| Record Information |
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| Version | 5.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2013-07-09 16:07:51 UTC |
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| Update Date | 2021-09-14 15:19:57 UTC |
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| HMDB ID | HMDB0060929 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Dihydroisomorphine |
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| Description | Dihydroisomorphine is a metabolite of hydromorphone. Hydromorphone, a more common synonym for dihydromorphinone, commonly a hydrochloride (brand names Palladone, Dilaudid, and numerous others) is a very potent centrally acting analgesic drug of the opioid class. It is a derivative of morphine, to be specific, a hydrogenated ketone thereof and, therefore, a semi-synthetic drug. It is, in medical terms, an opioid analgesic and, in legal terms, a narcotic. (Wikipedia) |
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| Structure | [H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@H]2O)=CC=C3O InChI=1S/C17H21NO3/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/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10-,11+,13+,16-,17-/m0/s1 |
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| Synonyms | | Value | Source |
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| (5alpha,6beta)-4,5-Epoxy-17-methylmorphinan-3,6-diol | HMDB | | (5Α,6β)-4,5-epoxy-17-methylmorphinan-3,6-diol | HMDB | | 6beta-Hydromorphol | HMDB | | 6Β-hydromorphol | HMDB | | Dihydro-alpha-isomorphine | HMDB | | Dihydro-α-isomorphine | HMDB | | Dihydroisomorphine | HMDB |
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| Chemical Formula | C17H21NO3 |
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| Average Molecular Weight | 287.359 |
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| Monoisotopic Molecular Weight | 287.15214354 |
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| IUPAC Name | (1S,5R,13R,14R,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18)-triene-10,14-diol |
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| Traditional Name | (1S,5R,13R,14R,17R)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18)-triene-10,14-diol |
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| CAS Registry Number | 26626-12-0 |
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| SMILES | [H][C@@]12OC3=C4C(C[C@@]5([H])N(C)CC[C@@]14[C@@]5([H])CC[C@H]2O)=CC=C3O |
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| InChI Identifier | InChI=1S/C17H21NO3/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/h2,4,10-11,13,16,19-20H,3,5-8H2,1H3/t10-,11+,13+,16-,17-/m0/s1 |
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| InChI Key | IJVCSMSMFSCRME-NOSXKOESSA-N |
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| Chemical Taxonomy |
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| 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. |
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| Kingdom | Organic compounds |
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| Super Class | Alkaloids and derivatives |
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| Class | Morphinans |
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| Sub Class | Not Available |
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| Direct Parent | Morphinans |
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| Alternative Parents | |
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| Substituents | - Morphinan
- Phenanthrene
- Tetralin
- Coumaran
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Aralkylamine
- Piperidine
- Benzenoid
- Cyclic alcohol
- Secondary alcohol
- Tertiary aliphatic amine
- Tertiary amine
- Ether
- Oxacycle
- Azacycle
- Organoheterocyclic compound
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organopnictogen compound
- Amine
- Alcohol
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | Not Available |
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| Ontology |
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| Physiological effect | Not Available |
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| Disposition | |
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| Process | Not Available |
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| Role | Not Available |
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| Physical Properties |
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| State | Not Available |
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| Experimental Molecular Properties | | Property | Value | Reference |
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| Melting Point | Not Available | Not Available | | Boiling Point | Not Available | Not Available | | Water Solubility | Not Available | Not Available | | LogP | Not Available | Not Available |
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| Experimental Chromatographic Properties | Not Available |
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| Predicted Molecular Properties | |
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| Predicted Chromatographic Properties | Predicted Collision Cross Sections| Predictor | Adduct Type | CCS Value (Å2) | Reference |
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| DeepCCS | [M-2H]- | 208.278 | 30932474 | | DeepCCS | [M+Na]+ | 184.302 | 30932474 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| Dihydroisomorphine,1TMS,isomer #1 | CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@H](O[Si](C)(C)C)CC[C@H]3[C@H]1C5 | 2414.1 | Semi standard non polar | 33892256 | | Dihydroisomorphine,1TMS,isomer #2 | CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2[C@H](O)CC[C@H]3[C@H]1C5 | 2472.6 | Semi standard non polar | 33892256 | | Dihydroisomorphine,2TMS,isomer #1 | CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C)=C4O[C@H]2[C@H](O[Si](C)(C)C)CC[C@H]3[C@H]1C5 | 2480.4 | Semi standard non polar | 33892256 | | Dihydroisomorphine,1TBDMS,isomer #1 | CN1CC[C@]23C4=C5C=CC(O)=C4O[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@H]1C5 | 2677.9 | Semi standard non polar | 33892256 | | Dihydroisomorphine,1TBDMS,isomer #2 | CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2[C@H](O)CC[C@H]3[C@H]1C5 | 2744.8 | Semi standard non polar | 33892256 | | Dihydroisomorphine,2TBDMS,isomer #1 | CN1CC[C@]23C4=C5C=CC(O[Si](C)(C)C(C)(C)C)=C4O[C@H]2[C@H](O[Si](C)(C)C(C)(C)C)CC[C@H]3[C@H]1C5 | 2926.0 | Semi standard non polar | 33892256 |
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