doxazolidine

ID: ALA217089

Chembl Id: CHEMBL217089

PubChem CID: 11599300

Max Phase: Preclinical

Molecular Formula: C28H29NO11

Molecular Weight: 555.54

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Doxazolidine | doxazolidine|CHEMBL217089|SCHEMBL12567109|(7S,9S)-7-[[(3aS,4S,6R,7aS)-4-methyl-2,3a,4,6,7,7a-hexahydro-1H-pyrano[4,3-d][1,3]oxazol-6-yl]oxy]-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione

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]2NCO[C@@H]2[C@H](C)O1

Standard InChI:  InChI=1S/C28H29NO11/c1-11-27-14(29-10-38-27)6-18(39-11)40-16-8-28(36,17(31)9-30)7-13-20(16)26(35)22-21(24(13)33)23(32)12-4-3-5-15(37-2)19(12)25(22)34/h3-5,11,14,16,18,27,29-30,33,35-36H,6-10H2,1-2H3/t11-,14-,16-,18-,27+,28-/m0/s1

Standard InChI Key:  DMROAWTZXCKQPT-PODHPLMESA-N

Alternative Forms

1. Parent:

   

   ALA217089

   DOXAZOLIDINE

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: 555.54

Molecular Weight (Monoisotopic): 555.1741

AlogP: 0.63

#Rotatable Bonds: 5

Polar Surface Area: 181.08

Molecular Species: BASE

HBA: 12

HBD: 5

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 7.86

CX Basic pKa: 8.51

CX LogP: 1.79

CX LogD: 1.50

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.28

Np Likeness Score: 1.66

References

1. Burkhart DJ, Barthel BL, Post GC, Kalet BT, Nafie JW, Shoemaker RK, Koch TH..  (2006)  Design, synthesis, and preliminary evaluation of doxazolidine carbamates as prodrugs activated by carboxylesterases.,  49  (24): [PMID:17125253] [10.1021/jm060597e]

2. Kalet BT, McBryde MB, Espinosa JM, Koch TH..  (2007)  Doxazolidine induction of apoptosis by a topoisomerase II independent mechanism.,  50  (18): [PMID:17696516] [10.1021/jm070569b]

3. Barthel BL, Zhang Z, Rudnicki DL, Coldren CD, Polinkovsky M, Sun H, Koch GG, Chan DC, Koch TH..  (2009)  Preclinical efficacy of a carboxylesterase 2-activated prodrug of doxazolidine.,  52  (23): [PMID:19634903] [10.1021/jm900694z]

4. 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