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3-(Benzyloxy)-1-methyl-5-(phenoxymethyl)-1H-pyrazole-4-carboxylic acid
ID: ALA4568957
PubChem CID: 155550265
Max Phase: Preclinical
Molecular Formula: C19H18N2O4
Molecular Weight: 338.36
Molecule Type: Unknown
Associated Items:
Names and Identifiers
Canonical SMILES: Cn1nc(OCc2ccccc2)c(C(=O)O)c1COc1ccccc1
Standard InChI: InChI=1S/C19H18N2O4/c1-21-16(13-24-15-10-6-3-7-11-15)17(19(22)23)18(20-21)25-12-14-8-4-2-5-9-14/h2-11H,12-13H2,1H3,(H,22,23)
Standard InChI Key: KMOSZQGZQBTOIZ-UHFFFAOYSA-N
Molfile:
RDKit 2D
25 27 0 0 0 0 0 0 0 0999 V2000
38.3675 -18.6225 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
39.0305 -18.1446 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
38.7761 -17.3637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
37.9589 -17.3637 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
37.7046 -18.1446 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
39.4823 -16.9525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
39.4792 -16.1353 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
38.3675 -19.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
37.4788 -16.7024 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
40.1915 -17.3584 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
39.7328 -18.5519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
39.7312 -19.3691 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
40.4382 -19.7790 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
40.4342 -20.5959 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
41.1403 -21.0058 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
41.8498 -20.5985 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
41.8488 -19.7771 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
41.1421 -19.3709 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
36.6580 -16.6946 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
36.2562 -15.9831 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
36.6754 -15.2832 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
36.2742 -14.5721 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
35.4562 -14.5639 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
35.0410 -15.2727 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
35.4446 -15.9809 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
4 5 2 0
2 3 2 0
1 2 1 0
3 4 1 0
5 1 1 0
3 6 1 0
6 7 2 0
1 8 1 0
4 9 1 0
6 10 1 0
2 11 1 0
11 12 1 0
12 13 1 0
13 14 2 0
14 15 1 0
15 16 2 0
16 17 1 0
17 18 2 0
18 13 1 0
9 19 1 0
19 20 1 0
20 21 2 0
21 22 1 0
22 23 2 0
23 24 1 0
24 25 2 0
25 20 1 0
M END
Associated Targets(Human)
Associated Targets(non-human)
Molecule Features
Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
Molecule Type: Unknown | Topical: No | First In Class: No | Black Box: No |
Chirality: No | Availability: No | Prodrug: No |
Drug Indications
MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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Calculated Properties
Molecular Weight: 338.36 | Molecular Weight (Monoisotopic): 338.1267 | AlogP: 3.28 | #Rotatable Bonds: 7 |
Polar Surface Area: 73.58 | Molecular Species: ACID | HBA: 5 | HBD: 1 |
#RO5 Violations: ┄ | HBA (Lipinski): 6 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): ┄ |
CX Acidic pKa: 4.02 | CX Basic pKa: ┄ | CX LogP: 3.71 | CX LogD: 0.56 |
Aromatic Rings: 3 | Heavy Atoms: 25 | QED Weighted: 0.72 | Np Likeness Score: -0.72 |
References
1. Pippione AC, Sainas S, Goyal P, Fritzson I, Cassiano GC, Giraudo A, Giorgis M, Tavella TA, Bagnati R, Rolando B, Caing-Carlsson R, Costa FTM, Andrade CH, Al-Karadaghi S, Boschi D, Friemann R, Lolli ML.. (2019) Hydroxyazole scaffold-based Plasmodium falciparum dihydroorotate dehydrogenase inhibitors: Synthesis, biological evaluation and X-ray structural studies., 163 [PMID:30529545] [10.1016/j.ejmech.2018.11.044] |