(E)-3-(2,3-dimethoxyphenyl)-1-(5-hydroxy-2,2-dimethyl-2H-chroman-6-yl)-propenone

ID: ALA3359426

PubChem CID: 118723523

Max Phase: Preclinical

Molecular Formula: C22H22O5

Molecular Weight: 366.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(/C=C/C(=O)c2ccc3c(c2O)C=CC(C)(C)O3)c1OC

Standard InChI:  InChI=1S/C22H22O5/c1-22(2)13-12-16-18(27-22)11-9-15(20(16)24)17(23)10-8-14-6-5-7-19(25-3)21(14)26-4/h5-13,24H,1-4H3/b10-8+

Standard InChI Key:  CWMSFPRZCPQMIL-CSKARUKUSA-N

Molfile:  

     RDKit          2D

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    1.8116  -12.0512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9867  -12.0523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3981  -12.7668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8116  -11.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5242  -12.4574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5242  -10.8075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2326  -11.2261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2310  -12.0493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9424  -12.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6561  -12.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6537  -11.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9416  -10.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9396   -9.9889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3673  -10.8066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0837  -11.2188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3647   -9.9815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7974  -10.8020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5136  -11.2143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5122  -12.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2245  -12.4476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9364  -12.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9357  -11.2126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2232  -10.7958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6509  -10.7981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6510   -9.9732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2205   -9.9709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5043   -9.5627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  1  3  1  0
  4  1  1  0
  4  6  2  0
  1  5  1  0
  5  8  1  0
  7  6  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
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 11 14  1  0
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 14 16  2  0
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 17 18  1  0
 18 19  1  0
 18 23  2  0
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 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 23 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3359426

   ---

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: 366.41

Molecular Weight (Monoisotopic): 366.1467

AlogP: 4.49

#Rotatable Bonds: 5

Polar Surface Area: 64.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.06

CX Basic pKa: ┄

CX LogP: 4.82

CX LogD: 4.32

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: 1.40

References

1. Wang L, Chen G, Lu X, Wang S, Han S, Li Y, Ping G, Jiang X, Li H, Yang J, Wu C..  (2015)  Novel chalcone derivatives as hypoxia-inducible factor (HIF)-1 inhibitor: synthesis, anti-invasive and anti-angiogenic properties.,  89  [PMID:25462229] [10.1016/j.ejmech.2014.10.036]

Source

Source(1):

• Scientific Literature