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Chemistry

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Also known as: 258818-34-7, 258818-34-7 (free base), At-2347, 2-[[(2s)-1-[(2s)-5-amino-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]acetic acid, Glycylglycyl-l-valyl-l-leucyl-l-valyl-l-glutaminyl-l-prolylglycine, Larazotide [usan:inn]

Molecular Formula

C₃₂H₅₅N₉O₁₀

Molecular Weight

725.8 g/mol

InChI Key

ORFLZNAGUTZRLQ-ZMBVWFSWSA-N

An octapeptide inhibitor of paracellular permeability whose structure is derived from a protein (zonula occludens toxin) secreted by Vibrio cholerae for treatment of Coeliac disease.

1 2D Structure

Larazotide Acetate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[[(2S)-1-[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]acetic acid

2.1.2 InChI

InChI=1S/C32H55N9O10/c1-16(2)12-20(38-30(49)26(17(3)4)39-24(44)14-35-23(43)13-33)28(47)40-27(18(5)6)31(50)37-19(9-10-22(34)42)32(51)41-11-7-8-21(41)29(48)36-15-25(45)46/h16-21,26-27H,7-15,33H2,1-6H3,(H2,34,42)(H,35,43)(H,36,48)(H,37,50)(H,38,49)(H,39,44)(H,40,47)(H,45,46)/t19-,20-,21-,26-,27-/m0/s1

2.1.3 InChI Key

ORFLZNAGUTZRLQ-ZMBVWFSWSA-N

2.1.4 Canonical SMILES

CC(C)CC(C(=O)NC(C(C)C)C(=O)NC(CCC(=O)N)C(=O)N1CCCC1C(=O)NCC(=O)O)NC(=O)C(C(C)C)NC(=O)CNC(=O)CN

2.1.5 Isomeric SMILES

CC(C)C[C@@H](C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCC(=O)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)CN

2.2 Synonyms

2.2.1 Depositor-Supplied Synonyms

1. 258818-34-7

2. 258818-34-7 (free Base)

3. At-2347

4. 2-[[(2s)-1-[(2s)-5-amino-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[2-[(2-aminoacetyl)amino]acetyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-3-methylbutanoyl]amino]-5-oxopentanoyl]pyrrolidine-2-carbonyl]amino]acetic Acid

5. Glycylglycyl-l-valyl-l-leucyl-l-valyl-l-glutaminyl-l-prolylglycine

6. Larazotide [usan:inn]

7. Unii-zn3r5560zv

8. Larazotide-acetate

9. At 2347

10. Larazotide (usan/inn)

11. Zn3r5560zv

12. Chembl2105646

13. Dtxsid30180526

14. Chebi:177799

15. Zinc68009799

16. Db05645

17. H-gly-gly-val-leu-val-gln-pro-gly-oh

18. Hy-106268

19. Cs-0025478

20. D09351

21. 818l347

22. Q27295752

2.3 Create Date

2006-10-25

3 Chemical and Physical Properties

Molecular Formula	C₃₂H₅₅N₉O₁₀
Molecular Weight	725.8 g/mol
XLogP3	-3.6
Hydrogen Bond Donor Count	9
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	21
Exact Mass	725.40718899 g/mol
Monoisotopic Mass	725.40718899 g/mol
Topological Polar Surface Area	301 Å²
Heavy Atom Count	51
Formal Charge	0
Complexity	1290
Isotope Atom Count	0
Defined Atom Stereocenter Count	5
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in autoimmune diseases, diabetes mellitus type 1, and gastrointestinal diseases and disorders (miscellaneous).

5 Pharmacology and Biochemistry

5.1 Mechanism of Action

AT-1001 is an orally administered octapeptide zonulin receptor antagonist that appears to exert its inhibitory effect on gliadin-induced tight junction disassembly by blocking putative zonulin receptors on the luminal surface of the small intestine.

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