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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:58:12 UTC
Update Date2022-03-07 02:54:20 UTC
HMDB IDHMDB0035031
Secondary Accession Numbers
  • HMDB35031
Metabolite Identification
Common NameDesoxylimonin
DescriptionCarbendazim, also known as bavistin or mecarzole, 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. It is also employed as a casting worm control agent in amenity turf situations such as golf greens and tennis courts. Carbendazim is a strong basic compound (based on its pKa). Carbendazim is a potentially toxic compound. INHALATION: supply fresh air. Carbendazim is a suspected endocrine disruptor. Rinse mouth with water (never give anything by mouth to an unconscious person).
Structure
Data?1563862654
Synonyms
ValueSource
1H-Benzimidazol-2-ylcarbamic acid methyl esterChEBI
2-(Methoxy-carbonylamino)-benzimidazolChEBI
2-(Methoxycarbonylamino)-benzimidazoleChEBI
2-(Methoxycarbonylamino)benzimidazoleChEBI
2-Benzimidazolecarbamic acid methyl esterChEBI
BMCChEBI
CarbendazimeChEBI
MBCChEBI
MecarzoleChEBI
Methyl 2-benzimidazolecarbamateChEBI
Methyl benzimidazol-2-ylcarbamateChEBI
1H-Benzimidazol-2-ylcarbamate methyl esterGenerator
2-Benzimidazolecarbamate methyl esterGenerator
Methyl 2-benzimidazolecarbamic acidGenerator
Methyl benzimidazol-2-ylcarbamic acidGenerator
1H-Benzimidazol-2-yl-carbamic acid, methyl esterHMDB
1H-Benzimidazol-2-ylcarbamic acid, methyl esterHMDB
1H-Benzimidazole-2-carbamic acid, methyl esterHMDB
2-(Carbomethoxyamino)benzimidazoleHMDB
2-(Methoxycarbamoyl)benzimidazoleHMDB
2-(Methoxycarboxamido)benzimidazoleHMDB
2-Benzimidazolecarbamic acid, methyl esterHMDB
2-Bezimidazolecarbamic acid methyl esterHMDB
2-MBCHMDB
2-Methyl benzimidazolecarbamateHMDB
2-[(Methoxycarbonyl)amino]benzimidazoleHMDB
a 118 (Pesticide)HMDB
AgrizimHMDB
Antibac MFHMDB
BattalHMDB
BavistanHMDB
BavistinHMDB
Bavistin 25SdHMDB
Bavistin 3460HMDB
Bavistin 50SdHMDB
Bavistin FLHMDB
BavistineHMDB
BCMHMDB
BCM (Fungicide)HMDB
BengardHMDB
Benzimidazole carbamate de methyleHMDB
Benzimidazole-2-carbamic acid, methyl esterHMDB
Benzimidazolecarbamate methyl esterHMDB
BenzimidazolecarbamicHMDB
Bercema-bitosenHMDB
BitosenHMDB
BMC?HMDB
BMKHMDB
BMK (Fungicide)HMDB
Carbamic acid, 1H-benzimidazol-2-yl-, methyl esterHMDB
Carbamic acid, 1H-benzimidazolyl-, methyl esterHMDB
Carbamic acid, N-1H-benzimidazol-2-yl-, methyl esterHMDB
Carben VLHMDB
CarbendazinHMDB
CarbendazineHMDB
CarbendazolHMDB
Carbendazol, jmafHMDB
CarbendazoleHMDB
CarbendazymHMDB
CarbendazymeHMDB
CustosHMDB
DelseneHMDB
Delsene 10HMDB
DerosalHMDB
Derosal 60PMHMDB
EquitdazinHMDB
FalicarbenHMDB
FunabenHMDB
Funaben 3HMDB
Funaben 50HMDB
FungisolHMDB
FungoxanHMDB
GarbendaHMDB
Ipo yHMDB
JkateinHMDB
JksteinHMDB
KarbenHMDB
Karben flo stefesHMDB
Karben stefes floHMDB
KemdazinHMDB
Kid pest project (carbendazim) (see also carbendazim)HMDB
KolfugoHMDB
Kolfugo 25 FWHMDB
Kolfugo 25FWHMDB
Kolfugo extraHMDB
MedamineHMDB
MekarzoleHMDB
Methoxybenzimidazole-2-carbamic acidHMDB
Methyl 1H-benzimidazol-2-ylcarbamateHMDB
Methyl 1H-benzimidazol-2-ylcarbamate (9ci)HMDB
Methyl 1H-benzimidazol-2-ylcarbamate, 9ciHMDB
Methyl 1H-benzimidazole-2-carbamateHMDB
Methyl 1H-benzimidazolylcarbamateHMDB
Methyl 2-benzimidazil carbamateHMDB
Methyl 2-benzimidazolylcarbamateHMDB
Methyl benzimidazolecarbamateHMDB
Methyl benzimidazolylcarbamateHMDB
Methyl N-2-benzimidazolecarbamateHMDB
Methyl-2-benzimidazole carbamateHMDB
Methyl-N-(2-benzimidazolyl)carbamateHMDB
Methylbenzimidazole-2-ylcarbamateHMDB
MYCOHMDB
OlginHMDB
Olgin (fungicide)HMDB
PillarstinHMDB
Preparation g 665HMDB
Preventol BCMHMDB
ProtekHMDB
SarfunHMDB
SPINHMDB
Spin (pesticide)HMDB
SteinHMDB
StemporHMDB
SubeejHMDB
SupercarbHMDB
ThicoperHMDB
TriticolHMDB
ZhiweilingHMDB
Mecarzole mononitrateHMDB
Mecarzole monophosphateHMDB
Mecarzole monosulfateHMDB
Mecarzole monohydrochlorideHMDB
Mecarzole monosodium saltHMDB
Mecarzole monophosphinateHMDB
Mecarzole triphosphinateHMDB
Carbendazim phosphateMeSH
DeoxylimoninHMDB
Chemical FormulaC26H30O7
Average Molecular Weight454.5122
Monoisotopic Molecular Weight454.199153314
IUPAC Name18-(furan-3-yl)-9,9,13,19-tetramethyl-4,8,17-trioxapentacyclo[11.8.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁹]henicos-14-ene-5,12,16-trione
Traditional Name18-(furan-3-yl)-9,9,13,19-tetramethyl-4,8,17-trioxapentacyclo[11.8.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁹]henicos-14-ene-5,12,16-trione
CAS Registry NumberNot Available
SMILES
CC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C=C12)C1=COC=C1
InChI Identifier
InChI=1S/C26H30O7/c1-23(2)16-9-18(27)25(4)15(26(16)13-31-20(28)11-19(26)33-23)5-7-24(3)17(25)10-21(29)32-22(24)14-6-8-30-12-14/h6,8,10,12,15-16,19,22H,5,7,9,11,13H2,1-4H3
InChI KeyQUTATOGBENCRSS-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
  • Benzenoid
  • Azole
  • Imidazole
  • Carbamic acid ester
  • Heteroaromatic compound
  • Carbonic acid derivative
  • Azacycle
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point323 - 325 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.033 g/LALOGPS
logP3.58ALOGPS
logP3.05ChemAxon
logS-4.1ALOGPS
pKa (Strongest Acidic)17.62ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area92.04 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity116.5 m³·mol⁻¹ChemAxon
Polarizability46.04 ųChemAxon
Number of Rings6ChemAxon
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]+202.31831661259
DarkChem[M-H]-197.81231661259
DeepCCS[M-2H]-236.69430932474
DeepCCS[M+Na]+212.11930932474
AllCCS[M+H]+206.532859911
AllCCS[M+H-H2O]+204.332859911
AllCCS[M+NH4]+208.532859911
AllCCS[M+Na]+209.032859911
AllCCS[M-H]-211.732859911
AllCCS[M+Na-2H]-212.632859911
AllCCS[M+HCOO]-213.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DesoxylimoninCC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C=C12)C1=COC=C14576.2Standard polar33892256
DesoxylimoninCC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C=C12)C1=COC=C13128.7Standard non polar33892256
DesoxylimoninCC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C=C12)C1=COC=C14125.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Desoxylimonin,1TMS,isomer #1CC1(C)OC2CC(=O)OCC23C1C=C(O[Si](C)(C)C)C1(C)C2=CC(=O)OC(C4=COC=C4)C2(C)CCC133554.3Semi standard non polar33892256
Desoxylimonin,1TMS,isomer #1CC1(C)OC2CC(=O)OCC23C1C=C(O[Si](C)(C)C)C1(C)C2=CC(=O)OC(C4=COC=C4)C2(C)CCC133220.9Standard non polar33892256
Desoxylimonin,1TBDMS,isomer #1CC1(C)OC2CC(=O)OCC23C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2=CC(=O)OC(C4=COC=C4)C2(C)CCC133796.3Semi standard non polar33892256
Desoxylimonin,1TBDMS,isomer #1CC1(C)OC2CC(=O)OCC23C1C=C(O[Si](C)(C)C(C)(C)C)C1(C)C2=CC(=O)OC(C4=COC=C4)C2(C)CCC133442.6Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Desoxylimonin GC-MS (Non-derivatized) - 70eV, Positivesplash10-06y7-3354900000-1a2d738fc12f48e1868e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Desoxylimonin 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 - Desoxylimonin 10V, Positive-QTOFsplash10-0a4s-0004900000-98c4861db64ca2ff90c52015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoxylimonin 20V, Positive-QTOFsplash10-0002-0009700000-8602a2762d51203dbe2f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoxylimonin 40V, Positive-QTOFsplash10-0170-4917200000-ead91c36cee6555178cb2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoxylimonin 10V, Negative-QTOFsplash10-0zfr-0000900000-44b174e375e7fd1060292015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoxylimonin 20V, Negative-QTOFsplash10-0pb9-2001900000-11911d33517bb8fe2f452015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoxylimonin 40V, Negative-QTOFsplash10-016v-3009200000-0f0ba3e6a512d08072202015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoxylimonin 10V, Negative-QTOFsplash10-0a4i-0000900000-90b0ff9633a1146d45892021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoxylimonin 20V, Negative-QTOFsplash10-0udi-0002900000-59c0ffe000c98ad6dc592021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoxylimonin 40V, Negative-QTOFsplash10-106s-1315900000-b620e09b1fffbf2a899a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoxylimonin 10V, Positive-QTOFsplash10-0a4i-0000900000-e4a6c18be33e55fe065c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoxylimonin 20V, Positive-QTOFsplash10-0a4i-1123900000-d6f410a4dd612921cc3e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Desoxylimonin 40V, Positive-QTOFsplash10-0002-5778900000-f13ea348590aa4f305ef2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • 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 IDDB13009
Phenol Explorer Compound IDNot Available
FooDB IDFDB008442
KNApSAcK IDNot Available
Chemspider ID23741
KEGG Compound IDC10897
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarbendazim
METLIN IDNot Available
PubChem Compound25429
PDB IDNot Available
ChEBI ID3392
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.