Daunomycin derivative

ID: ALA3350775

PubChem CID: 118719129

Max Phase: Preclinical

Molecular Formula: C27H29NNaO13P

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

Standard InChI:  InChI=1S/C27H30NO13P.Na/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,(H2,35,36,37);/q;+1/p-1/t10-,14+,16-,17-,26+,27-;/m0./s1

Standard InChI Key:  PDOSXWCYPZTROB-XDKGUSKUSA-M

Molfile:  

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M  CHG  2   1   1  27  -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: 1.15

#Rotatable Bonds: 6

Polar Surface Area: 232.37

Molecular Species: ZWITTERION

HBA: 12

HBD: 6

#RO5 Violations: 3

HBA (Lipinski): 14

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 0.83

CX Basic pKa: 10.07

CX LogP: 1.18

CX LogD: -0.18

Aromatic Rings: 2

Heavy Atoms: 42

QED Weighted: 0.17

Np Likeness Score: 1.71

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