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

ID: ALA3219945

PubChem CID: 10328421

Max Phase: Preclinical

Molecular Formula: C41H42N2O22

Molecular Weight: 914.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(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/C41H42N2O22/c1-14-29(46)18(42-40(56)61-13-15-6-7-20(19(8-15)43(58)59)64-39-36(53)34(51)35(52)37(65-39)38(54)55)9-24(62-14)63-22-11-41(57,23(45)12-44)10-17-26(22)33(50)28-27(31(17)48)30(47)16-4-3-5-21(60-2)25(16)32(28)49/h3-8,14,18,22,24,29,34-37,39,44,46,48,50-53,57H,9-13H2,1-2H3,(H,42,56)(H,54,55)/t14-,18-,22-,24-,29+,34-,35-,36+,37-,39+,41-/m0/s1

Standard InChI Key:  APOKYMYZOKIMLM-LUMVZWMBSA-N

Molfile:  

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M  CHG  2  51   1  53  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3219945

   Doxorubicin-glucuronide

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: 914.78

Molecular Weight (Monoisotopic): 914.2229

AlogP: -0.85

#Rotatable Bonds: 12

Polar Surface Area: 377.97

Molecular Species: ACID

HBA: 21

HBD: 10

#RO5 Violations: 3

HBA (Lipinski): 24

HBD (Lipinski): 10

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 2.70

CX Basic pKa: ┄

CX LogP: 1.36

CX LogD: -2.24

Aromatic Rings: 3

Heavy Atoms: 65

QED Weighted: 0.05

Np Likeness Score: 1.18

References

1. Grinda M, Clarhaut J, Renoux B, Tranoy-Opalinski I, Papot S.  (2012)  A self-immolative dendritic glucuronide prodrug of doxorubicin,  3  (1): [10.1039/C1MD00193K]

Source

Source(1):

• Scientific Literature