Daunomycin derivative

ID: ALA3350774

PubChem CID: 118719127

Max Phase: Preclinical

Molecular Formula: C27H28NNa2O13P

Molecular Weight: 607.51

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](NP(=O)([O-])[O-])[C@H](O)[C@H](C)O1.[Na+].[Na+]

Standard InChI:  InChI=1S/C27H30NO13P.2Na/c1-10-22(30)14(28-42(36,37)38)7-17(40-10)41-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(39-3)18(12)25(21)33;;/h4-6,10,14,16-17,22,30,32,34-35H,7-9H2,1-3H3,(H3,28,36,37,38);;/q;2*+1/p-2/t10-,14+,16-,17-,22+,27-;;/m0../s1

Standard InChI Key:  PDZAQOKMTNZZNJ-GGTKAHFYSA-L

Molfile:  

     RDKit          2D

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    4.0554    1.2655    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0092    0.0000    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  3  2  2  0
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  8 11  2  0
  9  2  1  0
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 11  5  1  0
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 13 18  1  0
 14 16  1  0
 15  6  1  0
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 20 17  1  0
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 22 23  1  0
 23 20  1  0
 15 24  1  1
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 14 35  1  1
 22 36  1  1
 37 11  1  0
 38 30  1  0
 23 39  1  1
 40 37  2  0
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 43 38  1  0
  6 10  2  0
  4  8  1  0
 15 21  1  0
 30 41  2  0
 22 13  1  0
M  CHG  4   1   1  26  -1  27  -1  44   1
M  END

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: 607.51

Molecular Weight (Monoisotopic): 607.1455

AlogP: 0.75

#Rotatable Bonds: 6

Polar Surface Area: 229.38

Molecular Species: ACID

HBA: 11

HBD: 7

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.90

CX Basic pKa: ┄

CX LogP: 1.58

CX LogD: -1.81

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.15

Np Likeness Score: 1.58

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