ContaminantDB: (R)-Mevalonic acid-5-pyrophosphate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-26 05:38:30 UTC

Update Date

2016-11-09 01:21:17 UTC

Accession Number

CHEM035295

Identification

Common Name

(R)-Mevalonic acid-5-pyrophosphate

Class

Small Molecule

Description

Contaminant Sources

FooDB Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-Mevalonate-5-pyrophosphate	Generator
(R)-Mevalonic acid-5-pyrophosphoric acid	Generator
(R)-5-Diphosphomevalonic acid	HMDB
1,1,3,7-Tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-Oate	HMDB
1,1,3,7-Tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-Oic acid	HMDB
1,1,3,7-Tetrahydroxy-7-methyl-2,4-dioxa-1,3-diphosphanonan-9-Oic acid 1,3-dioxide	HMDB
5-Pyrophosphomevalonate	HMDB
5-Pyrophosphomevalonic acid	HMDB
Mevalonate 5-diphosphate	HMDB
Mevalonic 5-pyrophosphate	HMDB
Mevalonic acid 5-diphosphate	HMDB
Mevalonic acid 5-pyrophosphate	HMDB
Mevalonic acid pyrophosphate	HMDB
MVADP	HMDB
Pyrophosphomevalonate	HMDB
Pyrophosphomevalonic acid	HMDB
R-Mevalonic acid-5-pyrophosphate	HMDB
Mevalonate pyrophosphate	MeSH, HMDB
5-Diphosphomevalonic acid	MeSH, HMDB
(3S)-3-Hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoate	Generator, HMDB

Chemical Formula

C₆H₁₄O₁₀P₂

Average Molecular Mass

308.117 g/mol

Monoisotopic Mass

308.006 g/mol

CAS Registry Number

1492-08-6

IUPAC Name

(3S)-3-hydroxy-5-{[hydroxy(phosphonooxy)phosphoryl]oxy}-3-methylpentanoic acid

Traditional Name

pyrophosphomevalonate

SMILES

C[C@](O)(CCOP(O)(=O)OP(O)(O)=O)CC(O)=O

InChI Identifier

InChI=1S/C6H14O10P2/c1-6(9,4-5(7)8)2-3-15-18(13,14)16-17(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H,13,14)(H2,10,11,12)/t6-/m0/s1

InChI Key

SIGQQUBJQXSAMW-LURJTMIESA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as organic pyrophosphates. These are organic compounds containing the pyrophosphate oxoanion, with the structure OP([O-])(=O)OP(O)([O-])=O.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organic oxoanionic compounds

Sub Class

Organic pyrophosphates

Direct Parent

Organic pyrophosphates

Alternative Parents

Substituents

Organic pyrophosphate
Monoalkyl phosphate
Short-chain hydroxy acid
Organic phosphoric acid derivative
Fatty acid
Alkyl phosphate
Phosphoric acid ester
Tertiary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	8.26 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-1.6	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	1.78	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	170.82 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	56.26 m³·mol⁻¹	ChemAxon
Polarizability	23.59 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004m-9820000000-20a5a060549dcb7bd8d3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-00dv-9243200000-6d8177d69adb810da37f	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-000i-0090000000-27d85eaaa9c4e19f0fcf	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-000i-0090000000-8e9a7018cd2663189521	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-002r-3490000000-b2f4bcb965dfbe91ce8f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, negative	splash10-004r-7690000000-533cfa9b6449fe59e31d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, negative	splash10-004i-9540000000-ba3a429bcc345a49d5ff	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 15V, negative	splash10-004i-9310000000-b552a514df86bf203483	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 18V, negative	splash10-004i-9200000000-73f02610e11b09ea0ae0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 20V, negative	splash10-004i-9100000000-e99ccf8685bbb8c58b7f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 25V, negative	splash10-004i-9000000000-df1600382f0903920e95	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, negative	splash10-004i-1900000000-0d135499da95ac5499d5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, negative	splash10-0a4i-0900000000-b559d4679fc0eaa79be7	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, negative	splash10-004i-9000000000-46d4cee1b5ac630ba9b8	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, negative	splash10-004i-1590000000-bd14b17224627a5d2418	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, negative	splash10-0a4i-0900000000-dc954ce23ecf1a263189	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, negative	splash10-0kdi-0490000000-356afce14b98128806e5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0a4i-0009000000-ece59023c1177bedb2f3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, negative	splash10-0a4i-0009000000-cbc9841391b1e5bea83c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-0a4i-1109000000-71626d1a601d118a3d29	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 11V, negative	splash10-0a6r-9516000000-b1e714407672ea74b65f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, negative	splash10-004i-9300000000-79a6a45a050a4557acba	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 17V, negative	splash10-004i-9100000000-53b8fc8a95948a4c9764	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 20V, negative	splash10-004i-9100000000-0afb1187a03463994c7a	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 24V, negative	splash10-004i-9000000000-92672b421a976d0722e3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 28V, negative	splash10-004i-9000000000-ad774759f01ecd022463	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 33V, negative	splash10-004i-9000000000-028cfb3af846dc9c0ee5	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0001981

FooDB ID

FDB022779

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

6415

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

17216150

ChEBI ID

Not Available

PubChem Compound ID

22833574

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. Bloch, Konrad; Chaykin, S.; Phillips, A. H.; De Waard, A. Mevalonic acid pyrophosphate and isopentylpyrophosphate. Journal of Biological Chemistry (1959), 234 2595-2604.

2. Ku EC: Regulation of fatty acid biosynthesis by intermediates of the cholesterol biosynthetic pathway. Biochem Biophys Res Commun. 1996 Aug 5;225(1):173-9.

3. Cuthbert JA, Lipsky PE: Inhibition by 6-fluoromevalonate demonstrates that mevalonate or one of the mevalonate phosphates is necessary for lymphocyte proliferation. J Biol Chem. 1990 Oct 25;265(30):18568-75.

(R)-Mevalonic acid-5-pyrophosphate (CHEM035295)

Structure for CHEM035295: (R)-Mevalonic acid-5-pyrophosphate