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Record Information
Version1.0
Created at2022-09-12 09:24:10 UTC
Updated at2022-09-12 09:24:10 UTC
NP-MRD IDNP0327129
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1s,4s,5s,6s,7r,10s)-7-isopropyl-4,10-dimethyltricyclo[4.4.0.0¹,⁵]decan-4-ol
Description(+)-4-Epi-cubebol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1s,4s,5s,6s,7r,10s)-7-isopropyl-4,10-dimethyltricyclo[4.4.0.0¹,⁵]decan-4-ol is found in Taonia atomaria. It was first documented in 2012 (PMID: 23373215). Based on a literature review a significant number of articles have been published on (+)-4-epi-cubebol (PMID: 36130844) (PMID: 36130843) (PMID: 36130842) (PMID: 35163853).
Structure
Thumb
Synonyms
ValueSource
(+)-4-EpicubebolChEBI
(3S,3AS,3BS,4R,7S,7as)-4-(2-hydroxypropan-2-yl)-7-methyloctahydro-1H-cyclopenta[1,3]cyclopropa[1,2]benzen-3-olChEBI
4-Epi-cubebolChEBI
Chemical FormulaC15H26O
Average Mass222.3720 Da
Monoisotopic Mass222.19837 Da
IUPAC Name(1S,4S,5S,6S,7R,10S)-4,10-dimethyl-7-(propan-2-yl)tricyclo[4.4.0.0^{1,5}]decan-4-ol
Traditional Name(1S,4S,5S,6S,7R,10S)-7-isopropyl-4,10-dimethyltricyclo[4.4.0.0^{1,5}]decan-4-ol
CAS Registry NumberNot Available
SMILES
CC(C)[C@H]1CC[C@H](C)[C@]23CC[C@](C)(O)[C@H]2[C@H]13
InChI Identifier
InChI=1S/C15H26O/c1-9(2)11-6-5-10(3)15-8-7-14(4,16)13(15)12(11)15/h9-13,16H,5-8H2,1-4H3/t10-,11+,12-,13+,14-,15-/m0/s1
InChI KeyKONGRWVLXLWGDV-DEPYFDJDSA-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 Origin
Species NameSourceReference
Taonia atomariaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Cubebane sesquiterpenoid
  • Sesquiterpenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • 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
logP3.18ChemAxon
pKa (Strongest Acidic)19.39ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.6 m³·mol⁻¹ChemAxon
Polarizability27.42 ųChemAxon
Number of Rings3ChemAxon
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 ID30772459
KEGG Compound IDNot Available
BioCyc IDCPD-20135
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12304217
PDB IDNot Available
ChEBI ID138041
Good Scents IDNot Available
References
General References
  1. Zhang PP, Gao SS, Zhang TT, Chen JC, Duan HQ, Fang JB: [Sesquiterpenes from stem of Schisandra glaucescens]. Zhongguo Zhong Yao Za Zhi. 2012 Nov;37(22):3426-9. [PubMed:23373215 ]
  2. Cani I, Righini M, Cenni P, Foschi M: Teaching NeuroImage: Partially Reversible Widespread Leukoencephalopathy Associated With Atypical Hemolytic Uremic Syndrome. Neurology. 2022 Sep 21. pii: WNL.0000000000201378. doi: 10.1212/WNL.0000000000201378. [PubMed:36130844 ]
  3. Sasaki R, Morimoto S, Ozawa F, Okano H, Yoshida M, Ishiura H, Tsuji S, Kuzuhara S, Kokubo Y: APOE Alleles With Tau and Abeta Pathology In Patients With Amyotrophic Lateral Sclerosis and Parkinsonism-Dementia Complex in the Kii Peninsula. Neurology. 2022 Sep 21. pii: WNL.0000000000201156. doi: 10.1212/WNL.0000000000201156. [PubMed:36130843 ]
  4. Zhang Z, Wang M, Gill D, Liu X: Genetically Predicted Smoking and Alcohol Consumption and Functional Outcome After Ischemic Stroke. Neurology. 2022 Sep 21. pii: WNL.0000000000201291. doi: 10.1212/WNL.0000000000201291. [PubMed:36130842 ]
  5. Basile S, Badalamenti N, Riccobono O, Guarino S, Ilardi V, Bruno M, Peri E: Chemical Composition and Evaluation of Insecticidal Activity of Calendula incana subsp. maritima and Laserpitium siler subsp. siculum Essential Oils against Stored Products Pests. Molecules. 2022 Jan 18;27(3):588. doi: 10.3390/molecules27030588. [PubMed:35163853 ]
  6. LOTUS database [Link]