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[(3aS,4S,5S,5aR,6R,9S,9aS,9bR)-6,9-dihydroxy-5a,9-dimethyl-5-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate

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 b688c9e5-017d-44f7-b4f3-02c4714e53c1
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Eudesmanolides, secoeudesmanolides, and derivatives
IUPAC Name [(3aS,4S,5S,5aR,6R,9S,9aS,9bR)-6,9-dihydroxy-5a,9-dimethyl-5-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate
SMILES (Canonical) CC=C(C)C(=O)OC1C(C2C(C3C1(C(CCC3(C)O)O)C)OC(=O)C2=C)OC(=O)C4(C(O4)C)C
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@@H]1[C@H]([C@@H]2[C@H]([C@@H]3[C@@]1([C@@H](CC[C@]3(C)O)O)C)OC(=O)C2=C)OC(=O)[C@@]4([C@@H](O4)C)C
InChI InChI=1S/C25H34O9/c1-8-11(2)20(27)33-19-17(32-22(29)25(7)13(4)34-25)15-12(3)21(28)31-16(15)18-23(5,30)10-9-14(26)24(18,19)6/h8,13-19,26,30H,3,9-10H2,1-2,4-7H3/b11-8-/t13-,14+,15-,16+,17-,18-,19+,23-,24-,25-/m0/s1
InChI Key DZIKAAXWHIYYQU-KHZOSGKMSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C25H34O9
Molecular Weight 478.50 g/mol
Exact Mass 478.22028266 g/mol
Topological Polar Surface Area (TPSA) 132.00 Ų
XlogP 2.20
Atomic LogP (AlogP) 1.59
H-Bond Acceptor 9
H-Bond Donor 2
Rotatable Bonds 4

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aS,4S,5S,5aR,6R,9S,9aS,9bR)-6,9-dihydroxy-5a,9-dimethyl-5-[(Z)-2-methylbut-2-enoyl]oxy-3-methylidene-2-oxo-3a,4,5,6,7,8,9a,9b-octahydrobenzo[g][1]benzofuran-4-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9840 98.40%
Caco-2 - 0.6590 65.90%
Blood Brain Barrier + 0.7500 75.00%
Human oral bioavailability - 0.6000 60.00%
Subcellular localzation Mitochondria 0.6447 64.47%
OATP2B1 inhibitior - 0.8581 85.81%
OATP1B1 inhibitior + 0.8587 85.87%
OATP1B3 inhibitior + 0.8682 86.82%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.6553 65.53%
BSEP inhibitior + 0.6448 64.48%
P-glycoprotein inhibitior + 0.6626 66.26%
P-glycoprotein substrate - 0.5429 54.29%
CYP3A4 substrate + 0.6831 68.31%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8856 88.56%
CYP3A4 inhibition + 0.5954 59.54%
CYP2C9 inhibition - 0.8302 83.02%
CYP2C19 inhibition - 0.8929 89.29%
CYP2D6 inhibition - 0.9350 93.50%
CYP1A2 inhibition - 0.7717 77.17%
CYP2C8 inhibition - 0.6038 60.38%
CYP inhibitory promiscuity - 0.9083 90.83%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.4171 41.71%
Eye corrosion - 0.9874 98.74%
Eye irritation - 0.9110 91.10%
Skin irritation + 0.4914 49.14%
Skin corrosion - 0.8509 85.09%
Ames mutagenesis - 0.6196 61.96%
Human Ether-a-go-go-Related Gene inhibition - 0.4239 42.39%
Micronuclear - 0.6200 62.00%
Hepatotoxicity + 0.6750 67.50%
skin sensitisation - 0.7728 77.28%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.9111 91.11%
Mitochondrial toxicity + 0.8250 82.50%
Nephrotoxicity + 0.5697 56.97%
Acute Oral Toxicity (c) III 0.3594 35.94%
Estrogen receptor binding + 0.7619 76.19%
Androgen receptor binding + 0.6626 66.26%
Thyroid receptor binding + 0.5926 59.26%
Glucocorticoid receptor binding + 0.6838 68.38%
Aromatase binding + 0.6968 69.68%
PPAR gamma + 0.6565 65.65%
Honey bee toxicity - 0.6815 68.15%
Biodegradation - 0.8500 85.00%
Crustacea aquatic toxicity - 0.5400 54.00%
Fish aquatic toxicity + 0.9763 97.63%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 97.45% 91.11%
CHEMBL2581 P07339 Cathepsin D 95.14% 98.95%
CHEMBL221 P23219 Cyclooxygenase-1 92.76% 90.17%
CHEMBL3038477 P67870 Casein kinase II alpha/beta 90.47% 99.23%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 90.28% 95.56%
CHEMBL253 P34972 Cannabinoid CB2 receptor 90.22% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 89.36% 89.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 89.34% 95.89%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 88.43% 97.14%
CHEMBL3807 P17706 T-cell protein-tyrosine phosphatase 87.15% 93.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 86.09% 91.07%
CHEMBL1293249 Q13887 Kruppel-like factor 5 85.95% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 85.68% 94.45%
CHEMBL340 P08684 Cytochrome P450 3A4 85.31% 91.19%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.13% 97.09%
CHEMBL1994 P08235 Mineralocorticoid receptor 84.22% 100.00%
CHEMBL1907600 Q00535 Cyclin-dependent kinase 5/CDK5 activator 1 82.61% 93.03%
CHEMBL1902 P62942 FK506-binding protein 1A 82.52% 97.05%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 80.63% 95.50%

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.
Calostephane divaricata

Cross-Links

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PubChem 14314444
LOTUS LTS0150031
wikiData Q104991818