(1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3S,4S,5S)-5-ethyl-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: 132694
• Molecular Formular: C29H50O6
• Molecular Mass: 494.7037
• Monoisotopic Mass: 494.36073932
• SMILES: CC[C@H]([C@@H]([C@H]([C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]1[C@H]2COC(=O)[C@@H]2[C@@]1(C[C@H]([C@H](C2)O)O)C)C)O)O)C(C)C
• 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]2COC(=O)[C@@H]2[C@]1(C)C[C@@H](O)[C@H](C2)O)C)O)O)C(C)C
• InChI: InChI=1S/C29H50O6/c1-7-17(15(2)3)26(33)25(32)16(4)19-8-9-20-18-14-35-27(34)22-12-23(30)24(31)13-29(22,6)21(18)10-11-28(19,20)5/h15-26,30-33H,7-14H2,1-6H3/t16-,17-,18-,19+,20-,21-,22+,23-,24+,25-,26-,28+,29+/m0/s1
• InChIKey: HJIKODJJEORHMZ-DNVPGCTHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3S,4S,5S)-5-ethyl-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,3S,4S,5S)-5-ethyl-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: 22(S),23(S)-Homobrassinolide; (1R,3aS,3bS,6aS,8S,9R,10aR,10bS,12aS)-1-[(1S,2S,3S,4S)-4-Ethyl-2,3-dihydroxy-1,5-dimethylhexyl]hexadecahydro-8,9-dihydroxy-10a,12a-dimethyl-6H-benz[c]indeno[5,4-e]oxepin-6-one; Isohomobrassinolide; BR 120; (22S,23S)-28-Homo Brassinolide

Database IDs

• CAS Number: 80483-89-2
• MDL Number: MFCD04973608
• PubChem SID: 162226971; 24895446
• PubChem CID: 11409314

CALCULATED PROPERTIES

• Acid pKa: 13.450847
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): 3.5746355
• LogD (pH = 7.4): 3.5746353
• Log P: 3.5746355
• Molar Refractivity: 135.0076 cm^3
• Polarizability: 54.480442 Å^3
• Polar Surface Area: 107.22 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Hexane
• Apperance: Crystalline Solid
• Melting Point: 193-194°C

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

DETAILS

Sigma Aldrich - H1267

Frequently Asked Questions
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Biochem/physiol Actions
Exhibits plant growth regulatory activity.

Toronto Research Chemicals - H589500

A new class of steroidal phytohormones with high growth-promoting and antistress activity.

REFERENCES

• Wang, J., et al.: Biotechnol., Lett., 24, 1573 (2002)
• Azpeitia, A., et al.: J. Horticult. Sci. Biotechnol., 78, 591 (2002)