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

ID: ALA3215410

Chembl Id: CHEMBL3215410

PubChem CID: 90664153

Max Phase: Preclinical

Molecular Formula: C24H27NO11

Molecular Weight: 505.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC[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/C24H27NO11/c26-11-17-19(29)20(30)21(31)24(36-17)35-16-7-2-1-6-14(16)12-4-3-5-13(10-12)22(32)25-15(23(33)34)8-9-18(27)28/h1-7,10,15,17,19-21,24,26,29-31H,8-9,11H2,(H,25,32)(H,27,28)(H,33,34)/t15-,17+,19+,20+,21-,24-/m0/s1

Standard InChI Key:  NTAZZCPXYKAGOK-XVPBJKLYSA-N

Alternative Forms

1. Parent:

   

   ALA3215410

   (2S)-2-[[3-[2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]benzoyl]amino]pentanedioic 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: 505.48

Molecular Weight (Monoisotopic): 505.1584

AlogP: -0.42

#Rotatable Bonds: 10

Polar Surface Area: 203.08

Molecular Species: ACID

HBA: 9

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 12

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.32

CX Basic pKa: ┄

CX LogP: -0.18

CX LogD: -6.67

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.22

Np Likeness Score: 0.84

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