| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-08 03:35:42 UTC |
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| Updated at | 2022-09-08 03:35:43 UTC |
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| NP-MRD ID | NP0261212 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | (1r,10s)-5-[(1s,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,4,6,14-tetrahydroxy-10-(3-methylbut-2-en-1-yl)-9,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-3,5,7,11,13,15-hexaen-2-one |
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| Description | Sanggenon O 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. (1r,10s)-5-[(1s,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,4,6,14-tetrahydroxy-10-(3-methylbut-2-en-1-yl)-9,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-3,5,7,11,13,15-hexaen-2-one is found in Morus alba, Morus cathayana and Morus mongolica. (1r,10s)-5-[(1s,5s,6r)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,4,6,14-tetrahydroxy-10-(3-methylbut-2-en-1-yl)-9,17-dioxatetracyclo[8.7.0.0³,⁸.0¹¹,¹⁶]heptadeca-3,5,7,11,13,15-hexaen-2-one was first documented in 2012 (PMID: 21612567). Based on a literature review a small amount of articles have been published on sanggenon O (PMID: 29191050) (PMID: 31920173) (PMID: 30953888) (PMID: 25187688). |
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| Structure | CC(C)=CC[C@@]12OC3=CC(O)=C([C@H]4C=C(C)C[C@@H]([C@H]4C(=O)C4=CC=C(O)C=C4O)C4=CC=C(O)C=C4O)C(O)=C3C(=O)[C@]1(O)OC1=CC(O)=CC=C21 InChI=1S/C40H36O12/c1-18(2)10-11-39-27-9-6-22(43)16-31(27)52-40(39,50)38(49)35-32(51-39)17-30(46)34(37(35)48)26-13-19(3)12-25(23-7-4-20(41)14-28(23)44)33(26)36(47)24-8-5-21(42)15-29(24)45/h4-10,13-17,25-26,33,41-46,48,50H,11-12H2,1-3H3/t25-,26+,33-,39+,40+/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C40H36O12 |
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| Average Mass | 708.7160 Da |
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| Monoisotopic Mass | 708.22068 Da |
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| IUPAC Name | (1R,10S)-5-[(1S,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,4,6,14-tetrahydroxy-10-(3-methylbut-2-en-1-yl)-9,17-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-3,5,7,11,13,15-hexaen-2-one |
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| Traditional Name | (1R,10S)-5-[(1S,5S,6R)-6-(2,4-dihydroxybenzoyl)-5-(2,4-dihydroxyphenyl)-3-methylcyclohex-2-en-1-yl]-1,4,6,14-tetrahydroxy-10-(3-methylbut-2-en-1-yl)-9,17-dioxatetracyclo[8.7.0.0^{3,8}.0^{11,16}]heptadeca-3,5,7,11,13,15-hexaen-2-one |
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| CAS Registry Number | Not Available |
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| SMILES | CC(C)=CC[C@@]12OC3=CC(O)=C([C@H]4C=C(C)C[C@@H]([C@H]4C(=O)C4=CC=C(O)C=C4O)C4=CC=C(O)C=C4O)C(O)=C3C(=O)[C@]1(O)OC1=CC(O)=CC=C21 |
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| InChI Identifier | InChI=1S/C40H36O12/c1-18(2)10-11-39-27-9-6-22(43)16-31(27)52-40(39,50)38(49)35-32(51-39)17-30(46)34(37(35)48)26-13-19(3)12-25(23-7-4-20(41)14-28(23)44)33(26)36(47)24-8-5-21(42)15-29(24)45/h4-10,13-17,25-26,33,41-46,48,50H,11-12H2,1-3H3/t25-,26+,33-,39+,40+/m1/s1 |
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| InChI Key | XETHJOZXBVWLLM-HCAFVXMDSA-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, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, H2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, H2O, 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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| 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
- Alkyl-phenylketone
- Chromone
- 1-benzopyran
- Benzopyran
- Chromane
- Phenylketone
- Coumaran
- Resorcinol
- Aryl ketone
- Aryl alkyl ketone
- Benzoyl
- 1-hydroxy-4-unsubstituted benzenoid
- Alkyl aryl ether
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Vinylogous acid
- Ketone
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Ether
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic 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 | - Hu X, Yu MH, Yan GR, Wang HY, Hou AJ, Lei C: Isoprenylated phenolic compounds with tyrosinase inhibition from Morus nigra. J Asian Nat Prod Res. 2018 May;20(5):488-493. doi: 10.1080/10286020.2017.1350653. Epub 2017 Nov 30. [PubMed:29191050 ]
- Yadav R, Selvaraj C, Aarthy M, Kumar P, Kumar A, Singh SK, Giri R: Investigating into the molecular interactions of flavonoids targeting NS2B-NS3 protease from ZIKA virus through in-silico approaches. J Biomol Struct Dyn. 2021 Jan;39(1):272-284. doi: 10.1080/07391102.2019.1709546. Epub 2020 Jan 10. [PubMed:31920173 ]
- Li ZR, Ma T, Guo YJ, Hu B, Niu SH, Suo FZ, Du LN, You YH, Kang WT, Liu S, Mamun M, Song QM, Pang JR, Zheng YC, Liu HM: Sanggenon O induced apoptosis of A549 cells is counterbalanced by protective autophagy. Bioorg Chem. 2019 Jun;87:688-698. doi: 10.1016/j.bioorg.2019.03.072. Epub 2019 Apr 4. [PubMed:30953888 ]
- Qamar MT, Mumtaz A, Naseem R, Ali A, Fatima T, Jabbar T, Ahmad Z, Ashfaq UA: Molecular Docking Based Screening of Plant Flavonoids as Dengue NS1 Inhibitors. Bioinformation. 2014 Jul 22;10(7):460-5. doi: 10.6026/97320630010460. eCollection 2014. [PubMed:25187688 ]
- Dat NT, Binh PT, Quynh le TP, Huong HT, Minh CV: Sanggenon C and O inhibit NO production, iNOS expression and NF-kappaB activation in LPS-induced RAW264.7 cells. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):84-8. doi: 10.3109/08923973.2011.580755. Epub 2011 May 26. [PubMed:21612567 ]
- LOTUS database [Link]
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