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

ID: ALA3628394

PubChem CID: 122193421

Max Phase: Preclinical

Molecular Formula: C27H39N5O4S

Molecular Weight: 529.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC[C@H](C)[C@H](NC(=O)CN(C)C)C(=O)N[C@H]1CCO[C@@H](c2nc(C(=O)NCCc3ccccc3)cs2)C1

Standard InChI:  InChI=1S/C27H39N5O4S/c1-5-18(2)24(31-23(33)16-32(3)4)26(35)29-20-12-14-36-22(15-20)27-30-21(17-37-27)25(34)28-13-11-19-9-7-6-8-10-19/h6-10,17-18,20,22,24H,5,11-16H2,1-4H3,(H,28,34)(H,29,35)(H,31,33)/t18-,20-,22+,24-/m0/s1

Standard InChI Key:  BFJOYFRPRSLZTN-UXEORXRVSA-N

Molfile:  

     RDKit          2D

 37 39  0  0  0  0  0  0  0  0999 V2000
    3.8912   -5.2578    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
    5.1929   -3.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2321   -3.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1933   -1.5053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2324   -0.9050    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
    5.5095    7.3831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3961    8.5940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8877    8.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7713    9.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1634   11.0183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6719   11.1775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7883    9.9654    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
    5.1873   -7.5117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2297   -5.4127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4855   -8.2648    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4838   -9.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5257   -7.6666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  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
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
  1 32  1  0
 32 33  1  0
 32 34  2  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3628394

   ---

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: 529.71

Molecular Weight (Monoisotopic): 529.2723

AlogP: 2.54

#Rotatable Bonds: 12

Polar Surface Area: 112.66

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.05

CX Basic pKa: 7.20

CX LogP: 1.98

CX LogD: 1.77

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.39

Np Likeness Score: -0.85

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