(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 (4-nitrophenyl) [(2-hydroxyethyl)sulfanyl]phosphonate

ID: ALA590951

Chembl Id: CHEMBL590951

PubChem CID: 45483356

Max Phase: Preclinical

Molecular Formula: C25H29N2O8PS

Molecular Weight: 548.55

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C25H29N2O8PS/c1-26-12-11-25-10-9-20(15-22(25)33-24-21(32-2)8-3-17(16-26)23(24)25)35-36(31,37-14-13-28)34-19-6-4-18(5-7-19)27(29)30/h3-10,20,22,28H,11-16H2,1-2H3/t20-,22-,25-,36?/m0/s1

Standard InChI Key:  FNCCQAWXISUGLU-VJFLIXRMSA-N

Alternative Forms

1. Parent:

   

   ALA590951

   2-[[(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]oxy-(4-nitrophenoxy)phosphoryl]sulfanylethanol

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: 548.55

Molecular Weight (Monoisotopic): 548.1382

AlogP: 4.70

#Rotatable Bonds: 9

Polar Surface Area: 120.60

Molecular Species: BASE

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.58

CX LogP: 2.97

CX LogD: 1.76

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.20

Np Likeness Score: 0.85

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