epi-koumidine

ID: ALA4875420

Cas Number: 124096-81-7

PubChem CID: 13946377

Max Phase: Preclinical

Molecular Formula: C19H22N2O

Molecular Weight: 294.40

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C1\CN2[C@H]3C[C@@H]1[C@@H](CO)[C@@H]2Cc1c3[nH]c2ccccc12

Standard InChI:  InChI=1S/C19H22N2O/c1-2-11-9-21-17-8-14-12-5-3-4-6-16(12)20-19(14)18(21)7-13(11)15(17)10-22/h2-6,13,15,17-18,20,22H,7-10H2,1H3/b11-2+/t13-,15+,17-,18-/m0/s1

Standard InChI Key:  VXTDUGOBAOLMED-FFMDXNROSA-N

Molfile:  

 
     RDKit          2D

 25 29  0  0  0  0  0  0  0  0999 V2000
   19.0504  -23.4943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7634  -23.0841    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7634  -22.2596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0504  -21.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3417  -23.0841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3369  -22.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5512  -23.3472    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0602  -22.6789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5443  -22.0058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2071  -21.2517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3862  -21.1696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9035  -21.8477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2434  -22.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0424  -24.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4741  -23.4996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4728  -24.3242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7559  -23.9002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3331  -23.9002    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.5380  -24.6949    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   20.8844  -25.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7132  -25.0404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4694  -22.6740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7662  -21.4350    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   21.2703  -22.4624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8534  -23.0456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0
  5  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  5  6  2  0
  6  9  1  0
  8  7  1  0
  7  5  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  8  1  0
  1 14  1  0
  2 15  1  0
 15 16  1  0
 14 17  1  0
 16 17  1  0
  1 18  1  6
 17 19  1  1
 16 20  2  0
 20 21  1  0
  3 22  1  0
 17 22  1  0
  3 23  1  6
 22 24  1  6
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4875420

   16-Epikoumidine

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: 294.40

Molecular Weight (Monoisotopic): 294.1732

AlogP: 3.02

#Rotatable Bonds: 1

Polar Surface Area: 39.26

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.48

CX LogP: 2.21

CX LogD: 2.16

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.79

Np Likeness Score: 2.15

References

1. Jin P, Zhan G, Zheng G, Liu J, Peng X, Huang L, Gao B, Yuan X, Yao G..  (2021)  Gelstriamine A, a Triamino Monoterpene Indole Alkaloid with a Caged 6/5/7/6/6/5 Scaffold and Analgesic Alkaloids from Gelsemium elegans Stems.,  84  (4.0): [PMID:33826318] [10.1021/acs.jnatprod.1c00062]

Source

Source(1):

• Scientific Literature