Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	22116
Common Name:	Procyanidin B3
Systematic Name:	(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
Synonyms:	Afzelechin-(4alpha->8)-afzelechin [PubChem Synonyms]
Exact Mass:	578.1424 (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:	C30H26O12
InChIKey:	XFZJEEAOWLFHDH-AVFWISQGSA-N
LIPID MAPS Category:	Polyketides [PK]
LIPID MAPS mainclass:	Flavonoids [PK12]
LIPID MAPS subclass:	Proanthocyanidins [PK1203]
SMILES:	c1cc(c(cc1[C@@H]1[C@H](Cc2c(cc(c([C@@H]3c4c(cc(cc4O[C@H](c4ccc(c(c4)O)O)[C@H]3O)O)O)c2O1)O)O)O)O)O
Studies:	Available studies(via PubChem CID)

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All Database Links Calculated Properties Human Pathways

External database links:

PubChem CID:	146798
LIPID MAPS ID:	LMPK12030003
CHEBI ID:	75630
HMDB ID:	HMDB0033974
KEGG ID:	C10209
Chemspider ID:	129476
MetaCyc ID:	CPD-7631
EPA CompTox DB:	DTXCID30218595
Plant Metabolite Hub(Pmhub):	MS000010997

Calculated physicochemical properties (?):

Heavy Atoms:	42
Rings:	6
Aromatic Rings:	4
Rotatable Bonds:	3
van der Waals Molecular volume:	483.60 Å3 molecule-1
Toplogical Polar Sufrace Area:	224.90 Å2 molecule-1
Hydrogen Bond Donors:	10
Hydrogen Bond Acceptors:	12
logP:	3.57
Molar Refractivity:	144.41
Fraction sp3 Carbons:	0.20
sp3 Carbons:	6

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