2-ethyl-1-oxo-N'-[(1R,2E,4R)-1,7,7-trimethylbicyclo[2.2.1]hept-2-ylidene]-1,2,3,6,7,7a-hexahydro-3a,6-epoxyisoindole-7-carbohydrazide

ID: ALA4513878

PubChem CID: 155539018

Max Phase: Preclinical

Molecular Formula: C21H29N3O3

Molecular Weight: 371.48

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCN1CC23C=CC(O2)C(C(=O)N/N=C2\C[C@H]4CC[C@]2(C)C4(C)C)C3C1=O

Standard InChI:  InChI=1S/C21H29N3O3/c1-5-24-11-21-9-7-13(27-21)15(16(21)18(24)26)17(25)23-22-14-10-12-6-8-20(14,4)19(12,2)3/h7,9,12-13,15-16H,5-6,8,10-11H2,1-4H3,(H,23,25)/b22-14+/t12-,13?,15?,16?,20+,21?/m1/s1

Standard InChI Key:  WQOAKVNKRSBWFF-KLJRGWRZSA-N

Molfile:  

 
     RDKit          2D

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   26.6962   -9.3251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9420  -10.0168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0003   -9.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6962  -10.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0003  -10.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3878   -9.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3878  -10.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6962   -8.5251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7878   -9.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8170  -10.3293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6878  -11.7835    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.2862   -9.3119    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5713   -9.7237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.8573   -9.3106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1424   -9.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8580   -8.4856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7174   -9.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7123  -10.5411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1452  -10.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4284  -10.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5982  -11.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4200  -11.8553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7580  -11.1011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5654  -10.9316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8308  -12.5708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4166  -13.2843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1294  -10.1793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4169   -9.3043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  1  1  0
  7  6  1  0
  1  8  1  1
  9  2  1  0
 10  2  1  0
  4 11  1  1
  4  5  1  0
  7  4  1  0
  3 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  2  0
 15 28  1  0
 15 19  1  0
 28 17  1  0
 17 18  2  0
 18 20  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 19  1  0
 23 24  2  0
 22 25  1  0
 25 26  1  0
 20 27  1  0
 27 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4513878

   ---

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: 371.48

Molecular Weight (Monoisotopic): 371.2209

AlogP: 2.11

#Rotatable Bonds: 3

Polar Surface Area: 71.00

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.80

CX Basic pKa: 1.62

CX LogP: 1.71

CX LogD: 1.71

Aromatic Rings: ┄

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: 0.26

References

1. Kovaleva KS, Zubkov FI, Bormotov NI, Novikov RA, Dorovatovskii PV, Khrustalev VN, Gatilov YV, Zarubaev VV, Yarovaya OI, Shishkina LN, Salakhutdinov NF..  (2018)  Synthesis of d-(+)-camphor-based N-acylhydrazones and their antiviral activity.,  9  (12): [PMID:30746065] [10.1039/C8MD00442K]

2. Yarovaya OI, Kovaleva KS, Zaykovskaya AA, Yashina LN, Scherbakova NS, Scherbakov DN, Borisevich SS, Zubkov FI, Antonova AS, Peshkov RY, Eltsov IV, Pyankov OV, Maksyutov RA, Salakhutdinov NF..  (2021)  New class of hantaan virus inhibitors based on conjugation of the isoindole fragment to (+)-camphor or (-)-fenchone hydrazonesv.,  40  [PMID:33705902] [10.1016/j.bmcl.2021.127926]

Source

Source(1):

• Scientific Literature