(S)-methyl 2-((2R,3R)-3-((S)-1-((3R,4S,5S)-4-((S)-2-((S)-2-(dimethylamino)-3-methylbutanamido)-N-methylpent-4-ynamido)-3-methoxy-5-methylheptanoyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanamido)-3-phenylpropanoate

ID: ALA4177398

PubChem CID: 130195339

Max Phase: Preclinical

Molecular Formula: C41H65N5O8

Molecular Weight: 756.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C#CC[C@H](NC(=O)[C@H](C(C)C)N(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)[C@@H](CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@@H](Cc1ccccc1)C(=O)OC)OC

Standard InChI:  InChI=1S/C41H65N5O8/c1-13-19-30(42-39(49)35(26(3)4)44(7)8)40(50)45(9)36(27(5)14-2)33(52-10)25-34(47)46-23-18-22-32(46)37(53-11)28(6)38(48)43-31(41(51)54-12)24-29-20-16-15-17-21-29/h1,15-17,20-21,26-28,30-33,35-37H,14,18-19,22-25H2,2-12H3,(H,42,49)(H,43,48)/t27-,28+,30-,31-,32-,33+,35-,36-,37+/m0/s1

Standard InChI Key:  WSMOWWVWMCOJJZ-KFXXZZRKSA-N

Molfile:  

     RDKit          2D

 55 56  0  0  0  0  0  0  0  0999 V2000
   18.2465  -18.5436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9542  -18.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6619  -18.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3696  -18.1350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6619  -19.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5388  -18.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2465  -19.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9542  -17.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6619  -16.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2465  -16.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0773  -18.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7850  -18.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4927  -18.5436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7850  -17.3179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4927  -19.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2004  -18.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9081  -18.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2004  -17.3179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9081  -16.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4927  -16.9093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9081  -19.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6159  -18.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3236  -18.5436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6159  -19.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3236  -19.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0313  -18.1350    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.7769  -18.4670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3237  -17.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9151  -17.1520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1158  -17.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9468  -19.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3395  -19.8132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5094  -20.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7240  -19.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8939  -20.3182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3313  -18.9721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2866  -20.8650    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.6711  -20.5708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8410  -21.3701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6182  -21.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2255  -21.0758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0002  -21.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6072  -20.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4375  -19.9860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6555  -19.7347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0519  -20.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6159  -17.3178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0634  -18.8697    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.0773  -19.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3696  -19.7694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2337  -21.9169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4565  -21.6644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.4036  -22.7162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8492  -22.2112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6580  -20.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  2  0
  1  6  1  0
  1  7  1  0
  2  8  1  1
  8  9  1  0
  8 10  1  0
 11  4  1  6
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 16 13  1  1
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  1
 17 21  1  1
 17 22  1  0
 22 23  1  0
 21 24  1  0
 23 25  2  0
 23 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 26  1  0
 27 31  1  0
 31 32  1  1
 32 33  1  0
 31 34  1  0
 34 35  1  0
 34 36  1  1
 35 37  2  0
 35 38  1  0
 39 38  1  1
 39 40  1  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 44 45  1  0
 45 46  2  0
 46 41  1  0
 19 47  1  0
 27 48  1  6
 11 49  1  0
 49 50  1  0
 39 51  1  0
 51 52  1  0
 51 53  2  0
 52 54  1  0
 50 55  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4177398

   ---

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: 756.00

Molecular Weight (Monoisotopic): 755.4833

AlogP: 2.90

#Rotatable Bonds: 21

Polar Surface Area: 146.82

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 12.04

CX Basic pKa: 8.03

CX LogP: 3.51

CX LogD: 2.79

Aromatic Rings: 1

Heavy Atoms: 54

QED Weighted: 0.14

Np Likeness Score: 0.51

References

1. Dugal-Tessier J, Barnscher SD, Kanai A, Mendelsohn BA..  (2017)  Synthesis and Evaluation of Dolastatin 10 Analogues Containing Heteroatoms on the Amino Acid Side Chains.,  80  (9): [PMID:28885014] [10.1021/acs.jnatprod.7b00359]

Source

Source(1):

• Scientific Literature