1H-Benzoimidazole-2-carboxylic acid {1-[1-cyclohexylmethyl-2-hydroxy-4-(2-morpholin-4-yl-ethylcarbamoyl)-hept-6-ynylcarbamoyl]-2-methylsulfanyl-ethyl}-amide

ID: ALA83697

PubChem CID: 10484275

Max Phase: Preclinical

Molecular Formula: C33H48N6O5S

Molecular Weight: 640.85

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CC[C@H](C[C@H](O)[C@H](CC1CCCCC1)NC(=O)[C@H](CSC)NC(=O)c1nc2ccccc2[nH]1)C(=O)NCCN1CCOCC1

Standard InChI:  InChI=1S/C33H48N6O5S/c1-3-9-24(31(41)34-14-15-39-16-18-44-19-17-39)21-29(40)27(20-23-10-5-4-6-11-23)37-32(42)28(22-45-2)38-33(43)30-35-25-12-7-8-13-26(25)36-30/h1,7-8,12-13,23-24,27-29,40H,4-6,9-11,14-22H2,2H3,(H,34,41)(H,35,36)(H,37,42)(H,38,43)/t24-,27+,28+,29+/m1/s1

Standard InChI Key:  MDCNERSXJOKFTF-KHUDPXOFSA-N

Molfile:  

     RDKit          2D

 45 48  0  0  1  0  0  0  0  0999 V2000
    1.7625   -2.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2667   -2.2542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2792   -3.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -2.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -3.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1667   -3.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9667   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -3.2792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4792   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4875   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9625   -3.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -3.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8250   -1.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4042   -1.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5292   -3.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8167   -3.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -3.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9000   -2.1542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -4.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -4.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9667   -4.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6667   -3.2750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.2500   -4.4792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2417   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9625   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -2.0417    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -2.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3917   -3.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1042   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8042   -4.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8250   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5292   -3.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2333   -3.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2417   -3.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5375   -4.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -1.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -5.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -4.5292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9458   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9458   -3.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -4.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5042   -6.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2250   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5  7  1  0
  6  4  1  0
  7  6  1  0
  8  5  1  0
  9  2  1  0
 10  3  1  0
 11 18  1  0
 12  8  1  0
 13 25  1  0
 14 13  3  0
 15 17  1  0
 16 30  1  0
 17 12  1  0
 18 15  1  0
 19  4  2  0
 20  5  2  0
 12 21  1  6
 22 11  2  0
 23 11  1  0
 24 36  1  0
 18 25  1  1
  7 26  1  1
 27 26  1  0
 17 28  1  1
 29 23  1  0
 30 29  1  0
 31 21  1  0
 32 16  1  0
 33 16  1  0
 34  9  2  0
 35 10  2  0
 36 33  1  0
 37 32  1  0
 27 38  1  0
 39 31  1  0
 40 31  1  0
 41 34  1  0
 42 35  1  0
 43 40  1  0
 44 39  1  0
 45 43  1  0
 10  9  1  0
 42 41  2  0
 44 45  1  0
 24 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA83697

   N-[(2R)-1-[[(2S,3S,5R)-1-cyclohexyl-3-hydroxy-5-(2-morpholin-4-ylethylcarbamoyl)oct-7-yn-2-yl]amino]-3-methylsulfanyl-1-oxopropan-2-yl]-1H-benzimidazole-2-carboxamide

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: 640.85

Molecular Weight (Monoisotopic): 640.3407

AlogP: 2.32

#Rotatable Bonds: 16

Polar Surface Area: 148.68

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.66

CX Basic pKa: 6.11

CX LogP: 2.37

CX LogD: 2.34

Aromatic Rings: 2

Heavy Atoms: 45

QED Weighted: 0.18

Np Likeness Score: -0.65

References

1. Cozzini P, Fornabaio M, Marabotti A, Abraham DJ, Kellogg GE, Mozzarelli A..  (2002)  Simple, intuitive calculations of free energy of binding for protein-ligand complexes. 1. Models without explicit constrained water.,  45  (12): [PMID:12036355] [10.1021/jm0200299]

Source

Source(1):

• Scientific Literature