Np mrd loader

Record Information
Version2.0
Created at2022-03-17 20:43:03 UTC
Updated at2022-03-17 20:43:03 UTC
NP-MRD IDNP0047613
Secondary Accession NumbersNone
Natural Product Identification
Common NameSilandrin
DescriptionSilandrin 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. Silandrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Silandrin has been detected, but not quantified in, coffee and coffee products and green vegetables. Silandrin is found in Silybum marianum . This could make silandrin a potential biomarker for the consumption of these foods.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC25H22O9
Average Mass466.4368 Da
Monoisotopic Mass466.12638 Da
IUPAC Name5,7-dihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name5,7-dihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-1-benzopyran-4-one
CAS Registry Number70815-32-6
SMILES
COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=C(C=C2)C1CC(=O)C2=C(O1)C=C(O)C=C2O
InChI Identifier
InChI=1S/C25H22O9/c1-31-20-7-13(2-4-15(20)28)25-23(11-26)33-21-6-12(3-5-18(21)34-25)19-10-17(30)24-16(29)8-14(27)9-22(24)32-19/h2-9,19,23,25-29H,10-11H2,1H3
InChI KeyCRPGUMMYQABYES-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Coffea arabica L.FooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephoraFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Silybum marianumPlant
Chemical Taxonomy
Description 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
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Flavan
  • 2-phenylbenzo-1,4-dioxane
  • Phenylbenzodioxane
  • Chromone
  • Methoxyphenol
  • Benzo-1,4-dioxane
  • Benzodioxane
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Aryl ketone
  • Aryl alkyl ketone
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Para-dioxin
  • Vinylogous acid
  • Ketone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Alcohol
  • Primary alcohol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP3.08ALOGPS
logP3.34ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)7.92ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area134.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity118.96 m³·mol⁻¹ChemAxon
Polarizability47.8 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033325
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011352
KNApSAcK IDC00001002
Chemspider ID3679221
KEGG Compound IDC08600
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound4481258
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available