(1R,2R,5S,11R,14S,15S)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol

• ChemBase ID: 3665
• Molecular Formular: C28H44O
• Molecular Mass: 396.64836
• Monoisotopic Mass: 396.33921603
• SMILES: CC(C)[C@H](C)/C=C/[C@@H](C)[C@@H]1CC[C@H]2C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@H]3CC[C@@]12C
• 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/b8-7+/t19-,20-,22+,24+,25+,26-,27+,28+/m1/s1
• InChIKey: DNVPQKQSNYMLRS-SOWFXMKYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R,5S,11R,14S,15S)-14-[(2R,3E,5S)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-7,9-dien-5-ol
• IUPAC Traditional name: @ergosterol
• Synonyms: Ergosterol

Database IDs

• CAS Number: 57-87-4
• PubChem SID: 46505947; 160967103
• PubChem CID: 46936866

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 7.39
• LOG S: -6.41
• Solubility (Water): 1.56e-04 g/l

DETAILS

DrugBank - DB04038

• Drug Groups: experimental
• Description: A steroid of interest both because its biosynthesis in FUNGI is a target of ANTIFUNGAL AGENTS, notably AZOLES, and because when it is present in SKIN of animals, ULTRAVIOLET RAYS break a bond to result in ERGOCALCIFEROL. [PubChem]