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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 23:51:04 UTC
Update Date2022-03-07 02:55:48 UTC
HMDB IDHMDB0038530
Secondary Accession Numbers
  • HMDB38530
Metabolite Identification
Common Name5-Heptadecyl-1,3-benzenediol
Description5-Heptadecyl-1,3-benzenediol, also known as 5-N-heptadecylresorcinol, belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3. 5-Heptadecyl-1,3-benzenediol is found, on average, in the highest concentration within a few different foods, such as rye bread, ryes (Secale cereale), and breakfast cereal and in a lower concentration in wheat bread, pasta, and common wheats (Triticum aestivum). 5-Heptadecyl-1,3-benzenediol has also been detected, but not quantified in, several different foods, such as corns (Zea mays), tartary buckwheats (Fagopyrum tataricum), oriental wheats (Triticum turanicum), millets (Panicum miliaceum), and oats (Avena sativa). This could make 5-heptadecyl-1,3-benzenediol a potential biomarker for the consumption of these foods. 5-Heptadecyl-1,3-benzenediol is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 5-Heptadecyl-1,3-benzenediol.
Structure
Data?1563863212
Synonyms
ValueSource
1,3-Dihydroxy-5-N-heptadecylbenzeneChEBI
5-Heptadecyl-1,3-dihydroxybenzeneChEBI
5-N-HeptadecylresorcinolChEBI
5-Heptadecylbenzene-1,3-diolHMDB
5-HeptadecylresorcinolHMDB
Chemical FormulaC23H40O2
Average Molecular Weight348.5625
Monoisotopic Molecular Weight348.302830524
IUPAC Name5-heptadecylbenzene-1,3-diol
Traditional Name5-heptadecylbenzene-1,3-diol
CAS Registry Number41442-57-3
SMILES
CCCCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C1
InChI Identifier
InChI=1S/C23H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21-18-22(24)20-23(25)19-21/h18-20,24-25H,2-17H2,1H3
InChI KeyBBGNINPPDHJETF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as resorcinols. Resorcinols are compounds containing a resorcinol moiety, which is a benzene ring bearing two hydroxyl groups at positions 1 and 3.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentResorcinols
Alternative Parents
Substituents
  • Resorcinol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted 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
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point91 - 93 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00018 g/LALOGPS
logP8.79ALOGPS
logP8.99ChemAxon
logS-6.3ALOGPS
pKa (Strongest Acidic)9.36ChemAxon
pKa (Strongest Basic)-5.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity108.68 m³·mol⁻¹ChemAxon
Polarizability46.6 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
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]+192.36131661259
DarkChem[M-H]-194.73931661259
DeepCCS[M+H]+196.73930932474
DeepCCS[M-H]-194.31330932474
DeepCCS[M-2H]-227.39230932474
DeepCCS[M+Na]+203.08230932474
AllCCS[M+H]+199.032859911
AllCCS[M+H-H2O]+196.332859911
AllCCS[M+NH4]+201.432859911
AllCCS[M+Na]+202.132859911
AllCCS[M-H]-196.932859911
AllCCS[M+Na-2H]-198.932859911
AllCCS[M+HCOO]-201.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Heptadecyl-1,3-benzenediolCCCCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C13816.3Standard polar33892256
5-Heptadecyl-1,3-benzenediolCCCCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C12955.2Standard non polar33892256
5-Heptadecyl-1,3-benzenediolCCCCCCCCCCCCCCCCCC1=CC(O)=CC(O)=C13044.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Heptadecyl-1,3-benzenediol,1TMS,isomer #1CCCCCCCCCCCCCCCCCC1=CC(O)=CC(O[Si](C)(C)C)=C12945.5Semi standard non polar33892256
5-Heptadecyl-1,3-benzenediol,2TMS,isomer #1CCCCCCCCCCCCCCCCCC1=CC(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C12902.6Semi standard non polar33892256
5-Heptadecyl-1,3-benzenediol,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCC1=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C13192.7Semi standard non polar33892256
5-Heptadecyl-1,3-benzenediol,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCC1=CC(O[Si](C)(C)C(C)(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C13390.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Heptadecyl-1,3-benzenediol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00du-5941000000-d13e6df10977cf8904392017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Heptadecyl-1,3-benzenediol GC-MS (2 TMS) - 70eV, Positivesplash10-00b9-9532300000-bf19d242220c6a1c2a042017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Heptadecyl-1,3-benzenediol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Heptadecyl-1,3-benzenediol 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 - 5-Heptadecyl-1,3-benzenediol 10V, Positive-QTOFsplash10-0002-0119000000-b6398e0c57ef84e311752016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Heptadecyl-1,3-benzenediol 20V, Positive-QTOFsplash10-002b-4894000000-d37e771201705766d43e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Heptadecyl-1,3-benzenediol 40V, Positive-QTOFsplash10-052f-8591000000-f747f4616c1ca2eba49e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Heptadecyl-1,3-benzenediol 10V, Negative-QTOFsplash10-0002-0009000000-2cf6b2642f5e5530239a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Heptadecyl-1,3-benzenediol 20V, Negative-QTOFsplash10-0002-0009000000-89a27fd58f54720b53af2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Heptadecyl-1,3-benzenediol 40V, Negative-QTOFsplash10-0ae9-2869000000-330ae90be36002cdc7ea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Heptadecyl-1,3-benzenediol 10V, Negative-QTOFsplash10-0002-0009000000-9951fbdc6c5a0edd22592021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Heptadecyl-1,3-benzenediol 20V, Negative-QTOFsplash10-0002-0009000000-2aa1f1f009d054844e782021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Heptadecyl-1,3-benzenediol 40V, Negative-QTOFsplash10-00dr-4943000000-9e92bec88cf67476a4ab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Heptadecyl-1,3-benzenediol 10V, Positive-QTOFsplash10-0002-1019000000-45d744025c9ae439309c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Heptadecyl-1,3-benzenediol 20V, Positive-QTOFsplash10-0002-7559000000-7f6bb7b747b6edea51c22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Heptadecyl-1,3-benzenediol 40V, Positive-QTOFsplash10-052f-9200000000-19b8f9e8b1b6e3fd1fa72021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.0109 +/- 0.00610 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.00505 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.0053 uMAdult (>18 years old)Both
Normal
details
BloodDetected and Quantified0.00920 +/- 0.00430 uMAdult (>18 years old)Female
Normal
details
BloodDetected and Quantified0.005 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.006 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.006 uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.0105 +/- 0.00570 uMAdult (>18 years old)FemaleNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID692
FooDB IDFDB017915
KNApSAcK IDNot Available
Chemspider ID158044
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound181700
PDB IDNot Available
ChEBI ID145967
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .