Olomoucine (CHEM029158)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:58:18 UTC
Update Date2016-11-09 01:18:49 UTC
Accession NumberCHEM029158
Identification
Common NameOlomoucine
ClassSmall Molecule
DescriptionA 9H-purine that is substituted by a (2-hydroxyethyl)nitrilo, benzylnitrilo and a methyl group at positions 2,6 and 9, respectively. It is a cyclin-dependent kinase inhibitor.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(2-Hydroxyethylamino)-6-(benzylamino)-9-methylpurineChEBI
2-(Hydroxyethylamino)-6-benzylamino-9-methylpurineChEBI
2-[[9-Methyl-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]-ethanolChEBI
2-{[6-(benzylamino)-9-methyl-9H-purin-2-yl]amino}ethan-1-olChEBI
6-(Benzylamino)-2-(2-hydroxyethylamino)-9-methylpurineChEBI
OlomucineChEBI
2-(2-hydroxyethylamino)-6-benzylamino-9-IsopropylpurineHMDB
2-(2-hydroxyethylamino)-6-benzylamino-9-MethylpurineHMDB
2-[[9-Methyl-6-(phenylmethylamino)purin-2-yl]amino]ethanolHMDB
2-[[9-Methyl-6-[(phenylmethyl)amino]-9H-purin-2-yl]amino]ethanol, 9ciHMDB
4ERKHMDB
6-benzylamino-2-(2-hydroxyethylamino)-9-MethylpurineHMDB
6-benzylamino-2-[2-hydroxyethylamino]-9-MethylpurineHMDB
OLOHMDB
OlomoucineMeSH
Chemical FormulaC15H18N6O
Average Molecular Mass298.343 g/mol
Monoisotopic Mass298.154 g/mol
CAS Registry Number101622-51-9
IUPAC Name2-{[6-(benzylamino)-9-methyl-9H-purin-2-yl]amino}ethan-1-ol
Traditional Nameolomoucine
SMILESCN1C=NC2=C1N=C(NCCO)N=C2NCC1=CC=CC=C1
InChI IdentifierInChI=1S/C15H18N6O/c1-21-10-18-12-13(17-9-11-5-3-2-4-6-11)19-15(16-7-8-22)20-14(12)21/h2-6,10,22H,7-9H2,1H3,(H2,16,17,19,20)
InChI KeyGTVPOLSIJWJJNY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 6-alkylaminopurines. 6-alkylaminopurines are compounds that contain an alkylamine group attached at the 6-position of a purine. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-alkylaminopurines
Alternative Parents
Substituents
  • 6-alkylaminopurine
  • Benzylamine
  • Aminopyrimidine
  • Secondary aliphatic/aromatic amine
  • Monocyclic benzene moiety
  • N-substituted imidazole
  • Pyrimidine
  • Benzenoid
  • Imidolactam
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Secondary amine
  • Alkanolamine
  • Azacycle
  • Organopnictogen compound
  • Amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.51 g/LALOGPS
logP1.58ALOGPS
logP1.18ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)14.85ChemAxon
pKa (Strongest Basic)5.63ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area87.89 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity88.03 m³·mol⁻¹ChemAxon
Polarizability32.85 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-2090000000-727de3d1c16675ee79b2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9053000000-be27d1ff5e6080c227d2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3090000000-1a02264f7a6e067bfaeaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9270000000-fbf772cf21b5b70b8208Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9110000000-b29b8eb3b1deb6b72744Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-1190000000-108ec4094423e5802cc8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pdj-2390000000-9d870540cc384c401f0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-4940000000-9d99195d8bd1c2d5919bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-757aac0df42d659226cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fr2-0090000000-54cf210982df3c3bde73Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h0c-0960000000-f200ec48abef04eb8723Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0090000000-b472d91c0103cb9c1130Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-2090000000-22237306b326fad76387Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ox-6790000000-6d7faa5ffb62ef3ef98eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02116
HMDB IDHMDB0035233
FooDB IDFDB013890
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-5442
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGlial scar
Chemspider ID4431
ChEBI ID44661
PubChem Compound ID4592
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12147712
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=17094472
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=18385789
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19723061
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25422646
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=27241721
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=27345388
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=7523194
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=7549905
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=7925396
11. Smejkal K, Svacinova J, Slapetova T, Schneiderova K, Dall'acqua S, Innocenti G, Zavalova V, Kollar P, Chudik S, Marek R, Julinek O, Urbanova M, Kartal M, Csollei M, Dolezal K: Cytotoxic activities of several geranyl-substituted flavanones. J Nat Prod. 2010 Apr 23;73(4):568-72. doi: 10.1021/np900681y.
12. Fei XF, Qin ZH, Xiang B, Li LY, Han F, Fukunaga K, Liang ZQ: Olomoucine inhibits cathepsin L nuclear translocation, activates autophagy and attenuates toxicity of 6-hydroxydopamine. Brain Res. 2009 Apr 6;1264:85-97. doi: 10.1016/j.brainres.2009.01.057. Epub 2009 Feb 6.
13. Papazisis KT, Geromichalos GD, Kouretas D, Dimitriadis KA, Kortsaris AH: CDK-inhibitor olomoucine inhibits cell death after exposure of cell lines to cytosine-arabinoside. Cancer Lett. 1999 Apr 26;138(1-2):221-6.
14. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.