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

ID: ALA288292

Chembl Id: CHEMBL288292

PubChem CID: 44286921

Max Phase: Preclinical

Molecular Formula: C26H32N2O11S

Molecular Weight: 580.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(COc2ccsc2C(=O)NCC2OC(CC(=O)N[C@@H](CCC(=O)O)C(=O)O)C(O)C(O)C2O)cc1

Standard InChI:  InChI=1S/C26H32N2O11S/c1-13-2-4-14(5-3-13)12-38-16-8-9-40-24(16)25(35)27-11-18-22(33)23(34)21(32)17(39-18)10-19(29)28-15(26(36)37)6-7-20(30)31/h2-5,8-9,15,17-18,21-23,32-34H,6-7,10-12H2,1H3,(H,27,35)(H,28,29)(H,30,31)(H,36,37)/t15-,17?,18?,21?,22?,23?/m0/s1

Standard InChI Key:  BXQMRHCOTFDNBB-PPBGLFSESA-N

Alternative Forms

1. Parent:

   

   ALA288292

   (2S)-2-[[2-[3,4,5-trihydroxy-6-[[[3-[(4-methylphenyl)methoxy]thiophene-2-carbonyl]amino]methyl]oxan-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: 580.61

Molecular Weight (Monoisotopic): 580.1727

AlogP: 0.04

#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: -0.12

CX LogD: -6.77

Aromatic Rings: 2

Heavy Atoms: 40

QED Weighted: 0.17

Np Likeness Score: -0.20

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