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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:28:03 UTC
Update Date2022-03-07 02:53:49 UTC
HMDB IDHMDB0033711
Secondary Accession Numbers
  • HMDB33711
Metabolite Identification
Common Name5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone
Description5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone has been detected, but not quantified in, herbs and spices. This could make 5-hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone.
Structure
Data?1563862448
SynonymsNot Available
Chemical FormulaC19H22O3
Average Molecular Weight298.3762
Monoisotopic Molecular Weight298.15689457
IUPAC Name5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one
Traditional Name5-hydroxy-7-(4-hydroxyphenyl)-1-phenylheptan-3-one
CAS Registry Number83161-96-0
SMILES
OC(CCC1=CC=C(O)C=C1)CC(=O)CCC1=CC=CC=C1
InChI Identifier
InChI=1S/C19H22O3/c20-17-10-6-16(7-11-17)9-13-19(22)14-18(21)12-8-15-4-2-1-3-5-15/h1-7,10-11,19-20,22H,8-9,12-14H2
InChI KeyUNMNJFPAJOHXMT-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassDiarylheptanoids
Sub ClassLinear diarylheptanoids
Direct ParentLinear diarylheptanoids
Alternative Parents
Substituents
  • Linear 1,7-diphenylheptane skeleton
  • Fatty alcohol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Beta-hydroxy ketone
  • Fatty acyl
  • Benzenoid
  • Secondary alcohol
  • Ketone
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility330 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.029 g/LALOGPS
logP3.47ALOGPS
logP4.02ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)10.3ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity87.54 m³·mol⁻¹ChemAxon
Polarizability33.86 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]+172.12831661259
DarkChem[M-H]-168.58631661259
DeepCCS[M+H]+169.95430932474
DeepCCS[M-H]-167.59630932474
DeepCCS[M-2H]-200.48230932474
DeepCCS[M+Na]+176.04730932474
AllCCS[M+H]+176.232859911
AllCCS[M+H-H2O]+172.732859911
AllCCS[M+NH4]+179.632859911
AllCCS[M+Na]+180.532859911
AllCCS[M-H]-177.532859911
AllCCS[M+Na-2H]-177.832859911
AllCCS[M+HCOO]-178.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanoneOC(CCC1=CC=C(O)C=C1)CC(=O)CCC1=CC=CC=C14143.2Standard polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanoneOC(CCC1=CC=C(O)C=C1)CC(=O)CCC1=CC=CC=C12672.9Standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanoneOC(CCC1=CC=C(O)C=C1)CC(=O)CCC1=CC=CC=C12737.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,1TMS,isomer #1C[Si](C)(C)OC(CCC1=CC=C(O)C=C1)CC(=O)CCC1=CC=CC=C12727.4Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,1TMS,isomer #2C[Si](C)(C)OC1=CC=C(CCC(O)CC(=O)CCC2=CC=CC=C2)C=C12744.4Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,1TMS,isomer #3C[Si](C)(C)OC(=CCC1=CC=CC=C1)CC(O)CCC1=CC=C(O)C=C12880.9Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,1TMS,isomer #4C[Si](C)(C)OC(=CC(O)CCC1=CC=C(O)C=C1)CCC1=CC=CC=C12852.2Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(CCC(CC(=O)CCC2=CC=CC=C2)O[Si](C)(C)C)C=C12689.6Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,2TMS,isomer #2C[Si](C)(C)OC(=CCC1=CC=CC=C1)CC(CCC1=CC=C(O)C=C1)O[Si](C)(C)C2842.8Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,2TMS,isomer #3C[Si](C)(C)OC(=CC(CCC1=CC=C(O)C=C1)O[Si](C)(C)C)CCC1=CC=CC=C12818.5Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,2TMS,isomer #4C[Si](C)(C)OC(=CCC1=CC=CC=C1)CC(O)CCC1=CC=C(O[Si](C)(C)C)C=C12832.1Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,2TMS,isomer #5C[Si](C)(C)OC(=CC(O)CCC1=CC=C(O[Si](C)(C)C)C=C1)CCC1=CC=CC=C12793.6Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,3TMS,isomer #1C[Si](C)(C)OC(=CCC1=CC=CC=C1)CC(CCC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C2810.2Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,3TMS,isomer #1C[Si](C)(C)OC(=CCC1=CC=CC=C1)CC(CCC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C2602.7Standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,3TMS,isomer #2C[Si](C)(C)OC(=CC(CCC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C)CCC1=CC=CC=C12766.5Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,3TMS,isomer #2C[Si](C)(C)OC(=CC(CCC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C)CCC1=CC=CC=C12552.9Standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CCC1=CC=C(O)C=C1)CC(=O)CCC1=CC=CC=C12978.4Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(O)CC(=O)CCC2=CC=CC=C2)C=C12999.2Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CCC1=CC=CC=C1)CC(O)CCC1=CC=C(O)C=C13124.6Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CC(O)CCC1=CC=C(O)C=C1)CCC1=CC=CC=C13082.7Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(CCC(CC(=O)CCC2=CC=CC=C2)O[Si](C)(C)C(C)(C)C)C=C13171.2Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CCC1=CC=CC=C1)CC(CCC1=CC=C(O)C=C1)O[Si](C)(C)C(C)(C)C3320.9Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=CC(CCC1=CC=C(O)C=C1)O[Si](C)(C)C(C)(C)C)CCC1=CC=CC=C13305.1Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC(=CCC1=CC=CC=C1)CC(O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C13314.9Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC(=CC(O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)CCC1=CC=CC=C13276.0Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=CCC1=CC=CC=C1)CC(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C3514.3Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=CCC1=CC=CC=C1)CC(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C3198.3Standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CC(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C)CCC1=CC=CC=C13479.3Semi standard non polar33892256
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=CC(CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C)CCC1=CC=CC=C13129.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-1900000000-d9f0175e6daac5e687412017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone GC-MS (2 TMS) - 70eV, Positivesplash10-0563-5934200000-7b3c19ab37f35dfc2ede2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 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-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 10V, Positive-QTOFsplash10-001j-0390000000-e54e2ed8df589a0f59682015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 20V, Positive-QTOFsplash10-001i-1910000000-3c8307f77fee0c98ba482015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 40V, Positive-QTOFsplash10-0a5c-3900000000-22ae9417133b7ab2fea12015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 10V, Negative-QTOFsplash10-0002-0390000000-1622f061aa6e5fe2434a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 20V, Negative-QTOFsplash10-0002-0930000000-dda62d334564b1ec88dc2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 40V, Negative-QTOFsplash10-052e-5900000000-a60f2f88b27bc31078722015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 10V, Negative-QTOFsplash10-0002-0290000000-4f98865cb06d3c2f1c042021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 20V, Negative-QTOFsplash10-005a-1960000000-aea00cf184c17cf277e22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 40V, Negative-QTOFsplash10-00mo-7910000000-27190c1d49c45c3f2b9c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 10V, Positive-QTOFsplash10-01qa-0290000000-46240b78b1511e01b2672021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 20V, Positive-QTOFsplash10-0a4l-2910000000-1766a2ef275ee3e220b62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone 40V, Positive-QTOFsplash10-0a4i-3900000000-8fda3783d8e970f4dd0c2021-09-24Wishart 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 IDNot Available
FooDB IDFDB011827
KNApSAcK IDNot Available
Chemspider ID8215903
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10040339
PDB IDNot Available
ChEBI ID174841
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1837881
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 sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone → {[1-(4-hydroxyphenyl)-5-oxo-7-phenylheptan-3-yl]oxy}sulfonic aciddetails
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
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone → 3,4,5-trihydroxy-6-[4-(3-hydroxy-5-oxo-7-phenylheptyl)phenoxy]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
5-Hydroxy-7-(4-hydroxyphenyl)-1-phenyl-3-heptanone → [4-(3-hydroxy-5-oxo-7-phenylheptyl)phenyl]oxidanesulfonic aciddetails