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Record Information
Version2.0
Created at2021-06-20 21:26:55 UTC
Updated at2021-06-30 00:11:53 UTC
NP-MRD IDNP0038871
Secondary Accession NumbersNone
Natural Product Identification
Common Namewalsuronoid B
Provided ByJEOL DatabaseJEOL Logo
DescriptionWalsuronoid B belongs to the class of organic compounds known as 17-furanylsteroids and derivatives. These are steroidal compounds having a furanyl group linked to the steroid backbone at the C17 position. walsuronoid B is found in Walsura robusta. walsuronoid B was first documented in 2017 (PMID: 28673807). Based on a literature review very few articles have been published on Walsuronoid B (PMID: 28129886).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC26H30O6
Average Mass438.5200 Da
Monoisotopic Mass438.20424 Da
IUPAC Name(1R,2R,10R,11R,12R,17S)-14-(furan-3-yl)-8,12,17-trihydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7,14-triene-5,9-dione
Traditional Name(1R,2R,10R,11R,12R,17S)-14-(furan-3-yl)-8,12,17-trihydroxy-2,6,6,10,11-pentamethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,7,14-triene-5,9-dione
CAS Registry NumberNot Available
SMILES
[H]OC1=C2C(C(=O)C([H])=C([H])[C@]2(C([H])([H])[H])[C@@]2([H])[C@@]([H])(O[H])C([H])([H])C3=C(C4=C([H])OC([H])=C4[H])C([H])([H])[C@@]([H])(O[H])[C@@]3(C([H])([H])[H])[C@@]2(C1=O)C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H]
InChI Identifier
InChI=1S/C26H30O6/c1-23(2)17(28)6-8-24(3)20-16(27)11-15-14(13-7-9-32-12-13)10-18(29)25(15,4)26(20,5)22(31)19(30)21(23)24/h6-9,12,16,18,20,27,29-30H,10-11H2,1-5H3/t16-,18+,20+,24+,25-,26-/m0/s1
InChI KeyXXFWAJSCCSMNPP-FTGJQZKBSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, CDCl3, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Walsura robustaJEOL database
    • Yin, S., et al, Org. Lett. 9, 2353 (2007)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 17-furanylsteroids and derivatives. These are steroidal compounds having a furanyl group linked to the steroid backbone at the C17 position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub Class17-furanylsteroids and derivatives
Direct Parent17-furanylsteroids and derivatives
Alternative Parents
Substituents
  • 17-furanylsteroid skeleton
  • 3-oxo-delta-1-steroid
  • 3-oxosteroid
  • 14-alpha-methylsteroid
  • 6-hydroxysteroid
  • 15-hydroxysteroid
  • Hydroxysteroid
  • Oxosteroid
  • 11-beta-hydroxysteroid
  • 7-oxosteroid
  • 11-hydroxysteroid
  • Delta-1-steroid
  • Cyclohexenone
  • Cyclic alcohol
  • Furan
  • Heteroaromatic compound
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Organoheterocyclic compound
  • Enol
  • Polyol
  • Oxacycle
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Organic oxide
  • 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
logP2.71ALOGPS
logP2.52ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.41ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area107.97 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity121.07 m³·mol⁻¹ChemAxon
Polarizability46.67 ųChemAxon
Number of Rings5ChemAxon
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 IDNot Available
Chemspider ID17628002
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16724460
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Geng YD, Zhang C, Lei JL, Yu P, Xia YZ, Zhang H, Yang L, Kong LY: Walsuronoid B induces mitochondrial and lysosomal dysfunction leading to apoptotic rather than autophagic cell death via ROS/p53 signaling pathways in liver cancer. Biochem Pharmacol. 2017 Oct 15;142:71-86. doi: 10.1016/j.bcp.2017.06.134. Epub 2017 Jul 1. [PubMed:28673807 ]
  2. Zhang Y, An FL, Huang SS, Yang L, Gu YC, Luo J, Kong LY: Diverse tritepenoids from the fruits of Walsura robusta and their reversal of multidrug resistance phenotype in human breast cancer cells. Phytochemistry. 2017 Apr;136:108-118. doi: 10.1016/j.phytochem.2017.01.008. Epub 2017 Jan 24. [PubMed:28129886 ]
  3. Yin, S., et al. (2007). Yin, S., et al, Org. Lett. 9, 2353 (2007). Org. Lett..