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73573-88-3 molecular structure
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(1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate

ChemBase ID: 134162
Molecular Formular: C23H34O5
Molecular Mass: 390.51306
Monoisotopic Mass: 390.24062419
SMILES and InChIs

SMILES:
CC[C@H](C)C(=O)O[C@H]1CCC=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@@H]1C[C@H](CC(=O)O1)O
Canonical SMILES:
CC[C@@H](C(=O)O[C@H]1CCC=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)C
InChI:
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

Cite this record

CBID:134162 http://www.chembase.cn/molecule-134162.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(1S,7S,8S,8aR)-8-{2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl}-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl (2S)-2-methylbutanoate
IUPAC Traditional name
mevastatin
Synonyms
Compactin
ML-236B
Mevastatin
Compactin, 6-Demethylvevinolin, CS-500, ML-236 B
Mevastatin
CAS Number
73573-88-3
MDL Number
MFCD05662341
Beilstein Number
1269441
PubChem SID
162228439
24278540
PubChem CID
64715

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
PubChem 64715 external link

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 14.914537  H Acceptors
H Donor LogD (pH = 5.5) 3.6151679 
LogD (pH = 7.4) 3.6151679  Log P 3.6151679 
Molar Refractivity 108.6338 cm3 Polarizability 42.577927 Å3
Polar Surface Area 72.83 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Acetone expand Show data source
DMSO: soluble20 mg/mL expand Show data source
ethanol: soluble25 mg/mL expand Show data source
Apperance
Off-White Solid expand Show data source
white powder expand Show data source
Melting Point
135-137°C expand Show data source
151-153 °C expand Show data source
Storage Condition
-20°C Freezer expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... HMGCL(3155), HMGCR(3156)rat ... Hmgcr(25675) expand Show data source
Purity
≥95% (HPLC) expand Show data source
≥96% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Empirical Formula (Hill Notation)
C23H34O5 expand Show data source

DETAILS

DETAILS

Sigma Aldrich Sigma Aldrich TRC TRC
Sigma Aldrich - M2537 external link
Biochem/physiol Actions
HMG-CoA reductase inhibitor. Cholesterol lowering drug. Inhibits myoblast formation. An antibiotic shown to cause apoptosis, apparently by inhibiting post-translational prenylation of proteins such as Ras. Similarly, mevastatin increases eNOS mRNA and protein levels by blocking the geranylgeranylation of Rho.
Sigma Aldrich - 27696 external link
Other Notes
Potent inhibitor of 3-hydroxy-3-methylglutaryl-CoA reductase, HMG-CoA reductase1,2,3; Used e.g. in culturing compactin-resistant cell lines overaccumulating HMG-CoA reductase4
Toronto Research Chemicals - M340500 external link
A fungal metabolite which is a potent inhibitor of HMG-CoA reductase.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Endo, A., et al.: FEBS Letters, 72, 323 (1976)
  • • Endo, A.: J. Med. Chem., 28, 401 (1985)
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PATENTS

PATENTS

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INTERNET

INTERNET

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