(1S,2S,4S,5S)-4-(2-azidoethoxy)-N1,N2-bis(4-(hydroxymethyl)benzyl)-5-((2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)cyclohexane-1,2-dicarboxamide

ID: ALA3121700

Chembl Id: CHEMBL3121700

PubChem CID: 71623467

Max Phase: Preclinical

Molecular Formula: C32H43N5O11

Molecular Weight: 673.72

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  [N-]=[N+]=NCCO[C@H]1C[C@H](C(=O)NCc2ccc(CO)cc2)[C@@H](C(=O)NCc2ccc(CO)cc2)C[C@@H]1O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C32H43N5O11/c33-37-36-9-10-46-24-11-22(30(44)34-13-18-1-5-20(15-38)6-2-18)23(31(45)35-14-19-3-7-21(16-39)8-4-19)12-25(24)47-32-29(43)28(42)27(41)26(17-40)48-32/h1-8,22-29,32,38-43H,9-17H2,(H,34,44)(H,35,45)/t22-,23-,24-,25-,26+,27+,28-,29-,32-/m0/s1

Standard InChI Key:  AOBVPDDHLOAJGJ-JYVQCWHTSA-N

Alternative Forms

1. Parent:

   

   ALA3121700

   (1S,2S,4S,5S)-4-(2-azidoethoxy)-1-N,2-N-bis[[4-(hydroxymethyl)phenyl]methyl]-5-[(2S,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycyclohexane-1,2-dicarboxamide

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: 673.72

Molecular Weight (Monoisotopic): 673.2959

AlogP: -0.49

#Rotatable Bonds: 15

Polar Surface Area: 256.03

Molecular Species: ACID

HBA: 12

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 8

#RO5 Violations (Lipinski): 3

CX Acidic pKa: -10.21

CX Basic pKa: ┄

CX LogP: -1.60

CX LogD: -1.71

Aromatic Rings: 2

Heavy Atoms: 48

QED Weighted: 0.05

Np Likeness Score: 0.68

References

1. Tomašić T, Hajšek D, Švajger U, Luzar J, Obermajer N, Petit-Haertlein I, Fieschi F, Anderluh M..  (2014)  Monovalent mannose-based DC-SIGN antagonists: targeting the hydrophobic groove of the receptor.,  75  [PMID:24556146] [10.1016/j.ejmech.2014.01.047]

2. Cramer J..  (2021)  Medicinal chemistry of the myeloid C-type lectin receptors Mincle, Langerin, and DC-SIGN.,  12  (12.0): [PMID:35024612] [10.1039/D1MD00238D]

Source

Source(1):

• Scientific Literature