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(2aR,3R,5R,5aR,6aS,6bR,10aR,11R,12aS,12bS,12cS)-5a,10a,11-trihydroxy-3-(hydroxymethyl)-3',4',6b,12c-tetramethylspiro[2,2a,3,6,6a,10,11,12,12a,12b-decahydro-1H-benzo[j]aceanthrylene-5,5'-furan]-2',4,7-trione

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 0af30b70-0c0a-4986-a635-b8d317fa6184
Taxonomy Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
IUPAC Name (2aR,3R,5R,5aR,6aS,6bR,10aR,11R,12aS,12bS,12cS)-5a,10a,11-trihydroxy-3-(hydroxymethyl)-3',4',6b,12c-tetramethylspiro[2,2a,3,6,6a,10,11,12,12a,12b-decahydro-1H-benzo[j]aceanthrylene-5,5'-furan]-2',4,7-trione
SMILES (Canonical) CC1=C(C2(C(=O)C(C3CCC4C3(C2(CC5C4CC(C6(C5(C(=O)C=CC6)C)O)O)O)C)CO)OC1=O)C
SMILES (Isomeric) CC1=C([C@@]2(C(=O)[C@H]([C@H]3CC[C@@H]4[C@@]3([C@@]2(C[C@H]5[C@H]4C[C@H]([C@@]6([C@@]5(C(=O)C=CC6)C)O)O)O)C)CO)OC1=O)C
InChI InChI=1S/C28H36O8/c1-13-14(2)28(36-23(13)33)22(32)16(12-29)18-8-7-17-15-10-21(31)26(34)9-5-6-20(30)25(26,4)19(15)11-27(28,35)24(17,18)3/h5-6,15-19,21,29,31,34-35H,7-12H2,1-4H3/t15-,16-,17-,18+,19-,21+,24-,25-,26-,27+,28-/m0/s1
InChI Key HFZGKWYSNFCBNR-BGDRCPOJSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C28H36O8
Molecular Weight 500.60 g/mol
Exact Mass 500.24101810 g/mol
Topological Polar Surface Area (TPSA) 141.00 Ų
XlogP 1.30
Atomic LogP (AlogP) 1.24
H-Bond Acceptor 8
H-Bond Donor 4
Rotatable Bonds 1

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2aR,3R,5R,5aR,6aS,6bR,10aR,11R,12aS,12bS,12cS)-5a,10a,11-trihydroxy-3-(hydroxymethyl)-3',4',6b,12c-tetramethylspiro[2,2a,3,6,6a,10,11,12,12a,12b-decahydro-1H-benzo[j]aceanthrylene-5,5'-furan]-2',4,7-trione

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9563 95.63%
Caco-2 - 0.6340 63.40%
Blood Brain Barrier + 0.5750 57.50%
Human oral bioavailability - 0.7143 71.43%
Subcellular localzation Mitochondria 0.8353 83.53%
OATP2B1 inhibitior - 0.8676 86.76%
OATP1B1 inhibitior + 0.8761 87.61%
OATP1B3 inhibitior + 0.9509 95.09%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.6064 60.64%
BSEP inhibitior + 0.8420 84.20%
P-glycoprotein inhibitior - 0.5000 50.00%
P-glycoprotein substrate + 0.6237 62.37%
CYP3A4 substrate + 0.7029 70.29%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.9021 90.21%
CYP3A4 inhibition - 0.6634 66.34%
CYP2C9 inhibition - 0.8816 88.16%
CYP2C19 inhibition - 0.9063 90.63%
CYP2D6 inhibition - 0.9473 94.73%
CYP1A2 inhibition - 0.8673 86.73%
CYP2C8 inhibition - 0.5580 55.80%
CYP inhibitory promiscuity - 0.9544 95.44%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.4989 49.89%
Eye corrosion - 0.9913 99.13%
Eye irritation - 0.9457 94.57%
Skin irritation + 0.6465 64.65%
Skin corrosion - 0.9368 93.68%
Ames mutagenesis - 0.5548 55.48%
Human Ether-a-go-go-Related Gene inhibition + 0.6726 67.26%
Micronuclear - 0.8000 80.00%
Hepatotoxicity - 0.5113 51.13%
skin sensitisation - 0.9102 91.02%
Respiratory toxicity + 0.8556 85.56%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8625 86.25%
Nephrotoxicity + 0.5790 57.90%
Acute Oral Toxicity (c) III 0.5160 51.60%
Estrogen receptor binding + 0.8169 81.69%
Androgen receptor binding + 0.7771 77.71%
Thyroid receptor binding - 0.5175 51.75%
Glucocorticoid receptor binding + 0.7986 79.86%
Aromatase binding + 0.7806 78.06%
PPAR gamma + 0.5227 52.27%
Honey bee toxicity - 0.8172 81.72%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity + 0.5800 58.00%
Fish aquatic toxicity + 0.9660 96.60%

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
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.28% 85.14%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.62% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 96.30% 95.56%
CHEMBL226 P30542 Adenosine A1 receptor 93.10% 95.93%
CHEMBL2996 Q05655 Protein kinase C delta 92.72% 97.79%
CHEMBL1994 P08235 Mineralocorticoid receptor 91.99% 100.00%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.68% 97.09%
CHEMBL2581 P07339 Cathepsin D 89.95% 98.95%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 88.33% 91.11%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.38% 89.00%
CHEMBL1937 Q92769 Histone deacetylase 2 84.18% 94.75%
CHEMBL218 P21554 Cannabinoid CB1 receptor 84.02% 96.61%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 83.36% 99.23%
CHEMBL253 P34972 Cannabinoid CB2 receptor 83.04% 97.25%
CHEMBL1871 P10275 Androgen Receptor 82.07% 96.43%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 81.91% 96.95%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.60% 97.14%

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.
Jaborosa runcinata

Cross-Links

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PubChem 101769649
LOTUS LTS0236922
wikiData Q105027643