Molecule

7-Amino-4-(trifluoromethyl)coumarin

AlkaPlorer ID: AK418781

Synonym: None

IUPAC Name: 7-amino-4-(trifluoromethyl)chromen-2-one

Structure

SMILES: NC1=CC=C2C(C(F)(F)F)=CC(=O)OC2=C1

InChI: InChI=1S/C10H6F3NO2/c11-10(12,13)7-4-9(15)16-8-3-5(14)1-2-6(7)8/h1-4H,14H2

InChIKey: JBNOVHJXQSHGRL-UHFFFAOYSA-N

Reference

Constituents of Brazilian red propolis and their preferential cytotoxic activity against human pancreatic PANC-1 cancer cell line in nutrient-deprived condition

Cytotoxic constituents from Brazilian red propolis and their structure–activity relationship

(±)-Acortatarinowins A–F, Norlignan, Neolignan, and Lignan Enantiomers from <i>Acorus tatarinowii</i>

In vitro anti-inflammatory activity of lignans isolated from Magnolia fargesii

PubChem CID: 100641

CAS: 53473-36-2

Source

Species	Genus	Family	Order	Class	Phylum	Kingdom	Domain

Properties Information

Molecule Weight: 229.157

TPSA？: 56.23

MolLogP？: 2.394

Number of H-Donors: 1

Number of H-Acceptors: 3

RingCount: 2

Activities Information

Organism	Target Name	Standard Type	Standard Value	Standard Units	doi
Bacillus anthracis	Anthrax lethal factor	Potency	12589.3	nM	None
Bacillus subtilis (strain 168)	ATP-dependent Clp protease proteolytic subunit	Potency	39810.7	nM	None
Cricetulus griseus	CHO	IC50	49704.0	nM	None
Equus caballus	Ferritin light chain	Potency	14125.4	nM	None
Homo sapiens	15-hydroxyprostaglandin dehydrogenase [NAD+]	Potency	28183.8	nM	None
Homo sapiens	A549	Activity	nan	None	10.1021/acs.jnatprod.7b00665
Homo sapiens	Aldehyde dehydrogenase 1A1	Potency	25118.9	nM	None
Homo sapiens	Ataxin-2	Potency	39810.7	nM	None
Homo sapiens	Caspase-1	Potency	3981.1	nM	None
Homo sapiens	Caspase-7	Potency	3981.1	nM	None
Homo sapiens	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Potency	25118.9	nM	None
Homo sapiens	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	Potency	39810.7	nM	None
Homo sapiens	Geminin	Potency	25929.0	nM	None
Homo sapiens	GTP-binding nuclear protein Ran/Importin subunit beta-1/Snurportin-1	Potency	56234.1	nM	None
Homo sapiens	Guanine nucleotide-binding protein G(s), subunit alpha	Potency	22387.2	nM	None
Homo sapiens	Histone acetyltransferase GCN5	Potency	19952.6	nM	None
Homo sapiens	Importin subunit beta-1/Snurportin-1	Potency	100000.0	nM	None
Homo sapiens	Lysine-specific demethylase 4A	Potency	89125.1	nM	None
Homo sapiens	Lysine-specific demethylase 4D-like	Potency	31622.8	nM	None
Homo sapiens	Lysosomal alpha-glucosidase	Potency	15848.9	nM	None
Homo sapiens	Menin/Histone-lysine N-methyltransferase MLL	Potency	15848.9	nM	None
Homo sapiens	Muscleblind-like protein 1	Potency	707.9	nM	None
Homo sapiens	Neuropeptide S receptor	Potency	12589.3	nM	None
Homo sapiens	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Potency	67455.5	nM	None
Homo sapiens	Serine-protein kinase ATM	Potency	17782.8	nM	None
Homo sapiens	SK-MEL-28	IC50	980.0	nM	10.1021/acsmedchemlett.3c00019
Homo sapiens	SK-MEL3	IC50	930.0	nM	10.1021/acsmedchemlett.3c00019
Homo sapiens	Toll-like receptor 9	IC50	8421.0	nM	None
Homo sapiens	Tyrosine-protein kinase SRC	IC50	30900.0	nM	10.1016/j.ejmech.2015.07.010
Influenza A virus	Influenza A virus	Activity	nan	None	10.1021/acs.jnatprod.7b00665
Influenza A virus	Influenza A virus	IC50	51.0	ug.mL-1	10.1021/acs.jnatprod.7b00665
Mus musculus	Myelin basic protein	Activity	nan	None	10.1021/jm101489w
Plasmodium falciparum	Plasmodium falciparum	Potency	18526.0	nM	None
Pseudomonas aeruginosa	Beta Lactamase	IC50	4768.0	nM	None
Rattus norvegicus	Inositol monophosphatase 1	Potency	12589.3	nM	None
Rattus norvegicus	Inositol monophosphatase 1	Potency	31622.8	nM	None
Rattus norvegicus	Thioredoxin reductase 1, cytoplasmic	Potency	56234.1	nM	None
None	ADMET	Drug uptake	nan	None	10.1021/acsmedchemlett.3c00019
None	Unchecked	IC50	27400.0	nM	10.1021/acsmedchemlett.3c00019
None	Unchecked	Potency	3981.1	nM	None
None	Unchecked	Potency	28183.8	nM	None
None	Unchecked	Potency	29092.9	nM	None
None	Unchecked	Ratio IC50	29.4	None	10.1021/acsmedchemlett.3c00019

Metabolism Information

AKRT ID	Reaction	Reaction Link ID
AKRT002297	CC(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)C(C)C>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73210
AKRT002573	CC(=O)N[C@@H](CC(=O)O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)C(C)C>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_72811
AKRT002578	CC(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)C(C)C>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73043
AKRT002587	CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](Cc1ccc(O)cc1)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73025
AKRT002588	CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73253
AKRT002589	CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)C(C)C>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73120
AKRT002590	CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)[C@@H](C)O>>CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)O)[C@@H](C)O.Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	None
AKRT002591	CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)[C@@H](C)O>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73232
AKRT002592	CC(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CO)C(=O)N[C@H](C(=O)N[C@H](C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)[C@@H](C)O)[C@@H](C)O>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_72378
AKRT002758	CC(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_72669
AKRT002779	CC(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_71964
AKRT005674	CC(C)C[C@H](N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)C(C)C>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73109
AKRT005720	CC(C)C[C@H](N)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_64710
AKRT005894	CC(C)C[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73004
AKRT006099	CC(C)C[C@H](NC(=O)[C@H](N)C(C)C)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_69536
AKRT006213	CC(C)[C@H](N)C(=O)N[C@@H](CC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](C)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)C(C)C>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73041
AKRT006397	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](N)CC(=O)O)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73068
AKRT006399	CC(C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@H](N)CC(=O)O)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73045
AKRT009931	CC[C@H](C)[C@H](N)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)[C@@H](C)O>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73132
AKRT010058	CC[C@H](C)[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)[C@@H](C)O>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73227
AKRT010102	CC[C@H](C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](N)C(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73157
AKRT010113	CC[C@H](C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](NC(C)=O)C(C)C)C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73131
AKRT010159	CC[C@H](C)[C@H](NC(C)=O)C(=O)N[C@@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@@H](CC(=O)O)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)[C@@H](C)O>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_73231
AKRT013400	C[C@H](N)C(=O)N1CCC[C@H]1C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>C[C@H](N)C(=O)N1CCC[C@H]1C(=O)O.Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	None
AKRT013402	C[C@H](N)C(=O)N1CCC[C@H]1C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_66841
AKRT013512	C[C@H](N)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_64711
AKRT013779	C[C@H](NC(=O)[C@@H]1CCCN1)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_66964
AKRT015933	N=C(N)NCCC[C@@H](N)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_64712
AKRT016007	N=C(N)NCCC[C@H](N)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_71976
AKRT016121	N=C(N)NCCC[C@H](NC(=O)CNC(=O)CNC(=O)OCc1ccccc1)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_70800
AKRT016125	N=C(N)NCCC[C@H](NC(=O)CNC(=O)OCc1ccccc1)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_70327
AKRT016139	N=C(N)NCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>N=C(N)NCCC[C@H](NC(=O)[C@H](CCCNC(=N)N)NC(=O)OCc1ccccc1)C(=O)O.Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	None
AKRT016140	N=C(N)NCCC[C@H](NC(=O)OCc1ccccc1)C(=O)N[C@@H](CCCNC(=N)N)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_71778
AKRT016173	N=C(N)NCCC[C@H](NC(=O)[C@H](CCCCN)NC(=O)OCc1ccccc1)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_70328
AKRT016189	N=C(N)NCCC[C@H](NC(=O)[C@H](Cc1ccccc1)NC(=O)OCc1ccccc1)C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_71946
AKRT017514	NCC(=O)N1CCC[C@H]1C(=O)Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_66576
AKRT022537	O=C(Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1)[C@@H]1CCCN1>>Nc1ccc2c(C(F)(F)F)cc(=O)oc2c1	enzymemap_66576