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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:27 UTC
Update Date2022-03-07 02:53:07 UTC
HMDB IDHMDB0031785
Secondary Accession Numbers
  • HMDB31785
Metabolite Identification
Common NameRobenidine
DescriptionRobenidine, also known as robenz or khimkoktsid, belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety. Based on a literature review very few articles have been published on Robenidine.
Structure
Data?1563862170
Synonyms
ValueSource
1,3-Bis((p-chlorobenzylidene)amino)-guanidineHMDB
1,3-Bis((p-chlorobenzylidene)amino)guanidineHMDB
1,3-Bis[(p-chlorobenzylidene)amino]guanidine, 8ciHMDB
Bis((4-chlorophenyl)methylene)-carbonimidic dihydrazideHMDB
Bis[(4-chlorophenyl)methylene]-carbonimidic dihydrazideHMDB
Bis[(4-chlorophenyl)methylene]carbonimidic dihydrazide, 9ciHMDB
ChimcoccideHMDB
KhimcoccidHMDB
KhimkoktsidHMDB
KhimkoktsideHMDB
RobenidinaHMDB
Robenidine hydrochlorideHMDB
RobenidinumHMDB
RobenzHMDB
RobenzideneHMDB
RobenzidineHMDB
Alpharma brand OF robenidine hydrochlorideHMDB
CytostatHMDB
Hydrochloride, robenidineHMDB
RobenidineMeSH
Chemical FormulaC15H13Cl2N5
Average Molecular Weight334.203
Monoisotopic Molecular Weight333.054800855
IUPAC Name1-[(E)-[(4-chlorophenyl)methylidene]amino]-3-[(Z)-[(4-chlorophenyl)methylidene]amino]guanidine
Traditional Name1-[(E)-[(4-chlorophenyl)methylidene]amino]-3-[(Z)-[(4-chlorophenyl)methylidene]amino]guanidine
CAS Registry Number25875-51-8
SMILES
ClC1=CC=C(\C=N\NC(=N)N\N=C/C2=CC=C(Cl)C=C2)C=C1
InChI Identifier
InChI=1S/C15H13Cl2N5/c16-13-5-1-11(2-6-13)9-19-21-15(18)22-20-10-12-3-7-14(17)8-4-12/h1-10H,(H3,18,21,22)/b19-9-,20-10+
InChI KeyMOOFYEJFXBSZGE-KFSYKRRRSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as chlorobenzenes. Chlorobenzenes are compounds containing one or more chlorine atoms attached to a benzene moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Hydrazidine
  • Guanidine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0086 g/LALOGPS
logP1.98ALOGPS
logP4.38ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)19.39ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area72.63 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity122.65 m³·mol⁻¹ChemAxon
Polarizability31.8 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+178.2830932474
DeepCCS[M-H]-175.92230932474
DeepCCS[M-2H]-209.65630932474
DeepCCS[M+Na]+184.88330932474
AllCCS[M+H]+173.832859911
AllCCS[M+H-H2O]+170.632859911
AllCCS[M+NH4]+176.732859911
AllCCS[M+Na]+177.632859911
AllCCS[M-H]-171.632859911
AllCCS[M+Na-2H]-171.032859911
AllCCS[M+HCOO]-170.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
RobenidineClC1=CC=C(\C=N\NC(=N)N\N=C/C2=CC=C(Cl)C=C2)C=C13725.2Standard polar33892256
RobenidineClC1=CC=C(\C=N\NC(=N)N\N=C/C2=CC=C(Cl)C=C2)C=C12061.3Standard non polar33892256
RobenidineClC1=CC=C(\C=N\NC(=N)N\N=C/C2=CC=C(Cl)C=C2)C=C13426.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Robenidine,1TMS,isomer #1C[Si](C)(C)N(/N=C/C1=CC=C(Cl)C=C1)C(=N)N/N=C\C1=CC=C(Cl)C=C13205.5Semi standard non polar33892256
Robenidine,1TMS,isomer #1C[Si](C)(C)N(/N=C/C1=CC=C(Cl)C=C1)C(=N)N/N=C\C1=CC=C(Cl)C=C13296.8Standard non polar33892256
Robenidine,1TMS,isomer #2C[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N/N=C/C1=CC=C(Cl)C=C13213.2Semi standard non polar33892256
Robenidine,1TMS,isomer #2C[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N/N=C/C1=CC=C(Cl)C=C13108.9Standard non polar33892256
Robenidine,1TMS,isomer #3C[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N/N=C/C1=CC=C(Cl)C=C13205.5Semi standard non polar33892256
Robenidine,1TMS,isomer #3C[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N/N=C/C1=CC=C(Cl)C=C13296.8Standard non polar33892256
Robenidine,2TMS,isomer #1C[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C3113.1Semi standard non polar33892256
Robenidine,2TMS,isomer #1C[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C3178.9Standard non polar33892256
Robenidine,2TMS,isomer #2C[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C3085.1Semi standard non polar33892256
Robenidine,2TMS,isomer #2C[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C3286.9Standard non polar33892256
Robenidine,2TMS,isomer #3C[Si](C)(C)N=C(N/N=C/C1=CC=C(Cl)C=C1)N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C3113.1Semi standard non polar33892256
Robenidine,2TMS,isomer #3C[Si](C)(C)N=C(N/N=C/C1=CC=C(Cl)C=C1)N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C3178.9Standard non polar33892256
Robenidine,3TMS,isomer #1C[Si](C)(C)N=C(N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C3158.4Semi standard non polar33892256
Robenidine,3TMS,isomer #1C[Si](C)(C)N=C(N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C3054.1Standard non polar33892256
Robenidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(/N=C/C1=CC=C(Cl)C=C1)C(=N)N/N=C\C1=CC=C(Cl)C=C13386.9Semi standard non polar33892256
Robenidine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(/N=C/C1=CC=C(Cl)C=C1)C(=N)N/N=C\C1=CC=C(Cl)C=C13419.6Standard non polar33892256
Robenidine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N/N=C/C1=CC=C(Cl)C=C13412.8Semi standard non polar33892256
Robenidine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N/N=C/C1=CC=C(Cl)C=C13286.6Standard non polar33892256
Robenidine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N/N=C/C1=CC=C(Cl)C=C13386.9Semi standard non polar33892256
Robenidine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N/N=C/C1=CC=C(Cl)C=C13419.6Standard non polar33892256
Robenidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C3491.5Semi standard non polar33892256
Robenidine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(N/N=C\C1=CC=C(Cl)C=C1)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C3481.6Standard non polar33892256
Robenidine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C3511.0Semi standard non polar33892256
Robenidine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N(/N=C\C1=CC=C(Cl)C=C1)C(=N)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C3569.7Standard non polar33892256
Robenidine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N=C(N/N=C/C1=CC=C(Cl)C=C1)N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C3491.5Semi standard non polar33892256
Robenidine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N=C(N/N=C/C1=CC=C(Cl)C=C1)N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C3481.6Standard non polar33892256
Robenidine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C3754.4Semi standard non polar33892256
Robenidine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N=C(N(/N=C\C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C)N(/N=C/C1=CC=C(Cl)C=C1)[Si](C)(C)C(C)(C)C3566.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Robenidine GC-MS (Non-derivatized) - 70eV, Positivesplash10-003r-0901000000-bd3c64c75f0b6bd6835f2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Robenidine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Robenidine 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 - Robenidine 10V, Positive-QTOFsplash10-001i-0509000000-1340b46a98b339692f082017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Robenidine 20V, Positive-QTOFsplash10-0040-0902000000-b8ecacc20a50391b5c942017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Robenidine 40V, Positive-QTOFsplash10-000i-1900000000-ab4e9201f85a37fc505b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Robenidine 10V, Negative-QTOFsplash10-001i-0609000000-36085c7522e6c99f14572017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Robenidine 20V, Negative-QTOFsplash10-0udi-0901000000-600675618f3b0670cb142017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Robenidine 40V, Negative-QTOFsplash10-0ikl-2900000000-48681aecdbfff61982f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Robenidine 10V, Negative-QTOFsplash10-001i-0209000000-c91fff2e7cc4e42fe9e92021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Robenidine 20V, Negative-QTOFsplash10-0f89-9803000000-c66e0d086dd8888529532021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Robenidine 40V, Negative-QTOFsplash10-001i-9000000000-0c585b3615c9542786b22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Robenidine 10V, Positive-QTOFsplash10-001i-0309000000-c043134b850721f887e12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Robenidine 20V, Positive-QTOFsplash10-003r-0900000000-b6505f3eb5f43ed1fac12021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Robenidine 40V, Positive-QTOFsplash10-002r-0900000000-fcc19c5c36922ed2bd4f2021-09-25Wishart 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008458
KNApSAcK IDNot Available
Chemspider ID17946882
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRobenidine
METLIN IDNot Available
PubChem Compound18527351
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.. .