7-(1-methyl-1H-pyrazol-4-yl)-10,11-methyleneclioxy-20(S)-camptothecin

ID: ALA5202993

PubChem CID: 146275693

Max Phase: Preclinical

Molecular Formula: C25H20N4O6

Molecular Weight: 472.46

Names and Identifiers

Canonical SMILES:  CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2c-1nc1cc3c(cc1c2-c1cnn(C)c1)OCO3

Standard InChI:  InChI=1S/C25H20N4O6/c1-3-25(32)16-5-18-22-14(9-29(18)23(30)15(16)10-33-24(25)31)21(12-7-26-28(2)8-12)13-4-19-20(35-11-34-19)6-17(13)27-22/h4-8,32H,3,9-11H2,1-2H3/t25-/m0/s1

Standard InChI Key:  BICMKOVYASRDEW-VWLOTQADSA-N

Molfile:  

 
     RDKit          2D

 35 41  0  0  0  0  0  0  0  0999 V2000
   -2.5708    0.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8562    0.5306    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1443    0.1188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1443   -0.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8544   -1.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5708   -0.7099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3586   -0.9659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8456   -0.2955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3586    0.3745    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4265   -1.1203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2849   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2832    0.1172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4316    0.5296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4316    1.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0634    0.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5475   -0.2905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664   -0.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4035   -1.7080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2202   -1.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6974   -1.1241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3616   -0.3748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7721    0.3362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5101   -1.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8456   -1.9508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684   -2.6137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5556   -2.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7611   -2.7447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1805   -2.1642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3422   -3.3247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789   -3.3248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0955    1.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8419    2.6137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0213    2.6137    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2322    1.8331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2525    3.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  1  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  1  9  1  0
  4 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  3 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 11 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  1  0
 21 22  2  0
 20 23  1  0
 24 23  1  0
 25 24  1  0
 26 25  1  0
 19 26  1  0
 26 27  1  0
 27 28  1  0
 26 29  1  1
 25 30  2  0
 31 14  2  0
 31 32  1  0
 32 33  1  0
 33 34  2  0
 34 14  1  0
 32 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5202993

   ---

Molecule Features

Natural Product: No

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: 472.46

Molecular Weight (Monoisotopic): 472.1383

AlogP: 2.21

#Rotatable Bonds: 2

Polar Surface Area: 117.70

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.71

CX Basic pKa: 2.99

CX LogP: 0.92

CX LogD: 0.92

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.39

Np Likeness Score: 0.36

References

1. Zhang G, Yin R, Dai X, Wu G, Qi X, Yu R, Li J, Jiang T..  (2022)  Design, synthesis, and biological evaluation of novel 7-substituted 10,11-methylenedioxy-camptothecin derivatives against drug-resistant small-cell lung cancer in vitro and in vivo.,  241  [PMID:35932565] [10.1016/j.ejmech.2022.114610]

Source

Source(1):

• Scientific Literature