Daunomycin derivative

ID: ALA3350772

PubChem CID: 118719124

Max Phase: Preclinical

Molecular Formula: C27H29NO13S

Molecular Weight: 607.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(C)=O)C[C@@H]3O[C@H]1C[C@@H](N)[C@H](OS(=O)(=O)O)[C@H](C)O1

Standard InChI:  InChI=1S/C27H29NO13S/c1-10-26(41-42(35,36)37)14(28)7-17(39-10)40-16-9-27(34,11(2)29)8-13-19(16)25(33)21-20(23(13)31)22(30)12-5-4-6-15(38-3)18(12)24(21)32/h4-6,10,14,16-17,26,31,33-34H,7-9,28H2,1-3H3,(H,35,36,37)/t10-,14+,16-,17-,26+,27-/m0/s1

Standard InChI Key:  DLCSTDOMSIBIQJ-JBBADZSPSA-N

Molfile:  

     RDKit          2D

 42 46  0  0  0  0  0  0  0  0999 V2000
    2.3728   -3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3728   -2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583   -2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583   -3.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8017   -2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8017   -3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3741    1.0018    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.9439   -2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0873   -3.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0873   -2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9439   -3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6596   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2307   -3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5162   -2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5162   -3.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2307   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6596   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2307   -0.2357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2307   -2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3741    0.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9452   -1.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9452    0.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5162   -1.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3741    1.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6679   -4.2354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5491    1.0018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1991    1.0018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3741   -1.4732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583   -4.7732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6583   -1.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2294   -2.2982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4924   -4.2066    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0873   -4.7732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0873   -1.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0552   -3.5645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2294   -3.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2294   -1.4732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9452    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4851   -3.5357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4851   -2.7107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2806   -4.9638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4851   -1.0607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  6  1  0
  6  9  2  0
  7 20  1  0
  8 11  2  0
  9  1  1  0
 10  2  1  0
 11  4  1  0
 12 17  1  0
 13 15  1  0
 14  5  1  0
 15  6  1  0
 16 23  1  6
 17 21  1  0
 18 16  1  0
 19 13  1  0
 12 20  1  1
 21 16  1  0
 22 18  1  0
 14 23  1  1
 24  7  1  0
 13 25  1  6
 26  7  2  0
 27  7  2  0
 17 28  1  6
 29  4  2  0
 30  3  2  0
 31  8  1  0
 32 25  2  0
 33  9  1  0
 34 10  1  0
 13 35  1  1
 36 11  1  0
 37 31  1  0
 22 38  1  1
 39 36  2  0
 40 39  1  0
 41 25  1  0
 42 37  1  0
  5 10  2  0
  3  8  1  0
 14 19  1  0
 31 40  2  0
 22 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3350772

   ---

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: 607.59

Molecular Weight (Monoisotopic): 607.1360

AlogP: 0.86

#Rotatable Bonds: 6

Polar Surface Area: 229.21

Molecular Species: ZWITTERION

HBA: 13

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -2.13

CX Basic pKa: 8.92

CX LogP: 1.37

CX LogD: 1.26

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.19

Np Likeness Score: 1.78

References

1. Leenders RG, Scheeren HW, Houba PH, Boven E, Haisma HJ.  (1995)  Synthesis and evaluation of novel daunomycin-phosphate-sulfate --glucuronide and --glucoside prodrugs for application in adept,  5  (24): [10.1016/0960-894X(95)00523-3]

Source

Source(1):

• Scientific Literature