FComEx: Lipoamide (PC000791)

Record Information

Version

1.0

Creation date

2015-10-09 22:32:40 UTC

Update date

2017-01-19 02:36:36 UTC

FoodComEx ID

PC000791

FoodDB Record

FDB022340

Chemical Information

Name

Lipoamide

Description

Lipoamide is the oxidized form of glutathione. (PMID:8957191) Lipoamide is a trivial name for 6,8-dithiooctanoic amide. It is 6,8-dithiooctanoic acid's functional form where the carboxyl group is attached to protein (or any other amine) by an amide linkage (containing -NH2) to an amino group. Lipoamide forms a thioester bond, oxidizing the disulfide bond, with acetaldehyde (pyruvate after it has been decarboxylated). It then transfers the acetaldehyde group to CoA which can then continue in the TCA cycle. Lipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG:C00248). It is generated from dihydrolipoamide via the enzyme dihydrolipoamide dehydrogenase (EC:1.8.1.4) and then converted to S-glutaryl-dihydrolipoamide via the enzyme oxoglutarate dehydrogenase (EC:1.2.4.2). [HMDB]. Lipoamide is found in many foods, some of which are pepper (c. frutescens), black crowberry, common salsify, and wild leek.

CAS Number

940-69-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1,2-Dithiolane-3-pentanamide	hmdb
5-(1,2-dithiolan-3-yl)-pentanamide	hmdb
5-(1,2-dithiolan-3-yl)pentanamide	hmdb
5-(1,2-Dithiolan-3-yl)valeramide	hmdb
5-(Dithiolan-3-yl)valeramide	hmdb
a-Lipoate amide	Generator
a-Lipoic acid amide	Generator
alpha-Lipoate	HMDB
alpha-Lipoate amide	Generator
alpha-Lipoic acid	HMDB
Alpha-lipoic acid amide	hmdb
dl-6-Thioctic amide	hmdb
DL-lipoamide	hmdb
Lipamide	hmdb
Lipoacin	hmdb
Lipoamid	hmdb
Lipoicin	hmdb
Lipozyme	hmdb
Lypoaran	hmdb
Pathoclon	hmdb
Thioami	hmdb
Thioctamid	hmdb
Thioctamide	hmdb
Thioctate amide	Generator
Thioctic acid amide	hmdb
Thioctic acid amide (jan)	hmdb
Thiotomin	hmdb
Ticolin	hmdb
Vitamin n	hmdb
α-lipoate amide	Generator
α-lipoic acid amide	Generator

Chemical Formula

C8H15NOS2

IUPAC name

5-(1,2-dithiolan-3-yl)pentanamide

InChI Identifier

InChI=1S/C8H15NOS2/c9-8(10)4-2-1-3-7-5-6-11-12-7/h7H,1-6H2,(H2,9,10)

InChI Key

FCCDDURTIIUXBY-UHFFFAOYSA-N

Isomeric SMILES

NC(=O)CCCCC1CCSS1

Average Molecular Weight

205.341

Monoisotopic Molecular Weight

205.059505487

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lipoamides. Lipoamides are compounds containing a lipoamide moiety, which consists of a pentanamide attached to the C3 carbon atom of a 1,2-dithiolane ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dithiolanes

Sub Class

Lipoamides

Direct Parent

Lipoamides

Alternative Parents