(1R,6R,8S,9S,10S,11R,12R,13S,16S,17R)-8-tert-butyl-6,9,12,17-tetrahydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.01,11.03,7.07,11.013,17]nonadecane-5,15,18-trione

• ChemBase ID: 156867
• Molecular Formular: C20H24O11
• Molecular Mass: 440.39796
• Monoisotopic Mass: 440.13186159
• SMILES: C[C@@H]1C(=O)O[C@@H]2[C@]1([C@@]13C(=O)O[C@H]4[C@]1([C@H]2O)C1([C@@H]([C@@H]4O)C(C)(C)C)[C@H](C(=O)OC1O3)O)O
• Canonical SMILES: O=C1O[C@@H]2[C@@]([C@@H]1C)(O)[C@@]13[C@]4([C@H]2O)[C@H](OC3=O)[C@H]([C@H](C24C(O1)OC(=O)[C@@H]2O)C(C)(C)C)O
• InChI: InChI=1S/C20H24O11/c1-5-12(24)28-11-8(22)18-10-6(21)7(16(2,3)4)17(18)9(23)13(25)30-15(17)31-20(18,14(26)29-10)19(5,11)27/h5-11,15,21-23,27H,1-4H3/t5-,6+,7+,8+,9+,10-,11+,15?,17?,18-,19-,20-/m1/s1
• InChIKey: AMOGMTLMADGEOQ-CFTQXCTRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,6R,8S,9S,10S,11R,12R,13S,16S,17R)-8-tert-butyl-6,9,12,17-tetrahydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0^1,^1^1.0^3,^7.0^7,^1^1.0^1^3,^1^7]nonadecane-5,15,18-trione
• IUPAC Traditional name: (1R,6R,8S,9S,10S,11R,12R,13S,16S,17R)-8-tert-butyl-6,9,12,17-tetrahydroxy-16-methyl-2,4,14,19-tetraoxahexacyclo[8.7.2.0^1,^1^1.0^3,^7.0^7,^1^1.0^1^3,^1^7]nonadecane-5,15,18-trione
• Synonyms: 1,7-Dihydroxy-ginkgolide A; Ginkgolide C; 白果苦内酯 C; 银杏内酯 C

Database IDs

• CAS Number: 15291-76-6
• MDL Number: MFCD02094178
• PubChem SID: 162251004; 24851032
• PubChem CID: 16211418

CALCULATED PROPERTIES

• Acid pKa: 11.704632
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.5791627
• LogD (pH = 7.4): -1.5791839
• Log P: -1.5791625
• Molar Refractivity: 92.6665 cm^3
• Polarizability: 39.107513 Å^3
• Polar Surface Area: 169.05 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥96.0% (HPLC)
• Grade: analytical standard
• Empirical Formula (Hill Notation): C20H24O11

DETAILS

Sigma Aldrich - 18309

Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references