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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:11:06 UTC
Update Date2017-12-07 03:37:26 UTC
HMDB IDHMDB0035233
Secondary Accession Numbers
  • HMDB35233
Metabolite Identification
Common NameOlomoucine
DescriptionOlomoucine is found in root vegetables. Olomoucine is a constituent of the cotyledons of radish
Structure
Thumb
Synonyms
ValueSource
OlomucineChEMBL
2-(2-hydroxyethylamino)-6-benzylamino-9-IsopropylpurineHMDB
2-(2-hydroxyethylamino)-6-benzylamino-9-MethylpurineHMDB
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
6-benzylamino-2-[2-hydroxyethylamino]-9-MethylpurineHMDB
OLOHMDB
Chemical FormulaC15H18N6O
Average Molecular Weight298.343
Monoisotopic Molecular Weight298.154209228
IUPAC Name2-{[6-(benzylamino)-9-methyl-9H-purin-2-yl]amino}ethan-1-ol
Traditional Nameolomoucine
CAS Registry Number101622-51-9
SMILES
CN1C=NC2=C1N=C(NCCO)N=C2NCC1=CC=CC=C1
InChI Identifier
InChI=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
DescriptionThis compound belongs to the class of chemical entities known as 6-alkylaminopurines. These 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.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganoheterocyclic compounds
Sub ClassImidazopyrimidines
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
  • Alkanolamine
  • Azacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Cell and elements:

Source:

Role

Industrial application:

  Pharmaceutical industry:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point126 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-2090000000-727de3d1c16675ee79b2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9053000000-be27d1ff5e6080c227d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-3090000000-1a02264f7a6e067bfaeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9270000000-fbf772cf21b5b70b8208View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9110000000-b29b8eb3b1deb6b72744View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6t-1190000000-108ec4094423e5802cc8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pdj-2390000000-9d870540cc384c401f0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ox-4940000000-9d99195d8bd1c2d5919bView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02116
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB013890
KNApSAcK IDNot Available
Chemspider ID4431
KEGG Compound IDNot Available
BioCyc IDCPD-5442
BiGG IDNot Available
Wikipedia LinkGlial scar
METLIN IDNot Available
PubChem Compound4592
PDB IDOLO
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:20192247 ]
  2. 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. [PubMed:19368812 ]
  3. 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. [PubMed:10378797 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

General function:
Involved in MAP kinase activity
Specific function:
Acts as a transcriptional repressor. Binds to a [GC]AAA[GC] consensus sequence. Repress the expression of interferon gamma-induced genes. Seems to bind to the promoter of CCL5, DMP1, IFIH1, IFITM1, IRF7, IRF9, LAMP3, OAS1, OAS2, OAS3 and STAT1. Transcriptional activity is independent of kinase activity
Gene Name:
MAPK1
Uniprot ID:
P28482
Molecular weight:
41389.3
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
General function:
Involved in protein kinase activity
Specific function:
Plays a key role in the control of the eukaryotic cell cycle. It is required in higher cells for entry into S-phase and mitosis. p34 is a component of the kinase complex that phosphorylates the repetitive C-terminus of RNA polymerase II
Gene Name:
CDK1
Uniprot ID:
P06493
Molecular weight:
34081.1
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in protein kinase activity
Specific function:
Involved in the control of the cell cycle. Interacts with cyclins A, B1, B3, D, or E. Activity of CDK2 is maximal during S phase and G2
Gene Name:
CDK2
Uniprot ID:
P24941
Molecular weight:
33929.2
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in protein kinase activity
Specific function:
Probably involved in the control of the cell cycle. Interacts with D1 and D3-type G1 cyclins. Can phosphorylate histone H1, tau, MAP2 and NF-H and NF-M. Also interacts with p35 which activates the kinase
Gene Name:
CDK5
Uniprot ID:
Q00535
Molecular weight:
33304.1
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]