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 16:15:09 UTC |
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Update Date | 2021-09-14 15:18:06 UTC |
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HMDB ID | HMDB0061049 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | 31-O-Demethyltacrolimus |
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Description | 31-O-Demethyltacrolimus is a metabolite of tacrolimus. Tacrolimus (also FK-506 or fujimycin, trade names Prograf, Advagraf, Protopic) is an immunosuppressive drug that is mainly used after allogeneic organ transplant to reduce the activity of the patient's immune system and so lower the risk of organ rejection. It is also used in a topical preparation in the treatment of atopic dermatitis, severe refractory uveitis after bone marrow transplants, exacerbations of minimal change disease, and the skin condition vitiligo. (Wikipedia) |
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Structure | [H][C@]12OC(O)(C(C)CC1OC)C(=O)C(=O)N1CCCCC1C(=O)OC(C(C)C(O)CC(=O)C(CC=C)\C=C(C)/CC(C)C[C@@H]2OC)C(\C)=C\C1CC[C@H](O)C(O)C1 InChI=1S/C43H67NO12/c1-9-12-30-18-24(2)17-25(3)19-36(53-7)39-37(54-8)21-27(5)43(52,56-39)40(49)41(50)44-16-11-10-13-31(44)42(51)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(48)22-29/h9,18,20,25,27-33,35-39,45-46,48,52H,1,10-17,19,21-23H2,2-8H3/b24-18-,26-20+/t25?,27?,28?,29?,30?,31?,32-,33?,35?,36-,37?,38?,39+,43?/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C43H67NO12 |
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Average Molecular Weight | 789.9916 |
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Monoisotopic Molecular Weight | 789.466326613 |
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IUPAC Name | (18Z,23S,24R)-12-[(1E)-1-[(4S)-3,4-dihydroxycyclohexyl]prop-1-en-2-yl]-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0⁴,⁹]octacos-18-ene-2,3,10,16-tetrone |
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Traditional Name | (18Z,23S,24R)-12-[(1E)-1-[(4S)-3,4-dihydroxycyclohexyl]prop-1-en-2-yl]-1,14-dihydroxy-23,25-dimethoxy-13,19,21,27-tetramethyl-17-(prop-2-en-1-yl)-11,28-dioxa-4-azatricyclo[22.3.1.0⁴,⁹]octacos-18-ene-2,3,10,16-tetrone |
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CAS Registry Number | Not Available |
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SMILES | [H][C@]12OC(O)(C(C)CC1OC)C(=O)C(=O)N1CCCCC1C(=O)OC(C(C)C(O)CC(=O)C(CC=C)\C=C(C)/CC(C)C[C@@H]2OC)C(\C)=C\C1CC[C@H](O)C(O)C1 |
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InChI Identifier | InChI=1S/C43H67NO12/c1-9-12-30-18-24(2)17-25(3)19-36(53-7)39-37(54-8)21-27(5)43(52,56-39)40(49)41(50)44-16-11-10-13-31(44)42(51)55-38(28(6)33(46)23-34(30)47)26(4)20-29-14-15-32(45)35(48)22-29/h9,18,20,25,27-33,35-39,45-46,48,52H,1,10-17,19,21-23H2,2-8H3/b24-18-,26-20+/t25?,27?,28?,29?,30?,31?,32-,33?,35?,36-,37?,38?,39+,43?/m0/s1 |
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InChI Key | VHOPGJHKSPGXIZ-BDWLBPCDSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as macrolide lactams. These are cyclic polyketides containing both a cyclic amide and a cyclic ester group. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Macrolide lactams |
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Sub Class | Not Available |
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Direct Parent | Macrolide lactams |
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Alternative Parents | |
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Substituents | - Macrolide lactam
- Alpha-amino acid ester
- Macrolide
- Alpha-amino acid or derivatives
- Cyclohexanol
- Oxane
- Piperidine
- Cyclic alcohol
- Tertiary carboxylic acid amide
- Cyclic ketone
- Secondary alcohol
- Carboxamide group
- Carboxylic acid ester
- Hemiacetal
- Ketone
- Lactam
- Lactone
- Organoheterocyclic compound
- Azacycle
- Carboxylic acid derivative
- Oxacycle
- Dialkyl ether
- Ether
- Monocarboxylic acid or derivatives
- Organopnictogen compound
- Alcohol
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Organonitrogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Aliphatic heteropolycyclic compound
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Molecular Framework | Aliphatic 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 SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - 31-O-Demethyltacrolimus GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ab9-4000000900-be7de4c3a100d363b391 | 2017-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 31-O-Demethyltacrolimus GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 31-O-Demethyltacrolimus GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 31-O-Demethyltacrolimus GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 31-O-Demethyltacrolimus GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 31-O-Demethyltacrolimus GC-MS (TMS_1_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - 31-O-Demethyltacrolimus GC-MS (TMS_1_6) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 31-O-Demethyltacrolimus 10V, Positive-QTOF | splash10-00dl-0100000900-ddf2d1afda7b51d9073f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 31-O-Demethyltacrolimus 20V, Positive-QTOF | splash10-0uk9-1300002900-461d2622782eb7ba90cf | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 31-O-Demethyltacrolimus 40V, Positive-QTOF | splash10-0pbi-7100006900-8cc45c8178d9583a2822 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 31-O-Demethyltacrolimus 10V, Negative-QTOF | splash10-000i-0000000900-50a43317e78859663695 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 31-O-Demethyltacrolimus 20V, Negative-QTOF | splash10-00dr-0000000900-92d95ae1db34b284bc43 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 31-O-Demethyltacrolimus 40V, Negative-QTOF | splash10-00ec-4000001900-8c1479c63c5d2c7cc055 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 31-O-Demethyltacrolimus 10V, Negative-QTOF | splash10-000i-0000000900-490c0ad5dcb025d9db5e | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 31-O-Demethyltacrolimus 20V, Negative-QTOF | splash10-000i-0000001900-37ac088da85fa0745196 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 31-O-Demethyltacrolimus 40V, Negative-QTOF | splash10-01pc-0500009500-555179e9c32f93ceb06b | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 31-O-Demethyltacrolimus 10V, Positive-QTOF | splash10-0fdo-0000000900-7bb51da732a52d98e71c | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 31-O-Demethyltacrolimus 20V, Positive-QTOF | splash10-0f6x-0000000900-5b15f80f825f9c10de91 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 31-O-Demethyltacrolimus 40V, Positive-QTOF | splash10-03di-4000000900-b67353b0affcdb1fe285 | 2021-09-23 | Wishart Lab | View Spectrum |
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