N-((2S,3R,4R,5S,6R)-2-((2R,3S,4R,5R,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-(4-methoxyphenoxy)tetrahydro-2H-pyran-3-yloxy)-5-(dihydroxyhydrosulfinyloxy)-6-((dihydroxyhydrosulfinyloxy)methyl)-4-hydroxytetrahydro-2H-pyran-3-yl)acetamide

ID: ALA4203669

Max Phase: Preclinical

Molecular Formula: C21H35NO18S2

Molecular Weight: 653.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(O[C@@H]2O[C@H](CO)[C@@H](O[C@@H]3O[C@H](CO[SH+]([O-])(O)O)[C@@H](O[SH+]([O-])(O)O)[C@H](O)[C@H]3NC(C)=O)[C@H](O)[C@H]2O)cc1

Standard InChI:  InChI=1S/C21H35NO18S2/c1-9(24)22-14-15(25)19(40-42(31,32)33)13(8-35-41(28,29)30)38-20(14)39-18-12(7-23)37-21(17(27)16(18)26)36-11-5-3-10(34-2)4-6-11/h3-6,12-21,23,25-29,31-32,41-42H,7-8H2,1-2H3,(H,22,24)/t12-,13-,14-,15-,16-,17-,18-,19-,20+,21-/m1/s1

Standard InChI Key:  INLCLOOYTMKMGS-SPBMPNPJSA-N

Molfile:  

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M  CHG  4  14   1  15  -1  16  -1  17   1
M  END

Alternative Forms

1. Parent:

   

   ALA4203669

   ---

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: 653.63

Molecular Weight (Monoisotopic): 653.1296

AlogP: -3.35

#Rotatable Bonds: 12

Polar Surface Area: 301.67

Molecular Species: NEUTRAL

HBA: 18

HBD: 9

#RO5 Violations: 3

HBA (Lipinski): 19

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 11.59

CX Basic pKa: ┄

CX LogP: -3.04

CX LogD: -3.04

Aromatic Rings: 1

Heavy Atoms: 42

QED Weighted: 0.08

Np Likeness Score: 0.96

References

1. Maza S, Gandia-Aguado N, de Paz JL, Nieto PM..  (2018)  Fluorous-tag assisted synthesis of a glycosaminoglycan mimetic tetrasaccharide as a high-affinity FGF-2 and midkine ligand.,  26  (5): [PMID:29409708] [10.1016/j.bmc.2018.01.022]

Source

Source(1):

• Scientific Literature