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Record Information
Version1.0
Created at2023-09-20 16:01:16 UTC
Updated at2024-04-19 09:53:13 UTC
NP-MRD IDNP0331835
Secondary Accession NumbersNone
Natural Product Identification
Common NameSilibinin
DescriptionSilibinin is also known as silybin or legalon. Silibinin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. It was first documented in 2021 (PMID: 34399200). Based on a literature review a significant number of articles have been published on Silibinin (PMID: 34353693) (PMID: 34360650) (PMID: 34348081) (PMID: 34344191) (PMID: 34285784) (PMID: 34258250).
Structure
Thumb
Synonyms
ValueSource
FlavobinChEBI
KarsilChEBI
SilibininaChEBI
SilibinineChEBI
SilibininumChEBI
SilybinChEBI
SilymarinChEBI
Silymarin IKegg
LegalonKegg
2,3 DehydrosilybinMeSH
2,3-DehydrosilybinMeSH
Alepa forteMeSH
Alepa-forteMeSH
ArdeyhepanMeSH
CefasilymarinMeSH
Hepa merz silMeSH
Hepa logesMeSH
Hepa-merz silMeSH
HepaBeschMeSH
Hepar pascMeSH
Hepar-pascMeSH
HeparsyxMeSH
HeplantMeSH
LagosaMeSH
Silibinin aMeSH
Silibinin bMeSH
DurasilymarinMeSH
Hepa-logesMeSH
Legalon forteMeSH
SilibinMeSH
Silybin aMeSH
Silybin bMeSH
SilybininMeSH
SilibininMeSH
HepatosMeSH
Chemical FormulaC25H22O10
Average Mass482.4410 Da
Monoisotopic Mass482.12130 Da
IUPAC Name(2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Namesilibinin
CAS Registry NumberNot Available
SMILES
[H]OC1=C([H])C(O[H])=C2C(O[C@]([H])(C3=C([H])C([H])=C4O[C@]([H])(C([H])([H])O[H])[C@]([H])(OC4=C3[H])C3=C([H])C([H])=C(O[H])C(OC([H])([H])[H])=C3[H])[C@@]([H])(O[H])C2=O)=C1[H]
InChI Identifier
InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1
InChI KeySEBFKMXJBCUCAI-HKTJVKLFSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-20View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-20View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-20View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)bgnzk@missouri.eduMU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2023-09-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFlavonolignans
Sub ClassNot Available
Direct ParentFlavonolignans
Alternative Parents
Substituents
  • Flavonolignan
  • Hydroxyflavonoid
  • 3-hydroxyflavonoid
  • Flavanonol
  • Flavanone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • Flavan
  • Phenylbenzodioxane
  • 2-phenylbenzo-1,4-dioxane
  • Chromone
  • 1-benzopyran
  • Methoxyphenol
  • Benzopyran
  • Chromane
  • Benzodioxane
  • Benzo-1,4-dioxane
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Para-dioxin
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.35ALOGPS
logP2.63ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)7.75ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity120.29 m³·mol⁻¹ChemAxon
Polarizability48.64 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDDB09298
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00001003
Chemspider ID29263
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSilibinin
METLIN IDNot Available
PubChem Compound31553
PDB IDNot Available
ChEBI ID9144
Good Scents IDrw1108841
References
General References
  1. Dhami-Shah H, Vaidya R, Talwadekar M, Shaw E, Udipi S, Kolthur-Seetharam U, Vaidya ADB: Intervention by picroside II on FFAs induced lipid accumulation and lipotoxicity in HepG2 cells. J Ayurveda Integr Med. 2021 Jul-Sep;12(3):465-473. doi: 10.1016/j.jaim.2021.04.007. Epub 2021 Aug 2. [PubMed:34353693 ]
  2. Fallah M, Davoodvandi A, Nikmanzar S, Aghili S, Mirazimi SMA, Aschner M, Rashidian A, Hamblin MR, Chamanara M, Naghsh N, Mirzaei H: Silymarin (milk thistle extract) as a therapeutic agent in gastrointestinal cancer. Biomed Pharmacother. 2021 Oct;142:112024. doi: 10.1016/j.biopha.2021.112024. Epub 2021 Aug 13. [PubMed:34399200 ]
  3. Kren V: Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners. Int J Mol Sci. 2021 Jul 23;22(15):7885. doi: 10.3390/ijms22157885. [PubMed:34360650 ]
  4. Mukherjee S, Sharma D, Sharma AK, Jaiswal S, Sharma N, Borah S, Kaur G: Flavan-based phytoconstituents inhibit Mpro, a SARS-COV-2 molecular target, in silico. J Biomol Struct Dyn. 2022;40(22):11545-11559. doi: 10.1080/07391102.2021.1960196. Epub 2021 Aug 4. [PubMed:34348081 ]
  5. Schenk-Jager K, Gessler M, Weiler S: [CME: Mushroom Poisoning in the Family Practice]. Praxis (Bern 1994). 2021 Aug;110(10):543-553. doi: 10.1024/1661-8157/a003715. [PubMed:34344191 ]
  6. Yan B, Zhang C: Liver Protection Mechanism and Absorption Promotion Technology of Silybin Based on Intelligent Medical Analysis. J Healthc Eng. 2021 Jul 3;2021:9968016. doi: 10.1155/2021/9968016. eCollection 2021. [PubMed:34285784 ]
  7. Cho K, Lee HG, Piao JY, Kim SJ, Na HK, Surh YJ: Protective Effects of Silibinin on Helicobacter pylori-induced Gastritis: NF-kappaB and STAT3 as Potential Targets. J Cancer Prev. 2021 Jun 30;26(2):118-127. doi: 10.15430/JCP.2021.26.2.118. [PubMed:34258250 ]
  8. Ali SA, Saifi MA, Godugu C, Talla V: Silibinin alleviates silica-induced pulmonary fibrosis: Potential role in modulating inflammation and epithelial-mesenchymal transition. Phytother Res. 2021 Sep;35(9):5290-5304. doi: 10.1002/ptr.7210. Epub 2021 Jul 12. [PubMed:34250649 ]
  9. Vidimce J, Pennell EN, Foo M, Shiels RG, Shibeeb S, Watson M, Bulmer AC: Effect of Silymarin Treatment on Circulating Bilirubin and Cardiovascular Disease Risk Factors in Healthy Men: A Single-Blind, Randomized Crossover Trial. Clin Pharmacol Drug Dev. 2021 Oct;10(10):1156-1165. doi: 10.1002/cpdd.962. Epub 2021 Jul 9. [PubMed:34242497 ]
  10. Prabu SM, Muthumani M: Retraction Note to: Silibinin ameliorates arsenic induced nephrotoxicity by abrogation of oxidative stress, inflammation and apoptosis in rats. Mol Biol Rep. 2021 Jun;48(6):5377. doi: 10.1007/s11033-021-06475-x. [PubMed:34235619 ]
  11. Mohammadi H, Manouchehri H, Changizi R, Bootorabi F, Khorramizadeh MR: Correction to: Concurrent metformin and silibinin therapy in diabetes: assessments in zebrafish (Danio rerio) animal model. J Diabetes Metab Disord. 2020 Dec 7;20(1):1099. doi: 10.1007/s40200-020-00698-8. eCollection 2021 Jun. [PubMed:34222101 ]
  12. Zarpou S, Mosavi H, Bagheri A, Malekzadeh Shafaroudi M, Khonakdar-Tarsi A: NF-kappaB and NLRP3 gene expression changes during warm hepatic ischemia-reperfusion in rats with and without silibinin. Gastroenterol Hepatol Bed Bench. 2021 Summer;14(3):267-275. [PubMed:34221267 ]
  13. Rugamba A, Kang DY, Sp N, Jo ES, Lee JM, Bae SW, Jang KJ: Silibinin Regulates Tumor Progression and Tumorsphere Formation by Suppressing PD-L1 Expression in Non-Small Cell Lung Cancer (NSCLC) Cells. Cells. 2021 Jun 29;10(7):1632. doi: 10.3390/cells10071632. [PubMed:34209829 ]
  14. Verdura S, Cuyas E, Ruiz-Torres V, Micol V, Joven J, Bosch-Barrera J, Menendez JA: Lung Cancer Management with Silibinin: A Historical and Translational Perspective. Pharmaceuticals (Basel). 2021 Jun 11;14(6):559. doi: 10.3390/ph14060559. [PubMed:34208282 ]
  15. Liu X, Liu W, Wang C, Chen Y, Liu P, Hayashi T, Mizuno K, Hattori S, Fujisaki H, Ikejima T: Silibinin attenuates motor dysfunction in a mouse model of Parkinson's disease by suppression of oxidative stress and neuroinflammation along with promotion of mitophagy. Physiol Behav. 2021 Oct 1;239:113510. doi: 10.1016/j.physbeh.2021.113510. Epub 2021 Jun 25. [PubMed:34181930 ]