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

ID: ALA4874925

PubChem CID: 71502373

Max Phase: Preclinical

Molecular Formula: C26H28O5

Molecular Weight: 420.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc2c(c(O)c1C(=O)/C=C/c1ccc(O)cc1)C=CC(C)(CCC=C(C)C)O2

Standard InChI:  InChI=1S/C26H28O5/c1-17(2)6-5-14-26(3)15-13-20-22(31-26)16-23(30-4)24(25(20)29)21(28)12-9-18-7-10-19(27)11-8-18/h6-13,15-16,27,29H,5,14H2,1-4H3/b12-9+

Standard InChI Key:  XPJCSPIEMVSUCT-FMIVXFBMSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
    8.5869  -21.6312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2939  -22.0400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0005  -21.6310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9997  -20.8129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2864  -20.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5827  -20.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7062  -20.4023    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8065  -19.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6237  -19.6043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2187  -18.8946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3352  -21.6414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0432  -22.0503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3363  -20.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406  -20.4109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0368  -19.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3304  -19.1939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6283  -20.4219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4625  -22.8656    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0430  -22.8675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7500  -20.8182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7534  -21.6389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4618  -22.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1715  -21.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4551  -20.4027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8797  -22.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3352  -23.2759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4015  -18.8904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5843  -18.8863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1793  -18.1766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3621  -18.1724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5915  -17.4709    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
  5  6  2  0
  6  1  1  0
  4  7  1  0
  9  8  1  0
 10  9  1  0
 13 11  2  0
 11 12  1  0
 12 21  2  0
 20 14  2  0
 13 14  1  0
 13 17  1  0
 14 15  1  0
 15 16  2  0
 16  9  1  0
  9 17  1  0
 22 18  2  0
 12 19  1  0
 20 21  1  0
 20 24  1  0
 21 22  1  0
 22 23  1  0
 23 25  2  0
 25  1  1  0
 19 26  1  0
  8 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874925

   (2E)-1-(5-hydroxy-7-methoxy-2-methyl-2-(4-methylpent-3-enyl)-2H-chromen-6-yl)-3-(4-hydroxyphenyl)prop-2-en-1-one

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: 420.51

Molecular Weight (Monoisotopic): 420.1937

AlogP: 5.91

#Rotatable Bonds: 7

Polar Surface Area: 75.99

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.08

CX Basic pKa: ┄

CX LogP: 6.41

CX LogD: 5.92

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.33

Np Likeness Score: 2.43

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