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

• ChemBase ID: 126223
• Molecular Formular: C28H48O6
• Molecular Mass: 480.67712
• Monoisotopic Mass: 480.34508926
• SMILES: O=C1OC[C@H]2[C@@H]3CC[C@@H]([C@@]3(C)CC[C@@H]2[C@@]2(C)C[C@@H](O)[C@@H](O)C[C@H]12)[C@H](C)[C@@H](O)[C@H](O)[C@@H](C)C(C)C
• Canonical SMILES: O[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)[C@@H]([C@H](C(C)C)C)O
• InChI: InChI=1S/C28H48O6/c1-14(2)15(3)24(31)25(32)16(4)18-7-8-19-17-13-34-26(33)21-11-22(29)23(30)12-28(21,6)20(17)9-10-27(18,19)5/h14-25,29-32H,7-13H2,1-6H3/t15-,16-,17-,18+,19-,20-,21+,22-,23+,24+,25+,27+,28+/m0/s1
• InChIKey: IXVMHGVQKLDRKH-KNBKMWSGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3R,4R,5S)-3,4-dihydroxy-5,6-dimethylheptan-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: brassinolide
• Synonyms: (1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-1-[(1S,2R,3R,4S)-2,3-Dihydroxy-1,4,5-trimethylhexyl]hexadecahydro-8,9-dihydroxy-10a,12a-dimethyl-6H-benz[c]indeno[5,4-e]oxepin-6-one; (2α,3α,5α,22R,23R,24S)-2,3,22,23-Tetrahydroxy-B-homo-7-oxaergostan-6-one; Brassinolide >90%; 2,3,22,23-Tetrahydroxy-β-homo-7-oxaergostan-6-one; Brassinolide

Database IDs

• CAS Number: 72962-43-7
• PubChem SID: 162220563
• PubChem CID: 115196
• CHEBI ID: 28277
• Chemspider ID: 103072
• Wikipedia Title: Brassinolide

CALCULATED PROPERTIES

• Acid pKa: 13.453601
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.1300669
• LogD (pH = 7.4): 3.1300664
• Log P: 3.1300669
• Molar Refractivity: 130.4066 cm^3
• Polarizability: 52.64235 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 200-204°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B677050

Plant hormone; natural steroid containing a seven-membered B-ring lactone, that promotes both cell elongation and cell devision. Over ten brossinosteroids have been isolated and characterized from sources such as pollen, seedling, leaf. Used as plant grow

REFERENCES

• Grove, M.D., et al.: Nature, 281, 216 (1979)
• Schlagnhaufer, C., et al.: Physiol. Plant., 60, 347 (1979)
• Wada, K., et al.: Agric. Biol. Chem., 48, 719 (1979)