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Record Information
Version2.0
Created at2022-09-06 14:06:36 UTC
Updated at2022-09-06 14:06:36 UTC
NP-MRD IDNP0232766
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1r,2s,4r,6r,7s,8s)-8-isopropyl-1-methyl-3-methylidenetricyclo[4.4.0.0²,⁷]decan-4-ol
DescriptionLemnalol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (1r,2s,4r,6r,7s,8s)-8-isopropyl-1-methyl-3-methylidenetricyclo[4.4.0.0²,⁷]decan-4-ol is found in Marsupella aquatica. (1r,2s,4r,6r,7s,8s)-8-isopropyl-1-methyl-3-methylidenetricyclo[4.4.0.0²,⁷]decan-4-ol was first documented in 2010 (PMID: 20190445). Based on a literature review a small amount of articles have been published on Lemnalol (PMID: 31671563) (PMID: 25557511) (PMID: 23306170) (PMID: 22067479).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H24O
Average Mass220.3560 Da
Monoisotopic Mass220.18272 Da
IUPAC Name(1R,2S,4R,6R,7S,8S)-1-methyl-3-methylidene-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]decan-4-ol
Traditional Name(1R,2S,4R,6R,7S,8S)-8-isopropyl-1-methyl-3-methylidenetricyclo[4.4.0.0^{2,7}]decan-4-ol
CAS Registry NumberNot Available
SMILES
CC(C)[C@@H]1CC[C@]2(C)[C@@H]3C[C@@H](O)C(=C)[C@H]2[C@@H]13
InChI Identifier
InChI=1S/C15H24O/c1-8(2)10-5-6-15(4)11-7-12(16)9(3)14(15)13(10)11/h8,10-14,16H,3,5-7H2,1-2,4H3/t10-,11+,12+,13-,14-,15+/m0/s1
InChI KeyLPXOPRGPLUWGKB-VRPMWHRCSA-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
Marsupella aquaticaLOTUS 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
  • Copaane sesquiterpenoid
  • Sesquiterpenoid
  • Cyclic alcohol
  • Secondary 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
logP2.92ChemAxon
pKa (Strongest Acidic)17.92ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity66.21 m³·mol⁻¹ChemAxon
Polarizability82.11 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 IDC00021984
Chemspider ID24716816
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44584340
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Tai BY, Wen ZH, Cheng PY, Yang HY, Duh CY, Chen PN, Hsu CH: Lemnalol Modulates the Electrophysiological Characteristics and Calcium Homeostasis of Atrial Myocytes. Mar Drugs. 2019 Oct 30;17(11):619. doi: 10.3390/md17110619. [PubMed:31671563 ]
  2. Lee HP, Lin YY, Duh CY, Huang SY, Wang HM, Wu SF, Lin SC, Jean YH, Wen ZH: Lemnalol attenuates mast cell activation and osteoclast activity in a gouty arthritis model. J Pharm Pharmacol. 2015 Feb;67(2):274-85. doi: 10.1111/jphp.12331. Epub 2014 Dec 31. [PubMed:25557511 ]
  3. Lee HP, Huang SY, Lin YY, Wang HM, Jean YH, Wu SF, Duh CY, Wen ZH: Soft coral-derived lemnalol alleviates monosodium urate-induced gouty arthritis in rats by inhibiting leukocyte infiltration and iNOS, COX-2 and c-Fos protein expression. Mar Drugs. 2013 Jan 10;11(1):99-113. doi: 10.3390/md11010099. [PubMed:23306170 ]
  4. Lin YC, Huang SY, Jean YH, Chen WF, Sung CS, Kao ES, Wang HM, Chakraborty C, Duh CY, Wen ZH: Intrathecal lemnalol, a natural marine compound obtained from Formosan soft coral, attenuates nociceptive responses and the activity of spinal glial cells in neuropathic rats. Behav Pharmacol. 2011 Dec;22(8):739-50. doi: 10.1097/FBP.0b013e32834d0ecb. [PubMed:22067479 ]
  5. Cheng SY, Lin EH, Huang JS, Wen ZH, Duh CY: Ylangene-type and nardosinane-type sesquiterpenoids from the soft corals Lemnalia flava and Paralemnalia thyrsoides. Chem Pharm Bull (Tokyo). 2010 Mar;58(3):381-5. doi: 10.1248/cpb.58.381. [PubMed:20190445 ]
  6. LOTUS database [Link]