Hmdb loader
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 23:25:58 UTC
Update Date2022-09-22 18:35:11 UTC
HMDB IDHMDB0038149
Secondary Accession Numbers
  • HMDB38149
Metabolite Identification
Common NameNepetaside
DescriptionNepetaside belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Based on a literature review a small amount of articles have been published on Nepetaside.
Structure
Data?1563863147
Synonyms
ValueSource
(-)-NepetasideHMDB
Chemical FormulaC16H26O8
Average Molecular Weight346.3728
Monoisotopic Molecular Weight346.162767808
IUPAC Name4,7-dimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydrocyclopenta[c]pyran-1-one
Traditional Name4,7-dimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydro-3H-cyclopenta[c]pyran-1-one
CAS Registry Number114076-56-1
SMILES
CC1C(CC2C1C(=O)OCC2C)OC1OC(CO)C(O)C(O)C1O
InChI Identifier
InChI=1S/C16H26O8/c1-6-5-22-15(21)11-7(2)9(3-8(6)11)23-16-14(20)13(19)12(18)10(4-17)24-16/h6-14,16-20H,3-5H2,1-2H3
InChI KeyCUIDBUWFCFYEPL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene glycosides
Direct ParentTerpene glycosides
Alternative Parents
Substituents
  • Terpene glycoside
  • Terpene lactone
  • Hexose monosaccharide
  • Glycosyl compound
  • Iridoid-skeleton
  • O-glycosyl compound
  • Bicyclic monoterpenoid
  • Monoterpenoid
  • Delta valerolactone
  • Delta_valerolactone
  • Monosaccharide
  • Oxane
  • Lactone
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Carboxylic acid derivative
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point204 - 205 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility128800 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility32.6 g/LALOGPS
logP-1ALOGPS
logP-1ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area125.68 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.86 m³·mol⁻¹ChemAxon
Polarizability35.15 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+180.08731661259
DarkChem[M-H]-177.07231661259
DeepCCS[M+H]+179.79730932474
DeepCCS[M-H]-177.43930932474
DeepCCS[M-2H]-210.95930932474
DeepCCS[M+Na]+186.18630932474
AllCCS[M+H]+181.732859911
AllCCS[M+H-H2O]+178.832859911
AllCCS[M+NH4]+184.332859911
AllCCS[M+Na]+185.132859911
AllCCS[M-H]-180.732859911
AllCCS[M+Na-2H]-180.832859911
AllCCS[M+HCOO]-181.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NepetasideCC1C(CC2C1C(=O)OCC2C)OC1OC(CO)C(O)C(O)C1O3547.5Standard polar33892256
NepetasideCC1C(CC2C1C(=O)OCC2C)OC1OC(CO)C(O)C(O)C1O2705.6Standard non polar33892256
NepetasideCC1C(CC2C1C(=O)OCC2C)OC1OC(CO)C(O)C(O)C1O2967.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nepetaside,1TMS,isomer #1CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O)CC122899.5Semi standard non polar33892256
Nepetaside,1TMS,isomer #2CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O)CC122905.1Semi standard non polar33892256
Nepetaside,1TMS,isomer #3CC1COC(=O)C2C(C)C(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O)CC122900.5Semi standard non polar33892256
Nepetaside,1TMS,isomer #4CC1COC(=O)C2C(C)C(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C)CC122900.4Semi standard non polar33892256
Nepetaside,2TMS,isomer #1CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O)CC122913.5Semi standard non polar33892256
Nepetaside,2TMS,isomer #2CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O)CC122917.9Semi standard non polar33892256
Nepetaside,2TMS,isomer #3CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O[Si](C)(C)C)CC122890.8Semi standard non polar33892256
Nepetaside,2TMS,isomer #4CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)CC122904.3Semi standard non polar33892256
Nepetaside,2TMS,isomer #5CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)CC122897.1Semi standard non polar33892256
Nepetaside,2TMS,isomer #6CC1COC(=O)C2C(C)C(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)CC122907.4Semi standard non polar33892256
Nepetaside,3TMS,isomer #1CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)CC122867.7Semi standard non polar33892256
Nepetaside,3TMS,isomer #2CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)CC122846.3Semi standard non polar33892256
Nepetaside,3TMS,isomer #3CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)CC122841.8Semi standard non polar33892256
Nepetaside,3TMS,isomer #4CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)CC122848.7Semi standard non polar33892256
Nepetaside,4TMS,isomer #1CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)CC122778.3Semi standard non polar33892256
Nepetaside,1TBDMS,isomer #1CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O)CC123146.3Semi standard non polar33892256
Nepetaside,1TBDMS,isomer #2CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)CC123146.1Semi standard non polar33892256
Nepetaside,1TBDMS,isomer #3CC1COC(=O)C2C(C)C(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)CC123146.0Semi standard non polar33892256
Nepetaside,1TBDMS,isomer #4CC1COC(=O)C2C(C)C(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)CC123135.2Semi standard non polar33892256
Nepetaside,2TBDMS,isomer #1CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)CC123352.5Semi standard non polar33892256
Nepetaside,2TBDMS,isomer #2CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)CC123359.9Semi standard non polar33892256
Nepetaside,2TBDMS,isomer #3CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)CC123331.8Semi standard non polar33892256
Nepetaside,2TBDMS,isomer #4CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)CC123338.5Semi standard non polar33892256
Nepetaside,2TBDMS,isomer #5CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)CC123336.5Semi standard non polar33892256
Nepetaside,2TBDMS,isomer #6CC1COC(=O)C2C(C)C(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)CC123342.9Semi standard non polar33892256
Nepetaside,3TBDMS,isomer #1CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)CC123531.2Semi standard non polar33892256
Nepetaside,3TBDMS,isomer #2CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)CC123524.3Semi standard non polar33892256
Nepetaside,3TBDMS,isomer #3CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)CC123518.8Semi standard non polar33892256
Nepetaside,3TBDMS,isomer #4CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)CC123513.8Semi standard non polar33892256
Nepetaside,4TBDMS,isomer #1CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)CC123703.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nepetaside GC-MS (Non-derivatized) - 70eV, Positivesplash10-08i9-7497000000-9a797b13d76058dadd6e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nepetaside GC-MS (4 TMS) - 70eV, Positivesplash10-00xr-2400169000-0cb3b94098a768406de72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nepetaside GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nepetaside 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 - Nepetaside 10V, Positive-QTOFsplash10-00ks-0905000000-72d86d00be62ab9078672015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nepetaside 20V, Positive-QTOFsplash10-00kr-0900000000-6180db475af51bf5a0522015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nepetaside 40V, Positive-QTOFsplash10-014u-5900000000-1cf5b1299bdfc1b7f52f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nepetaside 10V, Negative-QTOFsplash10-000t-1809000000-709fa73380a7cfe5d1302015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nepetaside 20V, Negative-QTOFsplash10-001i-1901000000-64d9d6f8cb4e75e4e9b22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nepetaside 40V, Negative-QTOFsplash10-001r-3900000000-34b8e8b9828f8c3271e92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nepetaside 10V, Negative-QTOFsplash10-0002-0009000000-49d51033851b8149b7562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nepetaside 20V, Negative-QTOFsplash10-052b-9537000000-36e41df86e064cacda9b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nepetaside 40V, Negative-QTOFsplash10-0a4i-9431000000-946c136ac5f6f7d2235b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nepetaside 10V, Positive-QTOFsplash10-00kb-0809000000-d0b521973fac096fe0422021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nepetaside 20V, Positive-QTOFsplash10-014i-0901000000-f39870fca51caa284de02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nepetaside 40V, Positive-QTOFsplash10-02t9-4900000000-3ca51e1d156883484c902021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAsthma details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017377
KNApSAcK IDC00010642
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14020067
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1866041
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.