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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:35:50 UTC
Update Date2022-03-07 02:54:56 UTC
HMDB IDHMDB0036455
Secondary Accession Numbers
  • HMDB36455
Metabolite Identification
Common NameLacinilene C
DescriptionLacinilene C belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Lacinilene C.
Structure
Data?1563862878
Synonyms
ValueSource
1,7-Dihydroxy-1,6-dimethyl-4-(1-methylethyl)-2(1H)-naphthalenone, 9ciHMDB
1,7-Dihydroxy-4-isopropyl-1,6-dimethyl-2(1H)-naphthalenoneHMDB
Chemical FormulaC15H18O3
Average Molecular Weight246.3016
Monoisotopic Molecular Weight246.125594442
IUPAC Name1,7-dihydroxy-1,6-dimethyl-4-(propan-2-yl)-1,2-dihydronaphthalen-2-one
Traditional Name1,7-dihydroxy-4-isopropyl-1,6-dimethylnaphthalen-2-one
CAS Registry Number41653-72-9
SMILES
CC(C)C1=CC(=O)C(C)(O)C2=CC(O)=C(C)C=C12
InChI Identifier
InChI=1S/C15H18O3/c1-8(2)10-6-14(17)15(4,18)12-7-13(16)9(3)5-11(10)12/h5-8,16,18H,1-4H3
InChI KeyJLCJSBOHWRDWQW-UHFFFAOYSA-N
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
  • Cadinane sesquiterpenoid
  • Sesquiterpenoid
  • Naphthalene
  • 1-hydroxy-2-unsubstituted benzenoid
  • Acyloin
  • Benzenoid
  • Tertiary alcohol
  • Ketone
  • Cyclic ketone
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point62 - 63 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility430.7 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.25 g/LALOGPS
logP2.6ALOGPS
logP3.29ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.18ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.78 m³·mol⁻¹ChemAxon
Polarizability27.18 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+159.97131661259
DarkChem[M-H]-154.69131661259
DeepCCS[M-2H]-198.14930932474
DeepCCS[M+Na]+173.71430932474
AllCCS[M+H]+155.132859911
AllCCS[M+H-H2O]+151.432859911
AllCCS[M+NH4]+158.632859911
AllCCS[M+Na]+159.632859911
AllCCS[M-H]-161.632859911
AllCCS[M+Na-2H]-161.732859911
AllCCS[M+HCOO]-161.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Lacinilene CCC(C)C1=CC(=O)C(C)(O)C2=CC(O)=C(C)C=C123449.6Standard polar33892256
Lacinilene CCC(C)C1=CC(=O)C(C)(O)C2=CC(O)=C(C)C=C122026.5Standard non polar33892256
Lacinilene CCC(C)C1=CC(=O)C(C)(O)C2=CC(O)=C(C)C=C122092.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Lacinilene C,1TMS,isomer #1CC1=CC2=C(C=C1O)C(C)(O[Si](C)(C)C)C(=O)C=C2C(C)C2082.8Semi standard non polar33892256
Lacinilene C,1TMS,isomer #2CC1=CC2=C(C=C1O[Si](C)(C)C)C(C)(O)C(=O)C=C2C(C)C2145.6Semi standard non polar33892256
Lacinilene C,2TMS,isomer #1CC1=CC2=C(C=C1O[Si](C)(C)C)C(C)(O[Si](C)(C)C)C(=O)C=C2C(C)C2115.6Semi standard non polar33892256
Lacinilene C,1TBDMS,isomer #1CC1=CC2=C(C=C1O)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)C=C2C(C)C2350.6Semi standard non polar33892256
Lacinilene C,1TBDMS,isomer #2CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(C)(O)C(=O)C=C2C(C)C2415.0Semi standard non polar33892256
Lacinilene C,2TBDMS,isomer #1CC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)C(=O)C=C2C(C)C2643.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Lacinilene C GC-MS (Non-derivatized) - 70eV, Positivesplash10-0uxr-0390000000-d07ceb1aaba363b66c8a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lacinilene C GC-MS (2 TMS) - 70eV, Positivesplash10-0092-1019000000-4fdcf5d46448737d2d472017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lacinilene C GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Lacinilene C GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lacinilene C 10V, Positive-QTOFsplash10-0002-0090000000-1fec773b12d2fff429bf2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lacinilene C 20V, Positive-QTOFsplash10-0kvk-4690000000-d5cedb83b7e6bbb8860a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lacinilene C 40V, Positive-QTOFsplash10-082i-6930000000-2a15f7782aec1f653c2d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lacinilene C 10V, Negative-QTOFsplash10-0002-0090000000-fb3c2286478e2d3d39c12015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lacinilene C 20V, Negative-QTOFsplash10-0002-0090000000-41bd25becb40f39446672015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lacinilene C 40V, Negative-QTOFsplash10-0200-2980000000-00ff3f7d4295417421d42015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lacinilene C 10V, Negative-QTOFsplash10-0002-0090000000-851e47b490f6973ef9e52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lacinilene C 20V, Negative-QTOFsplash10-0002-0090000000-8b13d641cc98844181b82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lacinilene C 40V, Negative-QTOFsplash10-076r-2890000000-2cd6ebfd10fd27bba25c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lacinilene C 10V, Positive-QTOFsplash10-002b-0090000000-889fda9bbb721614b5562021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lacinilene C 20V, Positive-QTOFsplash10-002r-1790000000-e5a2f13e85638ebbe8d22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Lacinilene C 40V, Positive-QTOFsplash10-066r-9710000000-d5dd188827db6e970a652021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015344
KNApSAcK IDC00020116
Chemspider ID19990975
KEGG Compound IDNot Available
BioCyc IDCPD-9754
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound15599876
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1855281
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.