2-Oxo-2H-chromene-3-carboxylic acid benzyl ester

ID: ALA180436

Chembl Id: CHEMBL180436

Cas Number: 324065-51-2

PubChem CID: 562728

Max Phase: Preclinical

Molecular Formula: C17H12O4

Molecular Weight: 280.28

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Coumarin-3-Carboxylic Acid Benzyl Ester | Benzyl 2-oxo-2H-chromene-3-carboxylate|324065-51-2|CHEMBL180436|Coumarin-3-Carboxylic Acid Benzyl Ester|2H-1-Benzopyran-3-carboxylic acid, 2-oxo-, phenylmethyl ester|benzyl 2-oxochromene-3-carboxylate|Oprea1_411539|SCHEMBL3366496|DTXSID10340227|TWXSEJRQEDMZKQ-UHFFFAOYSA-N|BDBM50149607|CCG-18362|AKOS001288195|Coumarin-3-carboxylic acid, benzyl ester|Benzyl 2-oxo-2H-chromene-3-carboxylate #|EU-0008024|2-Oxo-2H-chromene-3-carboxylic acid benzyl ester|EN300-Show More⌵

Canonical SMILES:  O=C(OCc1ccccc1)c1cc2ccccc2oc1=O

Standard InChI:  InChI=1S/C17H12O4/c18-16(20-11-12-6-2-1-3-7-12)14-10-13-8-4-5-9-15(13)21-17(14)19/h1-10H,11H2

Standard InChI Key:  TWXSEJRQEDMZKQ-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA180436

   Benzyl 2-oxo-2H-chromene-3-carboxylate

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: 280.28

Molecular Weight (Monoisotopic): 280.0736

AlogP: 3.15

#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: 3.47

CX LogD: 3.47

Aromatic Rings: 3

Heavy Atoms: 21

QED Weighted: 0.55

Np Likeness Score: -0.42

References

1. Gobec S, Sova M, Kristan K, Rizner TL..  (2004)  Cinnamic acid esters as potent inhibitors of fungal 17beta-hydroxysteroid dehydrogenase--a model enzyme of the short-chain dehydrogenase/reductase superfamily.,  14  (15): [PMID:15225701] [10.1016/j.bmcl.2004.05.069]

2. Gleye C, Lewin G, Laurens A, Jullian JC, Loiseau P, Bories C, Hocquemiller R..  (2003)  Acaricidal activity of tonka bean extracts. Synthesis and structure-activity relationships of bioactive derivatives.,  66  (5): [PMID:12762809] [10.1021/np020563j]

Source

Source(1):

• Scientific Literature