Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:51 UTC |
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Update Date | 2019-01-11 19:35:00 UTC |
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HMDB ID | HMDB0015094 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Methylprednisolone |
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Description | Methylprednisolone is only found in individuals that have used or taken this drug. It is a prednisolone derivative with similar anti-inflammatory action. [PubChem]Unbound glucocorticoids cross cell membranes and bind with high affinity to specific cytoplasmic receptors, modifying transcription and protein synthesis. By this mechanism, glucocorticoids can inhibit leukocyte infiltration at the site of inflammation, interfere with mediators of inflammatory response, and suppress humoral immune responses. The antiinflammatory actions of corticosteroids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes. |
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Structure | |
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Synonyms | Value | Source |
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(6alpha,11beta)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione | ChEBI | 1-dehydro-6alpha-Methylhydrocortisone | ChEBI | 6alpha-Methyl-11beta,17alpha,21-triol-1,4-pregnadiene-3,20-dione | ChEBI | Delta(1)-6alpha-Methylhydrocortisone | ChEBI | Medrate | ChEBI | Medrol | ChEBI | Medrone | ChEBI | Methylprednisolon | ChEBI | Methylprednisolonum | ChEBI | Metilprednisolona | ChEBI | Solomet | ChEBI | Urbason | ChEBI | (6a,11b)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione | Generator | (6α,11β)-11,17,21-trihydroxy-6-methylpregna-1,4-diene-3,20-dione | Generator | 1-dehydro-6a-Methylhydrocortisone | Generator | 1-dehydro-6α-methylhydrocortisone | Generator | 6a-Methyl-11b,17a,21-triol-1,4-pregnadiene-3,20-dione | Generator | 6α-methyl-11β,17α,21-triol-1,4-pregnadiene-3,20-dione | Generator | delta(1)-6a-Methylhydrocortisone | Generator | δ(1)-6α-methylhydrocortisone | Generator | Medric acid | Generator | δ(1)-6a-methylhydrocortisone | Generator | 6alpha-Methylprednisolone | HMDB | Methyleneprednisolone | HMDB | Metilprednisolone | HMDB | 6 Methylprednisolone | MeSH | 6-Methylprednisolone | MeSH | Metipred | MeSH |
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Chemical Formula | C22H30O5 |
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Average Molecular Weight | 374.4706 |
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Monoisotopic Molecular Weight | 374.20932407 |
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IUPAC Name | (1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadeca-3,6-dien-5-one |
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Traditional Name | methylprednisolone |
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CAS Registry Number | 83-43-2 |
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SMILES | [H][C@@]12CC[C@](O)(C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])C[C@H](C)C2=CC(=O)C=C[C@]12C |
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InChI Identifier | InChI=1S/C22H30O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h4,6,9,12,14-15,17,19,23,25,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,17-,19+,20-,21-,22-/m0/s1 |
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InChI Key | VHRSUDSXCMQTMA-PJHHCJLFSA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Hydroxysteroids |
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Direct Parent | 21-hydroxysteroids |
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Alternative Parents | |
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Substituents | - Progestogin-skeleton
- 21-hydroxysteroid
- 20-oxosteroid
- Pregnane-skeleton
- 3-oxo-delta-1,4-steroid
- 3-oxosteroid
- Oxosteroid
- 11-beta-hydroxysteroid
- 11-hydroxysteroid
- 17-hydroxysteroid
- Delta-1,4-steroid
- Cyclic alcohol
- Tertiary alcohol
- Alpha-hydroxy ketone
- Ketone
- Secondary alcohol
- Cyclic ketone
- Primary alcohol
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Carbonyl group
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | - 6-methylprednisolone (CHEBI:6888 )
- C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030178 )
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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 232.5 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.11 g/L | Not Available | LogP | 1.5 | Not Available |
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Predicted Properties | |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a5c-4897000000-e8a5119b3469a050dd85 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-004i-1325090000-5d0a8d05c100c594a651 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0bti-0896000000-86854a3fa2cb3c3bde0b | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0a4r-0796000000-b0070da713077c3f7975 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-01p9-3950000000-b938f656c358e1e42bb5 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0a6r-0019000000-3a4955cf7cc34e1e8d0f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-0k9i-0696000000-003c4527b983cf71aefd | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-01p9-0980000000-e5097669b38e84057a0f | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-01p9-0960000000-ef914702163187cc80af | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-06y9-0940000000-54b01b6c04c68be3f1b3 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4i-0009000000-3fe2869617af3697e2ed | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4i-0009000000-8ad4f169606968256614 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0f79-0895000000-29d1cbf49bb2b32c5a98 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-01p9-0940000000-baa402ac94c228229ea2 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-01p9-0910000000-5cf9fb219d798a9316f4 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4r-0910000000-a2d2af7f573229dc3147 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0006-2900000000-a01d5bfe926dc48e6e4c | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0a4i-0019000000-11519ee9583104c00505 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-0gw0-0974000000-af5d4ebce055ce6efb23 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-01p9-0960000000-22e2342fcec2bf1cd833 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITFT , positive | splash10-01p9-0920000000-63759535c53af1efb13f | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a6r-0019000000-0cb8333360b09d8df53e | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4r-0249000000-56520a54507e1870e5a6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01c1-1793000000-d51395bd0972f5b8c5ef | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0009000000-d97cc17b3e3a9c57c8ff | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-2029000000-2b2ea4b2dc572fa1808b | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-8096000000-fe46a5f1c12f4f84faf3 | View in MoNA |
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