(1S,2R,4R,5S,11S,12S,15R,16S)-15-[(2S,3R,4R,5R)-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: 168035
• Molecular Formular: C28H48O6
• Molecular Mass: 480.67712
• Monoisotopic Mass: 480.34508926
• SMILES: [C@@H]1([C@H](CC2[C@](C1)([C@@H]1[C@@H](COC2=O)[C@H]2[C@](CC1)([C@H](CC2)[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)C)C)C)C)C)O)O
• Canonical SMILES: O[C@H]([C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2COC(=O)C2[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-/m1/s1
• InChIKey: IXVMHGVQKLDRKH-FKPPCUHPSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 78821-43-9
• PubChem SID: 162262167
• PubChem CID: 13039097

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: Chloroform
• Apperance: White Solid
• Melting Point: 237-240°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E582000

A plant growth stimulant.

REFERENCES

• McMorris, T.C. and Patil, P.A.: J. Org. Chem., 58, 2338-2339 (1993)