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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:25 UTC
Update Date2022-03-07 02:52:43 UTC
HMDB IDHMDB0030854
Secondary Accession Numbers
  • HMDB30854
Metabolite Identification
Common Name(S)-Auraptenol
Description(S)-Auraptenol belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one) (S)-Auraptenol has been detected, but not quantified in, sweet oranges (Citrus sinensis). This could make (S)-auraptenol a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on (S)-Auraptenol.
Structure
Data?1563862048
Synonyms
ValueSource
AuraptenolMeSH
Chemical FormulaC15H16O4
Average Molecular Weight260.2851
Monoisotopic Molecular Weight260.104859
IUPAC Name8-(2-hydroxy-3-methylbut-3-en-1-yl)-7-methoxy-2H-chromen-2-one
Traditional Name8-(2-hydroxy-3-methylbut-3-en-1-yl)-7-methoxychromen-2-one
CAS Registry Number1221-43-8
SMILES
COC1=C(CC(O)C(C)=C)C2=C(C=CC(=O)O2)C=C1
InChI Identifier
InChI=1S/C15H16O4/c1-9(2)12(16)8-11-13(18-3)6-4-10-5-7-14(17)19-15(10)11/h4-7,12,16H,1,8H2,2-3H3
InChI KeySQSRYWNOKPJENY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Alcohol
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • 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 Point109 - 110 °CNot Available
Boiling Point446.73 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility504.3 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.235 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP1.95ALOGPS
logP2.18ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)14.4ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.7 m³·mol⁻¹ChemAxon
Polarizability27.17 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]+159.43731661259
DarkChem[M-H]-159.34731661259
DeepCCS[M+H]+166.81530932474
DeepCCS[M-H]-164.45830932474
DeepCCS[M-2H]-197.34430932474
DeepCCS[M+Na]+172.90930932474
AllCCS[M+H]+159.132859911
AllCCS[M+H-H2O]+155.332859911
AllCCS[M+NH4]+162.632859911
AllCCS[M+Na]+163.732859911
AllCCS[M-H]-162.232859911
AllCCS[M+Na-2H]-162.032859911
AllCCS[M+HCOO]-161.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-AuraptenolCOC1=C(CC(O)C(C)=C)C2=C(C=CC(=O)O2)C=C13095.7Standard polar33892256
(S)-AuraptenolCOC1=C(CC(O)C(C)=C)C2=C(C=CC(=O)O2)C=C12236.5Standard non polar33892256
(S)-AuraptenolCOC1=C(CC(O)C(C)=C)C2=C(C=CC(=O)O2)C=C12293.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-Auraptenol,1TMS,isomer #1C=C(C)C(CC1=C(OC)C=CC2=C1OC(=O)C=C2)O[Si](C)(C)C2262.8Semi standard non polar33892256
(S)-Auraptenol,1TBDMS,isomer #1C=C(C)C(CC1=C(OC)C=CC2=C1OC(=O)C=C2)O[Si](C)(C)C(C)(C)C2516.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Auraptenol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9660000000-a4f2c9023842a06d8dcf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Auraptenol GC-MS (1 TMS) - 70eV, Positivesplash10-0076-9551000000-3e86f74ff09eeffab5492017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-Auraptenol 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 - (S)-Auraptenol , positive-QTOFsplash10-001r-0910000000-662f2f1cc2095028273d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Auraptenol , positive-QTOFsplash10-0019-0910000000-5e7039d4fb161baaee2f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (S)-Auraptenol , positive-QTOFsplash10-001c-0930000000-bdb207ffa052782e4c652017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Auraptenol 10V, Positive-QTOFsplash10-01ox-0090000000-8d516cd89de3a5c0e8892015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Auraptenol 20V, Positive-QTOFsplash10-006x-9150000000-69694ef12c68a49813182015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Auraptenol 40V, Positive-QTOFsplash10-00dl-9560000000-880f9122e164f9ba96112015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Auraptenol 10V, Negative-QTOFsplash10-0a4i-0190000000-a426b019748239d6aa202015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Auraptenol 20V, Negative-QTOFsplash10-056r-0790000000-2bfa6c766af259da968c2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Auraptenol 40V, Negative-QTOFsplash10-00sj-8930000000-233d1073f800d653738e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Auraptenol 10V, Negative-QTOFsplash10-0a4i-0190000000-0d14923dded6ed40c76c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Auraptenol 20V, Negative-QTOFsplash10-0929-4490000000-9ced2045f6dd65e0e8162021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Auraptenol 40V, Negative-QTOFsplash10-0092-3920000000-352c40feab0b1b5048e22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Auraptenol 10V, Positive-QTOFsplash10-01ox-0690000000-271563afd7d1c20a5f362021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Auraptenol 20V, Positive-QTOFsplash10-002u-6960000000-ee76e2f7ba222983847a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-Auraptenol 40V, Positive-QTOFsplash10-099d-2900000000-479897eca0c873b501e62021-09-24Wishart 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 IDFDB002813
KNApSAcK IDNot Available
Chemspider ID10235598
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound13343540
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1637261
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
(S)-Auraptenol → {[1-(7-methoxy-2-oxo-2H-chromen-8-yl)-3-methylbut-3-en-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
(S)-Auraptenol → 3,4,5-trihydroxy-6-{[1-(7-methoxy-2-oxo-2H-chromen-8-yl)-3-methylbut-3-en-2-yl]oxy}oxane-2-carboxylic aciddetails