Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 17:36:28 UTC |
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Update Date | 2022-03-07 02:52:31 UTC |
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HMDB ID | HMDB0030381 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Roquefortine |
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Description | Roquefortine belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Roquefortine C is a mycotoxin that belongs to a class of naturally occurring 2,5-diketopiperazines produced by various fungi, particularly species from the genus Penicillium. Roquefortine is a very strong basic compound (based on its pKa). Outside of the human body, roquefortine has been detected, but not quantified in, milk and milk products. This could make roquefortine a potential biomarker for the consumption of these foods. It was first isolated from a strain of Penicillium roqueforti, a species commercially used as a source of proteolytic and lipolytic enzymes during maturation of the blue-veined cheeses, Roquefort, Danish Blue, Stilton and Gorgonzola. Although it is a potent neurotoxin at high doses, at low concentrations of 0.05 to 1.47 mg/kg that occur in domestic cheeses, it was found to be "safe for the consumer". It is also considered as one of the most important fungal contaminants of carbonated beverages, beer, wine, meats, cheese and bread. Both have been synthesised. In addition to these toxic properties, roquefortine C reportedly possesses bacteriostatic activity against gram-positive bacteria, but only in those organisms containing haemoproteins. Roquefortine C contains the unusual E-dehydrohistidine moiety, a system that typically undergoes facile isomerization under acidic, basic, or photochemical conditions to isoroquefortine C, the 3,12 double-bond Z-isomer of roquefortine C.However isoroquefortine C is not a natural product and in contrast to roquefortine C does not bind iron. The mechanisms underlying its toxicity and metabolism have been investigated by studying its interaction with mammalian Cytochrome P450. |
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Structure | CC(C)(C=C)C12CC3N(C1NC1=C2C=CC=C1)C(=O)\C(NC3=O)=C/C1=CNC=N1 InChI=1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9+ |
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Synonyms | Value | Source |
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Roquefortine C | HMDB | Roquefortin | HMDB | Isoroquefortine C | HMDB | Roquefortine | MeSH |
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Chemical Formula | C22H23N5O2 |
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Average Molecular Weight | 389.4503 |
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Monoisotopic Molecular Weight | 389.185175005 |
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IUPAC Name | (4E)-4-(1H-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10(15),11,13-triene-3,6-dione |
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Traditional Name | (4E)-4-(1H-imidazol-4-ylmethylidene)-9-(2-methylbut-3-en-2-yl)-2,5,16-triazatetracyclo[7.7.0.0²,⁷.0¹⁰,¹⁵]hexadeca-10(15),11,13-triene-3,6-dione |
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CAS Registry Number | 58735-64-1 |
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SMILES | CC(C)(C=C)C12CC3N(C1NC1=C2C=CC=C1)C(=O)\C(NC3=O)=C/C1=CNC=N1 |
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InChI Identifier | InChI=1S/C22H23N5O2/c1-4-21(2,3)22-10-17-18(28)25-16(9-13-11-23-12-24-13)19(29)27(17)20(22)26-15-8-6-5-7-14(15)22/h4-9,11-12,17,20,26H,1,10H2,2-3H3,(H,23,24)(H,25,28)/b16-9+ |
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InChI Key | SPWSUFUPTSJWNG-CXUHLZMHSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Indoles and derivatives |
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Sub Class | Pyrroloindoles |
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Direct Parent | Pyrroloindoles |
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Alternative Parents | |
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Substituents | - Pyrroloindole
- Alpha-amino acid or derivatives
- Indole
- Dihydroindole
- Dioxopiperazine
- 2,5-dioxopiperazine
- Secondary aliphatic/aromatic amine
- N-alkylpiperazine
- 1,4-diazinane
- Piperazine
- Benzenoid
- Heteroaromatic compound
- Pyrrolidine
- Pyrrole
- Tertiary carboxylic acid amide
- Azole
- Imidazole
- Secondary carboxylic acid amide
- Amino acid or derivatives
- Lactam
- Carboxamide group
- Secondary amine
- Azacycle
- Carboxylic acid derivative
- Hydrocarbon derivative
- Organic oxygen compound
- Organic nitrogen compound
- Organopnictogen compound
- Organic oxide
- Carbonyl group
- Organonitrogen compound
- Organooxygen compound
- Amine
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic 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 | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 195 - 200 °C | 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 IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Roquefortine,1TMS,isomer #1 | C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12 | 3493.4 | Semi standard non polar | 33892256 | Roquefortine,1TMS,isomer #1 | C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12 | 3312.6 | Standard non polar | 33892256 | Roquefortine,1TMS,isomer #2 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1NC1=CC=CC=C12 | 3430.2 | Semi standard non polar | 33892256 | Roquefortine,1TMS,isomer #2 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1NC1=CC=CC=C12 | 3254.8 | Standard non polar | 33892256 | Roquefortine,1TMS,isomer #3 | C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12 | 3687.4 | Semi standard non polar | 33892256 | Roquefortine,1TMS,isomer #3 | C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12 | 3496.3 | Standard non polar | 33892256 | Roquefortine,2TMS,isomer #1 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12 | 3323.1 | Semi standard non polar | 33892256 | Roquefortine,2TMS,isomer #1 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12 | 3239.2 | Standard non polar | 33892256 | Roquefortine,2TMS,isomer #2 | C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12 | 3551.5 | Semi standard non polar | 33892256 | Roquefortine,2TMS,isomer #2 | C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12 | 3461.7 | Standard non polar | 33892256 | Roquefortine,2TMS,isomer #3 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12 | 3545.7 | Semi standard non polar | 33892256 | Roquefortine,2TMS,isomer #3 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12 | 3387.0 | Standard non polar | 33892256 | Roquefortine,3TMS,isomer #1 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12 | 3442.6 | Semi standard non polar | 33892256 | Roquefortine,3TMS,isomer #1 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C)/C(=C/C4=CN([Si](C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C)C1=CC=CC=C12 | 3334.5 | Standard non polar | 33892256 | Roquefortine,1TBDMS,isomer #1 | C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12 | 3738.6 | Semi standard non polar | 33892256 | Roquefortine,1TBDMS,isomer #1 | C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12 | 3541.3 | Standard non polar | 33892256 | Roquefortine,1TBDMS,isomer #2 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1NC1=CC=CC=C12 | 3635.7 | Semi standard non polar | 33892256 | Roquefortine,1TBDMS,isomer #2 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1NC1=CC=CC=C12 | 3460.2 | Standard non polar | 33892256 | Roquefortine,1TBDMS,isomer #3 | C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12 | 3947.4 | Semi standard non polar | 33892256 | Roquefortine,1TBDMS,isomer #3 | C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12 | 3706.9 | Standard non polar | 33892256 | Roquefortine,2TBDMS,isomer #1 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12 | 3733.8 | Semi standard non polar | 33892256 | Roquefortine,2TBDMS,isomer #1 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=C[NH]C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12 | 3630.6 | Standard non polar | 33892256 | Roquefortine,2TBDMS,isomer #2 | C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12 | 4004.6 | Semi standard non polar | 33892256 | Roquefortine,2TBDMS,isomer #2 | C=CC(C)(C)C12CC3C(=O)N/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12 | 3868.4 | Standard non polar | 33892256 | Roquefortine,2TBDMS,isomer #3 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12 | 3968.3 | Semi standard non polar | 33892256 | Roquefortine,2TBDMS,isomer #3 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1NC1=CC=CC=C12 | 3775.9 | Standard non polar | 33892256 | Roquefortine,3TBDMS,isomer #1 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12 | 4042.1 | Semi standard non polar | 33892256 | Roquefortine,3TBDMS,isomer #1 | C=CC(C)(C)C12CC3C(=O)N([Si](C)(C)C(C)(C)C)/C(=C/C4=CN([Si](C)(C)C(C)(C)C)C=N4)C(=O)N3C1N([Si](C)(C)C(C)(C)C)C1=CC=CC=C12 | 3905.3 | Standard non polar | 33892256 |
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