(1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3R,4R)-3,4-dihydroxy-6-methylheptan-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.02,7.012,16]octadecan-8-one

• ChemBase ID: 175581
• Molecular Formular: C27H46O6
• Molecular Mass: 466.65054
• Monoisotopic Mass: 466.32943919
• SMILES: [C@@H]1([C@H](C[C@H]2[C@](C1)([C@@H]1[C@@H](COC2=O)[C@H]2[C@](CC1)([C@H](CC2)[C@@H]([C@H]([C@@H](CC(C)C)O)O)C)C)C)O)O
• Canonical SMILES: CC(C[C@H]([C@@H]([C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2COC(=O)[C@@H]2[C@]1(C)C[C@@H](O)[C@H](C2)O)C)O)O)C
• InChI: InChI=1S/C27H46O6/c1-14(2)10-22(29)24(31)15(3)17-6-7-18-16-13-33-25(32)20-11-21(28)23(30)12-27(20,5)19(16)8-9-26(17,18)4/h14-24,28-31H,6-13H2,1-5H3/t15-,16-,17+,18-,19-,20+,21-,22+,23+,24+,26+,27+/m0/s1
• InChIKey: CJNLSQRTIXIHGW-BNYRCUELSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3R,4R)-3,4-dihydroxy-6-methylheptan-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0^2,^7.0^1^2,^1^6]octadecan-8-one
• IUPAC Traditional name: (1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3R,4R)-3,4-dihydroxy-6-methylheptan-2-yl]-4,5-dihydroxy-2,16-dimethyl-9-oxatetracyclo[9.7.0.0^2,^7.0^1^2,^1^6]octadecan-8-one
• Synonyms: (1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-1-[(1S,2R,3R)-2,3-dihydroxy-1,5-dimethylhexyl]hexadecahydro-8,9-dihydroxy-10a,12a-dimethyl-6H-benz[c]indeno[5,4-e]oxepin-6-one; (2α,3α,5α,22R,23R)-2,3,22,23-Tetrahydroxy-B-homo-7-oxacholestan-6-one; 24-Demethylbrassinolide; Norbrassinolide; 28-Nor Brassinolide

Database IDs

• CAS Number: 77736-43-7
• PubChem SID: 164231491
• PubChem CID: 13845880

CALCULATED PROPERTIES

• Acid pKa: 13.517809
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 2.765094
• LogD (pH = 7.4): 2.7650938
• Log P: 2.765094
• Molar Refractivity: 125.935 cm^3
• Polarizability: 50.80482 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N661280

A metabolite of Brassinolide (B677050). A new type of modified brassinosteroids for enzyme-linked immunosorbent assay.

REFERENCES

• Suzuki, H., et al.: Phytochemistry, 33, 1361 (1993)
• Fujioka, S., et al.: Biosci. Biotech. Biochem., 59, 1973 (1993)