(1R,2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadec-9-en-5-ol

• ChemBase ID: 177878
• Molecular Formular: C28H46O
• Molecular Mass: 398.66424
• Monoisotopic Mass: 398.35486609
• SMILES: C1[C@@H](CC2[C@](C1)([C@@H]1C(=CC2)[C@H]2[C@](CC1)([C@H](CC2)[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(C1)CC=C1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2[C@@H](/C=C/[C@@H](C(C)C)C)C)C)C
• InChI: InChI=1S/C28H46O/c1-18(2)19(3)7-8-20(4)24-11-12-25-23-10-9-21-17-22(29)13-15-27(21,5)26(23)14-16-28(24,25)6/h7-8,10,18-22,24-26,29H,9,11-17H2,1-6H3/b8-7+/t19-,20+,21?,22-,24+,25-,26-,27-,28+/m0/s1
• InChIKey: QOXPZVASXWSKKU-SWNLHRSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-9-en-5-ol
• IUPAC Traditional name: (1R,2S,5S,11R,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-9-en-5-ol
• Synonyms: (3β,5α,22E)-Ergosta-7,22-dien-3-ol; 5α-Ergosta-7,22-dien-3β-ol; (22E)-Ergosta-7,22-dien-3β-ol; (22E,24R)-Ergosta-7,22-dien-3β-ol; (24S)-24-Methyl-5α-cholesta-7,22-dien-3β-ol; 24-Methyl-5α-cholesta-7,22-dien-3β-ol; 5-Dihydroergosterin; Ergosta-7,22-dienol; Stellasterin; α-Dihydroergosterol; Stellasterol

Database IDs

• CAS Number: 2465-11-4
• PubChem SID: 164233788
• PubChem CID: 13889661

CALCULATED PROPERTIES

• Acid pKa: 18.361778
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 7.0379863
• LogD (pH = 7.4): 7.0379863
• Log P: 7.0379863
• Molar Refractivity: 126.2817 cm^3
• Polarizability: 49.590298 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S686680

One of the six sterols isolated from the fruiting bodies of Boletus pulverulentus Opat. (Boletaceae) and identified as (22E)-Ergosta-5,7,9(11),22-tetraen-3β-ol, Ergosterol, Ergosta-5,7-dien-3β-ol, (22E)-Ergosta-5,8,22-trien-3β-ol, (22E)-Ergosta-7,22-dien-

REFERENCES

• Toi, K., et al.: J. Tohoku Pharma. Univ., 54, 49 (2007)