Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:32 UTC
Update Date2022-03-07 02:53:07 UTC
HMDB IDHMDB0031799
Secondary Accession Numbers
  • HMDB31799
Metabolite Identification
Common NameMalonoben
DescriptionMalonoben belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety. Based on a literature review a significant number of articles have been published on Malonoben.
Structure
Data?1563862172
Synonyms
ValueSource
(3,5-Di-t-butyl-4-hydroxybenzylidene)malononitrileHMDB
(3,5-Di-tert-butyl-4-hydroxy-benzylidene)malononitrileHMDB
(3,5-Di-tert-butyl-4-hydroxybenzylidene)-malononitrileHMDB
2,6-Di-tert-butyl-4-(2,2-dicyanovinyl)phenolHMDB
2-(3,5-Di-tert-butyl-4-hydroxybenzylidene)malononitrileHMDB
3,5-Di-t-butyl-4-hydroxy-benzylidenemalononitrileHMDB
3,5-Di-tert-butyl-4-hydroxybenzilidenemalononitrileHMDB
3,5-Di-tert-butyl-4-hydroxybenzylidene-malononitrileHMDB
SF 6847HMDB
[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]propanedinitrile, 9ciHMDB
Tyrphostin a9MeSH
Chemical FormulaC18H22N2O
Average Molecular Weight282.3801
Monoisotopic Molecular Weight282.173213336
IUPAC Name2-[(3,5-di-tert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile
Traditional Name2-[(3,5-di-tert-butyl-4-hydroxyphenyl)methylidene]propanedinitrile
CAS Registry Number10537-47-0
SMILES
CC(C)(C)C1=CC(C=C(C#N)C#N)=CC(=C1O)C(C)(C)C
InChI Identifier
InChI=1S/C18H22N2O/c1-17(2,3)14-8-12(7-13(10-19)11-20)9-15(16(14)21)18(4,5)6/h7-9,21H,1-6H3
InChI KeyMZOPWQKISXCCTP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropanes
Direct ParentPhenylpropanes
Alternative Parents
Substituents
  • Phenylpropane
  • Phenol
  • Nitrile
  • Carbonitrile
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point141 - 143 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0056 g/LALOGPS
logP5.47ALOGPS
logP4.96ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)8.79ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.81 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity86.41 m³·mol⁻¹ChemAxon
Polarizability32.57 ųChemAxon
Number of Rings1ChemAxon
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]+169.68531661259
DarkChem[M-H]-167.38331661259
DeepCCS[M+H]+175.35330932474
DeepCCS[M-H]-172.99530932474
DeepCCS[M-2H]-206.63430932474
DeepCCS[M+Na]+181.86230932474
AllCCS[M+H]+163.632859911
AllCCS[M+H-H2O]+160.332859911
AllCCS[M+NH4]+166.632859911
AllCCS[M+Na]+167.432859911
AllCCS[M-H]-173.832859911
AllCCS[M+Na-2H]-173.732859911
AllCCS[M+HCOO]-173.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MalonobenCC(C)(C)C1=CC(C=C(C#N)C#N)=CC(=C1O)C(C)(C)C3059.9Standard polar33892256
MalonobenCC(C)(C)C1=CC(C=C(C#N)C#N)=CC(=C1O)C(C)(C)C1970.3Standard non polar33892256
MalonobenCC(C)(C)C1=CC(C=C(C#N)C#N)=CC(=C1O)C(C)(C)C2299.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Malonoben,1TMS,isomer #1CC(C)(C)C1=CC(C=C(C#N)C#N)=CC(C(C)(C)C)=C1O[Si](C)(C)C2270.4Semi standard non polar33892256
Malonoben,1TBDMS,isomer #1CC(C)(C)C1=CC(C=C(C#N)C#N)=CC(C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C2488.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Malonoben GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-2190000000-6dc9933ae3f0f35d57612017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Malonoben GC-MS (1 TMS) - 70eV, Positivesplash10-0079-7398000000-8bdef250059f7c2d37a72017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Malonoben GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Malonoben GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Malonoben LC-ESI-qTof , Positive-QTOFsplash10-000i-3980000000-dc67e28bf67c9f7991082017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Malonoben , positive-QTOFsplash10-03dj-0930000000-dd3a00c3026cef3df28c2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malonoben 10V, Positive-QTOFsplash10-001i-0090000000-8e4c34f669d44a715ff82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malonoben 20V, Positive-QTOFsplash10-0560-0090000000-fbca0da0d0a64fb489f42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malonoben 40V, Positive-QTOFsplash10-0a4i-2290000000-df11bc58a3a41f87aa4d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malonoben 10V, Negative-QTOFsplash10-001i-0090000000-0cc6ed32a18e26122b252016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malonoben 20V, Negative-QTOFsplash10-001i-0090000000-51e82b58663f10fbec4a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malonoben 40V, Negative-QTOFsplash10-0f9t-1190000000-975ed68e963542428b2f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malonoben 10V, Positive-QTOFsplash10-003r-0090000000-7f246da144c0720c0aa82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malonoben 20V, Positive-QTOFsplash10-003r-2190000000-179ba52afb151af6eec32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malonoben 40V, Positive-QTOFsplash10-0600-4920000000-5d3748f532e4cf0d77b22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malonoben 10V, Negative-QTOFsplash10-001i-0090000000-3a842f545d21389ac0502021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malonoben 20V, Negative-QTOFsplash10-001i-0090000000-3a842f545d21389ac0502021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Malonoben 40V, Negative-QTOFsplash10-014i-0090000000-0fa50ff501577e67d4ad2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB008472
KNApSAcK IDNot Available
Chemspider ID5412
KEGG Compound IDC19039
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSF-6847
METLIN IDNot Available
PubChem Compound5614
PDB IDNot Available
ChEBI IDNot Available
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. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .