(1S,4S,12S,13R,16S,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.01,13.04,12.05,9]nonadeca-5(9),6-dien-17-ol

• ChemBase ID: 126323
• Molecular Formular: C20H28O3
• Molecular Mass: 316.43452
• Monoisotopic Mass: 316.20384476
• SMILES: OC[C@@]1(O)C[C@]23C[C@H]1CC[C@H]2[C@]1(C)CCc2occc2[C@H]1CC3
• Canonical SMILES: OC[C@@]1(O)C[C@@]23C[C@H]1CC[C@H]3[C@]1([C@H](CC2)c2ccoc2CC1)C
• InChI: InChI=1S/C20H28O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h6,9,13,15,17,21-22H,2-5,7-8,10-12H2,1H3/t13-,15+,17-,18+,19-,20-/m0/s1
• InChIKey: DNJVYWXIDISQRD-JTSSGKSMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,12S,13R,16S,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0^1,^1^3.0^4,^1^2.0^5,^9]nonadeca-5(9),6-dien-17-ol
• IUPAC Traditional name: cafestol
• Synonyms: Cafestol

Database IDs

• CAS Number: 469-83-0
• PubChem SID: 162220661
• PubChem CID: 108052; 10018664
• Chemspider ID: 10289419
• KEGG ID: C09066
• Unique Ingredient Identifier: AC465T6Q6W
• Wikipedia Title: Cafestol

CALCULATED PROPERTIES

• Acid pKa: 13.685427
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.6770277
• LogD (pH = 7.4): 2.6770275
• Log P: 2.6770277
• Molar Refractivity: 88.5501 cm^3
• Polarizability: 34.82681 Å^3
• Polar Surface Area: 53.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 158-162 °C (316.4-323.6°F)

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Legal everywhere