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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:40:20 UTC
Update Date2022-03-07 02:54:35 UTC
HMDB IDHMDB0035663
Secondary Accession Numbers
  • HMDB35663
Metabolite Identification
Common Name(S)-Nerolidol
Description(S)-Nerolidol, also known as (S)-cis-nerolidol or peruviol, 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 (S)-Nerolidol.
Structure
Data?1563862752
Synonyms
ValueSource
(3S,6Z)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-olChEBI
(S)-cis-NerolidolChEBI
(+)-cis-NerolidolHMDB
(+)-NerolidolHMDB
(6Z)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-olHMDB
(Z)-(S)-(+)-3,7,11-Trimethyl-1,6,10-dodecatrien-3-olHMDB
(Z)-NerolidolHMDB
3,7,11-Trimethyl-(3S,6Z)-(+)-1,6,10-dodecatrien-3-olHMDB
3,7,11-Trimethyl-(Z)-(S)-(+)-1,6,10-dodecatrien-3-olHMDB
D-NerolidolHMDB
3,7,11-Trimethyl-1,6,10-dodecatrien-3-olHMDB
Nerolidol, (Z)-isomerHMDB
Nerolidol, (S-(Z))-isomerHMDB
NerolidolHMDB
Nerolidol, (e)-isomerHMDB
Nerolidol, (S-(e))-isomerHMDB
PeruviolHMDB
[S-(Z)]-3,7,11-Trimethyl-1,6,10-dodecatrien-3-olPhytoBank
folic alcoholPhytoBank
cis-(+)-NerolidolPhytoBank
(3S,6Z)-NerolidolPhytoBank
(±)-NerolidolPhytoBank
NerodilolPhytoBank
Chemical FormulaC15H26O
Average Molecular Weight222.3663
Monoisotopic Molecular Weight222.198365454
IUPAC Name(3S,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol
Traditional Name(3S,6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol
CAS Registry Number142-50-7
SMILES
C=C[C@@](C)(O)CC\C=C(\C)CCC=C(C)C
InChI Identifier
InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11-/t15-/m1/s1
InChI KeyFQTLCLSUCSAZDY-QKXCFHHRSA-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
  • Tertiary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting Point19.00 to 21.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point290.00 to 293.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility1.53 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.682 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.021 g/LALOGPS
logP4.55ALOGPS
logP4.31ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)18.46ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity74.01 m³·mol⁻¹ChemAxon
Polarizability27.79 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+155.63631661259
DarkChem[M-H]-155.73931661259
DeepCCS[M+H]+158.76330932474
DeepCCS[M-H]-156.36730932474
DeepCCS[M-2H]-189.46430932474
DeepCCS[M+Na]+164.68930932474
AllCCS[M+H]+159.432859911
AllCCS[M+H-H2O]+155.932859911
AllCCS[M+NH4]+162.732859911
AllCCS[M+Na]+163.732859911
AllCCS[M-H]-158.332859911
AllCCS[M+Na-2H]-159.432859911
AllCCS[M+HCOO]-160.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-NerolidolC=C[C@@](C)(O)CC\C=C(\C)CCC=C(C)C2043.1Standard polar33892256
(S)-NerolidolC=C[C@@](C)(O)CC\C=C(\C)CCC=C(C)C1547.7Standard non polar33892256
(S)-NerolidolC=C[C@@](C)(O)CC\C=C(\C)CCC=C(C)C1583.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-Nerolidol,1TMS,isomer #1C=C[C@](C)(CC/C=C(/C)CCC=C(C)C)O[Si](C)(C)C1670.2Semi standard non polar33892256
(S)-Nerolidol,1TBDMS,isomer #1C=C[C@](C)(CC/C=C(/C)CCC=C(C)C)O[Si](C)(C)C(C)(C)C1910.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - (S)-Nerolidol EI-B (Non-derivatized)splash10-00kf-9100000000-45f6e3893a44769001ce2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (S)-Nerolidol EI-B (Non-derivatized)splash10-00kf-9100000000-45f6e3893a44769001ce2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - (S)-Nerolidol GC-EI-Q (Non-derivatized)splash10-00kf-9300000000-5d0064388349623064552020-07-08HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Nerolidol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0g4u-9710000000-533a8143456d99d529492017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Nerolidol GC-MS (1 TMS) - 70eV, Positivesplash10-009f-9450000000-0e9301ccd24a06b7cb6b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Nerolidol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Nerolidol 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 - (S)-Nerolidol 10V, Positive-QTOFsplash10-0ab9-0490000000-161e693347ad291e0fbd2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Nerolidol 20V, Positive-QTOFsplash10-0avr-8930000000-9d44e8ed0962b3b4a6e52016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Nerolidol 40V, Positive-QTOFsplash10-0gc0-9200000000-e773e83c3d163f0457dd2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Nerolidol 10V, Negative-QTOFsplash10-00di-0090000000-ccfe5910ac69a0881b782016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Nerolidol 20V, Negative-QTOFsplash10-0fk9-0290000000-472fb15ead3e188bca2a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Nerolidol 40V, Negative-QTOFsplash10-0q29-8920000000-480ab5d82bb26f770cf22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Nerolidol 10V, Positive-QTOFsplash10-05gi-9730000000-8f73e6a0f1de3af1ba7d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Nerolidol 20V, Positive-QTOFsplash10-001l-9300000000-2b7789b2b428dddd24982021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Nerolidol 40V, Positive-QTOFsplash10-00l6-9100000000-2f699f362b83b3293a702021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Nerolidol 10V, Negative-QTOFsplash10-00di-0090000000-ab61d8a2af41e6ed2e492021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Nerolidol 20V, Negative-QTOFsplash10-0fk9-0290000000-9251c836633c797793b32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Nerolidol 40V, Negative-QTOFsplash10-0v4i-3930000000-8dc35c7845f0ac5d0fe92021-09-24Wishart 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 IDFDB006275
KNApSAcK IDC00034757
Chemspider ID4512192
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5356544
PDB IDNot Available
ChEBI ID176337
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1384621
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.