2-((2R,4S)-4-((2S,3S)-2-(Dimethylamino)-3-methylpentanamido)tetrahydro-2H-pyran-2-yl)-N-isopropylthiazole-4-carboxamide

ID: ALA3628393

PubChem CID: 122193420

Max Phase: Preclinical

Molecular Formula: C20H34N4O3S

Molecular Weight: 410.58

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@@H](C(=O)N[C@H]1CCO[C@@H](c2nc(C(=O)NC(C)C)cs2)C1)N(C)C

Standard InChI:  InChI=1S/C20H34N4O3S/c1-7-13(4)17(24(5)6)19(26)22-14-8-9-27-16(10-14)20-23-15(11-28-20)18(25)21-12(2)3/h11-14,16-17H,7-10H2,1-6H3,(H,21,25)(H,22,26)/t13-,14-,16+,17-/m0/s1

Standard InChI Key:  IGAUSBJRGBDGDA-DIECFANBSA-N

Molfile:  

     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
    5.1959   -3.0115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -5.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1894   -6.0109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1877   -7.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5548   -3.6021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2122    3.8625    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7464    5.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7536    5.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2149    3.8587    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6387    6.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1543    7.5928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308    6.3335    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174    7.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2104    7.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5330    8.6423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2333   -3.6148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2001   -1.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  2  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  0
  3  8  2  0
  3  9  1  0
 10  9  1  1
 10 11  1  0
 10 15  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 12 16  1  1
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  2  0
 19 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 24 26  1  0
  1 27  1  0
  1 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3628393

   ---

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: 410.58

Molecular Weight (Monoisotopic): 410.2352

AlogP: 2.59

#Rotatable Bonds: 8

Polar Surface Area: 83.56

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.36

CX LogP: 1.85

CX LogD: 0.85

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.69

Np Likeness Score: -0.49

References

1. Park Y, Bae SY, Hah JM, Lee SK, Ryu JS..  (2015)  Synthesis of stereochemically diverse cyclic analogs of tubulysins.,  23  (21): [PMID:26474666] [10.1016/j.bmc.2015.10.003]

Source

Source(1):

• Scientific Literature