Hmdb loader
Show more...Show more...Show more...Show more...
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:33:07 UTC
Update Date2023-02-21 17:19:19 UTC
HMDB IDHMDB0029865
Secondary Accession Numbers
  • HMDB29865
Metabolite Identification
Common NameUmbelliferone
DescriptionUmbelliferone, also known as 7-hydroxycoumarin or hydrangin, belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Umbelliferone is found, on average, in the highest concentration within anises (Pimpinella anisum) and beer. Umbelliferone has also been detected, but not quantified in, several different foods, such as nopals (Opuntia cochenillifera), nanking cherries (Prunus tomentosa), mamey sapotes (Pouteria sapota), japanese persimmons (Diospyros kaki), and chinese broccolis (Brassica alboglabra). This could make umbelliferone a potential biomarker for the consumption of these foods. Umbelliferone is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Umbelliferone.
Structure
Thumb
Synonyms
Chemical FormulaC9H6O3
Average Molecular Weight162.144
Monoisotopic Molecular Weight162.031694053
IUPAC Name7-hydroxy-2H-chromen-2-one
Traditional Nameumbelliferone
CAS Registry Number93-35-6
SMILES
OC1=CC2=C(C=C1)C=CC(=O)O2
InChI Identifier
InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
InChI KeyORHBXUUXSCNDEV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent7-hydroxycoumarins
Alternative Parents
Substituents
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point230 - 232 °CNot Available
Boiling Point382.08 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility11380 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.580 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker130.56530932474
[M-H]-Not Available130.565http://allccs.zhulab.cn/database/detail?ID=AllCCS00001940
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified0.13 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID641
FooDB IDFDB001094
KNApSAcK IDC00002503
Chemspider ID4444774
KEGG Compound IDC09315
BioCyc IDCPD-8186
BiGG IDNot Available
Wikipedia LinkUmbelliferone
METLIN IDNot Available
PubChem Compound5281426
PDB ID07L
ChEBI ID27510
Food Biomarker OntologyNot Available
VMH IDHCOUMARIN
MarkerDB IDNot Available
Good Scents IDrw1027521
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gok E: Investigation of binding properties of umbelliferone (7hydroxycoumarin) to lysozyme. J Fluoresc. 2013 Mar;23(2):333-8. doi: 10.1007/s10895-012-1151-0. Epub 2012 Dec 8. [PubMed:23224618 ]
  2. (). 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
Umbelliferone → 3,4,5-trihydroxy-6-[(2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic aciddetails