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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

Larazotide Acetate
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 Weight 725.8 g/mol
Molecular Formula C32H55N9O10
XLogP3-3.6
Hydrogen Bond Donor Count9
Hydrogen Bond Acceptor Count11
Rotatable Bond Count21
Exact Mass725.40718899 g/mol
Monoisotopic Mass725.40718899 g/mol
Topological Polar Surface Area301 Ų
Heavy Atom Count51
Formal Charge0
Complexity1290
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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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