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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:02 UTC
Update Date2022-03-07 02:52:41 UTC
HMDB IDHMDB0030788
Secondary Accession Numbers
  • HMDB30788
Metabolite Identification
Common NameCitrusal
DescriptionCitrusal 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). Based on a literature review very few articles have been published on Citrusal.
Structure
Data?1563862038
Synonyms
ValueSource
7-Methoxy-8-(2-formyl-2-methylpropyl)coumarinHMDB
8-(2,2-Dimethyl-3-oxopropyl)-7-methoxy-2H-1-benzopyran-2-one, 9ciHMDB
Morphine sulfate (anhydrous)HMDB
Morphine sulphate (anhydrous)HMDB
Chemical FormulaC15H16O4
Average Molecular Weight260.2851
Monoisotopic Molecular Weight260.104859
IUPAC Name3-(7-methoxy-2-oxo-2H-chromen-8-yl)-2,2-dimethylpropanal
Traditional Name3-(7-methoxy-2-oxochromen-8-yl)-2,2-dimethylpropanal
CAS Registry Number5980-07-4
SMILES
COC1=C(CC(C)(C)C=O)C2=C(C=CC(=O)O2)C=C1
InChI Identifier
InChI=1S/C15H16O4/c1-15(2,9-16)8-11-12(18-3)6-4-10-5-7-13(17)19-14(10)11/h4-7,9H,8H2,1-3H3
InChI KeyVCYVDHAWDPDCKW-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
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Aldehyde
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Organooxygen 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 Point137 - 138 °CNot Available
Boiling Point418.65 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility150.5 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.228 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.014 g/LALOGPS
logP2.7ALOGPS
logP2.65ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area52.6 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.07 m³·mol⁻¹ChemAxon
Polarizability26.91 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]+160.03631661259
DarkChem[M-H]-160.8431661259
DeepCCS[M+H]+168.33430932474
DeepCCS[M-H]-165.97630932474
DeepCCS[M-2H]-198.86230932474
DeepCCS[M+Na]+174.42730932474
AllCCS[M+H]+157.132859911
AllCCS[M+H-H2O]+153.332859911
AllCCS[M+NH4]+160.732859911
AllCCS[M+Na]+161.732859911
AllCCS[M-H]-162.632859911
AllCCS[M+Na-2H]-162.332859911
AllCCS[M+HCOO]-162.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CitrusalCOC1=C(CC(C)(C)C=O)C2=C(C=CC(=O)O2)C=C12864.9Standard polar33892256
CitrusalCOC1=C(CC(C)(C)C=O)C2=C(C=CC(=O)O2)C=C12179.9Standard non polar33892256
CitrusalCOC1=C(CC(C)(C)C=O)C2=C(C=CC(=O)O2)C=C12173.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citrusal GC-MS (Non-derivatized) - 70eV, Positivesplash10-003s-3590000000-b8baf4c20c82d80718312017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrusal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrusal 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 - Citrusal 10V, Positive-QTOFsplash10-03di-0090000000-81a5d4c2650e11b1303a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusal 20V, Positive-QTOFsplash10-03di-1090000000-b068b8d4c13be2af44972015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusal 40V, Positive-QTOFsplash10-0g5c-5980000000-ed70c534a6372c60f3062015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusal 10V, Negative-QTOFsplash10-0a4i-0090000000-a61e29c0a847fdab86982015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusal 20V, Negative-QTOFsplash10-0a4i-0090000000-b57d2d806e3f0cc265f22015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusal 40V, Negative-QTOFsplash10-014j-9760000000-ee2a06d185d10f8b2d792015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusal 10V, Negative-QTOFsplash10-0a4i-0090000000-1048deeca0eebbf134482021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusal 20V, Negative-QTOFsplash10-0a4i-0490000000-93582fca3e3c14b5999b2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusal 40V, Negative-QTOFsplash10-0229-0910000000-a7409ba6abb70a6dcf252021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusal 10V, Positive-QTOFsplash10-03du-0950000000-6208d893a59d744e9de32021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusal 20V, Positive-QTOFsplash10-000i-0910000000-c71eb85b8e8edfaeb9232021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrusal 40V, Positive-QTOFsplash10-06y6-3910000000-d5da9e4f0a5a55a8d1692021-09-25Wishart 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 IDFDB002726
KNApSAcK IDC00054444
Chemspider ID4477732
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5319433
PDB IDNot Available
ChEBI ID174411
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1637241
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 oxidoreductase activity
Specific function:
NADPH-dependent reductase with broad substrate specificity. Catalyzes the reduction of a wide variety of carbonyl compounds including quinones, prostaglandins, menadione, plus various xenobiotics. Catalyzes the reduction of the antitumor anthracyclines doxorubicin and daunorubicin to the cardiotoxic compounds doxorubicinol and daunorubicinol. Can convert prostaglandin E2 to prostaglandin F2-alpha. Can bind glutathione, which explains its higher affinity for glutathione-conjugated substrates. Catalyzes the reduction of S-nitrosoglutathione.
Gene Name:
CBR1
Uniprot ID:
P16152
Molecular weight:
30374.73
Reactions
Citrusal → 8-(3-hydroxy-2,2-dimethylpropyl)-7-methoxy-2H-chromen-2-onedetails
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
AOX1
Uniprot ID:
Q06278
Molecular weight:
147916.735
Reactions
Citrusal → 3-(7-methoxy-2-oxo-2H-chromen-8-yl)-2,2-dimethylpropanoic aciddetails