1,9-dihydroxy-10,14,17,17-tetramethyl-4,12-di(methylcarbonyloxy)-11-oxo-2-phenylcarbonyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-15-yl 2-hydroxy-3-phenylcarboxamido-3-(4-pyridyl)propanoate

ID: ALA280831

PubChem CID: 10724260

Max Phase: Preclinical

Molecular Formula: C46H50N2O14

Molecular Weight: 854.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccncc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O

Standard InChI:  InChI=1S/C46H50N2O14/c1-24-30(60-42(56)35(52)34(27-17-19-47-20-18-27)48-40(54)28-13-9-7-10-14-28)22-46(57)39(61-41(55)29-15-11-8-12-16-29)37-44(6,31(51)21-32-45(37,23-58-32)62-26(3)50)38(53)36(59-25(2)49)33(24)43(46,4)5/h7-20,30-32,34-37,39,51-52,57H,21-23H2,1-6H3,(H,48,54)/t30-,31-,32+,34-,35+,36+,37-,39-,44+,45-,46+/m0/s1

Standard InChI Key:  NWPVLFBFOQDTDK-JKZNWJFHSA-N

Molfile:  

     RDKit          2D

 64 70  0  0  1  0  0  0  0  0999 V2000
    7.2000   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792   -6.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8792   -5.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4042   -4.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792   -4.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8792   -4.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167   -5.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0917   -3.9375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -4.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5292   -5.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1292   -4.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -4.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0167   -4.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -4.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2000   -6.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1625   -3.6167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125   -6.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1542   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5750   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -7.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -4.8667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9625   -6.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5167   -5.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3750   -7.0875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7792   -6.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0292   -3.1125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0792   -7.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -3.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5875   -3.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8875   -2.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6792   -6.7375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375   -6.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3875   -7.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4417   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958   -5.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8375   -7.2792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2167   -1.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6042   -4.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667   -5.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4250   -4.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917   -4.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3625   -5.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -3.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2750   -6.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9875   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0792   -8.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042   -3.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375   -5.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2708   -4.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6625   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6750   -8.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -8.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6625   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6667   -9.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1000   -9.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4875   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4833   -3.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9083   -3.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -9.6292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8750   -6.4375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0250   -6.1625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  8  1  0
  4  1  1  0
  5  9  1  0
  6  5  1  0
  7  1  1  0
  8  4  1  0
  9  7  1  0
 10  5  2  0
 11  3  1  0
 12 10  1  0
 13 22  1  0
 14  1  1  0
 15 13  1  0
 16 24  1  0
 19 17  1  6
  8 18  1  6
 19 15  1  0
 20 17  1  0
 21 18  1  0
 12 22  1  6
  2 23  1  0
 24 14  1  0
  2 25  1  6
 16 26  1  0
  9 27  1  1
 28 25  1  0
 29 27  1  0
 30  7  2  0
 31 13  2  0
 32 20  2  0
 33 21  2  0
  3 34  1  1
 35 20  1  0
 36 21  1  0
 37 19  1  0
 38 48  2  0
 39 28  2  0
 40 29  2  0
  1 41  1  1
 15 42  1  6
 14 43  1  1
  6 44  1  0
  6 45  1  0
 46 10  1  0
 47 51  2  0
 48 52  1  0
 49 28  1  0
 50 29  1  0
 51 37  1  0
 52 37  2  0
 53 35  1  0
 54 36  2  0
 55 36  1  0
 56 35  2  0
 57 54  1  0
 58 55  2  0
 59 56  1  0
 60 53  2  0
 61 59  2  0
 62 58  1  0
  4 63  1  6
 16  2  1  0
 26 23  1  0
  6  3  1  0
 12 11  1  0
 62 57  2  0
 38 47  1  0
 61 60  1  0
 16 64  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA280831

   [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-pyridin-4-ylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate

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: 854.91

Molecular Weight (Monoisotopic): 854.3262

AlogP: 3.13

#Rotatable Bonds: 10

Polar Surface Area: 234.18

Molecular Species: NEUTRAL

HBA: 15

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 16

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.86

CX Basic pKa: 5.01

CX LogP: 2.32

CX LogD: 2.32

Aromatic Rings: 3

Heavy Atoms: 62

QED Weighted: 0.13

Np Likeness Score: 1.82

References

1. Georg GI, Harriman GC, Hepperle M, Himes RH.  (1994)  Heteroaromatic Taxol Analogues: The Chemistry and Biological Activities of 3-Furyl and 3-Pyridyl Substituted Taxanes,  4  (11): [10.1016/S0960-894X(01)80366-8]

2. Czaplinski KA, Grunewald GL.  (1994)  A comparative molecular field analysis derived model of the binding of taxol analogues to microtubules,  4  (18): [10.1016/S0960-894X(00)80073-6]

Source

Source(1):

• Scientific Literature