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Human Metabolome Database Version 3.5

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Showing metabocard for Morphinone (HMDB03563)

Record Information
Version 3.5
Creation Date 2006-08-12 17:47:18 -0600
Update Date 2013-02-08 17:12:39 -0700
HMDB ID HMDB03563
Secondary Accession Numbers None
Metabolite Identification
Common Name Morphinone
Description Morphinone is a very strong opioid. It is an intermediary substance in synthesises of semi-synthetic opioids, e.g. Naloxone and Naltrexone and Oxycodone.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
    Chemical Formula C17H17NO3
    Average Molecular Weight 283.3218
    Monoisotopic Molecular Weight 283.120843415
    IUPAC Name (1S,5R,13R,17R)-10-hydroxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-one
    Traditional IUPAC Name morphinone
    CAS Registry Number 467-02-7
    SMILES [H][C@@]12OC3=C(O)C=CC4=C3[C@@]11CCN(C)[C@H](C4)[C@]1([H])C=CC2=O
    InChI Identifier InChI=1S/C17H17NO3/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/h2-5,10-11,16,19H,6-8H2,1H3/t10-,11+,16-,17-/m0/s1
    InChI Key PFBSOANQDDTNGJ-YNHQPCIGSA-N
    Chemical Taxonomy
    Kingdom Organic Compounds
    Super Class Alkaloids and Derivatives
    Class Morphinans
    Sub Class N/A
    Other Descriptors
    • Aromatic Heteropolycyclic Compounds
    • Isoquinoline alkaloids(KEGG)
    • morphinane alkaloid(ChEBI)
    Substituents
    • Alkyl Aryl Ether
    • Benzofuran
    • Cyclohexene
    • Dihydrofuran
    • Isoquinolone
    • Ketone
    • Phenol
    • Phenol Derivative
    • Piperidine
    • Tertiary Aliphatic Amine (Trialkylamine)
    • Tetralin
    Direct Parent Morphinans
    Ontology
    Status Expected and Not Quantified
    Origin
    • Endogenous
    Biofunction Not Available
    Application Not Available
    Cellular locations Not Available
    Physical Properties
    State Solid
    Experimental Properties
    Property Value Reference
    Melting Point Not Available Not Available
    Boiling Point Not Available Not Available
    Water Solubility Not Available Not Available
    LogP Not Available Not Available
    Predicted Properties
    Property Value Source
    Water Solubility 3.48 g/L ALOGPS
    LogP 1.44 ALOGPS
    LogP 1.66 ChemAxon
    LogS -1.91 ALOGPS
    pKa (strongest acidic) 10.1 ChemAxon
    pKa (strongest basic) 8.46 ChemAxon
    Hydrogen Acceptor Count 4 ChemAxon
    Hydrogen Donor Count 1 ChemAxon
    Polar Surface Area 49.77 A2 ChemAxon
    Rotatable Bond Count 0 ChemAxon
    Refractivity 79.36 ChemAxon
    Polarizability 29.34 ChemAxon
    Formal Charge 0 ChemAxon
    Physiological Charge 1 ChemAxon
    Spectra
    Not Available
    Biological Properties
    Cellular Locations Not Available
    Biofluid Locations Not Available
    Tissue Location Not Available
    Pathways Not Available
    Normal Concentrations
    Not Available
    Abnormal Concentrations
    Not Available
    Associated Disorders and Diseases
    Disease References None
    Associated OMIM IDs None
    DrugBank ID Not Available
    DrugBank Metabolite ID Not Available
    Phenol Explorer Compound ID Not Available
    Phenol Explorer Metabolite ID Not Available
    FoodDB ID FDB023197
    KNApSAcK ID Not Available
    Chemspider ID 4573586 Link_out
    KEGG Compound ID C01735 Link_out
    BioCyc ID MORPHINONE Link_out
    BiGG ID Not Available
    Wikipedia Link Morphinone Link_out
    NuGOwiki Link HMDB03563 Link_out
    Metagene Link HMDB03563 Link_out
    METLIN ID 6955 Link_out
    PubChem Compound 5459823 Link_out
    PDB ID Not Available
    ChEBI ID 16315 Link_out
    References
    Synthesis Reference Rapoport, Henry; Baker, Don R.; Reist, Helen N. Morphinone. Journal of Organic Chemistry (1957), 22 1489-92.
    Material Safety Data Sheet (MSDS) Not Available
    General References
    1. Todaka T, Ishida T, Kita H, Narimatsu S, Yamano S: Bioactivation of morphine in human liver: isolation and identification of morphinone, a toxic metabolite. Biol Pharm Bull. 2005 Jul;28(7):1275-80. Pubmed: 15997113 Link_out