Record Information |
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Version | 1.0 |
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Created at | 2020-12-09 00:54:51 UTC |
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Updated at | 2021-07-15 16:47:17 UTC |
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NP-MRD ID | NP0003752 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Epothilone D |
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Provided By | NPAtlas |
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Description | Epothilone D is also known as epo D or KOS 862. Epothilone D is found in Sorangium cellulosum and Sorangium cellulosum So.ce90/B2. It was first documented in 2000 (PMID: 10831849). Based on a literature review a significant number of articles have been published on Epothilone D (PMID: 11473410) (PMID: 15242255) (PMID: 15788167) (PMID: 15868148). |
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Structure | [H]O[C@]1([H])[C@]([H])(C(=O)C(C([H])([H])[H])(C([H])([H])[H])[C@@]([H])(O[H])C([H])([H])C(=O)O[C@]([H])(C(=C(/[H])C2=C([H])SC(=N2)C([H])([H])[H])\C([H])([H])[H])C([H])([H])\C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])([H])[C@]1([H])C([H])([H])[H])C([H])([H])[H] InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1 |
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Synonyms | Value | Source |
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(-)-Desoxyepothilone b | ChEBI | (-)-Epothilone D | ChEBI | 12,13-Deoxyepothilone b | ChEBI | 12,13-Desoxyepothilone b | ChEBI | Epo D | ChEBI | KOS 862 | ChEBI | KOS-862 | ChEBI | NSC 703147 | ChEBI | NSC-703147 | ChEBI | Desoxyepothilone b | Kegg | DEpoB CPD | MeSH | Epothilon D | MeSH | Epothilone b, desoxy | MeSH | Epothiolone D | MeSH |
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Chemical Formula | C27H41NO5S |
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Average Mass | 491.6830 Da |
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Monoisotopic Mass | 491.27054 Da |
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IUPAC Name | (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione |
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Traditional Name | epothilone D |
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CAS Registry Number | Not Available |
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SMILES | C[C@H]1CCC\C(C)=C/C[C@H](OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@H]1O)C(\C)=C\C1=CSC(C)=N1 |
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InChI Identifier | InChI=1S/C27H41NO5S/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)33-22(12-11-16)18(3)13-21-15-34-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1 |
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InChI Key | XOZIUKBZLSUILX-GIQCAXHBSA-N |
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Experimental Spectra |
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| Not Available | Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as epothilones and analogues. These are macrolides consisting of a 16-member lactone ring conjugated at the carbon 16 with a 1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl group. Some epothilone analogues containing a lactam ring instead of the lactone ring. |
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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 | Epothilones and analogues |
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Direct Parent | Epothilones and analogues |
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Alternative Parents | |
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Substituents | - Epothilone
- 2,4-disubstituted 1,3-thiazole
- Azole
- Heteroaromatic compound
- Thiazole
- Carboxylic acid ester
- Ketone
- Lactone
- Secondary alcohol
- Cyclic ketone
- Carboxylic acid derivative
- Oxacycle
- Monocarboxylic acid or derivatives
- Azacycle
- Organoheterocyclic compound
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organopnictogen compound
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Organic oxygen compound
- Carbonyl group
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | - Macrolides and lactone polyketides (C12039 )
- Macrolides and lactone polyketides (LMPK04000001 )
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Physical Properties |
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State | Not Available |
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Experimental 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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Predicted Properties | |
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General References | - Hardt IH, Steinmetz H, Gerth K, Sasse F, Reichenbach H, Hofle G: New natural epothilones from Sorangium cellulosum, strains So ce90/B2 and So ce90/D13: isolation, structure elucidation, and SAR studies. J Nat Prod. 2001 Jul;64(7):847-56. doi: 10.1021/np000629f. [PubMed:11473410 ]
- Julien B, Shah S, Ziermann R, Goldman R, Katz L, Khosla C: Isolation and characterization of the epothilone biosynthetic gene cluster from Sorangium cellulosum. Gene. 2000 May 16;249(1-2):153-60. doi: 10.1016/s0378-1119(00)00149-9. [PubMed:10831849 ]
- Kolman A: Epothilone D (Kosan/Roche). Curr Opin Investig Drugs. 2004 Jun;5(6):657-67. [PubMed:15242255 ]
- Broadrup RL, Sundar HM, Swindell CS: Total synthesis of 12,13-desoxyepothilone B (Epothilone D). Bioorg Chem. 2005 Apr;33(2):116-33. doi: 10.1016/j.bioorg.2004.11.002. Epub 2004 Dec 15. [PubMed:15788167 ]
- Wang H, Wang Z, Wang S, Li M, Nan L, Rhie JK, Covey JM, Zhang R, Hill DL: Preclinical pharmacology of epothilone D, a novel tubulin-stabilizing antitumor agent. Cancer Chemother Pharmacol. 2005 Sep;56(3):255-60. doi: 10.1007/s00280-004-0965-0. Epub 2005 May 3. [PubMed:15868148 ]
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