12-Oxophytodienoic acid

Details

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Internal ID 17784c25-fa3c-4c87-8976-5c4c11d209b1
Taxonomy Lipids and lipid-like molecules > Fatty Acyls > Eicosanoids > Prostaglandins and related compounds
IUPAC Name 8-[4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoic acid
SMILES (Canonical) CCC=CCC1C(C=CC1=O)CCCCCCCC(=O)O
SMILES (Isomeric) CC/C=C\CC1C(C=CC1=O)CCCCCCCC(=O)O
InChI InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-
InChI Key PMTMAFAPLCGXGK-CLTKARDFSA-N
Popularity 186 references in papers

Physical and Chemical Properties

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Molecular Formula C18H28O3
Molecular Weight 292.40 g/mol
Exact Mass 292.20384475 g/mol
Topological Polar Surface Area (TPSA) 54.40 Ų
XlogP 4.70
Atomic LogP (AlogP) 4.53
H-Bond Acceptor 2
H-Bond Donor 1
Rotatable Bonds 11

Synonyms

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12-Oxophytodienoic acid
12-Oxo-10,15(Z)-phytodienoic acid
CHEMBL465602
SCHEMBL14538124
8-[2-(cis-pent-2'-enyl)-3-oxo-cis-cyclopent-4-enyl]octanoic acid
8-[4-oxo-5-[(Z)-pent-2-enyl]cyclopent-2-en-1-yl]octanoic acid

2D Structure

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2D Structure of 12-Oxophytodienoic acid

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9874 98.74%
Caco-2 - 0.5368 53.68%
Blood Brain Barrier - 0.7500 75.00%
Human oral bioavailability - 0.6714 67.14%
Subcellular localzation Mitochondria 0.8761 87.61%
OATP2B1 inhibitior - 0.8532 85.32%
OATP1B1 inhibitior + 0.7794 77.94%
OATP1B3 inhibitior + 0.9444 94.44%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.6371 63.71%
P-glycoprotein inhibitior - 0.8387 83.87%
P-glycoprotein substrate - 0.7944 79.44%
CYP3A4 substrate - 0.5333 53.33%
CYP2C9 substrate - 0.7587 75.87%
CYP2D6 substrate - 0.9092 90.92%
CYP3A4 inhibition - 0.9339 93.39%
CYP2C9 inhibition - 0.9477 94.77%
CYP2C19 inhibition - 0.9237 92.37%
CYP2D6 inhibition - 0.9410 94.10%
CYP1A2 inhibition - 0.9410 94.10%
CYP2C8 inhibition - 0.8893 88.93%
CYP inhibitory promiscuity - 0.9699 96.99%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.9200 92.00%
Carcinogenicity (trinary) Non-required 0.6965 69.65%
Eye corrosion - 0.9673 96.73%
Eye irritation - 0.8405 84.05%
Skin irritation + 0.5506 55.06%
Skin corrosion - 0.8491 84.91%
Ames mutagenesis - 0.8428 84.28%
Human Ether-a-go-go-Related Gene inhibition - 0.3622 36.22%
Micronuclear - 0.8900 89.00%
Hepatotoxicity + 0.5125 51.25%
skin sensitisation - 0.6547 65.47%
Respiratory toxicity + 0.7111 71.11%
Reproductive toxicity + 0.7778 77.78%
Mitochondrial toxicity + 0.7125 71.25%
Nephrotoxicity - 0.8091 80.91%
Acute Oral Toxicity (c) III 0.7481 74.81%
Estrogen receptor binding + 0.6439 64.39%
Androgen receptor binding - 0.6768 67.68%
Thyroid receptor binding + 0.5544 55.44%
Glucocorticoid receptor binding - 0.5321 53.21%
Aromatase binding - 0.6425 64.25%
PPAR gamma + 0.5956 59.56%
Honey bee toxicity - 0.9672 96.72%
Biodegradation + 0.6000 60.00%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.9244 92.44%

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 95.16% 98.95%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.08% 96.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 93.60% 99.17%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 93.33% 91.11%
CHEMBL230 P35354 Cyclooxygenase-2 89.52% 89.63%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 88.48% 95.56%
CHEMBL1781 P11387 DNA topoisomerase I 84.14% 97.00%

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.
Arabidopsis thaliana
Linum usitatissimum

Cross-Links

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PubChem 10334541
LOTUS LTS0182831
wikiData Q105211729