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[(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2S)-3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate

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 5e75c063-7e47-4823-9ab1-cecefd017ad8
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2S)-3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate
SMILES (Canonical) CC(CCl)(C(=O)OC1CC(=C)C2CC(C(C2C3C1C(=C)C(=O)O3)(CCl)O)O)OCCC4=CC=C(C=C4)O
SMILES (Isomeric) C[C@@](CCl)(C(=O)O[C@H]1CC(=C)[C@@H]2C[C@@H]([C@@]([C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)(CCl)O)O)OCCC4=CC=C(C=C4)O
InChI InChI=1S/C27H32Cl2O8/c1-14-10-19(36-25(33)26(3,12-28)35-9-8-16-4-6-17(30)7-5-16)21-15(2)24(32)37-23(21)22-18(14)11-20(31)27(22,34)13-29/h4-7,18-23,30-31,34H,1-2,8-13H2,3H3/t18-,19-,20-,21+,22-,23-,26+,27+/m0/s1
InChI Key VLUKWHIZVPGABG-LSEJKCCISA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H32Cl2O8
Molecular Weight 555.40 g/mol
Exact Mass 554.1474234 g/mol
Topological Polar Surface Area (TPSA) 123.00 Ų
XlogP 3.00
Atomic LogP (AlogP) 2.89
H-Bond Acceptor 8
H-Bond Donor 3
Rotatable Bonds 8

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2S)-3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9761 97.61%
Caco-2 - 0.8537 85.37%
Blood Brain Barrier - 0.5250 52.50%
Human oral bioavailability - 0.7000 70.00%
Subcellular localzation Mitochondria 0.7943 79.43%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7906 79.06%
OATP1B3 inhibitior + 0.9272 92.72%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.7750 77.50%
BSEP inhibitior + 0.8529 85.29%
P-glycoprotein inhibitior + 0.6231 62.31%
P-glycoprotein substrate + 0.6817 68.17%
CYP3A4 substrate + 0.7350 73.50%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8387 83.87%
CYP3A4 inhibition - 0.6811 68.11%
CYP2C9 inhibition - 0.6582 65.82%
CYP2C19 inhibition - 0.5831 58.31%
CYP2D6 inhibition - 0.8922 89.22%
CYP1A2 inhibition - 0.5561 55.61%
CYP2C8 inhibition + 0.8158 81.58%
CYP inhibitory promiscuity - 0.9084 90.84%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.8344 83.44%
Carcinogenicity (trinary) Non-required 0.4871 48.71%
Eye corrosion - 0.9870 98.70%
Eye irritation - 0.9368 93.68%
Skin irritation - 0.6521 65.21%
Skin corrosion - 0.9191 91.91%
Ames mutagenesis - 0.6800 68.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4698 46.98%
Micronuclear - 0.7900 79.00%
Hepatotoxicity + 0.6052 60.52%
skin sensitisation - 0.8388 83.88%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.8778 87.78%
Mitochondrial toxicity + 0.8500 85.00%
Nephrotoxicity + 0.8140 81.40%
Acute Oral Toxicity (c) III 0.4270 42.70%
Estrogen receptor binding + 0.7775 77.75%
Androgen receptor binding + 0.7507 75.07%
Thyroid receptor binding + 0.5891 58.91%
Glucocorticoid receptor binding + 0.7819 78.19%
Aromatase binding + 0.7097 70.97%
PPAR gamma + 0.6531 65.31%
Honey bee toxicity - 0.5966 59.66%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.5353 53.53%
Fish aquatic toxicity + 1.0000 100.00%

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 98.83% 91.11%
CHEMBL253 P34972 Cannabinoid CB2 receptor 97.90% 97.25%
CHEMBL2996 Q05655 Protein kinase C delta 97.09% 97.79%
CHEMBL2581 P07339 Cathepsin D 96.81% 98.95%
CHEMBL2035 P08912 Muscarinic acetylcholine receptor M5 96.14% 94.62%
CHEMBL1293249 Q13887 Kruppel-like factor 5 95.91% 86.33%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.12% 94.45%
CHEMBL211 P08172 Muscarinic acetylcholine receptor M2 95.00% 94.97%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 94.24% 96.09%
CHEMBL5966 P55899 IgG receptor FcRn large subunit p51 91.63% 90.93%
CHEMBL3137262 O60341 LSD1/CoREST complex 91.33% 97.09%
CHEMBL3713062 P10646 Tissue factor pathway inhibitor 90.00% 97.33%
CHEMBL5608 Q16288 NT-3 growth factor receptor 87.10% 95.89%
CHEMBL3004 P33527 Multidrug resistance-associated protein 1 86.47% 96.37%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.03% 95.56%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 82.26% 94.00%
CHEMBL340 P08684 Cytochrome P450 3A4 80.71% 91.19%
CHEMBL1902 P62942 FK506-binding protein 1A 80.71% 97.05%
CHEMBL5163 Q9NY46 Sodium channel protein type III alpha subunit 80.64% 96.90%
CHEMBL1806 P11388 DNA topoisomerase II alpha 80.15% 89.00%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 80.12% 95.89%

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.
Klasea centauroides subsp. strangulata

Cross-Links

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PubChem 21593843
LOTUS LTS0080785
wikiData Q105288714