(2E)-1-(5-Hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

ID: ALA4865912

PubChem CID: 15230651

Max Phase: Preclinical

Molecular Formula: C22H22O5

Molecular Weight: 366.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=C/C(=O)c2c(OC)cc3c(c2O)C=CC(C)(C)O3)cc1

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

Standard InChI Key:  QPRYWSHCBHNFJL-JXMROGBWSA-N

Molfile:  

 
     RDKit          2D

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   16.9982  -20.7645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7052  -21.1733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4118  -20.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4110  -19.9462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6977  -19.5389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9940  -19.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1175  -19.5355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.2178  -18.7335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0350  -18.7376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6300  -18.0278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7464  -20.7746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4545  -21.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7476  -19.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4519  -19.5441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4481  -18.7332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7417  -18.3272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0396  -19.5552    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8738  -21.9989    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4543  -22.0008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1613  -19.9515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1647  -20.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8731  -21.1773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5828  -20.7663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8664  -19.5360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2910  -21.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7465  -22.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8264  -19.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
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  6  1  1  0
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  9 17  1  0
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 12 19  1  0
 20 21  1  0
 20 24  1  0
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 22 23  1  0
 23 25  2  0
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 19 26  1  0
  7 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4865912

   Glychalcone A

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: 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: 7.09

CX Basic pKa: ┄

CX LogP: 4.82

CX LogD: 4.34

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.62

Np Likeness Score: 1.69

References

1. Urmann C, Bieler L, Priglinger E, Aigner L, Couillard-Despres S, Riepl HM..  (2021)  Neuroregenerative Potential of Prenyl- and Pyranochalcones: A Structure-Activity Study.,  84  (10.0): [PMID:34542287] [10.1021/acs.jnatprod.1c00505]

Source

Source(1):

• Scientific Literature