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

General Information of Drug (ID: DR2497)
Drug Name
Naringin
Synonyms
Naringenin 7-O-neohesperidoside; Naringenin 7-Rhamnoglucoside; Naringenin,(S); Naringenine-7-rhamnosidoglucoside; Naringin hydrate; Naringoside; SR-01000736681; aurantiin; naringin; (2S)-Naringin; 10236-47-2; 4',5,7-trihydroxyflavanone 7-rhamnoglucoside; 4'5-diOH-Flavone-7-rhgluc; AI3-19008; C27H32O14; CHEBI:28819; CHEMBL451532; EINECS 233-566-4; MFCD00148888; N7TD9J649B; Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]; Naringenin-7-beta-neohesperidoside; UNII-N7TD9J649B
Indication Ovarian cancer [ICD11: 2C73] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 580.5 Topological Polar Surface Area 225
Heavy Atom Count 41 Rotatable Bond Count 6
Hydrogen Bond Donor Count 8 Hydrogen Bond Acceptor Count 14
Cross-matching ID
PubChem CID
442428
ChEBI ID
CHEBI:28819
CAS Number
10236-47-2
Formula
C27H32O14
Canonical SMILES
CC1C(C(C(C(O1)OC2C(C(C(OC2OC3=CC(=C4C(=O)CC(OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O
InChI
1S/C27H32O14/c1-10-20(32)22(34)24(36)26(37-10)41-25-23(35)21(33)18(9-28)40-27(25)38-13-6-14(30)19-15(31)8-16(39-17(19)7-13)11-2-4-12(29)5-3-11/h2-7,10,16,18,20-30,32-36H,8-9H2,1H3/t10-,16-,18+,20-,21+,22+,23-,24+,25+,26-,27+/m0/s1
InChIKey
DFPMSGMNTNDNHN-ZPHOTFPESA-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
4',7Dihydroxyflavaone-7-O-neohesperidoside DM003965 N. A. Reduction - Dehydroxylation 1 [3]
4'-O-Acetoacetyl-naringin DM003962 N. A. Conjugation - Acetylation 1 [3]
4'-O-methyl-naringin DM003967 N. A. Conjugation - Methylationn 1 [3]
5,7Dihydroxyflavaone-7-O-neohesperidoside DM003966 N. A. Reduction - Dehydroxylation 1 [3]
5-O-Acetoacetyl-naringin DM003963 N. A. Conjugation - Acetylation 1 [3]
5-O-methyl-naringin DM003968 N. A. Conjugation - Methylationn 1 [3]
6-Hydroxyl-naringin DM003970 N. A. Oxidation - Hydrolyzationn 1 [3]
8-Hydroxyl-naringin DM003971 N. A. Oxidation - Hydrolyzationn 1 [3]
Naringenin DM003408
439246
Hydrolysis - Hydrolyzation 1 [3]
Naringin monoglucoside DM003969 N. A. Conjugation - Glucosylation 1 [3]
Naringin-O-sulfate DM003964 N. A. Conjugation - Sulfation 1 [3]
Neoeriocitrin DM003954
114627
Oxidation - Hydrolyzationn 1 [3]
Rhoifolin DM003961
5282150
Oxidation - Dehydrogenation 1 [3]
4'-O-Methyl-naringenin DM003953 N. A. Conjugation - Methylationn 2 [3]
5,7-Dihydroxyflavanone DM003960
238782
Reduction - Dehydroxylation 2 [3]
5-O-Methyl-neoeriocitrin DM003957 N. A. Conjugation - Methylationn 2 [3]
6-Hydroxyl-naringenin DM003949 N. A. Oxidation - Hydrolyzationn 2 [3]
8-Hydroxyl-naringeni DM003951 N. A. Oxidation - Hydrolyzationn 2 [3]
Apigenin DM003396
5280443
Reduction - Hydrogenation 2 [3]
Eriodictyol DM003394
440735
Oxidation - Hydrolyzationn 2 [3]
Homoeriodictyol-7-O-neohesperidoside DM003956 N. A. Conjugation - Methylationn 2 [3]
Naringenin-4'-O-glucoside DM003959
42607906
Conjugation - Glucosylation 2 [3]
Naringenin-5-O-glucoside DM003958 N. A. Conjugation - Glucosylation 2 [3]
Neohesperidin DM003955
442439
Conjugation - Methylation 2 [3]
p-Coumaric acid DM003945
637542
Other reaction - Ring cleavage reaction 2 [3]
3-(4-Hydroxyphenyl) propionic acid DM003390
10394
Reduction - Hydrogenation 3 [3]
6-Hydroxyl-4'-O-methyl-naringenin DM003950 N. A. Conjugation - Methylationn 3 [3]
8-Hydroxyl-4'-O-methyl-naringenin DM003952 N. A. Conjugation - Methylationn 3 [3]
Caffeic acid DM003530
689043
Oxidation - Hydrolyzationn 3 [3]
Cinnamic acid DM003948
444539
Reduction - Dehydroxylation 3 [3]
Hesperetin DM003395
72281
Hydrolysis - Hydrolyzation 3 [3]
Hesperetin DM003395
72281
Oxidation - Hydrolyzationn 3 [3]
Hesperetin DM003395
72281
Conjugation - Methylationn 3 [3]
3-(3',4'-dihydroxyphenyl)propionic acid DM002604
348154
Oxidation - Hydrolyzationn 4 [3]
3-Phenylpropionic acid DM003391
107
Reduction - Dehydroxylation 4 [3]
⏷ Show the Full List of 35  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004309 Naringin Naringenin Hydrolysis - Hydrolyzation Unclear [3]
MR004324 Naringin Neoeriocitrin Oxidation - Hydrolyzationn Unclear [3]
MR004333 Naringin Rhoifolin Oxidation - Dehydrogenation Unclear [3]
MR004334 Naringin 4'-O-Acetoacetyl-naringin Conjugation - Acetylation Unclear [3]
MR004335 Naringin 5-O-Acetoacetyl-naringin Conjugation - Acetylation Unclear [3]
MR004336 Naringin Naringin-O-sulfate Conjugation - Sulfation Unclear [3]
MR004337 Naringin 4',7Dihydroxyflavaone-7-O-neohesperidoside Reduction - Dehydroxylation Unclear [3]
MR004338 Naringin 5,7Dihydroxyflavaone-7-O-neohesperidoside Reduction - Dehydroxylation Unclear [3]
MR004339 Naringin 4'-O-methyl-naringin Conjugation - Methylationn Unclear [3]
MR004340 Naringin 5-O-methyl-naringin Conjugation - Methylationn Unclear [3]
MR004341 Naringin Naringin monoglucoside Conjugation - Glucosylation Unclear [3]
MR004342 Naringin 6-Hydroxyl-naringin Oxidation - Hydrolyzationn Unclear [3]
MR004343 Naringin 8-Hydroxyl-naringin Oxidation - Hydrolyzationn Unclear [3]
MR004310 Naringenin p-Coumaric acid Other reaction - Ring cleavage reaction Unclear [3]
MR004316 Naringenin 6-Hydroxyl-naringenin Oxidation - Hydrolyzationn Unclear [3]
MR004318 Naringenin 8-Hydroxyl-naringeni Oxidation - Hydrolyzationn Unclear [3]
MR004320 Naringenin Eriodictyol Oxidation - Hydrolyzationn Unclear [3]
MR004322 Naringenin 4'-O-Methyl-naringenin Conjugation - Methylationn Unclear [3]
MR004329 Naringenin Naringenin-5-O-glucoside Conjugation - Glucosylation Unclear [3]
MR004330 Naringenin Naringenin-4'-O-glucoside Conjugation - Glucosylation Unclear [3]
MR004331 Naringenin 5,7-Dihydroxyflavanone Reduction - Dehydroxylation Unclear [3]
MR004332 Naringenin Apigenin Reduction - Hydrogenation Unclear [3]
MR004325 Neoeriocitrin Neohesperidin Conjugation - Methylation Unclear [3]
MR004327 Neoeriocitrin Homoeriodictyol-7-O-neohesperidoside Conjugation - Methylationn Unclear [3]
MR004328 Neoeriocitrin 5-O-Methyl-neoeriocitrin Conjugation - Methylationn Unclear [3]
MR004323 4'-O-Methyl-naringenin Hesperetin Oxidation - Hydrolyzationn Unclear [3]
MR004317 6-Hydroxyl-naringenin 6-Hydroxyl-4'-O-methyl-naringenin Conjugation - Methylationn Unclear [3]
MR004319 8-Hydroxyl-naringeni 8-Hydroxyl-4'-O-methyl-naringenin Conjugation - Methylationn Unclear [3]
MR004321 Eriodictyol Hesperetin Conjugation - Methylationn Unclear [3]
MR004326 Neohesperidin Hesperetin Hydrolysis - Hydrolyzation Unclear [3]
MR004311 p-Coumaric acid 3-(4'-hydroxyphenyl)propionic acid Reduction - Hydrogenation Unclear [3]
MR004314 p-Coumaric acid Caffeic acid Oxidation - Hydrolyzationn Unclear [3]
MR004315 p-Coumaric acid Cinnamic acid Reduction - Dehydroxylation Unclear [3]
MR004312 3-(4'-hydroxyphenyl)propionic acid 3-(3',4'-dihydroxyphenyl)propionic acid Oxidation - Hydrolyzationn Unclear [3]
MR004313 3-(4'-hydroxyphenyl)propionic acid 3-Phenylpropionic acid Reduction - Dehydroxylation Unclear [3]
⏷ Show the Full List of 35 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Alpha-L-rhamnosidase (lrA) DME1201 Bifidobacterium dentium
A0A1V8Q7P3_9BIF
3.2.1.40
[2]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Alpha-L-rhamnosidase (lrA) DME1201 Km = 320 microM
A0A1V8Q7P3_9BIF
[2]
References
1 Naringin sensitizes human prostate cancer cells to paclitaxel therapy. Prostate Int. 2018 Dec;6(4):126-135.
2 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.
3 Microbial Metabolism of Naringin and the Impact on Antioxidant Capacity

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