Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:38:47 UTC
Update Date2022-03-07 02:52:40 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 has been detected, but not quantified in, herbs and spices. This could make (R)-heraclenol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Heraclenol.
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point117 - 118 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+168.2531661259
DarkChem[M-H]-167.36831661259
DeepCCS[M+H]+166.17230932474
DeepCCS[M-H]-163.81430932474
DeepCCS[M-2H]-196.84330932474
DeepCCS[M+Na]+172.26630932474
AllCCS[M+H]+168.232859911
AllCCS[M+H-H2O]+164.832859911
AllCCS[M+NH4]+171.332859911
AllCCS[M+Na]+172.232859911
AllCCS[M-H]-172.432859911
AllCCS[M+Na-2H]-172.032859911
AllCCS[M+HCOO]-171.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(R)-HeraclenolCC(C)(O)C(O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C23696.9Standard polar33892256
(R)-HeraclenolCC(C)(O)C(O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C22554.4Standard non polar33892256
(R)-HeraclenolCC(C)(O)C(O)COC1=C2OC(=O)C=CC2=CC2=C1OC=C22709.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(R)-Heraclenol,1TMS,isomer #1CC(C)(O[Si](C)(C)C)C(O)COC1=C2OC=CC2=CC2=C1OC(=O)C=C22718.2Semi standard non polar33892256
(R)-Heraclenol,1TMS,isomer #2CC(C)(O)C(COC1=C2OC=CC2=CC2=C1OC(=O)C=C2)O[Si](C)(C)C2699.2Semi standard non polar33892256
(R)-Heraclenol,2TMS,isomer #1CC(C)(O[Si](C)(C)C)C(COC1=C2OC=CC2=CC2=C1OC(=O)C=C2)O[Si](C)(C)C2713.7Semi standard non polar33892256
(R)-Heraclenol,1TBDMS,isomer #1CC(C)(O[Si](C)(C)C(C)(C)C)C(O)COC1=C2OC=CC2=CC2=C1OC(=O)C=C22972.2Semi standard non polar33892256
(R)-Heraclenol,1TBDMS,isomer #2CC(C)(O)C(COC1=C2OC=CC2=CC2=C1OC(=O)C=C2)O[Si](C)(C)C(C)(C)C2961.8Semi standard non polar33892256
(R)-Heraclenol,2TBDMS,isomer #1CC(C)(O[Si](C)(C)C(C)(C)C)C(COC1=C2OC=CC2=CC2=C1OC(=O)C=C2)O[Si](C)(C)C(C)(C)C3204.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Heraclenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9140000000-00effd3606a3a93b19c62017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Heraclenol GC-MS (2 TMS) - 70eV, Positivesplash10-001i-9644600000-ba97ef6ea2f2909d3c082017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (R)-Heraclenol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Heraclenol , positive-QTOFsplash10-0udj-0980000000-2a9d336c59b7427c787d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Heraclenol , positive-QTOFsplash10-0udi-0690000000-1c26fc27ceded773623e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Heraclenol 10V, Positive-QTOFsplash10-0uxr-0090000000-4d8c75807d4194c90cf72021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Heraclenol 20V, Positive-QTOFsplash10-0udi-2190000000-189cf5b0ff180b30a9312021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (R)-Heraclenol 40V, Positive-QTOFsplash10-0002-3910000000-45458632ebeb4baa67f62021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Heraclenol 10V, Positive-QTOFsplash10-0a4r-1079000000-5119de69b212b99ecdc92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Heraclenol 20V, Positive-QTOFsplash10-0k9i-4292000000-6e174f1e87ddc2795f452016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Heraclenol 40V, Positive-QTOFsplash10-0udr-8590000000-39ec641aaebce3f7a37c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Heraclenol 10V, Negative-QTOFsplash10-0udi-1198000000-db757ffc17838cf047272016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Heraclenol 20V, Negative-QTOFsplash10-0udi-0390000000-7d8b88d917de246f56592016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Heraclenol 40V, Negative-QTOFsplash10-0a4i-0910000000-d57b4f343ba87a8aa1bd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Heraclenol 10V, Negative-QTOFsplash10-0udi-0019000000-cd51f5d9186655cf2f112021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Heraclenol 20V, Negative-QTOFsplash10-0uxu-3191000000-1dc4aa373094d670f4a42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Heraclenol 40V, Negative-QTOFsplash10-0uk9-0490000000-3d798eaf31ebdd35d69e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Heraclenol 10V, Positive-QTOFsplash10-0zfr-0095000000-c1fc5235bb39ff83f6e92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Heraclenol 20V, Positive-QTOFsplash10-0udi-2190000000-c48273e3db9dd4283b562021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (R)-Heraclenol 40V, Positive-QTOFsplash10-052b-3940000000-452da60eb625532848ff2021-09-22Wishart LabView Spectrum
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
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 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