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Record Information
Version2.0
Created at2022-09-12 03:20:17 UTC
Updated at2022-09-12 03:20:18 UTC
NP-MRD IDNP0323723
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,2r,4ar,5s,7e,8ar)-5-hydroxy-7-(1-hydroxypropan-2-ylidene)-1,8a-dimethyl-6-oxo-hexahydro-1h-naphthalen-2-yl (2e,4e,6e)-5-methyldodeca-2,4,6-trienoate
Description(1R,2R,4aR,5S,7E,8aR)-5-hydroxy-7-(1-hydroxypropan-2-ylidene)-1,8a-dimethyl-6-oxo-decahydronaphthalen-2-yl (2E,4E,6E)-5-methyldodeca-2,4,6-trienoate belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review very few articles have been published on (1R,2R,4aR,5S,7E,8aR)-5-hydroxy-7-(1-hydroxypropan-2-ylidene)-1,8a-dimethyl-6-oxo-decahydronaphthalen-2-yl (2E,4E,6E)-5-methyldodeca-2,4,6-trienoate.
Structure
Thumb
Synonyms
ValueSource
(1R,2R,4AR,5S,7E,8ar)-5-hydroxy-7-(1-hydroxypropan-2-ylidene)-1,8a-dimethyl-6-oxo-decahydronaphthalen-2-yl (2E,4E,6E)-5-methyldodeca-2,4,6-trienoic acidGenerator
Chemical FormulaC28H42O5
Average Mass458.6390 Da
Monoisotopic Mass458.30322 Da
IUPAC Name(1R,2R,4aR,5S,7E,8aR)-5-hydroxy-7-(1-hydroxypropan-2-ylidene)-1,8a-dimethyl-6-oxo-decahydronaphthalen-2-yl (2E,4E,6E)-5-methyldodeca-2,4,6-trienoate
Traditional Name(1R,2R,4aR,5S,7E,8aR)-5-hydroxy-7-(1-hydroxypropan-2-ylidene)-1,8a-dimethyl-6-oxo-hexahydro-1H-naphthalen-2-yl (2E,4E,6E)-5-methyldodeca-2,4,6-trienoate
CAS Registry NumberNot Available
SMILES
CCCCC\C=C\C(\C)=C\C=C\C(=O)O[C@@H]1CC[C@H]2[C@H](O)C(=O)\C(C[C@]2(C)[C@H]1C)=C(/C)CO
InChI Identifier
InChI=1S/C28H42O5/c1-6-7-8-9-10-12-19(2)13-11-14-25(30)33-24-16-15-23-27(32)26(31)22(20(3)18-29)17-28(23,5)21(24)4/h10-14,21,23-24,27,29,32H,6-9,15-18H2,1-5H3/b12-10+,14-11+,19-13+,22-20+/t21-,23-,24+,27-,28+/m0/s1
InChI KeyHVMGZGISBALRNN-XPGLAVBJSA-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 eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentEremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids
Alternative Parents
Substituents
  • Eremophilane sesquiterpenoid
  • Fatty acid ester
  • Fatty acyl
  • Cyclic alcohol
  • Enoate ester
  • Alpha,beta-unsaturated carboxylic ester
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Primary alcohol
  • Organooxygen compound
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • 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
logP5.67ChemAxon
pKa (Strongest Acidic)13.13ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity135.68 m³·mol⁻¹ChemAxon
Polarizability54.05 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
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 IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound162955830
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. LOTUS database [Link]