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Record Information
Version2.0
Created at2022-09-12 04:33:47 UTC
Updated at2022-09-12 04:33:47 UTC
NP-MRD IDNP0324466
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-hydroxy-5-methoxy-3-{[(1r,2s)-1,2,5,5-tetramethyl-2,3,6,7,8,8a-hexahydronaphthalen-1-yl]methyl}cyclohexa-2,5-diene-1,4-dione
DescriptionMamanuthaquinone belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. 2-hydroxy-5-methoxy-3-{[(1r,2s)-1,2,5,5-tetramethyl-2,3,6,7,8,8a-hexahydronaphthalen-1-yl]methyl}cyclohexa-2,5-diene-1,4-dione was first documented in 1999 (PMID: 10514323). Based on a literature review very few articles have been published on Mamanuthaquinone.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC22H30O4
Average Mass358.4780 Da
Monoisotopic Mass358.21441 Da
IUPAC Name2-hydroxy-5-methoxy-3-{[(1R,2S)-1,2,5,5-tetramethyl-1,2,3,5,6,7,8,8a-octahydronaphthalen-1-yl]methyl}cyclohexa-2,5-diene-1,4-dione
Traditional Name2-hydroxy-5-methoxy-3-{[(1R,2S)-1,2,5,5-tetramethyl-2,3,6,7,8,8a-hexahydronaphthalen-1-yl]methyl}cyclohexa-2,5-diene-1,4-dione
CAS Registry NumberNot Available
SMILES
COC1=CC(=O)C(O)=C(C[C@]2(C)[C@@H](C)CC=C3C2CCCC3(C)C)C1=O
InChI Identifier
InChI=1S/C22H30O4/c1-13-8-9-15-16(7-6-10-21(15,2)3)22(13,4)12-14-19(24)17(23)11-18(26-5)20(14)25/h9,11,13,16,24H,6-8,10,12H2,1-5H3/t13-,16?,22+/m0/s1
InChI KeyYXMANDRSLJYXOW-DWJYJAETSA-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 prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassQuinone and hydroquinone lipids
Direct ParentPrenylquinones
Alternative Parents
Substituents
  • Prenylbenzoquinone
  • Quinone
  • P-benzoquinone
  • Vinylogous ester
  • Vinylogous acid
  • Cyclic ketone
  • Ketone
  • Enol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic 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
logP4.31ChemAxon
pKa (Strongest Acidic)5.87ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area63.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity105.22 m³·mol⁻¹ChemAxon
Polarizability39.82 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 IDNot Available
Chemspider ID10143344
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11969939
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. De Rosa S, Crispino A, De Giulio A, Iodice C, Amodeo P, Tancredi T: A new cacospongionolide derivative from the sponge Fasciospongia cavernosa. J Nat Prod. 1999 Sep;62(9):1316-8. doi: 10.1021/np990125l. [PubMed:10514323 ]
  2. LOTUS database [Link]