HYDIA

HYDIA

Identifiers
IUPAC name (1S,2R,3R,5R,6S)-2-amino-3-hydroxybicyclo[3.1.0]hexane-2,6-dicarboxylic acid
PubChem (CID)	9794223
ChemSpider	7969990
Chemical and physical data
Formula	C8H11NO5
Molar mass	201.176 g/mol
3D model (Jmol)	Interactive image
SMILES C1[C@H]2[C@@H]([C@H]2[C@@]([C@@H]1O)(C(=O)O)N)C(=O)O
InChI InChI=1S/C8H11NO5/c9-8(7(13)14)3(10)1-2-4(5(2)8)6(11)12/h2-5,10H,1,9H2,(H,11,12)(H,13,14)/t2-,3+,4-,5-,8-/m0/s1 Key:NTPXNEQCDPWJQA-AZDHXYLBSA-N
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HYDIA is a drug that is used in neuroscience research, which acts as a potent and selective antagonist for the group II metabotropic glutamate receptors (mGluR_2/3). It has been useful in the mapping of the group II mGluR receptor proteins and their molecular modeling.^[1] HYDIA is similar in structure to group II mGluR agonists such as eglumegad and LY-404,039, but the addition of the 3-hydroxy group reverses the activity to a competitive antagonist. Other derivatives such as the 3-benzyloxy ether are more potent antagonists than HYDIA itself.^[2]

References

1. Lundström L, Kuhn B, Beck J, Borroni E, Wettstein JG, Woltering TJ, Gatti S (July 2009). "Mutagenesis and molecular modeling of the orthosteric binding site of the mGlu2 receptor determining interactions of the group II receptor antagonist (3)H-HYDIA". Chemmedchem. 4 (7): 1086–94. doi:10.1002/cmdc.200900028. PMID 19402024.
2. Woltering TJ, Adam G, Huguenin P, Wichmann J, Kolczewski S, Gatti S, Bourson A, Kew JN, Richards G, Kemp JA, Mutel V, Knoflach F (February 2008). "Asymmetric synthesis and receptor pharmacology of the group II mGlu receptor ligand (1S,2R,3R,5R,6S)-2-amino-3-hydroxy-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid-HYDIA". Chemmedchem. 3 (2): 323–35. doi:10.1002/cmdc.200700226. PMID 18058780.