2-(2,4-dimethoxyphenyl)-3,7-dihydroxy-8-(morpholinomethyl)-4H-chromen-4-one

ID: ALA4860014

PubChem CID: 164613700

Max Phase: Preclinical

Molecular Formula: C22H23NO7

Molecular Weight: 413.43

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2oc3c(CN4CCOCC4)c(O)ccc3c(=O)c2O)c(OC)c1

Standard InChI:  InChI=1S/C22H23NO7/c1-27-13-3-4-14(18(11-13)28-2)22-20(26)19(25)15-5-6-17(24)16(21(15)30-22)12-23-7-9-29-10-8-23/h3-6,11,24,26H,7-10,12H2,1-2H3

Standard InChI Key:  XVUWPENZZBTFOO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   22.6901   -5.3282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6889   -6.1478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3970   -6.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3952   -4.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9823   -4.9198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3928   -4.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6838   -3.6957    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.1038   -5.3246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1027   -6.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8089   -6.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5207   -6.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5219   -5.3266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8112   -4.9130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.8066   -7.3715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2273   -6.5578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2287   -4.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9357   -5.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6440   -4.9285    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6464   -4.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9347   -3.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2294   -4.1088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5215   -3.7005    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.5213   -2.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3545   -3.7026    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.0618   -4.1120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6840   -2.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9791   -2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2702   -2.8758    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2707   -3.6940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9801   -4.1049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  3  9  2  0
  8  4  2  0
  4  1  1  0
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  4  6  1  0
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  9 10  1  0
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 11 12  2  0
 12 13  1  0
 10 14  2  0
 11 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 12 16  1  0
 21 22  1  0
 22 23  1  0
 19 24  1  0
 24 25  1  0
  7 26  1  0
  7 30  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4860014

   ---

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: 413.43

Molecular Weight (Monoisotopic): 413.1475

AlogP: 2.72

#Rotatable Bonds: 5

Polar Surface Area: 101.60

Molecular Species: ACID

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.00

CX Basic pKa: 6.04

CX LogP: 1.07

CX LogD: 0.15

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.66

Np Likeness Score: 0.10

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