24-epi-Brassinolide

Details

• Internal ID: 981b5d83-e6a1-40c0-9768-25983759da44
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Brassinolides and derivatives
• IUPAC Name: (1S,2R,4R,5S,7S,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
• SMILES (Canonical): CC(C)C(C)C(C(C(C)C1CCC2C1(CCC3C2COC(=O)C4C3(CC(C(C4)O)O)C)C)O)O
• SMILES (Isomeric): C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2COC(=O)[C@@H]4[C@@]3(C[C@H]([C@H](C4)O)O)C)C)[C@H]([C@@H]([C@H](C)C(C)C)O)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
• InChI Key: IXVMHGVQKLDRKH-QHBHMFGVSA-N
• Popularity: 951 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₈O₆
• Molecular Weight: 480.70 g/mol
• Exact Mass: 480.34508925 g/mol
• Topological Polar Surface Area (TPSA): 107.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 3.39
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• 78821-43-9
• 24-epi-Brassinolide
• 24-Epibrassinolide
• Sunergist ebr
• Epibrassinolide R
• 24(R)-Epibrassinolide
• 72962-43-7
• CHEBI:27722
• 24-Epibrassinolide;B1105;BP55
• 49CN25465Y
• B-1105
• (22R,23R)-2alpha,3alpha,22,23-tetrahydroxy-7a-homo-7-oxa-5alpha-ergostan-6-one
• (1S,2R,4R,5S,7S,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
• Brassin lactone
• C28H48O6
• (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
• C28-H48-O6
• Epibrassinolide, >=85%
• BP55
• CHEMBL563853
• SCHEMBL1614884
• UNII-49CN25465Y
• (2-alpha,3-alpha,5-alpha,22R,23R,24S)-2,3,22,23-tetrahydroxy-B-homo-7-oxaergostan-6-one
• HY-N0848
• LMST01140002
• MFCD00133310
• s8870
• AKOS027250811
• CS-3129
• AS-76479
• Q27103283
• 2,3,22,23-Tetrahydroxy-24-methyl-B-homo-7-oxacholestan-6-one
• (22R,23R,24R)-2alpha,3alpha,22,23-Tetrahydroxy-b-homo-7-oxa-5alpha-ergostan-6-one
• B-HOMO-7-oxaergostan-6-one, 2,3,22,23-tetrahydroxy-, (2alpha,3alpha,5alpha,22R,23R)-
• (22R,23R,24R)-2.ALPHA.,3.ALPHA.,22,23-TETRAHYDROXY-B-HOMO-7-OXA-5.ALPHA.-ERGOSTAN-6-ONE
• 3H-Benz[c]indeno[5,4-e]oxepin-3-one, 10-[(1S,2R,3R,4R)-2,3-dihydroxy-1,4,5-trimethylhexyl]hexadecahydro-5,6-dihydroxy-7a,9a-dimethyl-, (3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-
• 6H-BENZ(C)INDENO(5,4-E)OXEPIN-6-ONE, 1-(2,3-DIHYDROXY-1,4,5-TRIMETHYLHEXYL)HEXADECAHYDRO-8,9-DIHYDROXY-10A,12A-DIMETHYL-, (1R-(1.ALPHA.(1S*,2R*,3R*,4R*),3A.BETA.,3B.ALPHA.,6A.BETA.,8.BETA.,9.BETA.,10A.ALPHA.,10B.BETA.,12A.ALPHA.))-
• 6H-Benz(C)indeno(5,4-E)oxepin-6-one, 1-(2,3-dihydroxy-1,4,5-trimethylhexyl)hexadecahydro-8,9-dihydroxy-10a,12a-dimethyl-, (1R-(1alpha(1S*,2R*,3R*,4R*),3abeta,3balpha,6abeta,8beta,9beta,10aalpha,10bbeta,12aalpha))-
• B-HOMO-7-OXAERGOSTAN-6-ONE, 2,3,22,23-TETRAHYDROXY-, (2.ALPHA.,3.ALPHA.,5.ALPHA.,22R,23R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9532	95.32%
Caco-2	-	0.6861	68.61%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7928	79.28%
OATP2B1 inhibitior	-	0.5756	57.56%
OATP1B1 inhibitior	+	0.8721	87.21%
OATP1B3 inhibitior	+	0.9317	93.17%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7292	72.92%
BSEP inhibitior	-	0.5978	59.78%
P-glycoprotein inhibitior	-	0.6425	64.25%
P-glycoprotein substrate	-	0.5915	59.15%
CYP3A4 substrate	+	0.7000	70.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8328	83.28%
CYP3A4 inhibition	-	0.8237	82.37%
CYP2C9 inhibition	-	0.8264	82.64%
CYP2C19 inhibition	-	0.8589	85.89%
CYP2D6 inhibition	-	0.9633	96.33%
CYP1A2 inhibition	-	0.7634	76.34%
CYP2C8 inhibition	-	0.8512	85.12%
CYP inhibitory promiscuity	-	0.9818	98.18%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6908	69.08%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9412	94.12%
Skin irritation	-	0.5704	57.04%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5602	56.02%
Micronuclear	-	0.9100	91.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8685	86.85%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.7011	70.11%
Acute Oral Toxicity (c)	III	0.4857	48.57%
Estrogen receptor binding	+	0.5777	57.77%
Androgen receptor binding	+	0.7164	71.64%
Thyroid receptor binding	+	0.5229	52.29%
Glucocorticoid receptor binding	+	0.5824	58.24%
Aromatase binding	-	0.5195	51.95%
PPAR gamma	-	0.5548	55.48%
Honey bee toxicity	-	0.6865	68.65%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9698	96.98%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.16%	85.14%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.45%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.72%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	94.15%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.85%	94.45%
CHEMBL1914	P06276	Butyrylcholinesterase	93.59%	95.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.08%	100.00%
CHEMBL2581	P07339	Cathepsin D	91.06%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	90.27%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.78%	97.09%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	89.34%	96.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.00%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.92%	97.14%
CHEMBL226	P30542	Adenosine A1 receptor	85.54%	95.93%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.88%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.19%	99.23%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.71%	90.71%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.43%	92.88%

Plants that contains it

• Arabidopsis thaliana
• Gypsophila perfoliata
• Rheum rhabarbarum
• Vicia faba

Cross-Links

• PubChem: 443055
• NPASS: NPC239938
• LOTUS: LTS0100606
• wikiData: Q27103283