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Eupachlorin

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 bd341f64-82ff-4628-bb5f-26fcab7314a2
Taxonomy Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
IUPAC Name [(3aR,4R,6R,6aR,7R,9aS,9bS)-6-(chloromethyl)-6,7,9a-trihydroxy-9-methyl-3-methylidene-2-oxo-3a,4,5,6a,7,9b-hexahydroazuleno[4,5-b]furan-4-yl] (Z)-2-methylbut-2-enoate
SMILES (Canonical) CC=C(C)C(=O)OC1CC(C2C(C=C(C2(C3C1C(=C)C(=O)O3)O)C)O)(CCl)O
SMILES (Isomeric) C/C=C(/C)\C(=O)O[C@@H]1C[C@@]([C@@H]2[C@@H](C=C([C@@]2([C@@H]3[C@@H]1C(=C)C(=O)O3)O)C)O)(CCl)O
InChI InChI=1S/C20H25ClO7/c1-5-9(2)17(23)27-13-7-19(25,8-21)15-12(22)6-10(3)20(15,26)16-14(13)11(4)18(24)28-16/h5-6,12-16,22,25-26H,4,7-8H2,1-3H3/b9-5-/t12-,13-,14-,15+,16+,19+,20-/m1/s1
InChI Key VCAKAFVZYNRGKS-WBNZXOOCSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C20H25ClO7
Molecular Weight 412.90 g/mol
Exact Mass 412.1288808 g/mol
Topological Polar Surface Area (TPSA) 113.00 Ų
XlogP 0.60
Atomic LogP (AlogP) 1.00
H-Bond Acceptor 7
H-Bond Donor 3
Rotatable Bonds 3

Synonyms

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CHEBI:4920
20071-50-5
[(3aR,4R,6R,6aR,7R,9aS,9bS)-6-(chloromethyl)-6,7,9a-trihydroxy-9-methyl-3-methylidene-2-oxo-3a,4,5,6a,7,9b-hexahydroazuleno[4,5-b]furan-4-yl] (Z)-2-methylbut-2-enoate
CHEMBL437014
C09416
DTXSID801099064
Q27106546
(3aR,4R,6R,6aR,7R,9aS,9bS)-6-(Chloromethyl)-2,3,3a,4,5,6,6a,7,9a,9b-decahydro-6,7,9a-trihydroxy-9-methyl-3-methylene-2-oxoazuleno[4,5-b]furan-4-yl (2Z)-2-methyl-2-butenoate

2D Structure

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2D Structure of Eupachlorin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9234 92.34%
Caco-2 - 0.7041 70.41%
Blood Brain Barrier + 0.6500 65.00%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.5195 51.95%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.8929 89.29%
OATP1B3 inhibitior + 0.9219 92.19%
MATE1 inhibitior - 0.9400 94.00%
OCT2 inhibitior - 0.9500 95.00%
BSEP inhibitior - 0.7585 75.85%
P-glycoprotein inhibitior - 0.6485 64.85%
P-glycoprotein substrate - 0.5778 57.78%
CYP3A4 substrate + 0.6699 66.99%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8841 88.41%
CYP3A4 inhibition - 0.6682 66.82%
CYP2C9 inhibition - 0.8290 82.90%
CYP2C19 inhibition - 0.7999 79.99%
CYP2D6 inhibition - 0.9036 90.36%
CYP1A2 inhibition - 0.8409 84.09%
CYP2C8 inhibition - 0.6051 60.51%
CYP inhibitory promiscuity - 0.8402 84.02%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.8444 84.44%
Carcinogenicity (trinary) Non-required 0.4368 43.68%
Eye corrosion - 0.9737 97.37%
Eye irritation - 0.9528 95.28%
Skin irritation - 0.6443 64.43%
Skin corrosion - 0.8885 88.85%
Ames mutagenesis + 0.5200 52.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6203 62.03%
Micronuclear - 0.5600 56.00%
Hepatotoxicity + 0.6500 65.00%
skin sensitisation - 0.7542 75.42%
Respiratory toxicity + 0.6333 63.33%
Reproductive toxicity + 0.7000 70.00%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity + 0.7579 75.79%
Acute Oral Toxicity (c) III 0.4457 44.57%
Estrogen receptor binding + 0.7789 77.89%
Androgen receptor binding + 0.5966 59.66%
Thyroid receptor binding + 0.5982 59.82%
Glucocorticoid receptor binding + 0.6578 65.78%
Aromatase binding + 0.5715 57.15%
PPAR gamma + 0.5966 59.66%
Honey bee toxicity - 0.6673 66.73%
Biodegradation - 0.8750 87.50%
Crustacea aquatic toxicity + 0.5500 55.00%
Fish aquatic toxicity + 0.8979 89.79%

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 97.95% 91.11%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 95.95% 94.45%
CHEMBL221 P23219 Cyclooxygenase-1 95.50% 90.17%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.94% 95.56%
CHEMBL1293249 Q13887 Kruppel-like factor 5 91.21% 86.33%
CHEMBL253 P34972 Cannabinoid CB2 receptor 86.80% 97.25%
CHEMBL1806 P11388 DNA topoisomerase II alpha 86.42% 89.00%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 86.02% 96.09%
CHEMBL3401 O75469 Pregnane X receptor 85.85% 94.73%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 83.48% 94.00%
CHEMBL2007 P16234 Platelet-derived growth factor receptor alpha 82.33% 91.07%
CHEMBL3091268 Q92753 Nuclear receptor ROR-beta 82.04% 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.
Asteraceae

Cross-Links

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PubChem 5281446
NPASS NPC258711