(3-methyl-6-(piperidin-1-yl)benzo[g]pyrrolo[2,1-a]phthalazine-1,2-diyl)dimethanol

ID: ALA4869983

PubChem CID: 164621088

Max Phase: Preclinical

Molecular Formula: C23H25N3O2

Molecular Weight: 375.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(CO)c(CO)c2c3cc4ccccc4cc3c(N3CCCCC3)nn12

Standard InChI:  InChI=1S/C23H25N3O2/c1-15-20(13-27)21(14-28)22-18-11-16-7-3-4-8-17(16)12-19(18)23(24-26(15)22)25-9-5-2-6-10-25/h3-4,7-8,11-12,27-28H,2,5-6,9-10,13-14H2,1H3

Standard InChI Key:  GCLZLXFTQSVIBF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   20.2621   -5.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9702   -6.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9684   -4.5355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6770   -4.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6778   -5.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3863   -6.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3807   -4.5305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0898   -4.9339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0916   -5.7576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5132   -4.9309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7984   -4.5183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5150   -5.7546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8041   -6.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9787   -6.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7976   -7.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1289   -6.3026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7955   -3.7011    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9275   -6.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2093   -7.7618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4345   -7.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0265   -7.7582    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6904   -8.3592    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5057   -3.2926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5048   -2.4790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7975   -2.0690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0894   -2.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0886   -3.2987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
  9 12  1  0
 10 14  1  0
 13 11  1  0
 11 12  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
 12 18  1  0
 17 19  1  0
 16 20  1  0
 15 21  1  0
 20 22  1  0
 21 23  1  0
 18 24  1  0
 18 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4869983

   ---

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: 375.47

Molecular Weight (Monoisotopic): 375.1947

AlogP: 3.92

#Rotatable Bonds: 3

Polar Surface Area: 61.00

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.40

CX LogP: 3.70

CX LogD: 3.70

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.53

Np Likeness Score: -0.57

References

1. Chen TL, Patel AS, Jain V, Kuppusamy R, Lin YW, Hou MH, Su TL, Lee TC..  (2021)  Discovery of Oral Anticancer 1,2-Bis(hydroxymethyl)benzo[g]pyrrolo[2,1-a]phthalazine Hybrids That Inhibit Angiogenesis and Induce DNA Cross-Links.,  64  (17.0): [PMID:34459195] [10.1021/acs.jmedchem.0c01733]

Source

Source(1):

• Scientific Literature