NP-MRD: Showing NP-Card for Phenylacetyl-CoA (NP0334761)

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Record Information

Version

2.0

Created at

2024-09-10 19:50:52 UTC

Updated at

2024-09-10 19:50:52 UTC

NP-MRD ID

NP0334761

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Phenylacetyl-CoA

Description

Phenylacetyl-CoA 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. An acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of phenylacetic acid. Phenylacetyl-CoA is a strong basic compound (based on its pKa). Phenylacetyl-CoA exists in all living organisms, ranging from bacteria to humans. Within humans, phenylacetyl-CoA participates in a number of enzymatic reactions. In particular, phenylacetyl-CoA can be biosynthesized from phenylacetic acid; which is mediated by the enzyme acyl-coenzyme A synthetase acsm1, mitochondrial. In addition, phenylacetyl-CoA can be biosynthesized from phenylacetic acid through its interaction with the enzyme acyl-coenzyme A synthetase acsm2b, mitochondrial. Phenylacetyl-CoA was first documented in 1978 (PMID: 666745). In humans, phenylacetyl-CoA is involved in phenylacetate metabolism (PMID: 6142928) (PMID: 11260461) (PMID: 2009287) (PMID: 2553650).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231220402D          

 57 60  0  0  1  0            999 V2000
   22.3229   -9.6336    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0458   -9.3024    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.6203  -10.3251    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.0415  -10.1783    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.5290  -11.7808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4928   -9.9145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4353  -11.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9518  -10.8088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5990   -8.6902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4337   -8.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2884   -9.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7947  -10.5150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6579   -9.8554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6640  -10.9935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0539  -11.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1364   -9.6569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3784   -9.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0071  -10.9725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5525   -9.4007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3953   -9.1068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1609  -10.7911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4878  -12.8186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4878  -14.1463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9926  -12.6575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2781  -13.8950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9926  -15.1325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3905  -10.5582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2332  -10.2643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7463  -10.6994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2602  -11.3660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5306  -10.9558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7440  -12.0344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1988  -10.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7071  -13.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9692  -13.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7071  -13.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2159  -10.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9690  -10.7051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4628  -10.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9926  -14.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5528   -9.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8790  -11.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2781  -13.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6373  -10.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0587  -10.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8118  -10.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4801   -9.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9014   -9.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6545  -10.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0760   -9.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7442   -9.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4973   -9.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1656   -9.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5821  -10.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9187   -9.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3353  -10.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0034  -10.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 49  1  0  0  0  0
  1 50  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2 13  2  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  3 14  1  0  0  0  0
  3 16  2  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  4 17  1  0  0  0  0
  4 18  2  0  0  0  0
  5 31  1  0  0  0  0
  5 32  1  0  0  0  0
 29  6  1  6  0  0  0
 30  7  1  6  0  0  0
  8 33  1  0  0  0  0
 12 39  1  0  0  0  0
 38 15  1  6  0  0  0
 19 44  2  0  0  0  0
 20 47  2  0  0  0  0
 21 50  2  0  0  0  0
 32 22  1  1  0  0  0
 22 34  1  0  0  0  0
 22 35  1  0  0  0  0
 23 35  2  0  0  0  0
 23 36  1  0  0  0  0
 24 34  2  0  0  0  0
 24 43  1  0  0  0  0
 25 40  1  0  0  0  0
 25 43  2  0  0  0  0
 26 40  1  0  0  0  0
 27 44  1  0  0  0  0
 27 45  1  0  0  0  0
 28 47  1  0  0  0  0
 28 48  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  1  0  0  0
 34 36  1  0  0  0  0
 36 40  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 41  1  0  0  0  0
 37 42  1  0  0  0  0
 38 44  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 48 49  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 52 54  1  0  0  0  0
 53 55  1  0  0  0  0
 54 56  2  0  0  0  0
 55 57  2  0  0  0  0
 56 57  1  0  0  0  0
M  END


  Mrv0541 02231220402D          

 57 60  0  0  1  0            999 V2000
   22.3229   -9.6336    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.0458   -9.3024    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.6203  -10.3251    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.0415  -10.1783    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    9.5290  -11.7808    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4928   -9.9145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4353  -11.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9518  -10.8088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5990   -8.6902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4337   -8.7492    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2884   -9.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7947  -10.5150    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6579   -9.8554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6640  -10.9935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0539  -11.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1364   -9.6569    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3784   -9.4251    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0071  -10.9725    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5525   -9.4007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3953   -9.1068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.1609  -10.7911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4878  -12.8186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4878  -14.1463    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9926  -12.6575    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2781  -13.8950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9926  -15.1325    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3905  -10.5582    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2332  -10.2643    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7463  -10.6994    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.2602  -11.3660    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.5306  -10.9558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7440  -12.0344    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.1988  -10.4720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7071  -13.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9692  -13.4825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7071  -13.8950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2159  -10.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9690  -10.7051    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.4628  -10.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9926  -14.3075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5528   -9.6151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8790  -11.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2781  -13.0700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6373  -10.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0587  -10.0743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8118  -10.4112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4801   -9.9274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9014   -9.7806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6545  -10.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0760   -9.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7442   -9.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4973   -9.8236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1656   -9.3399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5821  -10.6442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9187   -9.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3353  -10.9811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0034  -10.4974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 49  1  0  0  0  0
  1 50  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  0  0  0  0
  2 13  2  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  3 14  1  0  0  0  0
  3 16  2  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  4 17  1  0  0  0  0
  4 18  2  0  0  0  0
  5 31  1  0  0  0  0
  5 32  1  0  0  0  0
 29  6  1  6  0  0  0
 30  7  1  6  0  0  0
  8 33  1  0  0  0  0
 12 39  1  0  0  0  0
 38 15  1  6  0  0  0
 19 44  2  0  0  0  0
 20 47  2  0  0  0  0
 21 50  2  0  0  0  0
 32 22  1  1  0  0  0
 22 34  1  0  0  0  0
 22 35  1  0  0  0  0
 23 35  2  0  0  0  0
 23 36  1  0  0  0  0
 24 34  2  0  0  0  0
 24 43  1  0  0  0  0
 25 40  1  0  0  0  0
 25 43  2  0  0  0  0
 26 40  1  0  0  0  0
 27 44  1  0  0  0  0
 27 45  1  0  0  0  0
 28 47  1  0  0  0  0
 28 48  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 30 32  1  0  0  0  0
 31 33  1  1  0  0  0
 34 36  1  0  0  0  0
 36 40  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 41  1  0  0  0  0
 37 42  1  0  0  0  0
 38 44  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 48 49  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  2  0  0  0  0
 52 54  1  0  0  0  0
 53 55  1  0  0  0  0
 54 56  2  0  0  0  0
 55 57  2  0  0  0  0
 56 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334761

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H42N7O17P3S/c1-29(2,24(40)27(41)32-9-8-19(37)31-10-11-57-20(38)12-17-6-4-3-5-7-17)14-50-56(47,48)53-55(45,46)49-13-18-23(52-54(42,43)44)22(39)28(51-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-7,15-16,18,22-24,28,39-40H,8-14H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t18-,22-,23-,24+,28-/m1/s1

> <INCHI_KEY>
ZIGIFDRJFZYEEQ-CECATXLMSA-N

> <FORMULA>
C29H42N7O17P3S

> <MOLECULAR_WEIGHT>
885.667

> <EXACT_MASS>
885.157073179

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
79.56336726521648

> <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-[(2-phenylacetyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.03

> <JCHEM_LOGP>
-5.140871050299685

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8334045176178515

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8252479627216065

> <JCHEM_PKA_STRONGEST_BASIC>
4.946047024039826

> <JCHEM_POLAR_SURFACE_AREA>
363.6299999999999

> <JCHEM_REFRACTIVITY>
196.92990000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenylacetyl-coa

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  S   UNK     0      41.669 -17.983   0.000  0.00  0.00           S+0
HETATM    2  P   UNK     0      16.886 -17.364   0.000  0.00  0.00           P+0
HETATM    3  P   UNK     0      21.691 -19.274   0.000  0.00  0.00           P+0
HETATM    4  P   UNK     0      24.344 -19.000   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0      17.788 -21.991   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      15.853 -18.507   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      13.879 -21.214   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      20.443 -20.176   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      17.918 -16.222   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      15.743 -16.332   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      22.938 -18.371   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      25.750 -19.628   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      18.028 -18.397   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      21.773 -20.521   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      29.967 -21.515   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      20.788 -18.026   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      24.973 -17.593   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      24.280 -20.482   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      30.898 -17.548   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      36.205 -16.999   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      43.234 -20.143   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0      15.844 -23.928   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0      15.844 -26.406   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      13.053 -23.627   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      11.719 -25.937   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0      13.053 -28.247   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      32.462 -19.709   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      37.769 -19.160   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      16.326 -19.972   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      15.419 -21.217   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      17.790 -20.451   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.322 -22.464   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      19.038 -19.548   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.387 -24.397   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      16.742 -25.167   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.387 -25.937   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      28.403 -19.354   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      29.809 -19.983   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      26.997 -18.725   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      13.053 -26.707   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      29.032 -17.948   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      27.774 -20.760   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      11.719 -24.397   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      31.056 -19.080   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      33.710 -18.805   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      35.115 -19.434   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      36.363 -18.531   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      39.016 -18.257   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      40.422 -18.886   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      43.075 -18.612   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      44.323 -17.709   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      45.728 -18.337   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      46.976 -17.434   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      45.887 -19.869   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      48.382 -18.063   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      47.293 -20.498   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      48.540 -19.595   0.000  0.00  0.00           C+0
CONECT    1   49   50                                                       
CONECT    2    6    9   10   13                                             
CONECT    3    8   11   14   16                                             
CONECT    4   11   12   17   18                                             
CONECT    5   31   32                                                       
CONECT    6    2   29                                                       
CONECT    7   30                                                            
CONECT    8    3   33                                                       
CONECT    9    2                                                            
CONECT   10    2                                                            
CONECT   11    3    4                                                       
CONECT   12    4   39                                                       
CONECT   13    2                                                            
CONECT   14    3                                                            
CONECT   15   38                                                            
CONECT   16    3                                                            
CONECT   17    4                                                            
CONECT   18    4                                                            
CONECT   19   44                                                            
CONECT   20   47                                                            
CONECT   21   50                                                            
CONECT   22   32   34   35                                                  
CONECT   23   35   36                                                       
CONECT   24   34   43                                                       
CONECT   25   40   43                                                       
CONECT   26   40                                                            
CONECT   27   44   45                                                       
CONECT   28   47   48                                                       
CONECT   29    6   30   31                                                  
CONECT   30    7   29   32                                                  
CONECT   31    5   29   33                                                  
CONECT   32    5   22   30                                                  
CONECT   33    8   31                                                       
CONECT   34   22   24   36                                                  
CONECT   35   22   23                                                       
CONECT   36   23   34   40                                                  
CONECT   37   38   39   41   42                                             
CONECT   38   15   37   44                                                  
CONECT   39   12   37                                                       
CONECT   40   25   26   36                                                  
CONECT   41   37                                                            
CONECT   42   37                                                            
CONECT   43   24   25                                                       
CONECT   44   19   27   38                                                  
CONECT   45   27   46                                                       
CONECT   46   45   47                                                       
CONECT   47   20   28   46                                                  
CONECT   48   28   49                                                       
CONECT   49    1   48                                                       
CONECT   50    1   21   51                                                  
CONECT   51   50   52                                                       
CONECT   52   51   53   54                                                  
CONECT   53   52   55                                                       
CONECT   54   52   56                                                       
CONECT   55   53   57                                                       
CONECT   56   54   57                                                       
CONECT   57   55   56                                                       
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

View in JSmol

Synonyms

Value	Source
coenzyme A, S-(Benzeneacetate)	ChEBI
Phenylacetyl coenzyme A	ChEBI
Phenylacetyl-coenzyme A	ChEBI
coenzyme A, S-(Benzeneacetic acid)	Generator
coenzyme A, Phenylacetyl	HMDB

Chemical Formula

C₂₉H₄₂N₇O₁₇P₃S

Average Mass

885.6670 Da

Monoisotopic Mass

885.15707 Da

IUPAC Name

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

Traditional Name

phenylacetyl-coa

CAS Registry Number

Not Available

SMILES

CC(C)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C(N)N=CN=C12)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CC1=CC=CC=C1

InChI Identifier

InChI=1S/C29H42N7O17P3S/c1-29(2,24(40)27(41)32-9-8-19(37)31-10-11-57-20(38)12-17-6-4-3-5-7-17)14-50-56(47,48)53-55(45,46)49-13-18-23(52-54(42,43)44)22(39)28(51-18)36-16-35-21-25(30)33-15-34-26(21)36/h3-7,15-16,18,22-24,28,39-40H,8-14H2,1-2H3,(H,31,37)(H,32,41)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t18-,22-,23-,24+,28-/m1/s1

InChI Key

ZIGIFDRJFZYEEQ-CECATXLMSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Alkyl phosphate
Imidolactam
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Pyrimidine
Benzenoid
Fatty amide
Phosphoric acid ester
Monocyclic benzene moiety
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organic oxygen compound
Organosulfur compound
Carbonyl group
Organic nitrogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organopnictogen compound
Organic oxide
Organonitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acyl-CoA (CHEBI:15537 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	-0.03	ALOGPS
logP	-5.1	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	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	22	ChemAxon
Refractivity	196.93 m³·mol⁻¹	ChemAxon
Polarizability	79.56 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0006503

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

34-DIHYDROXYPHENYLACETYL-COA

BiGG ID

35419

Wikipedia Link

Phenylacetyl-CoA

METLIN ID

Not Available

PubChem Compound

165620

PDB ID

FAQ

ChEBI ID

15537

Good Scents ID

Not Available

References

General References

Potempska A, Loo YH, Wisniewski HM: On the possible mechanism of phenylacetate neurotoxicity: inhibition of choline acetyltransferase by phenylacetyl-CoA. J Neurochem. 1984 May;42(5):1499-501. doi: 10.1111/j.1471-4159.1984.tb02819.x. [PubMed:6142928 ]
Luengo JM, Garcia JL, Olivera ER: The phenylacetyl-CoA catabolon: a complex catabolic unit with broad biotechnological applications. Mol Microbiol. 2001 Mar;39(6):1434-42. doi: 10.1046/j.1365-2958.2001.02344.x. [PubMed:11260461 ]
Rodriguez-Aparicio LB, Reglero A, Martinez-Blanco H, Luengo JM: Fluorometric determination of phenylacetyl-CoA ligase from Pseudomonas putida: a very sensitive assay for a newly described enzyme. Biochim Biophys Acta. 1991 Mar 4;1073(2):431-3. doi: 10.1016/0304-4165(91)90153-8. [PubMed:2009287 ]
Martin-Villacorta J, Reglero A, Luengo JM: IV. Acyl-CoA: 6-APA acyltransferase of Penicillium chrysogenum: studies on substrate specificity using phenylacetyl-CoA variants. J Antibiot (Tokyo). 1989 Oct;42(10):1502-5. doi: 10.7164/antibiotics.42.1502. [PubMed:2553650 ]
James MO, Bend JR: A radiochemical assay for glycine N-acyltransferase activity. Some properties of the enzyme in rat and rabbit. Biochem J. 1978 May 15;172(2):285-91. doi: 10.1042/bj1720285. [PubMed:666745 ]

Showing NP-Card for Phenylacetyl-CoA (NP0334761)

MOL for NP0334761 (Phenylacetyl-CoA)

3D MOL for NP0334761 (Phenylacetyl-CoA)

3D SDF for NP0334761 (Phenylacetyl-CoA)

3D-SDF for NP0334761 (Phenylacetyl-CoA)

PDB for NP0334761 (Phenylacetyl-CoA)

3D PDB for NP0334761 (Phenylacetyl-CoA)

SMILES for NP0334761 (Phenylacetyl-CoA)

INCHI for NP0334761 (Phenylacetyl-CoA)

Structure for NP0334761 (Phenylacetyl-CoA)

3D Structure for NP0334761 (Phenylacetyl-CoA)