[({[(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.0^{1,12}.0^{6,17}]heptadeca-6,8,10(17),15-tetraen-14-yl]oxy}(4-nitrophenoxy)phosphoryl)oxy]phosphonic acid

ID: ALA568258

Chembl Id: CHEMBL568258

PubChem CID: 45483338

Max Phase: Preclinical

Molecular Formula: C23H26N2O11P2

Molecular Weight: 568.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c3c1O[C@H]1C[C@@H](OP(=O)(Oc4ccc([N+](=O)[O-])cc4)OP(=O)(O)O)C=C[C@@]31CCN(C)C2

Standard InChI:  InChI=1S/C23H26N2O11P2/c1-24-12-11-23-10-9-18(13-20(23)33-22-19(32-2)8-3-15(14-24)21(22)23)35-38(31,36-37(28,29)30)34-17-6-4-16(5-7-17)25(26)27/h3-10,18,20H,11-14H2,1-2H3,(H2,28,29,30)/t18-,20-,23-,38?/m0/s1

Standard InChI Key:  QHAJPODVYRAMGA-RHNVWUFNSA-N

Alternative Forms

1. Parent:

   

   ALA568258

   [(1S,12S,14R)-9-methoxy-4-methyl-11-oxa-4-azatetracyclo[8.6.1.01,12.06,17]heptadeca-6(17),7,9,15-tetraen-14-yl] (4-nitrophenyl) phosphono phosphate

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: 568.41

Molecular Weight (Monoisotopic): 568.1012

AlogP: 4.08

#Rotatable Bonds: 8

Polar Surface Area: 167.13

Molecular Species: ZWITTERION

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -0.05

CX Basic pKa: 8.58

CX LogP: 1.11

CX LogD: -1.00

Aromatic Rings: 2

Heavy Atoms: 38

QED Weighted: 0.20

Np Likeness Score: 0.98

References

1. Koteswara Rao V, Janardhan Rao A, Subba Reddy S, Naga Raju C, Visweswara Rao P, Ghosh SK..  (2010)  Synthesis, spectral characterization and biological evaluation of phosphorylated derivatives of galanthamine.,  45  (1): [PMID:19853328] [10.1016/j.ejmech.2009.09.045]

Source

Source(1):

• Scientific Literature