ChemFOnt: Showing chemical card for Hexanoyl-CoA (CFc000001717)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:25 UTC

Chemfont ID

CFc000001717

Molecule Identification

Common Name

Hexanoyl-CoA

Definition

Hexanoyl-CoA, also known as hexanoyl-coenzyme A or caproyl-CoA, is a medium-chain fatty acyl-CoA having hexanoyl as the acyl group. Hexanoyl-CoA is slightly soluble (in water) and an extremely strong acidic compound (based on its pKa). Within the cell, hexanoyl-CoA is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. Hexanoyl-CoA exists in all living organisms, ranging from bacteria to humans. In humans, hexanoyl-CoA is involved in the biosynthesis and oxidation of fatty acids as well as in ceramide formation. Hexanoyl-CoA is also involved in few metabolic disorders, such as fatty acid elongation in mitochondria, mitochondrial beta-oxidation of medium chain saturated fatty acids, and mitochondrial beta-oxidation of short chain saturated fatty acids.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
6-Carboxyhexanoyl-CoA	HMDB
6-Carboxyhexanoyl-coenzyme A	HMDB
Caproyl-CoA	HMDB
Caproyl-coenzyme A	HMDB
Hexanoyl-coenzyme A	HMDB
Pimeloyl-CoA	HMDB
Pimeloyl-coenzyme A	HMDB

Chemical Formula

C₂₇H₄₆N₇O₁₇P₃S

Average Molecular Weight

865.677

Monoisotopic Molecular Weight

865.188373307

IUPAC Name

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

5060-32-2

SMILES

[H]C(O)(C(O)=NCCC(O)=NCCSC(=O)CCCCC)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)(O)=O

InChI Identifier

InChI=1S/C27H46N7O17P3S/c1-4-5-6-7-18(36)55-11-10-29-17(35)8-9-30-25(39)22(38)27(2,3)13-48-54(45,46)51-53(43,44)47-12-16-21(50-52(40,41)42)20(37)26(49-16)34-15-33-19-23(28)31-14-32-24(19)34/h14-16,20-22,26,37-38H,4-13H2,1-3H3,(H,29,35)(H,30,39)(H,43,44)(H,45,46)(H2,28,31,32)(H2,40,41,42)/t16-,20-,21-,22?,26-/m1/s1

InChI Key

OEXFMSFODMQEPE-ZOGSZLKASA-N

Chemical Taxonomy

Description

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

Fatty acyl CoAs (C05270 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0002845)
Membrane (HMDB: HMDB0002845)

Source

Exogenous

Exogenous (HMDB: HMDB0002845)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0002845)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty Acids (HMDB: HMDB0002845)
Fatty Acid Metabolism (HMDB: HMDB0002845)
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids (HMDB: HMDB0002845)
Fatty Acid Elongation In Mitochondria (HMDB: HMDB0002845)
Fatty Acid Oxidation (Hexanoate) (PathBank: SMP0121348)
Fatty Acid Metabolism (PathBank: SMP0002361)
Fatty Acid Elongation In Mitochondria (PathBank: SMP0002368)
Fatty Acid Elongation (PathBank: SMP0121069)
Fatty Acid Oxidation (Octanoate) (PathBank: SMP0121351)
Fatty Acid Elongation In Mitochondria (PathBank: SMP0063612)

Disease pathway

Short-chain 3-hydroxyacyl-CoA dehydrogenase deficiency (SCHAD) (PathBank: SMP0120632)

Role

Biological role

Human metabolite (HMDB: HMDB0002845)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	5.7 g/L	ALOGPS
logP	0.31	ALOGPS
logP	-3.8	ChemAxon
logS	-2.2	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	24	ChemAxon
Refractivity	190.64 m³·mol⁻¹	ChemAxon
Polarizability	79.61 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023074

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C05270

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440611

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Pullman, Maynard E. Convenient and versatile method for the purification of CoA thiol esters. Analytical Biochemistry (1973), 54(1), 188-98.

Showing chemical card for Hexanoyl-CoA (CFc000001717)

MOL for CFc000001717 (Hexanoyl-CoA)

3D MOL for CFc000001717 (Hexanoyl-CoA)

3D SDF for CFc000001717 (Hexanoyl-CoA)

3D-SDF for CFc000001717 (Hexanoyl-CoA)

PDB for CFc000001717 (Hexanoyl-CoA)

3D PDB for CFc000001717 (Hexanoyl-CoA)

SMILES for CFc000001717 (Hexanoyl-CoA)

INCHI for CFc000001717 (Hexanoyl-CoA)

Structure for CFc000001717 (Hexanoyl-CoA)

3D Structure for CFc000001717 (Hexanoyl-CoA)