dox-saliform

ID: ALA266892

Chembl Id: CHEMBL266892

PubChem CID: 11468117

Max Phase: Preclinical

Molecular Formula: C35H36N2O13

Molecular Weight: 692.67

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](NCNC(=O)c2ccccc2O)[C@H](O)[C@H](C)O1

Standard InChI:  InChI=1S/C35H36N2O13/c1-15-29(41)19(36-14-37-34(46)16-6-3-4-8-20(16)39)10-24(49-15)50-22-12-35(47,23(40)13-38)11-18-26(22)33(45)28-27(31(18)43)30(42)17-7-5-9-21(48-2)25(17)32(28)44/h3-9,15,19,22,24,29,36,38-39,41,43,45,47H,10-14H2,1-2H3,(H,37,46)/t15-,19-,22-,24-,29+,35-/m0/s1

Standard InChI Key:  XEXRSNKGQVJRPG-DKNGMFFESA-N

Alternative Forms

1. Parent:

   

   ALA266892

   2-hydroxy-N-[[[(2S,3S,4S,6R)-3-hydroxy-2-methyl-6-[[(1S,3S)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]oxan-4-yl]amino]methyl]benzamide

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: 692.67

Molecular Weight (Monoisotopic): 692.2217

AlogP: 0.73

#Rotatable Bonds: 9

Polar Surface Area: 241.41

Molecular Species: NEUTRAL

HBA: 14

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 15

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 7.79

CX Basic pKa: 7.34

CX LogP: 2.57

CX LogD: 2.75

Aromatic Rings: 3

Heavy Atoms: 50

QED Weighted: 0.09

Np Likeness Score: 1.28

References

1. Burke PJ, Kalet BT, Koch TH..  (2004)  Antiestrogen binding site and estrogen receptor mediate uptake and distribution of 4-hydroxytamoxifen-targeted doxorubicin-formaldehyde conjugate in breast cancer cells.,  47  (26): [PMID:15588086] [10.1021/jm049496b]

2. Barthel BL, Mooz EL, Wiener LE, Koch GG, Koch TH..  (2016)  Correlation of in Situ Oxazolidine Formation with Highly Synergistic Cytotoxicity and DNA Cross-Linking in Cancer Cells from Combinations of Doxorubicin and Formaldehyde.,  59  (5): [PMID:26881291] [10.1021/acs.jmedchem.5b01956]

Source

Source(1):

• Scientific Literature