Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2022-03-07 02:51:59 UTC
HMDB IDHMDB0015432
Secondary Accession Numbers
  • HMDB15432
Metabolite Identification
Common NameVecuronium
DescriptionMonoquaternary homolog of pancuronium. A non-depolarizing neuromuscular blocking agent with shorter duration of action than pancuronium. Its lack of significant cardiovascular effects and lack of dependence on good kidney function for elimination as well as its short duration of action and easy reversibility provide advantages over, or alternatives to, other established neuromuscular blocking agents. [PubChem]
Structure
Data?1582753297
Synonyms
ValueSource
Maleate, vecuroniumHMDB
NC 45HMDB
NorcuronHMDB
ORG-NC 45HMDB
ORGNC45HMDB
Vecuronium bromideHMDB
Vecuronium hydrobromideHMDB
Bromide, vecuroniumHMDB
Citrate, vecuroniumHMDB
ORG NC 45HMDB
ORG NC45HMDB
ORG-NC45HMDB
ORGNC 45HMDB
Vecuronium bromide, quaternary ionHMDB
Vecuronium citrateHMDB
Vecuronium hydrochlorideHMDB
Vecuronium phosphateHMDB
Hydrobromide, vecuroniumHMDB
Hydrochloride, vecuroniumHMDB
NC-45HMDB
ORG-NC-45HMDB
Phosphate, vecuroniumHMDB
Vecuronium maleateHMDB
Chemical FormulaC34H57N2O4
Average Molecular Weight557.8274
Monoisotopic Molecular Weight557.431833322
IUPAC Name1-[(1S,2S,4S,5S,7S,10R,11S,13S,14R,15S)-5,14-bis(acetyloxy)-2,15-dimethyl-4-(piperidin-1-yl)tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-13-yl]-1-methylpiperidin-1-ium
Traditional Namevecuronium
CAS Registry Number50700-72-6
SMILES
[H][C@@]12C[C@@H]([C@H](OC(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](OC(C)=O)[C@H](C[C@]12C)N1CCCCC1)[N+]1(C)CCCCC1
InChI Identifier
InChI=1S/C34H57N2O4/c1-23(37)39-31-20-25-12-13-26-27(34(25,4)22-29(31)35-16-8-6-9-17-35)14-15-33(3)28(26)21-30(32(33)40-24(2)38)36(5)18-10-7-11-19-36/h25-32H,6-22H2,1-5H3/q+1/t25-,26+,27-,28-,29-,30-,31-,32-,33-,34-/m0/s1
InChI KeyBGSZAXLLHYERSY-XQIGCQGXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as steroid esters. Steroid esters are compounds containing a steroid moiety which bears a carboxylic acid ester group.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Androstane-skeleton
  • Dicarboxylic acid or derivatives
  • Piperidine
  • Quaternary ammonium salt
  • Tetraalkylammonium salt
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Tertiary amine
  • Tertiary aliphatic amine
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Carbonyl group
  • Organic salt
  • Organic cation
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.9e-05 g/LNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.9e-05 g/LALOGPS
logP2.07ALOGPS
logP0.89ChemAxon
logS-7.5ALOGPS
pKa (Strongest Basic)9.65ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area55.84 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity169.31 m³·mol⁻¹ChemAxon
Polarizability66.85 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-261.17430932474
DeepCCS[M+Na]+234.97330932474
AllCCS[M+H]+236.632859911
AllCCS[M+H-H2O]+235.732859911
AllCCS[M+NH4]+237.332859911
AllCCS[M+Na]+237.532859911
AllCCS[M-H]-214.632859911
AllCCS[M+Na-2H]-217.032859911
AllCCS[M+HCOO]-219.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Vecuronium[H][C@@]12C[C@@H]([C@H](OC(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](OC(C)=O)[C@H](C[C@]12C)N1CCCCC1)[N+]1(C)CCCCC12757.5Standard polar33892256
Vecuronium[H][C@@]12C[C@@H]([C@H](OC(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](OC(C)=O)[C@H](C[C@]12C)N1CCCCC1)[N+]1(C)CCCCC13712.1Standard non polar33892256
Vecuronium[H][C@@]12C[C@@H]([C@H](OC(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@H](OC(C)=O)[C@H](C[C@]12C)N1CCCCC1)[N+]1(C)CCCCC13927.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Vecuronium GC-MS (Non-derivatized) - 70eV, Positivesplash10-00e9-0409810000-c6ede98a06a42a5e53f02017-09-01Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Vecuronium LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0000090000-30783b30128b3c20c2ae2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vecuronium LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0000090000-cd687d0e7ce4ae357aff2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vecuronium LC-ESI-QTOF , positive-QTOFsplash10-0a4i-0101090000-89eda364a0ed6638a6662017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vecuronium LC-ESI-QTOF , positive-QTOFsplash10-0pb9-1809120000-c2bee4083e6bf7f417b32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Vecuronium LC-ESI-QTOF , positive-QTOFsplash10-0zfr-2904000000-2c0dfbec678d7b5807712017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vecuronium 10V, Positive-QTOFsplash10-052b-0000690000-c7a9ef7836f46e2e3f5d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vecuronium 20V, Positive-QTOFsplash10-0592-0112930000-6cfd7dbe2c4519a1640d2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Vecuronium 40V, Positive-QTOFsplash10-0r6u-0214900000-1ac0fa6348e88c6aca4a2017-09-01Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01339 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01339 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01339
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID36358
KEGG Compound IDC07553
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkVecuronium bromide
METLIN IDNot Available
PubChem Compound39765
PDB IDNot Available
ChEBI ID9939
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Enzymes

General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane
Gene Name:
CHRNA2
Uniprot ID:
Q15822
Molecular weight:
59764.8
References
  1. Jonsson Fagerlund M, Dabrowski M, Eriksson LI: Pharmacological characteristics of the inhibition of nondepolarizing neuromuscular blocking agents at human adult muscle nicotinic acetylcholine receptor. Anesthesiology. 2009 Jun;110(6):1244-52. doi: 10.1097/ALN.0b013e31819fade3. [PubMed:19417616 ]
  2. Liu M, Dilger JP: Synergy between pairs of competitive antagonists at adult human muscle acetylcholine receptors. Anesth Analg. 2008 Aug;107(2):525-33. doi: 10.1213/ane.0b013e31817b4469. [PubMed:18633030 ]
  3. Paul M, Fokt RM, Kindler CH, Dipp NC, Yost CS: Characterization of the interactions between volatile anesthetics and neuromuscular blockers at the muscle nicotinic acetylcholine receptor. Anesth Analg. 2002 Aug;95(2):362-7, table of contents. [PubMed:12145052 ]

Transporters

General function:
Involved in ATP binding
Specific function:
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells
Gene Name:
ABCB1
Uniprot ID:
P08183
Molecular weight:
141477.3
References
  1. Smit JW, Weert B, Schinkel AH, Meijer DK: Heterologous expression of various P-glycoproteins in polarized epithelial cells induces directional transport of small (type 1) and bulky (type 2) cationic drugs. J Pharmacol Exp Ther. 1998 Jul;286(1):321-7. [PubMed:9655875 ]
General function:
Involved in ion transmembrane transporter activity
Specific function:
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnicotinamide (NMN), 4-(4-(dimethylamino)styryl)- N-methylpyridinium (ASP), the endogenous compounds choline, guanidine, histamine, epinephrine, adrenaline, noradrenaline and dopamine, and the drugs quinine, and metformin. The transport of organic cations is inhibited by a broad array of compounds like tetramethylammonium (TMA), cocaine, lidocaine, NMDA receptor antagonists, atropine, prazosin, cimetidine, TEA and NMN, guanidine, cimetidine, choline, procainamide, quinine, tetrabutylammonium, and tetrapentylammonium. Translocates organic cations in an electrogenic and pH-independent manner. Translocates organic cations across the plasma membrane in both directions. Transports the polyamines spermine and spermidine. Transports pramipexole across the basolateral membrane of the proximal tubular epithelial cells. The choline transport is activated by MMTS. Regulated by various intracellular signaling pathways including inhibition by protein kinase A activation, and endogenously activation by the calmodulin complex, the calmodulin- dependent kinase II and LCK tyrosine kinase
Gene Name:
SLC22A1
Uniprot ID:
O15245
Molecular weight:
61187.4
References
  1. Zhang L, Dresser MJ, Gray AT, Yost SC, Terashita S, Giacomini KM: Cloning and functional expression of a human liver organic cation transporter. Mol Pharmacol. 1997 Jun;51(6):913-21. [PubMed:9187257 ]
  2. Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880 ]