Rutin






Names

    • Neoisorutin
    • 207671-50-9
    • RUT
    • CCRIS 7564
    • NCGC00160628-02
    • 2-(3,4-dihydroxyphenyl)-4,5-dihydroxy-3-(3,4,5-trihydroxy-6-((3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxymethyl)tetrahydropyran-2-yl)oxy-chromen-7-one
    • BIDD:PXR0020
    • SR-01000759399-5
    • HY-N0148R
    • ACon1_000075
    • Novarrutina
    • hydroxyethylrutoside
    • Globularicitrin
    • CCG-100999
    • RUTIN (QUERCETIN-3-O-RUTINOSIDE) (CONSTITUENT OF GINKGO) [DSC]
    • NSC-9220
    • 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
    • CS-5573
    • SMR000112560
    • RUTIN
    • Violaquercetrin
    • Quercetol 3-rhamnoglucoside
    • EINECS 205-814-1
    • Tox21_111945_1
    • Vitamin P', "3,3',4',5,7-Pentahydroxyflavone-3-rutinoside", 'quercetin-3-O-rutinoside
    • C05625
    • Osyritrin
    • 4H-1-Benzopyran-4-one, 3-[[6-O-(6-deoxy-.alpha.-L-mannopyranosyl)-.beta.-D-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
    • Quercetin 3-O-beta-D-rutinoside
    • Quercetin 3-rhamnoglucoside
    • Rutoside [INN:JAN:NF]
    • quercetin 3-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]
    • Tox21_111945
    • Rutosidum (INN-Latin)
    • Rutin [JAN:NF]
    • SR-01000759399
    • Glucopyranoside, quercetin-3 6-O-alpha-L-rhamnopyranosyl-, beta-D
    • MLS000759398
    • 3-Rutinosyl quercetin
    • 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
    • NCGC00160628-03
    • Phytomelin
    • Rutozyd
    • 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4H-CHROMEN-4-ONE-3-YL 6-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOSIDE
    • Rutosidum
    • Quercetin 3-rutinoside
    • Melin
    • IDI1_000644
    • Birutin
    • RUTOSIDE [WHO-DD]
    • DTXSID3022326
    • Ilixanthin
    • Rutin,(S)
    • 153-18-4
    • DS-9708
    • DB01698
    • CHEMBL226335
    • Birutan
    • 5G06TVY3R7
    • NCGC00160628-12
    • Paliuroside
    • Rutinion acid
    • Rutin from Sophora japonica L.
    • D08499
    • Rutosid
    • BRN 0075455', "3-Rhamnoglucoside of 3,3',4',5,7-pentahydroxyflavone", 'AI3-19098
    • EN300-18388402
    • NCGC00260150-01
    • Rutosido [INN-Spanish]
    • USAF CF-5
    • DTXCID802326
    • Rutoside (INN)
    • rutoside
    • CAS-153-18-4
    • cid_5280805
    • NC00249
    • -((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-
    • 5-18-05-00519 (Beilstein Handbook Reference)
    • 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3
    • C05CA01
    • Yunxianggan
    • Birutan Forte
    • Rutosidum [INN-Latin]
    • KBio1_000644
    • HMS502A06
    • Eldrin
    • Quercetin-3-rutinoside
    • BRD-K20482099-001-01-1
    • Globulariacitrin
    • Quercetin 3-O-rutinoside
    • Rutine
    • DivK1c_000644
    • BRD-K20482099-001-11-0
    • 2-(3,4-DIHYDROXYPHENYL)-5,7-DIHYDROXY-4-OXO-4H-CHROMEN-3-YL 6-O-(6-DEOXY-ALPHA-L-MANNOPYRANOSYL)-BETA-D-GLUCOPYRANOSIDE
    • Rutinum
    • Rutinic acid
    • NS00005273
    • UNII-5G06TVY3R7
    • QUERCETIN 3-O-.ALPHA.-L-RHAMNOPYRANOSYL-.BETA.-D-GLUCOPYRANOSIDE
    • Not Applicable
    • s2350', "3,3',4',5,5',7-Hexahydroxyflavone (6-O-alpha-L-rhamnosyl-beta-D-glucoside)", 'AKOS015895432
    • Quercetin-3beta-rutinoside
    • Rutin1541', "3,3',4',5,7-Pentahydroxyflavone 3-rutinoside", 'RUTIN [VANDF]
    • R0035
    • AB00374708-09
    • NCGC00160628-01
    • NSC9220', "3-RHAMNOGLUCOSIDE OF 5,7,3',4'-TETRAHYDROXYFLAVONOL", '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-4-oxo-4H-chromen-3-yl 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-mannopyranoside
    • A8241DA0-6EC6-48BA-BD10-3F7BD61D42CE
    • SCHEMBL23243
    • RUTIN [USP-RS]
    • Rutoside [INN]
    • Violaquercitrin
    • Myrticolorin
    • 3-[[6-O-(6-Deoxy-alpha-l-mannopyranosyl)-beta-d-glucopyranosyl]oxy]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
    • Venoruton
    • Glucopyranoside, quercetin-3 6-O-(6-deoxy-alpha-L-mannopyranosyl)-, beta-D-
    • Quercitin 3-rutinoside
    • Quercetin 3-O-beta-delta-rutinoside
    • Quercetin, 3-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranoside)
    • RUTIN [MI]
    • MEGxp0_000068
    • tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one
    • Rutinoside, quercetin-3, beta-
    • Rutosido
    • 4H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-
    • Oxyritin
    • Rutin (Rutoside)
    • 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
    • Quercetin rhamnoglucosine
    • Rutabion
    • MLS001424098
    • Q407857
    • BDBM50217942
    • Tanrutin
    • 3-((6-O-(6-Deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranosyl)oxy)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-4-one
    • NSC 9220
    • CHEBI:28527
    • Bioflavonoid
    • Rutinoside, 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-3-yl
    • BIDD:ER0377
    • Quercetin, 3-(6-0-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside)
    • NINDS_000644', "3,3',4',5,7-PENTAHYDROXYFLAVONE-3-RHAMNOGLUCOSIDE", 'HMS2051B06', "3'4'5,7-tetOH-Flavone-3-rut", 'HY-N0148
    • 3-Rhamnoglucosylquercetin
    • 4H-1-Benzopyran-4-one,3-[[6-O-(6-deoxy-a-L-mannopyranosyl)-b-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-
    • Rutin
    • RUTIN [DSC]
    • MFCD00006830
    • methyltetrahydro-2H-pyran-2-yloxy)methyl)
    • BRD-K20482099-001-09-4
    • beta-Quercetin-3-rutinoside
    • Rutin (Standard)
    • Tox21_202602
    • 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
    • Q-201691
    • Rutosido (INN-Spanish)', "Flavone, 3,3',4',5,7-pentahydroxy-, 3-(O-rhamnosylglucoside)", 'RUTIN (USP-RS)
    • Sophorin
    • C.I. 75730

Attributes

  • Canonical SMILES

    C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O

  • InChI

    InChI=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

  • Molecule Class: Flavonoids
  • TPSA: 269.42999999999995
  • #RotBonds: 6
  • MW: 610.5210000000006
  • HBD: 10
  • HBA: 16
  • logP: -1.6871000000000005
  • Chemical Formula: C27H30O16


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862
    T. heyneana India 2563820 -

External Databases


References

  • HPLC analysis and antimicrobial, antimycobacterial and antiviral activities of Tabernaemontana catharinensis A. DC Journal of Applied Biomedicine, 2015 (DOI).
  • Simultaneous Extraction Optimization and Analysis of Flavonoids from the Flowers of Tabernaemontana heyneana by High Performance Liquid Chromatography Coupled to Diode Array Detector and Electron Spray Ionization/Mass Spectrometry. ISRN Biotechnol, 2013 (PMID 25969771).

Compound-Protein Relationships


Compound Activities

    • Antioxidant
    • Antihypercholesterolemic
    • Antimicrobial
    • Antiherpetic
    • Antiviral
    • Cytotoxicity
    • Antithrombogenic
    • Antiherpes
    • Antimycobacterial

Predicted NMR Spectral Data


Predicted MS Fragmentation Patternn


Predicted ADMET Properties

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -6.6
    Human Oral Bioavailability 20% Non-Bioavailable
    Human Intestinal Absorption Non-Absorbed
    Madin-Darby Canine Kidney -5.53
    Human Oral Bioavailability 50% Non-Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability 8.83
    Distribution Blood-Brain Barrier (Central Nervous System) -4.61
    Blood-Brain Barrier Non-Penetrable
    Fraction Unbound (Human) 0.74
    Plasma Protein Binding 67.78
    Steady State Volume of Distribution 0.77
    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 13.3
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Toxic
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -3.83
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 0.96
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.86
    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 -13209.73
    Rat (Acute) 2.21
    Rat (Chronic Oral) 4.46
    Fathead Minnow 29.12
    Respiratory Disease Safe
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 517.06
    Hydration Free Energy -3.11
    Log(D) at pH=7.4 -0.94
    Log(P) -0.32
    Log S -4.48
    Log(Vapor Pressure) -14.6
    Melting Point 204.97
    pKa Acid 3.48
    pKa Basic 8.22