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Record Information
Version1.0
Created at2021-06-21 00:15:42 UTC
Updated at2021-06-30 00:17:51 UTC
NP-MRD IDNP0042649
Secondary Accession NumbersNone
Natural Product Identification
Common Name(4R,5S,10S)-5-hydroxy-11,12,13-trinoreudesm-6-en-8-one
Provided ByJEOL DatabaseJEOL Logo
Description(4AS)-4aalpha-Hydroxy-5alpha,8aalpha-dimethyl-4a,5,6,7,8,8a-hexahydronaphthalene-2(1H)-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (4R,5S,10S)-5-hydroxy-11,12,13-trinoreudesm-6-en-8-one is found in Inula racemosa. It was first documented in 2006 (PMID: 29999960). Based on a literature review a small amount of articles have been published on (4aS)-4aalpha-Hydroxy-5alpha,8aalpha-dimethyl-4a,5,6,7,8,8a-hexahydronaphthalene-2(1H)-one (PMID: 30468024) (PMID: 29999636) (PMID: 29504554) (PMID: 21589050).
Structure
Thumb
Synonyms
ValueSource
(4AS)-4aalpha-hydroxy-5a,8aalpha-dimethyl-4a,5,6,7,8,8a-hexahydronaphthalene-2(1H)-oneGenerator
(4AS)-4aalpha-hydroxy-5α,8aalpha-dimethyl-4a,5,6,7,8,8a-hexahydronaphthalene-2(1H)-oneGenerator
Chemical FormulaC12H18O2
Average Mass194.2740 Da
Monoisotopic Mass194.13068 Da
IUPAC Name(4aS,5R,8aS)-4a-hydroxy-5,8a-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-2-one
Traditional Name(4aS,5R,8aS)-4a-hydroxy-5,8a-dimethyl-5,6,7,8-tetrahydro-1H-naphthalen-2-one
CAS Registry NumberNot Available
SMILES
[H]O[C@@]12C([H])=C([H])C(=O)C([H])([H])[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2([H])C([H])([H])[H]
InChI Identifier
InChI=1S/C12H18O2/c1-9-4-3-6-11(2)8-10(13)5-7-12(9,11)14/h5,7,9,14H,3-4,6,8H2,1-2H3/t9-,11+,12-/m1/s1
InChI KeyRTYOTMKUFIVWRN-ADEWGFFLSA-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
Inula racemosaJEOL database
    • Ma, Y.-Y., et al, Phytochem. Lett. 6, 645 (2013)
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Tertiary alcohol
  • Cyclic alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • 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
logP1.72ALOGPS
logP2.15ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)13.76ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.16 m³·mol⁻¹ChemAxon
Polarizability21.56 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
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 Compound102103822
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Liu LF, Yao MJ, Li MY, Wu XZ, Yuan CS: Iridoid Derivatives with Cytotoxic Activity from Pedicularis uliginosa Bunge. Chem Biodivers. 2019 Feb;16(2):e1800524. doi: 10.1002/cbdv.201800524. Epub 2019 Jan 23. [PubMed:30468024 ]
  2. Authors unspecified: Docetaxel. 2006. [PubMed:29999960 ]
  3. Authors unspecified: Paclitaxel. 2006. [PubMed:29999636 ]
  4. Goncalves KO, Ribeiro L, Oliveira CMA, Carvalho JF, Martins FT: New solvates of the drug naltrexone: protonation, conformation and interplay of synthons. Acta Crystallogr C Struct Chem. 2018 Mar 1;74(Pt 3):274-282. doi: 10.1107/S2053229618001791. Epub 2018 Feb 6. [PubMed:29504554 ]
  5. Cai X, Zhou X, Zheng Z, Zhong W, Li S: (3S,4R,4aS,7aR,12bS)-3-Cyclo-propyl-meth-yl-4a,9-dihy-droxy-3-methyl-7-oxo-2,3,4, 4a,5,6,7,7a-octa-hydro-1H-4,12-methano-1-benzofuro[3,2-e]isoquinolin-3-ium 2,2,2-trifluoro-acetate methanol solvate. Acta Crystallogr Sect E Struct Rep Online. 2010 Oct 20;66(Pt 11):o2868. doi: 10.1107/S1600536810041164. [PubMed:21589050 ]
  6. Ma, Y.-Y., et al. (2013). Ma, Y.-Y., et al, Phytochem. Lett. 6, 645 (2013). Phytochem..