Buphanisine-N-oxide

ID: ALA4475266

PubChem CID: 155537507

Max Phase: Preclinical

Molecular Formula: C17H19NO4

Molecular Weight: 301.34

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CO[C@H]1C=C[C@@]23CC[N@@+]([O-])(Cc4cc5c(cc42)OCO5)[C@@H]3C1

Standard InChI:  InChI=1S/C17H19NO4/c1-20-12-2-3-17-4-5-18(19,16(17)7-12)9-11-6-14-15(8-13(11)17)22-10-21-14/h2-3,6,8,12,16H,4-5,7,9-10H2,1H3/t12-,16+,17+,18+/m0/s1

Standard InChI Key:  TWWZIVWNWSQGQA-FCRVUTKVSA-N

Molfile:  

 
     RDKit          2D

 23 27  0  0  0  0  0  0  0  0999 V2000
    9.7238  -24.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0345  -25.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4171  -25.8571    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4171  -25.0688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0345  -25.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3535  -24.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7238  -26.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4047  -24.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6643  -25.0605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6643  -25.8571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3535  -26.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1064  -24.6767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0940  -25.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9090  -24.8212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9131  -26.1088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4426  -25.4691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1188  -23.8719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6453  -25.2669    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.8319  -23.4729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5340  -23.8909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7279  -23.8636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4295  -23.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4130  -26.6743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  4  1  0
  4  1  1  0
  5  2  1  0
 21  1  1  0
  6  2  2  0
  7  3  1  0
  1  8  1  1
  9  6  1  0
 10 11  1  0
 11  5  2  0
 12  4  1  0
 13  8  1  0
 14  9  1  0
 15 10  1  0
 16 14  1  0
 17 22  1  0
  4 18  1  6
  3 13  1  1
 12 17  1  0
  5  7  1  0
  9 10  2  0
 16 15  1  0
 17 19  1  6
 19 20  1  0
 22 21  2  0
  3 23  1  0
M  CHG  2   3   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4475266

   ---

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: 301.34

Molecular Weight (Monoisotopic): 301.1314

AlogP: 2.23

#Rotatable Bonds: 1

Polar Surface Area: 50.75

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.28

CX LogP: 0.62

CX LogD: 0.62

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.45

Np Likeness Score: 2.47

References

1. Nair JJ, van Staden J..  (2019)  Antiprotozoal alkaloid principles of the plant family Amaryllidaceae.,  29  (20): [PMID:31515186] [10.1016/j.bmcl.2019.126642]

Source

Source(1):

• Scientific Literature