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

ID: ALA4874361

PubChem CID: 155124447

Max Phase: Preclinical

Molecular Formula: C22H23N3O2

Molecular Weight: 361.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Cc1c(CO)c(CO)c2c3cc4ccccc4cc3c(N3CCCC3)nn12

Standard InChI:  InChI=1S/C22H23N3O2/c1-14-19(12-26)20(13-27)21-17-10-15-6-2-3-7-16(15)11-18(17)22(23-25(14)21)24-8-4-5-9-24/h2-3,6-7,10-11,26-27H,4-5,8-9,12-13H2,1H3

Standard InChI Key:  SEKXKZGJJQQVFM-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   11.4629   -5.2398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1709   -5.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1691   -4.0114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8778   -4.4166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8785   -5.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5871   -5.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5815   -4.0064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2906   -4.4098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2923   -5.2335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7140   -4.4067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9991   -3.9941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7157   -5.2305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0049   -5.6451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1794   -6.4493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9983   -6.5317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3296   -5.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9963   -3.1769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1282   -5.6051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4100   -7.2376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6353   -7.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2272   -7.2340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8912   -7.8350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6545   -2.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3993   -1.9203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5820   -1.9231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3324   -2.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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 26 27  1  0
 27 18  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874361

   ---

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: 361.45

Molecular Weight (Monoisotopic): 361.1790

AlogP: 3.53

#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: 3.26

CX LogD: 3.26

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.55

Np Likeness Score: -0.58

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