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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

2006-05-22 14:17:34 UTC

Update Date

2021-09-14 14:59:50 UTC

HMDB ID

HMDB0002054

Secondary Accession Numbers

HMDB0000993
HMDB0002371
HMDB0006871
HMDB00993
HMDB02054
HMDB02371
HMDB06871

Metabolite Identification

Common Name

Tiglyl-CoA

Description

2-methylcrotonoyl-CoA, also known as tiglyl-CoA or tiglyl-coenzyme A, belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain. Thus, 2-methylcrotonoyl-CoA is considered to be a fatty ester lipid molecule. 2-methylcrotonoyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306302020402D          

 54 56  0  0  1  0            999 V2000
   25.1003   -1.9774    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.4329   -1.4925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8454   -2.7620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.7654   -1.9774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.0204   -2.7620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.3303   -3.4295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3546   -6.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0974   -6.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6400   -6.4309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9257   -6.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2112   -6.4309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6685   -4.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9257   -5.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6685   -3.9559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2396   -3.9559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9540   -3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3830   -2.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2560   -1.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6685   -2.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0810   -1.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9540   -2.7183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2395   -2.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0974   -2.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7474   -2.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3974   -2.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9224   -1.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9224   -3.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5723   -1.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5723   -3.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9224   -2.3058    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.5723   -2.3058    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.9808   -1.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5354   -3.4295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7104   -4.2545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3603   -4.2545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5354   -4.2545    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.5354   -5.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8848   -1.7225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4981   -2.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2205   -0.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2125   -1.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4981   -3.0995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0410   -1.0550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9270   -2.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2126   -3.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9270   -3.0993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6414   -1.8619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8119   -6.0184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.5264   -7.2559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5264   -6.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9553   -6.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6698   -6.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2408   -6.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2408   -5.1933    0.0000 C   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 53  1  0  0  0  0
 53 51  2  0  0  0  0
 51 52  1  0  0  0  0
 53 54  1  0  0  0  0
M  END


  Mrv1652306302020402D          

 54 56  0  0  1  0            999 V2000
   25.1003   -1.9774    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.4329   -1.4925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8454   -2.7620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.7654   -1.9774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   24.0204   -2.7620    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.3303   -3.4295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3546   -6.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0974   -6.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6400   -6.4309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9257   -6.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2112   -6.4309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6685   -4.7809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9257   -5.1933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6685   -3.9559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2396   -3.9559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9540   -3.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3830   -2.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2560   -1.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6685   -2.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0810   -1.5914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9540   -2.7183    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.2395   -2.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0974   -2.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7474   -2.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.3974   -2.3058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9224   -1.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9224   -3.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5723   -1.4807    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5723   -3.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9224   -2.3058    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.5723   -2.3058    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   22.9808   -1.7225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5354   -3.4295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.7104   -4.2545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.3603   -4.2545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5354   -4.2545    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.5354   -5.0795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8848   -1.7225    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.4981   -2.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2205   -0.9688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2125   -1.8620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4981   -3.0995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.0410   -1.0550    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9270   -2.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2126   -3.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9270   -3.0993    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.6414   -1.8619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8119   -6.0184    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.5264   -7.2559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5264   -6.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9553   -6.4309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6698   -6.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2408   -6.0184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2408   -5.1933    0.0000 C   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 53  1  0  0  0  0
 53 51  2  0  0  0  0
 51 52  1  0  0  0  0
 53 54  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002054

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C(/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/C26H42N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h5,12-13,15,18-20,24,35-36H,6-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/b14-5+/t15-,18-,19-,20+,24-/m1/s1

> <INCHI_KEY>
PMWATMXOQQZNBX-DKBZLLMOSA-N

> <FORMULA>
C26H42N7O17P3S

> <MOLECULAR_WEIGHT>
849.64

> <EXACT_MASS>
849.157075088

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
96

> <JCHEM_AVERAGE_POLARIZABILITY>
74.98361297678173

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.02

> <JCHEM_LOGP>
-4.109807288814626

> <ALOGPS_LOGS>
-2.38

> <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>
363.62999999999994

> <JCHEM_REFRACTIVITY>
186.8863

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.56e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methylcrotonyl-coenzyme A

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/C%5CC=C(/C)C(=O)SCCNC(=O)CCNC(=...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:95})
 96 98  0  0  0  0  0  0  0  0999 V2000
   17.3728    4.6530   -0.3734 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1669    3.8195   -0.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3422    3.4082    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6136    3.7754    1.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1651    2.5948   -0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9460    2.2982   -1.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0725    2.0498    1.1648 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.8687    1.1326    0.1719 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7903    0.5502    1.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8160   -0.1923    0.2841 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.2835    7.5006   -2.4104 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0165    4.0936    0.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.9246    4.8927   -1.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.0496    5.5751    0.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9724    3.5563   -1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1208    4.7193    1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2284    2.9933    2.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6880    3.8794    1.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
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   12.3738    0.3232   -0.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2522   -0.1222    1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
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    8.2726   -2.3690   -0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2495   -3.4004   -1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612   -2.8457    2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8058   -2.8107    1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6116   -4.3693    1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0325   -1.8673   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182   -1.2865   -0.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -1.4575    0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6909   -3.9009   -1.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -4.9399   -0.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5741   -2.3908   -3.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0874   -1.3443   -3.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5441   -1.0530   -1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5147   -2.2057   -0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4283    2.8940    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7714   -2.0632    4.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0499   -0.2338    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
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 59 95  1  0  0  0  0
 59 96  1  0  0  0  0
M  END
$$$$

HEADER    PROTEIN                                 30-JUN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-20         0                                  
HETATM    1  C   UNK     0      46.854  -3.691   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      45.608  -2.786   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      46.378  -5.156   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      44.362  -3.691   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      44.838  -5.156   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      47.283  -6.402   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      34.262 -11.234   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      35.648 -12.004   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      32.928 -12.004   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      31.595 -11.234   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      30.261 -12.004   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      32.981  -8.924   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      31.595  -9.694   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      32.981  -7.384   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      30.314  -7.384   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      31.647  -6.614   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      34.315  -5.074   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.211  -2.971   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.981  -4.304   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.751  -2.971   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      31.647  -5.074   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      30.314  -4.304   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      35.648  -4.304   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      38.728  -4.304   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      41.808  -4.304   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      37.188  -2.764   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      37.188  -5.844   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      40.268  -2.764   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      40.268  -5.844   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      37.188  -4.304   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      40.268  -4.304   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      42.897  -3.215   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      43.933  -6.402   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      42.393  -7.942   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      45.473  -7.942   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      43.933  -7.942   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      43.933  -9.482   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      48.318  -3.215   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      49.463  -4.246   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      48.945  -1.808   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      50.797  -3.476   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      49.463  -5.786   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      50.477  -1.969   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      52.130  -4.246   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      50.797  -6.556   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      52.130  -5.785   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      53.464  -3.476   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      36.982 -11.234   0.000  0.00  0.00           S+0
HETATM   49  O   UNK     0      38.316 -13.544   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      38.316 -12.004   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      40.983 -12.004   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      42.317 -11.234   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      39.649 -11.234   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      39.649  -9.694   0.000  0.00  0.00           C+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   53                                                  
CONECT   51   53   52                                                       
CONECT   52   51                                                            
CONECT   53   50   51   54                                                  
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/C%5CC=C(/C)C(=O)SCCNC(=O)CCNC(=... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1      17.373   4.653  -0.373  1.00  0.00           C  
HETATM    2  C   UNL     1      16.167   3.820  -0.723  1.00  0.00           C  
HETATM    3  C   UNL     1      15.342   3.408   0.236  1.00  0.00           C  
HETATM    4  C   UNL     1      15.614   3.775   1.672  1.00  0.00           C  
HETATM    5  C   UNL     1      14.165   2.595  -0.105  1.00  0.00           C  
HETATM    6  O   UNL     1      13.946   2.298  -1.265  1.00  0.00           O  
HETATM    7  S   UNL     1      13.072   2.050   1.165  1.00  0.00           S  
HETATM    8  C   UNL     1      11.869   1.133   0.172  1.00  0.00           C  
HETATM    9  C   UNL     1      10.790   0.550   1.088  1.00  0.00           C  
HETATM   10  N   UNL     1       9.816  -0.192   0.284  1.00  0.00           N  
HETATM   11  C   UNL     1       8.770  -0.796   0.882  1.00  0.00           C  
HETATM   12  O   UNL     1       8.635  -0.725   2.085  1.00  0.00           O  
HETATM   13  C   UNL     1       7.768  -1.560   0.055  1.00  0.00           C  
HETATM   14  C   UNL     1       6.689  -2.142   0.971  1.00  0.00           C  
HETATM   15  N   UNL     1       5.715  -2.885   0.167  1.00  0.00           N  
HETATM   16  C   UNL     1       4.668  -3.488   0.765  1.00  0.00           C  
HETATM   17  O   UNL     1       4.583  -3.497   1.975  1.00  0.00           O  
HETATM   18  C   UNL     1       3.604  -4.153  -0.070  1.00  0.00           C  
HETATM   19  H   UNL     1       3.406  -5.151   0.321  1.00  0.00           H  
HETATM   20  O   UNL     1       4.054  -4.253  -1.423  1.00  0.00           O  
HETATM   21  C   UNL     1       2.322  -3.321  -0.018  1.00  0.00           C  
HETATM   22  C   UNL     1       1.760  -3.338   1.405  1.00  0.00           C  
HETATM   23  C   UNL     1       2.632  -1.879  -0.427  1.00  0.00           C  
HETATM   24  C   UNL     1       1.290  -3.913  -0.981  1.00  0.00           C  
HETATM   25  O   UNL     1       0.092  -3.136  -0.933  1.00  0.00           O  
HETATM   26  P   UNL     1      -1.208  -3.473  -1.821  1.00  0.00           P  
HETATM   27  O   UNL     1      -0.856  -3.285  -3.381  1.00  0.00           O  
HETATM   28  O   UNL     1      -1.625  -4.871  -1.574  1.00  0.00           O  
HETATM   29  O   UNL     1      -2.406  -2.476  -1.417  1.00  0.00           O  
HETATM   30  P   UNL     1      -4.006  -2.521  -1.595  1.00  0.00           P  
HETATM   31  O   UNL     1      -4.385  -2.210  -3.128  1.00  0.00           O  
HETATM   32  O   UNL     1      -4.505  -3.864  -1.225  1.00  0.00           O  
HETATM   33  O   UNL     1      -4.683  -1.415  -0.640  1.00  0.00           O  
HETATM   34  C   UNL     1      -6.097  -1.276  -0.491  1.00  0.00           C  
HETATM   35  C   UNL     1      -6.398  -0.137   0.484  1.00  0.00           C  
HETATM   36  H   UNL     1      -5.870  -0.304   1.423  1.00  0.00           H  
HETATM   37  O   UNL     1      -5.990   1.117  -0.088  1.00  0.00           O  
HETATM   38  C   UNL     1      -6.929   2.115   0.369  1.00  0.00           C  
HETATM   39  H   UNL     1      -6.703   2.413   1.393  1.00  0.00           H  
HETATM   40  C   UNL     1      -8.294   1.384   0.303  1.00  0.00           C  
HETATM   41  H   UNL     1      -8.689   1.390  -0.713  1.00  0.00           H  
HETATM   42  O   UNL     1      -9.229   1.965   1.214  1.00  0.00           O  
HETATM   43  C   UNL     1      -7.915  -0.055   0.743  1.00  0.00           C  
HETATM   44  H   UNL     1      -8.445  -0.791   0.138  1.00  0.00           H  
HETATM   45  O   UNL     1      -8.204  -0.246   2.129  1.00  0.00           O  
HETATM   46  P   UNL     1      -9.204  -1.388   2.667  1.00  0.00           P  
HETATM   47  O   UNL     1      -9.190  -1.398   4.276  1.00  0.00           O  
HETATM   48  O   UNL     1     -10.696  -1.084   2.144  1.00  0.00           O  
HETATM   49  O   UNL     1      -8.763  -2.708   2.161  1.00  0.00           O  
HETATM   50  N   UNL     1      -6.919   3.279  -0.520  1.00  0.00           N  
HETATM   51  C   UNL     1      -6.527   3.293  -1.825  1.00  0.00           C  
HETATM   52  N   UNL     1      -6.647   4.494  -2.312  1.00  0.00           N  
HETATM   53  C   UNL     1      -7.123   5.324  -1.353  1.00  0.00           C  
HETATM   54  C   UNL     1      -7.308   4.553  -0.193  1.00  0.00           C  
HETATM   55  N   UNL     1      -7.774   5.140   0.905  1.00  0.00           N  
HETATM   56  C   UNL     1      -8.059   6.425   0.909  1.00  0.00           C  
HETATM   57  N   UNL     1      -7.902   7.190  -0.156  1.00  0.00           N  
HETATM   58  C   UNL     1      -7.445   6.691  -1.300  1.00  0.00           C  
HETATM   59  N   UNL     1      -7.284   7.501  -2.410  1.00  0.00           N  
HETATM   60  H   UNL     1      18.017   4.094   0.306  1.00  0.00           H  
HETATM   61  H   UNL     1      17.925   4.893  -1.282  1.00  0.00           H  
HETATM   62  H   UNL     1      17.050   5.575   0.110  1.00  0.00           H  
HETATM   63  H   UNL     1      15.972   3.556  -1.752  1.00  0.00           H  
HETATM   64  H   UNL     1      15.121   4.719   1.905  1.00  0.00           H  
HETATM   65  H   UNL     1      15.228   2.993   2.326  1.00  0.00           H  
HETATM   66  H   UNL     1      16.688   3.879   1.823  1.00  0.00           H  
HETATM   67  H   UNL     1      11.407   1.805  -0.551  1.00  0.00           H  
HETATM   68  H   UNL     1      12.374   0.323  -0.355  1.00  0.00           H  
HETATM   69  H   UNL     1      11.252  -0.122   1.811  1.00  0.00           H  
HETATM   70  H   UNL     1      10.285   1.359   1.615  1.00  0.00           H  
HETATM   71  H   UNL     1       9.924  -0.249  -0.678  1.00  0.00           H  
HETATM   72  H   UNL     1       7.306  -0.887  -0.668  1.00  0.00           H  
HETATM   73  H   UNL     1       8.273  -2.369  -0.472  1.00  0.00           H  
HETATM   74  H   UNL     1       7.151  -2.814   1.694  1.00  0.00           H  
HETATM   75  H   UNL     1       6.184  -1.333   1.498  1.00  0.00           H  
HETATM   76  H   UNL     1       5.823  -2.942  -0.795  1.00  0.00           H  
HETATM   77  H   UNL     1       4.250  -3.400  -1.836  1.00  0.00           H  
HETATM   78  H   UNL     1       2.461  -2.846   2.078  1.00  0.00           H  
HETATM   79  H   UNL     1       0.806  -2.811   1.425  1.00  0.00           H  
HETATM   80  H   UNL     1       1.612  -4.369   1.724  1.00  0.00           H  
HETATM   81  H   UNL     1       3.033  -1.867  -1.441  1.00  0.00           H  
HETATM   82  H   UNL     1       1.718  -1.286  -0.390  1.00  0.00           H  
HETATM   83  H   UNL     1       3.367  -1.458   0.259  1.00  0.00           H  
HETATM   84  H   UNL     1       1.691  -3.901  -1.995  1.00  0.00           H  
HETATM   85  H   UNL     1       1.069  -4.940  -0.690  1.00  0.00           H  
HETATM   86  H   UNL     1      -0.574  -2.391  -3.615  1.00  0.00           H  
HETATM   87  H   UNL     1      -4.087  -1.344  -3.439  1.00  0.00           H  
HETATM   88  H   UNL     1      -6.544  -1.053  -1.460  1.00  0.00           H  
HETATM   89  H   UNL     1      -6.515  -2.206  -0.104  1.00  0.00           H  
HETATM   90  H   UNL     1      -9.428   2.894   1.033  1.00  0.00           H  
HETATM   91  H   UNL     1      -9.771  -2.063   4.670  1.00  0.00           H  
HETATM   92  H   UNL     1     -11.050  -0.234   2.438  1.00  0.00           H  
HETATM   93  H   UNL     1      -6.168   2.435  -2.374  1.00  0.00           H  
HETATM   94  H   UNL     1      -8.436   6.870   1.818  1.00  0.00           H  
HETATM   95  H   UNL     1      -7.504   8.444  -2.359  1.00  0.00           H  
HETATM   96  H   UNL     1      -6.950   7.125  -3.240  1.00  0.00           H  
CONECT    1    2   60   61   62                                       
CONECT    2    1    3    3   63                                       
CONECT    3    2    2    4    5                                       
CONECT    4    3   64   65   66                                       
CONECT    5    3    6    6    7                                       
CONECT    6    5    5                                                 
CONECT    7    5    8                                                 
CONECT    8    7    9   67   68                                       
CONECT    9    8   10   69   70                                       
CONECT   10    9   11   71                                            
CONECT   11   10   12   12   13                                       
CONECT   12   11   11                                                 
CONECT   13   11   14   72   73                                       
CONECT   14   13   15   74   75                                       
CONECT   15   14   16   76                                            
CONECT   16   15   17   17   18                                       
CONECT   17   16   16                                                 
CONECT   18   16   19   20   21                                       
CONECT   19   18                                                      
CONECT   20   18   77                                                 
CONECT   21   18   22   23   24                                       
CONECT   22   21   78   79   80                                       
CONECT   23   21   81   82   83                                       
CONECT   24   21   25   84   85                                       
CONECT   25   24   26                                                 
CONECT   26   25   27   28   28                                       
CONECT   26   29                                                      
CONECT   27   26   86                                                 
CONECT   28   26   26                                                 
CONECT   29   26   30                                                 
CONECT   30   29   31   32   32                                       
CONECT   30   33                                                      
CONECT   31   30   87                                                 
CONECT   32   30   30                                                 
CONECT   33   30   34                                                 
CONECT   34   33   35   88   89                                       
CONECT   35   34   36   37   43                                       
CONECT   36   35                                                      
CONECT   37   35   38                                                 
CONECT   38   37   39   40   50                                       
CONECT   39   38                                                      
CONECT   40   38   41   42   43                                       
CONECT   41   40                                                      
CONECT   42   40   90                                                 
CONECT   43   40   44   35   45                                       
CONECT   44   43                                                      
CONECT   45   43   46                                                 
CONECT   46   45   47   48   49                                       
CONECT   46   49                                                      
CONECT   47   46   91                                                 
CONECT   48   46   92                                                 
CONECT   49   46   46                                                 
CONECT   50   38   51   54                                            
CONECT   51   50   52   52   93                                       
CONECT   52   51   51   53                                            
CONECT   53   52   54   54   58                                       
CONECT   54   53   53   50   55                                       
CONECT   55   54   56   56                                            
CONECT   56   55   55   57   94                                       
CONECT   57   56   58   58                                            
CONECT   58   57   57   53   59                                       
CONECT   59   58   95   96                                            
CONECT   60    1                                                      
CONECT   61    1                                                      
CONECT   62    1                                                      
CONECT   63    2                                                      
CONECT   64    4                                                      
CONECT   65    4                                                      
CONECT   66    4                                                      
CONECT   67    8                                                      
CONECT   68    8                                                      
CONECT   69    9                                                      
CONECT   70    9                                                      
CONECT   71   10                                                      
CONECT   72   13                                                      
CONECT   73   13                                                      
CONECT   74   14                                                      
CONECT   75   14                                                      
CONECT   76   15                                                      
CONECT   77   20                                                      
CONECT   78   22                                                      
CONECT   79   22                                                      
CONECT   80   22                                                      
CONECT   81   23                                                      
CONECT   82   23                                                      
CONECT   83   23                                                      
CONECT   84   24                                                      
CONECT   85   24                                                      
CONECT   86   27                                                      
CONECT   87   31                                                      
CONECT   88   34                                                      
CONECT   89   34                                                      
CONECT   90   42                                                      
CONECT   91   47                                                      
CONECT   92   48                                                      
CONECT   93   51                                                      
CONECT   94   56                                                      
CONECT   95   59                                                      
CONECT   96   59                                                      
MASTER        0    0    0    0    0    0    0    0   96    0   96    0
END

https://cactus.nci.nih.gov/chemical/structure/C%5CC=C(/C)C(=O)SCCNC(=O)CCNC(=...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:95})
 96 98  0  0  0  0  0  0  0  0999 V2000
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   16.1669    3.8195   -0.7230 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3422    3.4082    0.2357 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6136    3.7754    1.6719 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1651    2.5948   -0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9460    2.2982   -1.2650 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0725    2.0498    1.1648 S   0  0  0  0  0  0  0  0  0  0  0  0
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   10.7903    0.5502    1.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8160   -0.1923    0.2841 N   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4063   -5.1509    0.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0537   -4.2525   -1.4230 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217   -3.3208   -0.0184 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7597   -3.3378    1.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6321   -1.8794   -0.4270 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.3978   -0.1366    0.4843 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.8704   -0.3039    1.4235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9903    1.1172   -0.0885 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9287    2.1145    0.3694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.7027    2.4130    1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2940    1.3839    0.3026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.6891    1.3898   -0.7133 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.4446   -0.7907    0.1381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2039   -0.2461    2.1289 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2035   -1.3880    2.6665 P   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1903   -1.3982    4.2764 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6957   -1.0844    2.1439 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7627   -2.7075    2.1612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9189    3.2788   -0.5200 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5267    3.2933   -1.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6475    4.4941   -2.3125 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1234    5.3239   -1.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3084    4.5530   -0.1933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7740    5.1397    0.9048 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0589    6.4247    0.9095 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9016    7.1897   -0.1556 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4454    6.6909   -1.2998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2835    7.5006   -2.4104 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0165    4.0936    0.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.9246    4.8927   -1.2822 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.0496    5.5751    0.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9724    3.5563   -1.7522 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.1208    4.7193    1.9049 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.2284    2.9933    2.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.6880    3.8794    1.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4069    1.8047   -0.5514 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3738    0.3232   -0.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2522   -0.1222    1.8109 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2852    1.3594    1.6148 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9239   -0.2492   -0.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3057   -0.8875   -0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2726   -2.3690   -0.4721 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1509   -2.8143    1.6941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1840   -1.3328    1.4979 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8227   -2.9415   -0.7952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2495   -3.4004   -1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4612   -2.8457    2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8058   -2.8107    1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6116   -4.3693    1.7244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0325   -1.8673   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7182   -1.2865   -0.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -1.4575    0.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6909   -3.9009   -1.9949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0694   -4.9399   -0.6901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5741   -2.3908   -3.6155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0874   -1.3443   -3.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5441   -1.0530   -1.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5147   -2.2057   -0.1039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4283    2.8940    1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7714   -2.0632    4.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0499   -0.2338    2.4376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1683    2.4351   -2.3744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4358    6.8702    1.8183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5038    8.4437   -2.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9496    7.1246   -3.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 60  1  0  0  0  0
  1 61  1  0  0  0  0
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 59 95  1  0  0  0  0
 59 96  1  0  0  0  0
M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-2-Methylcrotonoyl-CoA	ChEBI
2-Methylcrotanoyl-CoA	ChEBI
Methylcrotonoyl-CoA	ChEBI
Methylcrotonyl-CoA	ChEBI
Tigloyl-CoA	ChEBI
Tiglyl-CoA	ChEBI
trans-2-Methylbut-2-enoyl-CoA	ChEBI
Tiglyl-coenzyme A	MeSH
(E)-2-Methylbut-2-enoyl-CoA	HMDB
(E)-2-Methylbut-2-enoyl-coenzyme A	HMDB
(E)-2-Methylcrotonoyl-coenzyme A	HMDB
2-Methyl-crotonyl-CoA	HMDB
2-Methyl-crotonyl-coenzyme A	HMDB
2-Methylbut-2-enoyl-CoA	HMDB
2-Methylbut-2-enoyl-coenzyme A	HMDB
2-Methylcrotonyl-CoA	HMDB
Methylcrotonyl-coenzyme A	HMDB
Tigloyl-coenzyme A	HMDB
trans-2-Methylbut-2-enoyl-coenzyme A	HMDB

Chemical Formula

C₂₆H₄₂N₇O₁₇P₃S

Average Molecular Weight

849.64

Monoisotopic Molecular Weight

849.157075088

IUPAC Name

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

Traditional Name

methylcrotonyl-coenzyme A

CAS Registry Number

6247-62-7

SMILES

C\C=C(/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/C26H42N7O17P3S/c1-5-14(2)25(38)54-9-8-28-16(34)6-7-29-23(37)20(36)26(3,4)11-47-53(44,45)50-52(42,43)46-10-15-19(49-51(39,40)41)18(35)24(48-15)33-13-32-17-21(27)30-12-31-22(17)33/h5,12-13,15,18-20,24,35-36H,6-11H2,1-4H3,(H,28,34)(H,29,37)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/b14-5+/t15-,18-,19-,20+,24-/m1/s1

InChI Key

PMWATMXOQQZNBX-DKBZLLMOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Acyl CoAs

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

2-enoyl-CoA (CHEBI:15478 )

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

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	3.56 g/L	ALOGPS
logP	-0.02	ALOGPS
logP	-4.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	186.89 m³·mol⁻¹	ChemAxon
Polarizability	74.98 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

GC-MS

Spectrum Type	Description	Splash Key	Deposition Date	View
MS	Mass Spectrum (Electron Ionization)	splash10-0002-9021153000-bf7ae2f29efc61bc147e	2021-09-05	View Spectrum

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0100000190-7bc5f21431a94ab095d7	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00li-2910003320-c2787d0829f144df7f62	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-0029000000-762de97c012a43127364	2021-09-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000000090-7bd478ad08333c02352d	2021-09-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00lr-9400001210-b18f57b0ad53afeaacd6	2021-09-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004r-5103605910-9d3a6105011c02629c33	2021-09-09	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

FDB022819

KNApSAcK ID

Not Available

Chemspider ID

4947725

KEGG Compound ID

C03345

BioCyc ID

CPD-1083

BiGG ID

Not Available

Wikipedia Link

Tiglyl-CoA

METLIN ID

448

PubChem Compound

6443760

PDB ID

Not Available

ChEBI ID

15478

Food Biomarker Ontology

Not Available

VMH ID

2MB2COA

MarkerDB ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Duran M, Bruinvis L, Ketting D, Kamerling JP, Wadman SK, Schutgens RB: The identification of (E)-2-methylglutaconic acid, a new isoleucine metabolite, in the urine of patients with beta-ketothiolase deficiency, propionic acidaemia and methylmalonic acidaemia. Biomed Mass Spectrom. 1982 Jan;9(1):1-5. [PubMed:7059658 ]

Enzymes

Enzyme Details

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

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

Reactions

2-Methylbutyryl-CoA + Acceptor → Tiglyl-CoA + Reduced acceptor	details

Enzyme Details

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

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

Reactions

(S)-2-Methylbutanoyl-CoA + Acceptor → Tiglyl-CoA + Reduced acceptor	details

Enzyme Details

3. 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 → Tiglyl-CoA + Water	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. Short/branched chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Has greatest activity toward short branched chain acyl-CoA derivative such as (s)-2-methylbutyryl-CoA, isobutyryl-CoA, and 2-methylhexanoyl-CoA as well as toward short straight chain acyl-CoAs such as butyryl-CoA and hexanoyl-CoA. Can use valproyl-CoA as substrate and may play a role in controlling the metabolic flux of valproic acid in the development of toxicity of this agent.
Gene Name:: ACADSB
Uniprot ID:: P45954
Molecular weight:: 47485.035

Reactions

2-Methylbutyryl-CoA + Acceptor → Tiglyl-CoA + Reduced acceptor	details

Showing metabocard for Tiglyl-CoA (HMDB0002054)

MOL for HMDB0002054 (Tiglyl-CoA)

3D MOL for HMDB0002054 (Tiglyl-CoA)

3D SDF for HMDB0002054 (Tiglyl-CoA)

3D-SDF for HMDB0002054 (Tiglyl-CoA)

PDB for HMDB0002054 (Tiglyl-CoA)

3D PDB for HMDB0002054 (Tiglyl-CoA)

SMILES for HMDB0002054 (Tiglyl-CoA)

INCHI for HMDB0002054 (Tiglyl-CoA)

Structure for HMDB0002054 (Tiglyl-CoA)

3D Structure for HMDB0002054 (Tiglyl-CoA)

GC-MS

LC-MS/MS

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions