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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:07 UTC
Update Date2022-03-07 02:52:42 UTC
HMDB IDHMDB0030801
Secondary Accession Numbers
  • HMDB30801
Metabolite Identification
Common Name1-(4-Hydroxy-3-methoxyphenyl)-3-decanone
Description1-(4-Hydroxy-3-methoxyphenyl)-3-decanone is found in alcoholic beverages. 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone is from grains of paradise (Amomum melegueta) and ginger (Zingiber officinale).Paradol is the active flavor constituent of the seeds of Guinea pepper (Aframomum melegueta). The seed is also known as Grains of paradise. Paradol has been found to have antioxidative and antitumor promoting effects. It is used in flavors as an essential oil to give spiciness. (Wikipedia
Structure
Data?1563862040
Synonyms
ValueSource
(6)-ParadolMeSH
1-(4'-Hydroxy-3'-methoxyphenyl)-3-decanoneMeSH
6-ParadolMeSH
Heptyl 4-hydroxy-3-methoxyphenethyl ketoneHMDB
[6]-GingeroneHMDB
[6]-ParadolHMDB
Chemical FormulaC17H26O3
Average Molecular Weight278.3865
Monoisotopic Molecular Weight278.188194698
IUPAC Name1-(4-hydroxy-3-methoxyphenyl)decan-3-one
Traditional Nameparadol
CAS Registry Number27113-22-0
SMILES
CCCCCCCC(=O)CCC1=CC(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C17H26O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h10,12-13,19H,3-9,11H2,1-2H3
InChI KeyCZNLTCTYLMYLHL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as paradols. Paradols are compounds containing a paradol moiety, which is consists of a benzene ring with a decan-3-one moiety, a methoxyl group, and a hydroxyl group at positions 1,3, and 4 respectively.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassMethoxyphenols
Direct ParentParadols
Alternative Parents
Substituents
  • Paradol
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ketone
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point31 - 32 °CNot Available
Boiling Point406.00 to 408.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility3.8 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.225 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP4.89ALOGPS
logP4.85ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)9.95ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity81.59 m³·mol⁻¹ChemAxon
Polarizability33.25 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]+171.75631661259
DarkChem[M-H]-171.75431661259
DeepCCS[M+H]+176.17230932474
DeepCCS[M-H]-173.81430932474
DeepCCS[M-2H]-206.730932474
DeepCCS[M+Na]+182.26630932474
AllCCS[M+H]+172.032859911
AllCCS[M+H-H2O]+168.732859911
AllCCS[M+NH4]+175.132859911
AllCCS[M+Na]+176.032859911
AllCCS[M-H]-174.732859911
AllCCS[M+Na-2H]-175.632859911
AllCCS[M+HCOO]-176.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-(4-Hydroxy-3-methoxyphenyl)-3-decanoneCCCCCCCC(=O)CCC1=CC(OC)=C(O)C=C13599.4Standard polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanoneCCCCCCCC(=O)CCC1=CC(OC)=C(O)C=C12182.6Standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanoneCCCCCCCC(=O)CCC1=CC(OC)=C(O)C=C12228.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,1TMS,isomer #1CCCCCCCC(=O)CCC1=CC=C(O[Si](C)(C)C)C(OC)=C12298.0Semi standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,1TMS,isomer #2CCCCCCCC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2394.7Semi standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,1TMS,isomer #3CCCCCCC=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C2361.5Semi standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,2TMS,isomer #1CCCCCCCC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2444.6Semi standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,2TMS,isomer #1CCCCCCCC(=CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2363.3Standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,2TMS,isomer #2CCCCCCC=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2385.3Semi standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,2TMS,isomer #2CCCCCCC=C(CCC1=CC=C(O[Si](C)(C)C)C(OC)=C1)O[Si](C)(C)C2335.0Standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,1TBDMS,isomer #1CCCCCCCC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C12547.5Semi standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,1TBDMS,isomer #2CCCCCCCC(=CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C2631.3Semi standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,1TBDMS,isomer #3CCCCCCC=C(CCC1=CC=C(O)C(OC)=C1)O[Si](C)(C)C(C)(C)C2609.2Semi standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,2TBDMS,isomer #1CCCCCCCC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C2923.8Semi standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,2TBDMS,isomer #1CCCCCCCC(=CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C2788.5Standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,2TBDMS,isomer #2CCCCCCC=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C2847.9Semi standard non polar33892256
1-(4-Hydroxy-3-methoxyphenyl)-3-decanone,2TBDMS,isomer #2CCCCCCC=C(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1)O[Si](C)(C)C(C)(C)C2741.5Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-5910000000-f2cc89b62742f866e1b82017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone GC-MS (1 TMS) - 70eV, Positivesplash10-0udi-6192000000-e47146113e8388a675c42017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 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 - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 10V, Positive-QTOFsplash10-004i-0190000000-3e82563bcd19cbc7e7a82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 20V, Positive-QTOFsplash10-004r-6930000000-25e6c207caaeefb5e9732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 40V, Positive-QTOFsplash10-052f-9500000000-57ef68cf2db562646b8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 10V, Negative-QTOFsplash10-004i-0190000000-1ad40bde2a15e9b3ac672016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 20V, Negative-QTOFsplash10-004i-1980000000-cd9e0c355c37164900932016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 40V, Negative-QTOFsplash10-0553-4910000000-785a047bd1bc99289e532016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 10V, Negative-QTOFsplash10-004i-0090000000-dbaf79a4688908a5ba102021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 20V, Negative-QTOFsplash10-0006-3910000000-1cf1f456ef0428b559ec2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 40V, Negative-QTOFsplash10-05a6-9600000000-709113ddcaec828613052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 10V, Positive-QTOFsplash10-01ti-0690000000-04e967cf4ec12b7d71062021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 20V, Positive-QTOFsplash10-01p9-3930000000-eebad90f323183b69f302021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-(4-Hydroxy-3-methoxyphenyl)-3-decanone 40V, Positive-QTOFsplash10-0zg0-4900000000-ca89f9f474328c25e58f2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB002743
KNApSAcK IDC00002764
Chemspider ID85173
KEGG Compound IDC10482
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound94378
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1103061
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.. .