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Record Information
Version1.0
Created at2021-06-22 17:19:02 UTC
Updated at2021-06-22 17:19:02 UTC
NP-MRD IDNP0043816
Secondary Accession NumbersNone
Natural Product Identification
Common Name5-epi-Nakijiquinone T
Description3-{[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]methyl}-2-hydroxy-5-{[2-(1H-indol-3-yl)ethyl]amino}cyclohexa-2,5-diene-1,4-dione 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. 5-epi-Nakijiquinone T is found in Dactylospongia metachromia. It was first documented in 2014 (PMID: 24479418). Based on a literature review very few articles have been published on 3-{[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]methyl}-2-hydroxy-5-{[2-(1H-indol-3-yl)ethyl]amino}cyclohexa-2,5-diene-1,4-dione.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC31H38N2O3
Average Mass486.6560 Da
Monoisotopic Mass486.28824 Da
IUPAC Name3-{[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl]methyl}-2-hydroxy-5-{[2-(1H-indol-3-yl)ethyl]amino}cyclohexa-2,5-diene-1,4-dione
Traditional Name3-{[(1R,2S,4aR,8aS)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]methyl}-2-hydroxy-5-{[2-(1H-indol-3-yl)ethyl]amino}cyclohexa-2,5-diene-1,4-dione
CAS Registry NumberNot Available
SMILES
[H][C@@]12CCC=C(C)[C@]1(C)CC[C@H](C)[C@@]2(C)CC1=C(O)C(=O)C=C(NCCC2=CNC3=C2C=CC=C3)C1=O
InChI Identifier
InChI=1S/C31H38N2O3/c1-19-8-7-11-27-30(19,3)14-12-20(2)31(27,4)17-23-28(35)25(16-26(34)29(23)36)32-15-13-21-18-33-24-10-6-5-9-22(21)24/h5-6,8-10,16,18,20,27,32-33,36H,7,11-15,17H2,1-4H3/t20-,27+,30-,31+/m0/s1
InChI KeyKMDGCQCDKFMKAD-WORHRAFRSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Dactylospongia metachromiaLinigton's dataset
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
  • Tryptamine
  • 3-alkylindole
  • Indole
  • Indole or derivatives
  • P-benzoquinone
  • Quinone
  • Aralkylamine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Vinylogous amide
  • Vinylogous acid
  • Cyclic ketone
  • Ketone
  • Secondary aliphatic amine
  • Azacycle
  • Organoheterocyclic compound
  • Enamine
  • Enol
  • Secondary amine
  • Carbonyl group
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Amine
  • 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
logP5.42ALOGPS
logP6.1ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)6.2ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area82.19 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity147.35 m³·mol⁻¹ChemAxon
Polarizability56.17 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID31130046
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Daletos G, de Voogd NJ, Muller WE, Wray V, Lin W, Feger D, Kubbutat M, Aly AH, Proksch P: Cytotoxic and protein kinase inhibiting nakijiquinones and nakijiquinols from the sponge Dactylospongia metachromia. J Nat Prod. 2014 Feb 28;77(2):218-26. doi: 10.1021/np400633m. Epub 2014 Jan 30. [PubMed:24479418 ]