3,5-dihydroxy-N-((1R,2S)-2-(((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)carbamoyl)cyclohexyl)benzamide

ID: ALA5276974

Max Phase: Preclinical

Molecular Formula: C20H28N2O8

Molecular Weight: 424.45

Names and Identifiers

Canonical SMILES:  C[C@@H]1O[C@@H](NC(=O)[C@H]2CCCC[C@H]2NC(=O)c2cc(O)cc(O)c2)[C@@H](O)[C@H](O)[C@@H]1O

Standard InChI:  InChI=1S/C20H28N2O8/c1-9-15(25)16(26)17(27)20(30-9)22-19(29)13-4-2-3-5-14(13)21-18(28)10-6-11(23)8-12(24)7-10/h6-9,13-17,20,23-27H,2-5H2,1H3,(H,21,28)(H,22,29)/t9-,13-,14+,15+,16+,17-,20+/m0/s1

Standard InChI Key:  IXPHUTJDXVFANJ-HFEOQFHKSA-N

Molfile:  

 
     RDKit          2D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.5722   -2.6810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -2.2686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290   -1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8578   -1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.2062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7146    2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    2.6810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.2684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0001    0.2062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7141    1.4435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7141   -0.2065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   -0.2066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433   -1.0316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.2059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722   -0.2065    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.0310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5722    1.4435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1433    1.4437    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.6810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  2  0
  5  4  1  0
  6  5  2  0
  2  7  2  0
  7  6  1  0
  6  8  1  0
  8  9  2  0
 10  8  1  0
 11 10  1  1
 12 11  1  0
 13 12  1  0
 14 13  1  0
 15 14  1  0
 11 16  1  0
 16 15  1  0
 12 17  1  1
 17 18  2  0
 19 17  1  0
 20 19  1  1
 21 20  1  0
 21 22  1  1
 23 21  1  0
 23 24  1  6
 25 23  1  0
 25 26  1  6
 27 25  1  0
 27 28  1  6
 20 29  1  0
 27 29  1  0
  4 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5276974

   ---

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: 424.45

Molecular Weight (Monoisotopic): 424.1846

AlogP: -0.67

#Rotatable Bonds: 4

Polar Surface Area: 168.58

Molecular Species: NEUTRAL

HBA: 8

HBD: 7

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.56

CX Basic pKa: ┄

CX LogP: -0.33

CX LogD: -0.36

Aromatic Rings: 1

Heavy Atoms: 30

QED Weighted: 0.33

Np Likeness Score: 0.53

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