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Substance Name: Mevastatin [INN]
RN: 73573-88-3
UNII: 1UQM1K0W9X
InChIKey: AJLFOPYRIVGYMJ-INTXDZFKSA-N

Note

  • Antifungal metabolite from Penicillium brevicopactum; potent inhibitory activity to sterol synthesis.

Molecular Formula

  • C23-H34-O5

Molecular Weight

  • 390.517
 

Classification Codes

  • Anti-Bacterial Agents
  • Anti-Infective Agents
  • Antibiotics, Antifungal
  • Anticholesteremic Agents
  • Antifungal Agents
  • Antilipemic Agents
  • Antimetabolites
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Hydroxymethylglutaryl-CoA Reductase Inhibitors
  • Hypolipidemic Agents
  • Lipid Regulating Agents
  • Natural Product
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Names and Synonyms

Name of Substance

  • Mevastatin
  • Mevastatin [INN]

Synonyms

  • (1S,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-7-methyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthyl (S)-2-methylbutyrate
  • Antibiotic ML 236B
  • CCRIS 4505
  • Compactin
  • Compactin (penicillium)
  • CS 500
  • EC 700-442-0
  • Mevastatin
  • Mevastatina
  • Mevastatina [INN-Spanish]
  • Mevastatine
  • Mevastatine [INN-French]
  • Mevastatinum
  • Mevastatinum [INN-Latin]
  • ML 236 B
  • ML-236B
  • UNII-1UQM1K0W9X

Systematic Names

  • (1S,7S,8S,8aR)-1,2,3,7,8,8a-Hexahydro-7-methyl-8-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthyl (S)-2-methylbutyrate
  • (1S,7S,8S,8aR)-8-(2-((2R,4R)-4-Hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl(2S)-2-methylbutanoate
  • 7-(1,2,6,7,8,8a-Hexahydro-2-methyl-8-(2-methylbutyryloxy)naphthyl)-3-hydroxyheptan-5-olide
  • Butanoic acid, 2-methyl-, (1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (2S)-
  • Butanoic acid, 2-methyl-, 1,2,3,7,8,8a-hexahydro-7-methyl-8-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1-naphthalenyl ester, (1S-(1-alpha(R*),7-beta,8-beta(2S*,4S*),8a-beta))-
  • Compactin

Registry Numbers

CAS Registry Number

  • 73573-88-3

FDA UNII

  • 1UQM1K0W9X

Other Registry Numbers

  • 58948-09-7
  • 60478-65-1

System Generated Number

  • 0073573883

Structure Descriptors

InChI

1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1

InChIKey

AJLFOPYRIVGYMJ-INTXDZFKSA-N

Smiles

C1CC=C2C=C[C@@H]([C@@H]([C@@H]2[C@H]1OC(=O)[C@H](CC)C)CC[C@@H]1C[C@H](CC(O1)=O)O)C

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD oral > 2gm/kg (2000mg/kg)   Journal of Antibiotics. Vol. 29, Pg. 1346, 1976.
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   Journal of Antibiotics. Vol. 29, Pg. 1346, 1976.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 152 deg C   EXP
log P (octanol-water) 3.95 (none)   EXP
Water Solubility 4.800 mg/L 25 EST
Vapor Pressure 2.19E-12 mm Hg 25 EST
Henry's Law Constant 1.60E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.28E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.