MEVALONIC ACID

Details

Stereochemistry	RACEMIC
Molecular Formula	C6H12O4
Molecular Weight	148.1571
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)(CCO)CC(O)=O

InChI

InChIKey=KJTLQQUUPVSXIM-UHFFFAOYSA-N

InChI=1S/C6H12O4/c1-6(10,2-3-7)4-5(8)9/h7,10H,2-4H2,1H3,(H,8,9)

HIDE SMILES / InChI

Approval Year

PubMed

Title	Date	PubMed
Identification of a gene cluster for the mevalonate pathway in Lactobacillus helveticus.	2001	11762194
In vivo prenylation analysis of Ras and Rho proteins.	2001	11305090
Isoprene increases thermotolerance of fosmidomycin-fed leaves.	2001 Apr	11299379
Key regulatory oxysterols in liver: analysis as delta4-3-ketone derivatives by HPLC and response to physiological perturbations.	2001 Apr	11290837
Synthetic applications of epoxide hydrolases.	2001 Apr	11282336
In vivo anti-inflammatory effect of statins is mediated by nonsterol mevalonate products.	2001 Aug	11498461
Diurnal rhythm of cholesterol biosynthesis in experimental chronic renal failure.	2001 Dec	11855739
Statins and their potential for osteoporosis.	2001 Dec	11728917
Nitrogen-bisphosphonates block retinoblastoma phosphorylation and cell growth by inhibiting the cholesterol biosynthetic pathway in a keratinocyte model for esophageal irritation.	2001 Feb	11160853
Simvastatin inhibits noradrenaline-induced hypertrophy of cultured neonatal rat cardiomyocytes.	2001 Jan	11156573
Suppression of dolichol synthesis with isoprenoids and statins may potentiate the cancer-retardant efficacy of IGF-I down-regulation.	2001 Jan	11133248
Structure of 4-diphosphocytidyl-2-C- methylerythritol synthetase involved in mevalonate- independent isoprenoid biosynthesis.	2001 Jul	11427897
Biosynthesis of 2-methyl-3-buten-2-ol emitted from needles of Pinus ponderosa via the non-mevalonate DOXP/MEP pathway of isoprenoid formation.	2001 Jun	11469599
Statins suppress THP-1 cell migration and secretion of matrix metalloproteinase 9 by inhibiting geranylgeranylation.	2001 Jun	11404382
HMG-CoA reductase inhibitors prevent migration of human coronary smooth muscle cells through suppression of increase in oxidative stress.	2001 Jun	11397700
A new HMG-CoA reductase inhibitor, rosuvastatin, exerts anti-inflammatory effects on the microvascular endothelium: the role of mevalonic acid.	2001 Jun	11375257
Dose-dependent effects of lovastatin on cell cycle progression. Distinct requirement of cholesterol and non-sterol mevalonate derivatives.	2001 Jun 29	11470239
The in vitro inhibitory effect of tannin derivatives on 3-hydroxy-3-methylglutaryl-coenzyme a reductase on vero cells.	2001 May	11359999
NK-104, a 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor, reduces osteopontin expression by rat aortic smooth muscle cells.	2001 May	11325797
Lovastatin controls signal transduction in vascular smooth muscle cells by modulating phosphorylation levels of mevalonate-independent pathways.	2001 May-Jun	11403422
Inhibition of isoprenoid biosynthesis causes insulin resistance in 3T3-L1 adipocytes.	2001 Nov 2	11696371
Blocking protein geranylgeranylation is essential for lovastatin-induced apoptosis of human acute myeloid leukemia cells.	2001 Sep	11516100
The genetics and molecular genetics of terpene and sterol origami.	2002 Apr	11856612
Incorporation of [1-(13)C]1-deoxy-D-xylulose into isoprenoids of the liverwort Conocephalum conicum.	2002 Feb	11830134
Increased nitric oxide bioavailability in endothelial cells contributes to the pleiotropic effect of cerivastatin.	2002 Feb 26	11864921
Biosynthesis of zeaxanthin via mevalonate in Paracoccus species strain PTA-3335. A product-based retrobiosynthetic study.	2002 Feb 8	11856031
Consequences of mevalonate depletion. Differential transcriptional, translational, and post-translational up-regulation of Ras, Rap1a, RhoA, AND RhoB.	2002 Mar 22	11788600

Patents

Name

Type

Language

MEVALONIC ACID

Systematic Name

English

PENTANOIC ACID, 3,5-DIHYDROXY-3-METHYL-

Common Name

English

DL-MEVALONIC ACID

Common Name

English

(3RS)-MEVALONIC ACID

Systematic Name

English

MEVALONIC ACID [MI]

Common Name

English

HIOCHIC ACID

Common Name

English

Mevalonic acid [WHO-DD]

Common Name

English

MEVALONIC ACID [HSDB]

Common Name

English

(±)-MEVALONIC ACID

Systematic Name

English

Code System Code Type Description

CAS

150-97-0