2-(3,4-dichlorophenyl)-3-hydroxy-9-((tetrahydro-2H-pyran-4-yl)methyl)-9,10-dihydrochromeno[8,7-e][1,3]oxazin-4(8H)-one

ID: ALA4878528

PubChem CID: 164625842

Max Phase: Preclinical

Molecular Formula: C23H21Cl2NO5

Molecular Weight: 462.33

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=c1c(O)c(-c2ccc(Cl)c(Cl)c2)oc2c3c(ccc12)OCN(CC1CCOCC1)C3

Standard InChI:  InChI=1S/C23H21Cl2NO5/c24-17-3-1-14(9-18(17)25)22-21(28)20(27)15-2-4-19-16(23(15)31-22)11-26(12-30-19)10-13-5-7-29-8-6-13/h1-4,9,13,28H,5-8,10-12H2

Standard InChI Key:  FGEJJGOTEMPUAE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    9.3047  -14.8949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0198  -15.3080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7336  -14.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7325  -14.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4457  -15.3056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1646  -14.8944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1658  -14.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4480  -13.6480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4434  -16.1307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8782  -15.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8796  -13.6577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5936  -14.0738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3089  -13.6636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3113  -12.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5926  -12.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8803  -12.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3059  -14.0673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0194  -13.6562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0201  -12.8373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3091  -12.4232    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5956  -12.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5931  -13.6594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3146  -11.6003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5917  -11.5979    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.6027  -11.1828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6147  -10.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9069   -9.9436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1870  -10.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1794  -11.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8917  -11.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0264  -12.4255    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 17  1  2  0
  1  2  1  0
  2  4  2  0
  3 18  2  0
  3  4  1  0
  3  8  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  5  9  2  0
  6 10  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  7 11  1  0
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 20 23  1  0
 15 24  1  0
 23 25  1  0
 25 26  1  0
 25 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 14 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4878528

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 462.33

Molecular Weight (Monoisotopic): 461.0797

AlogP: 5.05

#Rotatable Bonds: 3

Polar Surface Area: 72.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.60

CX Basic pKa: 4.52

CX LogP: 4.07

CX LogD: 4.05

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.59

Np Likeness Score: -0.30

References

1. Hou Y, Kuang W, Min W, Liu Z, Zhang F, Yuan K, Wang X, Sun C, Cheng H, Wang L, Xiao Y, Pu S, Xin GZ, Yang P..  (2021)  Design, Synthesis, and Biological Evaluation of Icaritin Derivatives as Novel Putative DEPTOR Inhibitors for Multiple Myeloma Treatment.,  64  (20.0): [PMID:34644502] [10.1021/acs.jmedchem.1c00087]

Source

Source(1):

• Scientific Literature