Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	22653
Common Name:	Rotenone
Systematic Name:	(2R,6aS,12aS)-1,2,6,6a,12,12a- hexahydro-2-isopropenyl-8,9- dimethoxychromeno[3,4-b] furo(2,3-h)chromen-6-one
RefMet Name:	Rotenone
Synonyms:	Tubotoxin [PubChem Synonyms]
Exact Mass:	394.1416 (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:	C23H22O6
InChIKey:	JUVIOZPCNVVQFO-HBGVWJBISA-N
LIPID MAPS Category:	Polyketides [PK]
LIPID MAPS mainclass:	Flavonoids [PK12]
LIPID MAPS subclass:	Rotenoid flavonoids [PK1206]
Massbank MS spectra:	View MS spectra
SMILES:	C=C(C)[C@H]1Cc2c(ccc3C(=O)[C@H]4c5cc(c(cc5OC[C@H]4Oc23)OC)OC)O1
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:	6758
LIPID MAPS ID:	LMPK12060007
CHEBI ID:	28201
HMDB ID:	HMDB0034436
KEGG ID:	C07593
Chemspider ID:	6500
MetaCyc ID:	CPD-5741
EPA CompTox DB:	DTXCID80209099
Plant Metabolite Hub(Pmhub):	MS000002391

Calculated physicochemical properties (?):

Heavy Atoms:	29
Rings:	5
Aromatic Rings:	2
Rotatable Bonds:	3
van der Waals Molecular volume:	354.48 Å3 molecule-1
Toplogical Polar Sufrace Area:	69.43 Å2 molecule-1
Hydrogen Bond Donors:	0
Hydrogen Bond Acceptors:	6
logP:	4.56
Molar Refractivity:	107.42
Fraction sp3 Carbons:	0.35
sp3 Carbons:	8

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