rac-methyl 3-(2-methoxyacetamido)-1-methyl-5-(6-methylhept-5-en-2-ylamino)-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

ID: ALA3234419

PubChem CID: 45161404

Max Phase: Preclinical

Molecular Formula: C21H30N4O4

Molecular Weight: 402.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCC(=O)Nc1c(C(=O)OC)n(C)c2ncc(NC(C)CCC=C(C)C)cc12

Standard InChI:  InChI=1S/C21H30N4O4/c1-13(2)8-7-9-14(3)23-15-10-16-18(24-17(26)12-28-5)19(21(27)29-6)25(4)20(16)22-11-15/h8,10-11,14,23H,7,9,12H2,1-6H3,(H,24,26)

Standard InChI Key:  PAJCVNRETJKNMJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    8.6279   -3.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8013   -3.8696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4187   -4.6012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0702   -4.5298    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6916   -5.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8659   -5.2989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6461   -6.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3359   -6.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9812   -6.0363    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6914   -6.4560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3596   -3.1728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7422   -2.4419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3006   -1.7451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5665   -2.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4763   -1.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0937   -2.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2694   -2.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8867   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8277   -1.8472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9280   -6.5007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2178   -6.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4991   -6.4858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2264   -5.2558    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4906   -7.3107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7719   -7.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3730   -7.3751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6778   -7.8193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7148   -8.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1053   -7.7551    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
  9 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
  7 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  2  0
 22 24  1  0
 24 25  1  0
  8 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3234419

   Methyl 3-[(2-methoxyacetyl)amino]-1-methyl-5-(6-methylhept-5-en-2-ylamino)pyrrolo[2,3-b]pyridine-2-carboxylate

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: 402.50

Molecular Weight (Monoisotopic): 402.2267

AlogP: 3.49

#Rotatable Bonds: 9

Polar Surface Area: 94.48

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.91

CX Basic pKa: 3.60

CX LogP: 3.07

CX LogD: 3.07

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -0.79

References

1. Wang T, Bisson WH, Mäser P, Scapozza L, Picard D..  (2014)  Differences in conformational dynamics between Plasmodium falciparum and human Hsp90 orthologues enable the structure-based discovery of pathogen-selective inhibitors.,  57  (6): [PMID:24580531] [10.1021/jm401801t]

Source

Source(1):

• Scientific Literature