ChemFOnt: Showing chemical card for Valproyl-CoA (CFc000008205)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:52 UTC

Chemfont ID

CFc000008205

Molecule Identification

Common Name

Valproyl-CoA

Definition

Valproyl-CoA, a valproate metabolite previously identified in liver, may accumulate in brain as a result of normal fatty acid turnover processes. Valproyl CoA could contribute to valproate's antiepileptic activity by stimulating Na+, K+-ATPase activity when brain ATP concentration is low. Valproyl-CoA and to a much lesser extent 3-keto-valproyl-CoA are the main metabolites of VPA in mitochondria.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Propylpentanoyl CoA	HMDB
2-Propylpentanoyl coenzyme A	HMDB
Valproyl-coenzyme A	MeSH, HMDB

Chemical Formula

C₂₉H₅₀N₇O₁₇P₃S

Average Molecular Weight

893.73

Monoisotopic Molecular Weight

893.219673435

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-propylpentanoyl)sulfanyl]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-propylpentanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

None

SMILES

CCCC(CCC)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/C29H50N7O17P3S/c1-5-7-17(8-6-2)28(41)57-12-11-31-19(37)9-10-32-26(40)23(39)29(3,4)14-50-56(47,48)53-55(45,46)49-13-18-22(52-54(42,43)44)21(38)27(51-18)36-16-35-20-24(30)33-15-34-25(20)36/h15-18,21-23,27,38-39H,5-14H2,1-4H3,(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

UCIOSJWVYJWBEO-XJJJFWNASA-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

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0013115)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013115)

Source

Endogenous

Endogenous (HMDB: HMDB0013115)

Animal

Animal (HMDB: HMDB0013115)

Exogenous

Food

Food (HMDB: HMDB0013115)

Exogenous (HMDB: HMDB0013115)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0013115)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0013115)

Lipid metabolism pathway (HMDB: HMDB0013115)

Cellular process

Cell signaling (HMDB: HMDB0013115)

Biochemical process

Lipid transport (HMDB: HMDB0013115)

Role

Biological role

Energy source (HMDB: HMDB0013115)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013115)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	3.56 g/L	ALOGPS
logP	0.48	ALOGPS
logP	-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	25	ChemAxon
Refractivity	199.81 m³·mol⁻¹	ChemAxon
Polarizability	82.7 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

HMDB0013115

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029291

KNApSAcK ID

Not Available

Chemspider ID

8638852

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10463441

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Valproyl-CoA (CFc000008205)

MOL for CFc000008205 (Valproyl-CoA)

3D MOL for CFc000008205 (Valproyl-CoA)

3D SDF for CFc000008205 (Valproyl-CoA)

3D-SDF for CFc000008205 (Valproyl-CoA)

PDB for CFc000008205 (Valproyl-CoA)

3D PDB for CFc000008205 (Valproyl-CoA)

SMILES for CFc000008205 (Valproyl-CoA)

INCHI for CFc000008205 (Valproyl-CoA)

Structure for CFc000008205 (Valproyl-CoA)

3D Structure for CFc000008205 (Valproyl-CoA)