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    CAS 78715-23-8

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    CAS 78715-23-8
    Also known as: Des(cyclopropylmethyl)buprenorphine, 78715-23-8, 7e53b4o073, N-desalkylbuprenorphine, (1s,2s,6r,14r,15r,16r)-16-[(2s)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol, Unii-7e53b4o073
    Molecular Formula
    C25H35NO4
    Molecular Weight
    413.5  g/mol
    InChI Key
    YOYLLRBMGQRFTN-IOMBULRVSA-N
    FDA UNII
    7E53B4O073
    1 2D Structure

    CAS 78715-23-8

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,2S,6R,14R,15R,16R)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol
    2.1.2 InChI
    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
    2.1.3 InChI Key
    YOYLLRBMGQRFTN-IOMBULRVSA-N
    2.1.4 Canonical SMILES
    CC(C)(C)C(C)(C1CC23CCC1(C4C25CCNC3CC6=C5C(=C(C=C6)O)O4)OC)O
    2.1.5 Isomeric SMILES
    C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN[C@@H]3CC6=C5C(=C(C=C6)O)O4)OC)(C(C)(C)C)O
    2.2 Other Identifiers
    2.2.1 UNII
    7E53B4O073
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Des(cyclopropylmethyl)buprenorphine

    2. N-desalkylbuprenorphine

    2.3.2 Depositor-Supplied Synonyms

    1. Des(cyclopropylmethyl)buprenorphine

    2. 78715-23-8

    3. 7e53b4o073

    4. N-desalkylbuprenorphine

    5. (1s,2s,6r,14r,15r,16r)-16-[(2s)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol

    6. Unii-7e53b4o073

    7. Chembl1743323

    8. Schembl14408877

    9. Dtxsid60891436

    10. Chebi:172315

    11. Zinc6031944

    12. 6,14-ethenomorphinan-7-methanol, Alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-, (alphas,5alpha,7alpha)-

    13. Q63396332

    14. 6,14-ethenomorphinan-3-ol, 4,5-epoxy-18,19-dihydro-18-[(1s)-1-hydroxy-1,2,2-trimethylpropyl]-6-methoxy-, (5alpha,6beta,14beta,18r)-

    15. 6,14-ethenomorphinan-7-methanol, Alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-, (alphas,5alpha,7alpha)- (9ci)

    16. 6,14-ethenomorphinan-7-methanol, Alpha-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3-hydroxy-6-methoxy-alpha-methyl-, [5alpha,7alpha(s)]-

    17. Norbuprenorphine Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

    2.4 Create Date
    2005-06-01
    3 Chemical and Physical Properties
    Molecular Weight 413.5 g/mol
    Molecular Formula C25H35NO4
    XLogP33.8
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count3
    Exact Mass413.25660860 g/mol
    Monoisotopic Mass413.25660860 g/mol
    Topological Polar Surface Area71 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity752
    Isotope Atom Count0
    Defined Atom Stereocenter Count7
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Metabolism/Metabolites

    Norbuprenorphine has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-[[(1S,2S,6R,14R,15R,16R)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-yl]oxy]oxane-2-carboxylic acid.

    Norbuprenorphine is a known human metabolite of Buprenorphine.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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