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(5Z,8Z)-10-hydroxy-10-[(2R,3S)-3-[(Z)-oct-2-enyl]oxiran-2-yl]deca-5,8-dienoic acid

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 61363080-60f7-41dc-897c-97141b454c07
Taxonomy Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Hepoxilins
IUPAC Name (5Z,8Z)-10-hydroxy-10-[(2R,3S)-3-[(Z)-oct-2-enyl]oxiran-2-yl]deca-5,8-dienoic acid
SMILES (Canonical) CCCCCC=CCC1C(O1)C(C=CCC=CCCCC(=O)O)O
SMILES (Isomeric) CCCCC/C=C\C[C@H]1[C@H](O1)C(/C=C\C/C=C\CCCC(=O)O)O
InChI InChI=1S/C20H32O4/c1-2-3-4-5-9-12-15-18-20(24-18)17(21)14-11-8-6-7-10-13-16-19(22)23/h6-7,9,11-12,14,17-18,20-21H,2-5,8,10,13,15-16H2,1H3,(H,22,23)/b7-6-,12-9-,14-11-/t17?,18-,20+/m0/s1
InChI Key DWNBPRRXEVJMPO-YZTVQBIISA-N
Popularity 31 references in papers

Physical and Chemical Properties

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Molecular Formula C20H32O4
Molecular Weight 336.50 g/mol
Exact Mass 336.23005950 g/mol
Topological Polar Surface Area (TPSA) 70.10 Ų
XlogP 4.30
Atomic LogP (AlogP) 4.40
H-Bond Acceptor 3
H-Bond Donor 2
Rotatable Bonds 14

Synonyms

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(5Z,8Z)-10-hydroxy-10-[(2R,3S)-3-[(Z)-oct-2-enyl]oxiran-2-yl]deca-5,8-dienoic acid
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoate
10-hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoate
10-hydroxy-11R,12S-epoxy-5Z,8Z,14Z-eicosatrienoic acid
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoate
(5Z,8Z)-10-hydroxy-10-{(2R,3S)-3-[(2Z)-oct-2-en-1-yl]oxiran-2-yl}deca-5,8-dienoate
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoic acid
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyeicosa-5,8,14-trienoicacid
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoic acid
(5Z,8Z,14Z)-(11R,12S)-11,12-Epoxy-10-hydroxyicosa-5,8,14-trienoicacid
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of (5Z,8Z)-10-hydroxy-10-[(2R,3S)-3-[(Z)-oct-2-enyl]oxiran-2-yl]deca-5,8-dienoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9173 91.73%
Caco-2 - 0.7107 71.07%
Blood Brain Barrier - 0.5000 50.00%
Human oral bioavailability - 0.6571 65.71%
Subcellular localzation Mitochondria 0.5631 56.31%
OATP2B1 inhibitior - 0.8555 85.55%
OATP1B1 inhibitior - 0.5322 53.22%
OATP1B3 inhibitior + 0.9196 91.96%
MATE1 inhibitior - 1.0000 100.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior - 0.4531 45.31%
P-glycoprotein inhibitior - 0.6835 68.35%
P-glycoprotein substrate - 0.8683 86.83%
CYP3A4 substrate + 0.5200 52.00%
CYP2C9 substrate - 0.5928 59.28%
CYP2D6 substrate - 0.8557 85.57%
CYP3A4 inhibition - 0.6949 69.49%
CYP2C9 inhibition - 0.8516 85.16%
CYP2C19 inhibition - 0.6714 67.14%
CYP2D6 inhibition - 0.9248 92.48%
CYP1A2 inhibition - 0.6886 68.86%
CYP2C8 inhibition - 0.7648 76.48%
CYP inhibitory promiscuity - 0.9335 93.35%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.8815 88.15%
Carcinogenicity (trinary) Non-required 0.6769 67.69%
Eye corrosion - 0.9550 95.50%
Eye irritation - 0.8616 86.16%
Skin irritation + 0.5252 52.52%
Skin corrosion - 0.8581 85.81%
Ames mutagenesis - 0.7700 77.00%
Human Ether-a-go-go-Related Gene inhibition - 0.3939 39.39%
Micronuclear - 0.7500 75.00%
Hepatotoxicity - 0.6696 66.96%
skin sensitisation - 0.7853 78.53%
Respiratory toxicity + 0.6222 62.22%
Reproductive toxicity - 0.6323 63.23%
Mitochondrial toxicity + 0.6125 61.25%
Nephrotoxicity - 0.8041 80.41%
Acute Oral Toxicity (c) III 0.5122 51.22%
Estrogen receptor binding + 0.6264 62.64%
Androgen receptor binding - 0.8529 85.29%
Thyroid receptor binding - 0.6341 63.41%
Glucocorticoid receptor binding - 0.5246 52.46%
Aromatase binding - 0.7302 73.02%
PPAR gamma + 0.6945 69.45%
Honey bee toxicity - 0.9550 95.50%
Biodegradation - 0.6250 62.50%
Crustacea aquatic toxicity + 0.5100 51.00%
Fish aquatic toxicity + 0.9541 95.41%

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
CHEMBL2581 P07339 Cathepsin D 97.89% 98.95%
CHEMBL3060 Q9Y345 Glycine transporter 2 97.79% 99.17%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 93.94% 96.09%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 92.36% 94.45%
CHEMBL253 P34972 Cannabinoid CB2 receptor 91.61% 97.25%
CHEMBL1781 P11387 DNA topoisomerase I 91.21% 97.00%
CHEMBL4769 O95749 Geranylgeranyl pyrophosphate synthetase 90.27% 92.08%
CHEMBL221 P23219 Cyclooxygenase-1 88.23% 90.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 87.98% 91.11%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 87.84% 96.95%
CHEMBL3401 O75469 Pregnane X receptor 85.62% 94.73%
CHEMBL3359 P21462 Formyl peptide receptor 1 84.65% 93.56%
CHEMBL2001 Q9H244 Purinergic receptor P2Y12 83.45% 96.00%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 83.14% 97.21%
CHEMBL1881 P43116 Prostanoid EP2 receptor 81.04% 93.00%
CHEMBL4227 P25090 Lipoxin A4 receptor 80.76% 100.00%

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 5283209
LOTUS LTS0011979
wikiData Q105104574