MiMeDB: Showing metabocard for Dihydrolipoamide (MMDBc0029523)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:25:51 UTC

Update Date

2024-10-13 12:21:51 UTC

Metabolite ID

MMDBc0029523

Metabolite Identification

Common Name

Dihydrolipoamide

Description

Dihydrolipoamide is a member of the chemical class known as N-acyl Amines. These are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. Dihydrolipoamide is a molecule produced by the action of dihydrolipoyl dehydrogenase upon lipoamide.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Molecular Formula

C₈H₁₇NOS₂

Average Mass

207.357

Monoisotopic Mass

207.075155551

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

3884-47-7

SMILES

Not Available

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

Chemical Taxonomy

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191728	Dihydrolipoyl dehydrogenase, mitochondrial	Unknown	P09622	Homo sapiens
MMDBp0192557	Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrial	Enzyme	P36957	Homo sapiens
MMDBp0193802	Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrial	Enzyme	P11182	Homo sapiens
MMDBp0194147	Dihydrolipoamide S-acetyltransferase	Enzyme	Q86YI5	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0001273	S(8)-aminomethyldihydrolipoamide	Dihydrolipoamide	aminomethyltransferase	VMH	15355973
MMDBr0001274	Dihydrolipoamide	Lipoamide	aminomethyltransferase	VMH; KEGG	15355973
MMDBr0002596	S-Acetyldihydrolipoamide	Dihydrolipoamide	dihydrolipoamide S-acetyltransferase	VMH	12108679 14741190
MMDBr0002597	Dihydrolipoamide	(S)-Succinyldihydrolipoamide	dihydrolipoamide S-succinyltransferase (E2 component of 2-oxo-glutarate complex)	VMH	8076640 9620315
MMDBr0002598	S-Glutaryldihydrolipoamide	Dihydrolipoamide	dihydrolipoamide S-succinyltransferase (E2 component of 2-oxo-glutarate complex)	VMH	9620315
MMDBr0002602	S-(2-Methylpropionyl)-dihydrolipoamide-E	Dihydrolipoamide	dihydrolipoamide branched chain transacylase E2	VMH	10966480 1429740 1943690 7963542
MMDBr0002619	S-(2-Methylbutanoyl)-dihydrolipoamide	2-Methylbutyryl-CoA	dihydrolipoamide branched chain transacylase E2	VMH	1943690
MMDBr0002652	S-(3-Methylbutanoyl)-dihydrolipoamide-E	Dihydrolipoamide	dihydrolipoamide branched chain transacylase E2	VMH	1943690
MMDBr0004704	Dihydrolipoamide	S-(2-Methylpropionyl)-dihydrolipoamide-E	branched chain keto acid dehydrogenase E1, beta polypeptide	VMH	2699399 9665099
MMDBr0007131	S-Acetyldihydrolipoamide	Dihydrolipoamide	Not Available	VMH	30371894
MMDBr0007935	Dihydrolipoamide	Lipoamide	Not Available	VMH	30371894
MMDBr0008015	Dihydrolipoamide	(S)-Succinyldihydrolipoamide	Not Available	VMH	30371894
MMDBr0008349	2-Methylbutyryl-CoA	S-(2-Methylbutanoyl)-dihydrolipoamide	Not Available	VMH	30371894
MMDBr0008350	Dihydrolipoamide	S-(2-Methylbutanoyl)-dihydrolipoamide	Not Available	VMH	30371894
MMDBr0008354	Dihydrolipoamide	S-(2-Methylpropionyl)-dihydrolipoamide-E	Not Available	VMH	30371894
MMDBr0010336	(R)-Lipoic acid	Dihydrolipoamide	dihydrolipoamide dehydrogenase	VMH	30371894
MMDBr0010914	Dihydrolipoamide	(S)-Succinyldihydrolipoamide	Not Available	VMH	30371894

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	170	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	331	Human feces; Human pleural fluid plaque; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Pig ; Cattle	Metabolic reconstruction
Bacteria	Actinobacteria	110	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human subgingival plaque; Human mucosa; Human saliva	Metabolic reconstruction
Bacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Bacteroidetes	119	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human supragingival plaque; Human subgingival plaque	Metabolic reconstruction
Bacteria	Synergistetes	4	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	18	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	5		Metabolic reconstruction
Bacteria	Candidatus melainabacteria	1	Human feces	Metabolic reconstruction
Bacteria	Tenericutes	1	Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Activity	Data Source	Reference
Drugs	Antimicrobial	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

McMillan PJ, Stimmler LM, Foth BJ, McFadden GI, Muller S: The human malaria parasite Plasmodium falciparum possesses two distinct dihydrolipoamide dehydrogenases. Mol Microbiol. 2005 Jan;55(1):27-38. doi: 10.1111/j.1365-2958.2004.04398.x. [PubMed:15612914 ]
Deres P, Halmosi R, Toth A, Kovacs K, Palfi A, Habon T, Czopf L, Kalai T, Hideg K, Sumegi B, Toth K: Prevention of doxorubicin-induced acute cardiotoxicity by an experimental antioxidant compound. J Cardiovasc Pharmacol. 2005 Jan;45(1):36-43. doi: 10.1097/00005344-200501000-00007. [PubMed:15613977 ]
Li XJ, Grunwald D, Mathieu J, Morel F, Stasia MJ: Crucial role of two potential cytosolic regions of Nox2, 191TSSTKTIRRS200 and 484DESQANHFAVHHDEEKD500, on NADPH oxidase activation. J Biol Chem. 2005 Apr 15;280(15):14962-73. doi: 10.1074/jbc.M500226200. Epub 2005 Jan 31. [PubMed:15684431 ]
Kim H: Asparagine-473 residue is important to the efficient function of human dihydrolipoamide dehydrogenase. J Biochem Mol Biol. 2005 Mar 31;38(2):248-52. doi: 10.5483/bmbrep.2005.38.2.248. [PubMed:15826505 ]
Brautigam CA, Chuang JL, Tomchick DR, Machius M, Chuang DT: Crystal structure of human dihydrolipoamide dehydrogenase: NAD+/NADH binding and the structural basis of disease-causing mutations. J Mol Biol. 2005 Jul 15;350(3):543-52. doi: 10.1016/j.jmb.2005.05.014. [PubMed:15946682 ]

Showing metabocard for Dihydrolipoamide (MMDBc0029523)

MOL for #<Metabolite:0x00007f53bb03ab68>

3D MOL for #<Metabolite:0x00007f53bb03ab68>

3D SDF for #<Metabolite:0x00007f53bb03ab68>

3D-SDF for #<Metabolite:0x00007f53bb03ab68>

PDB for #<Metabolite:0x00007f53bb03ab68>

3D PDB for #<Metabolite:0x00007f53bb03ab68>

SMILES for #<Metabolite:0x00007f53bb03ab68>

INCHI for #<Metabolite:0x00007f53bb03ab68>

Structure for #<Metabolite:0x00007f53bb03ab68>

3D Structure for #<Metabolite:0x00007f53bb03ab68>