((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)methanol

ID: ALA4646903

PubChem CID: 12306934

Max Phase: Preclinical

Molecular Formula: C20H24N2O

Molecular Weight: 308.43

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C20H24N2O/c1-2-20-9-5-10-21-11-8-16-15-6-3-4-7-17(15)22(14(12-20)13-23)18(16)19(20)21/h3-4,6-7,12,19,23H,2,5,8-11,13H2,1H3/t19-,20+/m1/s1

Standard InChI Key:  FSCZUIZDBMJVDY-UXHICEINSA-N

Molfile:  

 
     RDKit          2D

 24 28  0  0  0  0  0  0  0  0999 V2000
    4.9673   -2.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3779   -2.8471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6726   -2.4343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9673   -3.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2684   -4.8830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9737   -5.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6686   -4.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6789   -4.8795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3821   -5.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0798   -4.8619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0696   -4.0511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3617   -3.6524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2689   -4.0731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5612   -5.2924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8530   -4.8846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7144   -3.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1862   -2.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8479   -1.8671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0381   -1.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5677   -2.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9086   -3.1937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6626   -3.2481    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6708   -5.6956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3745   -6.1111    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
M  END

Alternative Forms

1. Parent:

   

   ALA4646903

   [(15S,19S)-15-ethyl-1,11-diazapentacyclo[9.6.2.02,7.08,18.015,19]nonadeca-2,4,6,8(18),16-pentaen-17-yl]methanol

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: 308.43

Molecular Weight (Monoisotopic): 308.1889

AlogP: 3.58

#Rotatable Bonds: 2

Polar Surface Area: 28.40

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.08

CX LogP: 2.86

CX LogD: 2.69

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.92

Np Likeness Score: 1.04

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]

2. Wang J,Lv X,Xu J,Liu X,Du T,Sun G,Chen J,Shen X,Wang J,Hu L.  (2020)  Design, synthesis and biological evaluation of vincamine derivatives as potential pancreatic β-cells protective agents for the treatment of type 2 diabetes mellitus.,  188  [PMID:31918073] [10.1016/j.ejmech.2019.111976]

Source

Source(1):

• Scientific Literature