(3R,6R,8S,10R,13S,16S,17R)-8-tert-butyl-6,17-dihydroxy-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: 130709
• Molecular Formular: C20H24O9
• Molecular Mass: 408.39916
• Monoisotopic Mass: 408.14203235
• SMILES: C[C@@H]1C(=O)O[C@@H]2[C@]1(C13C(=O)O[C@H]4C1(C2)C1([C@@H](C4)C(C)(C)C)[C@H](C(=O)O[C@H]1O3)O)O
• Canonical SMILES: O=C1O[C@@H]2[C@@]([C@@H]1C)(O)C13C4(C2)[C@H](OC3=O)C[C@H](C24[C@H](O1)OC(=O)[C@@H]2O)C(C)(C)C
• InChI: InChI=1S/C20H24O9/c1-7-12(22)26-10-6-17-9-5-8(16(2,3)4)18(17)11(21)13(23)28-15(18)29-20(17,14(24)27-9)19(7,10)25/h7-11,15,21,25H,5-6H2,1-4H3/t7-,8+,9-,10+,11+,15+,17?,18?,19-,20?/m1/s1
• InChIKey: FPUXKXIZEIDQKW-ZJZLDMJOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,6R,8S,10R,13S,16S,17R)-8-tert-butyl-6,17-dihydroxy-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: (3R,6R,8S,10R,13S,16S,17R)-8-tert-butyl-6,17-dihydroxy-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: Ginkgolide A from Ginkgo biloba leaves; Ginkgolide A; 银杏内酯 A 来源于银杏 叶; 银杏内酯 A

Database IDs

• CAS Number: 15291-75-5
• MDL Number: MFCD00133365
• PubChem SID: 162224987; 24895144; 24874033
• PubChem CID: 6419993

CALCULATED PROPERTIES

• Acid pKa: 11.767949
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.33678335
• LogD (pH = 7.4): 0.336765
• Log P: 0.3367836
• Molar Refractivity: 90.1745 cm^3
• Polarizability: 37.710293 Å^3
• Polar Surface Area: 128.59 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: ≥90% (HPLC); ≥98.0% (HPLC)
• Grade: analytical standard; primary reference standard
• Empirical Formula (Hill Notation): C20H24O9

DETAILS

Sigma Aldrich - 51863

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

Sigma Aldrich - 00770590

Application
Reference standard in the analysis of herbal medicinal products
General description
Produced and qualified by HWI AnalytikExact content by quantitative NMR can be found on the certificate

Sigma Aldrich - G4028

Biochem/physiol Actions
Constituent of Ginkgo biloba extracts. Antioxidant.
Protocols & Applications
Ginkgo (Ginkgo biloba) Plant Profile: bioactives, mechanism of action, references