ID: ALA5278089

Max Phase: Preclinical

Molecular Formula: C21H18N2O4S

Molecular Weight: 394.45

Names and Identifiers

Canonical SMILES:  CC[C@@]1(O)C(=O)OCc2c1cc1n(c2=O)Cc2c-1nc1ccccc1c2CS

Standard InChI:  InChI=1S/C21H18N2O4S/c1-2-21(26)15-7-17-18-12(8-23(17)19(24)13(15)9-27-20(21)25)14(10-28)11-5-3-4-6-16(11)22-18/h3-7,26,28H,2,8-10H2,1H3/t21-/m0/s1

Standard InChI Key:  UBRXAFRHRLKFID-NRFANRHFSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
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   -3.2202    0.2974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5048   -0.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7913    0.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0758   -0.1102    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3623    0.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4228    0.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7600   -0.7023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5807   -0.7867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9179   -1.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1177   -1.7410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7386   -1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0758   -2.3769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2219   -0.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8847   -0.2026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0641   -0.1182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7269    0.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2104    1.3031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9062    0.7190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4198    1.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3641    1.1288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794    1.5397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7931    1.1255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5085    1.5365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9179   -2.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6326   -2.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794    2.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3648    2.7775    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
  9 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
  7 19  1  0
 19 20  1  0
 20 21  1  0
  6 21  1  0
 21 22  2  0
 22 23  1  0
  4 23  2  0
 23 24  1  0
 24  1  2  0
 10 25  1  0
 25 26  1  0
 22 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5278089

   ---

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: 394.45

Molecular Weight (Monoisotopic): 394.0987

AlogP: 2.51

#Rotatable Bonds: 2

Polar Surface Area: 81.42

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.91

CX Basic pKa: 3.00

CX LogP: 1.70

CX LogD: 1.70

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.40

Np Likeness Score: 0.93

References

1. Khaiwa N, Maarouf NR, Darwish MH, Alhamad DWM, Sebastian A, Hamad M, Omar HA, Orive G, Al-Tel TH..  (2021)  Camptothecin's journey from discovery to WHO Essential Medicine: Fifty years of promise.,  223  [PMID:34175539] [10.1016/j.ejmech.2021.113639]

Source

Source(1):

• Scientific Literature