O-Methyl-Dauracine

Dipeptidyl peptidase 4 (DPP4) is expressed by specific bacterial taxa of the microbiota. Microbial DPP4 is able to decrease the active glucagon like peptide-1 (GLP-1) and disrupt glucose metabolism in mice with a leaky gut. Sitagliptin, has little effect on microbial DPP4. daurisoline-d4 (Dau-d4) is a selective microbial DPP4 inhibitor that improves glucose tolerance in diabetic mice. (dopamine D2 receptor dopamine transporter-mediated dopamine uptake)

General

Type : Alkaloid, Natural, Quinoline

Chemical_Nomenclature : (1~{R})-1-[[4-[5-[[(1~{R})-6,7-dimethoxy-2-methyl-3,4-dihydro-1~{H}-isoquinolin-1-yl]methyl]-2-methoxy-phenoxy]phenyl]methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1~{H}-isoquinoline

Canonical SMILES : CN1CCc2cc(c(cc2[C@H]1Cc3ccc(cc3)Oc4cc(ccc4OC)C[C@@H]5c6cc(c(cc6CCN5C)OC)OC)OC)OC

InChI : InChI=1S\/C39H46N2O6\/c1-40-16-14-27-21-35(43-4)37(45-6)23-30(27)32(40)18-25-8-11-29(12-9-25)47-39-20-26(10-13-34(39)42-3)19-33-31-24-38(46-7)36(44-5)22-28(31)15-17-41(33)2\/h8-13,20-24,32-33H,14-19H2,1-7H3\/t32-,33-\/m1\/s1

InChIKey : UHYCXSGUNAWVBW-CZNDPXEESA-N

Other name(s) : KYL  ||  daurisoline-d4  ||  Dau-d4  ||  O-Methyldauricine  ||  O,O-Dimethylcuspidaline  ||  O,O-Dimethyldauricinoline  ||  CHEMBL501861


MW : 638.79

Formula : C39H46N2O6

CAS_number : 2202-17-7

PubChem : 200521

UniChem : UHYCXSGUNAWVBW-CZNDPXEESA-N

Target

Families : O-Methyl-Dauracine ligand of proteins in family
DPP4N_Peptidase_S9

Structure :
8HAY

Protein :
bactn-BT4193

References (3)

Title : Microbial-host-isozyme analyses reveal microbial DPP4 as a potential antidiabetic target - Wang_2023_Science_381_eadd5787
Author(s) : Wang K , Zhang Z , Hang J , Liu J , Guo F , Ding Y , Li M , Nie Q , Lin J , Zhuo Y , Sun L , Luo X , Zhong Q , Ye C , Yun C , Zhang Y , Wang J , Bao R , Pang Y , Wang G , Gonzalez FJ , Lei X , Qiao J , Jiang C
Ref : Science , 381 :eadd5787 , 2023
Abstract :
PubMedSearch : Wang_2023_Science_381_eadd5787
PubMedID: 37535747
Gene_locus related to this paper: bactn-BT4193

Title : Microbial gatekeepers: unraveling the role of the gut microbiota enzyme DPP4 in diabetes management - Liao_2023_Trends.Biochem.Sci__
Author(s) : Liao L , Lin F , Gao J
Ref : Trends in Biochemical Sciences , : , 2023
Abstract :
PubMedSearch : Liao_2023_Trends.Biochem.Sci__
PubMedID: 37770288

Title : Effects of various isoquinoline alkaloids on in vitro 3H-dopamine uptake by rat striatal synaptosomes - Protais_1995_J.Nat.Prod_58_1475
Author(s) : Protais P , Arbaoui J , Bakkali EH , Bermejo A , Cortes D
Ref : Journal of Natural Products , 58 :1475 , 1995
Abstract :
PubMedSearch : Protais_1995_J.Nat.Prod_58_1475
PubMedID: 8676127