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

ID: ALA4872568

PubChem CID: 155124439

Max Phase: Preclinical

Molecular Formula: C20H21N3O2

Molecular Weight: 335.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(CO)c(CO)c2c3cc4ccccc4cc3c(N(C)C)nn12

Standard InChI:  InChI=1S/C20H21N3O2/c1-12-17(10-24)18(11-25)19-15-8-13-6-4-5-7-14(13)9-16(15)20(22(2)3)21-23(12)19/h4-9,24-25H,10-11H2,1-3H3

Standard InChI Key:  XXFGIUPNRLVHBP-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    2.4708   -4.4863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4696   -5.3058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1777   -5.7148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1759   -4.0774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8845   -4.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8853   -5.3017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5938   -5.7087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5882   -4.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2973   -4.4758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2991   -5.2995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7208   -4.4728    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0059   -4.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7225   -5.2965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0116   -5.7111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1862   -6.5153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0051   -6.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3364   -5.8445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0030   -3.2430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1350   -5.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4168   -7.3037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6421   -7.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2340   -7.3001    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8980   -7.9011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7093   -2.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -2.8368    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
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 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 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4872568

   ---

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: 335.41

Molecular Weight (Monoisotopic): 335.1634

AlogP: 3.00

#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: 1.47

CX LogP: 2.85

CX LogD: 2.85

Aromatic Rings: 4

Heavy Atoms: 25

QED Weighted: 0.57

Np Likeness Score: -0.53

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