Natural Product (NP) Details

General Information of the NP (ID: NP9386)
Name
Naringin
Synonyms
naringin; 10236-47-2; Naringoside; UNII-N7TD9J649B; Naringenin 7-O-neohesperidoside; Naringenine-7-rhamnosidoglucoside; 4'5-diOH-Flavone-7-rhgluc; CHEMBL451532; N7TD9J649B; CHEBI:28819; Naringenin 7-Rhamnoglucoside; C27H32O14; aurantiin; (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one; (S)-7-(((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one; 7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one; Naringenin 7-O-[alpha-L-rhamnosyl-(1->2)-beta-D-glucoside]; MFCD00148888; (2S)-Naringin; SR-01000736681; Naringenin,(S); Naringenin-7-beta-neohesperidoside; (S)-7-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2-yloxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one; EINECS 233-566-4; yphenyl)chroman-4-one; Naringin (Naringoside); AI3-19008; Prestwick0_000467; Prestwick1_000467; Prestwick2_000467; Prestwick3_000467; 4',5,7-trihydroxyflavanone 7-rhamnoglucoside; SCHEMBL23432; BSPBio_000574; 7-(2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone; cid_25075; MLS000069459; BIDD:ER0262; DivK1c_000247; SPBio_002513; BPBio1_000632; cid_442428; GTPL4738; MEGxp0_001877; 3-Bromo-4-isopropoxybenzoicacid; DTXSID6022478; ACon1_000139; HMS500M09; KBio1_000247; NINDS_000247; HMS2231M18; HY-N0153; ZINC8143604; BDBM50241582; s2329; AKOS016034302; CCG-208591; CS-5632; MCULE-5348711723; IDI1_000247; NCGC00142617-01; NCGC00142617-02; NCGC00142617-03; 5-Hydroxy-2-(4-hydroxyphenyl)-7-(2-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyloxy)-4-chromanon; AS-12929; SMR000059108; ST072162; N2371; C09789; J10148; 236N472; Q418469; SR-01000736681-4; SR-01000736681-5; BRD-K02953697-001-09-2; BRD-K02953697-002-03-3; Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucoside; naringenin 7-O-(alpha-L-rhamnosyl-(1,2)-beta-D-glucoside); (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside; (2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-chromen-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-betaD-glucopyranoside; (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one; (2S)-7-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one; (2S)-7-[(2S,4S,5S,3R,6R)-3-((2S,6S,3R,4R,5R)-3,4,5-trihydroxy-6-methyl(2H-3,4, 5,6-tetrahydropyran-2-yloxy))-4,5-dihydroxy-6-(hydroxymethyl)(2H-3,4,5,6-tetra hydropyran-2-yloxy)]-5-hydroxy-2-(4-hydrox; (2S)-7-[(2S,4S,5S,3R,6R)-3-((2S,6S,3R,4R,5R)-3,4,5-trihydroxy-6-methyl(2H-3,4, 5,6-tetrahydropyran-2-yloxy))-4,5-dihydroxy-6-(hydroxymethyl)(2H-3,4,5,6-tetra hydropyran-2-yloxy)]-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one; (2S)-7-{[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one; (S)-7-((2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-2H-pyran-2-yloxy)-tetrahydro-2H-pyran-2-yloxy)-5-hydroxy-2-(4-hydroxyphenyl)chroman-4-one; 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannapyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl), (S)-; 4H-1-Benzopyran-4-one, 7-((2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-, (2S)-; 7-(2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyloxy)-2,3-dihydro-4,5,7-trihydroxyflavone;Naringin; 7-[[2-O-(6-Deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-5-hydroxy-2(S)-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
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Species Origin Citrus x rokugatsu ...     Click to Show/Hide
Citrus x rokugatsu
Kingdom: Viridiplantae
Phylum: Streptophyta
Class: Magnoliopsida
Order: Sapindales
Family: Rutaceae
Genus: Citrus
Species: Citrus x rokugatsu
Disease Ulcerative colitis [ICD-11: DD71] Investigative [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
Absporption
Caco-2 Permeability
 -6.764
 
MDCK Permeability
 -4.988
 
PAMPA
 +++
 
HIA
 ++
 
Distribution
VDss
 -0.242
 
PPB
 78.1%
 
BBB
 - - -
 
Metabolism
CYP1A2 inhibitor
 - - -
CYP1A2 substrate
 - - -
CYP2C19 inhibitor
 - - -
CYP2C19 substrate
 - - -
CYP2C9 inhibitor
 - - -
CYP2C9 substrate
 - - -
CYP2D6 inhibitor
 - - -
CYP2D6 substrate
 - - -
CYP3A4 inhibitor
 - - -
CYP3A4 substrate
 - - -
CYP2B6 inhibitor
 ++
CYP2B6 substrate
 - - -
CYP2C8 inhibitor
 - - -
HLM Stability
 - -
 
Excretion
CLplasma
 1.858
 
T1/2
 4.395
Toxicity
DILI
 +++
 
Rat Oral Acute Toxicity
 - - -
 
FDAMDD
 - - -
 
Respiratory
 - - -
 
Human Hepatotoxicity
 ++
 
Ototoxicity
 +++
 
Drug-induced Nephrotoxicity
 +++
 
Drug-induced Neurotoxicity
 - - -
 
Hematotoxicity
 - -
 
Genotoxicity
 +++
 
Tips: 1. For the classification endpoints, the prediction probability values are transformed into six symbols: 0-0.1 (- - -), 0.1-0.3 (- -), 0.3-0.5 (-), 0.5-0.7 (+), 0.7-0.9 (++), and 0.9-1.0 (+++). 2. Additionally, the corresponding relationships of the three labels are as follows: excellent; medium; poor.
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Formula
C27H32O14
PubChem CID
442428
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
CAS Number
CAS 10236-47-2
ChEBI ID
CHEBI:28819
Herb ID
HBIN036380
SymMap ID
SMIT00233
TCMSP ID
MOL005812
TTD Drug ID
D09VQM
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Trimetazidine      Angina pectoris     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Forty male Sprague-Dawley rats weighting ranged from 200 to 250 g were used in this study.
                    Experimental
                    Result(s)		 NAR, TMZ, or their combination could attenuate the Nrf-2 expression in the kidney tissue, following the renal IR injury through inhibition of lipid peroxidase, and enhancement of antioxidant activity.
          Doxorubicin      Solid tumour/cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model H9c2(2-1) CVCL_0286 Healthy Rattus norvegicus
                    Experimental
                    Result(s)		 Naringin protects myocardial cells from doxorubicin induced apoptosis partially by inhibiting the p38MAPK pathway.
Target and Pathway
Target(s) Sodium-independent organic anion transporter (SLCO1A2)  Molecule Info  [4]
References
Reference 1 Protective Effect of Naringin on DSS-Induced Ulcerative Colitis in Mice. J Agric Food Chem. 2018 Dec 19;66(50):13133-13140.
Reference 2 Protective effects of naringin and trimetazidine on remote effect of acute renal injury on oxidative stress and myocardial injury through Nrf-2 regulation. Pharmacol Rep. 2019 Dec;71(6):1059-1066.
Reference 3 Naringin protects myocardial cells from doxorubicin?induced apoptosis partially by inhibiting the p38MAPK pathway. Mol Med Rep. 2017 Dec;16(6):9457-9463.
Reference 4 Naringin is a major and selective clinical inhibitor of organic anion-transporting polypeptide 1A2 (OATP1A2) in grapefruit juice. Clin Pharmacol Ther. 2007 Apr;81(4):495-502.
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