Compound Summary
Compound Information
naringin
Compound Name: | naringin |
Compound CID: | 442428 |
Synonyms: | naringin 10236-47-2 Naringoside Naringin hydrate UNII-N7TD9J649B More... |
Iupac Name: | (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 |
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 |
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 |
Isomeric Smiles: | C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=CC(=C4C(=O)C[C@H](OC4=C3)C5=CC=C(C=C5)O)O)CO)O)O)O)O)O |
Molecular Weight: | 580.5 |
Molecular Formula: | C27H32O14 |
Compound Structure
2D Structure:
3D Structure:
Computed Properties
naringin
Molecular Weight: | 580.5 |
Molecular Formula: | C27H32O14 |
Hydrogen Bond Donor Count: | 8 |
Hydrogen Bond Acceptor Count: | 14 |
Rotatable Bond Count: | 6 |
Heavy Atom Count: | 41 |
Complexity: | 884 |
Synonyms
naringin
| naringin | naringin |
|---|---|
naringin |
10236-47-2 |
Naringoside |
Naringin hydrate |
UNII-N7TD9J649B |
Naringenin 7-O-neohesperidoside |
Naringenine-7-rhamnosidoglucoside |
45-diOH-Flavone-7-rhgluc |
CHEMBL451532 |
N7TD9J649B |
CHEBI:28819 |
Naringenin 7-Rhamnoglucoside |
C27H32O14 |
7-(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yloxyoxan-2-yloxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one |
aurantiin |
(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 |
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 |
(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-yloxyoxan-2-yloxy-5-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one |
5-Hydroxy-2-(4-hydroxyphenyl)-7-(2-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyloxy)-4-chromanon |
AS-12929 |
SMR000059108 |
ST072162 |
XN167836 |
N2371 |
C09789 |
J10148 |
236N472 |
A800566 |
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-yloxy-tetrahydropyran-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-yloxyoxan-2-yloxy-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-yloxy}oxan-2-yloxy}-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)- |
4H-1-Benzopyran-4-one,7-2-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyloxy-2,3-dihydro-5-hydroxy-2-(4-hydroxyphenyl)-,(S)- |
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-glucopyranosyloxy-5-hydroxy-2(S)-(4-hydroxyphenyl)-4H-1-benzopyran-4-one |
Experimental Data
naringin
| Species | Dosage | Unit | CG Lifespan(AVG/MED days) | TG Lifespan(AVG/MED days) | Lifespan Change(AVG/MED%) | CG Lifespan(MAX days) | TG Lifespan(MAX days) | Lifespan Change(MAX%) | Significant | Strain | Gender | PubMed | Active Label |
|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Saccharomyces cerevisiae | 100 | umol/L | NS | BY4742 | 31766122 | Inactive | |||||||
| Caenorhabditis elegans | 0.001 | % | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 0.00005 | % | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 0.0001 | % | Unclear | N2 | 33683565 | ||||||||
| Caenorhabditis elegans | 0.01 | % | Unclear | N2 | 33683565 | ||||||||
| Drosophila melanogaster | 0.3 | umol/L | 55.3 | 56.1 | 0.01 | 64 | 74 | 0.16 | S | w1118 | FEMALES | 29375370 | Active |
| Drosophila melanogaster | 0.5 | umol/L | 55.3 | 57.4 | 0.04 | 64 | 75 | 0.17 | S | w1118 | FEMALES | 29375370 | Active |
| Drosophila melanogaster | 0.5 | umol/L | 48.6 | 45.5 | -0.06 | 73 | 79 | 0.08 | S | w1118 | MALES | 29375370 | Inactive |
| Caenorhabditis elegans | 1 | umol/L | 22 | 28 | 0.27 | 54 | 54 | 0 | S | N2 | 29375370 | Active | |
| Caenorhabditis elegans | 5 | umol/L | 22 | 24 | 0.09 | 54 | 54 | 0 | S | N2 | 29375370 | Active | |
| Caenorhabditis elegans | 100 | umol/L | 22 | 25 | 0.14 | 54 | 49 | -0.09 | S | N2 | 29375370 | Active | |
| Caenorhabditis elegans | 0.5 | umol/L | 22 | 24 | 0.09 | 54 | 47 | -0.13 | NS | N2 | 29375370 | Inactive | |
| Drosophila melanogaster | 1 | umol/L | 55.3 | 59.8 | 0.08 | 64 | 78 | 0.22 | S | w1118 | FEMALES | 29375370 | Active |
| Caenorhabditis elegans | 10 | umol/L | 22 | 26 | 0.18 | 54 | 54 | 0 | S | N2 | 29375370 | Active | |
| Drosophila melanogaster | 1 | umol/L | 48.6 | 42.7 | -0.12 | 73 | 64 | -0.12 | S | w1118 | MALES | 29375370 | Inactive |
| Drosophila melanogaster | 0.3 | umol/L | 48.6 | 47.1 | -0.03 | 73 | 64 | -0.12 | NS | w1118 | MALES | 29375370 | Inactive |
Experimental Data Visualization
naringin
Statistics Data
naringin
| Species | Lifespan Change(AVG/MED%) | Lifespan Change(MAX%) | Count Reference | Count Data point |
|---|---|---|---|---|
| Caenorhabditis elegans | 0.27 | 0 | 2 | 9 |
| Drosophila melanogaster | 0.08 | 0.22 | 1 | 6 |
| Saccharomyces cerevisiae | 1 | 1 |
Statistics Data Visualization
naringin
