Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	50750
Common Name:	3-phosphoshikimic acid
Systematic Name:	rel-(3R,4S,5R)-4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
RefMet Name:	3-Phosphoshikimic acid
Synonyms:	[PubChem Synonyms]
Exact Mass:	254.0192 (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:	C7H11O8P
InChIKey:	QYOJSKGCWNAKGW-PBXRRBTRSA-N
LIPID MAPS Category:	Polyketides
LIPID MAPS mainclass:	Phenolic acids
LIPID MAPS subclass:	Phenolic acids
SMILES:	C1C(=C[C@H]([C@H]([C@@H]1O)O)OP(=O)(O)O)C(=O)O
Studies:	Available studies (via RefMet name)

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External database links:

PubChem CID:	121947
CHEBI ID:	17052
HMDB ID:	HMDB0301781

Calculated physicochemical properties (?):

Heavy Atoms:	16
Rings:	1
Aromatic Rings:	0
Rotatable Bonds:	3
van der Waals Molecular volume:	202.17 Å3 molecule-1
Toplogical Polar Sufrace Area:	144.52 Å2 molecule-1
Hydrogen Bond Donors:	5
Hydrogen Bond Acceptors:	8
logP:	-0.20
Molar Refractivity:	50.53
Fraction sp3 Carbons:	0.57
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