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Record Information
Version2.0
Created at2022-04-27 22:28:59 UTC
Updated at2022-04-27 22:28:59 UTC
NP-MRD IDNP0051034
Secondary Accession NumbersNone
Natural Product Identification
Common Name(+)-Tubocurarine
DescriptionTubocurarine 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. Tubocurarine is a drug which is used as a diagnosis agent for myasthenia gravis, and also to facilitate the intubation after induction of anesthesia in surgical procedure. Tubocurarine is a very strong basic compound (based on its pKa). Tubocurarine is a potentially toxic compound. (+)-Tubocurarine is found in Chondodendron tomentosum . (+)-Tubocurarine was first documented in 1991 (PMID: 1889362). A benzylTubocurarine muscle relaxant which constitutes the active component of curare (PMID: 7911306) (PMID: 8166227).
Structure
Thumb
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 Mass609.7312 Da
Monoisotopic Mass609.29646 Da
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 NumberNot Available
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
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Chondodendron tomentosum-
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
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.12ALOGPS
logP3.14ChemAxon
logS-6.3ALOGPS
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
HMDB IDHMDB0015330
DrugBank IDDB01199
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDNot Available
References
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 ]
  2. Miguel RV, Barlow IK, Dombrowski DL: The effect of d-tubocurarine priming on an ED95 dose of vecuronium bromide. J Clin Anesth. 1994 Mar-Apr;6(2):106-9. doi: 10.1016/0952-8180(94)90005-1. [PubMed:7911306 ]
  3. O'Leary ME, Filatov GN, White MM: Characterization of d-tubocurarine binding site of Torpedo acetylcholine receptor. Am J Physiol. 1994 Mar;266(3 Pt 1):C648-53. doi: 10.1152/ajpcell.1994.266.3.C648. [PubMed:8166227 ]