6',8'-dichloroisoplagiochin C

ID: ALA5278865

Max Phase: Preclinical

Molecular Formula: C28H20Cl2O4

Molecular Weight: 491.37

Names and Identifiers

Canonical SMILES:  Oc1ccc2c(c1)CCc1ccc(O)c(c1)-c1cc(cc(Cl)c1O)/C=C(/Cl)c1ccc-2c(O)c1

Standard InChI:  InChI=1S/C28H20Cl2O4/c29-24-11-16-10-23(28(34)25(30)12-16)22-9-15(2-8-26(22)32)1-3-17-13-19(31)5-7-20(17)21-6-4-18(24)14-27(21)33/h2,4-14,31-34H,1,3H2/b24-11+

Standard InChI Key:  CKMYJCBTJCAETK-BHGWPJFGSA-N

Molfile:  

 
     RDKit          2D

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   -3.2120   -2.9703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4975   -2.5579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4975   -1.7296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7831   -1.3174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0911   -2.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6793   -1.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0874   -1.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9159   -1.0769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015   -0.6644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2015    0.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0712    1.1566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0712    1.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4975    1.1582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7858    3.2167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0676    2.3929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823    1.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823    1.1577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0686   -0.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7831   -0.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3559    1.1593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0676    3.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4046   -0.4509    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.3282   -1.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9163   -2.5034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3288   -3.2179    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
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  4  3  2  0
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  5  8  1  0
  9  8  1  0
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 19 18  2  0
 14 19  1  0
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 22 16  1  0
 23 22  1  0
 24 23  2  0
 24 25  1  0
 25 26  2  0
 27 26  1  0
 28 27  1  0
  4 28  1  0
 26 29  1  0
 22 29  2  0
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 12 31  1  0
 32 11  2  0
 33 32  1  0
  8 33  2  0
 33 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278865

   ---

Molecule Features

Natural Product: Yes

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: 491.37

Molecular Weight (Monoisotopic): 490.0739

AlogP: 7.33

#Rotatable Bonds: ┄

Polar Surface Area: 80.92

Molecular Species: NEUTRAL

HBA: 4

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.36

CX Basic pKa: ┄

CX LogP: 7.71

CX LogD: 7.39

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.21

Np Likeness Score: 1.43

References

1. Asakawa Y, Ludwiczuk A..  (2018)  Chemical Constituents of Bryophytes: Structures and Biological Activity.,  81  (3): [PMID:29019405] [10.1021/acs.jnatprod.6b01046]

Source

Source(1):

• Scientific Literature