(1S,2S,4S,5S)-4-(((2S,3S,4R,5S,6R)-3-(4-(aminomethyl)-1H-1,2,3-triazol-1-yl)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-(2-chloroethoxy)-N1,N2-bis(4-(hydroxymethyl)benzyl)cyclohexane-1,2-dicarboxamide

ID: ALA5283713

Max Phase: Preclinical

Molecular Formula: C35H47ClN6O10

Molecular Weight: 747.25

Names and Identifiers

Canonical SMILES:  NCc1cn([C@@H]2[C@@H](O[C@H]3C[C@H](C(=O)NCc4ccc(CO)cc4)[C@@H](C(=O)NCc4ccc(CO)cc4)C[C@@H]3OCCCl)O[C@H](CO)[C@@H](O)[C@@H]2O)nn1

Standard InChI:  InChI=1S/C35H47ClN6O10/c36-9-10-50-27-11-25(33(48)38-14-20-1-5-22(17-43)6-2-20)26(34(49)39-15-21-3-7-23(18-44)8-4-21)12-28(27)51-35-30(42-16-24(13-37)40-41-42)32(47)31(46)29(19-45)52-35/h1-8,16,25-32,35,43-47H,9-15,17-19,37H2,(H,38,48)(H,39,49)/t25-,26-,27-,28-,29+,30-,31+,32+,35-/m0/s1

Standard InChI Key:  BYGZQFCUFRSCML-RWSQSUCKSA-N

Molfile:  

 
     RDKit          2D

 53 57  0  0  0  0  0  0  0  0999 V2000
   -2.4989   -1.8355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7844   -1.4230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0699   -1.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0699   -2.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7844   -3.0732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3552   -3.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3552   -3.8983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3593   -2.6608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739   -3.0732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8271   -2.7378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3790   -3.3507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9666   -4.0648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1600   -3.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3792   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2042   -4.7792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3593   -1.8355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739   -1.4230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739   -0.5980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594   -0.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3594    0.6394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521    1.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3521    1.8819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0694    0.6494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7810    1.0669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984    0.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2130    1.0786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9317    0.6672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9317   -0.1535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6461   -0.5661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6461   -1.3911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2199   -0.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4984   -0.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739    1.0519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739    1.8720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8001    2.2795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711    2.2895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711    3.1145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346    3.5320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3346    4.3605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0424    4.7736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7554    4.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4699    4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1843    4.3667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7554    3.5415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0521    3.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7883    0.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7883   -0.1854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4946   -0.6131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2174   -0.2157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9232   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6461   -0.2456    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3552   -1.4228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3593   -1.0104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  1
  3  4  1  0
  4  5  1  6
  4  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  1
 10  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13  9  1  0
 12 14  1  0
 14 15  1  0
  8 16  1  0
 16 17  1  0
 18 17  1  1
 19 18  1  0
 20 19  1  0
 20 21  1  6
 21 22  2  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  2  0
 31 32  1  0
 32 25  2  0
 33 20  1  0
 33 34  1  1
 34 35  2  0
 34 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  1  0
 42 43  1  0
 41 44  2  0
 44 45  1  0
 45 38  2  0
 33 46  1  0
 47 46  1  0
 18 47  1  0
 47 48  1  6
 48 49  1  0
 49 50  1  0
 50 51  1  0
 16 52  1  0
  3 52  1  0
 16 53  1  1
M  END

Alternative Forms

1. Parent:

   

   ALA5283713

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 747.25

Molecular Weight (Monoisotopic): 746.3042

AlogP: -0.63

#Rotatable Bonds: 16

Polar Surface Area: 243.77

Molecular Species: NEUTRAL

HBA: 14

HBD: 8

#RO5 Violations: 3

HBA (Lipinski): 16

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 12.82

CX Basic pKa: 7.99

CX LogP: -1.32

CX LogD: -2.01

Aromatic Rings: 3

Heavy Atoms: 52

QED Weighted: 0.09

Np Likeness Score: 0.15

References

1. 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