Rutin

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Rutin are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Rutin?

The molecule Rutin presents a molecular formula of C27H30O16 and its IUPAC name is 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one.

Rutin is a small molecule that belongs to the class of compounds known as flavonoids. Flavonoids are a group of plant-derived compounds that have a wide range of biological activities, including antioxidant, anti-inflammatory, and vasoprotective effects..

Rutin belongs naturally in a variety of plants, including buckwheat, asparagus, and citrus fruits, and is often extracted from these plants for use as a dietary supplement. It is thought to have a number of potential health benefits, including reducing the risk of heart disease and improving circulation..

One of the main mechanisms by which rutin is thought to exert its beneficial effects is by acting as an antioxidant. Antioxidants are compounds that help to protect the body against the damaging effects of free radicals, which are reactive molecules that can cause oxidative stress and contribute to the development of chronic diseases. Rutin has been found to have a strong antioxidant activity in laboratory studies, and may help to reduce the risk of oxidative stress-related conditions such as cancer and cardiovascular disease..

In addition to its antioxidant activity, rutin has also been found to have anti-inflammatory effects, which may be beneficial for the treatment of conditions such as arthritis and asthma. It has also been suggested that rutin may have a protective effect on the blood vessels, and may help to reduce the risk of blood clots and improve circulation..

Despite its potential health benefits, rutin is not approved as a drug in the United States and is not regulated by the Food and Drug Administration. More research is needed to fully understand its safety and effectiveness as a therapeutic agent..

Summary

From all the above, this molecule is a small molecule that belongs naturally in a variety of plants and is thought to have a number of potential health benefits, including antioxidant, anti-inflammatory, and vasoprotective effects. However, more research is needed to fully understand its safety and effectiveness as a therapeutic agent..

3D structure

Cartesian coordinates

Geometry of Rutin in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Rutin IKGXIBQEEMLURG-NVPNHPEKSA-N chemical compound 2D structure molecule svg
Rutin

 

Molecule descriptors

 
IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
InChI codeInChI=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
InChI KeyIKGXIBQEEMLURG-NVPNHPEKSA-N
SMILESC[C@@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3c(-c4ccc(O)c(O)c4)oc4cc(O)cc(O)c4c3=O)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 153-18-4
  • 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4-OXO-4H-CHROMEN-3-YL 6-O-(6-DEOXY-ALPHA-L-MANNOPYRANOSYL)-BETA-D-GLUCOPYRANOSIDE
  • 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4H-CHROMEN-4-ONE-3-YL 6-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOSIDE
  • 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3
  • 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one
  • 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one;Rutin
  • 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)methyl)tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one
  • 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one
  • 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
  • 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
  • 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-mannopyranoside
  • 207671-50-9
  • 3'4'5,7-tetOH-Flavone-3-rut
  • 3,3',4',5,5',7-Hexahydroxyflavone (6-O-alpha-L-rhamnosyl-beta-D-glucoside)
  • 3,3',4',5,7-PENTAHYDROXYFLAVONE-3-RHAMNOGLUCOSIDE
  • 3,3',4',5,7-Pentahydroxyflavone 3-rutinoside
  • 3,3',4',5,7-Pentahydroxyflavone-3-rutinoside
  • 3,3,4,5,7-PENTAHYDROXYFLAVONE-3-RHAMNOGLUCOSIDE
  • 3-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
  • 3-RHAMNOGLUCOSIDE OF 5,7,3',4'-TETRAHYDROXYFLAVONOL
  • 3-Rhamnoglucoside of 3,3',4',5,7-pentahydroxyflavone
  • 3-Rhamnoglucosylquercetin
  • 3-Rutinosyl quercetin
  • 3-[[6-O-(6-Deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
  • 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
  • 4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]-oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
  • 4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
  • 4H-1-Benzopyran-4-one,3-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
  • 5G06TVY3R7
  • A809400
  • A8241DA0-6EC6-48BA-BD10-3F7BD61D42CE
  • AB00374708-09
  • ACon1_000075
  • AI3-19098
  • BDBM50217942
  • BIDD:ER0377
  • BIDD:PXR0020
  • BRN 0075455
  • Bioflavonoid
  • Birutan
  • Birutan Forte
  • Birutin
  • C.I. 75730
  • C05625
  • CCG-100999
  • CCRIS 7564
  • CS-5573
  • D08499
  • DB01698
  • DS-9708
  • DSSTox_CID_2326
  • DSSTox_GSID_22326
  • DSSTox_RID_76549
  • DivK1c_000644
  • Eldrin
  • Flavone, 3,3',4',5,7-pentahydroxy-, 3-(O-rhamnosylglucoside)
  • Globulariacitrin
  • Globularicitrin
  • Glucopyranoside, quercetin-3 6-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-
  • Glucopyranoside, quercetin-3 6-O-alpha-L-rhamnopyranosyl-, beta-D
  • HMS2051B06
  • HMS502A06
  • HY-N0148
  • IDI1_000644
  • Ilixanthin
  • KBio1_000644
  • MEGxp0_000068
  • MFCD00006830
  • MLS000759398
  • MLS001424098
  • Melin
  • Myrticolorin
  • NC00249
  • NCGC00160628-01
  • NCGC00160628-02
  • NCGC00160628-03
  • NCGC00260150-01
  • NINDS_000644
  • NSC 9220
  • NSC-9220
  • Neoisorutin
  • Novarrutina
  • Osyritrin
  • Oxyritin
  • Paliuroside
  • Phytomelin
  • Q-201691
  • Q407857
  • QUERCETIN 3-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOPYRANOSIDE
  • Quercetin 3-O-beta-D-rutinoside
  • Quercetin 3-O-beta-delta-rutinoside
  • Quercetin 3-O-rutinoside
  • Quercetin 3-rhamnoglucoside
  • Quercetin 3-rutinoside
  • Quercetin rhamnoglucosine
  • Quercetin, 3-(6-0-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside)
  • Quercetin, 3-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside)
  • Quercetin-3-rutinoside
  • Quercetin-3beta-rutinoside
  • Quercetol 3-rhamnoglucoside
  • Quercitin 3-rutinoside
  • R0035
  • RUT
  • RUTIN
  • Rutabion
  • Rutin
  • Rutin (Rutoside)
  • Rutin from Sophora japonica L.
  • Rutin trihydrate
  • Rutin,(S)
  • Rutine
  • Rutinic acid
  • Rutinion acid
  • Rutinoside, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl
  • Rutinoside, quercetin-3, beta-
  • Rutinum
  • Rutosid
  • Rutoside (INN)
  • Rutoside (rutin)
  • Rutosido
  • Rutosidum
  • Rutozyd
  • SMR000112560
  • SR-01000759399
  • SR-01000759399-5
  • Sophorin
  • Tanrutin
  • USAF CF-5
  • Venoruton
  • Violaquercetrin
  • Violaquercitrin
  • Vitamin P
  • Yunxianggan
  • beta-Quercetin-3-rutinoside
  • cid_5280805
  • hydroxyethylrutoside
  • methyltetrahydro-2H-pyran-2-yloxy)methyl)
  • quercetin-3-O-rutinoside
  • rutoside
  • s2350
  • tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4096846
  • CAS-153-18-4
  • UNII-5G06TVY3R7
  • AKOS015895432
  • BRD-K20482099-001-01-1
  • BRD-K20482099-001-11-0
  • DTXSID3022326
  • CHEMBL226335
  • CHEBI:28527
  • Tox21_111945
  • Tox21_202602
  • Tox21_111945_1
  • EINECS 205-814-1
  • SCHEMBL23243

Physico-Chemical properties

IUPAC name2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
Molecular formulaC27H30O16
Molecular weight610.517
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity141.38
LogP-1.7
Topological polar surface area269.4

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.