Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2013-06-12 17:33:21 UTC
Update Date2021-09-14 15:44:46 UTC
HMDB IDHMDB0060546
Secondary Accession Numbers
  • HMDB60546
Metabolite Identification
Common NameNorbuprenorphine
DescriptionNorbuprenorphine is the primary active metabolite of buprenorphine. Norbuprenorphine acts as a μ-opioid, δ-opioid, and nociceptin receptor full agonist, as well as a κ-opioid receptor partial agonist. Norbuprenorphine crosses the blood-brain-barrier similarly to buprenorphine and likely contributes to its effects. It was observed that Intravenous administration of norbuprenorphine at 1 to 3 mg/kg decreased respiratory rate, whereas buprenorphine had no effect up to 3 mg/kg in rats. (Wikipedia )
Structure
Data?1563866074
Synonyms
ValueSource
Des(cyclopropylmethyl)buprenorphineHMDB
N-DesalkylbuprenorphineHMDB
Chemical FormulaC25H35NO4
Average Molecular Weight413.5497
Monoisotopic Molecular Weight413.256608613
IUPAC Name(1S,2R,6S,14R,15R,16R)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11-trien-11-ol
Traditional Name(1S,2R,6S,14R,15R,16R)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-3-azahexacyclo[13.2.2.1²,⁸.0¹,⁶.0⁶,¹⁴.0⁷,¹²]icosa-7,9,11-trien-11-ol
CAS Registry NumberNot Available
SMILES
CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=C5C(O[C@@H]2[C@@]35CCN1)=C(O)C=C4
InChI Identifier
InChI=1S/C25H35NO4/c1-21(2,3)22(4,28)16-13-23-8-9-25(16,29-5)20-24(23)10-11-26-17(23)12-14-6-7-15(27)19(30-20)18(14)24/h6-7,16-17,20,26-28H,8-13H2,1-5H3/t16-,17-,20-,22+,23-,24+,25-/m1/s1
InChI KeyYOYLLRBMGQRFTN-IOMBULRVSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenanthrenes and derivatives
Sub ClassNot Available
Direct ParentPhenanthrenes and derivatives
Alternative Parents
Substituents
  • Phenanthrene
  • Azaspirodecane
  • Tetralin
  • Coumaran
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Piperidine
  • Tertiary alcohol
  • Dialkyl ether
  • Secondary aliphatic amine
  • Ether
  • Secondary amine
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Amine
  • Organooxygen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic 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 Solubility0.026 g/LALOGPS
logP3.19ALOGPS
logP2.3ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.8ChemAxon
pKa (Strongest Basic)10.49ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area70.95 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity114.53 m³·mol⁻¹ChemAxon
Polarizability45.95 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]+194.94831661259
DarkChem[M-H]-190.36831661259
DeepCCS[M-2H]-239.72930932474
DeepCCS[M+Na]+214.16130932474
AllCCS[M+H]+198.032859911
AllCCS[M+H-H2O]+195.732859911
AllCCS[M+NH4]+200.032859911
AllCCS[M+Na]+200.632859911
AllCCS[M-H]-207.332859911
AllCCS[M+Na-2H]-208.032859911
AllCCS[M+HCOO]-208.832859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Norbuprenorphine,1TMS,isomer #1CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O)C5=C4[C@@]3(CCN1)[C@H]2O53068.2Semi standard non polar33892256
Norbuprenorphine,1TMS,isomer #2CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C)C5=C4[C@@]3(CCN1)[C@H]2O53120.3Semi standard non polar33892256
Norbuprenorphine,1TMS,isomer #3CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=CC=C(O)C5=C4[C@@]3(CCN1[Si](C)(C)C)[C@H]2O53076.9Semi standard non polar33892256
Norbuprenorphine,2TMS,isomer #1CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C)C5=C4[C@@]3(CCN1)[C@H]2O53094.8Semi standard non polar33892256
Norbuprenorphine,2TMS,isomer #2CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O)C5=C4[C@@]3(CCN1[Si](C)(C)C)[C@H]2O53056.0Semi standard non polar33892256
Norbuprenorphine,2TMS,isomer #3CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C)[C@H]2O53093.2Semi standard non polar33892256
Norbuprenorphine,3TMS,isomer #1CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C)[C@H]2O53131.5Semi standard non polar33892256
Norbuprenorphine,3TMS,isomer #1CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C)[C@H]2O53386.3Standard non polar33892256
Norbuprenorphine,3TMS,isomer #1CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C)[C@H]2O53281.2Standard polar33892256
Norbuprenorphine,1TBDMS,isomer #1CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O)C5=C4[C@@]3(CCN1)[C@H]2O53321.0Semi standard non polar33892256
Norbuprenorphine,1TBDMS,isomer #2CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4[C@@]3(CCN1)[C@H]2O53342.4Semi standard non polar33892256
Norbuprenorphine,1TBDMS,isomer #3CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=CC=C(O)C5=C4[C@@]3(CCN1[Si](C)(C)C(C)(C)C)[C@H]2O53285.2Semi standard non polar33892256
Norbuprenorphine,2TBDMS,isomer #1CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4[C@@]3(CCN1)[C@H]2O53527.7Semi standard non polar33892256
Norbuprenorphine,2TBDMS,isomer #2CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O)C5=C4[C@@]3(CCN1[Si](C)(C)C(C)(C)C)[C@H]2O53500.8Semi standard non polar33892256
Norbuprenorphine,2TBDMS,isomer #3CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C(C)(C)C)[C@H]2O53521.0Semi standard non polar33892256
Norbuprenorphine,3TBDMS,isomer #1CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C(C)(C)C)[C@H]2O53764.3Semi standard non polar33892256
Norbuprenorphine,3TBDMS,isomer #1CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C(C)(C)C)[C@H]2O54023.3Standard non polar33892256
Norbuprenorphine,3TBDMS,isomer #1CO[C@]12CC[C@@]3(C[C@@H]1[C@](C)(O[Si](C)(C)C(C)(C)C)C(C)(C)C)[C@H]1CC4=CC=C(O[Si](C)(C)C(C)(C)C)C5=C4[C@@]3(CCN1[Si](C)(C)C(C)(C)C)[C@H]2O53540.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Norbuprenorphine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9135000000-45e0d329ab9294ed43172017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norbuprenorphine GC-MS (2 TMS) - 70eV, Positivesplash10-05g3-9001010000-5c6c16b735846e5659252017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norbuprenorphine GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norbuprenorphine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norbuprenorphine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norbuprenorphine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norbuprenorphine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norbuprenorphine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Norbuprenorphine GC-MS ("Norbuprenorphine,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine LC-ESI-QTOF , positive-QTOFsplash10-03di-0000900000-d0e136497c0156c9680f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine LC-ESI-QTOF , positive-QTOFsplash10-03di-0000900000-b04b0200f02b897bb6ef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine LC-ESI-QTOF , positive-QTOFsplash10-03di-0000900000-18c86464a0d8a8e11bf82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine LC-ESI-QTOF , positive-QTOFsplash10-03di-0143900000-52c84cfc3c7de4f838912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine LC-ESI-QTOF , positive-QTOFsplash10-03dr-0490100000-61fc9d6ff83269e9fe092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine 50V, Positive-QTOFsplash10-03ki-0691100000-b93b4447efa37aa300b02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine 40V, Positive-QTOFsplash10-03di-0263900000-362c7ffa1fc4db260e072021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine 50V, Positive-QTOFsplash10-03ki-0691100000-cc22b459c3503e03c2de2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine 30V, Positive-QTOFsplash10-03di-0000900000-a17b5bb24d801a8703c52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine 20V, Positive-QTOFsplash10-03di-0000900000-7f319d742b7c88e6d2942021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine 50V, Positive-QTOFsplash10-03dr-0490100000-61fc9d6ff83269e9fe092021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine 10V, Positive-QTOFsplash10-03di-0000900000-e8bb505ed3edc3b3f2332021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine 20V, Positive-QTOFsplash10-03di-0000900000-b04b0200f02b897bb6ef2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine 10V, Positive-QTOFsplash10-03di-0000900000-d0e136497c0156c9680f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine 30V, Positive-QTOFsplash10-03di-0000900000-18c86464a0d8a8e11bf82021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Norbuprenorphine 40V, Positive-QTOFsplash10-03di-0143900000-52c84cfc3c7de4f838912021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbuprenorphine 10V, Positive-QTOFsplash10-01ot-0009500000-f9107c3bc2684b887bb92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbuprenorphine 20V, Positive-QTOFsplash10-01ot-1009200000-5c2addf9f897497010552016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbuprenorphine 40V, Positive-QTOFsplash10-001i-4109000000-29b63bd2b3e8e8942b952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbuprenorphine 10V, Negative-QTOFsplash10-03di-0003900000-96dbf2e34e2566985c4e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbuprenorphine 20V, Negative-QTOFsplash10-03di-2129500000-c9958eaf16725890f6472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbuprenorphine 40V, Negative-QTOFsplash10-0002-1194000000-e835394a1e996708aa1c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbuprenorphine 10V, Positive-QTOFsplash10-03di-0000900000-22add0760b63a0f18d042021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbuprenorphine 20V, Positive-QTOFsplash10-03di-0001900000-bf64a5b4def2ecf8bf302021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Norbuprenorphine 40V, Positive-QTOFsplash10-03di-0003900000-17c40c03c2942ffaf0ba2021-10-12Wishart 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 LinkNorbuprenorphine
METLIN IDNot Available
PubChem Compound114976
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