Select a section from the left sidebar
Naringin
- Family: Plantae - Apiaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Flavonoid Glycoside
| Canonical Smiles | OC[C@H]1O[C@@H](Oc2cc(O)c3c(c2)O[C@@H](CC3=O)c2ccc(cc2)O)[C@@H]([C@H]([C@@H]1O)O)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O |
|---|---|
| InChI | 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 |
| Formula | C27H32O14 |
| HBA | 14 |
| HBD | 8 |
| MW | 580.54 |
| Rotatable Bonds | 6 |
| TPSA | 225.06 |
| LogP | -1.17 |
| Number Rings | 5 |
| Number Aromatic Rings | 2 |
| Heavy Atom Count | 41 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.52 |
| Exact Mass | 580.18 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Coriandrum sativum | Apiaceae | Plantae | 4047 |
Showing of synonyms
Naringin
10236-47-2
Aurantiin
Naringoside
(2S)-Naringin
Naringenin 7-O-neohesperidoside
UNII-N7TD9J649B
Naringenin 7-Rhamnoglucoside
N7TD9J649B
CHEBI:28819
Naringenin-7-beta-neohesperidoside
EINECS 233-566-4
AI3-19008
DTXSID6022478
NARINGENIN-7-RHAMNOGLUCOSIDE
7-(2-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyloxy)-2,3-dihydro-4',5,7-trihydroxyflavone
4',5,7-trihydroxyflavanone 7-rhamnoglucoside
4',5,7-Trihydroxyflavanone-7-rhamnoglucoside
NARINGIN (USP-RS)
NARINGIN [USP-RS]
5-Hydroxy-2-(4-hydroxyphenyl)-7-(2-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyloxy)-4-chromanon
Naringenin 7-O-alpha-L-rhamnosyl-(1->2)-beta-D-glucoside
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
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)-
Naringenin-7-hesperidoside
Naringenin 7-O-(alpha-L-rhamnosyl-(1->2)-beta-D-glucoside)
Naringin extract
Naringenin Glycoside
DTXCID302478
233-566-4
977038-87-1
Naringin hydrate
Naringenine-7-rhamnosidoglucoside
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
4'5-diOH-Flavone-7-rhgluc
CHEMBL451532
(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
MFCD00148888
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl 2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside
SR-01000736681
Naringin (Standard)
Naringin (Naringoside)
NARINGIN [MI]
132203-74-8
Prestwick0_000467
Prestwick1_000467
Prestwick2_000467
Prestwick3_000467
AURANTIIN [WHO-DD]
SCHEMBL23432
BSPBio_000574
Cid_25075
MLS000069459
BIDD:ER0262
DivK1c_000247
SPBio_002513
BPBio1_000632
Cid_442428
GTPL4738
MEGxp0_001877
ACon1_000139
HMS500M09
HY-N0153R
KBio1_000247
NINDS_000247
CITRUS NARINGININE [VANDF]
HMS2231M18
HY-N0153
MSK40036
BDBM50241582
S2329
AKOS016034302
CCG-208591
CS-5632
ON04250
IDI1_000247
NCGC00142617-01
NCGC00142617-02
NCGC00142617-03
1217471-78-7
1ST40036
AS-12929
SMR000059108
XN167836
NS00014639
C09789
Q418469
SR-01000736681-4
SR-01000736681-5
BRD-K02953697-001-09-2
BRD-K02953697-002-03-3
Naringenin 7-rhamnoglucoside hydrate
4,5,7-Trihydroxyflavanone 7-rhamnoglucoside hydrate
(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-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
7-[[2-O-(6-Deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-5-hydroxy-2(S)-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
ZWN
- Msaada K, Ben Jemia M, et al. (2014). Antioxidant activity of methanolic extracts from three coriander (Coriandrum sativum L.) fruit varieties. Arabian Journal of Chemistry,2014, in press. [View]
Pubchem:
442428
Cas:
10236-47-2
Gnps:
CCMSLIB00004704298
Zinc:
ZINC000008143604
Kegg Ligand:
C09789
Chebi:
28819
Nmrshiftdb2:
60022485
Metabolights:
MTBLC28819
Chembl:
CHEMBL451532
Comptox:
DTXSID6022478
Drugbank:
DB16859
Pdb Ligand:
ZWN
Bindingdb:
50241582
Selleck:
Naringin(Naringoside)
CPRiL:
55843
SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(cc3)OC(OCCC4)C4OC5CCCCO5
Level: 3
Mol. Weight: 580.54 g/mol
SMILES: O=C1CCOc(c12)cc(cc2)OC(OCCC3)C3OC4CCCCO4
Level: 2
Mol. Weight: 580.54 g/mol
SMILES: c1ccccc1C(CC2=O)Oc(c23)cc(cc3)OC4CCCCO4
Level: 2
Mol. Weight: 580.54 g/mol
SMILES: O=C1CCOc(c12)cc(cc2)OC3CCCCO3
Level: 1
Mol. Weight: 580.54 g/mol
SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3
Level: 1
Mol. Weight: 580.54 g/mol
SMILES: C1OCCCC1OC2CCCCO2
Level: 1
Mol. Weight: 580.54 g/mol
SMILES: c1cccc(c12)OCCC2=O
Level: 0
Mol. Weight: 580.54 g/mol
SMILES: C1CCOCC1
Level: 0
Mol. Weight: 580.54 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 580.54 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.77
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.190
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 3.7
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.850
- Plasma Protein Binding
- 75.38
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 9.450
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -3.570
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 0.570
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.460
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -6205.610
- Rat (Acute)
- 2.430
- Rat (Chronic Oral)
- 4.080
- Fathead Minnow
- 13.420
- Respiratory Disease
- Safe
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 519.270
- Hydration Free Energy
- -2.940
- Log(D) at pH=7.4
- 0.380
- Log(P)
- -0.37
- Log S
- -3.95
- Log(Vapor Pressure)
- -12.18
- Melting Point
- 189.56
- pKa Acid
- 4.31
- pKa Basic
- 5.88
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9394 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.9394 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.9224 |
| Death-associated protein kinase 1 | P53355 | DAPK1_HUMAN | Homo sapiens | 4 | 0.9224 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.9218 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.9218 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 4 | 0.8791 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 4 | 0.8791 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8659 |
| Pantothenate synthetase | P9WIL5 | PANC_MYCTU | Mycobacterium tuberculosis | 3 | 0.8659 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8284 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.8284 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.8180 |
| Aldo-keto reductase family 1 member B1 | P15121 | ALDR_HUMAN | Homo sapiens | 3 | 0.8180 |
| Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 4 | 0.8066 |
| Anthocyanidin 3-O-glucosyltransferase UFGT | P51094 | UFOG_VITVI | Vitis vinifera | 4 | 0.8066 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8047 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8047 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7872 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7872 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 3 | 0.7870 |
| Methionine aminopeptidase 1 | P53582 | MAP11_HUMAN | Homo sapiens | 3 | 0.7870 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.7764 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.7764 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.7705 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.7705 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7627 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7627 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7622 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7622 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7614 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7614 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.7613 |
| Peroxisome proliferator-activated receptor gamma | P37231 | PPARG_HUMAN | Homo sapiens | 4 | 0.7613 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7599 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7599 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7574 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7574 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7513 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7513 |
| Threonine--tRNA ligase | P0A8M3 | SYT_ECOLI | Escherichia coli | 3 | 0.7459 |
| Threonine--tRNA ligase | P0A8M3 | SYT_ECOLI | Escherichia coli | 3 | 0.7459 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7432 |
| beta-glucosidase | Q92AS9 | Q92AS9_LISIN | Listeria innocua serovar 6a | 3 | 0.7432 |
| Beta-galactoside-specific lectin 1 | P81446 | ML1_VISAL | Viscum album | 3 | 0.7427 |
| Beta-galactoside-specific lectin 1 | P81446 | ML1_VISAL | Viscum album | 3 | 0.7427 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7420 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7420 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.7360 |
| Valacyclovir hydrolase | Q86WA6 | BPHL_HUMAN | Homo sapiens | 3 | 0.7360 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.7229 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 4 | 0.7229 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7214 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7214 |
| YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein | Q5SHN1 | Q5SHN1_THET8 | Thermus thermophilus | 3 | 0.7135 |
| YbaK/aminoacyl-tRNA synthetase-associated domain-containing protein | Q5SHN1 | Q5SHN1_THET8 | Thermus thermophilus | 3 | 0.7135 |
| 23S rRNA (guanine(745)-N(1))-methyltransferase | P36999 | RLMA_ECOLI | Escherichia coli | 3 | 0.7120 |
| 23S rRNA (guanine(745)-N(1))-methyltransferase | P36999 | RLMA_ECOLI | Escherichia coli | 3 | 0.7120 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7115 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7115 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7089 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7089 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.7088 |
| Serine/threonine-protein kinase 10 | O94804 | STK10_HUMAN | Homo sapiens | 3 | 0.7088 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | Q3JRA0 | ISPF_BURP1 | Burkholderia pseudomallei | 4 | 0.7079 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | Q3JRA0 | ISPF_BURP1 | Burkholderia pseudomallei | 4 | 0.7079 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7063 |
| Glycogen synthase kinase-3 beta | P49841 | GSK3B_HUMAN | Homo sapiens | 3 | 0.7063 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 5 | 0.7011 |
| Poly [ADP-ribose] polymerase tankyrase-2 | Q9H2K2 | TNKS2_HUMAN | Homo sapiens | 5 | 0.7011 |
| Small heat shock protein StHsp14.0 | Q970D9 | Q970D9_SULTO | Sulfurisphaera tokodaii | 3 | 0.7010 |
| Small heat shock protein StHsp14.0 | Q970D9 | Q970D9_SULTO | Sulfurisphaera tokodaii | 3 | 0.7010 |