ChemFOnt: Showing chemical card for Salicyloyl-CoA (CFc000007221)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:53:26 UTC

Chemfont ID

CFc000007221

Molecule Identification

Common Name

Salicyloyl-CoA

Definition

Salicyloyl-CoA is the intermediate product in the formation of salicyluric acid from salicylic acid. It has been shown to suppress LPS-induced PGE(2) production which effectively complements the action of salicylic acid -- the major metabolite of aspirin (PMID: 10903918 ). Salicyloyl-CoA is metabolized in the liver by mitochondrial acyl CoA:glycine N-acyl transferase (ACGNAT). This enzyme is important in the detoxification of various endogenous and xenobiotic acyl-CoA's.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2-Hydroxybenzoyl)-CoA	HMDB
(2-Hydroxybenzoyl)-coenzyme A	HMDB
(O-Hydroxybenzoyl)-coenzyme A	HMDB
S-(2-Hydroxybenzoate	HMDB
S-(2-Hydroxybenzoate)CoA	HMDB
S-(2-Hydroxybenzoate)coenzyme A	HMDB
S-(2-Hydroxybenzoic acid	HMDB
S-Salicylate (8ci)CoA	HMDB
S-Salicylate (8ci)coenzyme A	HMDB
Salicyl-CoA	HMDB
Salicyl-coenzyme A	HMDB
Salicyloyl-CoA	HMDB
Salicyloyl-coenzyme A	HMDB
Thio-salicylic acid S-ester with coenzyme A	HMDB

Chemical Formula

C₂₉H₄₂N₇O₁₇P₃S

Average Molecular Weight

885.667

Monoisotopic Molecular Weight

885.157073179

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-(2-methylbenzoylsulfanyl)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-(2-methylbenzoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

10478-66-7

SMILES

CC1=C(C=CC=C1)C(=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/C29H42N7O17P3S/c1-16-6-4-5-7-17(16)28(41)57-11-10-31-19(37)8-9-32-26(40)23(39)29(2,3)13-50-56(47,48)53-55(45,46)49-12-18-22(52-54(42,43)44)21(38)27(51-18)36-15-35-20-24(30)33-14-34-25(20)36/h4-7,14-15,18,21-23,27,38-39H,8-13H2,1-3H3,(H,31,37)(H,32,40)(H,45,46)(H,47,48)(H2,30,33,34)(H2,42,43,44)/t18-,21-,22-,23?,27-/m1/s1

InChI Key

ATOBVMVSPXOGBP-XJJJFWNASA-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
Pentose monosaccharide
Organic pyrophosphate
Monosaccharide phosphate
Purine
Thiobenzoic acid or derivatives
Imidazopyrimidine
Benzoic acid or derivatives
Benzoyl
Toluene
Monoalkyl phosphate
Aminopyrimidine
Monocyclic benzene moiety
Fatty amide
Imidolactam
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Benzenoid
Alkyl phosphate
Phosphoric acid ester
Pyrimidine
Tetrahydrofuran
Heteroaromatic compound
Imidazole
Azole
Secondary alcohol
Secondary carboxylic acid amide
Thiocarboxylic acid ester
Carboxamide group
Amino acid or derivatives
Carbothioic s-ester
Thiocarboxylic acid or derivatives
Azacycle
Oxacycle
Organoheterocyclic compound
Sulfenyl compound
Carboxylic acid derivative
Hydrocarbon derivative
Organosulfur compound
Carbonyl group
Organic nitrogen compound
Organopnictogen compound
Organooxygen compound
Organic oxide
Primary amine
Alcohol
Amine
Organonitrogen compound
Organic oxygen compound
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: HMDB0011636)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0011636)

Source

Endogenous

Endogenous (HMDB: HMDB0011636)

Animal

Animal (HMDB: HMDB0011636)

Exogenous

Food

Food (HMDB: HMDB0011636)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0011636)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0011636)

Lipid metabolism pathway (HMDB: HMDB0011636)

Cellular process

Cell signaling (HMDB: HMDB0011636)

Biochemical process

Lipid transport (HMDB: HMDB0011636)

Role

Biological role

Energy source (HMDB: HMDB0011636)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0011636)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.33 g/L	ALOGPS
logP	0.1	ALOGPS
logP	-4.4	ChemAxon
logS	-2.4	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	21	ChemAxon
Refractivity	197.92 m³·mol⁻¹	ChemAxon
Polarizability	79.89 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

HMDB0011636

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028334

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

53481007

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Salicyloyl-CoA (CFc000007221)

MOL for CFc000007221 (Salicyloyl-CoA)

3D MOL for CFc000007221 (Salicyloyl-CoA)

3D SDF for CFc000007221 (Salicyloyl-CoA)

3D-SDF for CFc000007221 (Salicyloyl-CoA)

PDB for CFc000007221 (Salicyloyl-CoA)

3D PDB for CFc000007221 (Salicyloyl-CoA)

SMILES for CFc000007221 (Salicyloyl-CoA)

INCHI for CFc000007221 (Salicyloyl-CoA)

Structure for CFc000007221 (Salicyloyl-CoA)

3D Structure for CFc000007221 (Salicyloyl-CoA)