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[(3aR,4S,5aS,6S,9aR,9bS)-6-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] (3S)-3-hydroxy-2-methylidenebutanoate

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 a63f920c-6ba4-4a50-bcf3-0dff2539b42b
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aR,4S,5aS,6S,9aR,9bS)-6-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] (3S)-3-hydroxy-2-methylidenebutanoate
SMILES (Canonical) CC(C(=C)C(=O)OC1CC2(C(CCC(=C)C2C3C1C(=C)C(=O)O3)O)C)O
SMILES (Isomeric) C[C@@H](C(=C)C(=O)O[C@H]1C[C@@]2([C@H](CCC(=C)[C@H]2[C@H]3[C@@H]1C(=C)C(=O)O3)O)C)O
InChI InChI=1S/C20H26O6/c1-9-6-7-14(22)20(5)8-13(25-18(23)10(2)12(4)21)15-11(3)19(24)26-17(15)16(9)20/h12-17,21-22H,1-3,6-8H2,4-5H3/t12-,13-,14-,15+,16-,17+,20+/m0/s1
InChI Key VJRYIIQKNCTAMU-MAHXWWMISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C20H26O6
Molecular Weight 362.40 g/mol
Exact Mass 362.17293854 g/mol
Topological Polar Surface Area (TPSA) 93.10 Ų
XlogP 1.80
Atomic LogP (AlogP) 1.67
H-Bond Acceptor 6
H-Bond Donor 2
Rotatable Bonds 3

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,5aS,6S,9aR,9bS)-6-hydroxy-5a-methyl-3,9-dimethylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] (3S)-3-hydroxy-2-methylidenebutanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9917 99.17%
Caco-2 - 0.5597 55.97%
Blood Brain Barrier + 0.6250 62.50%
Human oral bioavailability - 0.5714 57.14%
Subcellular localzation Mitochondria 0.7613 76.13%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8887 88.87%
OATP1B3 inhibitior + 0.8375 83.75%
MATE1 inhibitior - 0.9000 90.00%
OCT2 inhibitior - 0.6152 61.52%
BSEP inhibitior - 0.9387 93.87%
P-glycoprotein inhibitior - 0.7858 78.58%
P-glycoprotein substrate - 0.6539 65.39%
CYP3A4 substrate + 0.6675 66.75%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8532 85.32%
CYP3A4 inhibition + 0.5052 50.52%
CYP2C9 inhibition - 0.8847 88.47%
CYP2C19 inhibition - 0.9218 92.18%
CYP2D6 inhibition - 0.9526 95.26%
CYP1A2 inhibition - 0.7280 72.80%
CYP2C8 inhibition - 0.6788 67.88%
CYP inhibitory promiscuity - 0.9314 93.14%
UGT catelyzed - 0.7000 70.00%
Carcinogenicity (binary) - 1.0000 100.00%
Carcinogenicity (trinary) Non-required 0.5433 54.33%
Eye corrosion - 0.9900 99.00%
Eye irritation - 0.8617 86.17%
Skin irritation + 0.5450 54.50%
Skin corrosion - 0.8905 89.05%
Ames mutagenesis - 0.7100 71.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4030 40.30%
Micronuclear - 0.6900 69.00%
Hepatotoxicity + 0.8033 80.33%
skin sensitisation - 0.7895 78.95%
Respiratory toxicity + 0.6667 66.67%
Reproductive toxicity + 0.9222 92.22%
Mitochondrial toxicity + 0.9625 96.25%
Nephrotoxicity + 0.5286 52.86%
Acute Oral Toxicity (c) I 0.4163 41.63%
Estrogen receptor binding + 0.8018 80.18%
Androgen receptor binding + 0.6415 64.15%
Thyroid receptor binding + 0.6040 60.40%
Glucocorticoid receptor binding + 0.7749 77.49%
Aromatase binding - 0.5000 50.00%
PPAR gamma + 0.5706 57.06%
Honey bee toxicity - 0.6400 64.00%
Biodegradation - 0.8250 82.50%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9968 99.68%

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
CHEMBL4040 P28482 MAP kinase ERK2 97.41% 83.82%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 97.08% 94.45%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.90% 91.11%
CHEMBL221 P23219 Cyclooxygenase-1 96.63% 90.17%
CHEMBL253 P34972 Cannabinoid CB2 receptor 94.72% 97.25%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 91.06% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 89.11% 95.56%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 88.87% 85.14%
CHEMBL3130 O00329 PI3-kinase p110-delta subunit 87.37% 96.47%
CHEMBL2581 P07339 Cathepsin D 85.85% 98.95%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.75% 97.09%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.57% 89.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 84.71% 91.07%
CHEMBL5608 Q16288 NT-3 growth factor receptor 84.17% 95.89%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 83.69% 96.09%
CHEMBL340 P08684 Cytochrome P450 3A4 83.19% 91.19%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 82.71% 95.89%
CHEMBL1994 P08235 Mineralocorticoid receptor 82.46% 100.00%
CHEMBL3351 Q13085 Acetyl-CoA carboxylase 1 81.81% 93.04%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 81.26% 97.14%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
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There are no matching plants.

Cross-Links

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PubChem 162869422
LOTUS LTS0197181
wikiData Q105287476