Showing Compound Lipoamide (FDB022340)

Record Information

Version

1.0

Creation date

2011-09-21 00:12:27 UTC

Update date

2019-11-26 03:21:02 UTC

Primary ID

FDB022340

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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	ChEBI
alpha-Lipoic acid amide	ChEBI
Lipoacin	ChEBI
Thioctamide	ChEBI
Thioctic acid amide	ChEBI
Vitamin N	ChEBI
a-Lipoate amide	Generator
a-Lipoic acid amide	Generator
alpha-Lipoate amide	Generator
Α-lipoate amide	Generator
Α-lipoic acid amide	Generator
Thioctate amide	Generator
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
alpha-Lipoate	HMDB
alpha-Lipoic acid	HMDB
DL-6-Thioctic amide	HMDB
DL-Lipoamide	HMDB
Lipamide	HMDB
Lipoamid	HMDB
Lipoicin	HMDB
Lipozyme	HMDB
Lypoaran	HMDB
Pathoclon	HMDB
Thioami	HMDB
Thioctamid	HMDB
Thiotomin	HMDB
Ticolin	HMDB
1,2-Dithiolane-3-valeramide	HMDB
6,8-Thioctic amide	HMDB
alpha-Lipoic amide	HMDB
Lipoamide, (+-)-isomer	HMDB
5-(1,2-dithiolan-3-yl)-pentanamide	hmdb
5-(1,2-dithiolan-3-yl)pentanamide	hmdb
Alpha-lipoic acid amide	hmdb
dl-6-Thioctic amide	hmdb
DL-lipoamide	hmdb
Thioctic acid amide (jan)	hmdb
Vitamin n	hmdb
α-lipoate amide	Generator
α-lipoic acid amide	Generator

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
logP	2.3	ALOGPS
logP	1.31	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	16.45	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	56.19 m³·mol⁻¹	ChemAxon
Polarizability	22.38 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Classification

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

Substituents

Lipoamide
Fatty amide
Fatty acyl
1,2-dithiolane
Carboxamide group
Organic disulfide
Primary carboxylic acid amide
Carboxylic acid derivative
Carbonyl group
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:17460 )
dithiolanes (CHEBI:17460 )
Primary amides (LMFA08010006 )
a small molecule (LIPOAMIDE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Plant:

Animal

Biological location:

Tissue and substructures:

Placenta

Subcellular:

Biofluid and excreta:

Saliva

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Lipoamide, 2 TMS, GC-MS Spectrum	splash10-014i-6963000000-7e1887d53c2801b09961	Spectrum
GC-MS	Lipoamide, 1 TMS, GC-MS Spectrum	splash10-017l-3920000000-a3a7a08acf06d41c9b73	Spectrum
GC-MS	Lipoamide, non-derivatized, GC-MS Spectrum	splash10-014i-6963000000-7e1887d53c2801b09961	Spectrum
GC-MS	Lipoamide, non-derivatized, GC-MS Spectrum	splash10-017l-3920000000-a3a7a08acf06d41c9b73	Spectrum
GC-MS	Lipoamide, non-derivatized, GC-MS Spectrum	splash10-014i-1910000000-b6ee336856e354af8114	Spectrum
GC-MS	Lipoamide, non-derivatized, GC-MS Spectrum	splash10-00di-3900000000-60cad9dd198c3ad64ed7	Spectrum
Predicted GC-MS	Lipoamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f96-9800000000-ac967ad86beefc26c983	Spectrum
Predicted GC-MS	Lipoamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-0900000000-24fca44fc025dbd6be18	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0ziu-9700000000-7dfd23f450bdfd581100	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-056u-9000000000-13583c4eb6b06a56c392	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-052r-2920000000-a4fb7176abf63e581f5e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-000i-2900000000-10a079a84f024494ae23	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0zfr-9800000000-b01332176d6829b1eaa1	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0udl-9400000000-7a03c741edae36dff9cf	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0a5c-9100000000-7b44dfbfcbb0cc516254	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-0900000000-50512172ce038bce2995	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-03di-0900000000-7652a33c17a37b6914aa	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0udi-0900000000-0df59a6540bede8a4a79	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-052r-2920000000-a4fb7176abf63e581f5e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-000i-2900000000-158c946037c5d7bb3e50	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0zfr-9800000000-b01332176d6829b1eaa1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0udl-9400000000-7a03c741edae36dff9cf	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , positive	splash10-0a5c-9100000000-7b44dfbfcbb0cc516254	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-000i-0900000000-fa779b1c88469a732321	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-000i-1900000000-9e4b6873b24c66cf9f69	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01p9-0900000000-b37ce6b25b9feef09b96	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4r-0940000000-d79e1aa52057e567d71f	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-3900000000-abd8148048c5f282d889	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0adr-9500000000-9769c619660ab6af46d2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zml-1920000000-79d57d488cb8fbc804a3	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fdo-4910000000-d264eaf6e242c36bc563	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-289d2f20046f7819a7ca	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, methanol, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, methanol, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

17460

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00962

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

34384

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Lipoamide

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Glycine dehydrogenase [decarboxylating], mitochondrial	GLDC	P23378
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial	PDHA1	P08559
2-oxoglutarate dehydrogenase, mitochondrial	OGDH	Q02218