ChemFOnt: Showing chemical card for Pentanoyl-CoA (CFc000008174)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:50 UTC

Chemfont ID

CFc000008174

Molecule Identification

Common Name

Pentanoyl-CoA

Definition

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

Synonyms

Value	Source
Pentanoyl-coenzyme A	HMDB

Chemical Formula

C₂₆H₄₄N₇O₁₇P₃S

Average Molecular Weight

851.651

Monoisotopic Molecular Weight

851.172723243

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({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

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(pentanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

4752-33-4

SMILES

CCCCC(=O)SCCNC(=O)CCNC(=O)C(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-TVCSPYKZSA-N

Chemical Taxonomy

Description

Belongs to the class of inorganic compounds known as homogeneous transition metal compounds. These are inorganic compounds containing only metal atoms,with the largest atom being a transition metal atom.

Kingdom

Inorganic compounds

Super Class

Homogeneous metal compounds

Class

Homogeneous transition metal compounds

Sub Class

Not Available

Direct Parent

Homogeneous transition metal compounds

Alternative Parents

Not Available

Substituents

Homogeneous transition metal

Molecular Framework

Not Available

External Descriptors

iron cation (CHEBI:29034 )
monoatomic trication (CHEBI:29034 )
a cation (FE+3 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0013037)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013037)

Source

Endogenous

Endogenous (HMDB: HMDB0013037)

Animal

Animal (HMDB: HMDB0013037)

Exogenous

Food

Food (HMDB: HMDB0013037)

Exogenous (HMDB: HMDB0013037)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013037)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013037)
Valproic Acid Metabolism Pathway (PathBank: SMP0000635)

Lipid metabolism pathway (HMDB: HMDB0013037)

Cellular process

Cell signaling (HMDB: HMDB0013037)

Biochemical process

Lipid transport (HMDB: HMDB0013037)

Role

Biological role

Energy source (HMDB: HMDB0013037)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013037)

Physical Properties

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)	4.01	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	23	ChemAxon
Refractivity	186.04 m³·mol⁻¹	ChemAxon
Polarizability	76.5 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