Metabolomics Structure Database

MDLMOL SDF CSV TSV

MW REGNO:	37961
Common Name:	(S)-Mevalonic acid-5-pyrophosphate
Systematic Name:	(3S)-3-hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoic acid
Synonyms:	[PubChem Synonyms]
Exact Mass:	308.0062 (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:	C6H14O10P2
InChIKey:	SIGQQUBJQXSAMW-LURJTMIESA-N
ClassyFire superclass:	Organic oxygen compounds
ClassyFire class:	Organic oxoanionic compounds
ClassyFire subclass:	Organic pyrophosphates
ClassyFire direct parent:	Organic pyrophosphates
SMILES:	C[C@](CCOP(=O)(O)OP(=O)(O)O)(CC(=O)O)O
Studies:	Available studies(via PubChem CID)

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External database links:

PubChem CID:	22833574
HMDB ID:	HMDB0001981
Chemspider ID:	17216150
METLIN ID:	6415

Calculated physicochemical properties (?):

Heavy Atoms:	18
Rings:	0
Aromatic Rings:	0
Rotatable Bonds:	8
van der Waals Molecular volume:	237.28 Å3 molecule-1
Toplogical Polar Sufrace Area:	170.82 Å2 molecule-1
Hydrogen Bond Donors:	5
Hydrogen Bond Acceptors:	10
logP:	0.91
Molar Refractivity:	56.99
Fraction sp3 Carbons:	0.83
sp3 Carbons:	5

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
NPClassifier classification: "NPClassifier: A Deep Neural Network-Based Structural Classification Tool for Natural Products", Kim HW, Wang M, Leber CA, Nothias LF, Reher R, Kang KB, van der Hooft JJJ, Dorrestein PC, Gerwick WH and Cottrell GW. J Nat Prod. 2021 Nov 26;84(11):2795-2807.DOI: 10.1021/acs.jnatprod.1c00399.