[2'-(3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-biphenyl-3-yl]-acetic acid

ID: ALA2303887

Chembl Id: CHEMBL2303887

PubChem CID: 71717843

Max Phase: Preclinical

Molecular Formula: C20H22O8

Molecular Weight: 390.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)Cc1cccc(-c2ccccc2O[C@H]2O[C@H](CO)[C@@H](O)[C@@H](O)[C@@H]2O)c1

Standard InChI:  InChI=1S/C20H22O8/c21-10-15-17(24)18(25)19(26)20(28-15)27-14-7-2-1-6-13(14)12-5-3-4-11(8-12)9-16(22)23/h1-8,15,17-21,24-26H,9-10H2,(H,22,23)/t15-,17-,18-,19+,20+/m1/s1

Standard InChI Key:  NCYFXLIEKHHURF-XLSIIYIISA-N

Alternative Forms

1. Parent:

   

   ALA2303887

   2-[3-[2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]phenyl]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: 390.39

Molecular Weight (Monoisotopic): 390.1315

AlogP: 0.16

#Rotatable Bonds: 6

Polar Surface Area: 136.68

Molecular Species: ACID

HBA: 7

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.18

CX Basic pKa: ┄

CX LogP: 0.69

CX LogD: -2.36

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.47

Np Likeness Score: 1.16

References

1. Kogan TP, Dupré B, Bui H, McAbee KL, Kassir JM, Scott IL, Hu X, Vanderslice P, Beck PJ, Dixon RA..  (1998)  Novel synthetic inhibitors of selectin-mediated cell adhesion: synthesis of 1,6-bis[3-(3-carboxymethylphenyl)-4-(2-alpha-D- mannopyranosyloxy)phenyl]hexane (TBC1269).,  41  (7): [PMID:9544210] [10.1021/jm9704917]

2. Kogan TP, Dupré B, Keller KM, Scott IL, Bui H, Market RV, Beck PJ, Voytus JA, Revelle BM, Scott D..  (1995)  Rational design and synthesis of small molecule, non-oligosaccharide selectin inhibitors: (alpha-D-mannopyranosyloxy)biphenyl-substituted carboxylic acids.,  38  (26): [PMID:8544173] [10.1021/jm00026a004]

Source

Source(1):

• Scientific Literature