Showing Compound Dihydrolipoamide (FDB022352)

Record Information

Version

1.0

Creation date

2011-09-21 00:12:37 UTC

Update date

2019-11-26 03:21:02 UTC

Primary ID

FDB022352

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Dihydrolipoamide

Description

Dihydrolipoamide is an intermediate in glycolysis/gluconeogenesis, citrate cycle (TCA cycle), alanine, aspartate and pyruvate metabolism, and valine, leucine and isoleucine degradation (KEGG ID C00579). It is converted to lipoamide via the enzyme dihydrolipoamide dehydrogenase [EC:1.8.1.4]. Dihydrolipoamide is also a substrate of enzyme Acyltransferases [EC 2.3.1.-]. (KEGG) [HMDB]. Dihydrolipoamide is found in many foods, some of which are enokitake, mugwort, welsh onion, and tea.

CAS Number

3884-47-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

Show entries

Search:

Synonym	Source
6,8-Bis-sulfanyloctanamide	HMDB
6,8-bis-sulfanyloctanamide	hmdb
6,8-Dimercapto-octanamide	HMDB
6,8-dimercapto-Octanamide	hmdb
6,8-Dimercaptooctanamide	ChEBI
6,8-dimercaptooctanamide	hmdb
6,8-Disulfanyloctanamide	HMDB
6,8-disulfanyloctanamide	hmdb
dihydrolipoamide	hmdb
Dihydrolipoamide, (+-)-isomer	HMDB

Showing 1 to 10 of 11 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.099 g/L	ALOGPS
logP	2.22	ALOGPS
logP	1.44	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	6.68	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	44.08 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	68.7 m³·mol⁻¹	ChemAxon
Polarizability	23.77 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

Chemical Formula

C8H17NOS2

IUPAC name

6,8-disulfanyloctanimidic acid

InChI Identifier

InChI=1S/C8H17NOS2/c9-8(10)4-2-1-3-7(12)5-6-11/h7,11-12H,1-6H2,(H2,9,10)

InChI Key

VLYUGYAKYZETRF-UHFFFAOYSA-N

Isomeric SMILES

OC(=N)CCCCC(S)CCS

Average Molecular Weight

207.357

Monoisotopic Molecular Weight

207.075155551

Classification

Description

Belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

Fatty amides

Alternative Parents

Substituents

Fatty amide
Primary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Alkylthiol
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid amide (CHEBI:17694 )
dithiol (CHEBI:17694 )
a small molecule (DIHYDROLIPOAMIDE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Source:

Biological:

Animal

Plant:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Biochemical pathway:

Lipid metabolism pathway

Chemical reaction:

Lipid peroxidation

Role

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Dihydrolipoamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9700000000-936a7170a2da09aecf11	Spectrum
Predicted GC-MS	Dihydrolipoamide, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9410000000-9f1410bc40e59db39d21	Spectrum
Predicted GC-MS	Dihydrolipoamide, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydrolipoamide, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydrolipoamide, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydrolipoamide, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydrolipoamide, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydrolipoamide, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydrolipoamide, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Dihydrolipoamide, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-0940000000-f34746a5ea022152ba75	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-1900000000-99beaa28d55837788743	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0m2i-9400000000-53152f2f29c03cd0cbcd	2015-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ab9-1960000000-1e45a79f64407fb4dea8	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ab9-5930000000-297b157da8ed63567faa	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-82e7dacb48c8cab103d4	2015-09-15	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0ab9-0950000000-6272c55454b18f718c5d	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0w29-2900000000-a19052123ea01afd8613	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002v-9300000000-c0ae302dda03ee321d60	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0090000000-1361b5d8ba6f1d1a13ef	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pb9-5940000000-00e811c07c89a8896c7d	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

643

ChEMBL ID

Not Available

KEGG Compound ID

C00579

Pubchem Compound ID

663

Pubchem Substance ID

Not Available

ChEBI ID

17694

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00985

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

35406

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

Dihydrolipoamide

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Show entries

Search:

Name	Gene Name	UniProt ID
Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial	DLST	P36957
Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial	DBT	P11182

Showing 1 to 2 of 2 entries

Pathways