5,7-dihydroxy-8-(2-methylbutanoyl)-6-(3-methylbutyl)-4-phenyl-chroman-2-one

ID: ALA5284038

Max Phase: Preclinical

Molecular Formula: C25H30O5

Molecular Weight: 410.51

Names and Identifiers

Canonical SMILES:  CCC(C)C(=O)c1c(O)c(CCC(C)C)c(O)c2c1OC(=O)CC2c1ccccc1

Standard InChI:  InChI=1S/C25H30O5/c1-5-15(4)22(27)21-24(29)17(12-11-14(2)3)23(28)20-18(13-19(26)30-25(20)21)16-9-7-6-8-10-16/h6-10,14-15,18,28-29H,5,11-13H2,1-4H3

Standard InChI Key:  RPPPZDIIFHACRY-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    1.0659    0.4115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0659   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589   -0.8202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3589   -1.6419    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7821   -3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7776   -0.8210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4892   -0.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4892    0.4114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776    0.8223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7776    1.6440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0661    2.0551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0668    2.8743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7786    3.2853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4875    2.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4923    2.0566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2008   -0.8211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3571    1.6433    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0660    0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7776    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892    0.8219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2008    0.4111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892    1.6436    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0660   -0.8247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  4  3  1  0
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  1  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
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  7 12  2  0
  5 13  1  0
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 15 16  1  0
  4 16  1  0
 16 17  1  0
 18 17  2  0
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 20 19  2  0
 21 20  1  0
 22 21  2  0
 17 22  1  0
 14 23  2  0
  3 24  1  0
  2 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 27 29  1  0
  1 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5284038

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 410.51

Molecular Weight (Monoisotopic): 410.2093

AlogP: 5.36

#Rotatable Bonds: 7

Polar Surface Area: 83.83

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.59

CX Basic pKa: ┄

CX LogP: 6.73

CX LogD: 6.51

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.36

Np Likeness Score: 1.35

References

1. Gonçalves GA, Spillere AR, das Neves GM, Kagami LP, von Poser GL, Canto RFS, Eifler-Lima V..  (2020)  Natural and synthetic coumarins as antileishmanial agents: A review.,  203  [PMID:32668302] [10.1016/j.ejmech.2020.112514]

Source

Source(1):

• Scientific Literature