| Record Information |
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| Version | 2.0 |
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| Created at | 2022-09-07 14:17:43 UTC |
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| Updated at | 2022-09-07 14:17:43 UTC |
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| NP-MRD ID | NP0251176 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | 2,12-dimethyl (2s,5r,7s,8r,12s,15r,17s,18r,19s,24s)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2⁸,¹¹.0⁴,⁹.0⁵,⁷.0¹⁵,¹⁷.0¹⁸,²²]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate |
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| Description | Cycloshizukaol A belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 2,12-dimethyl (2s,5r,7s,8r,12s,15r,17s,18r,19s,24s)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2⁸,¹¹.0⁴,⁹.0⁵,⁷.0¹⁵,¹⁷.0¹⁸,²²]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate is found in Chloranthus serratus. 2,12-dimethyl (2s,5r,7s,8r,12s,15r,17s,18r,19s,24s)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2⁸,¹¹.0⁴,⁹.0⁵,⁷.0¹⁵,¹⁷.0¹⁸,²²]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate was first documented in 2006 (PMID: 16229979). Based on a literature review a small amount of articles have been published on Cycloshizukaol A (PMID: 21963639) (PMID: 29243431) (PMID: 18855217) (PMID: 35579502). |
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| Structure | COC(=O)[C@@]1(C)CC2=C3C=C(C(=O)[C@@H](O)[C@]3(C)[C@H]3C[C@@H]23)[C@](C)(CC2=C3C=C1C(=O)[C@@H](O)[C@]3(C)[C@H]1C[C@@H]21)C(=O)OC InChI=1S/C32H36O8/c1-29(27(37)39-5)11-15-13-7-17(13)32(4)20(15)10-22(24(34)26(32)36)30(2,28(38)40-6)12-16-14-8-18(14)31(3)19(16)9-21(29)23(33)25(31)35/h9-10,13-14,17-18,25-26,35-36H,7-8,11-12H2,1-6H3/t13-,14-,17-,18-,25+,26+,29-,30-,31+,32+/m0/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C32H36O8 |
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| Average Mass | 548.6320 Da |
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| Monoisotopic Mass | 548.24102 Da |
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| IUPAC Name | 2,12-dimethyl (2S,5R,7S,8R,12S,15R,17S,18R,19S,24S)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2^{8,11}.0^{4,9}.0^{5,7}.0^{15,17}.0^{18,22}]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate |
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| Traditional Name | 2,12-dimethyl (2S,5R,7S,8R,12S,15R,17S,18R,19S,24S)-19,24-dihydroxy-2,8,12,18-tetramethyl-20,23-dioxoheptacyclo[12.6.2.2^{8,11}.0^{4,9}.0^{5,7}.0^{15,17}.0^{18,22}]tetracosa-1(21),4(9),10,14(22)-tetraene-2,12-dicarboxylate |
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| CAS Registry Number | Not Available |
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| SMILES | COC(=O)[C@@]1(C)CC2=C3C=C(C(=O)[C@@H](O)[C@]3(C)[C@H]3C[C@@H]23)[C@](C)(CC2=C3C=C1C(=O)[C@@H](O)[C@]3(C)[C@H]1C[C@@H]21)C(=O)OC |
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| InChI Identifier | InChI=1S/C32H36O8/c1-29(27(37)39-5)11-15-13-7-17(13)32(4)20(15)10-22(24(34)26(32)36)30(2,28(38)40-6)12-16-14-8-18(14)31(3)19(16)9-21(29)23(33)25(31)35/h9-10,13-14,17-18,25-26,35-36H,7-8,11-12H2,1-6H3/t13-,14-,17-,18-,25+,26+,29-,30-,31+,32+/m0/s1 |
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| InChI Key | YSPXFYFVBVEVBW-IREBYWDYSA-N |
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| Experimental Spectra |
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| Not Available | | 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 cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. |
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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 | Cyclohexenones |
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| Alternative Parents | |
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| Substituents | - Cyclohexenone
- Dicarboxylic acid or derivatives
- Methyl ester
- Secondary alcohol
- Carboxylic acid ester
- Carboxylic acid derivative
- Organic oxide
- Hydrocarbon derivative
- Alcohol
- Aliphatic homopolycyclic compound
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| Molecular Framework | Aliphatic homopolycyclic 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 | - Kim SY, Kashiwada Y, Kawazoe K, Murakami K, Sun HD, Li SL, Takaishi Y: Spicachlorantins G-J, new lindenane sesquiterpenoid dimers from the roots of Chloranthus spicatus. Chem Pharm Bull (Tokyo). 2011;59(10):1281-4. doi: 10.1248/cpb.59.1281. [PubMed:21963639 ]
- Zhang SS, Fu JJ, Chen HY, Tu LF, Xiao CR, Zhang RZ, Liu DP, Luo YM: [Sesquiterpenes with anti-metastasis breast cancer activity from Chloranthus henryi]. Zhongguo Zhong Yao Za Zhi. 2017 Oct;42(20):3938-3944. doi: 10.19540/j.cnki.cjcmm.2017.0159. [PubMed:29243431 ]
- Yang SP, Yue JM: Terpenoids from Chloranthus multistachys. Nat Prod Res. 2008;22(13):1163-8. doi: 10.1080/14786410601133434. [PubMed:18855217 ]
- Huang Z, Huang G, Wang X, Qin S, Fu S, Liu B: Asymmetric Total Synthesis of Natural Lindenane Sesquiterpenoid Oligomers via a Triene as a Potential Biosynthetic Intermediate. Angew Chem Int Ed Engl. 2022 Jul 18;61(29):e202204303. doi: 10.1002/anie.202204303. Epub 2022 Jun 1. [PubMed:35579502 ]
- Kwon OE, Lee HS, Lee SW, Bae K, Kim K, Hayashi M, Rho MC, Kim YK: Dimeric sesquiterpenoids isolated from Chloranthus japonicus inhibited the expression of cell adhesion molecules. J Ethnopharmacol. 2006 Mar 8;104(1-2):270-7. doi: 10.1016/j.jep.2005.09.018. Epub 2005 Oct 17. [PubMed:16229979 ]
- LOTUS database [Link]
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