ChemFOnt: Showing chemical card for (R)-5-Diphosphomevalonic acid (CFc000000857)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:22 UTC

Chemfont ID

CFc000000857

Molecule Identification

Common Name

(R)-5-Diphosphomevalonic acid

Definition

508

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-5-Diphosphomevalonate	ChEBI
5-Diphosphomevalonate	HMDB
5-Diphosphomevalonic acid	HMDB
Mevalonate 5-diphosphate	HMDB
Mevalonate pyrophosphate	HMDB
Mevalonate-diphosphate	HMDB
(3R)-3-Hydroxy-5-[[hydroxy(phosphonooxy)phosphinyl]oxy]-3-methylpentanoic acid	HMDB
(R)-Diphosphomevalonic acid	HMDB
5-Pyrophosphomevalonic acid	HMDB
Mevalonic 5-pyrophosphate	HMDB
Mevalonic acid 5-diphosphate	HMDB
Mevalonic acid 5-pyrophosphate	HMDB
Mevalonic acid pyrophosphate	HMDB
Pyrophosphomevalonic acid	HMDB
(3R)-3-Hydroxy-5-[[hydroxy(phosphonooxy)phosphinyl]oxy]-3-methylpentanoate	HMDB
(R)-Diphosphomevalonate	HMDB
5-Pyrophosphomevalonate	HMDB
Mevalonate 5-pyrophosphate	HMDB
Mevalonic 5-pyrophosphic acid	HMDB
Mevalonic acid 5-diphosphic acid	HMDB
Mevalonic acid 5-pyrophosphic acid	HMDB
Mevalonic acid pyrophosphic acid	HMDB
Pyrophosphomevalonate	HMDB
(R)-5-Diphosphomevalonic acid	Generator
R-Diphosphomevalonate	HMDB

Chemical Formula

C₆H₁₄O₁₀P₂

Average Molecular Weight

308.1169

Monoisotopic Molecular Weight

308.006219692

IUPAC Name

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

Traditional Name

mevalonate-diphosphate

CAS Registry Number

103025-21-4

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-/m1/s1

InChI Key

SIGQQUBJQXSAMW-ZCFIWIBFSA-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

carboxyalkyl phosphate (CHEBI:15899 )
Hydroxy fatty acids (LMFA01050416 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Organelle

Peroxisome (HMDB: HMDB0001090)

Source

Endogenous

Endogenous (HMDB: HMDB0001090)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Smith-Lemli-Opitz Syndrome (SLOS) (PathBank: SMP0120515)
Desmosterolosis (PathBank: SMP0120692)
Mevalonic Aciduria (PathBank: SMP0120794)
Lysosomal Acid Lipase Deficiency (Wolman Disease) (PathBank: SMP0120512)
Cholesteryl Ester Storage Disease (PathBank: SMP0120573)
CHILD Syndrome (PathBank: SMP0120464)
Wolman Disease (PathBank: SMP0120576)
Chondrodysplasia Punctata II, X-Linked Dominant (CDPX2) (PathBank: SMP0120685)
Hypercholesterolemia (PathBank: SMP0120769)
Hyper-IgD Syndrome (PathBank: SMP0120574)

Metabolic pathway

Steroid Biosynthesis (PathBank: SMP0087326)
Steroid Biosynthesis (PathBank: SMP0002381)
Terpenoid Backbone Biosynthesis (PathBank: SMP0002384)
Cholesterol Biosynthesis and Metabolism CE(14:0) (PathBank: SMP0002435)
Cholesterol Biosynthesis and Metabolism CE(10:0) (PathBank: SMP0002436)
Cholesterol Biosynthesis and Metabolism CE(12:0) (PathBank: SMP0002438)
Cholesterol Biosynthesis and Metabolism CE(16:0) (PathBank: SMP0002440)
Cholesterol Biosynthesis and Metabolism CE(18:0) (PathBank: SMP0002441)
Cholesterol Biosynthesis and Metabolism (PathBank: SMP0070041)

Drug action pathway

Atorvastatin Action Pathway (PathBank: SMP0000131)
Ibandronate Action Pathway (PathBank: SMP0000079)
Simvastatin Action Pathway (PathBank: SMP0000082)
Pravastatin Action Pathway (PathBank: SMP0000089)
Rosuvastatin Action Pathway (PathBank: SMP0000092)
Alendronate Action Pathway (PathBank: SMP0000095)
Lovastatin Action Pathway (PathBank: SMP0000099)
Zoledronate Action Pathway (PathBank: SMP0000107)
Cerivastatin Action Pathway (PathBank: SMP0000111)
Risedronate Action Pathway (PathBank: SMP0000112)
Pamidronate Action Pathway (PathBank: SMP0000117)
Fluvastatin Action Pathway (PathBank: SMP0000119)

Role

Not Available

Physical Properties

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	23.46 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon