sodium(2R,3R,4S,5S,6S)-2-((2-(N-ethyl-3-phenylpropanamido)acetamido)methyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triyl trisulfate

ID: ALA2087902

PubChem CID: 70682741

Max Phase: Preclinical

Molecular Formula: C20H27N2Na3O16S3

Molecular Weight: 650.66

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC(=O)NC[C@H]1O[C@H](OC)[C@@H](OS(=O)(=O)[O-])[C@@H](OS(=O)(=O)[O-])[C@@H]1OS(=O)(=O)[O-])C(=O)CCc1ccccc1.[Na+].[Na+].[Na+]

Standard InChI:  InChI=1S/C20H30N2O16S3.3Na/c1-3-22(16(24)10-9-13-7-5-4-6-8-13)12-15(23)21-11-14-17(36-39(25,26)27)18(37-40(28,29)30)19(20(34-2)35-14)38-41(31,32)33;;;/h4-8,14,17-20H,3,9-12H2,1-2H3,(H,21,23)(H,25,26,27)(H,28,29,30)(H,31,32,33);;;/q;3*+1/p-3/t14-,17-,18+,19+,20+;;;/m1.../s1

Standard InChI Key:  VOTNKSQNKDXCSJ-CZLVMEPXSA-K

Molfile:  

     RDKit          2D

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   -0.5041   -1.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2079   -2.0084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2198   -0.3646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8125   -3.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4947    0.4497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2043   -1.6126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2098    0.8611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.9151   -2.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1977   -3.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1949   -4.0816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9087   -4.4970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6268   -4.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6260   -3.2593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4708    1.0042    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  5 13  1  6
 22 24  2  0
  6  7  1  0
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  9 14  1  0
 10 26  1  0
  7  8  1  0
 26 27  1  0
 13 15  1  0
 26 28  2  0
 26 29  2  0
 14 16  1  0
  7  9  1  1
 11 30  1  0
 16 17  1  0
 30 31  1  0
  3  4  1  0
 30 32  2  0
 16 18  2  0
 30 33  2  0
  3 10  1  1
 17 19  1  0
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  3  8  1  0
 20 35  1  0
 19 20  1  0
 34 36  1  0
  4 11  1  1
 35 37  1  0
 20 21  2  0
 37 38  1  0
  4  5  1  0
 38 39  2  0
 12 22  1  0
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  8 12  1  6
 40 41  2  0
 22 23  1  0
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  5  6  1  0
 42 43  2  0
 43 38  1  0
M  CHG  6   1   1   2   1  23  -1  27  -1  31  -1  44   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: 650.66

Molecular Weight (Monoisotopic): 650.0757

AlogP: -1.48

#Rotatable Bonds: 15

Polar Surface Area: 258.67

Molecular Species: ACID

HBA: 13

HBD: 4

#RO5 Violations: 2

HBA (Lipinski): 18

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -2.78

CX Basic pKa: ┄

CX LogP: -6.65

CX LogD: -7.79

Aromatic Rings: 1

Heavy Atoms: 41

QED Weighted: 0.16

Np Likeness Score: -0.01

References

1. Liu L, Li C, Cochran S, Feder D, Guddat LW, Ferro V..  (2012)  A focused sulfated glycoconjugate Ugi library for probing heparan sulfate-binding angiogenic growth factors.,  22  (19): [PMID:22929233] [10.1016/j.bmcl.2012.08.001]

Source

Source(1):

• Scientific Literature