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Record Information
Version3.6
Creation Date2012-09-11 20:11:06 UTC
Update Date2016-02-11 02:39:42 UTC
HMDB IDHMDB35233
Secondary Accession NumbersNone
Metabolite Identification
Common NameOlomoucine
DescriptionOlomoucine is found in root vegetables. Olomoucine is a constituent of the cotyledons of radish. Olomoucine has been shown to exhibit anti-cancer, neuroprotectant, neuroprotective and apoptotic functions (PMID 20192247 , 19368812 , 19368812 , 10378797 ).
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 KeyInChIKey=GTVPOLSIJWJJNY-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassImidazopyrimidines
Sub ClassPurines and purine derivatives
Direct Parent6-alkylaminopurines
Alternative Parents
Substituents
  • 6-alkylaminopurine
  • Phenylmethylamine
  • Benzylamine
  • Secondary aliphatic/aromatic amine
  • Aminopyrimidine
  • Imidolactam
  • Benzenoid
  • Pyrimidine
  • N-substituted imidazole
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Imidazole
  • Azole
  • Azacycle
  • Secondary amine
  • Alkanolamine
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
  • Food
Biofunction
  • Nutrient
  • anti-cancer
  • apoptotic
  • neuroprotectant
  • neuroprotective
Application
  • Drug
Cellular locations
  • Cytoplasm
  • Extracellular
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity88.03 m3·mol-1ChemAxon
Polarizability32.85 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
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 IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB35233
Metagene LinkHMDB35233
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. [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. [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. [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. [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. [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. [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. [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. [10592235 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [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. [11752352 ]