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 12:54:21 UTC |
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Update Date | 2021-09-26 23:07:39 UTC |
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HMDB ID | HMDB0253990 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | latrunculin B |
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Description | 15-hydroxy-15-(2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl)-5,10-dimethyl-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-3-one belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. 15-hydroxy-15-(2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl)-5,10-dimethyl-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-3-one is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Latrunculin b is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically latrunculin B 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 | CC1CCC2CC(CC(O)(O2)C2CSC(=O)N2)OC(=O)C=C(C)CCC=C1 InChI=1S/C20H29NO5S/c1-13-5-3-4-6-14(2)9-18(22)25-16-10-15(8-7-13)26-20(24,11-16)17-12-27-19(23)21-17/h3,5,9,13,15-17,24H,4,6-8,10-12H2,1-2H3,(H,21,23) |
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Synonyms | Not Available |
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Chemical Formula | C20H29NO5S |
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Average Molecular Weight | 395.51 |
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Monoisotopic Molecular Weight | 395.176644212 |
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IUPAC Name | 4-{15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl}-1,3-thiazolidin-2-one |
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Traditional Name | 4-{15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl}-1,3-thiazolidin-2-one |
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CAS Registry Number | Not Available |
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SMILES | CC1CCC2CC(CC(O)(O2)C2CSC(=O)N2)OC(=O)C=C(C)CCC=C1 |
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InChI Identifier | InChI=1S/C20H29NO5S/c1-13-5-3-4-6-14(2)9-18(22)25-16-10-15(8-7-13)26-20(24,11-16)17-12-27-19(23)21-17/h3,5,9,13,15-17,24H,4,6-8,10-12H2,1-2H3,(H,21,23) |
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InChI Key | NSHPHXHGRHSMIK-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Macrolides and analogues |
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Sub Class | Not Available |
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Direct Parent | Macrolides and analogues |
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Alternative Parents | |
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Substituents | - Macrolide
- Oxane
- Thiazolidine
- Enoate ester
- Alpha,beta-unsaturated carboxylic ester
- Carboxylic acid ester
- Hemiacetal
- Lactone
- Carbonic acid derivative
- Thiocarbamic acid derivative
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organoheterocyclic compound
- Azacycle
- Oxacycle
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Organonitrogen compound
- Organopnictogen compound
- Organic nitrogen compound
- Hydrocarbon derivative
- Carbonyl group
- 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 | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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latrunculin B,2TMS,isomer #1 | CC1=CC(=O)OC2CC(CCC(C)C=CCC1)OC(O[Si](C)(C)C)(C1CSC(=O)N1[Si](C)(C)C)C2 | 3415.9 | Semi standard non polar | 33892256 | latrunculin B,2TMS,isomer #1 | CC1=CC(=O)OC2CC(CCC(C)C=CCC1)OC(O[Si](C)(C)C)(C1CSC(=O)N1[Si](C)(C)C)C2 | 3159.0 | Standard non polar | 33892256 | latrunculin B,2TMS,isomer #1 | CC1=CC(=O)OC2CC(CCC(C)C=CCC1)OC(O[Si](C)(C)C)(C1CSC(=O)N1[Si](C)(C)C)C2 | 4134.1 | Standard polar | 33892256 | latrunculin B,2TBDMS,isomer #1 | CC1=CC(=O)OC2CC(CCC(C)C=CCC1)OC(O[Si](C)(C)C(C)(C)C)(C1CSC(=O)N1[Si](C)(C)C(C)(C)C)C2 | 3844.5 | Semi standard non polar | 33892256 | latrunculin B,2TBDMS,isomer #1 | CC1=CC(=O)OC2CC(CCC(C)C=CCC1)OC(O[Si](C)(C)C(C)(C)C)(C1CSC(=O)N1[Si](C)(C)C(C)(C)C)C2 | 3591.6 | Standard non polar | 33892256 | latrunculin B,2TBDMS,isomer #1 | CC1=CC(=O)OC2CC(CCC(C)C=CCC1)OC(O[Si](C)(C)C(C)(C)C)(C1CSC(=O)N1[Si](C)(C)C(C)(C)C)C2 | 4276.2 | Standard polar | 33892256 |
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