(2S,3S,4S,5R,6S)-6-(4-(((2S,3S,4S,6R)-6-((1S,3R)-5,12-dihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yloxy)-3-hydroxy-2-methyltetrahydro-2H-pyran-4-ylcarbamoyloxy)methyl)-2-nitrophenoxy)-3,4,5-trihydroxytetrahydro-2H-pyran-2-carboxylic acid

ID: ALA2419942

PubChem CID: 73353728

Max Phase: Preclinical

Molecular Formula: C41H42N2O21

Molecular Weight: 898.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@H](C(=O)CO)C[C@@H]3O[C@H]1C[C@H](NC(=O)OCc2ccc(O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)c([N+](=O)[O-])c2)[C@H](O)[C@H](C)O1

Standard InChI:  InChI=1S/C41H42N2O21/c1-14-30(46)19(42-41(56)60-13-15-6-7-22(20(8-15)43(57)58)63-40-37(53)35(51)36(52)38(64-40)39(54)55)11-25(61-14)62-24-10-16(21(45)12-44)9-18-27(24)34(50)29-28(32(18)48)31(47)17-4-3-5-23(59-2)26(17)33(29)49/h3-8,14,16,19,24-25,30,35-38,40,44,46,48,50-53H,9-13H2,1-2H3,(H,42,56)(H,54,55)/t14-,16+,19-,24-,25-,30+,35-,36-,37+,38-,40+/m0/s1

Standard InChI Key:  DKGIHJPWTMZRSU-LQYIKZRDSA-N

Molfile:  

     RDKit          2D

 65 71  0  0  0  0  0  0  0  0999 V2000
    3.5137   -2.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -3.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2281   -4.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9426   -3.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9426   -2.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2281   -2.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6571   -4.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3715   -3.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3715   -2.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6571   -2.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0860   -4.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8005   -3.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8005   -2.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0860   -2.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5150   -4.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2294   -3.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2294   -2.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5150   -2.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6571   -4.9142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6571   -1.6142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5150   -4.9142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9439   -2.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6584   -2.8517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9439   -1.6142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3728   -2.4392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2294   -5.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2294   -6.1517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9439   -6.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6584   -6.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6584   -5.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9439   -4.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3728   -6.5642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9439   -7.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3728   -4.9142    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0873   -5.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8018   -4.9142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0873   -6.1517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5162   -5.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2307   -4.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9452   -5.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6597   -4.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6597   -4.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9452   -3.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2307   -4.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3741   -3.6767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0886   -4.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0886   -4.9142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8031   -5.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5175   -4.9142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5175   -4.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8031   -3.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8031   -6.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2320   -5.3267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2320   -3.6767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8031   -2.8517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5175   -6.5642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0886   -6.5642    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8005   -4.5017    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2281   -4.9142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5137   -5.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0860   -1.6142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0860   -4.9142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9452   -2.8517    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.6597   -2.4392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2307   -2.4392    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  1  2  0
  4  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  5  1  0
  8 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 13  1  0
  7 19  2  0
 10 20  2  0
 15 21  1  0
 17 22  1  1
 22 23  1  0
 22 24  2  0
 23 25  1  0
 26 21  1  1
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 26  1  0
 29 32  1  6
 28 33  1  6
 30 34  1  6
 34 35  1  0
 35 36  1  0
 35 37  2  0
 36 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 43 44  2  0
 44 39  1  0
 42 45  1  0
 46 45  1  1
 46 47  1  0
 47 48  1  0
 48 49  1  0
 49 50  1  0
 50 51  1  0
 51 46  1  0
 48 52  1  1
 49 53  1  6
 50 54  1  1
 51 55  1  6
 52 56  1  0
 52 57  2  0
 15 58  1  1
  3 59  1  0
 59 60  1  0
 14 61  1  0
 11 62  1  0
 43 63  1  0
 63 64  1  0
 63 65  2  0
M  CHG  2  63   1  64  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2419942

   (2S,3S,4S,5R,6S)-6-[4-[[(2S,3S,4S,6R)-6-[[(1S,3R)-5,12-dihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4-tetrahydrotetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]carbamoyloxymethyl]-2-nitrophenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

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: 898.78

Molecular Weight (Monoisotopic): 898.2280

AlogP: 0.03

#Rotatable Bonds: 12

Polar Surface Area: 357.74

Molecular Species: ACID

HBA: 20

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 23

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.70

CX Basic pKa: ┄

CX LogP: 2.33

CX LogD: -1.26

Aromatic Rings: 3

Heavy Atoms: 64

QED Weighted: 0.05

Np Likeness Score: 1.10

References

1. Legigan T, Clarhaut J, Renoux B, Tranoy-Opalinski I, Monvoisin A, Jayle C, Alsarraf J, Thomas M, Papot S..  (2013)  Synthesis and biological evaluations of a monomethylauristatin E glucuronide prodrug for selective cancer chemotherapy.,  67  [PMID:23845743] [10.1016/j.ejmech.2013.06.037]

Source

Source(1):

• Scientific Literature