(1R,2S,3S,4S)-3-(2-(3-ethoxy-2-(ethoxycarbonyl)-3-oxoprop-1-enyl)hydrazinecarbonyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

ID: ALA4535945

PubChem CID: 11864300

Max Phase: Preclinical

Molecular Formula: C17H22N2O7

Molecular Weight: 366.37

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)C(=CNNC(=O)[C@@H]1[C@@H](C(=O)O)[C@H]2C=C[C@@H]1C2)C(=O)OCC

Standard InChI:  InChI=1S/C17H22N2O7/c1-3-25-16(23)11(17(24)26-4-2)8-18-19-14(20)12-9-5-6-10(7-9)13(12)15(21)22/h5-6,8-10,12-13,18H,3-4,7H2,1-2H3,(H,19,20)(H,21,22)/t9-,10+,12+,13+/m1/s1

Standard InChI Key:  VOSGPWWQFGKLTJ-URBCHYCLSA-N

Molfile:  

 
     RDKit          2D

 28 29  0  0  0  0  0  0  0  0999 V2000
   17.1528   -4.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1528   -5.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8580   -5.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5633   -5.5841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5633   -4.7669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8580   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8580   -3.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5657   -3.1284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1503   -3.1284    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4439   -4.3604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4415   -3.5432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7374   -4.7711    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0284   -4.3646    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3219   -4.7752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6130   -4.3687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9065   -4.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6106   -3.5515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3172   -3.1409    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9017   -3.1450    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8993   -2.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1904   -1.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1976   -4.3729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9089   -5.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4911   -4.7835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7822   -4.3770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7099   -4.8784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3922   -5.8831    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.2022   -4.2573    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  1
  7  8  2  0
  7  9  1  0
  1 10  1  6
 10 11  2  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 16 22  1  0
 16 23  2  0
 22 24  1  0
 24 25  1  0
  2 26  1  0
  5 26  1  0
  2 27  1  6
  5 28  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA4535945

   (1R,2S,3S,4S)-3-[[(3-ethoxy-2-ethoxycarbonyl-3-oxoprop-1-enyl)amino]carbamoyl]bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

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: 366.37

Molecular Weight (Monoisotopic): 366.1427

AlogP: 0.14

#Rotatable Bonds: 8

Polar Surface Area: 131.03

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.76

CX Basic pKa: ┄

CX LogP: 0.53

CX LogD: -2.75

Aromatic Rings: ┄

Heavy Atoms: 26

QED Weighted: 0.14

Np Likeness Score: -0.33

References

1. Ruiz V, Czyzyk DJ, Valhondo M, Jorgensen WL, Anderson KS..  (2019)  Novel allosteric covalent inhibitors of bifunctional Cryptosporidium hominis TS-DHFR from parasitic protozoa identified by virtual screening.,  29  (11): [PMID:30929953] [10.1016/j.bmcl.2019.03.022]

Source

Source(1):

• Scientific Literature