Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	53398
Common Name:	Psilocybin
Systematic Name:	3-[2-(dimethylamino)ethyl]-1H-indol-4-yl dihydrogen phosphate
RefMet Name:	Psilocybin
Synonyms:	4-phosphoryloxy-N,N-dimethyltryptamine; Indocybin; O-phosphoryl-4-hydroxy-N,N-dimethyltryptamine; Psilocybin; Psilocybine; psilocin phosphate ester [PubChem Synonyms]
Exact Mass:	284.0926 (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:	C12H17N2O4P
InChIKey:	QVDSEJDULKLHCG-UHFFFAOYSA-N
ClassyFire superclass:	Organoheterocyclic compounds [C0000002]
ClassyFire class:	Indoles and derivatives [C0000211]
ClassyFire subclass:	Tryptamines and derivatives [C0000183]
ClassyFire direct parent:	Tryptamines and derivatives [C0000183]
MoNA MS spectra:	View MS spectra
SMILES:	CN(C)CCc1c[nH]c2cccc(c12)OP(=O)(O)O
Studies:	Available studies (via RefMet name)

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All Database Links Calculated Properties Human Pathways

Calculated physicochemical properties (?):

Heavy Atoms:	19
Rings:	2
Aromatic Rings:	2
Rotatable Bonds:	5
van der Waals Molecular volume:	236.07 Å3 molecule-1
Toplogical Polar Sufrace Area:	85.79 Å2 molecule-1
Hydrogen Bond Donors:	3
Hydrogen Bond Acceptors:	5
logP:	2.21
Molar Refractivity:	73.38
Fraction sp3 Carbons:	0.33
sp3 Carbons:	4

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