Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:50 UTC |
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Update Date | 2022-03-07 02:51:43 UTC |
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HMDB ID | HMDB0014745 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Nafcillin |
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Description | Nafcillin is only found in individuals that have used or taken this drug. It is a semi-synthetic antibiotic related to penicillin. [PubChem]Penicillinase-resistant penicillins exert a bactericidal action against penicillin-susceptible microorganisms during the state of active multiplication. All penicillins inhibit the biosynthesis of the bacterial cell wall. |
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Structure | [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OCC)C=CC2=CC=CC=C12)C(O)=O InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1 |
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Synonyms | Value | Source |
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(2-Ethoxy-1-naphthalenyl)penicillin | ChEBI | (2-Ethoxy-1-naphthyl)penicillin | ChEBI | (2S,5R,6R)-6-[(2-Ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | ChEBI | (2S,5R,6R)-6-[(2-Ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | ChEBI | (2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | ChEBI | 6-(2-Ethoxy-1-naphthamido)penicillanic acid | ChEBI | Nafcilina | ChEBI | Nafcilline | ChEBI | Nafcillinum | ChEBI | Naphcillin | ChEBI | (2S,5R,6R)-6-[(2-Ethoxy-1-naphthoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | Generator | (2S,5R,6R)-6-[(2-Ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | Generator | (2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | Generator | 6-(2-Ethoxy-1-naphthamido)penicillanate | Generator | Nafcillin sodium salt | HMDB | Nafcil | HMDB | Nafcillin, monosodium salt, anhydrous | HMDB | Nafcillin sodium | HMDB | Nafcillin, sodium | HMDB | Naphthamidopenicillin | HMDB | Sodium nafcillin | HMDB | Sodium, nafcillin | HMDB |
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Chemical Formula | C21H22N2O5S |
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Average Molecular Weight | 414.475 |
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Monoisotopic Molecular Weight | 414.124942514 |
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IUPAC Name | (2S,5R,6R)-6-(2-ethoxynaphthalene-1-amido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid |
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Traditional Name | nafcillin |
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CAS Registry Number | 985-16-0 |
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SMILES | [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(OCC)C=CC2=CC=CC=C12)C(O)=O |
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InChI Identifier | InChI=1S/C21H22N2O5S/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27)/t15-,16+,19-/m1/s1 |
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InChI Key | GPXLMGHLHQJAGZ-JTDSTZFVSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond. |
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Kingdom | Organic compounds |
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Super Class | Organic acids and derivatives |
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Class | Carboxylic acids and derivatives |
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Sub Class | Amino acids, peptides, and analogues |
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Direct Parent | Dipeptides |
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Alternative Parents | |
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Substituents | - Alpha-dipeptide
- Penicillin
- 1-naphthalenecarboxylic acid or derivatives
- N-acyl-alpha amino acid or derivatives
- 1-naphthalenecarboxamide
- Alpha-amino acid or derivatives
- Naphthalene
- Penam
- Alkyl aryl ether
- Benzenoid
- Beta-lactam
- Tertiary carboxylic acid amide
- Thiazolidine
- Azetidine
- Secondary carboxylic acid amide
- Carboxamide group
- Lactam
- Carboxylic acid
- Ether
- Azacycle
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Dialkylthioether
- Hemithioaminal
- Thioether
- Organic oxygen compound
- Organopnictogen compound
- Organic oxide
- Carbonyl group
- Hydrocarbon derivative
- Organic nitrogen compound
- Organonitrogen compound
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 | Solid |
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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 | 0.017 g/L | Not Available | LogP | 3.3 | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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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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Nafcillin,1TMS,isomer #1 | CCOC1=CC=C2C=CC=CC2=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]12 | 3352.5 | Semi standard non polar | 33892256 | Nafcillin,1TMS,isomer #2 | CCOC1=CC=C2C=CC=CC2=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12)[Si](C)(C)C | 3331.2 | Semi standard non polar | 33892256 | Nafcillin,2TMS,isomer #1 | CCOC1=CC=C2C=CC=CC2=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C | 3292.0 | Semi standard non polar | 33892256 | Nafcillin,2TMS,isomer #1 | CCOC1=CC=C2C=CC=CC2=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C | 3232.1 | Standard non polar | 33892256 | Nafcillin,2TMS,isomer #1 | CCOC1=CC=C2C=CC=CC2=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C | 3960.8 | Standard polar | 33892256 | Nafcillin,1TBDMS,isomer #1 | CCOC1=CC=C2C=CC=CC2=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]12 | 3592.7 | Semi standard non polar | 33892256 | Nafcillin,1TBDMS,isomer #2 | CCOC1=CC=C2C=CC=CC2=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O)C(C)(C)S[C@H]12)[Si](C)(C)C(C)(C)C | 3541.0 | Semi standard non polar | 33892256 | Nafcillin,2TBDMS,isomer #1 | CCOC1=CC=C2C=CC=CC2=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C(C)(C)C | 3692.5 | Semi standard non polar | 33892256 | Nafcillin,2TBDMS,isomer #1 | CCOC1=CC=C2C=CC=CC2=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C(C)(C)C | 3672.5 | Standard non polar | 33892256 | Nafcillin,2TBDMS,isomer #1 | CCOC1=CC=C2C=CC=CC2=C1C(=O)N([C@@H]1C(=O)N2[C@@H](C(=O)O[Si](C)(C)C(C)(C)C)C(C)(C)S[C@H]12)[Si](C)(C)C(C)(C)C | 4099.4 | Standard polar | 33892256 |
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Spectra |
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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 - Nafcillin GC-MS (Non-derivatized) - 70eV, Positive | splash10-00dv-6559000000-476ab0db07d5480232f4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nafcillin GC-MS (1 TMS) - 70eV, Positive | splash10-00di-9423600000-8e41142db1f7e5fa26c3 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Nafcillin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , negative-QTOF | splash10-00di-0090000000-65901bf6905f35a84f24 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , negative-QTOF | splash10-006x-0090000000-517308aedcbe6210d46e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , negative-QTOF | splash10-00dl-8390000000-c3d759b208856f69cc83 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , negative-QTOF | splash10-00di-9210000000-3431effabf1bb94e4b20 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , negative-QTOF | splash10-00di-9200000000-8d4bae5167cd78d8f059 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , negative-QTOF | splash10-00di-9200000000-00cc24f858c63f2e6ac5 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , negative-QTOF | splash10-00di-9500000000-d447304de567843fa59a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , negative-QTOF | splash10-00xr-9500000000-fbdf096e0285a04fc391 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , negative-QTOF | splash10-0600-9300000000-976ae9913f6b5bc3f293 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , positive-QTOF | splash10-0002-0900000000-80966e1fb91b5e682c61 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , positive-QTOF | splash10-0002-0910000000-04c58a908553834f1db1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , positive-QTOF | splash10-00dj-0900000000-9ab759b60ea1b1ccb0a7 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , positive-QTOF | splash10-00di-0900000000-1e9b29becf8d78e99cfa | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , positive-QTOF | splash10-00xu-0900000000-dbba294d0a77e44851ed | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , positive-QTOF | splash10-014i-0900000000-9ac2c1b4dcbf3f1421d9 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , positive-QTOF | splash10-014i-1900000000-46b494a78d0ebbbc8079 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , positive-QTOF | splash10-014i-7900000000-dc8fdcb9afe3b064db85 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin LC-ESI-QFT , positive-QTOF | splash10-02ti-9300000000-847a94b299fb6ea1ddca | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Nafcillin 15V, Negative-QTOF | splash10-00di-0090000000-c9457bba69de43e462e3 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nafcillin 10V, Positive-QTOF | splash10-0900-0972300000-2fcf6e422525f1825413 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nafcillin 20V, Positive-QTOF | splash10-08fr-1950000000-56d3b44eb26e98206983 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nafcillin 40V, Positive-QTOF | splash10-08mi-2910000000-89a6a7cdc5521d4da995 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nafcillin 10V, Negative-QTOF | splash10-00di-0091000000-e9e7c7093646248dfa76 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nafcillin 20V, Negative-QTOF | splash10-00di-0293000000-58fe940779036ea82755 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Nafcillin 40V, Negative-QTOF | splash10-00bc-9751000000-54d52028a568bb18dd96 | 2016-08-03 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00607 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB00607 | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB00607 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 8634 |
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KEGG Compound ID | C07250 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Nafcillin |
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METLIN ID | Not Available |
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PubChem Compound | 8982 |
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PDB ID | Not Available |
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ChEBI ID | 7447 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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