(1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.0^{5,9}]nonadeca-5(9),6-dien-17-ol

• ChemBase ID: 105682
• Molecular Formular: C20H28O3
• Molecular Mass: 316.43452
• Monoisotopic Mass: 316.20384476
• SMILES: OC[C@@]1(O)C[C@]23[C@H]([C@]4([C@@H](c5ccoc5CC4)CC2)C)CC[C@H]1C3
• 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+/m1/s1
• InChIKey: DNJVYWXIDISQRD-HWUKTEKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,4S,12S,13R,16R,17R)-17-(hydroxymethyl)-12-methyl-8-oxapentacyclo[14.2.1.0^{1,13}.0^{4,12}.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: 162092160
• PubChem CID: 108052

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: 156-158°C

Safety Information

• Storage Condition: 2-8°C

DETAILS

MP Biomedicals - 02193745

From Coffee Beans A natural extract which induces glutathione S-transferase.

REFERENCES

• Lam, L.K.T., et al., Cancer Res., 42 ; 1193-98, (1982).