Sodium sulfated glycoconjugate derivative

ID: ALA3215305

PubChem CID: 90664017

Max Phase: Preclinical

Molecular Formula: C24H33N2Na3O17S3

Molecular Weight: 720.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1O[C@@H](COCC(=O)N(CC(=O)NC2CCCCC2)Cc2ccccc2)[C@@H](OS(=O)(=O)[O-])[C@H](OS(=O)(=O)[O-])[C@H]1OS(=O)(=O)[O-].[Na+].[Na+].[Na+]

Standard InChI:  InChI=1S/C24H36N2O17S3.3Na/c1-38-24-23(43-46(35,36)37)22(42-45(32,33)34)21(41-44(29,30)31)18(40-24)14-39-15-20(28)26(12-16-8-4-2-5-9-16)13-19(27)25-17-10-6-3-7-11-17;;;/h2,4-5,8-9,17-18,21-24H,3,6-7,10-15H2,1H3,(H,25,27)(H,29,30,31)(H,32,33,34)(H,35,36,37);;;/q;3*+1/p-3/t18-,21+,22-,23+,24-;;;/m0.../s1

Standard InChI Key:  SKDPYSQRDVPMEZ-ANYPKSLTSA-K

Molfile:  

     RDKit          2D

 49 48  0  0  0  0  0  0  0  0999 V2000
    1.0018   -4.6899    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
   -2.1589    1.0851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734    0.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445    0.6726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734    2.3226    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3024    0.6726    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7300    1.9101    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8734   -0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1589   -0.5649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445   -0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1589    1.9101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879    1.0851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7300    1.0851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -0.5649    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5568   -0.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134   -0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879    2.7351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7300    2.7351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0168    0.2601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8424   -0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4609    3.0370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0950    1.9101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    1.6081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5550    1.9101    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8899   -0.0419    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7149    1.3870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2713   -0.1524    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1279   -1.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134    0.6726    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5568   -1.3899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879   -0.5649    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0155   -0.1524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7300   -0.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134   -1.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989   -0.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9858   -0.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5879   -1.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989   -1.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4134   -2.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9858   -1.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7002   -0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989   -3.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0155   -1.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4147   -0.5649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7002   -1.8024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4147   -1.3899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0155   -2.6274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6540    0.0000    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    0.0000   -4.6899    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  3  2  1  0
  4  2  1  0
  5 11  1  0
  6 12  1  0
  7 13  1  0
  8  3  1  0
  9 10  1  0
 10  4  1  0
  2 11  1  1
  3 12  1  6
  4 13  1  6
 14 16  1  0
 15 20  1  0
 16 35  1  0
 17  5  1  0
 18  7  1  0
 19  6  1  0
 20 14  1  0
 21  5  2  0
 22  7  2  0
 23  5  2  0
 24  7  2  0
 25  6  2  0
 26  6  2  0
 27 15  1  0
 28 14  1  0
 29 16  2  0
 30 15  2  0
  8 31  1  6
 32 33  1  0
 10 33  1  6
 34 28  1  0
 35 32  1  0
 36 27  1  0
 37 31  1  0
 38 34  1  0
 39 34  2  0
 40 36  1  0
 41 36  1  0
 42 39  1  0
 43 38  2  0
 44 41  1  0
 45 40  1  0
 46 45  1  0
 47 43  1  0
  9  8  1  0
 42 47  2  0
 44 46  1  0
M  CHG  6   1   1  17  -1  18  -1  19  -1  48   1  49   1
M  END

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: 720.75

Molecular Weight (Monoisotopic): 720.1176

AlogP: -0.58

#Rotatable Bonds: 16

Polar Surface Area: 267.90

Molecular Species: ACID

HBA: 14

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 19

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -2.78

CX Basic pKa: ┄

CX LogP: -5.98

CX LogD: -7.07

Aromatic Rings: 1

Heavy Atoms: 46

QED Weighted: 0.16

Np Likeness Score: -0.15

References

1. Liu L, Ping Li C, Cochran S, Ferro V..  (2004)  Application of the four-component Ugi condensation for the preparation of sulfated glycoconjugate libraries.,  14  (9): [PMID:15081013] [10.1016/j.bmcl.2004.02.017]

Source

Source(1):

• Scientific Literature