O-((41S,13aS)-13a-ethyl-2,3,41,5,6,13a-hexahydro-1H-indolo[3,2,1-de]pyrido[3,2,1-ij][1,5]naphthyridin-12-yl)methyl 4-chlorophenylcarbamothioate

ID: ALA4649811

PubChem CID: 156022181

Max Phase: Preclinical

Molecular Formula: C27H28ClN3OS

Molecular Weight: 478.06

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC[C@@]12C=C(COC(=S)Nc3ccc(Cl)cc3)n3c4c(c5ccccc53)CCN(CCC1)[C@H]42

Standard InChI:  InChI=1S/C27H28ClN3OS/c1-2-27-13-5-14-30-15-12-22-21-6-3-4-7-23(21)31(24(22)25(27)30)20(16-27)17-32-26(33)29-19-10-8-18(28)9-11-19/h3-4,6-11,16,25H,2,5,12-15,17H2,1H3,(H,29,33)/t25-,27+/m1/s1

Standard InChI Key:  OITYKNRSRKZAOQ-VPUSJEBWSA-N

Molfile:  

 
     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   10.2838  -22.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7116  -22.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9978  -22.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2838  -23.8084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5764  -25.0421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2902  -25.4514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9937  -24.2179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0040  -25.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7159  -25.4377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4221  -25.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4118  -24.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6953  -23.7964    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5769  -24.2223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8604  -25.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1435  -25.0437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0155  -23.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4931  -22.7362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1506  -21.9892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3309  -21.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8548  -22.5879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1999  -23.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9875  -23.3872    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.9959  -25.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7082  -26.2852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4277  -25.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7108  -25.0452    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4286  -26.2852    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.9949  -25.4596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2787  -25.0442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5633  -25.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5637  -26.2860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2856  -26.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9981  -26.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8484  -26.7013    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  4  2  0
  1  3  1  0
 12  2  1  0
  2  3  1  0
  7  4  1  0
 13  5  1  0
  5  6  2  0
  6  8  1  0
  7  8  1  0
  7 12  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 13  4  1  0
  1 17  1  0
 16 13  1  0
  5 14  1  0
 14 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  7 22  1  6
  8 23  1  6
 23 24  1  0
 15 25  1  0
 25 26  1  0
 25 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 33  2  0
 33 28  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4649811

   ---

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: 478.06

Molecular Weight (Monoisotopic): 477.1642

AlogP: 6.65

#Rotatable Bonds: 4

Polar Surface Area: 29.43

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.52

CX Basic pKa: 7.22

CX LogP: 5.92

CX LogD: 5.84

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.43

Np Likeness Score: 0.07

References

1. Pan BW, Shi Y, Li WC, Wang Q, Pan M, Wu Q, Fu HZ..  (2020)  Synthesis and biological evaluation of Vinpocetine derivatives.,  30  (2): [PMID:31859156] [10.1016/j.bmcl.2019.05.052]

Source

Source(1):

• Scientific Literature