Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-07-09 16:09:43 UTC
Update Date2021-09-14 15:48:01 UTC
HMDB IDHMDB0060962
Secondary Accession Numbers
  • HMDB60962
Metabolite Identification
Common Name3-hydroxyropivacaine
Description3-hydroxyropivacaine belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. 3-hydroxyropivacaine is a very strong basic compound (based on its pKa). The name ropivacaine refers to both the racemate and the marketed S-enantiomer. Ropivacaine hydrochloride is commonly marketed by AstraZeneca under the trade name Naropin. Ropivacaine is a local anaesthetic drug belonging to the amino amide group. 3-hydroxyropivacaine is a metabolite of ropivacaine.
Structure
Data?1563866128
SynonymsNot Available
Chemical FormulaC17H26N2O2
Average Molecular Weight290.4005
Monoisotopic Molecular Weight290.199428086
IUPAC Name(2R)-N-(3-hydroxy-2,6-dimethylphenyl)-1-propylpiperidine-2-carboximidic acid
Traditional Name(2R)-N-(3-hydroxy-2,6-dimethylphenyl)-1-propylpiperidine-2-carboximidic acid
CAS Registry NumberNot Available
SMILES
CCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O)=C1C
InChI Identifier
InChI=1S/C17H26N2O2/c1-4-10-19-11-6-5-7-14(19)17(21)18-16-12(2)8-9-15(20)13(16)3/h8-9,14,20H,4-7,10-11H2,1-3H3,(H,18,21)/t14-/m1/s1
InChI KeyIXOVDWXTIIYVOJ-CQSZACIVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acid amides
Alternative Parents
Substituents
  • Alpha-amino acid amide
  • 2-piperidinecarboxamide
  • Piperidinecarboxamide
  • Anilide
  • Xylenol
  • M-xylene
  • Xylene
  • P-cresol
  • N-arylamide
  • O-cresol
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Piperidine
  • Benzenoid
  • Monocyclic benzene moiety
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.23 g/LALOGPS
logP2.93ALOGPS
logP2.43ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)4.59ChemAxon
pKa (Strongest Basic)8.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area56.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity88.33 m³·mol⁻¹ChemAxon
Polarizability33.48 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]+170.81331661259
DarkChem[M-H]-170.19231661259
DeepCCS[M+H]+172.29530932474
DeepCCS[M-H]-169.93730932474
DeepCCS[M-2H]-202.83430932474
DeepCCS[M+Na]+178.38830932474
AllCCS[M+H]+171.132859911
AllCCS[M+H-H2O]+167.832859911
AllCCS[M+NH4]+174.232859911
AllCCS[M+Na]+175.032859911
AllCCS[M-H]-174.032859911
AllCCS[M+Na-2H]-174.332859911
AllCCS[M+HCOO]-174.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-hydroxyropivacaineCCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O)=C1C3067.4Standard polar33892256
3-hydroxyropivacaineCCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O)=C1C2422.5Standard non polar33892256
3-hydroxyropivacaineCCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O)=C1C2408.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-hydroxyropivacaine,1TMS,isomer #1CCCN1CCCC[C@@H]1C(=NC1=C(C)C=CC(O)=C1C)O[Si](C)(C)C2235.1Semi standard non polar33892256
3-hydroxyropivacaine,1TMS,isomer #2CCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O[Si](C)(C)C)=C1C2266.9Semi standard non polar33892256
3-hydroxyropivacaine,2TMS,isomer #1CCCN1CCCC[C@@H]1C(=NC1=C(C)C=CC(O[Si](C)(C)C)=C1C)O[Si](C)(C)C2298.5Semi standard non polar33892256
3-hydroxyropivacaine,1TBDMS,isomer #1CCCN1CCCC[C@@H]1C(=NC1=C(C)C=CC(O)=C1C)O[Si](C)(C)C(C)(C)C2424.5Semi standard non polar33892256
3-hydroxyropivacaine,1TBDMS,isomer #2CCCN1CCCC[C@@H]1C(O)=NC1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C2471.7Semi standard non polar33892256
3-hydroxyropivacaine,2TBDMS,isomer #1CCCN1CCCC[C@@H]1C(=NC1=C(C)C=CC(O[Si](C)(C)C(C)(C)C)=C1C)O[Si](C)(C)C(C)(C)C2690.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-hydroxyropivacaine GC-MS (Non-derivatized) - 70eV, Positivesplash10-000b-9810000000-7acf0f53478a7519055e2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-hydroxyropivacaine GC-MS (2 TMS) - 70eV, Positivesplash10-05bb-9331300000-19c714aa941ae4a571672017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-hydroxyropivacaine 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 - 3-hydroxyropivacaine 10V, Positive-QTOFsplash10-000f-0970000000-54ae3bdef9ba245c73892017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 20V, Positive-QTOFsplash10-004r-2900000000-87e117fede1bb2be7a8a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 40V, Positive-QTOFsplash10-000x-9300000000-8dc96f8f7acca723ad632017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 10V, Negative-QTOFsplash10-000i-0190000000-44e36d2dfbc5476483662017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 20V, Negative-QTOFsplash10-000i-0960000000-1fd4fefe9f449f37afa62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 40V, Negative-QTOFsplash10-0a5i-7900000000-bee7afe3c30b774e2ba62017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 10V, Positive-QTOFsplash10-0006-0490000000-2116bdfdf05c5f6e7f792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 20V, Positive-QTOFsplash10-004i-1920000000-51d5b249484b240384242021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 40V, Positive-QTOFsplash10-004j-4900000000-1eaa9f83312df113715e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 10V, Negative-QTOFsplash10-000i-0090000000-3f77951545ee2559c16a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 20V, Negative-QTOFsplash10-000i-1890000000-06bd65d148e83e1e45ce2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-hydroxyropivacaine 40V, Negative-QTOFsplash10-001i-2920000000-d609ce666238ccb261692021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableNormal
      Not Available
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound93486072
PDB IDNot Available
ChEBI IDNot Available
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 ReferencesNot Available