Indomethacin

Details

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Internal ID 0639a437-53c9-467a-a09e-c29c48ef5145
Taxonomy Organoheterocyclic compounds > Indoles and derivatives > Benzoylindoles
IUPAC Name 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
SMILES (Canonical)
SMILES (Isomeric)
InChI InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)
InChI Key CGIGDMFJXJATDK-UHFFFAOYSA-N
Popularity 56,792 references in papers

Physical and Chemical Properties

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Molecular Formula C19H16ClNO4
Molecular Weight 357.80 g/mol
Exact Mass 357.0767857 g/mol
Topological Polar Surface Area (TPSA) 68.50 Ų
XlogP 4.30
Atomic LogP (AlogP) 3.93
H-Bond Acceptor 4
H-Bond Donor 1
Rotatable Bonds 4

Synonyms

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53-86-1
indometacin
Indocin
Indomethacine
Indometacine
Indocid
Reumacide
Indomethazine
Metindol
Artrinovo
There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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2D Structure of Indomethacin

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9868 98.68%
Caco-2 + 0.7305 73.05%
Blood Brain Barrier - 0.8500 85.00%
Human oral bioavailability + 0.9286 92.86%
Subcellular localzation Lysosomes 0.7419 74.19%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9414 94.14%
OATP1B3 inhibitior + 0.9376 93.76%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 1.0000 100.00%
BSEP inhibitior + 0.9071 90.71%
P-glycoprotein inhibitior - 0.9167 91.67%
P-glycoprotein substrate - 0.9362 93.62%
CYP3A4 substrate - 0.5332 53.32%
CYP2C9 substrate + 1.0000 100.00%
CYP2D6 substrate - 0.8985 89.85%
CYP3A4 inhibition - 0.8309 83.09%
CYP2C9 inhibition - 0.9071 90.71%
CYP2C19 inhibition - 0.9025 90.25%
CYP2D6 inhibition - 0.9302 93.02%
CYP1A2 inhibition + 0.9107 91.07%
CYP2C8 inhibition + 0.8544 85.44%
CYP inhibitory promiscuity + 0.6978 69.78%
UGT catelyzed - 0.0000 0.00%
Carcinogenicity (binary) - 0.7689 76.89%
Carcinogenicity (trinary) Danger 0.7450 74.50%
Eye corrosion - 0.9906 99.06%
Eye irritation - 0.9450 94.50%
Skin irritation - 0.8272 82.72%
Skin corrosion - 0.9467 94.67%
Ames mutagenesis - 0.8900 89.00%
Human Ether-a-go-go-Related Gene inhibition - 0.6287 62.87%
Micronuclear + 0.6759 67.59%
Hepatotoxicity + 0.8500 85.00%
skin sensitisation - 0.9044 90.44%
Respiratory toxicity + 0.8000 80.00%
Reproductive toxicity + 0.9889 98.89%
Mitochondrial toxicity + 0.8750 87.50%
Nephrotoxicity - 0.8145 81.45%
Acute Oral Toxicity (c) I 0.7774 77.74%
Estrogen receptor binding + 0.6763 67.63%
Androgen receptor binding - 0.5085 50.85%
Thyroid receptor binding - 0.7972 79.72%
Glucocorticoid receptor binding + 0.6895 68.95%
Aromatase binding - 0.7149 71.49%
PPAR gamma + 0.8707 87.07%
Honey bee toxicity - 0.9429 94.29%
Biodegradation - 0.9250 92.50%
Crustacea aquatic toxicity - 0.8053 80.53%
Fish aquatic toxicity + 0.9532 95.32%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
CHEMBL4681 P42330 Aldo-keto-reductase family 1 member C3 100 nM
IC50
via Super-PRED
CHEMBL1871 P10275 Androgen Receptor 0.14 nM
EC50
via Super-PRED
CHEMBL221 P23219 Cyclooxygenase-1 5 nM
IC50
via Super-PRED
CHEMBL5071 Q9Y5Y4 G protein-coupled receptor 44 50 nM
Ki
via Super-PRED
CHEMBL2157 P10145 Interleukin-8 50 nM
IC50
via Super-PRED
CHEMBL4523354 Q6XQN6 Nicotinate phosphoribosyltransferase 0.15 nM
Ki
via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID UniProt ID Name Probability Model accuracy
CHEMBL4208 P20618 Proteasome component C5 96.16% 90.00%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 95.60% 86.92%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 95.49% 96.09%
CHEMBL1293249 Q13887 Kruppel-like factor 5 94.60% 86.33%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 91.25% 95.56%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 90.42% 96.00%
CHEMBL4793 Q86TI2 Dipeptidyl peptidase IX 89.99% 96.95%
CHEMBL3401 O75469 Pregnane X receptor 89.81% 94.73%
CHEMBL2216739 Q92523 Carnitine O-palmitoyltransferase 1, muscle isoform 88.67% 88.33%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 88.58% 94.00%
CHEMBL3192 Q9BY41 Histone deacetylase 8 87.65% 93.99%
CHEMBL3060 Q9Y345 Glycine transporter 2 87.00% 99.17%
CHEMBL2581 P07339 Cathepsin D 86.94% 98.95%
CHEMBL2047 Q96RI1 Bile acid receptor FXR 85.13% 96.10%
CHEMBL2443 P49862 Kallikrein 7 85.12% 94.00%
CHEMBL1907 P15144 Aminopeptidase N 83.18% 93.31%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 82.52% 92.62%
CHEMBL204 P00734 Thrombin 82.48% 96.01%
CHEMBL1741221 Q9Y4P1 Cysteine protease ATG4B 82.07% 87.50%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 81.51% 100.00%
CHEMBL5852 Q96P65 Pyroglutamylated RFamide peptide receptor 81.03% 85.00%
CHEMBL4657 Q6V1X1 Dipeptidyl peptidase VIII 80.08% 97.21%

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.
Alpinia officinarum

Cross-Links

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PubChem 3715
LOTUS LTS0192710
wikiData Q409231