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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

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:40:14 UTC

HMDB ID

HMDB0001356

Secondary Accession Numbers

HMDB0002029
HMDB01356
HMDB02029

Metabolite Identification

Common Name

2-Methyl-3-hydroxybutyryl-CoA

Description

2-Methyl-3-hydroxybutyryl-CoA (CAS: 6701-38-8) belongs to the class of organic compounds known as (S)-3-hydroxyacyl-CoAs. These are organic compounds containing an (S)-3-hydroxyl acylated coenzyme A derivative. Thus, 2-methyl-3-hydroxybutyryl-CoA is considered to be a fatty ester lipid molecule. 2-Methyl-3-hydroxybutyryl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Methyl-3-hydroxybutyryl-CoA is a substrate for 3-hydroxyacyl-CoA dehydrogenase type II, enoyl-CoA hydratase, trifunctional enzyme alpha subunit, short-chain 3-hydroxyacyl-CoA dehydrogenase, and peroxisomal bifunctional enzyme.

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305122021022D          

 55 57  0  0  1  0            999 V2000
   26.4683   -1.3115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.8009   -0.8266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2134   -2.0961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.1334   -1.3115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.3884   -2.0961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.6983   -2.7636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7225   -5.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4654   -5.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0081   -5.7650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2937   -5.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5792   -5.7650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0365   -4.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2937   -4.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0365   -3.2900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6076   -3.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3220   -2.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7510   -2.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6240   -0.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0365   -1.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4490   -0.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3220   -2.0524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.6075   -1.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4654   -1.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1154   -1.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7654   -1.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2904   -0.8149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2904   -2.4649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9404   -0.8149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9404   -2.4649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2904   -1.6399    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.9404   -1.6399    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.3487   -1.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9034   -2.7636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0784   -3.5886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7284   -3.5886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9034   -3.5886    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.9034   -4.4136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2529   -1.0566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8661   -1.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5885   -0.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5805   -1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8661   -2.4336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4090   -0.3891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2950   -1.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5806   -2.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2950   -2.4335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0094   -1.1960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1799   -5.3525    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.8944   -6.5900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8944   -5.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0378   -5.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6088   -5.3525    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.6088   -4.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3233   -5.7650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.3233   -6.5900    0.0000 O   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 48  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
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 52  1  0  0  0  0
 52 54  1  0  0  0  0
 54 51  1  0  0  0  0
 52 53  1  1  0  0  0
 54 55  1  6  0  0  0
M  END


  Mrv1652305122021022D          

 55 57  0  0  1  0            999 V2000
   26.4683   -1.3115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.8009   -0.8266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2134   -2.0961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.1334   -1.3115    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.3884   -2.0961    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.6983   -2.7636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7225   -5.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4654   -5.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0081   -5.7650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2937   -5.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5792   -5.7650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0365   -4.1150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2937   -4.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0365   -3.2900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6076   -3.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3220   -2.8774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7510   -2.0524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6240   -0.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0365   -1.6399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4490   -0.9255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3220   -2.0524    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.6075   -1.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4654   -1.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1154   -1.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.7654   -1.6399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2904   -0.8149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2904   -2.4649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9404   -0.8149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9404   -2.4649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2904   -1.6399    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.9404   -1.6399    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.3487   -1.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9034   -2.7636    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0784   -3.5886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7284   -3.5886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9034   -3.5886    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   24.9034   -4.4136    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.2529   -1.0566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8661   -1.6086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5885   -0.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5805   -1.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8661   -2.4336    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4090   -0.3891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.2950   -1.6085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5806   -2.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2950   -2.4335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.0094   -1.1960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.1799   -5.3525    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   21.8944   -6.5900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8944   -5.7650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0378   -5.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6088   -5.3525    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.6088   -4.5275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3233   -5.7650    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.3233   -6.5900    0.0000 O   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 48  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
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 50  1  0  0  0  0
 50 49  2  0  0  0  0
 50 52  1  0  0  0  0
 52 54  1  0  0  0  0
 54 51  1  0  0  0  0
 52 53  1  1  0  0  0
 54 55  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0001356

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](O)[C@H](C)C(=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/C26H44N7O18P3S/c1-13(14(2)34)25(39)55-8-7-28-16(35)5-6-29-23(38)20(37)26(3,4)10-48-54(45,46)51-53(43,44)47-9-15-19(50-52(40,41)42)18(36)24(49-15)33-12-32-17-21(27)30-11-31-22(17)33/h11-15,18-20,24,34,36-37H,5-10H2,1-4H3,(H,28,35)(H,29,38)(H,43,44)(H,45,46)(H2,27,30,31)(H2,40,41,42)/t13-,14-,15+,18+,19+,20-,24+/m0/s1

> <INCHI_KEY>
PEKYNTFSOBAABV-LQUDNSJZSA-N

> <FORMULA>
C26H44N7O18P3S

> <MOLECULAR_WEIGHT>
867.65

> <EXACT_MASS>
867.167639773

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
76.50908617356865

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-({2-[(2-{[(2S,3S)-3-hydroxy-2-methylbutanoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.48

> <JCHEM_LOGP>
-5.502293119814627

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776186

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398224

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
383.85999999999996

> <JCHEM_REFRACTIVITY>
187.6029

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
invanz

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/C%5BC@H%5D(O)%5BC@H%5D(C)C(=O)S...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:98})
 99101  0  0  0  0  0  0  0  0999 V2000
   17.0900   -4.2365    0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8546   -3.4232    0.6804 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1665   -2.5093    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0335   -4.1965    1.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0606   -3.0646   -0.5773 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7487   -3.9785   -1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
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   16.7781   -5.1504   -0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7163   -3.6466   -0.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.6557   -4.4919    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7189   -5.0259    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.2516   -1.3227   -1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8198   -2.8160   -1.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3740   -1.9811   -2.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1084   -1.5526    0.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9613    1.0604    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8995    2.5642    0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7469    3.0503   -1.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8089    1.5465   -1.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4433    3.0827    0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8734    3.4833    1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535    3.0074   -2.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4062    2.9239   -1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1807    4.5047   -1.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6798    1.9402    1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3649    1.3657    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0031    1.5849   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3081    3.9326    2.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542    4.9967    0.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9122    2.3361    3.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4079    1.2316    3.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8800    0.9521    1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8857    2.1430    0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7198   -2.9744   -1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1386    2.9950   -2.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3998    1.8954   -4.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4323   -2.5532    2.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
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 62 99  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 12-MAY-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-MAY-20         0                                  
HETATM    1  C   UNK     0      49.407  -2.448   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      48.162  -1.543   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      48.932  -3.913   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      46.916  -2.448   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      47.392  -3.913   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      49.837  -5.159   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      36.815  -9.991   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      38.202 -10.761   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      35.482 -10.761   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      34.148  -9.991   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      32.815 -10.761   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      35.535  -7.681   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.148  -8.451   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      35.535  -6.141   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      32.868  -6.141   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      34.201  -5.371   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      36.869  -3.831   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.765  -1.728   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      35.535  -3.061   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      36.305  -1.728   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      34.201  -3.831   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      32.867  -3.061   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      38.202  -3.061   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      41.282  -3.061   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      44.362  -3.061   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      39.742  -1.521   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      39.742  -4.601   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      42.822  -1.521   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      42.822  -4.601   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      39.742  -3.061   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      42.822  -3.061   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      45.451  -1.972   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      46.486  -5.159   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      44.946  -6.699   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      48.026  -6.699   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      46.486  -6.699   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      46.486  -8.239   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      50.872  -1.972   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      52.017  -3.003   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      51.499  -0.565   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      53.350  -2.233   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      52.017  -4.543   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      53.030  -0.726   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      54.684  -3.003   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      53.350  -5.313   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      54.684  -4.543   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      56.018  -2.233   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      39.536  -9.991   0.000  0.00  0.00           S+0
HETATM   49  O   UNK     0      40.870 -12.301   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      40.870 -10.761   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      44.871  -9.991   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      42.203  -9.991   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      42.203  -8.451   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      43.537 -10.761   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      43.537 -12.301   0.000  0.00  0.00           O+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   48                                                       
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   47                                                  
CONECT   45   42   46                                                       
CONECT   46   44   45                                                       
CONECT   47   44                                                            
CONECT   48    8   50                                                       
CONECT   49   50                                                            
CONECT   50   48   49   52                                                  
CONECT   51   54                                                            
CONECT   52   50   54   53                                                  
CONECT   53   52                                                            
CONECT   54   52   51   55                                                  
CONECT   55   54                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/C%5BC@H%5D(O)%5BC@H%5D(C)C(=O)S... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1      17.090  -4.237   0.289  1.00  0.00           C  
HETATM    2  C   UNL     1      15.855  -3.423   0.680  1.00  0.00           C  
HETATM    3  H   UNL     1      16.166  -2.509   1.186  1.00  0.00           H  
HETATM    4  O   UNL     1      15.034  -4.197   1.558  1.00  0.00           O  
HETATM    5  C   UNL     1      15.061  -3.065  -0.577  1.00  0.00           C  
HETATM    6  H   UNL     1      14.749  -3.978  -1.083  1.00  0.00           H  
HETATM    7  C   UNL     1      15.940  -2.237  -1.517  1.00  0.00           C  
HETATM    8  C   UNL     1      13.844  -2.264  -0.192  1.00  0.00           C  
HETATM    9  O   UNL     1      13.632  -2.005   0.975  1.00  0.00           O  
HETATM   10  S   UNL     1      12.760  -1.718  -1.400  1.00  0.00           S  
HETATM   11  C   UNL     1      11.550  -0.852  -0.369  1.00  0.00           C  
HETATM   12  C   UNL     1      10.452  -0.263  -1.256  1.00  0.00           C  
HETATM   13  N   UNL     1       9.473   0.438  -0.422  1.00  0.00           N  
HETATM   14  C   UNL     1       8.410   1.040  -0.992  1.00  0.00           C  
HETATM   15  O   UNL     1       8.264   1.000  -2.195  1.00  0.00           O  
HETATM   16  C   UNL     1       7.403   1.761  -0.133  1.00  0.00           C  
HETATM   17  C   UNL     1       6.305   2.350  -1.021  1.00  0.00           C  
HETATM   18  N   UNL     1       5.326   3.051  -0.187  1.00  0.00           N  
HETATM   19  C   UNL     1       4.263   3.652  -0.756  1.00  0.00           C  
HETATM   20  O   UNL     1       4.165   3.693  -1.964  1.00  0.00           O  
HETATM   21  C   UNL     1       3.196   4.274   0.108  1.00  0.00           C  
HETATM   22  H   UNL     1       2.976   5.279  -0.253  1.00  0.00           H  
HETATM   23  O   UNL     1       3.658   4.343   1.458  1.00  0.00           O  
HETATM   24  C   UNL     1       1.928   3.420   0.046  1.00  0.00           C  
HETATM   25  C   UNL     1       1.351   3.467  -1.371  1.00  0.00           C  
HETATM   26  C   UNL     1       2.268   1.974   0.410  1.00  0.00           C  
HETATM   27  C   UNL     1       0.897   3.966   1.035  1.00  0.00           C  
HETATM   28  O   UNL     1      -0.288   3.169   0.977  1.00  0.00           O  
HETATM   29  P   UNL     1      -1.584   3.457   1.887  1.00  0.00           P  
HETATM   30  O   UNL     1      -1.212   3.232   3.438  1.00  0.00           O  
HETATM   31  O   UNL     1      -2.029   4.854   1.684  1.00  0.00           O  
HETATM   32  O   UNL     1      -2.769   2.450   1.468  1.00  0.00           O  
HETATM   33  P   UNL     1      -4.367   2.461   1.662  1.00  0.00           P  
HETATM   34  O   UNL     1      -4.724   2.100   3.190  1.00  0.00           O  
HETATM   35  O   UNL     1      -4.894   3.805   1.337  1.00  0.00           O  
HETATM   36  O   UNL     1      -5.034   1.371   0.683  1.00  0.00           O  
HETATM   37  C   UNL     1      -6.447   1.211   0.545  1.00  0.00           C  
HETATM   38  C   UNL     1      -6.738   0.094  -0.459  1.00  0.00           C  
HETATM   39  H   UNL     1      -6.224   0.297  -1.399  1.00  0.00           H  
HETATM   40  O   UNL     1      -6.302  -1.168   0.073  1.00  0.00           O  
HETATM   41  C   UNL     1      -7.228  -2.169  -0.403  1.00  0.00           C  
HETATM   42  H   UNL     1      -7.007  -2.434  -1.437  1.00  0.00           H  
HETATM   43  C   UNL     1      -8.605  -1.465  -0.302  1.00  0.00           C  
HETATM   44  H   UNL     1      -8.989  -1.507   0.718  1.00  0.00           H  
HETATM   45  O   UNL     1      -9.539  -2.038  -1.220  1.00  0.00           O  
HETATM   46  C   UNL     1      -8.256  -0.008  -0.704  1.00  0.00           C  
HETATM   47  H   UNL     1      -8.793   0.701  -0.074  1.00  0.00           H  
HETATM   48  O   UNL     1      -8.563   0.217  -2.082  1.00  0.00           O  
HETATM   49  P   UNL     1      -9.589   1.355  -2.576  1.00  0.00           P  
HETATM   50  O   UNL     1      -8.993   2.807  -2.216  1.00  0.00           O  
HETATM   51  O   UNL     1      -9.793   1.239  -4.169  1.00  0.00           O  
HETATM   52  O   UNL     1     -10.892   1.175  -1.898  1.00  0.00           O  
HETATM   53  N   UNL     1      -7.187  -3.357   0.452  1.00  0.00           N  
HETATM   54  C   UNL     1      -6.781  -3.402   1.753  1.00  0.00           C  
HETATM   55  N   UNL     1      -6.875  -4.618   2.207  1.00  0.00           N  
HETATM   56  C   UNL     1      -7.346  -5.429   1.229  1.00  0.00           C  
HETATM   57  C   UNL     1      -7.558  -4.629   0.093  1.00  0.00           C  
HETATM   58  N   UNL     1      -8.024  -5.192  -1.016  1.00  0.00           N  
HETATM   59  C   UNL     1      -8.286  -6.482  -1.055  1.00  0.00           C  
HETATM   60  N   UNL     1      -8.104  -7.274  -0.013  1.00  0.00           N  
HETATM   61  C   UNL     1      -7.645  -6.799   1.140  1.00  0.00           C  
HETATM   62  N   UNL     1      -7.456  -7.637   2.225  1.00  0.00           N  
HETATM   63  H   UNL     1      16.778  -5.150  -0.217  1.00  0.00           H  
HETATM   64  H   UNL     1      17.716  -3.647  -0.380  1.00  0.00           H  
HETATM   65  H   UNL     1      17.656  -4.492   1.185  1.00  0.00           H  
HETATM   66  H   UNL     1      14.719  -5.026   1.173  1.00  0.00           H  
HETATM   67  H   UNL     1      16.252  -1.323  -1.011  1.00  0.00           H  
HETATM   68  H   UNL     1      16.820  -2.816  -1.796  1.00  0.00           H  
HETATM   69  H   UNL     1      15.374  -1.981  -2.413  1.00  0.00           H  
HETATM   70  H   UNL     1      11.108  -1.553   0.340  1.00  0.00           H  
HETATM   71  H   UNL     1      12.047  -0.049   0.176  1.00  0.00           H  
HETATM   72  H   UNL     1      10.894   0.437  -1.965  1.00  0.00           H  
HETATM   73  H   UNL     1       9.956  -1.066  -1.801  1.00  0.00           H  
HETATM   74  H   UNL     1       9.590   0.470   0.540  1.00  0.00           H  
HETATM   75  H   UNL     1       6.961   1.060   0.575  1.00  0.00           H  
HETATM   76  H   UNL     1       7.899   2.564   0.411  1.00  0.00           H  
HETATM   77  H   UNL     1       6.747   3.050  -1.730  1.00  0.00           H  
HETATM   78  H   UNL     1       5.809   1.546  -1.566  1.00  0.00           H  
HETATM   79  H   UNL     1       5.443   3.083   0.775  1.00  0.00           H  
HETATM   80  H   UNL     1       3.873   3.483   1.845  1.00  0.00           H  
HETATM   81  H   UNL     1       2.054   3.007  -2.065  1.00  0.00           H  
HETATM   82  H   UNL     1       0.406   2.924  -1.396  1.00  0.00           H  
HETATM   83  H   UNL     1       1.181   4.505  -1.659  1.00  0.00           H  
HETATM   84  H   UNL     1       2.680   1.940   1.419  1.00  0.00           H  
HETATM   85  H   UNL     1       1.365   1.366   0.365  1.00  0.00           H  
HETATM   86  H   UNL     1       3.003   1.585  -0.295  1.00  0.00           H  
HETATM   87  H   UNL     1       1.308   3.933   2.044  1.00  0.00           H  
HETATM   88  H   UNL     1       0.654   4.997   0.776  1.00  0.00           H  
HETATM   89  H   UNL     1      -0.912   2.336   3.644  1.00  0.00           H  
HETATM   90  H   UNL     1      -4.408   1.232   3.473  1.00  0.00           H  
HETATM   91  H   UNL     1      -6.880   0.952   1.512  1.00  0.00           H  
HETATM   92  H   UNL     1      -6.886   2.143   0.189  1.00  0.00           H  
HETATM   93  H   UNL     1      -9.720  -2.974  -1.064  1.00  0.00           H  
HETATM   94  H   UNL     1      -8.139   2.995  -2.628  1.00  0.00           H  
HETATM   95  H   UNL     1     -10.400   1.895  -4.537  1.00  0.00           H  
HETATM   96  H   UNL     1      -6.432  -2.553   2.322  1.00  0.00           H  
HETATM   97  H   UNL     1      -8.665  -6.908  -1.972  1.00  0.00           H  
HETATM   98  H   UNL     1      -7.660  -8.582   2.149  1.00  0.00           H  
HETATM   99  H   UNL     1      -7.120  -7.279   3.062  1.00  0.00           H  
CONECT    1    2   63   64   65                                       
CONECT    2    1    3    4    5                                       
CONECT    3    2                                                      
CONECT    4    2   66                                                 
CONECT    5    2    6    7    8                                       
CONECT    6    5                                                      
CONECT    7    5   67   68   69                                       
CONECT    8    5    9    9   10                                       
CONECT    9    8    8                                                 
CONECT   10    8   11                                                 
CONECT   11   10   12   70   71                                       
CONECT   12   11   13   72   73                                       
CONECT   13   12   14   74                                            
CONECT   14   13   15   15   16                                       
CONECT   15   14   14                                                 
CONECT   16   14   17   75   76                                       
CONECT   17   16   18   77   78                                       
CONECT   18   17   19   79                                            
CONECT   19   18   20   20   21                                       
CONECT   20   19   19                                                 
CONECT   21   19   22   23   24                                       
CONECT   22   21                                                      
CONECT   23   21   80                                                 
CONECT   24   21   25   26   27                                       
CONECT   25   24   81   82   83                                       
CONECT   26   24   84   85   86                                       
CONECT   27   24   28   87   88                                       
CONECT   28   27   29                                                 
CONECT   29   28   30   31   31                                       
CONECT   29   32                                                      
CONECT   30   29   89                                                 
CONECT   31   29   29                                                 
CONECT   32   29   33                                                 
CONECT   33   32   34   35   35                                       
CONECT   33   36                                                      
CONECT   34   33   90                                                 
CONECT   35   33   33                                                 
CONECT   36   33   37                                                 
CONECT   37   36   38   91   92                                       
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   93                                                 
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   94                                                 
CONECT   51   49   95                                                 
CONECT   52   49   49                                                 
CONECT   53   41   54   57                                            
CONECT   54   53   55   55   96                                       
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   97                                       
CONECT   60   59   61   61                                            
CONECT   61   60   60   56   62                                       
CONECT   62   61   98   99                                            
CONECT   63    1                                                      
CONECT   64    1                                                      
CONECT   65    1                                                      
CONECT   66    4                                                      
CONECT   67    7                                                      
CONECT   68    7                                                      
CONECT   69    7                                                      
CONECT   70   11                                                      
CONECT   71   11                                                      
CONECT   72   12                                                      
CONECT   73   12                                                      
CONECT   74   13                                                      
CONECT   75   16                                                      
CONECT   76   16                                                      
CONECT   77   17                                                      
CONECT   78   17                                                      
CONECT   79   18                                                      
CONECT   80   23                                                      
CONECT   81   25                                                      
CONECT   82   25                                                      
CONECT   83   25                                                      
CONECT   84   26                                                      
CONECT   85   26                                                      
CONECT   86   26                                                      
CONECT   87   27                                                      
CONECT   88   27                                                      
CONECT   89   30                                                      
CONECT   90   34                                                      
CONECT   91   37                                                      
CONECT   92   37                                                      
CONECT   93   45                                                      
CONECT   94   50                                                      
CONECT   95   51                                                      
CONECT   96   54                                                      
CONECT   97   59                                                      
CONECT   98   62                                                      
CONECT   99   62                                                      
MASTER        0    0    0    0    0    0    0    0   99    0   99    0
END

https://cactus.nci.nih.gov/chemical/structure/C%5BC@H%5D(O)%5BC@H%5D(C)C(=O)S...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:98})
 99101  0  0  0  0  0  0  0  0999 V2000
   17.0900   -4.2365    0.2889 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8546   -3.4232    0.6804 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1665   -2.5093    1.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.0335   -4.1965    1.5577 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0606   -3.0646   -0.5773 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7487   -3.9785   -1.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9397   -2.2366   -1.5167 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8437   -2.2635   -0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6323   -2.0047    0.9746 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7597   -1.7185   -1.3996 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.5504   -0.8519   -0.3689 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4521   -0.2633   -1.2565 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4733    0.4382   -0.4222 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4101    1.0395   -0.9917 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2637    1.0000   -2.1950 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4032    1.7610   -0.1334 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3049    2.3497   -1.0212 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3262    3.0511   -0.1868 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2629    3.6525   -0.7564 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1647    3.6935   -1.9645 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1962    4.2739    0.1079 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9761    5.2786   -0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6580    4.3431    1.4585 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9280    3.4203    0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    3.4675   -1.3705 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2684    1.9738    0.4096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8968    3.9663    1.0353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2879    3.1689    0.9771 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5842    3.4570    1.8872 P   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2124    3.2318    3.4375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0288    4.8540    1.6844 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7688    2.4505    1.4678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3670    2.4613    1.6624 P   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7240    2.1005    3.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945    3.8052    1.3366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0342    1.3711    0.6835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4474    1.2108    0.5452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7381    0.0939   -0.4594 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.2239    0.2974   -1.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3023   -1.1681    0.0733 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2275   -2.1689   -0.4032 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.0071   -2.4340   -1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6049   -1.4653   -0.3019 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.9889   -1.5072    0.7175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5385   -2.0375   -1.2199 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2561   -0.0083   -0.7044 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.7925    0.7007   -0.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5634    0.2172   -2.0816 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5888    1.3555   -2.5763 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9933    2.8074   -2.2164 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7927    1.2388   -4.1690 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8915    1.1746   -1.8976 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1874   -3.3574    0.4524 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7812   -3.4019    1.7528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8752   -4.6181    2.2065 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3465   -5.4288    1.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5576   -4.6288    0.0934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0243   -5.1925   -1.0162 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2863   -6.4818   -1.0547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1039   -7.2738   -0.0135 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6446   -6.7994    1.1397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4564   -7.6370    2.2251 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7781   -5.1504   -0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.7163   -3.6466   -0.3803 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.6557   -4.4919    1.1850 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.7189   -5.0259    1.1728 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.2516   -1.3227   -1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.8198   -2.8160   -1.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3740   -1.9811   -2.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.1084   -1.5526    0.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.0466   -0.0488    0.1761 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8941    0.4373   -1.9650 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9559   -1.0664   -1.8014 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5904    0.4698    0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9613    1.0604    0.5750 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8995    2.5642    0.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7469    3.0503   -1.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8089    1.5465   -1.5661 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4433    3.0827    0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8734    3.4833    1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0535    3.0074   -2.0650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4062    2.9239   -1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1807    4.5047   -1.6593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6798    1.9402    1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3649    1.3657    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0031    1.5849   -0.2954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3081    3.9326    2.0441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6542    4.9967    0.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9122    2.3361    3.6438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4079    1.2316    3.4733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8800    0.9521    1.5116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8857    2.1430    0.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7198   -2.9744   -1.0639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1386    2.9950   -2.6280 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3998    1.8954   -4.5370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4323   -2.5532    2.3224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6648   -6.9081   -1.9720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6603   -8.5823    2.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1205   -7.2789    3.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,3S)-3-Hydroxy-2-methylbutanoyl-coenzyme A	ChEBI
(S)-3-Hydroxy-2-methylbutyryl-CoA	ChEBI
(S,S)-3-Hydroxy-2-methylbutanoyl-coenzyme A	ChEBI
(S,S)-3-Hydroxy-2-methylbutyryl-coenzyme A	ChEBI
2-Methyl-3-hydroxybutyryl-CoA	HMDB
2-Methyl-3-hydroxybutyryl-coenzyme A	HMDB
3-Hydroxy-2-methylbutyryl-CoA	HMDB
3-Hydroxy-2-methylbutyryl-coenzyme A	HMDB

Chemical Formula

C₂₆H₄₄N₇O₁₈P₃S

Average Molecular Weight

867.65

Monoisotopic Molecular Weight

867.167639773

IUPAC Name

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

Traditional Name

invanz

CAS Registry Number

1169932-06-2

SMILES

C[C@H](O)[C@H](C)C(=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/C26H44N7O18P3S/c1-13(14(2)34)25(39)55-8-7-28-16(35)5-6-29-23(38)20(37)26(3,4)10-48-54(45,46)51-53(43,44)47-9-15-19(50-52(40,41)42)18(36)24(49-15)33-12-32-17-21(27)30-11-31-22(17)33/h11-15,18-20,24,34,36-37H,5-10H2,1-4H3,(H,28,35)(H,29,38)(H,43,44)(H,45,46)(H2,27,30,31)(H2,40,41,42)/t13-,14-,15+,18+,19+,20-,24+/m0/s1

InChI Key

PEKYNTFSOBAABV-LQUDNSJZSA-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

3-hydroxy fatty acyl-CoA (CHEBI:15449 )
hydroxybutanoyl-CoA (CHEBI:15449 )
methylbutanoyl-CoA (CHEBI:15449 )
(S)-3-hydroxyacyl-CoA (CHEBI:15449 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Urine

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical process:

Cellular process:

Cell signaling

Biochemical pathway:

Role

Biological role:

Industrial application:

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	3.96 g/L	ALOGPS
logP	-0.48	ALOGPS
logP	-5.5	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	383.86 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	187.6 m³·mol⁻¹	ChemAxon
Polarizability	76.51 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)	splash10-002k-9011173110-2c38a2fa9b466785edce	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, Negative	splash10-014i-0000000090-f99797af7605477f8118	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00li-9200001110-c3ad6043a456b94e2991	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004r-6103703920-89a34df340ee562cb16f	2021-09-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000000190-c7660cb8074cdb7785f2	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1900002440-0c30d5ed7ad3fc1eb9fc	2021-09-07	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-0039000000-ac37b68d2000665090c6	2021-09-07	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/Pathwhiz	KEGG
Valine, Leucine and Isoleucine Degradation
Beta-Ketothiolase Deficiency		Not Available
2-Methyl-3-Hydroxybutryl CoA Dehydrogenase Deficiency		Not Available
Propionic Acidemia		Not Available
3-Hydroxy-3-Methylglutaryl-CoA Lyase Deficiency		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

FDB022575

KNApSAcK ID

Not Available

Chemspider ID

10140213

KEGG Compound ID

C04405

BioCyc ID

2-METHYL-3-HYDROXY-BUTYRYL-COA

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11966220

PDB ID

Not Available

ChEBI ID

15449

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Sutton VR, O'Brien WE, Clark GD, Kim J, Wanders RJ: 3-Hydroxy-2-methylbutyryl-CoA dehydrogenase deficiency. J Inherit Metab Dis. 2003;26(1):69-71. [PubMed:12872843 ]

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

Reactions

2-Methyl-3-hydroxybutyryl-CoA + NAD → 2-Methylacetoacetyl-CoA + NADH	details
2-Methyl-3-hydroxybutyryl-CoA + NAD → 2-Methylacetoacetyl-CoA + NADH + Hydrogen Ion	details

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

2-Methyl-3-hydroxybutyryl-CoA + NAD → 2-Methylacetoacetyl-CoA + NADH + Hydrogen Ion	details
2-Methyl-3-hydroxybutyryl-CoA → Tiglyl-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

2-Methyl-3-hydroxybutyryl-CoA + NAD → 2-Methylacetoacetyl-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

2-Methyl-3-hydroxybutyryl-CoA → Tiglyl-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

2-Methyl-3-hydroxybutyryl-CoA → Tiglyl-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 2-Methyl-3-hydroxybutyryl-CoA (HMDB0001356)

MOL for HMDB0001356 (2-Methyl-3-hydroxybutyryl-CoA)

3D MOL for HMDB0001356 (2-Methyl-3-hydroxybutyryl-CoA)

3D SDF for HMDB0001356 (2-Methyl-3-hydroxybutyryl-CoA)

3D-SDF for HMDB0001356 (2-Methyl-3-hydroxybutyryl-CoA)

PDB for HMDB0001356 (2-Methyl-3-hydroxybutyryl-CoA)

3D PDB for HMDB0001356 (2-Methyl-3-hydroxybutyryl-CoA)

SMILES for HMDB0001356 (2-Methyl-3-hydroxybutyryl-CoA)

INCHI for HMDB0001356 (2-Methyl-3-hydroxybutyryl-CoA)

Structure for HMDB0001356 (2-Methyl-3-hydroxybutyryl-CoA)

3D Structure for HMDB0001356 (2-Methyl-3-hydroxybutyryl-CoA)

GC-MS

LC-MS/MS

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions