Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	43529
Common Name:	Yohimbine
Systematic Name:	methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate
Synonyms:	[PubChem Synonyms]
Exact Mass:	354.1943 (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:	C21H26N2O3
InChIKey:	BLGXFZZNTVWLAY-SCYLSFHTSA-N
ClassyFire superclass:	Alkaloids and derivatives [C0000279]
ClassyFire class:	Yohimbine alkaloids [C0001786]
ClassyFire subclass:	Yohimbine alkaloids [C0001786]
ClassyFire direct parent:	Aromatic heteropolycyclic compounds
Massbank MS spectra:	View MS spectra
SMILES:	COC(=O)[C@@H]1[C@H]2C[C@H]3c4c(CCN3C[C@@H]2CC[C@@H]1O)c1ccccc1[nH]4
Studies:	-

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All Database Links Calculated Properties Human Pathways

External database links:

PubChem CID:	8969
CHEBI ID:	10093
HMDB ID:	HMDB0015464
KEGG ID:	C09256
Chemspider ID:	8622
EPA CompTox DB:	DTXCID80208082
Plant Metabolite Hub(Pmhub):	MS000000702

Calculated physicochemical properties (?):

Heavy Atoms:	26
Rings:	5
Aromatic Rings:	2
Rotatable Bonds:	2
van der Waals Molecular volume:	323.43 Å3 molecule-1
Toplogical Polar Sufrace Area:	65.56 Å2 molecule-1
Hydrogen Bond Donors:	2
Hydrogen Bond Acceptors:	4
logP:	3.35
Molar Refractivity:	100.08
Fraction sp3 Carbons:	0.57
sp3 Carbons:	12

Human Pathway links:

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