Basic information
- Standard SMILES
CC[C@H](C)C(=O)O[C@H]1C[C@@H](C)C=C2C=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(=O)O)[C@H]21- InChIKey
QLJODMDSTUBWDW-BXMDZJJMSA-N- Molecular formula
- C24H38O6
- Average molar mass
- 422.6 g/mol
- Monoisotopic mass
- 422.26683894
Overview
Mevinolinic acid is a polyketide obtained by hydrolysis of the pyranone ring of lovastatin. It has a role as an EC 1.1.1.34/EC 1.1.1.88 (hydroxymethylglutaryl-CoA reductase) inhibitor, a drug metabolite, a teratogenic agent and an Aspergillus metabolite. It is a polyketide, a fatty acid ester, a dihydroxy monocarboxylic acid and a carbobicyclic compound. It is functionally related to a (S)-2-methylbutyric acid and a lovastatin. It is a conjugate acid of a mevinolinate.
Names & identifiers
- Preferred name
- Lovastatin Acid
- IUPAC
- (3R,5R)-7-[(1S,2S,6R,8S,8aR)-2,6-dimethyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
- English name
- LOVASTATIN HYDROXY ACID, SODIUM SALT
- Molecular formula
- C24H38O6
- Molecular weight
- 422.55
Names & synonyms
Lovastatin acidMevinolinic acid75225-51-3Monacolinic K acidMSD 803 acidMK 819L-154819MK-819MSD-803 ACID5CLV35Y90C(3R,5R)-7-[(1S,2S,6R,8S,8aR)-2,6-dimethyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid(3R,5R)-7-[(1S,2S,6R,8S,8aR)-2,6-dimethyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
Show more names
mk819MB 530Bl154819msd803acidmsd803freeacidmonacolinickacidLOVASTATIN SODIUMmevinolinicacidammoniumsaltLovastatin-d9 hydroxy sodium6-beta,8-beta(r*),8a-beta))-2-alpha
CHEBI:82985DTXSID20873334lovestatin acid(3R,5R)-7-((1S,2S,6R,8S,8aR)-2,6-dimethyl-8-(((2S)-2-methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)-3,5-dihydroxyheptanoic acid(3R,5R)-7-((1S,2S,6R,8S,8aR)-2,6-dimethyl-8-((2S)-2-methylbutanoyl)oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)-3,5-dihydroxyheptanoic acidRefChem:818793DTXCID70820838L-154,819
Database identifiers
- CAS
75225-51-3- PubChem CID
- 64727
- DTXSID
DTXSID20873334- ChEMBL
CHEMBL1201373- ChEBI
CHEBI:82985- UNII
- 5CLV35Y90C
- Nikkaji
- J399.042G
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 104 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 11
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 654
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 140 · 140 - 143oC
- Boiling point
- 602.3 · 602.3±55.0 °C(Predicted)
- Density
- 1.14 · 1.14±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · Hygroscopic, -20°C Freezer, Under Inert Atmosphere
- solubility
- DMSO (Slightly), Methanol (Slightly, Sonicated), Water (Slightly)
- form
- Solid
- pka
- 4.31 · 4.31±0.10(Predicted)
- color
- Off-White to Light Brown
- Stability
- Very Hygroscopic
- FDA UNII
- 5 CLV35Y90C · 5CLV35Y90C
- Symbol(GHS)
- 8 · GHS08
- Signal word
- Warning
- Hazard statements
- 351 · H351-H361f-H413
- Precautionary statements
- 202 · P202-P273-P280-P308+P313-P405-P501
Safety & regulation
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS08
- Hazard statements
- H351-H361f-H413
- Precautionary statements
- P202-P273-P280-P308+P313-P405-P501
Chemistry & industry
Applications
UsesLovastatin Hydroxy Acid, Sodium Salt (Lovastatin EP Impurity B) is a metabolite of Lovastatin.
Suppliers6 total
BOC Sciences1-631-485-4226; 16314854226 · [email protected]
长沙晶康新材料科技有限公司0733-0731-85118349 18229890050 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
BOC Sciences16314854226 · [email protected]
TargetMol中国（陶术生物）15002134094 · [email protected]
淄博航宇生物科技发展有限公司+86-0533-2185556 +86-15965530500 · [email protected]
Additional notes
DefinitionChEBI: A polyketide obtained by hydrolysis of the pyranone ring of lovastatin.
Related reactions
5 records
Linked notes
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