(2E)-3-(Benzo[d][1,3]dioxol-6-yl)-1-(5-hydroxy-7-methoxy-2,2-dimethyl-2H-chromen-6-yl)prop-2-en-1-one

ID: ALA4862947

PubChem CID: 15719487

Max Phase: Preclinical

Molecular Formula: C22H20O6

Molecular Weight: 380.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(c(O)c1C(=O)/C=C/c1ccc3c(c1)OCO3)C=CC(C)(C)O2

Standard InChI:  InChI=1S/C22H20O6/c1-22(2)9-8-14-17(28-22)11-19(25-3)20(21(14)24)15(23)6-4-13-5-7-16-18(10-13)27-12-26-16/h4-11,24H,12H2,1-3H3/b6-4+

Standard InChI Key:  RJYLDTKZVYKSBL-GQCTYLIASA-N

Molfile:  

 
     RDKit          2D

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   17.1261  -27.9747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8332  -28.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8256  -26.7491    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1219  -27.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3156  -26.9027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3458  -25.9438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1629  -25.9479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7579  -25.2381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8744  -27.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5824  -28.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8755  -27.1654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5798  -26.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5760  -25.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8696  -25.5374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1675  -26.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0017  -29.2091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5822  -29.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2893  -27.1618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2926  -27.9824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0011  -28.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7107  -27.9766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9943  -26.7463    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4190  -28.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8744  -29.6195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3181  -28.2255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5389  -27.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5399  -27.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7979  -27.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2 27  1  0
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  3  4  2  0
  4  1  1  0
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  7  6  1  0
  8  7  1  0
 11  9  2  0
  9 10  1  0
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 18 12  2  0
 11 12  1  0
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 12 13  1  0
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  7 15  1  0
 20 16  2  0
 10 17  1  0
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 20 21  1  0
 21 23  2  0
 23  1  1  0
 17 24  1  0
 27 25  1  0
 26 27  2  0
 25 28  1  0
 28  5  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4862947

   Glabrachromene I

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: 380.40

Molecular Weight (Monoisotopic): 380.1260

AlogP: 4.21

#Rotatable Bonds: 4

Polar Surface Area: 74.22

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.09

CX Basic pKa: ┄

CX LogP: 4.60

CX LogD: 4.12

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.63

Np Likeness Score: 1.75

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