Structure Database (LMSD)
Common Name
24-epi-brassinolide
Systematic Name
(22R,23R)-2α,3α,22,23-tetrahydroxy-7a-homo-7-oxa-5α-ergostan-6-one
Synonyms
- 24-epi-Brassinolide
LM ID
LMST01140002
Formula
Exact Mass
Calculate m/z
480.34509
Sum Composition
Status
Curated
3D model of 24-epi-brassinolide
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Epibrassinolide is a brassinosteroid that can be isolated from various plants and has been shown to decrease toxicity and stimulate healthy plant growth in plants under stress.1 Epibrassinolide is also reported to be a potential apoptotic inducer in various cancer cells without affecting the non-tumor cell growth.2 It has also been shown to protect neuronal PC12 cells from 1-methyl-4-phenylpyridinium-induced oxidative stress and consequent apoptosis in dopaminergic neurons.3
This information has been provided by Cayman Chemical
References
2. Obakan, P., Barrero, C., Coker-Gurkan, A., et al. SILAC-based mass pectrometry analysis reveals that epibrassinolide induces apoptosis via activating endoplasmic reticulum stress in prostate cancer cells. PLoS One 10(9), (2015).
3. Sondhi, N., Bhardwaj, R., Kaur, S., et al. Isolation of 24-epibrassinolide from leaves of Aegle marmelos and evaluation of its antigenotoxicity employing Allium cepa chromosomal aberration assay. Plant Growth Regul. 54(3), 217-224 (2008).
References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Vicia faba
(#3906)
Magnoliopsida
(#3398)
Identification of 24-Epibrassinolide in Bee Pollen of the Broad Bean, Vicia faba L.,
Chem Pharm Bull, 1987
Chem Pharm Bull, 1987
DOI:
10.1248/cpb.36.405
String Representations
InChiKey (Click to copy)
IXVMHGVQKLDRKH-QHBHMFGVSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
C1C[C@]([H])([C@H](C)[C@@H](O)[C@H](O)[C@H](C)C(C)C)[C@@]2(C)CC[C@@]3([H])[C@](COC(=O)[C@@]4([H])C[C@H](O)[C@H](O)C[C@]34C)([H])[C@@]21[H]
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
34
Rings
4
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
493.62
Topological Polar Surface Area
109.29
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
6
logP
4.82
Molar Refractivity
132.06
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Updated at
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