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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:53:30 UTC
Update Date2022-03-07 02:54:17 UTC
HMDB IDHMDB0034957
Secondary Accession Numbers
  • HMDB34957
Metabolite Identification
Common Name(13R,14R)-8-Labdene-13,14,15-triol
Description(13R,14R)-8-Labdene-13,14,15-triol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review a small amount of articles have been published on (13R,14R)-8-Labdene-13,14,15-triol.
Structure
Data?1563862642
SynonymsNot Available
Chemical FormulaC20H36O3
Average Molecular Weight324.498
Monoisotopic Molecular Weight324.266445018
IUPAC Name5-(2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-methylpentane-1,2,3-triol
Traditional Name5-(2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpentane-1,2,3-triol
CAS Registry NumberNot Available
SMILES
CC1=C(CCC(C)(O)C(O)CO)C2(C)CCCC(C)(C)C2CC1
InChI Identifier
InChI=1S/C20H36O3/c1-14-7-8-16-18(2,3)10-6-11-19(16,4)15(14)9-12-20(5,23)17(22)13-21/h16-17,21-23H,6-13H2,1-5H3
InChI KeyTWZQRBKMQYAKGQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassDiterpenoids
Direct ParentDiterpenoids
Alternative Parents
Substituents
  • Diterpenoid
  • Labdane diterpenoid
  • Fatty alcohol
  • Fatty acyl
  • Tertiary alcohol
  • Secondary alcohol
  • Polyol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.048 g/LALOGPS
logP3.55ALOGPS
logP3.15ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)13.16ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.98 m³·mol⁻¹ChemAxon
Polarizability38.99 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]+178.32431661259
DarkChem[M-H]-173.53631661259
DeepCCS[M+H]+181.89730932474
DeepCCS[M-H]-179.53930932474
DeepCCS[M-2H]-213.02930932474
DeepCCS[M+Na]+188.25630932474
AllCCS[M+H]+182.832859911
AllCCS[M+H-H2O]+180.032859911
AllCCS[M+NH4]+185.332859911
AllCCS[M+Na]+186.032859911
AllCCS[M-H]-186.532859911
AllCCS[M+Na-2H]-187.532859911
AllCCS[M+HCOO]-188.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(13R,14R)-8-Labdene-13,14,15-triolCC1=C(CCC(C)(O)C(O)CO)C2(C)CCCC(C)(C)C2CC12625.7Standard polar33892256
(13R,14R)-8-Labdene-13,14,15-triolCC1=C(CCC(C)(O)C(O)CO)C2(C)CCCC(C)(C)C2CC12499.2Standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triolCC1=C(CCC(C)(O)C(O)CO)C2(C)CCCC(C)(C)C2CC12562.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(13R,14R)-8-Labdene-13,14,15-triol,1TMS,isomer #1CC1=C(CCC(C)(O[Si](C)(C)C)C(O)CO)C2(C)CCCC(C)(C)C2CC12618.1Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,1TMS,isomer #2CC1=C(CCC(C)(O)C(CO)O[Si](C)(C)C)C2(C)CCCC(C)(C)C2CC12591.6Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,1TMS,isomer #3CC1=C(CCC(C)(O)C(O)CO[Si](C)(C)C)C2(C)CCCC(C)(C)C2CC12601.0Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,2TMS,isomer #1CC1=C(CCC(C)(O[Si](C)(C)C)C(CO)O[Si](C)(C)C)C2(C)CCCC(C)(C)C2CC12653.4Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,2TMS,isomer #2CC1=C(CCC(C)(O[Si](C)(C)C)C(O)CO[Si](C)(C)C)C2(C)CCCC(C)(C)C2CC12646.3Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,2TMS,isomer #3CC1=C(CCC(C)(O)C(CO[Si](C)(C)C)O[Si](C)(C)C)C2(C)CCCC(C)(C)C2CC12633.1Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,3TMS,isomer #1CC1=C(CCC(C)(O[Si](C)(C)C)C(CO[Si](C)(C)C)O[Si](C)(C)C)C2(C)CCCC(C)(C)C2CC12706.3Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,1TBDMS,isomer #1CC1=C(CCC(C)(O[Si](C)(C)C(C)(C)C)C(O)CO)C2(C)CCCC(C)(C)C2CC12860.8Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,1TBDMS,isomer #2CC1=C(CCC(C)(O)C(CO)O[Si](C)(C)C(C)(C)C)C2(C)CCCC(C)(C)C2CC12834.5Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,1TBDMS,isomer #3CC1=C(CCC(C)(O)C(O)CO[Si](C)(C)C(C)(C)C)C2(C)CCCC(C)(C)C2CC12838.8Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,2TBDMS,isomer #1CC1=C(CCC(C)(O[Si](C)(C)C(C)(C)C)C(CO)O[Si](C)(C)C(C)(C)C)C2(C)CCCC(C)(C)C2CC13111.1Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,2TBDMS,isomer #2CC1=C(CCC(C)(O[Si](C)(C)C(C)(C)C)C(O)CO[Si](C)(C)C(C)(C)C)C2(C)CCCC(C)(C)C2CC13104.8Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,2TBDMS,isomer #3CC1=C(CCC(C)(O)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C2(C)CCCC(C)(C)C2CC13100.2Semi standard non polar33892256
(13R,14R)-8-Labdene-13,14,15-triol,3TBDMS,isomer #1CC1=C(CCC(C)(O[Si](C)(C)C(C)(C)C)C(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C2(C)CCCC(C)(C)C2CC13383.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-6295000000-115a12ea2d2c42b7d6ea2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol GC-MS (3 TMS) - 70eV, Positivesplash10-004i-5252590000-a71d26aab944c6ce18562017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol 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 - (13R,14R)-8-Labdene-13,14,15-triol 10V, Positive-QTOFsplash10-056r-0169000000-c776814570f5d0fdf56b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol 20V, Positive-QTOFsplash10-0avi-4492000000-5e466b23f512194c3fc52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol 40V, Positive-QTOFsplash10-052b-6981000000-e861c7cda5c89b925e982016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol 10V, Negative-QTOFsplash10-00di-0029000000-4c7d938103ad521a36fb2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol 20V, Negative-QTOFsplash10-08fr-4094000000-e667a8068e2a05b4c12c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol 40V, Negative-QTOFsplash10-06re-9160000000-c2ce3ef1c01e852f50ae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol 10V, Positive-QTOFsplash10-004i-1298000000-5963c7efc975a54479612021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol 20V, Positive-QTOFsplash10-0076-2931000000-502f3bbdd65ebbc9b7582021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol 40V, Positive-QTOFsplash10-05br-4900000000-f5129b5040690b6dd6042021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol 10V, Negative-QTOFsplash10-00di-0009000000-b12b922a185d63cdc0bd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol 20V, Negative-QTOFsplash10-05fr-3049000000-f7724f937e6fcb06a1372021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (13R,14R)-8-Labdene-13,14,15-triol 40V, Negative-QTOFsplash10-014i-3191000000-146e96610bc50bf0172a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDFDB013551
KNApSAcK IDNot Available
Chemspider ID35013803
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14543666
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.