(1S,4R)-3-(4-Ethoxycarbonyl-phenylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

ID: ALA367750

Chembl Id: CHEMBL367750

PubChem CID: 44386616

Max Phase: Preclinical

Molecular Formula: C17H17NO6

Molecular Weight: 331.32

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1ccc(NC(=O)C2C(C(=O)O)[C@@H]3C=C[C@H]2O3)cc1

Standard InChI:  InChI=1S/C17H17NO6/c1-2-23-17(22)9-3-5-10(6-4-9)18-15(19)13-11-7-8-12(24-11)14(13)16(20)21/h3-8,11-14H,2H2,1H3,(H,18,19)(H,20,21)/t11-,12+,13?,14?/m1/s1

Standard InChI Key:  GZJXQUIAUKSDDS-KBHBFKLGSA-N

Alternative Forms

1. Parent:

   

   ALA367750

   (1S,4R)-3-(4-Ethoxycarbonyl-phenylcarbamoyl)-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 331.32

Molecular Weight (Monoisotopic): 331.1056

AlogP: 1.46

#Rotatable Bonds: 5

Polar Surface Area: 101.93

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.70

CX Basic pKa: ┄

CX LogP: 1.56

CX LogD: -1.75

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.63

Np Likeness Score: -0.50

References

1. Hart ME, Chamberlin AR, Walkom C, Sakoff JA, McCluskey A..  (2004)  Modified norcantharidins; synthesis, protein phosphatases 1 and 2A inhibition, and anticancer activity.,  14  (8): [PMID:15050639] [10.1016/j.bmcl.2004.01.093]

Source

Source(1):

• Scientific Literature