1-(4-chlorophenyl)-3-(((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)thiourea

ID: ALA4643091

PubChem CID: 156016247

Max Phase: Preclinical

Molecular Formula: C27H29ClN4S

Molecular Weight: 477.08

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C27H29ClN4S/c1-2-27-13-5-14-31-15-12-22-21-6-3-4-7-23(21)32(24(22)25(27)31)20(16-27)17-29-26(33)30-19-10-8-18(28)9-11-19/h3-4,6-11,16,25H,2,5,12-15,17H2,1H3,(H2,29,30,33)/t25-,27+/m1/s1

Standard InChI Key:  ZUBAGCFQKUERTB-VPUSJEBWSA-N

Molfile:  

 
     RDKit          2D

 34 39  0  0  0  0  0  0  0  0999 V2000
   35.3148  -10.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7254  -10.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0201  -10.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3148  -11.3492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6159  -12.5679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3212  -12.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0162  -11.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0264  -12.5644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7297  -12.9587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4273  -12.5468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.4171  -11.7360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7092  -11.3373    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   34.6165  -11.7580    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.9087  -12.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.0619  -10.9527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5337  -10.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1954   -9.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3856   -9.4757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9152  -10.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2561  -10.8786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0101  -10.9330    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   36.0183  -13.3805    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7220  -13.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9096  -13.7945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2023  -14.2038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4942  -13.7960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.2032  -15.0210    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   31.7869  -14.2054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0818  -13.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3751  -14.2061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3756  -15.0242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0887  -15.4318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7925  -15.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6688  -15.4345    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
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  9 10  1  0
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  5 14  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  7 21  1  6
  8 22  1  6
 22 23  1  0
 14 24  1  0
 24 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:

   

   ALA4643091

   ---

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: 477.08

Molecular Weight (Monoisotopic): 476.1801

AlogP: 6.23

#Rotatable Bonds: 4

Polar Surface Area: 32.23

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.38

CX Basic pKa: 7.17

CX LogP: 5.97

CX LogD: 5.77

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.44

Np Likeness Score: -0.28

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