sodium (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate

• ChemBase ID: 154487
• Molecular Formular: C23H35NaO7
• Molecular Mass: 446.50957
• Monoisotopic Mass: 446.22804774
• SMILES: CC[C@H](C)C(=O)O[C@H]1C[C@@H](C=C2[C@H]1[C@H]([C@H](C=C2)C)CC[C@H](C[C@H](CC(=O)[O-])O)O)O.[Na+]
• Canonical SMILES: CC[C@@H](C(=O)O[C@H]1C[C@H](O)C=C2[C@H]1[C@@H](CC[C@H](C[C@H](CC(=O)[O-])O)O)[C@H](C=C2)C)C.[Na+]
• InChI: InChI=1S/C23H36O7.Na/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28;/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28);/q;+1/p-1/t13-,14-,16+,17+,18+,19-,20-,22-;/m0./s1
• InChIKey: VWBQYTRBTXKKOG-IYNICTALSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• IUPAC Traditional name: sodium pravastatin(1-); sodium (3R,5R)-7-[(1S,2S,6S,8S,8aR)-6-hydroxy-2-methyl-8-{[(2S)-2-methylbutanoyl]oxy}-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate
• Synonyms: (βR, δR,1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-β, δ,6-trihydroxy-2-methyl-8[(2S)-2-methyl-1-oxobutoxyl]-1-naphthaleneheptanoic acid sodium hydrate; Eptastatin sodium salt hydrate; Pravastatin sodium salt hydrate; (βR,δR,1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-β,δ,6-trihydroxy-2-methyl-8-[(2S)-2-methyl-1-oxobutoxy]-1-naphthaleneheptanoic Acid Sodium Salt; Elisor; Kopostat; Mevalotin; Pravachol; Pravaselect; Pravastatin Sodium; Pravastatin Sodium

Database IDs

• CAS Number: 81131-70-6; 81131-70-6(anhydrous)
• MDL Number: MFCD00887601
• PubChem SID: 162248626
• PubChem CID: 16759173

CALCULATED PROPERTIES

• Acid pKa: 4.212299
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.34003893
• LogD (pH = 7.4): -1.3779589
• Log P: 1.6470916
• Molar Refractivity: 124.435 cm^3
• Polarizability: 44.225346 Å^3
• Polar Surface Area: 127.12 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL; Methanol; Water
• Apperance: White Crystalline Powder; white powder
• Melting Point: 149-150°C; 171.2-173 °C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: QJ7185000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: HMG CoA reductase inhibitor

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Na+
• Biological Source: Isol. from Absidia coerulea
• Application(s): Antihypercholesterolaemic agent; Increases receptor-mediated catabolism of low density lipoprotein
• Empirical Formula (Hill Notation): C23H35O7Na · xH2O

DETAILS

Sigma Aldrich - P4498

Biochem/physiol Actions
Competitive, water-soluble 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) reductase inhibitor. Inhibits cholesterol synthesis in vivo (Ki ~1 nM).

Toronto Research Chemicals - P702000

A competitive inhibitor of HMG-CoA reductase. Bioactive metabolite of Mevastatin.

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