Common Name(r)-5-phosphomevalonate
DescriptionMevalonic acid-5P (CAS: 1189-94-2), also known as 5-phosphomevalonic acid, belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Within humans, mevalonic acid-5P participates in many enzymatic reactions. In particular, mevalonic acid-5P can be biosynthesized from mevalonate; which is mediated by the enzyme mevalonate kinase. In addition, mevalonic acid-5P can be converted into mevalonic acid-5-pyrophosphate through its interaction with the enzyme phosphomevalonate kinase. In humans, mevalonic acid-5P is involved in the mevalonate pathway. Outside of the human body, mevalonic acid-5P has been detected, but not quantified in, several different foods, such as oriental wheat, devilfish, pepper (spice), redcurrants, and star fruits. This could make mevalonic acid-5P a potential biomarker for the consumption of these foods.
Structure
Molecular FormulaC6H13O7P
Average Mass228.13700
Monoisotopic Mass228.03989
IUPAC Name(3R)-3-hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid
Traditional Name(3r)-3-hydroxy-3-methyl-5-(phosphonooxy)pentanoic acid
CAS Registry Number73566-35-5
SMILESC[C@@](O)(CCOP(=O)([O-])[O-])CC(=O)[O-]
InChI IdentifierInChI=1S/C6H13O7P/c1-6(9,4-5(7)8)2-3-13-14(10,11)12/h9H,2-4H2,1H3,(H,7,8)(H2,10,11,12)/t6-/m1/s1
InChI KeyOKZYCXHTTZZYSK-ZCFIWIBFSA-N
CHEBI IDCHEBI:58146
HMDB IDHMDB0001343
Pathways
NameSMPDB/PathBank
Steroid Biosynthesis
Ibandronate Action Pathway
Simvastatin Action Pathway
Pravastatin Action Pathway
Rosuvastatin Action Pathway
Alendronate Action Pathway
Lovastatin Action Pathway
Zoledronate Action Pathway
Cerivastatin Action Pathway
Risedronate Action Pathway
Pamidronate Action Pathway
Fluvastatin Action Pathway
Atorvastatin Action Pathway
Hypercholesterolemia
Lysosomal Acid Lipase Deficiency (Wolman Disease)
Desmosterolosis
CHILD Syndrome
Chondrodysplasia Punctata II, X Linked Dominant (CDPX2)
Smith-Lemli-Opitz Syndrome (SLOS)
Cholesteryl ester storage disease
Hyper-IgD syndrome
Mevalonic aciduria
Wolman disease
StateSolid
Water Solubility1.99e+01 g/l
logP-2.18
logS-1.06
pKa (Strongest Acidic)1.71
pKa (Strongest Basic)-2.92
Hydrogen Acceptor Count6
Hydrogen Donor Count4
Polar Surface Area124.29 Ų
Rotatable Bond Count6
Physiological Charge-3
Formal Charge0
Refractivity45.38 m³·mol⁻¹
Polarizability19.23

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