Record Information |
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Version | 1.0 |
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Created at | 2021-11-12 23:44:29 UTC |
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Updated at | 2021-11-26 17:44:43 UTC |
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NP-MRD ID | NP0044038 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,4,6-heptatrien-3-one |
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Description | 1,7-Bis(4-hydroxy-3-methoxyphenyl)-1,4,6-heptatrien-3-one, also known as asc-J9 compound, belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,4,6-heptatrien-3-one is found in Curcuma longa. It was first documented in 2002 (PMID: 12350137). Based on a literature review a small amount of articles have been published on 1,7-bis(4-hydroxy-3-methoxyphenyl)-1,4,6-heptatrien-3-one (PMID: 25273391) (PMID: 17004725) (PMID: 12408714). |
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Structure | COC1=C(O)C=CC(\C=C\C=C\C(=O)\C=C\C2=CC(OC)=C(O)C=C2)=C1 InChI=1S/C21H20O5/c1-25-20-13-15(8-11-18(20)23)5-3-4-6-17(22)10-7-16-9-12-19(24)21(14-16)26-2/h3-14,23-24H,1-2H3/b5-3+,6-4+,10-7+ |
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Synonyms | Value | Source |
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ASC-J9 compound | MeSH |
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Chemical Formula | C21H20O5 |
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Average Mass | 352.3860 Da |
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Monoisotopic Mass | 352.13107 Da |
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IUPAC Name | (1E,4E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one |
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Traditional Name | (1E,4E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,4,6-trien-3-one |
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CAS Registry Number | Not Available |
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SMILES | COC1=C(O)C=CC(\C=C\C=C\C(=O)\C=C\C2=CC(OC)=C(O)C=C2)=C1 |
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InChI Identifier | InChI=1S/C21H20O5/c1-25-20-13-15(8-11-18(20)23)5-3-4-6-17(22)10-7-16-9-12-19(24)21(14-16)26-2/h3-14,23-24H,1-2H3/b5-3+,6-4+,10-7+ |
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InChI Key | JUDCTVXWYFNGQQ-FQXJPFFWSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 50 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Acetone-d6, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Diarylheptanoids |
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Sub Class | Linear diarylheptanoids |
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Direct Parent | Linear diarylheptanoids |
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Alternative Parents | |
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Substituents | - Linear 1,7-diphenylheptane skeleton
- Cinnamic acid or derivatives
- Hydroxycinnamic acid or derivatives
- Methoxyphenol
- Methoxybenzene
- Styrene
- Phenol ether
- Anisole
- Phenoxy compound
- Alkyl aryl ether
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Monocyclic benzene moiety
- Alpha,beta-unsaturated ketone
- Acryloyl-group
- Enone
- Ketone
- Ether
- Organic oxide
- Carbonyl group
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | Not Available |
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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 | - Park SY, Kim DS: Discovery of natural products from Curcuma longa that protect cells from beta-amyloid insult: a drug discovery effort against Alzheimer's disease. J Nat Prod. 2002 Sep;65(9):1227-31. doi: 10.1021/np010039x. [PubMed:12350137 ]
- Yang MH, Chin YW, Chae HS, Yoon KD, Kim J: Anti-adipogenic constituents from Dioscorea opposita in 3T3-L1 cells. Biol Pharm Bull. 2014;37(10):1683-8. doi: 10.1248/bpb.b14-00216. [PubMed:25273391 ]
- Ryu EK, Choe YS, Lee KH, Choi Y, Kim BT: Curcumin and dehydrozingerone derivatives: synthesis, radiolabeling, and evaluation for beta-amyloid plaque imaging. J Med Chem. 2006 Oct 5;49(20):6111-9. doi: 10.1021/jm0607193. [PubMed:17004725 ]
- Ohtsu H, Xiao Z, Ishida J, Nagai M, Wang HK, Itokawa H, Su CY, Shih C, Chiang T, Chang E, Lee Y, Tsai MY, Chang C, Lee KH: Antitumor agents. 217. Curcumin analogues as novel androgen receptor antagonists with potential as anti-prostate cancer agents. J Med Chem. 2002 Nov 7;45(23):5037-42. doi: 10.1021/jm020200g. [PubMed:12408714 ]
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