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-bromophenylcarbamothioate

ID: ALA4644378

PubChem CID: 156018586

Max Phase: Preclinical

Molecular Formula: C27H28BrN3OS

Molecular Weight: 522.51

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H28BrN3OS/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:  FBFFKROFZXOLDE-VPUSJEBWSA-N

Molfile:  

 
     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   21.0635  -15.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4741  -15.5507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7688  -15.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0635  -16.3679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3646  -17.5866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0699  -17.9911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7648  -16.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7750  -17.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4783  -17.9774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1760  -17.5655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1658  -16.7548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4579  -16.3560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3651  -16.7767    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.6573  -17.9960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9492  -17.5882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8106  -15.9714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2824  -15.3086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9441  -14.5707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1343  -14.4944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6639  -15.1621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0048  -15.8973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7587  -15.9517    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.7670  -18.3992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4707  -18.8147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2419  -17.9976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5338  -17.5898    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2428  -18.8148    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.8265  -17.9992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1190  -17.5888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4122  -17.9975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4127  -18.8155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1258  -19.2232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8297  -18.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7060  -19.2258    0.0000 Br  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:

   

   ALA4644378

   ---

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: 522.51

Molecular Weight (Monoisotopic): 521.1136

AlogP: 6.76

#Rotatable Bonds: 4

Polar Surface Area: 29.43

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 6.53

CX Basic pKa: 7.22

CX LogP: 6.09

CX LogD: 6.01

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.38

Np Likeness Score: 0.15

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