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Record Information
Version2.0
Created at2022-06-29 19:50:51 UTC
Updated at2022-06-29 19:50:51 UTC
NP-MRD IDNP0139358
Secondary Accession NumbersNone
Natural Product Identification
Common NameOphiopogonanone B
DescriptionOphiopogonanone B belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position. Ophiopogonanone B was first documented in 2003 (PMID: 14519939). Based on a literature review a small amount of articles have been published on Ophiopogonanone B (PMID: 33212179) (PMID: 29961188) (PMID: 21163470).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC18H18O5
Average Mass314.3370 Da
Monoisotopic Mass314.11542 Da
IUPAC Name(3R)-5,7-dihydroxy-3-[(4-methoxyphenyl)methyl]-6-methyl-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name(3R)-5,7-dihydroxy-3-[(4-methoxyphenyl)methyl]-6-methyl-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
COC1=CC=C(C[C@@H]2COC3=C(C2=O)C(O)=C(C)C(O)=C3)C=C1
InChI Identifier
InChI=1S/C18H18O5/c1-10-14(19)8-15-16(17(10)20)18(21)12(9-23-15)7-11-3-5-13(22-2)6-4-11/h3-6,8,12,19-20H,7,9H2,1-2H3/t12-/m1/s1
InChI KeyOOHKTNVQRTUZRS-GFCCVEGCSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as homoisoflavanones. These are homoisoflavonoids with a structure based on the chromanone system. Chromanone is a bicyclic compound consisting of a 3,4-dihydro-1-benzopyran, which bears a ketone group at the 4-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassHomoisoflavonoids
Sub ClassHomoisoflavans
Direct ParentHomoisoflavanones
Alternative Parents
Substituents
  • Homoisoflavanone
  • Chromone
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Phenoxy compound
  • Phenol ether
  • Aryl ketone
  • Aryl alkyl ketone
  • Methoxybenzene
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Ketone
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • 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
logP3.15ALOGPS
logP3.83ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)8.24ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity85.8 m³·mol⁻¹ChemAxon
Polarizability32.45 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00037501
Chemspider ID107562096
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53468064
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Yu ZW, Lou GD, Ge LL: Rapid identification of cytochrome P450 inductive constituents of Shenmai injection by combined pregnane X receptor reporter gene assay and LC-TOF-MS analysis. J Ethnopharmacol. 2021 Mar 25;268:113588. doi: 10.1016/j.jep.2020.113588. Epub 2020 Nov 16. [PubMed:33212179 ]
  2. Kitahiro Y, Koike A, Sonoki A, Muto M, Ozaki K, Shibano M: Anti-inflammatory activities of Ophiopogonis Radix on hydrogen peroxide-induced cellular senescence of normal human dermal fibroblasts. J Nat Med. 2018 Sep;72(4):905-914. doi: 10.1007/s11418-018-1223-9. Epub 2018 Jun 30. [PubMed:29961188 ]
  3. Wang KW, Zhang H, Shen LQ, Wang W: Novel steroidal saponins from Liriope graminifolia (Linn.) Baker with anti-tumor activities. Carbohydr Res. 2011 Feb 1;346(2):253-8. doi: 10.1016/j.carres.2010.11.015. Epub 2010 Nov 21. [PubMed:21163470 ]
  4. Hasebe Y, Egawa K, Yamazaki Y, Kunimoto S, Hirai Y, Ida Y, Nose K: Specific inhibition of hypoxia-inducible factor (HIF)-1 alpha activation and of vascular endothelial growth factor (VEGF) production by flavonoids. Biol Pharm Bull. 2003 Oct;26(10):1379-83. doi: 10.1248/bpb.26.1379. [PubMed:14519939 ]