Akuammiline

ID: ALA4874877

PubChem CID: 164625689

Max Phase: Preclinical

Molecular Formula: C23H26N2O4

Molecular Weight: 394.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  C/C=C1/CN2CC[C@]34C(=Nc5ccccc53)[C@@H]2C[C@@H]1[C@@]4(COC(C)=O)C(=O)OC

Standard InChI:  InChI=1S/C23H26N2O4/c1-4-15-12-25-10-9-22-16-7-5-6-8-18(16)24-20(22)19(25)11-17(15)23(22,21(27)28-3)13-29-14(2)26/h4-8,17,19H,9-13H2,1-3H3/b15-4-/t17-,19-,22+,23-/m0/s1

Standard InChI Key:  QBHALCZZZWCCLV-XIPRXZKPSA-N

Molfile:  

 
     RDKit          2D

 31 35  0  0  0  0  0  0  0  0999 V2000
    9.6644  -11.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2788  -12.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6498  -12.8451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4169  -11.5408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7869  -12.1997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3929  -12.8534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8983  -13.4262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5298  -12.3682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6008  -13.1269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8446  -12.2403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1477  -11.9199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9198  -12.9966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.2982  -13.4449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3725  -14.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6916  -14.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6157  -13.3103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3722  -14.3854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4464  -15.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6416  -13.8150    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.5240  -11.6099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8751  -10.9469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6317  -10.9233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4767  -10.3091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0301  -11.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0208  -13.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0174  -14.5719    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.8212  -11.2028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8230  -10.3988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1259   -9.9953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1276   -9.1871    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4271  -10.3957    0.0000 C   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  2  0
  8  5  1  0
  8  9  1  0
  8 11  1  6
  9 13  1  0
 12 10  1  0
 10 11  1  0
 12 13  1  0
 12 16  1  0
 13 14  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 13 19  1  6
  8 20  1  0
 20 21  1  6
 21 22  1  0
 21 23  2  0
 22 24  1  0
 14 25  1  0
 15 25  1  0
 25 20  1  0
 25 26  1  1
 20 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4874877

   ---

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: 394.47

Molecular Weight (Monoisotopic): 394.1893

AlogP: 2.79

#Rotatable Bonds: 3

Polar Surface Area: 68.20

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.00

CX LogP: 2.65

CX LogD: 2.51

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: 2.38

References

1. Creed SM, Gutridge AM, Argade MD, Hennessy MR, Friesen JB, Pauli GF, van Rijn RM, Riley AP..  (2021)  Isolation and Pharmacological Characterization of Six Opioidergic Picralima nitida Alkaloids.,  84  (1.0): [PMID:33326237] [10.1021/acs.jnatprod.0c01036]

Source

Source(1):

• Scientific Literature