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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:37:05 UTC
HMDB IDHMDB0015330
Secondary Accession Numbers
  • HMDB15330
Metabolite Identification
Common NameTubocurarine
DescriptionTubocurarine is only found in individuals that have used or taken this drug. It is a neuromuscular blocker and active ingredient in curare; plant based alkaloid of Menispermaceae. [PubChem]Tubocurarine, the chief alkaloid in tobacco products, binds stereo-selectively to nicotinic-cholinergic receptors at the autonomic ganglia, in the adrenal medulla, at neuromuscular junctions, and in the brain. Two types of central nervous system effects are believed to be the basis of Tubocurarine's positively reinforcing properties. A stimulating effect is exerted mainly in the cortex via the locus ceruleus and a reward effect is exerted in the limbic system. At low doses the stimulant effects predominate while at high doses the reward effects predominate. Intermittent intravenous administration of Tubocurarine activates neurohormonal pathways, releasing acetylcholine, norepinephrine, dopamine, serotonin, vasopressin, beta-endorphin, growth hormone, and ACTH.
Structure
Data?1582753284
Synonyms
ValueSource
(+)-TubocurarineChEBI
7',12'-Dihydroxy-6,6'-dimethoxy-2,2',2'-trimethyltubocuraraniumChEBI
D-TubocurarineChEBI
TubocurarinChEBI
D-Tubocurarine chlorideHMDB
Isoquinoline alkaloidHMDB
Tubocurarine chlorideHMDB
TubocurarinumHMDB
D-TubocurareHMDB
TubocurareHMDB
Chemical FormulaC37H41N2O6
Average Molecular Weight609.7312
Monoisotopic Molecular Weight609.296462054
IUPAC Name(1S,16R)-9,21-dihydroxy-10,25-dimethoxy-15,15,30-trimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2³,⁶.1⁸,¹².1¹⁸,²².0²⁷,³¹.0¹⁶,³⁴]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24,26,31,35-dodecaen-15-ium
Traditional Nametubocurarine
CAS Registry Number6989-98-6
SMILES
[H][C@@]12CC3=CC=C(OC4=C5C(CC[N+](C)(C)[C@]5([H])CC5=CC(OC6=C(OC)C=C(CCN1C)C2=C6)=C(O)C=C5)=CC(OC)=C4O)C=C3
InChI Identifier
InChI=1S/C37H40N2O6/c1-38-14-12-24-19-32(42-4)33-21-27(24)28(38)16-22-6-9-26(10-7-22)44-37-35-25(20-34(43-5)36(37)41)13-15-39(2,3)29(35)17-23-8-11-30(40)31(18-23)45-33/h6-11,18-21,28-29H,12-17H2,1-5H3,(H-,40,41)/p+1/t28-,29+/m0/s1
InChI KeyJFJZZMVDLULRGK-URLMMPGGSA-O
Chemical Taxonomy
Description Belongs to the class of organic compounds known as diarylethers. These are organic compounds containing the dialkyl ether functional group, with the formula ROR', where R and R' are aryl groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassEthers
Direct ParentDiarylethers
Alternative Parents
Substituents
  • Diaryl ether
  • Tetrahydroisoquinoline
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Benzenoid
  • Tetraalkylammonium salt
  • Quaternary ammonium salt
  • Tertiary amine
  • Tertiary aliphatic amine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic salt
  • Organic cation
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00032 g/LNot Available
LogPNot AvailableNot Available
Experimental Spectral PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00032 g/LALOGPS
logP10(3.12) g/LALOGPS
logP10(3.14) g/LChemAxon
logS10(-6.3) g/LALOGPS
pKa (Strongest Acidic)6.45ChemAxon
pKa (Strongest Basic)8.12ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.62 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity187.06 m³·mol⁻¹ChemAxon
Polarizability66.41 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+240.40531661259
DarkChem[M-H]-238.78531661259

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Tubocurarine,1TMS,#1COC1=CC2=C3C=C1OC1=CC(=CC=C1O[Si](C)(C)C)C[C@@H]1C4=C(C=C(OC)C(O)=C4OC4=CC=C(C=C4)C[C@@H]3N(C)CC2)CC[N+]1(C)C4786.4Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Tubocurarine,1TMS,#2COC1=CC2=C3C=C1OC1=CC(=CC=C1O)C[C@@H]1C4=C(C=C(OC)C(O[Si](C)(C)C)=C4OC4=CC=C(C=C4)C[C@@H]3N(C)CC2)CC[N+]1(C)C4775.1Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Tubocurarine,2TMS,#1COC1=CC2=C3C=C1OC1=CC(=CC=C1O[Si](C)(C)C)C[C@@H]1C4=C(C=C(OC)C(O[Si](C)(C)C)=C4OC4=CC=C(C=C4)C[C@@H]3N(C)CC2)CC[N+]1(C)C4748.1Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Tubocurarine,1TBDMS,#1COC1=CC2=C3C=C1OC1=CC(=CC=C1O[Si](C)(C)C(C)(C)C)C[C@@H]1C4=C(C=C(OC)C(O)=C4OC4=CC=C(C=C4)C[C@@H]3N(C)CC2)CC[N+]1(C)C4987.3Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Tubocurarine,1TBDMS,#2COC1=CC2=C3C=C1OC1=CC(=CC=C1O)C[C@@H]1C4=C(C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C4OC4=CC=C(C=C4)C[C@@H]3N(C)CC2)CC[N+]1(C)C4970.6Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Tubocurarine,2TBDMS,#1COC1=CC2=C3C=C1OC1=CC(=CC=C1O[Si](C)(C)C(C)(C)C)C[C@@H]1C4=C(C=C(OC)C(O[Si](C)(C)C(C)(C)C)=C4OC4=CC=C(C=C4)C[C@@H]3N(C)CC2)CC[N+]1(C)C5097.5Semi standard non polarLange, M. and Fedorova, M. (2020) Evaluation of lipid quantification accuracy using HILIC and RPLC MS on the example of NIST SRM 1950 metabolites in human plasma. Anal. Bioanal. Chem. 412(15), 3573-3584.
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Tubocurarine GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-0000091000-3781da48d16d597964cc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Tubocurarine GC-MS (1 TMS) - 70eV, Positivesplash10-01bi-0000009000-cf3870f9fb70af6daa942017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Tubocurarine Linear Ion Trap , positive-QTOFsplash10-03di-0000090000-3b12a16109f25ee309302017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Tubocurarine Linear Ion Trap , positive-QTOFsplash10-03di-0000090000-7ed720c5e8c5ce8facd32017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tubocurarine 10V, Positive-QTOFsplash10-0a59-0000089000-ac5f8d663869b48af1f02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tubocurarine 20V, Positive-QTOFsplash10-0560-0000091000-b985ecd4a2b2ff4197d82017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Tubocurarine 40V, Positive-QTOFsplash10-0fk9-0000090000-ae66666801b8fb874ed42017-09-01Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01199 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01199 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01199
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00001927
Chemspider ID5778
KEGG Compound IDC07547
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTubocurarine_chloride
METLIN IDNot Available
PubChem Compound6000
PDB IDNot Available
ChEBI ID9774
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. Youssef SA, Ramadan A, Afifi NA, Aziz MD: Influence of sodium taurocholate on the potency and duration of action of some neuromuscular blocking agents. Dtsch Tierarztl Wochenschr. 1991 Jun;98(6):213-6. [PubMed:1889362 ]

Enzymes

General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525
References
  1. Radic Z, Taylor P: The influence of peripheral site ligands on the reaction of symmetric and chiral organophosphates with wildtype and mutant acetylcholinesterases. Chem Biol Interact. 1999 May 14;119-120:111-7. [PubMed:10421444 ]
  2. Golicnik M, Fournier D, Stojan J: Acceleration of Drosophila melanogaster acetylcholinesterase methanesulfonylation: peripheral ligand D-tubocurarine enhances the affinity for small methanesulfonylfluoride. Chem Biol Interact. 2002 Feb 20;139(2):145-57. [PubMed:11823003 ]
  3. Radic Z, Taylor P: Peripheral site ligands accelerate inhibition of acetylcholinesterase by neutral organophosphates. J Appl Toxicol. 2001 Dec;21 Suppl 1:S13-4. [PubMed:11920914 ]
  4. Gupta RC, Dettbarn WD: Potential of memantine, D-tubocurarine, and atropine in preventing acute toxic myopathy induced by organophosphate nerve agents: soman, sarin, tabun and VX. Neurotoxicology. 1992 Fall;13(3):649-61. [PubMed:1475066 ]
  5. Bianchi DA, Hirschmann GS, Theoduloz C, Bracca AB, Kaufman TS: Synthesis of tricyclic analogs of stephaoxocanidine and their evaluation as acetylcholinesterase inhibitors. Bioorg Med Chem Lett. 2005 Jun 2;15(11):2711-5. [PubMed:15878275 ]
General function:
Involved in extracellular ligand-gated ion channel activity
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor is a ligand-gated ion channel, which when activated causes fast, depolarizing responses in neurons. It is a cation-specific, but otherwise relatively nonselective, ion channel
Gene Name:
HTR3A
Uniprot ID:
P46098
Molecular weight:
55279.8
References
  1. Hefft S, Hulo S, Bertrand D, Muller D: Synaptic transmission at nicotinic acetylcholine receptors in rat hippocampal organotypic cultures and slices. J Physiol. 1999 Mar 15;515 ( Pt 3):769-76. [PubMed:10066903 ]
  2. Yan D, White MM: Interaction of d-tubocurarine analogs with mutant 5-HT(3) receptors. Neuropharmacology. 2002 Sep;43(3):367-73. [PubMed:12243766 ]
  3. Yan D, Meyer JK, White MM: Mapping residues in the ligand-binding domain of the 5-HT(3) receptor onto d-tubocurarine structure. Mol Pharmacol. 2006 Aug;70(2):571-8. Epub 2006 May 24. [PubMed:16723497 ]
  4. Peters JA, Malone HM, Lambert JJ: Antagonism of 5-HT3 receptor mediated currents in murine N1E-115 neuroblastoma cells by (+)-tubocurarine. Neurosci Lett. 1990 Mar 2;110(1-2):107-12. [PubMed:1691468 ]
  5. Emerit MB, Riad M, Fattaccini CM, Hamon M: Characteristics of [14C]guanidinium accumulation in NG 108-15 cells exposed to serotonin 5-HT3 receptor ligands and substance P. J Neurochem. 1993 Jun;60(6):2059-67. [PubMed:7684066 ]
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Wenningmann I, Dilger JP: The kinetics of inhibition of nicotinic acetylcholine receptors by (+)-tubocurarine and pancuronium. Mol Pharmacol. 2001 Oct;60(4):790-6. [PubMed:11562442 ]
  4. Nishimura K, Kitamura Y, Taniguchi T, Agata K: Analysis of motor function modulated by cholinergic neurons in planarian Dugesia japonica. Neuroscience. 2010 Jun 16;168(1):18-30. doi: 10.1016/j.neuroscience.2010.03.038. Epub 2010 Mar 23. [PubMed:20338223 ]
  5. 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 ]
  6. 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 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Transporters

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. Busch AE, Quester S, Ulzheimer JC, Waldegger S, Gorboulev V, Arndt P, Lang F, Koepsell H: Electrogenic properties and substrate specificity of the polyspecific rat cation transporter rOCT1. J Biol Chem. 1996 Dec 20;271(51):32599-604. [PubMed:8955087 ]