Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	52348
Common Name:	(S)-lipoic acid
Systematic Name:	5-[(3S)-dithiolan-3-yl]pentanoic acid
RefMet Name:	(S)-Lipoic acid
Synonyms:	(S)-alpha-lipoic acid; L-1,2-dithiolane 3-valeric acid; L-6,8-thioctic acid; L-6-thioctic acid; S-LA; SLA [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-ZETCQYMHSA-N
ClassyFire superclass:	Organoheterocyclic compounds
ClassyFire class:	Dithiolanes
ClassyFire subclass:	Lipoic acids and derivatives
ClassyFire direct parent:	Lipoic acids and derivatives
NP-MRD NMR spectra:	View NMR spectra
SMILES:	C(CCC(=O)O)C[C@H]1CCSS1
Studies:	Available studies (via RefMet name)

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External database links:

PubChem CID:	445125
CHEBI ID:	43796
HMDB ID:	HMDB0014312
KEGG ID:	C16241
NP-MRD ID(NMR):	NP0002784

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
NPClassifier classification: "NPClassifier: A Deep Neural Network-Based Structural Classification Tool for Natural Products", Kim HW, Wang M, Leber CA, Nothias LF, Reher R, Kang KB, van der Hooft JJJ, Dorrestein PC, Gerwick WH and Cottrell GW. J Nat Prod. 2021 Nov 26;84(11):2795-2807.DOI: 10.1021/acs.jnatprod.1c00399.