ID: ALA2029056

Max Phase: Preclinical

Molecular Formula: C48H91NaO18S

Molecular Weight: 989.31

Molecule Type: Small molecule

Representations

Synonyms (1): 3'-O-Sulfated Sialyl Lewis X
Synonyms from Alternative Forms(1):

Canonical SMILES:  CCCCCCCCCCCCCCC(CCCCCCCCCCCCCC)CO[C@@H]1O[C@H](CO)[C@@H](O[C@@H]2O[C@H](CO)[C@H](O)[C@H](OS(=O)(=O)[O-])[C@H]2O)[C@H](O[C@@H]2O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]2O)[C@H]1O.[Na+]

Standard InChI:  InChI=1S/C48H92O18S.Na/c1-4-6-8-10-12-14-16-18-20-22-24-26-28-34(29-27-25-23-21-19-17-15-13-11-9-7-5-2)32-60-46-42(56)45(65-47-40(54)39(53)37(51)33(3)61-47)43(36(31-50)63-46)64-48-41(55)44(66-67(57,58)59)38(52)35(30-49)62-48;/h33-56H,4-32H2,1-3H3,(H,57,58,59);/q;+1/p-1/t33-,35+,36+,37+,38-,39+,40-,41+,42+,43+,44-,45+,46+,47-,48-;/m0./s1

Standard InChI Key:  YFBASYVPHDAEPI-NACWSHMVSA-M

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

Properties

Molecular Weight: 989.31

Molecular Weight (Monoisotopic): 988.6004

AlogP: 5.10

#Rotatable Bonds: 37

Polar Surface Area: 280.82

Molecular Species: ACID

HBA: 17

HBD: 9

#RO5 Violations: 4

HBA (Lipinski): 18

HBD (Lipinski): 9

#RO5 Violations (Lipinski): 4

CX Acidic pKa: -1.98

CX Basic pKa:

CX LogP: 6.23

CX LogD: 5.70

Aromatic Rings: 0

Heavy Atoms: 67

QED Weighted: 0.03

Np Likeness Score: 1.19

References

1. Hiramatsu Y, Tsukida T, Nakai Y, Inoue Y, Kondo H..  (2000)  Study on selectin blocker. 8. Lead discovery of a non-sugar antagonist using a 3D-pharmacophore model.,  43  (8): [PMID:10780903] [10.1021/jm990342j]

2. Hiramatsu Y, Moriyama H, Kiyoi T, Tsukida T, Inoue Y, Kondo H..  (1998)  Studies on selectin blockers. 6. Discovery of homologous fucose sugar unit necessary for E-selectin binding.,  41  (13): [PMID:9632363] [10.1021/jm9707481]

3. Tsukida T, Hiramatsu Y, Tsujishita H, Kiyoi T, Yoshida M, Kurokawa K, Moriyama H, Ohmoto H, Wada Y, Saito T, Kondo H..  (1997)  Studies on selection blockers. 5. Design, synthesis, and biological profile of sialyl Lewis x mimetics based on modified serine-glutamic acid dipeptides.,  40  (22): [PMID:9357520] [10.1021/jm970262k]

4. Tsujishita H, Hiramatsu Y, Kondo N, Ohmoto H, Kondo H, Kiso M, Hasegawa A..  (1997)  Selectin-ligand interactions revealed by molecular dynamics simulation in solution.,  40  (3): [PMID:9022803] [10.1021/jm9606103]

5. Tsukida T, Moriyama H, Kurokawa K, Achiha T, Inoue Y, Kondo H..  (1998)  Studies on selectin blockers. 7. Structure-activity relationships of sialyl Lewis X mimetics based on modified Ser-Glu dipeptides.,  41  (22): [PMID:9784103] [10.1021/jm980267x]

6. Govindarajan M..  (2018)  Amphiphilic glycoconjugates as potential anti-cancer chemotherapeutics.,  143  [PMID:29126728] [10.1016/j.ejmech.2017.10.015]

Source

Source(1):

• Scientific Literature