2-{2-[6-({[3-(4-tert-Butyl-benzyloxy)-thiophene-2-carbonyl]-amino}-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-yl]-acetylamino}-pentanedioic acid

ID: ALA432294

Chembl Id: CHEMBL432294

PubChem CID: 44287085

Max Phase: Preclinical

Molecular Formula: C29H38N2O11S

Molecular Weight: 622.69

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)c1ccc(COc2ccsc2C(=O)NCC2OC(CC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(O)C(O)C2O)cc1

Standard InChI:  InChI=1S/C29H38N2O11S/c1-29(2,3)16-6-4-15(5-7-16)14-41-18-10-11-43-26(18)27(38)30-13-20-24(36)25(37)23(35)19(42-20)12-21(32)31-17(28(39)40)8-9-22(33)34/h4-7,10-11,17,19-20,23-25,35-37H,8-9,12-14H2,1-3H3,(H,30,38)(H,31,32)(H,33,34)(H,39,40)/t17-,19?,20?,23?,24?,25?/m0/s1

Standard InChI Key:  XPCFJSIVNSEEFP-XEQZSQIOSA-N

Alternative Forms

1. Parent:

   

   ALA432294

   (2S)-2-[[2-[6-[[[3-[(4-tert-butylphenyl)methoxy]thiophene-2-carbonyl]amino]methyl]-3,4,5-trihydroxyoxan-2-yl]acetyl]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: 622.69

Molecular Weight (Monoisotopic): 622.2196

AlogP: 1.03

#Rotatable Bonds: 13

Polar Surface Area: 211.95

Molecular Species: ACID

HBA: 10

HBD: 7

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.24

CX Basic pKa: ┄

CX LogP: 0.91

CX LogD: -5.73

Aromatic Rings: 2

Heavy Atoms: 43

QED Weighted: 0.17

Np Likeness Score: -0.27

References

1. Kaila N, Chen L, Thomas BE, Tsao D, Tam S, Bedard PW, Camphausen RT, Alvarez JC, Ullas G..  (2002)  Beta-C-mannosides as selectin inhibitors.,  45  (8): [PMID:11931610] [10.1021/jm010390f]

Source

Source(1):

• Scientific Literature