ChemFOnt: Showing chemical card for 2,4,7,10,13,16,19-Docosaheptaenoyl-CoA (CFc000007236)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:53:28 UTC

Chemfont ID

CFc000007236

Molecule Identification

Common Name

2,4,7,10,13,16,19-Docosaheptaenoyl-CoA

Definition

2,4,7,10,13,16,19-Docosaheptaenoyl-CoA is a coenzyme A derivative, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. 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. This compound is formed by 2,4,7,10,13,16,19-Docosaheptaenoic acid reacting with thiol group of CoA molecules.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₄₃H₆₄N₇O₁₇P₃S

Average Molecular Weight

1075.991

Monoisotopic Molecular Weight

1075.329223883

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-[({[({3-[(2-{[2-(docosa-2,4,7,10,13,16,19-heptaenoylsulfanyl)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-(docosa-2,4,7,10,13,16,19-heptaenoylsulfanyl)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

302-72-7

SMILES

[H][C@]1(COP(O)(=O)OP(O)(=O)OCC(C)(C)C(O)C(=O)NCCC(=O)NCCSC(=O)C=CC=CCC=CCC=CCC=CCC=CCC=CCC)O[C@@]([H])(N2C=NC3=C2N=CN=C3N)[C@]([H])(O)[C@]1([H])OP(O)(O)=O

InChI Identifier

InChI=1S/C43H64N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-34(52)71-27-26-45-33(51)24-25-46-41(55)38(54)43(2,3)29-64-70(61,62)67-69(59,60)63-28-32-37(66-68(56,57)58)36(53)42(65-32)50-31-49-35-39(44)47-30-48-40(35)50/h5-6,8-9,11-12,14-15,17-18,20-23,30-32,36-38,42,53-54H,4,7,10,13,16,19,24-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)/t32-,36-,37-,38?,42-/m1/s1

InChI Key

HTSMCTDWAPSBNO-ZUIQPFKESA-N

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0011656)
Membrane (HMDB: HMDB0011656)

Source

Exogenous

Exogenous (HMDB: HMDB0011656)

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: HMDB0011656)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.21 g/L	ALOGPS
logP	3.85	ALOGPS
logP	0.23	ChemAxon
logS	-3.7	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	33	ChemAxon
Refractivity	272.05 m³·mol⁻¹	ChemAxon
Polarizability	105.01 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028347

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2,4,7,10,13,16,19-Docosaheptaenoyl-CoA (CFc000007236)

MOL for CFc000007236 (2,4,7,10,13,16,19-Docosaheptaenoyl-CoA)

3D MOL for CFc000007236 (2,4,7,10,13,16,19-Docosaheptaenoyl-CoA)

3D SDF for CFc000007236 (2,4,7,10,13,16,19-Docosaheptaenoyl-CoA)

3D-SDF for CFc000007236 (2,4,7,10,13,16,19-Docosaheptaenoyl-CoA)

PDB for CFc000007236 (2,4,7,10,13,16,19-Docosaheptaenoyl-CoA)

3D PDB for CFc000007236 (2,4,7,10,13,16,19-Docosaheptaenoyl-CoA)

SMILES for CFc000007236 (2,4,7,10,13,16,19-Docosaheptaenoyl-CoA)

INCHI for CFc000007236 (2,4,7,10,13,16,19-Docosaheptaenoyl-CoA)

Structure for CFc000007236 (2,4,7,10,13,16,19-Docosaheptaenoyl-CoA)

3D Structure for CFc000007236 (2,4,7,10,13,16,19-Docosaheptaenoyl-CoA)