Ajmalicine

ID: ALA5086982

PubChem CID: 3010369

Max Phase: Preclinical

Molecular Formula: C20H22N2O3

Molecular Weight: 338.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C1=COC[C@H]2CN3CCc4c([nH]c5ccccc45)[C@@H]3C[C@H]12

Standard InChI:  InChI=1S/C20H22N2O3/c1-24-20(23)16-11-25-10-12-9-22-7-6-14-13-4-2-3-5-17(13)21-19(14)18(22)8-15(12)16/h2-5,11-12,15,18,21H,6-10H2,1H3/t12-,15+,18+/m1/s1

Standard InChI Key:  SFLBNAROMBKKJF-MRAWALMUSA-N

Molfile:  

 
     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
   10.7583  -13.2979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7571  -14.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4652  -14.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4634  -12.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1720  -13.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1723  -14.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9552  -14.3716    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9548  -13.0397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4390  -13.7069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1076  -12.2031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2859  -12.2874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5918  -12.8702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2502  -13.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7284  -14.2910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4115  -12.7861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8345  -14.3256    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.8920  -13.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5486  -14.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0221  -14.8764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8414  -14.8021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1848  -14.0539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7090  -13.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2943  -12.7490    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.3327  -14.9942    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.6802  -15.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8664  -15.6936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5245  -16.4358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1520  -16.2858    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  9  1  0
  8  5  1  0
  8  9  2  0
  8 11  1  0
  9 13  1  0
 12 10  1  0
 10 11  1  0
 12 13  1  0
 12 15  1  0
 13 14  1  0
 14 18  1  0
 17 15  1  0
 13 16  1  6
 17 18  1  0
 17 22  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 17 23  1  1
 18 24  1  6
 19 25  1  0
 25 26  1  0
 26 27  1  0
 25 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5086982

   Oxayohimban-16-carboxylic acid, 16,17-didehydro-, methyl ester

Molecule Features

Natural Product: Yes

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: 338.41

Molecular Weight (Monoisotopic): 338.1630

AlogP: 2.79

#Rotatable Bonds: 1

Polar Surface Area: 54.56

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.13

CX LogP: 2.14

CX LogD: 1.95

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.81

Np Likeness Score: 0.98

References

1. León F, Obeng S, Mottinelli M, Chen Y, King TI, Berthold EC, Kamble SH, Restrepo LF, Patel A, Gamez-Jimenez LR, Lopera-Londoño C, Hiranita T, Sharma A, Hampson AJ, Canal CE, McMahon LR, McCurdy CR..  (2021)  Activity of Mitragyna speciosa ("Kratom") Alkaloids at Serotonin Receptors.,  64  (18.0): [PMID:34467758] [10.1021/acs.jmedchem.1c00726]

Source

Source(1):

• Scientific Literature