upacicalcet   Click here for help

GtoPdb Ligand ID: 12235

Synonyms: Upasita®
Approved drug
upacicalcet is an approved drug (Japan (2021))
Compound class: Synthetic organic
Comment: Upacicalcet is an amino acid-derived compound trhat acts as a calcium-sensing receptors (CaSR) positive allosteric modulator (PAM) [2]. In silico and in vitro studies revealed that upacicalcet targets the amino acid binding site of CaSR, and binds competitively with L-tryptophan.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 9
Hydrogen bond donors 5
Rotatable bonds 7
Topological polar surface area 167.2
Molecular weight 351.76
XLogP -3.1
No. Lipinski's rules broken 0
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Canonical SMILES O=C(Nc1cc(cc(c1C)Cl)S(=O)(=O)O)NC[C@@H](C(=O)O)N
Isomeric SMILES Cc1c(cc(cc1Cl)S(=O)(=O)O)NC(=O)NC[C@@H](C(=O)O)N
InChI InChI=1S/C11H14ClN3O6S/c1-5-7(12)2-6(22(19,20)21)3-9(5)15-11(18)14-4-8(13)10(16)17/h2-3,8H,4,13H2,1H3,(H,16,17)(H2,14,15,18)(H,19,20,21)/t8-/m0/s1
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (Japan (2021))
IUPAC Name Click here for help
(2S)-2-amino-3-[(3-chloro-2-methyl-5-sulfophenyl)carbamoylamino]propanoic acid
International Nonproprietary Names Click here for help
INN number INN
10796 upacicalcet
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Specialist databases
GPCRdb Ligand upacicalcet
Other databases
CAS Registry No. 1333218-50-0 (source: WHO INN record)
GtoPdb PubChem SID 473153823
PubChem CID 53374467
Search Google for chemical match using the InChIKey LHEYGVSDVBEYQF-QMMMGPOBSA-N
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UniChem Compound Search for chemical match using the InChIKey LHEYGVSDVBEYQF-QMMMGPOBSA-N
UniChem Connectivity Search for chemical match using the InChIKey LHEYGVSDVBEYQF-QMMMGPOBSA-N