ChemFOnt: Showing chemical card for Heptanoyl-CoA (CFc000008136)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:47 UTC

Chemfont ID

CFc000008136

Molecule Identification

Common Name

Heptanoyl-CoA

Definition

Heptanoyl-CoA is an acyl-CoA with the C-7 fatty acid Acyl chain moiety. 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
2-Methyloctanoyl CoA, 21	HMDB
2-Methyloctanoyl coenzyme A, 21	HMDB
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-(2-{[2-(heptanoylsulfanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidate	Generator
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-(2-{[2-(heptanoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidate	Generator
4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-N-(2-{[2-(heptanoylsulphanyl)ethyl]-C-hydroxycarbonimidoyl}ethyl)-2-hydroxy-3,3-dimethylbutanimidic acid	Generator

Chemical Formula

C₂₈H₄₈N₇O₁₇P₃S

Average Molecular Weight

879.704

Monoisotopic Molecular Weight

879.204023371

IUPAC Name

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

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-{[({3-[(2-{[2-(heptanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxyphosphonic acid

CAS Registry Number

None

SMILES

CCCCCCC(=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/C28H48N7O17P3S/c1-4-5-6-7-8-19(37)56-12-11-30-18(36)9-10-31-26(40)23(39)28(2,3)14-49-55(46,47)52-54(44,45)48-13-17-22(51-53(41,42)43)21(38)27(50-17)35-16-34-20-24(29)32-15-33-25(20)35/h15-17,21-23,27,38-39H,4-14H2,1-3H3,(H,30,36)(H,31,40)(H,44,45)(H,46,47)(H2,29,32,33)(H2,41,42,43)/t17-,21-,22-,23?,27-/m1/s1

InChI Key

CHVYGJMBUXUTSX-AXEMQUGESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiocyanates. These are salts or esters of thiocyanic acid, with the general formula RSC#N (R=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organosulfur compounds

Class

Thiocyanates

Sub Class

Not Available

Direct Parent

Thiocyanates

Alternative Parents

Substituents

Sulfenyl compound
So-thioperoxol
Thiocyanate
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0012969)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0012969)

Source

Endogenous

Endogenous (HMDB: HMDB0012969)

Animal

Animal (HMDB: HMDB0012969)

Exogenous

Food

Food (HMDB: HMDB0012969)

Exogenous (HMDB: HMDB0012969)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0012969)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0012969)

Lipid metabolism pathway (HMDB: HMDB0012969)

Cellular process

Cell signaling (HMDB: HMDB0012969)

Biochemical process

Lipid transport (HMDB: HMDB0012969)

Role

Biological role

Energy source (HMDB: HMDB0012969)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0012969)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.61 g/L	ALOGPS
logP	0.25	ALOGPS
logP	-3.4	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	25	ChemAxon
Refractivity	195.24 m³·mol⁻¹	ChemAxon
Polarizability	81.33 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

External Links

HMDB ID

HMDB0012969

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029227

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-10054

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481563

PDB ID

Not Available

ChEBI ID

37283

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Heptanoyl-CoA (CFc000008136)

MOL for CFc000008136 (Heptanoyl-CoA)

3D MOL for CFc000008136 (Heptanoyl-CoA)

3D SDF for CFc000008136 (Heptanoyl-CoA)

3D-SDF for CFc000008136 (Heptanoyl-CoA)

PDB for CFc000008136 (Heptanoyl-CoA)

3D PDB for CFc000008136 (Heptanoyl-CoA)

SMILES for CFc000008136 (Heptanoyl-CoA)

INCHI for CFc000008136 (Heptanoyl-CoA)

Structure for CFc000008136 (Heptanoyl-CoA)

3D Structure for CFc000008136 (Heptanoyl-CoA)