Details of the Drug

General Information of Drug (ID: DMPQBWY)

Drug Name
(-)-englerin A
Synonyms Englerin A; (-)-englerin A; CHEBI:72441; (1R,3aR,4S,5R,7R,8S,8aR)-5-(glycoloyloxy)-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl (2E)-3-phenylacrylate; GTPL8372; SCHEMBL12280306
Indication
Disease Entry ICD 11 Status REF
Discovery agent N.A. Investigative [1]
Drug Type
Small molecular drug
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 442.5
Topological Polar Surface Area (xlogp) 4.8
Rotatable Bond Count (rotbonds) 8
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 6
Chemical Identifiers
Formula
C26H34O6
IUPAC Name
[(1S,2R,5R,6R,7S,8R,10R)-10-(2-hydroxyacetyl)oxy-1,5-dimethyl-8-propan-2-yl-11-oxatricyclo[6.2.1.02,6]undecan-7-yl] (E)-3-phenylprop-2-enoate
Canonical SMILES
C[C@@H]1CC[C@@H]2[C@@H]1[C@@H]([C@@]3(C[C@H]([C@]2(O3)C)OC(=O)CO)C(C)C)OC(=O)/C=C/C4=CC=CC=C4
InChI
InChI=1S/C26H34O6/c1-16(2)26-14-20(30-22(29)15-27)25(4,32-26)19-12-10-17(3)23(19)24(26)31-21(28)13-11-18-8-6-5-7-9-18/h5-9,11,13,16-17,19-20,23-24,27H,10,12,14-15H2,1-4H3/b13-11+/t17-,19-,20-,23-,24+,25+,26-/m1/s1
InChIKey
GACOFEKSDCOVMV-RRYXBOBMSA-N
Cross-matching ID
PubChem CID
46242512
ChEBI ID
CHEBI:72441
TTD ID
D0M6VZ

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Short transient receptor potential channel 4 (TRPC4) TTX0H5W TRPC4_HUMAN Agonist [2]
Short transient receptor potential channel 5 (TRPC5) TT32NQ1 TRPC5_HUMAN Agonist [2]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Enantioselective synthesis of (-)-englerins A and B. Angew Chem Int Ed Engl. 2010 May 3;49(20):3517-9.
2 (-)-Englerin is a potent and selective activator of TRPC4 and TRPC5 calcium channels. Angew Chem Int Ed Engl. 2015 Mar 16;54(12):3787-91.
3 Clinical pipeline report, company report or official report of Boehringer Ingelheim.
4 Block of TRPC5 channels by 2-aminoethoxydiphenyl borate: a differential, extracellular and voltage-dependent effect. Br J Pharmacol. 2005 Jun;145(4):405-14.
5 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 490).
6 The Na+/Ca2+ exchange inhibitor KB-R7943 potently blocks TRPC channels. Biochem Biophys Res Commun. 2007 Sep 14;361(1):230-6.
7 Bromoenol lactone inhibits voltage-gated Ca2+ and transient receptor potential canonical channels. J Pharmacol Exp Ther. 2011 Nov;339(2):329-40.
8 Identification of ML204, a novel potent antagonist that selectively modulates native TRPC4/C5 ion channels. J Biol Chem. 2011 Sep 23;286(38):33436-46.
9 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 489).