O-(2,2,2-trifluoroethyl)-N-[(7S)-1,2,3-trimethoxy-10-(methylamino)-9-oxo-6,7-dihydro-5H-benzo[a]heptalen-7-yl]carbamothioate

ID: ALA4863822

PubChem CID: 164618748

Max Phase: Preclinical

Molecular Formula: C23H25F3N2O5S

Molecular Weight: 498.52

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CNc1ccc2c(cc1=O)[C@@H](NC(=S)OCC(F)(F)F)CCc1cc(OC)c(OC)c(OC)c1-2

Standard InChI:  InChI=1S/C23H25F3N2O5S/c1-27-16-8-6-13-14(10-17(16)29)15(28-22(34)33-11-23(24,25)26)7-5-12-9-18(30-2)20(31-3)21(32-4)19(12)13/h6,8-10,15H,5,7,11H2,1-4H3,(H,27,29)(H,28,34)/t15-/m0/s1

Standard InChI Key:  RUSWNRCVEJTRDQ-HNNXBMFYSA-N

Molfile:  

 
     RDKit          2D

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   39.5794   -2.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5783   -3.4056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2870   -3.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.2852   -2.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9979   -3.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9986   -2.5810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6450   -2.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4516   -2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.8071   -2.9880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6449   -3.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4539   -3.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1076   -4.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2818   -4.6738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.1128   -5.0861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.6478   -5.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.4624   -5.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6472   -6.4004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.0453   -6.9614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.8509   -5.4411    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.6258   -2.9862    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   40.2879   -4.6360    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8696   -3.8164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8710   -2.1776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.8708   -1.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1614   -3.4045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5799   -5.0440    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.0356   -2.2727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.8584   -2.2709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.6226   -1.5611    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   45.2713   -2.9826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.0941   -2.9808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.5071   -3.6924    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   46.5039   -2.2673    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   46.9152   -2.9794    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  5  2  0
  6  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  5 10  1  0
  7  8  1  0
  8  9  1  0
 11  9  1  0
 10 11  1  0
 11 12  2  0
 10 13  2  0
 12 14  1  0
 13 15  1  0
 14 16  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 14 19  2  0
  9 20  1  6
  3 21  1  0
  2 22  1  0
  1 23  1  0
 23 24  1  0
 22 25  1  0
 21 26  1  0
 20 27  1  0
 27 28  1  0
 27 29  2  0
 28 30  1  0
 30 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4863822

   ---

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: 498.52

Molecular Weight (Monoisotopic): 498.1436

AlogP: 4.22

#Rotatable Bonds: 6

Polar Surface Area: 78.05

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.45

CX Basic pKa: 3.80

CX LogP: 3.61

CX LogD: 3.58

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.57

Np Likeness Score: 0.14

References

1. Krzywik J, Aminpour M, Janczak J, Maj E, Moshari M, Mozga W, Wietrzyk J, Tuszyński JA, Huczyński A..  (2021)  An insight into the anticancer potential of carbamates and thiocarbamates of 10-demethoxy-10-methylaminocolchicine.,  215  [PMID:33611191] [10.1016/j.ejmech.2021.113282]

Source

Source(1):

• Scientific Literature