Ungeremine

Inhibitor of acetylcholinesterase and butyrylcholinesterase, with the IC(50) values of 0.10 and 1.21 microM

General

Type : Natural, Alkaloid, Phenanthrene, Phenanthridinium

Chemical_Nomenclature : 5,7-dioxa-12-azoniapentacyclo[10.6.1.02,10.04,8.015,19]nonadeca-1(18),2,4(8),9,11,15(19),16-heptaen-17-ol

Canonical SMILES : C1C[N+]2=CC3=CC4=C(C=C3C5=CC(=CC1=C52)O)OCO4

InChI : InChI=1S\/C16H11NO3\/c18-11-3-9-1-2-17-7-10-4-14-15(20-8-19-14)6-12(10)13(5-11)16(9)17\/h3-7H,1-2,8H2\/p+1

InChIKey : DFQOXFIPAAMFAU-UHFFFAOYSA-O

Other name(s) : 9EVC5B2RPS  ||  Lycoranium, 1,2,3,3a,6,7,12b,12c-octadehydro-2-hydroxy-  ||  DTXSID50175439  ||  4,5-Dihydro-2-hydroxy-(1,3)dioxolo(4,5-j)pyrrolo(3,2,1-de)phenanthridinium  ||  (1,3)Dioxolo(4,5-j)pyrrolo(3,2,1-de)phenanthridinium, 4,5-dihydro-2-hydroxy-  ||  RefChem:933810  ||  Lycobetaine  ||  CHEMBL253553  ||  SCHEMBL20741474  ||  HY-N1971  ||  Lycobetaine chloride


MW : 266.27

Formula : C16H12NO3+

CAS_number : 2121-12-2

PubChem : 159646,    5351323

UniChem : DFQOXFIPAAMFAU-UHFFFAOYSA-O

Target

Families : Ungeremine ligand of proteins in family
ACHE BCHE

Protein :
human-ACHE human-BCHE

References (4)

Title : Amaryllidaceae alkaloids from the bulbs of Crinum latifolium L. and their cholinesterase inhibitory activities - Chaichompoo_2023_Phytochemistry__113929
Author(s) : Chaichompoo W , Rojsitthisak P , Pabuprapap W , Siriwattanasathien Y , Yotmanee P , Suksamrarn A
Ref : Phytochemistry , :113929 , 2023
Abstract :
PubMedSearch : Chaichompoo_2023_Phytochemistry__113929
PubMedID: 37984589

Title : Alkaloids with cholinesterase inhibitory activities from the bulbs of Crinum x amabile Donn ex Ker Gawl - Chaichompoo_2022_Phytochemistry_205_113473
Author(s) : Chaichompoo W , Rojsitthisak P , Pabuprapap W , Siriwattanasathien Y , Yotmanee P , Suksamrarn A
Ref : Phytochemistry , 205 :113473 , 2022
Abstract :
PubMedSearch : Chaichompoo_2022_Phytochemistry_205_113473
PubMedID: 36244402

Title : Two new alkaloids from Crinum asiaticum var. japonicum - Endo_2019_J.Nat.Med_73_648
Author(s) : Endo Y , Sugiura Y , Funasaki M , Kagechika H , Ishibashi M , Ohsaki A
Ref : J Nat Med , 73 :648 , 2019
Abstract :
PubMedSearch : Endo_2019_J.Nat.Med_73_648
PubMedID: 30963375

Title : Isolation of the acetylcholinesterase inhibitor ungeremine from Nerine bowdenii by preparative HPLC coupled on-line to a flow assay system - Rhee_2004_Biol.Pharm.Bull_27_1804
Author(s) : Rhee IK , Appels N , Hofte B , Karabatak B , Erkelens C , Stark LM , Flippin LA , Verpoorte R
Ref : Biol Pharm Bull , 27 :1804 , 2004
Abstract :
PubMedSearch : Rhee_2004_Biol.Pharm.Bull_27_1804
PubMedID: 15516727