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

Molecular Formula	C6H12O4
Molecular Weight	148.1571
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Approval Year

PubMed

Title	Date	PubMed
The genetics and molecular genetics of terpene and sterol origami.	2002-04	11856612
Consequences of mevalonate depletion. Differential transcriptional, translational, and post-translational up-regulation of Ras, Rap1a, RhoA, AND RhoB.	2002-03-22	11788600
Structure and mechanism of 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase. An enzyme in the mevalonate-independent isoprenoid biosynthetic pathway.	2002-03-08	11786530
Increased nitric oxide bioavailability in endothelial cells contributes to the pleiotropic effect of cerivastatin.	2002-02-26	11864921
Biosynthesis of zeaxanthin via mevalonate in Paracoccus species strain PTA-3335. A product-based retrobiosynthetic study.	2002-02-08	11856031
Structure of 2C-methyl-d-erythritol-2,4-cyclodiphosphate synthase involved in mevalonate-independent biosynthesis of isoprenoids.	2002-02-08	11829504
Incorporation of [1-(13)C]1-deoxy-D-xylulose into isoprenoids of the liverwort Conocephalum conicum.	2002-02	11830134
Carbamazepine increases atherogenic lipoproteins: mechanism of action in male adults.	2002-02	11788421
Kinetic properties and inhibition of Trypanosoma cruzi 3-hydroxy-3-methylglutaryl CoA reductase.	2002-01-16	11801242
Fibrate and statin synergistically increase the transcriptional activities of PPARalpha/RXRalpha and decrease the transactivation of NFkappaB.	2002-01-11	11779144
Genes for mevalonate biosynthesis in Phycomyces.	2002-01	11810250
Biosynthesis of anthraquinones in cell cultures of Cinchona 'Robusta' proceeds via the methylerythritol 4-phosphate pathway.	2002-01	11754943
Dual mechanisms of ABCA1 regulation by geranylgeranyl pyrophosphate.	2001-12-28	11641412
Effect of S(-) perillic acid on protein prenylation and arterial smooth muscle cell proliferation.	2001-12-15	11755117
Modulation of COX-2 expression by statins in human aortic smooth muscle cells. Involvement of geranylgeranylated proteins.	2001-12-14	11591701
Diverse effects of inhibition of 3-hydroxy-3-methylglutaryl-CoA reductase on the expression of VCAM-1 and E-selectin in endothelial cells.	2001-12-01	11716764
Diurnal rhythm of cholesterol biosynthesis in experimental chronic renal failure.	2001-12	11855739
Downregulation of angiotensin II type 1 receptor by hydrophobic 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitors in vascular smooth muscle cells.	2001-12	11742861
Studies on the nonmevalonate pathway of terpene biosynthesis. The role of 2C-methyl-D-erythritol 2,4-cyclodiphosphate in plants.	2001-12	11733027
Biosynthesis of a hopane triterpene and three diterpenes in the liverwort Fossombronia alaskana.	2001-12	11730868
Statins and their potential for osteoporosis.	2001-12	11728917
More on pamidronate in Langerhans'-cell histiocytosis.	2001-11-15	11794213
Inhibition of isoprenoid biosynthesis causes insulin resistance in 3T3-L1 adipocytes.	2001-11-02	11696371
Characterization of hydrophobic prenyl groups of isoprenylated proteins in human cancer cells.	2001-11-02	11676505
Lovastatin increases nitric oxide synthesis in IL-1 beta-stimulated smooth muscle cells.	2001-11	11729502
Genetic disorders of cholesterol biosynthesis in mice and humans.	2001-10-11	11592808
Biosynthetic pathway of insect juvenile hormone III in cell suspension cultures of the sedge Cyperus iria.	2001-10	11598232
Nitrogen-containing bisphosphonates induce apoptosis of Caco-2 cells in vitro by inhibiting the mevalonate pathway: a model of bisphosphonate-induced gastrointestinal toxicity.	2001-10	11595616
The non-mevalonate pathway of isoprenoids: genes, enzymes and intermediates.	2001-10	11578926
Lipophilic statins can be osteogenic by promoting osteoblastic calcification in a Cbfa1- and BMP-2-independent manner.	2001-09	11771853
Geranylgeraniol, an intermediate product in mevalonate pathway, induces apoptotic cell death in human hepatoma cells: death receptor-independent activation of caspase-8 with down-regulation of Bcl-xL expression.	2001-09	11572758
Isoprenoid biosynthesis. Metabolite profiling of peppermint oil gland secretory cells and application to herbicide target analysis.	2001-09	11553758
Blocking protein geranylgeranylation is essential for lovastatin-induced apoptosis of human acute myeloid leukemia cells.	2001-09	11516100
Induction of apoptosis and inhibition of migration of inflammatory and vascular wall cells by cerivastatin.	2001-09	11500171
Determination of mevalonic acid in human urine as mevalonic acid lactone by gas chromatography-mass spectrometry.	2001-08-25	11522061
Statins and bone: myth or reality?	2001-08	11683424
In vivo anti-inflammatory effect of statins is mediated by nonsterol mevalonate products.	2001-08	11498461
Rho-dependent inhibition of the induction of connective tissue growth factor (CTGF) by HMG CoA reductase inhibitors (statins).	2001-08	11487529
Increased urinary leukotriene E(4) during febrile attacks in the hyperimmunoglobulinaemia D and periodic fever syndrome.	2001-08	11466192
Cloning of a gene cluster encoding enzymes responsible for the mevalonate pathway from a terpenoid-antibiotic-producing Streptomyces strain.	2001-07	11515548
Dose-dependent effects of lovastatin on cell cycle progression. Distinct requirement of cholesterol and non-sterol mevalonate derivatives.	2001-06-29	11470239
Inherited disorders of cholesterol biosynthesis.	2001-06	11521206
Mevalonic aciduria and hyper-IgD syndrome: two sides of the same coin?	2001-06	11486910
Mevalonate kinase deficiency in a child with periodic fever and without hyperimmunoglobulinaemia D.	2001-06	11486909
Biosynthesis of 2-methyl-3-buten-2-ol emitted from needles of Pinus ponderosa via the non-mevalonate DOXP/MEP pathway of isoprenoid formation.	2001-06	11469599
Inhibition of human breast cancer cell growth by blockade of the mevalonate-protein prenylation pathway is not prevented by overexpression of cyclin D1.	2001-05	11518463
Catabolic and anabolic signals in bone: therapeutic implications.	2001-05	11517351
Labeling patterns of chloroplastidic isoprenoids in cultured cells of liverwort Ptychanthus striatus.	2001-05	11440120
Incadronate and etidronate accelerate phosphate-primed mineralization of MC4 cells via ERK1/2-Cbfa1 signaling pathway in a Ras-independent manner: further involvement of mevalonate-pathway blockade for incadronate.	2001-05	11430477
Identification of a gene cluster for the mevalonate pathway in Lactobacillus helveticus.	2001	11762194

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:39:43 GMT 2025` Edited by `admin` on `Mon Mar 31 21:39:43 GMT 2025`
Record UNII	S5UOB36OCZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DL-MEVALONIC ACID

Preferred Name

English

MEVALONIC ACID

Systematic Name

English

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

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