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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:27:38 UTC
Update Date2022-03-07 02:54:52 UTC
HMDB IDHMDB0036328
Secondary Accession Numbers
  • HMDB36328
Metabolite Identification
Common NameNordihydrocapsaicin
DescriptionNordihydrocapsaicin belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Thus, nordihydrocapsaicin is considered to be a fatty amide. Nordihydrocapsaicin is found, on average, in the highest concentration within a few different foods, such as yellow bell peppers (Capsicum annuum), red bell peppers (Capsicum annuum), and peppers (Capsicum annuum) and in a lower concentration in orange bell peppers (Capsicum annuum), green bell peppers (Capsicum annuum), and pepper (c. frutescens). Nordihydrocapsaicin has also been detected, but not quantified in, herbs and spices and italian sweet red peppers (Capsicum annuum). This could make nordihydrocapsaicin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Nordihydrocapsaicin.
Structure
Data?1563862858
Synonyms
ValueSource
N-((4-H Ydroxy-3-methoxyphenyl)methyl)-7-methyl-octanamideKegg
7-Methyl nordihydrocapsaicinHMDB
N-((4-Hydroxy-3-methoxyphenyl)methyl)-7-methyl-octanamideHMDB
N-[(4-Hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide, 9ciHMDB
NordihydrocapsacinHMDB
Chemical FormulaC17H27NO3
Average Molecular Weight293.4012
Monoisotopic Molecular Weight293.199093735
IUPAC NameN-[(4-hydroxy-3-methoxyphenyl)methyl]-7-methyloctanamide
Traditional Namenordihydrocapsaicin
CAS Registry Number28789-35-7
SMILES
COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O
InChI Identifier
InChI=1S/C17H27NO3/c1-13(2)7-5-4-6-8-17(20)18-12-14-9-10-15(19)16(11-14)21-3/h9-11,13,19H,4-8,12H2,1-3H3,(H,18,20)
InChI KeyVQEONGKQWIFHMN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentMethoxyphenols
Alternative Parents
Substituents
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Fatty acyl
  • Fatty amide
  • N-acyl-amine
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Ether
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point60 - 61 °CNot Available
Boiling Point486.00 to 187.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility8.92 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.046 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.031 g/LALOGPS
logP3.85ALOGPS
logP3.67ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.93ChemAxon
pKa (Strongest Basic)-0.52ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area58.56 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity84.6 m³·mol⁻¹ChemAxon
Polarizability34.35 ųChemAxon
Number of Rings1ChemAxon
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]+172.20131661259
DarkChem[M-H]-169.59331661259
DeepCCS[M+H]+174.31830932474
DeepCCS[M-H]-171.96130932474
DeepCCS[M-2H]-205.37930932474
DeepCCS[M+Na]+180.7330932474
AllCCS[M+H]+173.632859911
AllCCS[M+H-H2O]+170.632859911
AllCCS[M+NH4]+176.532859911
AllCCS[M+Na]+177.332859911
AllCCS[M-H]-175.032859911
AllCCS[M+Na-2H]-175.832859911
AllCCS[M+HCOO]-176.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
NordihydrocapsaicinCOC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O3526.8Standard polar33892256
NordihydrocapsaicinCOC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O2395.9Standard non polar33892256
NordihydrocapsaicinCOC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O2489.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Nordihydrocapsaicin,1TMS,isomer #1COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O[Si](C)(C)C2570.6Semi standard non polar33892256
Nordihydrocapsaicin,1TMS,isomer #2COC1=CC(CN(C(=O)CCCCCC(C)C)[Si](C)(C)C)=CC=C1O2412.3Semi standard non polar33892256
Nordihydrocapsaicin,2TMS,isomer #1COC1=CC(CN(C(=O)CCCCCC(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2475.6Semi standard non polar33892256
Nordihydrocapsaicin,2TMS,isomer #1COC1=CC(CN(C(=O)CCCCCC(C)C)[Si](C)(C)C)=CC=C1O[Si](C)(C)C2446.1Standard non polar33892256
Nordihydrocapsaicin,1TBDMS,isomer #1COC1=CC(CNC(=O)CCCCCC(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2819.1Semi standard non polar33892256
Nordihydrocapsaicin,1TBDMS,isomer #2COC1=CC(CN(C(=O)CCCCCC(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O2650.6Semi standard non polar33892256
Nordihydrocapsaicin,2TBDMS,isomer #1COC1=CC(CN(C(=O)CCCCCC(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2962.5Semi standard non polar33892256
Nordihydrocapsaicin,2TBDMS,isomer #1COC1=CC(CN(C(=O)CCCCCC(C)C)[Si](C)(C)C(C)(C)C)=CC=C1O[Si](C)(C)C(C)(C)C2846.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Nordihydrocapsaicin GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9640000000-3871bb96b69d2739de972017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nordihydrocapsaicin GC-MS (1 TMS) - 70eV, Positivesplash10-0f6x-9343000000-f1cfb2ff65932798e65a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Nordihydrocapsaicin 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 - Nordihydrocapsaicin 10V, Positive-QTOFsplash10-0udi-0930000000-60430aef9c68c490ba732016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordihydrocapsaicin 20V, Positive-QTOFsplash10-0udi-0900000000-385b7852c874b3cdd6112016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordihydrocapsaicin 40V, Positive-QTOFsplash10-052r-4900000000-259a3bed23b06b519d142016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordihydrocapsaicin 10V, Negative-QTOFsplash10-0006-0390000000-8c0c3a713f8fd8b81d332016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordihydrocapsaicin 20V, Negative-QTOFsplash10-006x-0950000000-c619e8fddd2c823a8eb12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordihydrocapsaicin 40V, Negative-QTOFsplash10-0006-7900000000-d570a865813f7e0704f42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordihydrocapsaicin 10V, Positive-QTOFsplash10-000i-0920000000-97edc9bdd81feca705bd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordihydrocapsaicin 20V, Positive-QTOFsplash10-000i-1900000000-851a3e10d3faf2609c272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordihydrocapsaicin 40V, Positive-QTOFsplash10-000i-3900000000-63974c1e31c3ed3abbab2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordihydrocapsaicin 10V, Negative-QTOFsplash10-0a4i-0900000000-88603c67cdd1dc1ce3e52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordihydrocapsaicin 20V, Negative-QTOFsplash10-052o-6900000000-118ac3f38f60cd33e2052021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Nordihydrocapsaicin 40V, Negative-QTOFsplash10-0006-9300000000-19b6d44cfd12492a0a032021-09-23Wishart 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 ID1052
FooDB IDFDB015199
KNApSAcK IDC00057327
Chemspider ID147689
KEGG Compound IDC20216
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNordihydrocapsaicin
METLIN IDNot Available
PubChem Compound168836
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1381471
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .