MiMeDB: Showing metabocard for Pentanoyl-CoA (MMDBc0048641)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-04-29 22:05:51 UTC

Update Date

2024-04-30 20:36:58 UTC

Metabolite ID

MMDBc0048641

Metabolite Identification

Common Name

Pentanoyl-CoA

Description

Pentanoyl CoA is an acyl-CoA with the C-5 Acyl chain. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid, inside living cells. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. This is then used in the citric acid cycle to start a chain of reactions, eventually forming many adenosine triphosphates. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. First, the fatty acid displaces the diphosphate group of ATP, then coenzyme A (HSCoA) displaces the AMP group to form an Acyl-CoA. The acyladenylate product of the first step has a large free energy of hydrolysis and conserves the free energy of the cleaved phosphoanhydride bond in ATP. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Consequently, the overall reaction Fatty acid + CoA + ATP <=> Acyl-CoA + AMP + PPi has a free energy change near zero. Subsequent hydrolysis of the product PPi (by the enzyme inorganic pyrophosphatase) is highly exergonic, and this reaction makes the formation of acyl-CoA spontaneous and irreversible. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. Because there is no transport protein for CoA adducts, acyl groups must enter the mitochondria via a shuttle system involving the small molecule carnitine.

Structure

MOL SDF PDB SMILES InChI

 
  Mrv1533006081517232D          
 
 54 56  0  0  1  0            999 V2000
   17.7920  -16.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5065  -16.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2209  -16.9538    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.9354  -16.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6499  -16.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3643  -16.5413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0788  -16.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7933  -16.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5077  -16.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2222  -16.5413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9367  -16.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6511  -16.5413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.3656  -16.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0801  -16.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7945  -16.9538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5065  -15.7164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0788  -17.7787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9367  -17.7785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6511  -15.7163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3656  -16.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3656  -17.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6195  -16.9538    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.4445  -16.9538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6195  -17.7788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7913  -14.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.6163  -14.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.8712  -13.2404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.2038  -12.7554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5363  -13.2404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.6488  -12.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3063  -14.6924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1012  -14.6924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9262  -14.6924    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.9262  -13.8674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7512  -14.6924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9262  -15.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1100  -12.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1100  -12.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5390  -12.9938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5390  -12.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8245  -11.7563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3956  -11.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6810  -12.1688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6810  -12.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3956  -13.4063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3956  -10.9314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8169  -13.2424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6419  -13.2424    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.6419  -12.4174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4669  -13.2424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6419  -15.1399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0677  -16.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3581  -16.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6610  -16.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 16  2  0  0  0  0
  7 17  2  0  0  0  0
 11 18  2  0  0  0  0
 12 19  1  6  0  0  0
 13 20  1  0  0  0  0
 13 21  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 27 30  1  6  0  0  0
 25 31  1  1  0  0  0
 26 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  2  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 37 41  1  0  0  0  0
 37 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 38 45  1  0  0  0  0
 42 46  1  0  0  0  0
 29 39  1  6  0  0  0
 30 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
 48 51  1  0  0  0  0
 22 51  1  0  0  0  0
  1 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END

 
  Mrv1533006081517232D          
 
 54 56  0  0  1  0            999 V2000
   17.7920  -16.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5065  -16.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2209  -16.9538    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.9354  -16.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6499  -16.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3643  -16.5413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.0788  -16.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7933  -16.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5077  -16.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2222  -16.5413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9367  -16.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6511  -16.5413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.3656  -16.9538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0801  -16.5413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7945  -16.9538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5065  -15.7164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0788  -17.7787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9367  -17.7785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6511  -15.7163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3656  -16.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3656  -17.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6195  -16.9538    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   29.4445  -16.9538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6195  -17.7788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7913  -14.0250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.6163  -14.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   25.8712  -13.2404    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   25.2038  -12.7554    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5363  -13.2404    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.6488  -12.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3063  -14.6924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.1012  -14.6924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9262  -14.6924    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   26.9262  -13.8674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.7512  -14.6924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9262  -15.5174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.1100  -12.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1100  -12.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5390  -12.9938    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5390  -12.1688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8245  -11.7563    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3956  -11.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6810  -12.1688    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6810  -12.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3956  -13.4063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.3956  -10.9314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8169  -13.2424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6419  -13.2424    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   28.6419  -12.4174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4669  -13.2424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6419  -15.1399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0677  -16.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3581  -16.9451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6610  -16.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 16  2  0  0  0  0
  7 17  2  0  0  0  0
 11 18  2  0  0  0  0
 12 19  1  6  0  0  0
 13 20  1  0  0  0  0
 13 21  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 27 30  1  6  0  0  0
 25 31  1  1  0  0  0
 26 32  1  1  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  2  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
 40 41  2  0  0  0  0
 37 41  1  0  0  0  0
 37 42  1  0  0  0  0
 42 43  2  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 38 45  1  0  0  0  0
 42 46  1  0  0  0  0
 29 39  1  6  0  0  0
 30 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 48 50  2  0  0  0  0
 48 51  1  0  0  0  0
 22 51  1  0  0  0  0
  1 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0048641

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCC(=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/C26H44N7O17P3S/c1-4-5-6-17(35)54-10-9-28-16(34)7-8-29-24(38)21(37)26(2,3)12-47-53(44,45)50-52(42,43)46-11-15-20(49-51(39,40)41)19(36)25(48-15)33-14-32-18-22(27)30-13-31-23(18)33/h13-15,19-21,25,36-37H,4-12H2,1-3H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21+,25-/m1/s1

> <INCHI_KEY>
RXUATCUKICAIOA-ZMHDXICWSA-N

> <FORMULA>
C26H44N7O17P3S

> <MOLECULAR_WEIGHT>
851.65

> <EXACT_MASS>
851.172725153

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
76.01483305804963

> <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-(pentanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.09

> <JCHEM_LOGP>
-4.335071244832592

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.9035538370263239

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8207476508908789

> <JCHEM_PKA_STRONGEST_BASIC>
4.945907435196925

> <JCHEM_POLAR_SURFACE_AREA>
363.62999999999994

> <JCHEM_REFRACTIVITY>
186.0369

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
valeryl-coa

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-JUN-15   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-JUN-15         0                                  
HETATM    1  C   UNK     0      33.212 -31.647   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      34.545 -30.877   0.000  0.00  0.00           C+0
HETATM    3  S   UNK     0      35.879 -31.647   0.000  0.00  0.00           S+0
HETATM    4  C   UNK     0      37.213 -30.877   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      38.546 -31.647   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      39.880 -30.877   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0      41.214 -31.647   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      42.547 -30.877   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      43.881 -31.647   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      45.215 -30.877   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      46.548 -31.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      47.882 -30.877   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      49.216 -31.647   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      50.550 -30.877   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      51.883 -31.647   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      34.545 -29.337   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      41.214 -33.187   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      46.548 -33.187   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      47.882 -29.337   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      49.216 -30.107   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      49.216 -33.187   0.000  0.00  0.00           C+0
HETATM   22  P   UNK     0      53.423 -31.647   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0      54.963 -31.647   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      53.423 -33.187   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      46.277 -26.180   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      47.817 -26.180   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      48.293 -24.715   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      47.047 -23.810   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      45.801 -24.715   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      49.744 -24.244   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      45.372 -27.426   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      48.722 -27.426   0.000  0.00  0.00           O+0
HETATM   33  P   UNK     0      50.262 -27.426   0.000  0.00  0.00           P+0
HETATM   34  O   UNK     0      50.262 -25.886   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      51.802 -27.426   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      50.262 -28.966   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      41.272 -22.715   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      41.272 -24.255   0.000  0.00  0.00           C+0
HETATM   39  N   UNK     0      43.939 -24.255   0.000  0.00  0.00           N+0
HETATM   40  C   UNK     0      43.939 -22.715   0.000  0.00  0.00           C+0
HETATM   41  N   UNK     0      42.606 -21.945   0.000  0.00  0.00           N+0
HETATM   42  C   UNK     0      39.938 -21.945   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0      38.605 -22.715   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      38.605 -24.255   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0      39.938 -25.025   0.000  0.00  0.00           N+0
HETATM   46  N   UNK     0      39.938 -20.405   0.000  0.00  0.00           N+0
HETATM   47  O   UNK     0      51.925 -24.719   0.000  0.00  0.00           O+0
HETATM   48  P   UNK     0      53.465 -24.719   0.000  0.00  0.00           P+0
HETATM   49  O   UNK     0      53.465 -23.179   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      55.005 -24.719   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      53.465 -28.261   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      31.860 -30.866   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      30.535 -31.631   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      29.234 -30.879   0.000  0.00  0.00           C+0
CONECT    1    2   52                                                       
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14   20   21                                             
CONECT   14   13   15                                                       
CONECT   15   14   22                                                       
CONECT   16    2                                                            
CONECT   17    7                                                            
CONECT   18   11                                                            
CONECT   19   12                                                            
CONECT   20   13                                                            
CONECT   21   13                                                            
CONECT   22   15   23   24   51                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   26   29   31                                                  
CONECT   26   25   27   32                                                  
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   25   39                                                  
CONECT   30   27   47                                                       
CONECT   31   25                                                            
CONECT   32   26   33                                                       
CONECT   33   32   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   38   41   42                                                  
CONECT   38   37   39   45                                                  
CONECT   39   38   40   29                                                  
CONECT   40   39   41                                                       
CONECT   41   40   37                                                       
CONECT   42   37   43   46                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   38                                                       
CONECT   46   42                                                            
CONECT   47   30   48                                                       
CONECT   48   47   49   50   51                                             
CONECT   49   48                                                            
CONECT   50   48                                                            
CONECT   51   48   22                                                       
CONECT   52    1   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53                                                            
MASTER        0    0    0    0    0    0    0    0   54    0  112    0
END

Synonyms

Value	Source
5:0-CoA	ChEBI
C5:0-CoA	ChEBI
coenzyme A S-Pentanoate	ChEBI
Pentanoyl-coenzyme A	ChEBI
S-Valeryl-CoA	ChEBI
S-Valeryl-coenzym-a	ChEBI
S-Valeryl-coenzyme A	ChEBI
Valeryl-CoA	ChEBI
Valeryl-coenzyme A	ChEBI
coenzyme A S-Pentanoic acid	Generator

Molecular Formula

C₂₆H₄₄N₇O₁₇P₃S

Average Mass

851.65

Monoisotopic Mass

851.172725153

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-(pentanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

valeryl-coa

CAS Registry Number

Not Available

SMILES

CCCCC(=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/C26H44N7O17P3S/c1-4-5-6-17(35)54-10-9-28-16(34)7-8-29-24(38)21(37)26(2,3)12-47-53(44,45)50-52(42,43)46-11-15-20(49-51(39,40)41)19(36)25(48-15)33-14-32-18-22(27)30-13-31-23(18)33/h13-15,19-21,25,36-37H,4-12H2,1-3H3,(H,28,34)(H,29,38)(H,42,43)(H,44,45)(H2,27,30,31)(H2,39,40,41)/t15-,19-,20-,21+,25-/m1/s1

InChI Key

RXUATCUKICAIOA-ZMHDXICWSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

2,3,4-saturated fatty acyl CoAs

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

short-chain fatty acyl-CoA (CHEBI:15536 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.67 g/L	ALOGPS
logP	-0.09	ALOGPS
logP	-4.3	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.82	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	23	ChemAxon
Refractivity	186.04 m³·mol⁻¹	ChemAxon
Polarizability	76.01 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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0009155	Adenosine triphosphate	Adenosine monophosphate	Acyl-coa synthetase medium-chain family member 1	Butyrate Coenzyme A Ligase	VMH	30371894
MMDBr0009156	Pentanoyl-CoA	Pentanoyl-CoA	Not Available	HMR_0166	VMH	30371894
MMDBr0010089	Coenzyme A	Acetyl-CoA	Acetyl-coa acyltransferase 2	Acetyl Coenzyme A C-Acyltransferase	VMH	30371894
MMDBr0010090	FAD	FADH2	Acyl-coa dehydrogenase, short/branched chain	2-Methyl-Branched-Chain-Enoyl Coenzyme A Reductase	VMH	30371894
MMDBr0012695	3-Hydroxyisovaleryl-CoA	Acetic acid	Not Available	3-Hydroxyisovaleryl-CoA cleavage (hypothetical reaction)	VMH	30371894
MMDBr0012698	Acetic acid	Acetyl-CoA	Not Available	Valeryl-CoA:acetate CoA transferase	VMH	30371894
MMDBr0016775	Water	CoA	Acyl-CoA thioesterase 2	Hydrolysis	RHEA	34755880
MMDBr0016776	Water	CoA	Acyl-CoA thioesterase 2	Hydrolysis	RHEA	34755880
MMDBr0025038	Hydrogen Ion	Carbon dioxide	3-oxoacyl-[acyl-carrier-protein] synthase 3 protein 2	Synthesis	RHEA	34755880
MMDBr0025039	Hydrogen Ion	Carbon dioxide	3-oxoacyl-[acyl-carrier-protein] synthase 3 protein 2	Synthesis	RHEA	34755880
MMDBr0038831	Pentanoyl-CoA	pentanoic acid	Thioesterase TesA	Hydrolysis	RHEA	34755880
MMDBr0039006	Pentanoyl-CoA	pentanoic acid	Thioesterase 1/protease 1/lysophospholipase L1	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	2	Human feces	Metabolic reconstruction
Bacteria	Proteobacteria	2

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10140116

KEGG Compound ID

C00888

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11966122

PDB ID

Not Available

ChEBI ID

15536

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Pentanoyl-CoA (MMDBc0048641)

MOL for #<Metabolite:0x00007fe278388328>

3D MOL for #<Metabolite:0x00007fe278388328>

3D SDF for #<Metabolite:0x00007fe278388328>

3D-SDF for #<Metabolite:0x00007fe278388328>

PDB for #<Metabolite:0x00007fe278388328>

3D PDB for #<Metabolite:0x00007fe278388328>

SMILES for #<Metabolite:0x00007fe278388328>

INCHI for #<Metabolite:0x00007fe278388328>

Structure for #<Metabolite:0x00007fe278388328>

3D Structure for #<Metabolite:0x00007fe278388328>