ChemFOnt: Showing chemical card for Retinoyl CoA (CFc000002778)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:44 UTC

Chemfont ID

CFc000002778

Molecule Identification

Common Name

Retinoyl CoA

Definition

Retinoyl coenzyme A is an intermediate in vitamin A metabolism. The formation of retinoyl-CoA from retinoic acid, as the first step of retinoylation (acylation of proteins by retinoic acid in cells), required ATP, CoA and MgCl2.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
CoA-Retinol acyltransferase, acyl	MeSH
Ester synthetase, retinol	MeSH
Fatty acyl coenzyme A retinol acyltransferase	MeSH
Synthetase, retinol stearate	MeSH
Synthetase, retinol-palmitate	MeSH
Fatty acyl coenzyme A-retinol acyltransferase	MeSH
Retinol fatty-acyltransferase	MeSH
Acyl CoA retinol acyltransferase	MeSH
Fatty-acyltransferase, retinol	MeSH
O-Fatty-acyltransferase, retinol	MeSH
Retinol ester synthetase	MeSH
Retinol fatty acyltransferase	MeSH
Retinol O-fatty-acyltransferase	MeSH
Stearate synthetase, retinol	MeSH
Synthetase, retinol ester	MeSH
Acyl CoA-retinol acyltransferase	MeSH
Acyltransferase, acyl CoA-retinol	MeSH
Retinol O fatty acyltransferase	MeSH
Retinol palmitate synthetase	MeSH
Retinol stearate synthetase	MeSH
Retinol-palmitate synthetase	MeSH
Acyl-CoA-retinol acyltransferase	HMDB
Acyl-CoA-retinol acyltransferase.	HMDB
Acyl-coenzyme A-retinol acyltransferase	HMDB
Acyl-coenzyme A-retinol acyltransferase.	HMDB
Retinol acyltransferase	HMDB
Retinol O-acyltransferase	HMDB
Retinoyl coenzyme A	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-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanimidate	Generator, 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-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]sulphanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanimidate	Generator, 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-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]sulphanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanimidic acid	Generator, HMDB

Chemical Formula

C₄₁H₆₂N₇O₁₇P₃S

Average Molecular Weight

1049.954

Monoisotopic Molecular Weight

1049.313573819

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-({[({[3-({2-[(2-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]sulfanyl}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-{[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoyl]sulfanyl}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

81295-48-9

SMILES

OC(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)C(=O)NCCC(=O)NCCSC(=O)\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C41H62N7O17P3S/c1-25(13-14-28-27(3)12-9-16-40(28,4)5)10-8-11-26(2)20-31(50)69-19-18-43-30(49)15-17-44-38(53)35(52)41(6,7)22-62-68(59,60)65-67(57,58)61-21-29-34(64-66(54,55)56)33(51)39(63-29)48-24-47-32-36(42)45-23-46-37(32)48/h8,10-11,13-14,20,23-24,29,33-35,39,51-52H,9,12,15-19,21-22H2,1-7H3,(H,43,49)(H,44,53)(H,57,58)(H,59,60)(H2,42,45,46)(H2,54,55,56)/b11-8+,14-13+,25-10+,26-20+/t29-,33-,34-,35?,39-/m1/s1

InChI Key

GREHPZMOJNYZIO-QXBAZQDESA-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 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Diterpenoid
Retinoid skeleton
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
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Fatty amide
Phosphoric acid ester
Alkyl phosphate
Imidolactam
Pyrimidine
Azole
Imidazole
Tetrahydrofuran
Heteroaromatic compound
Amino acid or derivatives
Secondary carboxylic acid amide
Thiocarboxylic acid ester
Carboxamide group
Secondary alcohol
Carbothioic s-ester
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Sulfenyl compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Carbonyl group
Organic nitrogen compound
Primary amine
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
Amine
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006508)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006508)

Source

Endogenous

Endogenous (HMDB: HMDB0006508)

Animal

Animal (HMDB: HMDB0006508)

Exogenous

Food

Food (HMDB: HMDB0006508)

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)

Exogenous (HMDB: HMDB0006508)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006508)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006508)

Lipid metabolism pathway (HMDB: HMDB0006508)

Cellular process

Cell signaling (HMDB: HMDB0006508)

Biochemical process

Lipid transport (HMDB: HMDB0006508)

Role

Biological role

Energy source (HMDB: HMDB0006508)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0006508)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.33 g/L	ALOGPS
logP	2.21	ALOGPS
logP	-1.5	ChemAxon
logS	-3.5	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	25	ChemAxon
Refractivity	257.36 m³·mol⁻¹	ChemAxon
Polarizability	101.44 Å³	ChemAxon
Number of Rings	4	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

HMDB0006508

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023947

KNApSAcK ID

Not Available

Chemspider ID

35015996

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

2430158

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14232703

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Retinoyl CoA (CFc000002778)

MOL for CFc000002778 (Retinoyl CoA)

3D MOL for CFc000002778 (Retinoyl CoA)

3D SDF for CFc000002778 (Retinoyl CoA)

3D-SDF for CFc000002778 (Retinoyl CoA)

PDB for CFc000002778 (Retinoyl CoA)

3D PDB for CFc000002778 (Retinoyl CoA)

SMILES for CFc000002778 (Retinoyl CoA)

INCHI for CFc000002778 (Retinoyl CoA)

Structure for CFc000002778 (Retinoyl CoA)

3D Structure for CFc000002778 (Retinoyl CoA)