(R)-6-[(S)-2-hydroxy-4-(4-hydroxyphenyl)butyl]-5,6-dihydropyran-2-one

ID: ALA250638

Chembl Id: CHEMBL250638

PubChem CID: 24762836

Max Phase: Preclinical

Molecular Formula: C15H18O4

Molecular Weight: 262.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=CC[C@H](C[C@@H](O)CCc2ccc(O)cc2)O1

Standard InChI:  InChI=1S/C15H18O4/c16-12-7-4-11(5-8-12)6-9-13(17)10-14-2-1-3-15(18)19-14/h1,3-5,7-8,13-14,16-17H,2,6,9-10H2/t13-,14+/m0/s1

Standard InChI Key:  ILSJICRXKSNXIV-UONOGXRCSA-N

Alternative Forms

1. Parent:

   

   ALA250638

   Dodoneine

Molecule Features

Natural Product: Yes

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: 262.30

Molecular Weight (Monoisotopic): 262.1205

AlogP: 1.95

#Rotatable Bonds: 5

Polar Surface Area: 66.76

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.30

CX Basic pKa: ┄

CX LogP: 2.47

CX LogD: 2.47

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.80

Np Likeness Score: 2.36

References

1. Ouedraogo M, Carreyre H, Vandebrouck C, Bescond J, Raymond G, Guissou IP, Cognard C, Becq F, Potreau D, Cousson A, Marrot J, Coustard JM..  (2007)  Structure elucidation of a dihydropyranone from Tapinanthus dodoneifolius.,  70  (12): [PMID:18052322] [10.1021/np070355x]

2. Carreyre H, Coustard JM, Carré G, Vandebrouck C, Bescond J, Ouédraogo M, Marrot J, Vullo D, Supuran CT, Thibaudeau S..  (2013)  Natural product hybrid and its superacid synthesized analogues: dodoneine and its derivatives show selective inhibition of carbonic anhydrase isoforms I, III, XIII and XIV.,  21  (13): [PMID:23685174] [10.1016/j.bmc.2013.04.041]

3. IC50 data for the L-type calcium channel extracted from a set of literature articles, 

Source

Source(1):

• Scientific Literature