ChemFOnt: Showing chemical card for S-(3-Methylbutanoyl)-dihydrolipoamide-E (CFc000002976)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:47:59 UTC

Chemfont ID

CFc000002976

Molecule Identification

Common Name

S-(3-Methylbutanoyl)-dihydrolipoamide-E

Definition

S-(3-Methylbutanoyl)-dihydrolipoamide-E is an intermediate in valine, leucine and isoleucine degradation(KEGG ID C15975 ). It is the second to last step in the synthesis of branched chain fatty acid and is converted from 3-methyl-hydroxybutyl-ThPP via the enzyme 2-oxoisovalerate dehydrogenase [EC:1.2.4.4]. It is then converted to 3-methylbutanoyl-CoA via the enzyme dihydrolipoyllysine-residue (2-methylpropanoyl)transferase[EC:2.3.1.168].

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
S-(3-Methylbutanoyl)-dihydrolipoamide	ChEBI
S-(3-Methylbutanoyl)dihydrolipoyllysine	HMDB
[Dihydrolipoyllysine-residue (2-methylpropanoyl)transferase]	HMDB

Chemical Formula

C₁₃H₂₅NO₂S₂

Average Molecular Weight

291.473

Monoisotopic Molecular Weight

291.132670429

IUPAC Name

8-[(3-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide

Traditional Name

8-[(3-methylbutanoyl)sulfanyl]-6-sulfanyloctanamide

CAS Registry Number

None

SMILES

CC(C)CC(=O)SCCC(S)CCCCC(N)=O

InChI Identifier

InChI=1S/C13H25NO2S2/c1-10(2)9-13(16)18-8-7-11(17)5-3-4-6-12(14)15/h10-11,17H,3-9H2,1-2H3,(H2,14,15)

InChI Key

KMUSXGCRMMQDBP-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acyl thioesters. These are thioester derivatives of a fatty acid with the general formula RC(=O)SR', where R is the fatty acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Fatty acyl thioesters

Alternative Parents

Substituents

Fatty acyl thioester
Fatty amide
Carboxamide group
Primary carboxylic acid amide
Thiocarboxylic acid ester
Carbothioic s-ester
Alkylthiol
Carboxylic acid derivative
Thiocarboxylic acid or derivatives
Sulfenyl compound
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic oxide
Organic nitrogen compound
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

S-(methylbutanoyl)dihydrolipoamide (CHEBI:27462 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0006867)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0006867)

Source

Endogenous

Endogenous (HMDB: HMDB0006867)

Animal

Animal (HMDB: HMDB0006867)

Exogenous

Food

Food (HMDB: HMDB0006867)

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)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0006867)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0006867)
Valine, Leucine, and Isoleucine Degradation (PathBank: SMP0063689)

Disease pathway

2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120439)
Methylmalonate Semialdehyde Dehydrogenase Deficiency (PathBank: SMP0120523)
Isovaleric Acidemia (PathBank: SMP0120589)
3-Methylglutaconic Aciduria Type I (PathBank: SMP0120663)
Beta-Ketothiolase Deficiency (PathBank: SMP0120679)
3-Hydroxyisobutyric Aciduria (PathBank: SMP0120806)
3-Methylcrotonyl-CoA Carboxylase Deficiency Type I (PathBank: SMP0120441)
3-Methylglutaconic Aciduria Type IV (PathBank: SMP0120444)
Methylmalonic Aciduria (PathBank: SMP0120525)
3-Hydroxy-3-methylglutaryl-CoA Lyase Deficiency (PathBank: SMP0120661)
3-Methylglutaconic Aciduria Type III (PathBank: SMP0120664)
Maple Syrup Urine Disease (PathBank: SMP0120516)
Propionic Acidemia (PathBank: SMP0120537)
Isobutyryl-CoA Dehydrogenase Deficiency (PathBank: SMP0120588)
Isovaleric Aciduria (PathBank: SMP0120723)
3-Hydroxyisobutyric Acid Dehydrogenase Deficiency (PathBank: SMP0120586)
2-Methyl-3-hydroxybutryl-CoA Dehydrogenase Deficiency (PathBank: SMP0000137)

Lipid metabolism pathway (HMDB: HMDB0006867)

Biochemical process

Lipid transport (HMDB: HMDB0006867)

Role

Biological role

Energy source (HMDB: HMDB0006867)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	3.35	ALOGPS
logP	2.67	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	10.06	ChemAxon
pKa (Strongest Basic)	-0.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	60.16 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	81 m³·mol⁻¹	ChemAxon
Polarizability	33.89 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0006867

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024123

KNApSAcK ID

Not Available

Chemspider ID

389466

KEGG Compound ID

C05119

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440566

PDB ID

Not Available

ChEBI ID

27462

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for S-(3-Methylbutanoyl)-dihydrolipoamide-E (CFc000002976)

MOL for CFc000002976 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

3D MOL for CFc000002976 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

3D SDF for CFc000002976 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

3D-SDF for CFc000002976 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

PDB for CFc000002976 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

3D PDB for CFc000002976 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

SMILES for CFc000002976 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

INCHI for CFc000002976 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

Structure for CFc000002976 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)

3D Structure for CFc000002976 (S-(3-Methylbutanoyl)-dihydrolipoamide-E)