(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]heptadeca-7,9-dien-5-ol

• ChemBase ID: 128129
• Molecular Formular: C28H44O
• Molecular Mass: 396.64836
• Monoisotopic Mass: 396.33921603
• SMILES: O[C@@H]1CC2=CC=C3[C@@H](CC[C@]4([C@H]3CC[C@@H]4[C@@H](C=C[C@H](C)C(C)C)C)C)[C@]2(C)CC1
• Canonical SMILES: O[C@H]1CC[C@@]2(C(=CC=C3[C@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](C=C[C@@H](C(C)C)C)C)C)C1)C
• InChI: InChI=1S/C28H44O/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/h7-10,18-20,22,24-26,29H,11-17H2,1-6H3/t19-,20+,22-,24+,25-,26+,27+,28+/m0/s1
• InChIKey: DNVPQKQSNYMLRS-NVGLTBPYSA-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]heptadeca-7,9-dien-5-ol; (1R,2S,5S,11R,14R,15R)-14-[(2R,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,9-dien-5-ol
• IUPAC Traditional name: lumisterol; (1R,2S,5S,11R,14R,15R)-14-[(2R,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,9-dien-5-ol
• Synonyms: (3β,9β,10α,22E)-Ergosta-5,7,22-trien-3-ol; 9.beta.,10α-Ergosta-5,7,22-trien-3-ol; 9β,10α-Ergosta-5,7,22-trien-3.beta.-ol; 9β,10α-Ergosterol; Lumisterol2; Lumisterol

Database IDs

• CAS Number: 474-69-1
• PubChem SID: 162222443
• PubChem CID: 6436872; 101703
• Chemspider ID: 4941479
• Wikipedia Title: Lumisterol

CALCULATED PROPERTIES

• Acid pKa: 18.270805
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 6.6324067
• LogD (pH = 7.4): 6.632407
• Log P: 6.632407
• Molar Refractivity: 127.1317 cm^3
• Polarizability: 49.356697 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - L474800

C10 isomer of Ergosterol (E599240). Used in the preparation of vitamin D series.

REFERENCES

• Yamamoto, J.K., et al.: Biochemistry, 24, 3338 (1985)