(5-{2-[4-(2,3,4-trihydroxy-phenyl)-butyrylamino]-phenyl}-thiophen-2-yl)-acetic acid

ID: ALA221041

Chembl Id: CHEMBL221041

PubChem CID: 16116555

Max Phase: Preclinical

Molecular Formula: C22H21NO6S

Molecular Weight: 427.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1ccc(-c2ccccc2NC(=O)CCCc2ccc(O)c(O)c2O)s1

Standard InChI:  InChI=1S/C22H21NO6S/c24-17-10-8-13(21(28)22(17)29)4-3-7-19(25)23-16-6-2-1-5-15(16)18-11-9-14(30-18)12-20(26)27/h1-2,5-6,8-11,24,28-29H,3-4,7,12H2,(H,23,25)(H,26,27)

Standard InChI Key:  IFMDHVNLKUVJIU-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA221041

   (5-{2-[4-(2,3,4-Trihydroxy-phenyl)-butyrylamino]-phenyl}-thiophen-2-yl)-acetic 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: 427.48

Molecular Weight (Monoisotopic): 427.1090

AlogP: 4.12

#Rotatable Bonds: 8

Polar Surface Area: 127.09

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.63

CX Basic pKa:

CX LogP: 4.22

CX LogD: 1.50

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.34

Np Likeness Score: -0.37

References

1. Kranich R, Busemann AS, Bock D, Schroeter-Maas S, Beyer D, Heinemann B, Meyer M, Schierhorn K, Zahlten R, Wolff G, Aydt EM..  (2007)  Rational design of novel, potent small molecule pan-selectin antagonists.,  50  (6): [PMID:17302397] [10.1021/jm060536g]

Source

Source(1):

• Scientific Literature