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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:44:19 UTC
Update Date2022-03-07 02:57:13 UTC
HMDB IDHMDB0041857
Secondary Accession Numbers
  • HMDB41857
Metabolite Identification
Common NameCitrinin
DescriptionCitrinin is a mycotoxin originally isolated from Penicillium citrinum. It has since been found to be produced by a variety of other fungi which are found or used in the production of human foods, such as grain, cheese, sake and red pigments. Citrinin has also been found in commercial red yeast rice supplements, and also in Aspergillus niveus and Aspergillus terreus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987).
Structure
Data?1563863708
Synonyms
ValueSource
(3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acidChEBI
(3R-trans)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylic acidChEBI
(3R,4S)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylateGenerator
(3R-trans)-4,6-Dihydro-8-hydroxy-3,4,5-trimethyl-6-oxo-3H-2-benzopyran-7-carboxylateGenerator
(3R,4S)-8-Hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-isochromene-7-carboxylic acidHMDB
AntimycinHMDB
CitriainHMDB
CitrininChEBI
Chemical FormulaC13H14O5
Average Molecular Weight250.2473
Monoisotopic Molecular Weight250.084123558
IUPAC Name(3R,4S)-8-hydroxy-3,4,5-trimethyl-6-oxo-4,6-dihydro-3H-2-benzopyran-7-carboxylic acid
Traditional Nameantimycin
CAS Registry Number518-75-2
SMILES
[H][C@]1(C)OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@]1([H])C
InChI Identifier
InChI=1S/C13H14O5/c1-5-7(3)18-4-8-9(5)6(2)11(14)10(12(8)15)13(16)17/h4-5,7,15H,1-3H3,(H,16,17)/t5-,7-/m1/s1
InChI KeyCQIUKKVOEOPUDV-IYSWYEEDSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzopyrans
Sub ClassNot Available
Direct ParentBenzopyrans
Alternative Parents
Substituents
  • Benzopyran
  • Vinylogous acid
  • Cyclic ketone
  • Ketone
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Enol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point178.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility24090 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available150.202http://allccs.zhulab.cn/database/detail?ID=AllCCS00001137
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.16 g/LALOGPS
logP1.23ALOGPS
logP0.81ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)3.55ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area83.83 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity65.25 m³·mol⁻¹ChemAxon
Polarizability25.01 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
DeepCCS[M+H]+157.04630932474
DeepCCS[M-H]-154.68830932474
DeepCCS[M-2H]-188.33630932474
DeepCCS[M+Na]+163.51230932474
AllCCS[M+H]+155.832859911
AllCCS[M+H-H2O]+152.132859911
AllCCS[M+NH4]+159.232859911
AllCCS[M+Na]+160.232859911
AllCCS[M-H]-158.732859911
AllCCS[M+Na-2H]-158.832859911
AllCCS[M+HCOO]-158.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Citrinin[H][C@]1(C)OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@]1([H])C3416.5Standard polar33892256
Citrinin[H][C@]1(C)OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@]1([H])C1779.7Standard non polar33892256
Citrinin[H][C@]1(C)OC=C2C(O)=C(C(O)=O)C(=O)C(C)=C2[C@]1([H])C2045.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citrinin,1TMS,isomer #1CC1=C2C(=CO[C@H](C)[C@H]2C)C(O[Si](C)(C)C)=C(C(=O)O)C1=O2055.9Semi standard non polar33892256
Citrinin,1TMS,isomer #2CC1=C2C(=CO[C@H](C)[C@H]2C)C(O)=C(C(=O)O[Si](C)(C)C)C1=O2036.4Semi standard non polar33892256
Citrinin,2TMS,isomer #1CC1=C2C(=CO[C@H](C)[C@H]2C)C(O[Si](C)(C)C)=C(C(=O)O[Si](C)(C)C)C1=O2107.3Semi standard non polar33892256
Citrinin,1TBDMS,isomer #1CC1=C2C(=CO[C@H](C)[C@H]2C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)O)C1=O2290.3Semi standard non polar33892256
Citrinin,1TBDMS,isomer #2CC1=C2C(=CO[C@H](C)[C@H]2C)C(O)=C(C(=O)O[Si](C)(C)C(C)(C)C)C1=O2265.6Semi standard non polar33892256
Citrinin,2TBDMS,isomer #1CC1=C2C(=CO[C@H](C)[C@H]2C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)O[Si](C)(C)C(C)(C)C)C1=O2523.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citrinin GC-MS (Non-derivatized) - 70eV, Positivesplash10-07ii-1950000000-bf6353469eb59dfd035e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrinin GC-MS (2 TMS) - 70eV, Positivesplash10-004i-3409000000-998272da21093d63d4732017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrinin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citrinin 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 - Citrinin LC-ESI-qToF , Positive-QTOFsplash10-001i-0290000000-19d08795fea7c80d6d852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrinin , positive-QTOFsplash10-001i-0290000000-19d08795fea7c80d6d852017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrinin 40V, Negative-QTOFsplash10-056r-0910000000-dc73977534605fabc1532021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrinin 20V, Negative-QTOFsplash10-0a6r-0980000000-0b8bfd0f8f61fc57c4a82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrinin 10V, Negative-QTOFsplash10-0002-0290000000-7d633abf71a04d44c8d52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrinin 40V, Positive-QTOFsplash10-066r-0920000000-707727c1075dd45d71082021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrinin 10V, Positive-QTOFsplash10-0f89-0090000000-d154c54944621174eae42021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Citrinin 20V, Positive-QTOFsplash10-001i-0090000000-fe2b94b81a1bd47da23c2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrinin 10V, Positive-QTOFsplash10-0udi-0090000000-448b730e55729839783f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrinin 20V, Positive-QTOFsplash10-0pc0-1390000000-b2d7bec5177df13bf6b22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrinin 40V, Positive-QTOFsplash10-0udi-9400000000-8c38a7814bc7b5aa24292016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrinin 10V, Negative-QTOFsplash10-0a4j-0090000000-cca6d7a143b768fc5b3d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrinin 20V, Negative-QTOFsplash10-0a4i-0390000000-4f2f5c7982385791b46f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrinin 40V, Negative-QTOFsplash10-015j-3910000000-b3cbc912af168ecaeb682016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrinin 10V, Negative-QTOFsplash10-052b-0090000000-27ccf87acb59e53486172021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrinin 20V, Negative-QTOFsplash10-0a4j-0190000000-b3dc2138a209a34bc5d42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrinin 40V, Negative-QTOFsplash10-000i-1900000000-488f0638f8ef7fb1568f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrinin 10V, Positive-QTOFsplash10-0ue9-0090000000-719d816638185ee9f2d32021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrinin 20V, Positive-QTOFsplash10-001i-0090000000-e68e48c0c6d1b9e9fce42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citrinin 40V, Positive-QTOFsplash10-0ll1-7790000000-34420a63944577cbd8872021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDC00029979
Chemspider ID10222475
KEGG Compound IDC16765
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCitrinin
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID48707
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1230771
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available