(R)-2-{[2'-(3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-biphenyl-3-carbonyl]-amino}-succinic acid

ID: ALA3215416

Chembl Id: CHEMBL3215416

PubChem CID: 90664159

Max Phase: Preclinical

Molecular Formula: C23H25NO11

Molecular Weight: 491.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)C[C@@H](NC(=O)c1cccc(-c2ccccc2O[C@H]2O[C@H](CO)[C@@H](O)[C@@H](O)[C@@H]2O)c1)C(=O)O

Standard InChI:  InChI=1S/C23H25NO11/c25-10-16-18(28)19(29)20(30)23(35-16)34-15-7-2-1-6-13(15)11-4-3-5-12(8-11)21(31)24-14(22(32)33)9-17(26)27/h1-8,14,16,18-20,23,25,28-30H,9-10H2,(H,24,31)(H,26,27)(H,32,33)/t14-,16-,18-,19-,20+,23+/m1/s1

Standard InChI Key:  MRVMNIAEVMQYAZ-AFSWSCEWSA-N

Alternative Forms

1. Parent:

   

   ALA3215416

   (2R)-2-[[3-[2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]benzoyl]amino]butanedioic 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: 491.45

Molecular Weight (Monoisotopic): 491.1428

AlogP: -0.81

#Rotatable Bonds: 9

Polar Surface Area: 203.08

Molecular Species: ACID

HBA: 9

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.34

CX Basic pKa: ┄

CX LogP: -0.47

CX LogD: -6.03

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.23

Np Likeness Score: 0.80

References

1. 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