Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	67825
Common Name:	Lupulone
Systematic Name:	3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
RefMet Name:	Lupulone
Synonyms:	Lupulon; beta-Bitter acid; beta-Lupulic acid; B'' -Acid; EINECS 207-405-3 [PubChem Synonyms]
Exact Mass:	414.2770 (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:	C26H38O4
InChIKey:	LSDULPZJLTZEFD-UHFFFAOYSA-N
ClassyFire superclass:	Organic acids and derivatives [C0000264]
ClassyFire class:	Vinylogous acids [C0003889]
ClassyFire subclass:	Vinylogous acids [C0003889]
ClassyFire direct parent:	Aliphatic homomonocyclic compounds
Massbank MS spectra:	View MS spectra
SMILES:	CC(=CCC1=C(C(CC=C(C)C)(CC=C(C)C)C(=O)C(=C1O)C(=O)CC(C)C)O)C
Studies:	Available studies (via RefMet name)

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All Database Links Calculated Properties Human Pathways

Calculated physicochemical properties (?):

Heavy Atoms:	30
Rings:	1
Aromatic Rings:	0
Rotatable Bonds:	9
van der Waals Molecular volume:	462.68 Å3 molecule-1
Toplogical Polar Sufrace Area:	74.60 Å2 molecule-1
Hydrogen Bond Donors:	2
Hydrogen Bond Acceptors:	4
logP:	6.86
Molar Refractivity:	123.36
Fraction sp3 Carbons:	0.54
sp3 Carbons:	14

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