Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2007-01-22 22:27:09 UTC |
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Update Date | 2022-03-07 02:49:29 UTC |
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HMDB ID | HMDB0005798 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Malabaricone C |
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Description | Malabaricone C is an antimicrobial resorcinol found in nutmeg, the dried seed covers of Myristica fragrans and Myristica malabarica (rampatri). This Compound exhibits strong antifungal and antibacterial activity. (PMID 1955885 , 10501006 ). Malabaricone C a diarylnonanoid, shows strong scavenging activity. (PMID 16104820 ). |
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Structure | OC1=CC=CC(O)=C1C(=O)CCCCCCCCC1=CC(O)=C(O)C=C1 InChI=1S/C21H26O5/c22-16-13-12-15(14-20(16)26)8-5-3-1-2-4-6-9-17(23)21-18(24)10-7-11-19(21)25/h7,10-14,22,24-26H,1-6,8-9H2 |
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Synonyms | Value | Source |
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Malabaricone C | MeSH |
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Chemical Formula | C21H26O5 |
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Average Molecular Weight | 358.4281 |
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Monoisotopic Molecular Weight | 358.178023942 |
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IUPAC Name | 1-(2,6-dihydroxyphenyl)-9-(3,4-dihydroxyphenyl)nonan-1-one |
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Traditional Name | malabaricone C |
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CAS Registry Number | 63335-25-1 |
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SMILES | OC1=CC=CC(O)=C1C(=O)CCCCCCCCC1=CC(O)=C(O)C=C1 |
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InChI Identifier | InChI=1S/C21H26O5/c22-16-13-12-15(14-20(16)26)8-5-3-1-2-4-6-9-17(23)21-18(24)10-7-11-19(21)25/h7,10-14,22,24-26H,1-6,8-9H2 |
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InChI Key | HCOZRFYGIFMIEX-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbonyl compounds |
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Direct Parent | Alkyl-phenylketones |
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Alternative Parents | |
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Substituents | - Alkyl-phenylketone
- Butyrophenone
- Aryl alkyl ketone
- Resorcinol
- Catechol
- Benzoyl
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous acid
- Organic oxide
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | 119 - 121 °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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Malabaricone C,1TMS,isomer #1 | C[Si](C)(C)OC1=CC=CC(O)=C1C(=O)CCCCCCCCC1=CC=C(O)C(O)=C1 | 3216.2 | Semi standard non polar | 33892256 | Malabaricone C,1TMS,isomer #2 | C[Si](C)(C)OC1=CC(CCCCCCCCC(=O)C2=C(O)C=CC=C2O)=CC=C1O | 3181.9 | Semi standard non polar | 33892256 | Malabaricone C,1TMS,isomer #3 | C[Si](C)(C)OC1=CC=C(CCCCCCCCC(=O)C2=C(O)C=CC=C2O)C=C1O | 3182.7 | Semi standard non polar | 33892256 | Malabaricone C,2TMS,isomer #1 | C[Si](C)(C)OC1=CC=CC(O[Si](C)(C)C)=C1C(=O)CCCCCCCCC1=CC=C(O)C(O)=C1 | 3189.2 | Semi standard non polar | 33892256 | Malabaricone C,2TMS,isomer #2 | C[Si](C)(C)OC1=CC=C(CCCCCCCCC(=O)C2=C(O)C=CC=C2O[Si](C)(C)C)C=C1O | 3139.4 | Semi standard non polar | 33892256 | Malabaricone C,2TMS,isomer #3 | C[Si](C)(C)OC1=CC(CCCCCCCCC(=O)C2=C(O)C=CC=C2O[Si](C)(C)C)=CC=C1O | 3141.8 | Semi standard non polar | 33892256 | Malabaricone C,2TMS,isomer #4 | C[Si](C)(C)OC1=CC=C(CCCCCCCCC(=O)C2=C(O)C=CC=C2O)C=C1O[Si](C)(C)C | 3138.0 | Semi standard non polar | 33892256 | Malabaricone C,3TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(CCCCCCCCC(=O)C2=C(O[Si](C)(C)C)C=CC=C2O[Si](C)(C)C)C=C1O | 3192.3 | Semi standard non polar | 33892256 | Malabaricone C,3TMS,isomer #2 | C[Si](C)(C)OC1=CC(CCCCCCCCC(=O)C2=C(O[Si](C)(C)C)C=CC=C2O[Si](C)(C)C)=CC=C1O | 3176.4 | Semi standard non polar | 33892256 | Malabaricone C,3TMS,isomer #3 | C[Si](C)(C)OC1=CC=C(CCCCCCCCC(=O)C2=C(O)C=CC=C2O[Si](C)(C)C)C=C1O[Si](C)(C)C | 3160.0 | Semi standard non polar | 33892256 | Malabaricone C,4TMS,isomer #1 | C[Si](C)(C)OC1=CC=C(CCCCCCCCC(=O)C2=C(O[Si](C)(C)C)C=CC=C2O[Si](C)(C)C)C=C1O[Si](C)(C)C | 3244.5 | Semi standard non polar | 33892256 | Malabaricone C,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=CC(O)=C1C(=O)CCCCCCCCC1=CC=C(O)C(O)=C1 | 3493.4 | Semi standard non polar | 33892256 | Malabaricone C,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC(CCCCCCCCC(=O)C2=C(O)C=CC=C2O)=CC=C1O | 3441.8 | Semi standard non polar | 33892256 | Malabaricone C,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCCCCCC(=O)C2=C(O)C=CC=C2O)C=C1O | 3447.9 | Semi standard non polar | 33892256 | Malabaricone C,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1C(=O)CCCCCCCCC1=CC=C(O)C(O)=C1 | 3717.5 | Semi standard non polar | 33892256 | Malabaricone C,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCCCCCC(=O)C2=C(O)C=CC=C2O[Si](C)(C)C(C)(C)C)C=C1O | 3636.9 | Semi standard non polar | 33892256 | Malabaricone C,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC(CCCCCCCCC(=O)C2=C(O)C=CC=C2O[Si](C)(C)C(C)(C)C)=CC=C1O | 3648.0 | Semi standard non polar | 33892256 | Malabaricone C,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCCCCCC(=O)C2=C(O)C=CC=C2O)C=C1O[Si](C)(C)C(C)(C)C | 3614.5 | Semi standard non polar | 33892256 | Malabaricone C,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCCCCCC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC=C2O[Si](C)(C)C(C)(C)C)C=C1O | 3860.0 | Semi standard non polar | 33892256 | Malabaricone C,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1=CC(CCCCCCCCC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC=C2O[Si](C)(C)C(C)(C)C)=CC=C1O | 3839.2 | Semi standard non polar | 33892256 | Malabaricone C,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCCCCCC(=O)C2=C(O)C=CC=C2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C | 3802.7 | Semi standard non polar | 33892256 | Malabaricone C,4TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OC1=CC=C(CCCCCCCCC(=O)C2=C(O[Si](C)(C)C(C)(C)C)C=CC=C2O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C | 4053.5 | Semi standard non 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 - Malabaricone C GC-MS (Non-derivatized) - 70eV, Positive | splash10-000i-1920000000-b8592506af2248437650 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Malabaricone C GC-MS (4 TMS) - 70eV, Positive | splash10-001i-0092012000-0c22b43dd02d160f671a | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Malabaricone C 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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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Malabaricone C 10V, Positive-QTOF | splash10-0a4i-0219000000-e51af4d04290eb642011 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Malabaricone C 20V, Positive-QTOF | splash10-000i-0922000000-42c53ffcaea645650850 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Malabaricone C 40V, Positive-QTOF | splash10-000i-2900000000-4abf227b55b271a2038d | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Malabaricone C 10V, Negative-QTOF | splash10-0a4i-0209000000-0f6a0ead2336735f06fc | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Malabaricone C 20V, Negative-QTOF | splash10-0a4i-0915000000-012d981777388454277b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Malabaricone C 40V, Negative-QTOF | splash10-0a4i-4921000000-5f3698a77ed91a620153 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Malabaricone C 10V, Negative-QTOF | splash10-0a4i-0009000000-7002cb51d7f42580da74 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Malabaricone C 20V, Negative-QTOF | splash10-0a4r-1914000000-2b2d930703f4846b4e18 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Malabaricone C 40V, Negative-QTOF | splash10-066r-8920000000-098e4e80b4bf38bf80af | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Malabaricone C 10V, Positive-QTOF | splash10-0a4r-0639000000-d71a1b0cdf06248f5975 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Malabaricone C 20V, Positive-QTOF | splash10-000i-1911000000-366ad04c286826c770ab | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Malabaricone C 40V, Positive-QTOF | splash10-000i-1900000000-85e717dc79759f411d54 | 2021-09-23 | Wishart Lab | View Spectrum |
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General References | - Orabi KY, Mossa JS, el-Feraly FS: Isolation and characterization of two antimicrobial agents from mace (Myristica fragrans). J Nat Prod. 1991 May-Jun;54(3):856-9. [PubMed:1955885 ]
- Shinohara C, Mori S, Ando T, Tsuji T: Arg-gingipain inhibition and anti-bacterial activity selective for Porphyromonas gingivalis by malabaricone C. Biosci Biotechnol Biochem. 1999 Aug;63(8):1475-7. [PubMed:10501006 ]
- Patro BS, Bauri AK, Mishra S, Chattopadhyay S: Antioxidant activity of Myristica malabarica extracts and their constituents. J Agric Food Chem. 2005 Aug 24;53(17):6912-8. [PubMed:16104820 ]
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