4-(4-((5-(4,5-dimethyl-2-nitrophenyl)furan-2-yl)methylene)-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl)benzoic acid

ID: ALA1797936

Chembl Id: CHEMBL1797936

Max Phase: Preclinical

Molecular Formula: C24H19N3O6

Molecular Weight: 445.43

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  CC1=NN(c2ccc(C(=O)O)cc2)C(=O)/C1=C\c1ccc(-c2cc(C)c(C)cc2[N+](=O)[O-])o1

Standard InChI:  InChI=1S/C24H19N3O6/c1-13-10-20(21(27(31)32)11-14(13)2)22-9-8-18(33-22)12-19-15(3)25-26(23(19)28)17-6-4-16(5-7-17)24(29)30/h4-12H,1-3H3,(H,29,30)/b19-12-

Standard InChI Key:  HEKJYZZSCQBJGB-UNOMPAQXSA-N

Alternative Forms

  1. Parent:

    ALA1797936

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Associated Targets(Human)

EP300 Tchem Histone acetyltransferase p300 (1259 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KAT2B Tchem Histone acetyltransferase PCAF (884 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KAT6A Tchem Histone acetyltransferase KAT6A (320 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MCF7 (126967 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
T47D (39041 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
HDAC6 Tclin Histone deacetylase 6 (20808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CREBBP Tchem CREB-binding protein (1602 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KAT5 Tchem Histone acetyltransferase KAT5 (85 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KAT7 Tbio Histone acetyltransferase KAT7 (12 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KAT6B Tchem Histone acetyltransferase KAT6B (12 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
KAT2A Tchem Histone acetyltransferase GCN5 (14285 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Tubulin (1327 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Plasmodium falciparum (966862 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 445.43Molecular Weight (Monoisotopic): 445.1274AlogP: 4.98#Rotatable Bonds: 5
Polar Surface Area: 126.25Molecular Species: ACIDHBA: 6HBD: 1
#RO5 Violations: HBA (Lipinski): 9HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 3.98CX Basic pKa: CX LogP: 4.83CX LogD: 1.66
Aromatic Rings: 3Heavy Atoms: 33QED Weighted: 0.34Np Likeness Score: -1.30

References

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3. Simon RP, Robaa D, Alhalabi Z, Sippl W, Jung M..  (2016)  KATching-Up on Small Molecule Modulators of Lysine Acetyltransferases.,  59  (4): [PMID:26701186] [10.1021/acs.jmedchem.5b01502]
4. Shrimp JH, Sorum AW, Garlick JM, Guasch L, Nicklaus MC, Meier JL..  (2016)  Characterizing the Covalent Targets of a Small Molecule Inhibitor of the Lysine Acetyltransferase P300.,  (2): [PMID:26985290] [10.1021/acsmedchemlett.5b00385]
5. Yang Y, Zhang R, Li Z, Mei L, Wan S, Ding H, Chen Z, Xing J, Feng H, Han J, Jiang H, Zheng M, Luo C, Zhou B..  (2020)  Discovery of Highly Potent, Selective, and Orally Efficacious p300/CBP Histone Acetyltransferases Inhibitors.,  63  (3): [PMID:31910017] [10.1021/acs.jmedchem.9b01721]
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8. Liu R, Zhang Z, Yang H, Zhou K, Geng M, Zhou W, Zhang M, Huang X, Li Y..  (2019)  Design, synthesis, and biological evaluation of a new class of histone acetyltransferase p300 inhibitors.,  180  [PMID:31306905] [10.1016/j.ejmech.2019.07.026]
9. He ZX,Wei BF,Zhang X,Gong YP,Ma LY,Zhao W.  (2021)  Current development of CBP/p300 inhibitors in the last decade.,  209  [PMID:33045661] [10.1016/j.ejmech.2020.112861]
10. Bernhard Ellinger, Justus Dick, Vanessa Lage-Rupprecht, Bruce Schultz, Andrea Zaliani, Marcin Namysl, Stephan Gebel, Ole Pless, Jeanette Reinshagen, Christian Ebeling, Alexander Esser, Marc Jacobs, Carsten Claussen, and Martin Hofmann-Apitius.  (2021)  HDAC6 screening dataset using tau-based substrate in an enzymatic assay yields selective inhibitors and activators,  [10.6019/CHEMBL4808148]
11. Kanada R, Suzuki T, Murata T, Miyazaki M, Shimada T, Kuroha M, Minami M, Higuchi S, Tominaga Y, Naito H..  (2021)  4-Pyridone-3-carboxylic acid as a benzoic acid bioisostere: Design, synthesis, and evaluation of EP300/CBP histone acetyltransferase inhibitors.,  51  [PMID:34534674] [10.1016/j.bmcl.2021.128358]
12. Nie S, Wu F, Wu J, Li X, Zhou C, Yao Y, Song Y..  (2022)  Structure-activity relationship and antitumor activity of 1,4-pyrazine-containing inhibitors of histone acetyltransferases P300/CBP.,  237  [PMID:35512565] [10.1016/j.ejmech.2022.114407]
13. Wang L, Bharti, Kumar R, Pavlov PF, Winblad B..  (2021)  Small molecule therapeutics for tauopathy in Alzheimer's disease: Walking on the path of most resistance.,  209  [PMID:33139110] [10.1016/j.ejmech.2020.112915]
14. Kanada R, Kagoshima Y, Asano M, Suzuki T, Murata T, Haruta M, Takahashi M, Ubukata O, Hashimoto K, Obata K, Kihara K, Kuroha M, Banjo T, Togashi N, Sato K, Yamamoto Y, Suzuki K, Isoyama T, Tominaga Y, Higuchi S, Naito H..  (2022)  Discovery of EP300/CBP histone acetyltransferase inhibitors through scaffold hopping of 1,4-oxazepane ring.,  66  [PMID:35413416] [10.1016/j.bmcl.2022.128726]