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Record Information
Version1.0
Created at2020-09-21 21:51:00 UTC
Updated at2021-08-10 02:55:15 UTC
NP-MRD IDNP0001561
Secondary Accession NumbersNone
Natural Product Identification
Common NameOphioglonol 4'-O-beta-D-glucopyranoside
DescriptionOphioglonol 4'-O-beta-D-glucopyranoside belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Ophioglonol 4'-O-beta-D-glucopyranoside 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 1975 (PMID: 1234567). Based on a literature review a small amount of articles have been published on ophioglonol 4'-O-beta-D-glucopyranoside (PMID: 21401115) (PMID: 15787440) (PMID: 30132647).
Structure
Data?1628564114
Synonyms
ValueSource
Ophioglonol 4'-O-b-D-glucopyranosideGenerator
Ophioglonol 4'-O-β-D-glucopyranosideGenerator
Chemical FormulaC22H22O12
Average Mass478.4060 Da
Monoisotopic Mass478.11113 Da
IUPAC Name5,7-dihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(hydroxymethyl)-4H-chromen-4-one
Traditional Name5,7-dihydroxy-2-(3-hydroxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(hydroxymethyl)chromen-4-one
CAS Registry NumberNot Available
SMILES
[H]OC1=C([H])C(O[H])=C2C(=O)C(=C(OC2=C1[H])C1=C([H])C(O[H])=C(O[C@]2([H])O[C@]([H])(C([H])([H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]2([H])O[H])C([H])=C1[H])C([H])([H])O[H]
InChI Identifier
InChI=1S/C22H22O12/c23-6-10-17(28)16-12(27)4-9(25)5-14(16)32-21(10)8-1-2-13(11(26)3-8)33-22-20(31)19(30)18(29)15(7-24)34-22/h1-5,15,18-20,22-27,29-31H,6-7H2/t15-,18-,19+,20-,22-/m1/s1
InChI KeyXTPXAOSAGWJNDB-VQIXPAPJSA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500MHz, H2O, simulated)Mb12021-03-23View Spectrum
1D NMR1H NMR Spectrum (1D, 500Mz, DMSO, simulated)Rgf8b2020-09-21View Spectrum
Species
Species of Origin
Species NameSourceReference
Ophioglossum petiolatumKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid O-glycosides
Alternative Parents
Substituents
  • Flavonoid-4p-o-glycoside
  • Flavonoid o-glycoside
  • 3'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Phenoxy compound
  • Phenol ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Oxane
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Acetal
  • Polyol
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organic oxygen compound
  • 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
logP10(0.14) g/LALOGPS
logP10(-0.75) g/LChemAxon
logS10(-2.6) g/LALOGPS
pKa (Strongest Acidic)6.53ChemAxon
pKa (Strongest Basic)-2.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area206.6 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.17 m³·mol⁻¹ChemAxon
Polarizability46.12 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00042808
Chemspider ID26348377
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID67935
Good Scents IDNot Available
References
General References
  1. Rauramo L, Lagerspetz K, Engblom P, Punnonen R: The effect of castration and peroral estrogen therapy on some psychological functions. Front Horm Res. 1975;3:94-104. doi: 10.1159/000398269. [PubMed:1234567 ]
  2. Wan CX, Zhang PH, Luo JG, Kong LY: Homoflavonoid glucosides from Ophioglossum pedunculosum and their anti-HBV activity. J Nat Prod. 2011 Apr 25;74(4):683-9. doi: 10.1021/np100745z. Epub 2011 Mar 14. [PubMed:21401115 ]
  3. Lin YL, Shen CC, Huang YJ, Chang YY: Homoflavonoids from Ophioglossum petiolatum. J Nat Prod. 2005 Mar;68(3):381-4. doi: 10.1021/np0401819. [PubMed:15787440 ]
  4. Hu WC, Zhou ZB, Wan CX: [Study on Flavonoids of Ophioglossum thermal]. Zhong Yao Cai. 2016 May;39(5):1035-7. [PubMed:30132647 ]