Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2149)
Drug Name
BRN-0075455
Synonyms
Bioflavonoid; Birutan; Birutan Forte; Rutin; Birutin; Eldrin; Globulariacitrin; Globularicitrin; Ilixanthin; Myrticolorin; Osyritrin; Oxyritin; Paliuroside; Phytomelin; Quercetin 3-O-rutinoside; Quercetin 3-rutinoside; Quercetin rhamnoglucosine; Quercetin-3-rutinoside; Quercetin-3beta-rutinoside; Rutabion; Rutin trihydrate; Rutine; Rutinic acid; Rutinion acid; Rutinum; Rutosid; Rutosido; Rutosidum; Rutozyd; Tanrutin; Venoruton; Violaquercitrin; rutoside; 153-18-4; 3-Rhamnoglucosylquercetin; 3-Rutinosyl quercetin; Melin; RUTIN; UNII-5G06TVY3R7
Indication Diabetes mellitus [ICD11: 5A10] Phase 2/3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 610.5 Topological Polar Surface Area 266
Heavy Atom Count 43 Rotatable Bond Count 6
Hydrogen Bond Donor Count 10 Hydrogen Bond Acceptor Count 16
Cross-matching ID
PubChem CID
5280805
PubChem SID
7941 ; 583769 ; 597190 ; 7890342 ; 8149167 ; 8616403 ; 11335819 ; 11361058 ; 11462030 ; 12015663 ; 14789521 ; 14936333 ; 24775672 ; 26719694 ; 29204545 ; 29216321 ; 39289828 ; 46386546 ; 47365182 ; 47588990 ; 47885411 ; 48414436 ; 48421832 ; 49681540 ; 50077472 ; 50077674 ; 50696375 ; 53789070 ; 57357881 ; 57394649 ; 85842433 ; 87575608 ; 88783231 ; 92297747 ; 92308256 ; 93165829 ; 93167038 ; 95154018 ; 96025184 ; 99301732 ; 103516775 ; 104091802 ; 104253605 ; 113854033 ; 124658987 ; 124757744 ; 124892311 ; 125164548 ; 126524764 ; 126688137
ChEBI ID
CHEBI:28527
CAS Number
153-18-4
TTD Drug ID
D09ALJ
Formula
C27H30O16
Canonical SMILES
CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
InChI
1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
InChIKey
IKGXIBQEEMLURG-NVPNHPEKSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
AS-35335 DM006048
5280804
Oxidation - Deglycosylation 1 [2]
Leucocyanidin DM006046
71629
Hydrolysis - Hydrolysis 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006511 BRN-0075455 AS-35335 Oxidation - Deglycosylation lrA [2]
MR006512 AS-35335 Leucocyanidin Hydrolysis - Hydrolysis bglA [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Alpha-L-rhamnosidase (lrA) DME1480 Bacillus subtilis
A0A385NJR4_9BACI
3.2.1.40
[2]
Alpha-L-rhamnosidase (lrA) DME1201 Bifidobacterium dentium
A0A1V8Q7P3_9BIF
3.2.1.40
[3]
Alpha-L-rhamnosidase (lrA) DME1759 Veillonella parvula
A0A179YH30_LACRH
3.2.1.40
[2]
Alpha-L-rhamnosidase (lrA) DME1481 Bacteroides thetaiotaomicron
A0A1H8EBM0_9BACE
3.2.1.40
[2]
Beta-glucosidase (bglA) DME1043 Malassezia furfur
A0A249DCH3_LACRH
3.2.1.21
[2]
Unclear metabolic mechanism (DME-unclear) DME2045 Eubacterium ramulus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME2047 Enterococcus casseliflavus Not Available Not Available [4]
⏷ Show the Full List of 7  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Alpha-L-rhamnosidase (lrA) DME1201 Km = 2190 microM
A0A1V8Q7P3_9BIF
[3]
References
1 ClinicalTrials.gov (NCT03437902) Impact of Rutin and Vitamin C Combination on Oxidative Stress, Insulin Sensitivity and Lipid Profile in Type 2 Diabetic Patients
2 Identification of rutin deglycosylated metabolites produced by human intestinal bacteria using UPLC-Q-TOF/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jun 1;898:95-100.
3 Metabolism of rutin and poncirin by human intestinal microbiota and cloning of their metabolizing alpha-L-rhamnosidase from Bifidobacterium dentium. J Microbiol Biotechnol. 2015 Jan;25(1):18-25.
4 Degradation of quercetin-3-glucoside in gnotobiotic rats associated with human intestinal bacteria. J Appl Microbiol. 2000 Dec;89(6):1027-37.

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