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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:47 UTC
Update Date2019-07-23 06:07:11 UTC
HMDB IDHMDB0030745
Secondary Accession Numbers
  • HMDB30745
Metabolite Identification
Common Name(R)-Heraclenol
Description(R)-Heraclenol belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one (R)-Heraclenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (R)-Heraclenol has been detected, but not quantified in, herbs and spices. This could make (R)-heraclenol a potential biomarker for the consumption of these foods.
Structure
Data?1563862031
Synonyms
ValueSource
HeraclenolHMDB
Chemical FormulaC16H16O6
Average Molecular Weight304.2946
Monoisotopic Molecular Weight304.094688244
IUPAC Name9-(2,3-dihydroxy-3-methylbutoxy)-7H-furo[3,2-g]chromen-7-one
Traditional Name9-(2,3-dihydroxy-3-methylbutoxy)furo[3,2-g]chromen-7-one
CAS Registry Number26091-76-9
SMILES
CC(C)(O)C(O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C2
InChI Identifier
InChI=1S/C16H16O6/c1-16(2,19)11(17)8-21-15-13-10(5-6-20-13)7-9-3-4-12(18)22-14(9)15/h3-7,11,17,19H,8H2,1-2H3
InChI KeyFOINLJRVEBYARJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as psoralens. These are organic compounds containing a psoralen moiety, which consists of a furan fused to a chromenone to for 7H-furo[3,2-g]chromen-7-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassFuranocoumarins
Direct ParentPsoralens
Alternative Parents
Substituents
  • Psoralen
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Tertiary alcohol
  • Furan
  • 1,2-diol
  • Secondary alcohol
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point117 - 118 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP1.82ALOGPS
logP1.16ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)13.2ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity78.16 m³·mol⁻¹ChemAxon
Polarizability30.5 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9140000000-00effd3606a3a93b19c6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-001i-9644600000-ba97ef6ea2f2909d3c08Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udj-0980000000-2a9d336c59b7427c787dSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0udi-0690000000-1c26fc27ceded773623eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-1079000000-5119de69b212b99ecdc9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-4292000000-6e174f1e87ddc2795f45Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udr-8590000000-39ec641aaebce3f7a37cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1198000000-db757ffc17838cf04727Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0390000000-7d8b88d917de246f5659Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-0910000000-d57b4f343ba87a8aa1bdSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB002674
KNApSAcK IDNot Available
Chemspider ID290709
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound328236
PDB IDNot Available
ChEBI ID93899
Food Biomarker OntologyNot Available
VMH 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 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
(R)-Heraclenol → {[3-hydroxy-3-methyl-1-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)butan-2-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
(R)-Heraclenol → 3,4,5-trihydroxy-6-{[3-hydroxy-3-methyl-1-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)butan-2-yl]oxy}oxane-2-carboxylic aciddetails
(R)-Heraclenol → 3,4,5-trihydroxy-6-{[3-hydroxy-2-methyl-4-({7-oxo-7H-furo[3,2-g]chromen-9-yl}oxy)butan-2-yl]oxy}oxane-2-carboxylic aciddetails