(1S,2R,4R,5S,7S,10S,11S,14R,15S)-14-[(2S,3R,4R,5R)-5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl]-4,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.02,7.011,15]heptadecan-8-one

• ChemBase ID: 170006
• Molecular Formular: C29H50O5
• Molecular Mass: 478.7043
• Monoisotopic Mass: 478.3658247
• SMILES: [C@@H]1([C@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](CC2=O)[C@H]2[C@](CC1)([C@H](CC2)[C@@H]([C@H]([C@@H]([C@@H](C(C)C)CC)O)O)C)C)C)O)O
• Canonical SMILES: CC[C@@H]([C@H]([C@@H]([C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC(=O)[C@@H]2[C@]1(C)C[C@@H](O)[C@H](C2)O)C)O)O)C(C)C
• InChI: InChI=1S/C29H50O5/c1-7-17(15(2)3)27(34)26(33)16(4)19-8-9-20-18-12-23(30)22-13-24(31)25(32)14-29(22,6)21(18)10-11-28(19,20)5/h15-22,24-27,31-34H,7-14H2,1-6H3/t16-,17+,18-,19+,20-,21-,22+,24-,25+,26+,27+,28+,29+/m0/s1
• InChIKey: WADMTJKRYLAHQV-JZSPVGNFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4R,5S,7S,10S,11S,14R,15S)-14-[(2S,3R,4R,5R)-5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl]-4,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-8-one
• IUPAC Traditional name: (1S,2R,4R,5S,7S,10S,11S,14R,15S)-14-[(2S,3R,4R,5R)-5-ethyl-3,4-dihydroxy-6-methylheptan-2-yl]-4,5-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadecan-8-one
• Synonyms: (2α,3α,5α,22R,23R)-2,3,22,23-Tetrahydroxystigmastan-6-one; (24S)-24-Ethylbrassinone; Homocastasterone; 28-Homo Castasterone

Database IDs

• CAS Number: 83509-42-6
• PubChem SID: 164225916
• PubChem CID: 134291

CALCULATED PROPERTIES

• Acid pKa: 13.451744
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.9461875
• LogD (pH = 7.4): 3.946187
• Log P: 3.9461875
• Molar Refractivity: 133.8219 cm^3
• Polarizability: 53.777267 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H590200

Castasterone (C226500) analog. A new brassinosteroid derivative assayed against herpes simplex virus type 1 and 2 in cell cultures.

REFERENCES

• Cassady, K., et al.: J. Antimicrob. Chemother., 39, 119 (1997)
• Ramirez, J., et al.: Steroids, 65, 329 (1997)