Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:12 UTC
Update Date2022-03-07 02:53:06 UTC
HMDB IDHMDB0031751
Secondary Accession Numbers
  • HMDB31751
Metabolite Identification
Common Namey-Morphine
Descriptiony-Morphine, also known as 2,2'bimorphine or dehydromorphine, belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. Based on a literature review a small amount of articles have been published on y-Morphine.
Structure
Data?1563862165
Synonyms
ValueSource
2,2'-BimorphineHMDB
2,2'BimorphineHMDB
7,7',8,8'-Tetrahydro-4,5:4',5'-diepoxy-17,17'-dimethyl[2,2'-bimorphinan], 9ciHMDB
DehydromorphineHMDB
OxydimorphineHMDB
OxymorphineHMDB
PseudomorphineHMDB
Chemical FormulaC34H36N2O6
Average Molecular Weight568.6594
Monoisotopic Molecular Weight568.257336894
IUPAC Name9-{10,14-dihydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraen-9-yl}-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7,9,11(18),15-tetraene-10,14-diol
Traditional Namepseudomorphine
CAS Registry Number125-24-6
SMILES
CN1CCC23C4OC5=C2C(CC1C3C=CC4O)=CC(=C5O)C1=C(O)C2=C3C(CC4C5C=CC(O)C(O2)C35CCN4C)=C1
InChI Identifier
InChI=1S/C34H36N2O6/c1-35-9-7-33-19-3-5-23(37)31(33)41-29-25(33)15(13-21(19)35)11-17(27(29)39)18-12-16-14-22-20-4-6-24(38)32-34(20,8-10-36(22)2)26(16)30(42-32)28(18)40/h3-6,11-12,19-24,31-32,37-40H,7-10,13-14H2,1-2H3
InChI KeyFOJYFDFNGPRXDR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as morphinans. These are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassMorphinans
Sub ClassNot Available
Direct ParentMorphinans
Alternative Parents
Substituents
  • Neolignan skeleton
  • Morphinan
  • Phenanthrene
  • Tetralin
  • Coumaran
  • Alkyl aryl ether
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Secondary alcohol
  • Tertiary amine
  • Tertiary aliphatic amine
  • Oxacycle
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point330 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP2.04ALOGPS
logP1.04ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)9.81ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area105.86 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity159.32 m³·mol⁻¹ChemAxon
Polarizability63.19 ųChemAxon
Number of Rings10ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+227.12631661259
DarkChem[M-H]-222.20631661259
DeepCCS[M-2H]-264.15830932474
DeepCCS[M+Na]+239.00330932474
AllCCS[M+H]+234.532859911
AllCCS[M+H-H2O]+233.232859911
AllCCS[M+NH4]+235.732859911
AllCCS[M+Na]+236.032859911
AllCCS[M-H]-230.932859911
AllCCS[M+Na-2H]-232.832859911
AllCCS[M+HCOO]-235.132859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.2.46 minutes32390414
Predicted by Siyang on May 30, 202210.8484 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.09 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid248.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid835.5 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid192.3 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid165.2 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid185.8 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid77.0 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid308.5 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid333.3 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)1066.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid744.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid246.8 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid894.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid223.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid261.9 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate522.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA699.5 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water93.3 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
y-MorphineCN1CCC23C4OC5=C2C(CC1C3C=CC4O)=CC(=C5O)C1=C(O)C2=C3C(CC4C5C=CC(O)C(O2)C35CCN4C)=C14783.3Standard polar33892256
y-MorphineCN1CCC23C4OC5=C2C(CC1C3C=CC4O)=CC(=C5O)C1=C(O)C2=C3C(CC4C5C=CC(O)C(O2)C35CCN4C)=C12684.3Standard non polar33892256
y-MorphineCN1CCC23C4OC5=C2C(CC1C3C=CC4O)=CC(=C5O)C1=C(O)C2=C3C(CC4C5C=CC(O)C(O2)C35CCN4C)=C14898.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
y-Morphine,1TMS,isomer #1CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O)C=CC3C1C54847.0Semi standard non polar33892256
y-Morphine,1TMS,isomer #2CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C)OC6C(O)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O)C=CC3C1C54872.5Semi standard non polar33892256
y-Morphine,2TMS,isomer #1CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O)C=CC3C1C54774.2Semi standard non polar33892256
y-Morphine,2TMS,isomer #2CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O[Si](C)(C)C)=C4OC2C(O)C=CC3C1C54772.9Semi standard non polar33892256
y-Morphine,2TMS,isomer #3CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O[Si](C)(C)C)C=CC3C1C54739.4Semi standard non polar33892256
y-Morphine,2TMS,isomer #4CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C)OC6C(O)C=CC9C(C7)N(C)CCC896)C(O[Si](C)(C)C)=C4OC2C(O)C=CC3C1C54803.4Semi standard non polar33892256
y-Morphine,3TMS,isomer #1CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O[Si](C)(C)C)=C4OC2C(O)C=CC3C1C54730.1Semi standard non polar33892256
y-Morphine,3TMS,isomer #2CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O[Si](C)(C)C)C=CC3C1C54700.2Semi standard non polar33892256
y-Morphine,4TMS,isomer #1CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C)OC6C(O[Si](C)(C)C)C=CC9C(C7)N(C)CCC896)C(O[Si](C)(C)C)=C4OC2C(O[Si](C)(C)C)C=CC3C1C54665.4Semi standard non polar33892256
y-Morphine,1TBDMS,isomer #1CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O)OC6C(O[Si](C)(C)C(C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O)C=CC3C1C55025.4Semi standard non polar33892256
y-Morphine,1TBDMS,isomer #2CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C(C)(C)C)OC6C(O)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O)C=CC3C1C55056.9Semi standard non polar33892256
y-Morphine,2TBDMS,isomer #1CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C(C)(C)C)OC6C(O[Si](C)(C)C(C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O)C=CC3C1C55129.9Semi standard non polar33892256
y-Morphine,2TBDMS,isomer #2CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O)OC6C(O[Si](C)(C)C(C)(C)C)C=CC9C(C7)N(C)CCC896)C(O[Si](C)(C)C(C)(C)C)=C4OC2C(O)C=CC3C1C55127.7Semi standard non polar33892256
y-Morphine,2TBDMS,isomer #3CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O)OC6C(O[Si](C)(C)C(C)(C)C)C=CC9C(C7)N(C)CCC896)C(O)=C4OC2C(O[Si](C)(C)C(C)(C)C)C=CC3C1C55092.6Semi standard non polar33892256
y-Morphine,2TBDMS,isomer #4CN1CCC23C4=C5C=C(C6=CC7=C8C(=C6O[Si](C)(C)C(C)(C)C)OC6C(O)C=CC9C(C7)N(C)CCC896)C(O[Si](C)(C)C(C)(C)C)=C4OC2C(O)C=CC3C1C55166.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0v00-2000090000-174325cbb89f345f78052017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (1 TMS) - 70eV, Positivesplash10-00b9-9000045000-e08b9c116733de3d4a012017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS ("y-Morphine,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TMS_2_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TMS_3_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TMS_3_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TMS_4_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - y-Morphine GC-MS (TBDMS_2_4) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - y-Morphine 10V, Positive-QTOFsplash10-014i-0000090000-3a67c2c327b70a10015a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - y-Morphine 20V, Positive-QTOFsplash10-014i-0030090000-b6150fa06b54d6f31d4e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - y-Morphine 40V, Positive-QTOFsplash10-0006-3090150000-ed2bfee9e9434880ef882016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - y-Morphine 10V, Negative-QTOFsplash10-014i-0000090000-05f51fdb3f7ad93b6c7e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - y-Morphine 20V, Negative-QTOFsplash10-0159-0060090000-3fa0169a42bb58fc17b72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - y-Morphine 40V, Negative-QTOFsplash10-003r-0090010000-d1384d9ad3412100559d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - y-Morphine 10V, Positive-QTOFsplash10-014i-0000090000-524a091d90240fb5cd472021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - y-Morphine 20V, Positive-QTOFsplash10-014r-0000090000-a3820722ce37a2ff5d672021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - y-Morphine 40V, Positive-QTOFsplash10-01p9-0000190000-37f5f984f804e4ce51be2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - y-Morphine 10V, Negative-QTOFsplash10-014i-0000090000-6312a1c194c99bba2b012021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - y-Morphine 20V, Negative-QTOFsplash10-014i-0000090000-e2fc2aed931f92c401462021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - y-Morphine 40V, Negative-QTOFsplash10-00kr-0000090000-ec077ce6ee35b4cfa18e2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB008420
KNApSAcK IDNot Available
Chemspider ID204595
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMorphine
METLIN IDNot Available
PubChem Compound234570
PDB IDNot Available
ChEBI ID169477
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. Lester PA, Traynor JR: Comparison of the in vitro efficacy of mu, delta, kappa and ORL1 receptor agonists and non-selective opioid agonists in dog brain membranes. Brain Res. 2006 Feb 16;1073-1074:290-6. Epub 2006 Jan 27. [PubMed:16443205 ]
  2. Brusick D, Matheson D, Jagannath D, Braude M, Brockman H, Hung C: Genetic screening of compounds used in drug abuse treatment. III. LAAM. Drug Chem Toxicol. 1981;4(1):19-35. [PubMed:6455284 ]
  3. Shook JE, Watkins WD, Camporesi EM: Differential roles of opioid receptors in respiration, respiratory disease, and opiate-induced respiratory depression. Am Rev Respir Dis. 1990 Oct;142(4):895-909. [PubMed:2171388 ]
  4. Pittman KA, Smyth RD, Mayol RF: Serum levels of butorphanol by radioimmunoassay. J Pharm Sci. 1980 Feb;69(2):160-3. [PubMed:7359315 ]
  5. Proksa B: Separation of morphine and its oxidation products by capillary zone electrophoresis. J Pharm Biomed Anal. 1999 Jun;20(1-2):179-83. [PubMed:10704021 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .