Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	1887
Common Name:	Lipoic acid
Systematic Name:	1,2-dithiolane-3R-pentanoic acid
RefMet Name:	Lipoic acid
Synonyms:	R-Lipoic acid [PubChem Synonyms]
Exact Mass:	206.0435 (neutral)    Calculate m/z: (Choose adduct) [M+H]+ [M+H-H2O]+ [M.]+ [M+2H]2+ [M+3H]3+ [M+4H]4+ [M+K]+ [M+2K]2+ [M-H+2K]+ [M+Na]+ [M+2Na]2+ [M-H+2Na]+ [M+Li]+ [M+2Li]2+ [M+NH4]+ [M-H]- [M-2H]2- [M-3H]3- [M-4H]4- [M+Cl]- [M+OAc]- [M+HCOO]- M(neutral)
Formula:	C8H14O2S2
InChIKey:	AGBQKNBQESQNJD-SSDOTTSWSA-N
LIPID MAPS Category:	Fatty Acyls [FA]
LIPID MAPS mainclass:	Fatty Acids and Conjugates [FA01]
LIPID MAPS subclass:	Thia fatty acids [FA0113]
Massbank MS spectra:	View MS spectra
NP-MRD NMR spectra:	View NMR spectra
SMILES:	C(CCC(=O)O)C[C@@H]1CCSS1
Studies:	Available studies (via RefMet name)

Select appropriate tab below to view additional details:

All Database Links Calculated Properties Human Pathways

External database links:

PubChem CID:	6112
LIPID MAPS ID:	LMFA01130001
CHEBI ID:	30314
HMDB ID:	HMDB0001451
KEGG ID:	C16241
Chemspider ID:	5886
METLIN ID:	126
MetaCyc ID:	LIPOIC-ACID
NP-MRD ID(NMR):	NP0000443
Plant Metabolite Hub(Pmhub):	MS000000280

Calculated physicochemical properties (?):

Heavy Atoms:	12
Rings:	1
Aromatic Rings:	0
Rotatable Bonds:	5
van der Waals Molecular volume:	186.56 Å3 molecule-1
Toplogical Polar Sufrace Area:	37.30 Å2 molecule-1
Hydrogen Bond Donors:	1
Hydrogen Bond Acceptors:	2
logP:	3.36
Molar Refractivity:	55.56
Fraction sp3 Carbons:	0.88
sp3 Carbons:	7

Human Pathway links:

HMDB and KEGG pathways containing this metabolite

REACTOME pathways containing this metabolite

References

LIPID MAPS classification: "Update of the LIPID MAPS comprehensive classification system for lipids", Fahy E, Subramaniam S, Murphy RC, Nishijima M, Raetz CR, Shimizu T, Spener F, van Meer G, Wakelam MJ, and Dennis EA, J. Lipid Res. (2009) 50: S9-S14. DOI: 10.1194/jlr.R800095-JLR200
ClassyFire classification: "ClassyFire: automated chemical classification with a comprehensive, computable taxonomy", Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS, J. Cheminformatics (2016) 8:61. DOI: 10.1186/s13321-016-0174-y