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3-Phenyl-5-(3,4-dihydroxyphenyl)-1H-pyrrolo[2,3-b]pyridine
ID: ALA3102942
PubChem CID: 72792829
Max Phase: Preclinical
Molecular Formula: C19H14N2O2
Molecular Weight: 302.33
Molecule Type: Small molecule
Associated Items:
Names and Identifiers
Canonical SMILES: Oc1ccc(-c2cnc3[nH]cc(-c4ccccc4)c3c2)cc1O
Standard InChI: InChI=1S/C19H14N2O2/c22-17-7-6-13(9-18(17)23)14-8-15-16(11-21-19(15)20-10-14)12-4-2-1-3-5-12/h1-11,22-23H,(H,20,21)
Standard InChI Key: OVGOMELIPUOQHV-UHFFFAOYSA-N
Molfile:
RDKit 2D
23 26 0 0 0 0 0 0 0 0999 V2000
27.6161 -15.0042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
27.6150 -15.8315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
28.3296 -16.2442 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
28.3278 -14.5916 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
26.9018 -14.5920 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
29.0430 -15.0006 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
29.0433 -15.8315 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
29.8335 -16.0880 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0
30.3217 -15.4157 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
29.8331 -14.7437 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
30.2209 -14.0167 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
31.0460 -13.9917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
31.4341 -13.2648 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
30.9980 -12.5638 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
30.1695 -12.5943 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
29.7850 -13.3215 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
26.9050 -13.7663 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
26.1915 -13.3541 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
25.4763 -13.7668 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
25.4792 -14.5958 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
26.1933 -15.0042 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0
24.7664 -15.0108 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
24.7614 -13.3555 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0
1 2 2 0
2 3 1 0
3 7 2 0
6 4 2 0
4 1 1 0
1 5 1 0
6 7 1 0
7 8 1 0
8 9 1 0
9 10 2 0
10 6 1 0
10 11 1 0
11 12 2 0
12 13 1 0
13 14 2 0
14 15 1 0
15 16 2 0
16 11 1 0
5 17 2 0
17 18 1 0
18 19 2 0
19 20 1 0
20 21 2 0
21 5 1 0
20 22 1 0
19 23 1 0
M END
Associated Targets(non-human)
Molecule Features
Natural Product: No | Oral: No | Chemical Probe: No | Parenteral: No |
Molecule Type: Small molecule | 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: 302.33 | Molecular Weight (Monoisotopic): 302.1055 | AlogP: 4.31 | #Rotatable Bonds: 2 |
Polar Surface Area: 69.14 | Molecular Species: NEUTRAL | HBA: 3 | HBD: 3 |
#RO5 Violations: ┄ | HBA (Lipinski): 4 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): ┄ |
CX Acidic pKa: 9.16 | CX Basic pKa: 2.96 | CX LogP: 3.91 | CX LogD: 3.90 |
Aromatic Rings: 4 | Heavy Atoms: 23 | QED Weighted: 0.48 | Np Likeness Score: 0.03 |
References
1. Gourdain S, Dairou J, Denhez C, Bui LC, Rodrigues-Lima F, Janel N, Delabar JM, Cariou K, Dodd RH.. (2013) Development of DANDYs, new 3,5-diaryl-7-azaindoles demonstrating potent DYRK1A kinase inhibitory activity., 56 (23): [PMID:24188002] [10.1021/jm401049v] |