ID: ALA32476

Max Phase: Preclinical

Molecular Formula: C25H27ClO8

Molecular Weight: 490.94

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(/C=C/c1ccc(O)cc1)O[C@@H]1C[C@](OCCCc2ccc(Cl)cc2)(C(=O)O)C[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C25H27ClO8/c26-18-8-3-16(4-9-18)2-1-13-33-25(24(31)32)14-20(28)23(30)21(15-25)34-22(29)12-7-17-5-10-19(27)11-6-17/h3-12,20-21,23,27-28,30H,1-2,13-15H2,(H,31,32)/b12-7+/t20-,21-,23-,25+/m1/s1

Standard InChI Key:  FSOUCNYWDDFYIO-XJRBSVQTSA-N

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

Properties

Molecular Weight: 490.94

Molecular Weight (Monoisotopic): 490.1394

AlogP: 2.96

#Rotatable Bonds: 9

Polar Surface Area: 133.52

Molecular Species: ACID

HBA: 7

HBD: 4

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 3.57

CX Basic pKa:

CX LogP: 3.74

CX LogD: 0.38

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.24

Np Likeness Score: 1.35

References

1. Hemmerle H, Burger HJ, Below P, Schubert G, Rippel R, Schindler PW, Paulus E, Herling AW..  (1997)  Chlorogenic acid and synthetic chlorogenic acid derivatives: novel inhibitors of hepatic glucose-6-phosphate translocase.,  40  (2): [PMID:9003513] [10.1021/jm9607360]

2. Charkoudian LK, Farrell BP, Khosla C.  (2012)  Natural product inhibitors of glucose-6-phosphate translocase,  3  (8): [10.1039/C2MD20008B]

Source

Source(1):

• Scientific Literature