFIORX-IKTBLOROSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as (s)-3-hydroxyacyl coas. These are organic compounds containing a (S)-3-hydroxyl acylated coenzyme A derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

(S)-3-hydroxyacyl 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

hydroxy fatty acyl-CoA (CHEBI:28276 )

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 Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-3.019	Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.71 g/L	ALOGPS
logP	-0.28	ALOGPS
logP	-4.8	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	6.42	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	390.84 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	193.2 m³·mol⁻¹	ChemAxon
Polarizability	79.92 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

Predicted Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference

Retention Indices

Underivatized

Not Available

Derivatized

Not Available

Spectra

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1912000130-9d32f1a7db66966548f9	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0913000000-325a72f7e906068360b8	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1911000000-391d16b13e4ae8bf53de	2019-02-22	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-5911140350-4d35b969b1c6af839051	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-3910110010-ec218967cee87cdd7488	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-4900100000-f4b7577fa42ccd3e2dee	2019-02-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0000000090-22f1eaad51934a88d28c	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00p0-7800102890-d08bf7452876ed8a38d2	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002o-9302601610-9537bb62a975804266fc	2021-09-08	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
Long-chain-3-hydroxyacyl-coa dehydrogenase deficiency (LCHAD)		Not Available
Ethylmalonic Encephalopathy		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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB030163

KNApSAcK ID

Not Available

Chemspider ID

10140154

KEGG Compound ID

C05268

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11966160

PDB ID

Not Available

ChEBI ID

28276

Food Biomarker Ontology

Not Available

VMH ID

HC01407

MarkerDB ID

Not Available

References

Synthesis Reference

Tamvakopoulos, Constantine S.; Anderson, Vernon E. Detection of acyl-coenzyme A thioester intermediates of fatty acid b-oxidation as the N-acylglycines by negative-ion chemical ionization gas chromatography mass spectrometry. Anal Biochem. 1992 Feb 1;200(2):381-7. Pubmed: 1632504

Material Safety Data Sheet (MSDS)

Not Available

General References

Dalluge JJ, Gort S, Hobson R, Selifonova O, Amore F, Gokarn R: Separation and identification of organic acid-coenzyme A thioesters using liquid chromatography/electrospray ionization-mass spectrometry. Anal Bioanal Chem. 2002 Nov;374(5):835-40. Epub 2002 Oct 8. [PubMed:12434239 ]
Klees AG, Linder D, Buckel W: 2-Hydroxyglutaryl-CoA dehydratase from Fusobacterium nucleatum (subsp. nucleatum): an iron-sulfur flavoprotein. Arch Microbiol. 1992;158(4):294-301. [PubMed:1417419 ]
Kim J, Hetzel M, Boiangiu CD, Buckel W: Dehydration of (R)-2-hydroxyacyl-CoA to enoyl-CoA in the fermentation of alpha-amino acids by anaerobic bacteria. FEMS Microbiol Rev. 2004 Oct;28(4):455-68. [PubMed:15374661 ]
Hofmeister AE, Buckel W: (R)-lactyl-CoA dehydratase from Clostridium propionicum. Stereochemistry of the dehydration of (R)-2-hydroxybutyryl-CoA to crotonyl-CoA. Eur J Biochem. 1992 Jun 1;206(2):547-52. [PubMed:1597194 ]
Kuchta RD, Hanson GR, Holmquist B, Abeles RH: Fe-S centers in lactyl-CoA dehydratase. Biochemistry. 1986 Nov 18;25(23):7301-7. [PubMed:3026450 ]
Kuchta RD, Abeles RH: Lactate reduction in Clostridium propionicum. Purification and properties of lactyl-CoA dehydratase. J Biol Chem. 1985 Oct 25;260(24):13181-9. [PubMed:4055736 ]
Sokatch JR: Alanine and aspartate formation during growth on valine-C14 by Pseudomonas aeruginosa. J Bacteriol. 1966 Jul;92(1):72-5. [PubMed:4957438 ]
Megraw RE, Reeves HC, Ajl SJ: Formation of lactyl-coenzyme A and pyruvyl-coenzyme A from lactic acid by Escherichia coli. J Bacteriol. 1965 Oct;90(4):984-8. [PubMed:5321404 ]

Enzymes

Enzyme Details

1. 3-hydroxyacyl-CoA dehydrogenase type-2

General function:: Involved in oxidoreductase activity
Specific function:: Functions in mitochondrial tRNA maturation. Part of mitochondrial ribonuclease P, an enzyme composed of MRPP1/TRMT10C, MRPP2/HSD17B10 and MRPP3/KIAA0391, which cleaves tRNA molecules in their 5'-ends. By interacting with intracellular amyloid-beta, it may contribute to the neuronal dysfunction associated with Alzheimer disease (AD).
Gene Name:: HSD17B10
Uniprot ID:: Q99714
Molecular weight:: 25983.695

Enzyme Details

2. Peroxisomal bifunctional enzyme

General function:: Involved in oxidoreductase activity
Specific function:: Not Available
Gene Name:: EHHADH
Uniprot ID:: Q08426
Molecular weight:: 69153.26

Reactions

(S)-Hydroxyhexanoyl-CoA + NAD → 3-Oxohexanoyl-CoA + NADH + Hydrogen Ion	details
(S)-Hydroxyhexanoyl-CoA → trans-2-Hexenoyl-CoA + Water	details

Enzyme Details

3. Hydroxyacyl-coenzyme A dehydrogenase, mitochondrial

General function:: Involved in 3-hydroxyacyl-CoA dehydrogenase activity
Specific function:: Plays an essential role in the mitochondrial beta-oxidation of short chain fatty acids. Exerts it highest activity toward 3-hydroxybutyryl-CoA.
Gene Name:: HADH
Uniprot ID:: Q16836
Molecular weight:: 36035.11

Reactions

(S)-Hydroxyhexanoyl-CoA + NAD → 3-Oxohexanoyl-CoA + NADH + Hydrogen Ion	details

Enzyme Details

4. Enoyl-CoA hydratase, mitochondrial

General function:: Involved in catalytic activity
Specific function:: Straight-chain enoyl-CoA thioesters from C4 up to at least C16 are processed, although with decreasing catalytic rate.
Gene Name:: ECHS1
Uniprot ID:: P30084
Molecular weight:: 31387.085

Reactions

(S)-Hydroxyhexanoyl-CoA → trans-2-Hexenoyl-CoA + Water	details

Enzyme Details

5. Trifunctional enzyme subunit alpha, mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Bifunctional subunit.
Gene Name:: HADHA
Uniprot ID:: P40939
Molecular weight:: 82998.97

Reactions

(S)-Hydroxyhexanoyl-CoA + NAD → 3-Oxohexanoyl-CoA + NADH + Hydrogen Ion	details
(S)-Hydroxyhexanoyl-CoA → trans-2-Hexenoyl-CoA + Water	details

Enzyme Details

6. Peroxisomal multifunctional enzyme type 2

General function:: Involved in oxidoreductase activity
Specific function:: Bifunctional enzyme acting on the peroxisomal beta-oxidation pathway for fatty acids. Catalyzes the formation of 3-ketoacyl-CoA intermediates from both straight-chain and 2-methyl-branched-chain fatty acids.
Gene Name:: HSD17B4
Uniprot ID:: P51659
Molecular weight:: 79685.715

Showing metabocard for (S)-Hydroxyhexanoyl-CoA (HMDB0003942)

MOL for HMDB0003942 ((S)-Hydroxyhexanoyl-CoA)

3D MOL for HMDB0003942 ((S)-Hydroxyhexanoyl-CoA)

3D SDF for HMDB0003942 ((S)-Hydroxyhexanoyl-CoA)

3D-SDF for HMDB0003942 ((S)-Hydroxyhexanoyl-CoA)

PDB for HMDB0003942 ((S)-Hydroxyhexanoyl-CoA)

3D PDB for HMDB0003942 ((S)-Hydroxyhexanoyl-CoA)

SMILES for HMDB0003942 ((S)-Hydroxyhexanoyl-CoA)

INCHI for HMDB0003942 ((S)-Hydroxyhexanoyl-CoA)

Structure for HMDB0003942 ((S)-Hydroxyhexanoyl-CoA)

3D Structure for HMDB0003942 ((S)-Hydroxyhexanoyl-CoA)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

LC-MS/MS

Enzymes

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