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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:46:33 UTC
Update Date2022-03-07 02:53:10 UTC
HMDB IDHMDB0031924
Secondary Accession Numbers
  • HMDB31924
Metabolite Identification
Common Name4-Nerolidylcatechol
Description4-Nerolidylcatechol 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 4-Nerolidylcatechol.
Structure
Data?1563862192
Synonyms
ValueSource
3-(3,4-Dihydroxyphenyl)-3,7,11-trimethyl-1,6,10-dodecatrieneHMDB
4-NerolidylcatecholMeSH
Chemical FormulaC21H30O2
Average Molecular Weight314.4617
Monoisotopic Molecular Weight314.224580204
IUPAC Name4-[(6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl]benzene-1,2-diol
Traditional Name4-[(6E)-3,7,11-trimethyldodeca-1,6,10-trien-3-yl]benzene-1,2-diol
CAS Registry Number74683-11-7
SMILES
CC(C)=CCC\C(C)=C\CCC(C)(C=C)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C21H30O2/c1-6-21(5,18-12-13-19(22)20(23)15-18)14-8-11-17(4)10-7-9-16(2)3/h6,9,11-13,15,22-23H,1,7-8,10,14H2,2-5H3/b17-11+
InChI KeyZBZZDHDWRSFLAY-GZTJUZNOSA-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
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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 Solubility0.007 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0081 g/LALOGPS
logP6.49ALOGPS
logP6.37ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.26ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity100.94 m³·mol⁻¹ChemAxon
Polarizability38.01 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+177.29331661259
DarkChem[M-H]-175.96531661259
DeepCCS[M+H]+183.64530932474
DeepCCS[M-H]-181.25830932474
DeepCCS[M-2H]-214.89730932474
DeepCCS[M+Na]+190.47830932474
AllCCS[M+H]+182.232859911
AllCCS[M+H-H2O]+179.132859911
AllCCS[M+NH4]+185.132859911
AllCCS[M+Na]+185.932859911
AllCCS[M-H]-182.832859911
AllCCS[M+Na-2H]-183.132859911
AllCCS[M+HCOO]-183.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-NerolidylcatecholCC(C)=CCC\C(C)=C\CCC(C)(C=C)C1=CC(O)=C(O)C=C13553.0Standard polar33892256
4-NerolidylcatecholCC(C)=CCC\C(C)=C\CCC(C)(C=C)C1=CC(O)=C(O)C=C12349.3Standard non polar33892256
4-NerolidylcatecholCC(C)=CCC\C(C)=C\CCC(C)(C=C)C1=CC(O)=C(O)C=C12455.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Nerolidylcatechol,1TMS,isomer #1C=CC(C)(CC/C=C(\C)CCC=C(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C12454.8Semi standard non polar33892256
4-Nerolidylcatechol,1TMS,isomer #2C=CC(C)(CC/C=C(\C)CCC=C(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C12473.0Semi standard non polar33892256
4-Nerolidylcatechol,2TMS,isomer #1C=CC(C)(CC/C=C(\C)CCC=C(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C12507.9Semi standard non polar33892256
4-Nerolidylcatechol,1TBDMS,isomer #1C=CC(C)(CC/C=C(\C)CCC=C(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C12704.3Semi standard non polar33892256
4-Nerolidylcatechol,1TBDMS,isomer #2C=CC(C)(CC/C=C(\C)CCC=C(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C12719.2Semi standard non polar33892256
4-Nerolidylcatechol,2TBDMS,isomer #1C=CC(C)(CC/C=C(\C)CCC=C(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C12964.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nerolidylcatechol GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-2930000000-5744e41784b4b3f1d8702017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nerolidylcatechol GC-MS (2 TMS) - 70eV, Positivesplash10-0006-4325900000-a612e2078ad72b0e7e9b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Nerolidylcatechol 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 - 4-Nerolidylcatechol 10V, Positive-QTOFsplash10-014i-0269000000-a34c785d7cd1d34cdde82016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nerolidylcatechol 20V, Positive-QTOFsplash10-014i-3972000000-97ffd28b7f5fb930b2bb2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nerolidylcatechol 40V, Positive-QTOFsplash10-0gb9-9620000000-b3f9c53b93644d136fb32016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nerolidylcatechol 10V, Negative-QTOFsplash10-03di-0009000000-57aa690fbed4235f406a2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nerolidylcatechol 20V, Negative-QTOFsplash10-03di-0149000000-38c630048d77241a741d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nerolidylcatechol 40V, Negative-QTOFsplash10-0a4j-1490000000-3e3a9e0127649d71b9c62016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nerolidylcatechol 10V, Positive-QTOFsplash10-01c0-5921000000-7a886ffd8eb43f46adae2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nerolidylcatechol 20V, Positive-QTOFsplash10-0apj-9720000000-3ca75c98db6b6281ba942021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nerolidylcatechol 40V, Positive-QTOFsplash10-06tf-9700000000-2809bd9eba97e98dc3982021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nerolidylcatechol 10V, Negative-QTOFsplash10-03di-0009000000-2514638890974c4f71f32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nerolidylcatechol 20V, Negative-QTOFsplash10-03di-0329000000-0b8f2aee1e132c1e064c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Nerolidylcatechol 40V, Negative-QTOFsplash10-03y0-4922000000-897ec86c19e83b8983e62021-09-25Wishart 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 IDFDB008612
KNApSAcK IDC00057535
Chemspider ID4509046
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5352089
PDB IDNot Available
ChEBI ID174288
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1828741
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.