ID: ALA5195921

PubChem CID: 168284333

Max Phase: Preclinical

Molecular Formula: C20H26N2O5

Molecular Weight: 374.44

Names and Identifiers

Canonical SMILES:  C[C@@H]1CC[C@H]2[C@@H](C)C(=O)N(/N=C/c3ccco3)[C@@H]3O[C@@]4(C)CC[C@@H]1[C@@]23OO4

Standard InChI:  InChI=1S/C20H26N2O5/c1-12-6-7-16-13(2)17(23)22(21-11-14-5-4-10-24-14)18-20(16)15(12)8-9-19(3,25-18)26-27-20/h4-5,10-13,15-16,18H,6-9H2,1-3H3/b21-11+/t12-,13-,15+,16+,18-,19-,20-/m1/s1

Standard InChI Key:  YYOQSSWNRRRBCA-GEBNUDIDSA-N

Molfile:  

 
     RDKit          2D

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    0.6617   -0.1860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3671    0.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6654    0.4885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529    1.2030    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4615    0.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2865    0.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1378    0.0281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0663    1.5189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7443    1.6610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3671    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3671    1.9393    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813    1.5267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813    2.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7957    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7957    0.2895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813   -0.1228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7959   -0.5354    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0813   -0.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7958   -1.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3670   -1.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3670   -2.1851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6617   -0.9477    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618   -1.3602    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7762   -0.9477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4907   -1.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5769   -2.1803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3836   -2.3517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7959   -1.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2441   -1.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  6
  5  4  1  0
  6  5  1  6
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  8  2  1  0
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  9 10  1  0
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 11 13  1  0
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 15 13  1  0
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 17 16  1  0
 17  3  1  0
 17 18  1  6
 17 19  1  0
 19 20  1  1
 21 19  1  0
 21 22  2  0
 23 21  1  0
  2 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 27 26  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 26  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA5195921

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 374.44

Molecular Weight (Monoisotopic): 374.1842

AlogP: 3.31

#Rotatable Bonds: 2

Polar Surface Area: 73.50

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.58

CX LogD: 3.58

Aromatic Rings: 1

Heavy Atoms: 27

QED Weighted: 0.59

Np Likeness Score: 1.51

References

1. Karnatak M, Hassam M, Singh AS, Yadav DK, Singh C, Puri SK, Verma VP..  (2022)  Novel hydrazone derivatives of N-amino-11-azaartemisinin with high order of antimalarial activity against multidrug-resistant Plasmodium yoelii nigeriensis in Swiss mice via intramuscular route.,  58  [PMID:34974111] [10.1016/j.bmcl.2021.128522]

Source

Source(1):

• Scientific Literature