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28-Norbrassinolide

Table of Contents

Details
Physical and Chemical Properties
Synonyms
2D Structure
3D Structure
ADMET Properties
Targets (proven and/or predicted)
Plants that contains it
Cross-Links

Details

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Internal ID e6c1b1bd-951d-4086-b151-d0eb0dfb6ada
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)-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
SMILES (Canonical) CC(C)CC(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](CC(C)C)O)O
InChI InChI=1S/C27H46O6/c1-14(2)10-22(29)24(31)15(3)17-6-7-18-16-13-33-25(32)20-11-21(28)23(30)12-27(20,5)19(16)8-9-26(17,18)4/h14-24,28-31H,6-13H2,1-5H3/t15-,16-,17+,18-,19-,20+,21-,22+,23+,24+,26+,27+/m0/s1
InChI Key CJNLSQRTIXIHGW-BNYRCUELSA-N
Popularity 5 references in papers

Physical and Chemical Properties

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Molecular Formula C27H46O6
Molecular Weight 466.60 g/mol
Exact Mass 466.32943918 g/mol
Topological Polar Surface Area (TPSA) 107.00 Ų
XlogP 4.40
Atomic LogP (AlogP) 3.14
H-Bond Acceptor 6
H-Bond Donor 4
Rotatable Bonds 5

Synonyms

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77736-43-7
28-Nor Brassinolide
(1S,2R,4R,5S,7S,11S,12S,15R,16S)-15-[(2S,3R,4R)-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
DTXSID00551143
(3aS,5S,6R,7aR,7bS,9aS,10R,12aS,12bS)-10-[(3R,4R)-3,4-Dihydroxy-6-methylheptan-2-yl]-5,6-dihydroxy-7a,9a-dimethylhexadecahydro-3H-benzo[c]indeno[5,4-e]oxepin-3-one

2D Structure

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2D Structure of 28-Norbrassinolide

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9481 94.81%
Caco-2 - 0.7066 70.66%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7998 79.98%
OATP2B1 inhibitior - 0.5720 57.20%
OATP1B1 inhibitior + 0.8611 86.11%
OATP1B3 inhibitior + 0.9356 93.56%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7792 77.92%
BSEP inhibitior - 0.4737 47.37%
P-glycoprotein inhibitior - 0.6318 63.18%
P-glycoprotein substrate + 0.5613 56.13%
CYP3A4 substrate + 0.7086 70.86%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8328 83.28%
CYP3A4 inhibition - 0.7998 79.98%
CYP2C9 inhibition - 0.8214 82.14%
CYP2C19 inhibition - 0.8649 86.49%
CYP2D6 inhibition - 0.9667 96.67%
CYP1A2 inhibition - 0.8174 81.74%
CYP2C8 inhibition - 0.8113 81.13%
CYP inhibitory promiscuity - 0.9681 96.81%
UGT catelyzed + 0.9000 90.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.7250 72.50%
Eye corrosion - 0.9922 99.22%
Eye irritation - 0.9401 94.01%
Skin irritation - 0.5664 56.64%
Skin corrosion - 0.9461 94.61%
Ames mutagenesis - 0.7000 70.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4633 46.33%
Micronuclear - 0.9300 93.00%
Hepatotoxicity + 0.5500 55.00%
skin sensitisation - 0.8773 87.73%
Respiratory toxicity + 0.8333 83.33%
Reproductive toxicity + 0.8111 81.11%
Mitochondrial toxicity + 0.8375 83.75%
Nephrotoxicity - 0.8257 82.57%
Acute Oral Toxicity (c) III 0.5159 51.59%
Estrogen receptor binding + 0.5437 54.37%
Androgen receptor binding + 0.7403 74.03%
Thyroid receptor binding + 0.5413 54.13%
Glucocorticoid receptor binding + 0.6721 67.21%
Aromatase binding + 0.5368 53.68%
PPAR gamma - 0.5052 50.52%
Honey bee toxicity - 0.7073 70.73%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9721 97.21%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.31% 97.25%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 97.06% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 95.93% 85.14%
CHEMBL2581 P07339 Cathepsin D 95.63% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 94.54% 91.11%
CHEMBL226 P30542 Adenosine A1 receptor 94.46% 95.93%
CHEMBL3137262 O60341 LSD1/CoREST complex 93.45% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 92.50% 100.00%
CHEMBL3837 P07711 Cathepsin L 90.32% 96.61%
CHEMBL332 P03956 Matrix metalloproteinase-1 90.12% 94.50%
CHEMBL237 P41145 Kappa opioid receptor 90.01% 98.10%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 89.05% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 86.78% 90.17%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.18% 89.00%
CHEMBL2179 P04062 Beta-glucocerebrosidase 85.60% 85.31%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 85.51% 97.14%
CHEMBL3830 Q2M2I8 Adaptor-associated kinase 84.69% 83.10%
CHEMBL2094135 Q96BI3 Gamma-secretase 84.26% 98.05%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 83.76% 95.89%
CHEMBL4227 P25090 Lipoxin A4 receptor 83.32% 100.00%
CHEMBL1871 P10275 Androgen Receptor 82.32% 96.43%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 82.31% 90.71%
CHEMBL4685 P14902 Indoleamine 2,3-dioxygenase 82.09% 96.38%
CHEMBL4208 P20618 Proteasome component C5 81.68% 90.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 80.79% 95.56%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Distylium racemosum
Equisetum arvense

Cross-Links

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PubChem 13845880
LOTUS LTS0186770
wikiData Q82430665