6-Chloromethyl-2-oxo-2H-chromene-3-carboxylic acid 3-chloro-phenyl ester

ID: ALA315567

Chembl Id: CHEMBL315567

Cas Number: 176770-36-8

PubChem CID: 402516

Max Phase: Preclinical

Molecular Formula: C17H10Cl2O4

Molecular Weight: 349.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Oc1cccc(Cl)c1)c1cc2cc(CCl)ccc2oc1=O

Standard InChI:  InChI=1S/C17H10Cl2O4/c18-9-10-4-5-15-11(6-10)7-14(17(21)23-15)16(20)22-13-3-1-2-12(19)8-13/h1-8H,9H2

Standard InChI Key:  RYPFJZFYKSGHCI-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA315567

   2h-1-Benzopyran-3-carboxylic acid, 6-(chloromethyl)-2-oxo-, 3-chlorophenyl ester

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: 349.17

Molecular Weight (Monoisotopic): 347.9956

AlogP: 4.40

#Rotatable Bonds: 3

Polar Surface Area: 56.51

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.60

CX LogD: 4.60

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.30

Np Likeness Score: -0.88

References

1. Pochet L, Doucet C, Schynts M, Thierry N, Boggetto N, Pirotte B, Jiang KY, Masereel B, de Tullio P, Delarge J, Reboud-Ravaux M..  (1996)  Esters and amides of 6-(chloromethyl)-2-oxo-2H-1-benzopyran-3-carboxylic acid as inhibitors of alpha-chymotrypsin: significance of the "aromatic" nature of the novel ester-type coumarin for strong inhibitory activity.,  39  (13): [PMID:8691456] [10.1021/jm960090b]

2. Frédérick R, Robert S, Charlier C, de Ruyck J, Wouters J, Pirotte B, Masereel B, Pochet L..  (2005)  3,6-disubstituted coumarins as mechanism-based inhibitors of thrombin and factor Xa.,  48  (24): [PMID:16302799] [10.1021/jm050448g]

3. Frédérick R, Robert S, Charlier C, Wouters J, Masereel B, Pochet L..  (2007)  Mechanism-based thrombin inhibitors: design, synthesis, and molecular docking of a new selective 2-oxo-2H-1-benzopyran derivative.,  50  (15): [PMID:17580844] [10.1021/jm061368v]

4. Kempen I, Hemmer M, Counerotte S, Pochet L, de Tullio P, Foidart JM, Blacher S, Noël A, Frankenne F, Pirotte B..  (2008)  6-Substituted 2-oxo-2H-1-benzopyran-3-carboxylic acid derivatives in a new approach of the treatment of cancer cell invasion and metastasis.,  43  (12): [PMID:18329754] [10.1016/j.ejmech.2008.01.024]

5. PubChem BioAssay data set, 

6. Hanke S, Tindall CA, Pippel J, Ulbricht D, Pirotte B, Reboud-Ravaux M, Heiker JT, Sträter N..  (2020)  Structural Studies on the Inhibitory Binding Mode of Aromatic Coumarinic Esters to Human Kallikrein-Related Peptidase 7.,  63  (11): [PMID:32374603] [10.1021/acs.jmedchem.9b01806]

7. Costa M, Dias TA, Brito A, Proença F..  (2016)  Biological importance of structurally diversified chromenes.,  123  [PMID:27494166] [10.1016/j.ejmech.2016.07.057]

Source

Source(2):

• Scientific Literature
• PubChem BioAssays