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

ID: ALA4854342

PubChem CID: 164613463

Max Phase: Preclinical

Molecular Formula: C22H23N3O3

Molecular Weight: 377.44

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(CO)c(CO)c2c3cc4ccccc4cc3c(N3CCOCC3)nn12

Standard InChI:  InChI=1S/C22H23N3O3/c1-14-19(12-26)20(13-27)21-17-10-15-4-2-3-5-16(15)11-18(17)22(23-25(14)21)24-6-8-28-9-7-24/h2-5,10-11,26-27H,6-9,12-13H2,1H3

Standard InChI Key:  IUTQEYIIYMIJHJ-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   29.0696   -5.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7777   -5.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.7759   -4.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4845   -4.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4853   -5.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1938   -5.7913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1882   -4.1550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8973   -4.5583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8991   -5.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3207   -4.5553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6059   -4.1427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3225   -5.3791    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.6116   -5.7936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7862   -6.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6051   -6.6803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9364   -5.9271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6030   -3.3255    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.7350   -5.7536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0168   -7.3862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2420   -7.2075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8340   -7.3826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.4979   -7.9836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.3132   -2.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3123   -2.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.6050   -1.6935    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.8969   -2.1033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8961   -2.9231    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:

   

   ALA4854342

   ---

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: 377.44

Molecular Weight (Monoisotopic): 377.1739

AlogP: 2.77

#Rotatable Bonds: 3

Polar Surface Area: 70.23

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.35

CX LogP: 2.63

CX LogD: 2.63

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -0.74

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