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Showing metabocard for Hydromorphone (HMDB0014472)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2020-02-26 21:39:43 UTC
HMDB IDHMDB0014472
Secondary Accession Numbers
  • HMDB14472
Metabolite Identification
Common NameHydromorphone
DescriptionHydromorphone is only found in individuals that have used or taken this drug. It is an opioid analgesic derived from morphine and used mainly as an analgesic. It has a shorter duration of action and is more potent than morphine. [PubChem]Hydromorphone is a narcotic analgesic; its principal therapeutic effect is relief of pain. Hydromorphone interacts predominantly with the opioid mu-receptors. These mu-binding sites are discretely distributed in the human brain, with high densities in the posterior amygdala, hypothalamus, thalamus, nucleus caudatus, putamen, and certain cortical areas. They are also found on the terminal axons of primary afferents within laminae I and II (substantia gelatinosa) of the spinal cord and in the spinal nucleus of the trigeminal nerve. In clinical settings, Hydromorphone exerts its principal pharmacological effect on the central nervous system and gastrointestinal tract. Hydromorphone also binds with kappa-receptors which are thought to mediate spinal analgesia, miosis and sedation.
Structure
Data?1582753183
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-(5R)-4,5-Epoxy-3-hydroxy-9alpha-methylmorphinan-6-oneChEBI
4,5-Epoxy-3-hydroxy-17-methylmorphinan-6-oneChEBI
4,5alpha-Epoxy-3-hydroxy-17-methyl-6-morphinanoneChEBI
6-Deoxy-7,8-dihydro-6-oxomorphineChEBI
7,8-DihydromorphinoneChEBI
DihydromorfinonChEBI
DihydromorphinoneChEBI
DimorphoneChEBI
HidromorfonaChEBI
HydromorfonaChEBI
HydromorphonumChEBI
IdromorfoneChEBI
(-)-(5R)-4,5-Epoxy-3-hydroxy-9a-methylmorphinan-6-oneGenerator
(-)-(5R)-4,5-Epoxy-3-hydroxy-9α-methylmorphinan-6-oneGenerator
4,5a-Epoxy-3-hydroxy-17-methyl-6-morphinanoneGenerator
4,5Α-epoxy-3-hydroxy-17-methyl-6-morphinanoneGenerator
HydromorphonHMDB
Hydromorphone hydrochlorideHMDB
LaudaconHMDB
DilaudidHMDB
PalladoneHMDB
Chemical FormulaC17H19NO3
Average Molecular Weight285.3377
Monoisotopic Molecular Weight285.136493479
IUPAC Name(1S,5R,13R,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-one
Traditional Namehydromorphone
CAS Registry Number466-99-9
SMILES
[H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@]([H])(C4)[C@]1([H])CCC2=O
InChI Identifier
InChI=1S/C17H19NO3/c1-18-7-6-17-10-3-5-13(20)16(17)21-15-12(19)4-2-9(14(15)17)8-11(10)18/h2,4,10-11,16,19H,3,5-8H2,1H3/t10-,11+,16-,17-/m0/s1
InChI KeyWVLOADHCBXTIJK-YNHQPCIGSA-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
  • Morphinan
  • Phenanthrene
  • Isoquinolone
  • Tetralin
  • Coumaran
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Aralkylamine
  • Piperidine
  • Benzenoid
  • Ketone
  • Tertiary amine
  • Tertiary aliphatic amine
  • Oxacycle
  • Ether
  • Azacycle
  • Organoheterocyclic compound
  • Amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point266 - 267 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.39 g/LNot Available
LogP0.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.39 g/LALOGPS
logP1.69ALOGPS
logP1.62ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)10.11ChemAxon
pKa (Strongest Basic)8.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity78.26 m³·mol⁻¹ChemAxon
Polarizability30.02 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0adl-2090000000-1b72d2e162be578cb94dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-6039000000-d29846cb85959ad1cc2cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-052fc44835772dd50b65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-711917845b2129c2d3e3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-7090000000-8d20bdd275a62a96fd87Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-a0979bf03853322bb9f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-2cd300544d508b429beeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ou-1290000000-c40fe8399a0aae44bc33Spectrum
MSMass Spectrum (Electron Ionization)splash10-002r-6960000000-9f3d9b17d56e032d76c5Spectrum
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 DB00327 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00327 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 IDDB00327
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4447624
KEGG Compound IDC07042
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDihydromorphinone
METLIN IDNot Available
PubChem Compound5284570
PDB IDNot Available
ChEBI ID5790
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Vallner JJ, Stewart JT, Kotzan JA, Kirsten EB, Honigberg IL: Pharmacokinetics and bioavailability of hydromorphone following intravenous and oral administration to human subjects. J Clin Pharmacol. 1981 Apr;21(4):152-6. [PubMed:6165742 ]
  2. Coda BA, Rudy AC, Archer SM, Wermeling DP: Pharmacokinetics and bioavailability of single-dose intranasal hydromorphone hydrochloride in healthy volunteers. Anesth Analg. 2003 Jul;97(1):117-23, table of contents. [PubMed:12818953 ]