2-[2-(6-{[2-(2,4-Dichloro-phenylcarbamoyl)-acetylamino]-methyl}-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid

ID: ALA287905

Chembl Id: CHEMBL287905

PubChem CID: 44287048

Max Phase: Preclinical

Molecular Formula: C22H27Cl2N3O11

Molecular Weight: 580.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)CC[C@H](NC(=O)CC1OC(CNC(=O)CC(=O)Nc2ccc(Cl)cc2Cl)C(O)C(O)C1O)C(=O)O

Standard InChI:  InChI=1S/C22H27Cl2N3O11/c23-9-1-2-11(10(24)5-9)26-17(30)7-15(28)25-8-14-20(34)21(35)19(33)13(38-14)6-16(29)27-12(22(36)37)3-4-18(31)32/h1-2,5,12-14,19-21,33-35H,3-4,6-8H2,(H,25,28)(H,26,30)(H,27,29)(H,31,32)(H,36,37)/t12-,13?,14?,19?,20?,21?/m0/s1

Standard InChI Key:  BNWQSYBQTUGVDR-GPHMBJDESA-N

Alternative Forms

1. Parent:

   

   ALA287905

   (2S)-2-[[2-[6-[[[3-(2,4-dichloroanilino)-3-oxopropanoyl]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: 580.37

Molecular Weight (Monoisotopic): 579.1023

AlogP: -0.89

#Rotatable Bonds: 12

Polar Surface Area: 231.82

Molecular Species: ACID

HBA: 9

HBD: 8

#RO5 Violations: 2

HBA (Lipinski): 14

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 3.24

CX Basic pKa: ┄

CX LogP: -1.44

CX LogD: -8.08

Aromatic Rings: 1

Heavy Atoms: 38

QED Weighted: 0.14

Np Likeness Score: -0.23

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