Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:16:25 UTC
Update Date2022-03-07 02:53:45 UTC
HMDB IDHMDB0033536
Secondary Accession Numbers
  • HMDB33536
Metabolite Identification
Common NameHonyucitrin
DescriptionHonyucitrin belongs to the class of organic compounds known as 3'-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3'-position. Thus, honyucitrin is considered to be a flavonoid. Honyucitrin has been detected, but not quantified in, citrus and pummelos (Citrus maxima). This could make honyucitrin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Honyucitrin.
Structure
Data?1563862421
Synonyms
ValueSource
5,7-Dihydroxy-2-[4-hydroxy-3,5-bis(3-methyl-2-butenyl)phenyl]-4H-1-benzopyran-4-one, 9ciHMDB
Chemical FormulaC25H26O5
Average Molecular Weight406.4709
Monoisotopic Molecular Weight406.178023942
IUPAC Name5,7-dihydroxy-2-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]-4H-chromen-4-one
Traditional Namehonyucitrin
CAS Registry Number114542-44-8
SMILES
CC(C)=CCC1=CC(=CC(CC=C(C)C)=C1O)C1=CC(=O)C2=C(O)C=C(O)C=C2O1
InChI Identifier
InChI=1S/C25H26O5/c1-14(2)5-7-16-9-18(10-17(25(16)29)8-6-15(3)4)22-13-21(28)24-20(27)11-19(26)12-23(24)30-22/h5-6,9-13,26-27,29H,7-8H2,1-4H3
InChI KeyDOFKPAVSYGZVQD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3'-prenylated flavones. These are flavones that features a C5-isoprenoid substituent at the 3'-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct Parent3'-prenylated flavones
Alternative Parents
Substituents
  • 3'-prenylated flavone
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point199.5 - 201 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0038 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0025 g/LALOGPS
logP5.15ALOGPS
logP6.16ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)6.63ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.99 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity121.4 m³·mol⁻¹ChemAxon
Polarizability45.99 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+196.87230932474
DeepCCS[M-H]-194.51430932474
DeepCCS[M-2H]-228.42930932474
DeepCCS[M+Na]+203.91830932474
AllCCS[M+H]+199.532859911
AllCCS[M+H-H2O]+196.732859911
AllCCS[M+NH4]+202.032859911
AllCCS[M+Na]+202.732859911
AllCCS[M-H]-195.832859911
AllCCS[M+Na-2H]-195.432859911
AllCCS[M+HCOO]-195.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
HonyucitrinCC(C)=CCC1=CC(=CC(CC=C(C)C)=C1O)C1=CC(=O)C2=C(O)C=C(O)C=C2O15532.2Standard polar33892256
HonyucitrinCC(C)=CCC1=CC(=CC(CC=C(C)C)=C1O)C1=CC(=O)C2=C(O)C=C(O)C=C2O13582.4Standard non polar33892256
HonyucitrinCC(C)=CCC1=CC(=CC(CC=C(C)C)=C1O)C1=CC(=O)C2=C(O)C=C(O)C=C2O13842.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Honyucitrin,1TMS,isomer #1CC(C)=CCC1=CC(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)=CC(CC=C(C)C)=C1O[Si](C)(C)C3846.9Semi standard non polar33892256
Honyucitrin,1TMS,isomer #2CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC(CC=C(C)C)=C1O3891.6Semi standard non polar33892256
Honyucitrin,1TMS,isomer #3CC(C)=CCC1=CC(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC(CC=C(C)C)=C1O3958.7Semi standard non polar33892256
Honyucitrin,2TMS,isomer #1CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O)C=C3O2)=CC(CC=C(C)C)=C1O[Si](C)(C)C3725.2Semi standard non polar33892256
Honyucitrin,2TMS,isomer #2CC(C)=CCC1=CC(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C=C3O2)=CC(CC=C(C)C)=C1O[Si](C)(C)C3783.0Semi standard non polar33892256
Honyucitrin,2TMS,isomer #3CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC(CC=C(C)C)=C1O3844.4Semi standard non polar33892256
Honyucitrin,3TMS,isomer #1CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O2)=CC(CC=C(C)C)=C1O[Si](C)(C)C3738.8Semi standard non polar33892256
Honyucitrin,1TBDMS,isomer #1CC(C)=CCC1=CC(C2=CC(=O)C3=C(O)C=C(O)C=C3O2)=CC(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C4087.2Semi standard non polar33892256
Honyucitrin,1TBDMS,isomer #2CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC(CC=C(C)C)=C1O4136.3Semi standard non polar33892256
Honyucitrin,1TBDMS,isomer #3CC(C)=CCC1=CC(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC(CC=C(C)C)=C1O4198.8Semi standard non polar33892256
Honyucitrin,2TBDMS,isomer #1CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O2)=CC(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C4218.4Semi standard non polar33892256
Honyucitrin,2TBDMS,isomer #2CC(C)=CCC1=CC(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C4275.0Semi standard non polar33892256
Honyucitrin,2TBDMS,isomer #3CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC(CC=C(C)C)=C1O4326.6Semi standard non polar33892256
Honyucitrin,3TBDMS,isomer #1CC(C)=CCC1=CC(C2=CC(=O)C3=C(O[Si](C)(C)C(C)(C)C)C=C(O[Si](C)(C)C(C)(C)C)C=C3O2)=CC(CC=C(C)C)=C1O[Si](C)(C)C(C)(C)C4421.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Honyucitrin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-3209000000-a4fe2da6bb38f94691232017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Honyucitrin GC-MS (3 TMS) - 70eV, Positivesplash10-0a4i-2000059000-67de2f4d5434dceec3c02017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Honyucitrin 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 - Honyucitrin 10V, Positive-QTOFsplash10-0a4i-1005900000-72fc2aa5b682b9b3e7b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Honyucitrin 20V, Positive-QTOFsplash10-0pvr-4009300000-1d798f6fc28d29dc24462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Honyucitrin 40V, Positive-QTOFsplash10-01b9-9414000000-2050e741db2e76f678542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Honyucitrin 10V, Negative-QTOFsplash10-0a4i-0000900000-fecff04ef980ba654da22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Honyucitrin 20V, Negative-QTOFsplash10-0a4i-0003900000-9dce50cb863122c741df2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Honyucitrin 40V, Negative-QTOFsplash10-08gr-3329000000-998ed87e106da57b589a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Honyucitrin 10V, Negative-QTOFsplash10-0a4i-0000900000-4beb10611eb4ba1142872021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Honyucitrin 20V, Negative-QTOFsplash10-0a4i-0000900000-881a9d71e0d8ed60c7e02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Honyucitrin 40V, Negative-QTOFsplash10-0k92-0794300000-d9ce3f8475e4ec79ed9e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Honyucitrin 10V, Positive-QTOFsplash10-0a4i-0000900000-18eb98d75246f8994f012021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Honyucitrin 20V, Positive-QTOFsplash10-0a4i-0000900000-18eb98d75246f8994f012021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Honyucitrin 40V, Positive-QTOFsplash10-0pb9-0941600000-4efb2ef881063c8df61f2021-09-25Wishart 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 IDFDB011596
KNApSAcK IDC00004019
Chemspider ID24843463
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44257865
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1836501
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
Honyucitrin → 3,4,5-trihydroxy-6-({5-hydroxy-2-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]-4-oxo-4H-chromen-7-yl}oxy)oxane-2-carboxylic aciddetails
Honyucitrin → 3,4,5-trihydroxy-6-({7-hydroxy-2-[4-hydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]-4-oxo-4H-chromen-5-yl}oxy)oxane-2-carboxylic aciddetails
Honyucitrin → 6-[4-(5,7-dihydroxy-4-oxo-4H-chromen-2-yl)-2,6-bis(3-methylbut-2-en-1-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails