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 methylcarbamothioate

ID: ALA4649020

PubChem CID: 156020637

Max Phase: Preclinical

Molecular Formula: C22H27N3OS

Molecular Weight: 381.55

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C22H27N3OS/c1-3-22-10-6-11-24-12-9-17-16-7-4-5-8-18(16)25(19(17)20(22)24)15(13-22)14-26-21(27)23-2/h4-5,7-8,13,20H,3,6,9-12,14H2,1-2H3,(H,23,27)/t20-,22+/m1/s1

Standard InChI Key:  CCPUIFJVAYRRAS-IRLDBZIGSA-N

Molfile:  

 
     RDKit          2D

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   23.2386   -2.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6491   -2.9998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9438   -2.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2386   -3.8170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5396   -5.0357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2449   -5.4402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9399   -4.2215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9501   -5.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6534   -5.4265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3510   -5.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3408   -4.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6330   -3.8051    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.5402   -4.2258    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.8324   -5.4451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1242   -5.0373    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9856   -3.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4574   -2.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1191   -2.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3093   -1.9435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8390   -2.6112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1799   -3.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9338   -3.4008    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.9421   -5.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6457   -6.2638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4170   -5.4467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7088   -5.0389    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4179   -6.2639    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.0016   -5.4482    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA4649020

   ---

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: 381.55

Molecular Weight (Monoisotopic): 381.1875

AlogP: 4.11

#Rotatable Bonds: 3

Polar Surface Area: 29.43

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.81

CX Basic pKa: 7.07

CX LogP: 3.98

CX LogD: 3.90

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.81

Np Likeness Score: 0.64

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