Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-11 18:48:55 UTC |
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Update Date | 2021-09-26 23:14:19 UTC |
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HMDB ID | HMDB0257757 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate |
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Description | 4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl 2-{[2-(diethylamino)ethyl]sulfanyl}acetate belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety. 4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl 2-{[2-(diethylamino)ethyl]sulfanyl}acetate is a very strong basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). [(2r,3s,4s,6r,7s,8r)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | CCN(CC)CCSCC(=O)OC1CC(C)(C=C)C(O)C(C)C23CCC(=O)C2C1(C)C(C)CC3 InChI=1S/C28H47NO4S/c1-8-26(6)17-22(33-23(31)18-34-16-15-29(9-2)10-3)27(7)19(4)11-13-28(20(5)25(26)32)14-12-21(30)24(27)28/h8,19-20,22,24-25,32H,1,9-18H2,2-7H3 |
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Synonyms | Value | Source |
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4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0,]tetradecan-6-yl 2-{[2-(diethylamino)ethyl]sulfanyl}acetic acid | Generator | 4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0,]tetradecan-6-yl 2-{[2-(diethylamino)ethyl]sulphanyl}acetate | Generator | 4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0,]tetradecan-6-yl 2-{[2-(diethylamino)ethyl]sulphanyl}acetic acid | Generator | 2-(Diethylaminoethyl)thioacetoxymutilin | MeSH | Dynamutilin | MeSH | Tiamulin fumarate | MeSH | Tiamutin | MeSH | Tiamulin hydrochloride | MeSH | Tiamulin fumarate (1:1), (3as-(3aalpha,4beta,5alpha,6alpha,8beta,9alpha,9abeta,10S*))-isomer | MeSH |
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Chemical Formula | C28H47NO4S |
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Average Molecular Weight | 493.75 |
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Monoisotopic Molecular Weight | 493.322580171 |
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IUPAC Name | 4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl 2-{[2-(diethylamino)ethyl]sulfanyl}acetate |
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Traditional Name | 4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0¹,⁸]tetradecan-6-yl 2-{[2-(diethylamino)ethyl]sulfanyl}acetate |
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CAS Registry Number | Not Available |
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SMILES | CCN(CC)CCSCC(=O)OC1CC(C)(C=C)C(O)C(C)C23CCC(=O)C2C1(C)C(C)CC3 |
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InChI Identifier | InChI=1S/C28H47NO4S/c1-8-26(6)17-22(33-23(31)18-34-16-15-29(9-2)10-3)27(7)19(4)11-13-28(20(5)25(26)32)14-12-21(30)24(27)28/h8,19-20,22,24-25,32H,1,9-18H2,2-7H3 |
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InChI Key | UURAUHCOJAIIRQ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Diterpenoids |
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Direct Parent | Pleuromutilin and derivatives |
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Alternative Parents | |
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Substituents | - Pleuromutilin
- Amino acid or derivatives
- Carboxylic acid ester
- Ketone
- Secondary alcohol
- Tertiary amine
- Tertiary aliphatic amine
- Dialkylthioether
- Sulfenyl compound
- Monocarboxylic acid or derivatives
- Thioether
- Carboxylic acid derivative
- Organosulfur compound
- Organooxygen compound
- Organonitrogen compound
- Organic oxide
- Amine
- Organopnictogen compound
- Organic nitrogen compound
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- Organic oxygen compound
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Not Available | 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 IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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[(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate | CCN(CC)CCSCC(=O)OC1CC(C)(C=C)C(O)C(C)C23CCC(=O)C2C1(C)C(C)CC3 | 3467.9 | Semi standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate | CCN(CC)CCSCC(=O)OC1CC(C)(C=C)C(O)C(C)C23CCC(=O)C2C1(C)C(C)CC3 | 3468.0 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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[(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,1TMS,isomer #2 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C3=C(O[Si](C)(C)C)CCC3(CCC2C)C(C)C1O | 3371.7 | Semi standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,1TMS,isomer #2 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C3=C(O[Si](C)(C)C)CCC3(CCC2C)C(C)C1O | 3297.1 | Standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,1TMS,isomer #2 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C3=C(O[Si](C)(C)C)CCC3(CCC2C)C(C)C1O | 4006.9 | Standard polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,2TMS,isomer #1 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C3=C(O[Si](C)(C)C)CCC3(CCC2C)C(C)C1O[Si](C)(C)C | 3339.4 | Semi standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,2TMS,isomer #1 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C3=C(O[Si](C)(C)C)CCC3(CCC2C)C(C)C1O[Si](C)(C)C | 3318.7 | Standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,2TMS,isomer #1 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C3=C(O[Si](C)(C)C)CCC3(CCC2C)C(C)C1O[Si](C)(C)C | 3798.4 | Standard polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,2TMS,isomer #2 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C(C)CCC3(CC=C(O[Si](C)(C)C)C32)C(C)C1O[Si](C)(C)C | 3416.1 | Semi standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,2TMS,isomer #2 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C(C)CCC3(CC=C(O[Si](C)(C)C)C32)C(C)C1O[Si](C)(C)C | 3237.7 | Standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,2TMS,isomer #2 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C(C)CCC3(CC=C(O[Si](C)(C)C)C32)C(C)C1O[Si](C)(C)C | 3764.6 | Standard polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,1TBDMS,isomer #3 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C(C)CCC3(CC=C(O[Si](C)(C)C(C)(C)C)C32)C(C)C1O | 3723.3 | Semi standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,1TBDMS,isomer #3 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C(C)CCC3(CC=C(O[Si](C)(C)C(C)(C)C)C32)C(C)C1O | 3359.1 | Standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,1TBDMS,isomer #3 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C(C)CCC3(CC=C(O[Si](C)(C)C(C)(C)C)C32)C(C)C1O | 4087.5 | Standard polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,2TBDMS,isomer #1 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C3=C(O[Si](C)(C)C(C)(C)C)CCC3(CCC2C)C(C)C1O[Si](C)(C)C(C)(C)C | 3833.7 | Semi standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,2TBDMS,isomer #1 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C3=C(O[Si](C)(C)C(C)(C)C)CCC3(CCC2C)C(C)C1O[Si](C)(C)C(C)(C)C | 3696.0 | Standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,2TBDMS,isomer #1 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C3=C(O[Si](C)(C)C(C)(C)C)CCC3(CCC2C)C(C)C1O[Si](C)(C)C(C)(C)C | 3978.7 | Standard polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,2TBDMS,isomer #2 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C(C)CCC3(CC=C(O[Si](C)(C)C(C)(C)C)C32)C(C)C1O[Si](C)(C)C(C)(C)C | 3913.5 | Semi standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,2TBDMS,isomer #2 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C(C)CCC3(CC=C(O[Si](C)(C)C(C)(C)C)C32)C(C)C1O[Si](C)(C)C(C)(C)C | 3528.3 | Standard non polar | 33892256 | [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate,2TBDMS,isomer #2 | C=CC1(C)CC(OC(=O)CSCCN(CC)CC)C2(C)C(C)CCC3(CC=C(O[Si](C)(C)C(C)(C)C)C32)C(C)C1O[Si](C)(C)C(C)(C)C | 3937.1 | Standard polar | 33892256 |
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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 - [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate GC-MS (Non-derivatized) - 70eV, Positive | splash10-0udi-9602500000-bf18fb774b3b020ec18b | 2021-09-23 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - [(2R,3S,4S,6R,7S,8R)-4-Ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxo-6-tricyclo[5.4.3.01,8]tetradecanyl] 2-[2-(diethylamino)ethylsulfanyl]acetate GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-11-05 | Wishart Lab | View Spectrum |
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