7-epi-3'-N-de-tert-butoxycarbonyl-3'-[2-(1,1,1-trifluoro-2-methyl)propyloxycarbonyl]-docetaxel

ID: ALA3780839

PubChem CID: 127033181

Max Phase: Preclinical

Molecular Formula: C43H50F3NO14

Molecular Weight: 861.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@@]12CO[C@@H]1C[C@@H](O)[C@@]1(C)C(=O)[C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C(F)(F)F)c4ccccc4)C[C@@](O)([C@@H](OC(=O)c4ccccc4)C12)C3(C)C

Standard InChI:  InChI=1S/C43H50F3NO14/c1-21-25(58-36(54)31(51)29(23-14-10-8-11-15-23)47-37(55)61-39(5,6)43(44,45)46)19-42(56)34(59-35(53)24-16-12-9-13-17-24)32-40(7,33(52)30(50)28(21)38(42,3)4)26(49)18-27-41(32,20-57-27)60-22(2)48/h8-17,25-27,29-32,34,49-51,56H,18-20H2,1-7H3,(H,47,55)/t25-,26+,27+,29-,30+,31+,32?,34-,40+,41-,42+/m0/s1

Standard InChI Key:  KDNQXWLCGMTBNC-YSLHZGQCSA-N

Molfile:  

     RDKit          2D

 62 67  0  0  0  0  0  0  0  0999 V2000
   -4.9128   -0.2943    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2102   -1.0489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5128   -0.3034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2060   -2.2488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8102   -1.0581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1128   -0.3126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4105   -1.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7109   -0.3172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7136    1.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.4159    1.9352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1155    1.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5170    0.8966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8018   -2.5589    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4984   -3.3029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4623   -2.6975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4901   -4.8037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1867   -5.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1783   -7.0485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1362   -7.6434    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2144   -7.6539    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1723   -8.2485    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1506   -4.9423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1928   -4.3477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -3.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6100   -2.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6100   -1.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3300   -0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600   -1.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0200    0.2800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400   -2.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7600   -3.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4900   -2.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4900   -1.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2100   -0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2100   -3.2200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600   -2.4900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7580   -4.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4880   -3.6900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600   -1.2900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2080   -4.4200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0600    0.1600    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2081    1.1912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5064    1.9441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5045    3.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5466    1.3458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8011    4.1993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    5.6993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4946    6.4450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1980    5.6907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2030    4.1907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0400   -1.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7600   -0.3100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900    0.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7600    0.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5124   -1.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1044   -2.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1819   -1.5433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9007   -3.4933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0069   -1.2950    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1945    1.1510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6476   -3.0927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1759    0.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  1
  5 13  1  1
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 18 21  1  0
 17 22  1  0
 17 23  1  0
 24 25  2  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 32 31  1  0
 33 52  1  0
 51 30  1  0
 30 31  1  0
 32 33  1  0
 33 34  1  0
 32 35  1  0
 35 36  1  0
 36 24  1  0
 28 34  1  0
 31 37  1  1
 32 38  1  6
 36 39  1  1
 35 40  2  0
 28 41  1  1
 34 42  1  1
 42 43  1  0
 43 44  1  0
 43 45  2  0
 44 46  2  0
 46 47  1  0
 47 48  2  0
 48 49  1  0
 49 50  2  0
 50 44  1  0
 51 52  1  0
 52 53  1  0
 53 54  1  0
 54 51  1  0
 52 55  1  1
 55 56  1  0
 56 57  1  0
 56 58  2  0
 51 59  1  1
 29 60  1  0
 25 61  1  0
 26  1  1  1
 29 62  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3780839

   ---

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: 861.86

Molecular Weight (Monoisotopic): 861.3183

AlogP: 3.80

#Rotatable Bonds: 9

Polar Surface Area: 224.45

Molecular Species: NEUTRAL

HBA: 14

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 15

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.89

CX Basic pKa: ┄

CX LogP: 3.52

CX LogD: 3.52

Aromatic Rings: 2

Heavy Atoms: 61

QED Weighted: 0.14

Np Likeness Score: 1.79

References

1. Tang ML, Zhou L, Chang J, Hu ZH, Qin Y, Sun X..  (2016)  Differential metabolism of 3FDT and docetaxel in RLMs, rats, and HLMs.,  113  [PMID:26922231] [10.1016/j.ejmech.2016.02.007]

Source

Source(1):

• Scientific Literature