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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:20 UTC
Update Date2022-03-07 02:53:06 UTC
HMDB IDHMDB0031767
Secondary Accession Numbers
  • HMDB31767
Metabolite Identification
Common NameBenomyl
DescriptionBenomyl, also known as benlate or benlic acid, belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety. Based on a literature review a significant number of articles have been published on Benomyl.
Structure
Data?1563862167
Synonyms
ValueSource
1-(Butylcarbamoyl)-2-benzimidazol-methylcarbamatChEBI
1-(Butylcarbamoyl)-2-benzimidazolecarbamic acid, methyl esterChEBI
1-(N-Butylcarbamoyl)-2-(methoxy-carboxamido)-benzimidazolChEBI
BenlateChEBI
Methyl 1-(butylamino)carbonyl-1H-benzimidazol-2-ylcarbamateChEBI
Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamateChEBI
Methyl N-(1-butylcarbamoyl-2-benzimidazole)carbamateChEBI
1-(Butylcarbamoyl)-2-benzimidazolecarbamate, methyl esterGenerator
Benlic acidGenerator
Methyl 1-(butylamino)carbonyl-1H-benzimidazol-2-ylcarbamic acidGenerator
Methyl 1-(butylcarbamoyl)-2-benzimidazolecarbamic acidGenerator
Methyl N-(1-butylcarbamoyl-2-benzimidazole)carbamic acidGenerator
AgrocitHMDB
ArbortrineHMDB
ArilateHMDB
BBCHMDB
BenexHMDB
BenlatHMDB
Benlate 50HMDB
Benlate 50 WHMDB
Benlate 50WHMDB
BenomilHMDB
Benomyl 50WHMDB
Benomyl-imexHMDB
BenosanHMDB
BNMHMDB
Chinoin-fundazolHMDB
Du pont 1991HMDB
Dupont 1991HMDB
FibenzolHMDB
FundasolHMDB
FundazolHMDB
Fundazol 50WPHMDB
Fungicide 1991HMDB
Fungicide D-1991HMDB
FungochromHMDB
KribenomyHMDB
KribenomylHMDB
MBCLHMDB
Methyl 1-(butylcarbamoyl)-2-benzimidazolylcarbamateHMDB
Methyl 1-(butylcarbamoyl)benzimidazol-2-ylcarbamateHMDB
Methyl 1-[(butylamino)carbonyl]-1H-benzimidazol-2-ylcarbamate, 9ciHMDB
Methyl [1-(butylcarbamoyl)-1H-benzimidazol-2-yl]carbamateHMDB
NS 02 (Fungicide)HMDB
Tersan 1991HMDB
UzgenHMDB
Chemical FormulaC14H18N4O3
Average Molecular Weight290.3177
Monoisotopic Molecular Weight290.137890462
IUPAC NameN-butyl-2-{[hydroxy(methoxy)methylidene]amino}-1H-1,3-benzodiazole-1-carboximidic acid
Traditional Namebenomyl
CAS Registry Number17804-35-2
SMILES
CCCCN=C(O)N1C(N=C(O)OC)=NC2=CC=CC=C12
InChI Identifier
InChI=1S/C14H18N4O3/c1-3-4-9-15-13(19)18-11-8-6-5-7-10(11)16-12(18)17-14(20)21-2/h5-8H,3-4,9H2,1-2H3,(H,15,19)(H,16,17,20)
InChI KeyRIOXQFHNBCKOKP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-benzimidazolylcarbamic acid esters. These are aromatic heteropolycyclic compounds that contain a carbamic acid ester group, which is N-linked to the C2-atom of a benzimidazole moiety.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzimidazoles
Sub Class2-benzimidazolylcarbamic acid esters
Direct Parent2-benzimidazolylcarbamic acid esters
Alternative Parents
Substituents
  • 2-benzimidazolylcarbamic acid ester
  • Imidazole-1-carbonyl group
  • N-substituted imidazole
  • Benzenoid
  • Azole
  • Imidazole
  • Carbamic acid ester
  • Heteroaromatic compound
  • Urea
  • Carbonic acid derivative
  • Azacycle
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point140 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0038 mg/mL at 20 °CNot Available
LogP2.12Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.36 g/LALOGPS
logP2.32ALOGPS
logP3.68ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)2.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.23 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity79.49 m³·mol⁻¹ChemAxon
Polarizability31.15 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
DarkChem[M+H]+170.2231661259
DarkChem[M-H]-167.60531661259
DeepCCS[M-2H]-195.22830932474
DeepCCS[M+Na]+170.79430932474
AllCCS[M+H]+167.532859911
AllCCS[M+H-H2O]+164.332859911
AllCCS[M+NH4]+170.432859911
AllCCS[M+Na]+171.332859911
AllCCS[M-H]-168.832859911
AllCCS[M+Na-2H]-168.832859911
AllCCS[M+HCOO]-169.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
BenomylCCCCN=C(O)N1C(N=C(O)OC)=NC2=CC=CC=C123371.8Standard polar33892256
BenomylCCCCN=C(O)N1C(N=C(O)OC)=NC2=CC=CC=C122428.1Standard non polar33892256
BenomylCCCCN=C(O)N1C(N=C(O)OC)=NC2=CC=CC=C122597.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Benomyl,1TMS,isomer #1CCCCN=C(O[Si](C)(C)C)N1C(N=C(O)OC)=NC2=CC=CC=C212398.9Semi standard non polar33892256
Benomyl,1TMS,isomer #2CCCCN=C(O)N1C(N=C(OC)O[Si](C)(C)C)=NC2=CC=CC=C212375.4Semi standard non polar33892256
Benomyl,2TMS,isomer #1CCCCN=C(O[Si](C)(C)C)N1C(N=C(OC)O[Si](C)(C)C)=NC2=CC=CC=C212365.9Semi standard non polar33892256
Benomyl,1TBDMS,isomer #1CCCCN=C(O[Si](C)(C)C(C)(C)C)N1C(N=C(O)OC)=NC2=CC=CC=C212596.3Semi standard non polar33892256
Benomyl,1TBDMS,isomer #2CCCCN=C(O)N1C(N=C(OC)O[Si](C)(C)C(C)(C)C)=NC2=CC=CC=C212596.6Semi standard non polar33892256
Benomyl,2TBDMS,isomer #1CCCCN=C(O[Si](C)(C)C(C)(C)C)N1C(N=C(OC)O[Si](C)(C)C(C)(C)C)=NC2=CC=CC=C212728.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Benomyl GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8890000000-e030c9d552fc5c7d52da2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benomyl GC-MS (2 TMS) - 70eV, Positivesplash10-044i-9055500000-3eca627722374bbbc14c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Benomyl GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-052f-7900000000-930ea348a291d67fe0372014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benomyl 10V, Positive-QTOFsplash10-0006-2790000000-f3ed3b88d515aed07a442016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benomyl 20V, Positive-QTOFsplash10-01qc-1900000000-97b4102ec19aeb0c69742016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benomyl 40V, Positive-QTOFsplash10-001i-2900000000-1aa81e2473687dd335062016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benomyl 10V, Negative-QTOFsplash10-0a4l-2930000000-e8acc050770f45adf5362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benomyl 20V, Negative-QTOFsplash10-0a4l-4960000000-e995e6dd540486a3ceb22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benomyl 40V, Negative-QTOFsplash10-05ai-1900000000-c2b1949df8a55a1f654a2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benomyl 10V, Positive-QTOFsplash10-0006-0910000000-66be9480198a5327e7352021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benomyl 20V, Positive-QTOFsplash10-03di-0900000000-0c18c5b071a4b09c0c8e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benomyl 40V, Positive-QTOFsplash10-03di-2910000000-cd123ee8bdd6c595e2232021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benomyl 10V, Negative-QTOFsplash10-0a4i-4980000000-13f898af5a45ad5b34022021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benomyl 20V, Negative-QTOFsplash10-0cdi-1940000000-70fa20da8fb0758e32192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Benomyl 40V, Negative-QTOFsplash10-0536-6910000000-3b461f008e97c4b1b7082021-09-22Wishart 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008440
KNApSAcK IDNot Available
Chemspider ID26771
KEGG Compound IDC10896
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenomyl
METLIN IDNot Available
PubChem Compound28780
PDB IDNot Available
ChEBI ID3015
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. Edlind TD, Bartlett MS, Smith JW: Characterization of the beta-tubulin gene of Pneumocystis carinii. J Protozool. 1991 Nov-Dec;38(6):62S-63S. [PubMed:1818208 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .