2-(5-{[(2S)-2-Amino-4-methylpentyl]oxy}pyridin-3-yl)-8,9-dimethoxybenzo[c]-2,7-naphthyridin-4-amine

ID: ALA1094321

PubChem CID: 46192859

Max Phase: Preclinical

Molecular Formula: C25H29N5O3

Molecular Weight: 447.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc2ncc3c(N)nc(-c4cncc(OC[C@@H](N)CC(C)C)c4)cc3c2cc1OC

Standard InChI:  InChI=1S/C25H29N5O3/c1-14(2)5-16(26)13-33-17-6-15(10-28-11-17)21-7-18-19-8-23(31-3)24(32-4)9-22(19)29-12-20(18)25(27)30-21/h6-12,14,16H,5,13,26H2,1-4H3,(H2,27,30)/t16-/m0/s1

Standard InChI Key:  YPVWKNICBVIRFI-INIZCTEOSA-N

Molfile:  

     RDKit          2D

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    0.1696  -23.1503    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.6044  -22.3360    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730  -26.8748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5871  -27.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8746  -28.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  5  9  1  0
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 31 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1094321

   2-(5-{[(2S)-2-Amino-4-methylpentyl]oxy}pyridin-3-yl)-8,9-dimethoxybenzo[c]-2,7-naphthyridin-4-amine

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

Calculated Properties

Molecular Weight: 447.54

Molecular Weight (Monoisotopic): 447.2270

AlogP: 4.20

#Rotatable Bonds: 8

Polar Surface Area: 118.40

Molecular Species: BASE

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.55

CX LogP: 2.88

CX LogD: 0.76

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.39

Np Likeness Score: -0.39

References

1. Nittoli T, Dushin RG, Ingalls C, Cheung K, Floyd MB, Fraser H, Olland A, Hu Y, Grosu G, Han X, Arndt K, Guo B, Wissner A..  (2010)  The identification of 8,9-dimethoxy-5-(2-aminoalkoxy-pyridin-3-yl)-benzo[c][2,7]naphthyridin-4-ylamines as potent inhibitors of 3-phosphoinositide-dependent kinase-1 (PDK-1).,  45  (4): [PMID:20074837] [10.1016/j.ejmech.2009.12.036]

Source

Source(1):

• Scientific Literature