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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:29:40 UTC
Update Date2022-03-07 02:52:07 UTC
HMDB IDHMDB0029323
Secondary Accession Numbers
  • HMDB29323
Metabolite Identification
Common NameCitpressine I
DescriptionCitpressine I belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety. Based on a literature review very few articles have been published on Citpressine I.
Structure
Data?1582753402
Synonyms
ValueSource
1,6-Dihydroxy-3,5-dimethoxy-10-methylacridoneHMDB
Chemical FormulaC16H15NO5
Average Molecular Weight301.294
Monoisotopic Molecular Weight301.095022595
IUPAC Name1,6-dihydroxy-3,5-dimethoxy-10-methyl-9,10-dihydroacridin-9-one
Traditional Name1,6-dihydroxy-3,5-dimethoxy-10-methylacridin-9-one
CAS Registry Number81525-58-8
SMILES
COC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C(OC)=C(O)C=C1
InChI Identifier
InChI=1S/C16H15NO5/c1-17-10-6-8(21-2)7-12(19)13(10)15(20)9-4-5-11(18)16(22-3)14(9)17/h4-7,18-19H,1-3H3
InChI KeyOQMSMWRXIZYYNR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acridones. These are acridines containing a ketone group attached to the C9 carbon atom of the acridine moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassQuinolines and derivatives
Sub ClassBenzoquinolines
Direct ParentAcridones
Alternative Parents
Substituents
  • Acridone
  • Dihydroquinolone
  • Dihydroquinoline
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyridine
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Vinylogous amide
  • Ether
  • Azacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen 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 Point183 - 185 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility79.75 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP2.42ALOGPS
logP2.85ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)8.46ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area79.23 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity80.85 m³·mol⁻¹ChemAxon
Polarizability30.48 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]+170.41431661259
DarkChem[M-H]-171.61931661259
DeepCCS[M+H]+173.74630932474
DeepCCS[M-H]-171.38830932474
DeepCCS[M-2H]-205.51630932474
DeepCCS[M+Na]+180.74330932474
AllCCS[M+H]+167.732859911
AllCCS[M+H-H2O]+164.132859911
AllCCS[M+NH4]+171.032859911
AllCCS[M+Na]+171.932859911
AllCCS[M-H]-172.132859911
AllCCS[M+Na-2H]-171.532859911
AllCCS[M+HCOO]-171.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Citpressine ICOC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C(OC)=C(O)C=C13844.9Standard polar33892256
Citpressine ICOC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C(OC)=C(O)C=C12521.0Standard non polar33892256
Citpressine ICOC1=CC2=C(C(O)=C1)C(=O)C1=C(N2C)C(OC)=C(O)C=C13200.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Citpressine I,1TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=C(O)C(OC)=C3N(C)C2=C13033.8Semi standard non polar33892256
Citpressine I,1TMS,isomer #2COC1=CC(O)=C2C(=O)C3=CC=C(O[Si](C)(C)C)C(OC)=C3N(C)C2=C12964.1Semi standard non polar33892256
Citpressine I,2TMS,isomer #1COC1=CC(O[Si](C)(C)C)=C2C(=O)C3=CC=C(O[Si](C)(C)C)C(OC)=C3N(C)C2=C12918.9Semi standard non polar33892256
Citpressine I,1TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=C(O)C(OC)=C3N(C)C2=C13221.5Semi standard non polar33892256
Citpressine I,1TBDMS,isomer #2COC1=CC(O)=C2C(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3N(C)C2=C13185.2Semi standard non polar33892256
Citpressine I,2TBDMS,isomer #1COC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C3=CC=C(O[Si](C)(C)C(C)(C)C)C(OC)=C3N(C)C2=C13343.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Citpressine I GC-MS (Non-derivatized) - 70eV, Positivesplash10-05g0-0391000000-38e18a3f1e4ea21d87362017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citpressine I GC-MS (2 TMS) - 70eV, Positivesplash10-00e9-2055900000-d7981c59fd0c5d0598202017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Citpressine I 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 - Citpressine I 10V, Positive-QTOFsplash10-0udi-0019000000-3053c058899574a29c072016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citpressine I 20V, Positive-QTOFsplash10-0udi-0049000000-f9d7bf3bc19fc2e77d3a2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citpressine I 40V, Positive-QTOFsplash10-0ue9-0190000000-8fc484be38747af46ca02016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citpressine I 10V, Negative-QTOFsplash10-0udi-0009000000-f573deab1e7b7e3acf8f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citpressine I 20V, Negative-QTOFsplash10-0udi-0039000000-5b46181944eb4f2050442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citpressine I 40V, Negative-QTOFsplash10-0kea-1590000000-e162ad39e65488bd2b302016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citpressine I 10V, Negative-QTOFsplash10-0udi-0009000000-8b5d8847eb6f812d58cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citpressine I 20V, Negative-QTOFsplash10-0udi-0039000000-f8371ab0d797c11d90c42021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citpressine I 40V, Negative-QTOFsplash10-0udi-0390000000-53cea5714cae013878fa2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citpressine I 10V, Positive-QTOFsplash10-0udi-0009000000-0bc18c084a8f1a1da9542021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citpressine I 20V, Positive-QTOFsplash10-0udi-0009000000-0bc18c084a8f1a1da9542021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Citpressine I 40V, Positive-QTOFsplash10-0udi-0290000000-0ae3ca9dbb1245c7393b2021-09-23Wishart 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 IDFDB000384
KNApSAcK IDC00052240
Chemspider ID4592125
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5494827
PDB IDNot Available
ChEBI ID542817
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1808381
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.. .