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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:31:02 UTC
Update Date2022-03-07 02:52:12 UTC
HMDB IDHMDB0029539
Secondary Accession Numbers
  • HMDB29539
Metabolite Identification
Common NameXenognosin A
DescriptionXenognosin A belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups. Xenognosin A has been detected, but not quantified in, common peas (Pisum sativum) and pulses. This could make xenognosin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Xenognosin A.
Structure
Data?1582753433
Synonyms
ValueSource
1-(4-Hydroxyphenyl)-3-(4-hydroxy-2-methoxyphenyl)propeneHMDB
4-[3-(4-Hydroxyphenyl)-2-propenyl]-3-methoxyphenol, 9ciHMDB
Chemical FormulaC16H16O3
Average Molecular Weight256.2964
Monoisotopic Molecular Weight256.109944378
IUPAC Name4-[(2E)-3-(4-hydroxyphenyl)prop-2-en-1-yl]-3-methoxyphenol
Traditional Namexenognosin A
CAS Registry Number76907-79-4
SMILES
COC1=C(C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C1
InChI Identifier
InChI=1S/C16H16O3/c1-19-16-11-15(18)10-7-13(16)4-2-3-12-5-8-14(17)9-6-12/h2-3,5-11,17-18H,4H2,1H3/b3-2+
InChI KeyLOHIEGDVOARVPJ-NSCUHMNNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cinnamylphenols. These are organic compounds containing the 1,3-diphenylpropene moiety with one benzene ring bearing one or more hydroxyl groups.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassLinear 1,3-diarylpropanoids
Sub ClassCinnamylphenols
Direct ParentCinnamylphenols
Alternative Parents
Substituents
  • Cinnamylphenol
  • Methoxyphenol
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Styrene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Ether
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.017 g/LALOGPS
logP3.6ALOGPS
logP3.91ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.19ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity76.54 m³·mol⁻¹ChemAxon
Polarizability28.17 ųChemAxon
Number of Rings2ChemAxon
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]+162.40831661259
DarkChem[M-H]-163.99431661259
DeepCCS[M+H]+169.3530932474
DeepCCS[M-H]-166.99230932474
DeepCCS[M-2H]-199.87930932474
DeepCCS[M+Na]+175.44330932474
AllCCS[M+H]+160.532859911
AllCCS[M+H-H2O]+156.532859911
AllCCS[M+NH4]+164.232859911
AllCCS[M+Na]+165.332859911
AllCCS[M-H]-162.032859911
AllCCS[M+Na-2H]-161.732859911
AllCCS[M+HCOO]-161.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Xenognosin ACOC1=C(C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C13964.7Standard polar33892256
Xenognosin ACOC1=C(C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C12496.9Standard non polar33892256
Xenognosin ACOC1=C(C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C12686.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Xenognosin A,1TMS,isomer #1COC1=CC(O)=CC=C1C/C=C/C1=CC=C(O[Si](C)(C)C)C=C12582.0Semi standard non polar33892256
Xenognosin A,1TMS,isomer #2COC1=CC(O[Si](C)(C)C)=CC=C1C/C=C/C1=CC=C(O)C=C12595.5Semi standard non polar33892256
Xenognosin A,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=CC=C1C/C=C/C1=CC=C(O[Si](C)(C)C)C=C12553.1Semi standard non polar33892256
Xenognosin A,1TBDMS,isomer #1COC1=CC(O)=CC=C1C/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C12867.1Semi standard non polar33892256
Xenognosin A,1TBDMS,isomer #2COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C/C=C/C1=CC=C(O)C=C12862.3Semi standard non polar33892256
Xenognosin A,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1C/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13103.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Xenognosin A GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a70-0970000000-d0a40bb2b68e689146182017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xenognosin A GC-MS (2 TMS) - 70eV, Positivesplash10-002r-2029000000-3baf463f93ccf9f227392017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Xenognosin A 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 - Xenognosin A 10V, Positive-QTOFsplash10-0a4i-0290000000-6551bc8bd8e7263d17b52016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin A 20V, Positive-QTOFsplash10-0a4i-0950000000-fae87a3a990d1e12f1e12016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin A 40V, Positive-QTOFsplash10-0lei-3910000000-34ccb435060b3671a20b2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin A 10V, Negative-QTOFsplash10-0a4i-0090000000-a91ec03b87b7bd054a8a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin A 20V, Negative-QTOFsplash10-0a4i-0190000000-fcad5288840af2e38a8b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin A 40V, Negative-QTOFsplash10-0a4l-2970000000-481901c933b24430dc262016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin A 10V, Positive-QTOFsplash10-0a4i-0690000000-0a12ace62666ad6ac55b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin A 20V, Positive-QTOFsplash10-0a4r-2920000000-45785fdd30c6b2a5c98a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin A 40V, Positive-QTOFsplash10-0ar0-2930000000-862356c1d6de46e75de82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin A 10V, Negative-QTOFsplash10-0a4i-0090000000-e382f8a0b4d1e3b6f4082021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin A 20V, Negative-QTOFsplash10-0a4i-0690000000-67d405e924a9dbe8d1d32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Xenognosin A 40V, Negative-QTOFsplash10-00kb-0900000000-744c2ae6c6f7407e9ef82021-09-24Wishart 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 IDFDB000682
KNApSAcK IDC00002390
Chemspider ID4444682
KEGG Compound IDC08731
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281296
PDB IDNot Available
ChEBI ID714392
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.. .

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
Xenognosin A → 3,4,5-trihydroxy-6-{4-[(1E)-3-(4-hydroxy-2-methoxyphenyl)prop-1-en-1-yl]phenoxy}oxane-2-carboxylic aciddetails
Xenognosin A → 3,4,5-trihydroxy-6-{4-[3-(4-hydroxyphenyl)prop-2-en-1-yl]-3-methoxyphenoxy}oxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
Xenognosin A → {4-[(1E)-3-(4-hydroxy-2-methoxyphenyl)prop-1-en-1-yl]phenyl}oxidanesulfonic aciddetails