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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 20:11:06 UTC
Update Date2019-07-23 06:18:06 UTC
HMDB IDHMDB0035233
Secondary Accession Numbers
  • HMDB35233
Metabolite Identification
Common NameOlomoucine
DescriptionOlomoucine 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. Olomoucine has been detected, but not quantified in, root vegetables. This could make olomoucine a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Olomoucine.
Structure
Data?1563862686
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 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
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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point126 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.51 g/LALOGPS
logP10(1.58) g/LALOGPS
logP10(1.18) g/LChemAxon
logS10(-2.8) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+169.87231661259
DarkChem[M-H]-171.50331661259
DeepCCS[M+H]+161.70530932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
OlomoucineCN1C=NC2=C1N=C(NCCO)N=C2NCC1=CC=CC=C13766.9Standard polar33892256
OlomoucineCN1C=NC2=C1N=C(NCCO)N=C2NCC1=CC=CC=C12794.0Standard non polar33892256
OlomoucineCN1C=NC2=C1N=C(NCCO)N=C2NCC1=CC=CC=C13043.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Olomoucine,1TMS,isomer #1CN1C=NC2=C(NCC3=CC=CC=C3)N=C(NCCO[Si](C)(C)C)N=C212974.2Semi standard non polar33892256
Olomoucine,1TMS,isomer #2CN1C=NC2=C(NCC3=CC=CC=C3)N=C(N(CCO)[Si](C)(C)C)N=C212954.4Semi standard non polar33892256
Olomoucine,1TMS,isomer #3CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C)N=C(NCCO)N=C212943.8Semi standard non polar33892256
Olomoucine,2TMS,isomer #1CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C)N=C(NCCO[Si](C)(C)C)N=C212882.5Semi standard non polar33892256
Olomoucine,2TMS,isomer #1CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C)N=C(NCCO[Si](C)(C)C)N=C212653.2Standard non polar33892256
Olomoucine,2TMS,isomer #2CN1C=NC2=C(NCC3=CC=CC=C3)N=C(N(CCO[Si](C)(C)C)[Si](C)(C)C)N=C212930.6Semi standard non polar33892256
Olomoucine,2TMS,isomer #2CN1C=NC2=C(NCC3=CC=CC=C3)N=C(N(CCO[Si](C)(C)C)[Si](C)(C)C)N=C212844.6Standard non polar33892256
Olomoucine,2TMS,isomer #3CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C)N=C(N(CCO)[Si](C)(C)C)N=C212864.8Semi standard non polar33892256
Olomoucine,2TMS,isomer #3CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C)N=C(N(CCO)[Si](C)(C)C)N=C212786.8Standard non polar33892256
Olomoucine,3TMS,isomer #1CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C)N=C(N(CCO[Si](C)(C)C)[Si](C)(C)C)N=C212897.0Semi standard non polar33892256
Olomoucine,3TMS,isomer #1CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C)N=C(N(CCO[Si](C)(C)C)[Si](C)(C)C)N=C212688.2Standard non polar33892256
Olomoucine,1TBDMS,isomer #1CN1C=NC2=C(NCC3=CC=CC=C3)N=C(NCCO[Si](C)(C)C(C)(C)C)N=C213218.3Semi standard non polar33892256
Olomoucine,1TBDMS,isomer #2CN1C=NC2=C(NCC3=CC=CC=C3)N=C(N(CCO)[Si](C)(C)C(C)(C)C)N=C213166.1Semi standard non polar33892256
Olomoucine,1TBDMS,isomer #3CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C(C)(C)C)N=C(NCCO)N=C213158.4Semi standard non polar33892256
Olomoucine,2TBDMS,isomer #1CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C(C)(C)C)N=C(NCCO[Si](C)(C)C(C)(C)C)N=C213263.1Semi standard non polar33892256
Olomoucine,2TBDMS,isomer #1CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C(C)(C)C)N=C(NCCO[Si](C)(C)C(C)(C)C)N=C213025.9Standard non polar33892256
Olomoucine,2TBDMS,isomer #2CN1C=NC2=C(NCC3=CC=CC=C3)N=C(N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C213334.5Semi standard non polar33892256
Olomoucine,2TBDMS,isomer #2CN1C=NC2=C(NCC3=CC=CC=C3)N=C(N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C213175.5Standard non polar33892256
Olomoucine,2TBDMS,isomer #3CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C(C)(C)C)N=C(N(CCO)[Si](C)(C)C(C)(C)C)N=C213262.8Semi standard non polar33892256
Olomoucine,2TBDMS,isomer #3CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C(C)(C)C)N=C(N(CCO)[Si](C)(C)C(C)(C)C)N=C213137.1Standard non polar33892256
Olomoucine,3TBDMS,isomer #1CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C(C)(C)C)N=C(N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C213453.0Semi standard non polar33892256
Olomoucine,3TBDMS,isomer #1CN1C=NC2=C(N(CC3=CC=CC=C3)[Si](C)(C)C(C)(C)C)N=C(N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C213205.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Olomoucine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0296-2090000000-727de3d1c16675ee79b22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Olomoucine GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9053000000-be27d1ff5e6080c227d22017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Olomoucine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Olomoucine 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 - Olomoucine 10V, Positive-QTOFsplash10-0002-3090000000-1a02264f7a6e067bfaea2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olomoucine 20V, Positive-QTOFsplash10-0006-9270000000-fbf772cf21b5b70b82082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olomoucine 40V, Positive-QTOFsplash10-0006-9110000000-b29b8eb3b1deb6b727442016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olomoucine 10V, Negative-QTOFsplash10-0f6t-1190000000-108ec4094423e5802cc82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olomoucine 20V, Negative-QTOFsplash10-0pdj-2390000000-9d870540cc384c401f0f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olomoucine 40V, Negative-QTOFsplash10-01ox-4940000000-9d99195d8bd1c2d5919b2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olomoucine 10V, Negative-QTOFsplash10-0002-0090000000-757aac0df42d659226cb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olomoucine 20V, Negative-QTOFsplash10-0fr2-0090000000-54cf210982df3c3bde732021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olomoucine 40V, Negative-QTOFsplash10-0h0c-0960000000-f200ec48abef04eb87232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olomoucine 10V, Positive-QTOFsplash10-0002-0090000000-b472d91c0103cb9c11302021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olomoucine 20V, Positive-QTOFsplash10-0002-2090000000-22237306b326fad763872021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Olomoucine 40V, Positive-QTOFsplash10-01ox-6790000000-6d7faa5ffb62ef3ef98e2021-09-22Wishart 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 IDDB02116
Phenol Explorer Compound IDNot Available
FooDB 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 IDNot Available
ChEBI ID44661
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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 ]