Record Information |
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Version | 1.0 |
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Created at | 2022-09-12 02:01:55 UTC |
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Updated at | 2022-09-12 02:01:55 UTC |
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NP-MRD ID | NP0322937 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | (2r,4ar,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-4a-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2-carboxylic acid |
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Description | 3Beta,28-Dihydroxyoleana-12-ene-29-oic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (2r,4ar,6as,6br,8ar,10s,12ar,12br,14bs)-10-hydroxy-4a-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2-carboxylic acid is found in Tripterygium wilfordii. It was first documented in 2020 (PMID: 36119797). Based on a literature review a significant number of articles have been published on 3beta,28-Dihydroxyoleana-12-ene-29-oic acid (PMID: 36115656) (PMID: 36118359) (PMID: 36110404) (PMID: 36089004). |
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Structure | CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3C[C@@](C)(CC[C@]3(CO)CC[C@@]12C)C(O)=O InChI=1S/C30H48O4/c1-25(2)21-9-12-29(6)22(27(21,4)11-10-23(25)32)8-7-19-20-17-26(3,24(33)34)13-15-30(20,18-31)16-14-28(19,29)5/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21-,22+,23-,26+,27-,28+,29+,30+/m0/s1 |
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Synonyms | Value | Source |
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3b,28-Dihydroxyoleana-12-ene-29-Oate | Generator | 3b,28-Dihydroxyoleana-12-ene-29-Oic acid | Generator | 3beta,28-Dihydroxyoleana-12-ene-29-Oate | Generator | 3Β,28-dihydroxyoleana-12-ene-29-Oate | Generator | 3Β,28-dihydroxyoleana-12-ene-29-Oic acid | Generator |
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Chemical Formula | C30H48O4 |
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Average Mass | 472.7100 Da |
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Monoisotopic Mass | 472.35526 Da |
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IUPAC Name | (2R,4aR,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-4a-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-2-carboxylic acid |
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Traditional Name | (2R,4aR,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-4a-(hydroxymethyl)-2,6a,6b,9,9,12a-hexamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-2-carboxylic acid |
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CAS Registry Number | Not Available |
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SMILES | CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2CC=C2[C@@H]3C[C@@](C)(CC[C@]3(CO)CC[C@@]12C)C(O)=O |
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InChI Identifier | InChI=1S/C30H48O4/c1-25(2)21-9-12-29(6)22(27(21,4)11-10-23(25)32)8-7-19-20-17-26(3,24(33)34)13-15-30(20,18-31)16-14-28(19,29)5/h7,20-23,31-32H,8-18H2,1-6H3,(H,33,34)/t20-,21-,22+,23-,26+,27-,28+,29+,30+/m0/s1 |
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InChI Key | DDJYMOPTHNUMHK-GNSVDKAYSA-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 triterpenoids. These are terpene molecules containing six isoprene units. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Triterpenoids |
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Direct Parent | Triterpenoids |
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Alternative Parents | |
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Substituents | - Triterpenoid
- Cyclic alcohol
- Secondary alcohol
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- 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 | - Lo YL, Lin HC, Tseng WH: Tumor pH-functionalized and charge-tunable nanoparticles for the nucleus/cytoplasm-directed delivery of oxaliplatin and miRNA in the treatment of head and neck cancer. Acta Biomater. 2022 Sep 14. pii: S1742-7061(22)00586-4. doi: 10.1016/j.actbio.2022.09.027. [PubMed:36115656 ]
- Han SW, Shi SM, Zou YX, Wang ZC, Wang YQ, Shi L, Yan TC: Chemical constituents from acid hydrolyzates of Panax quinquefolius total saponins and their inhibition activity to alpha-glycosidase and protein tyrosine phosphatase 1B. Chin Herb Med. 2020 Mar 14;12(2):195-199. doi: 10.1016/j.chmed.2020.03.003. eCollection 2020 Apr. [PubMed:36119797 ]
- Wang G, Li M, Wang Y, Wang B, Pu H, Mao J, Zhang S, Zhou S, Luo P: Characterization of differentially expressed and lipid metabolism-related lncRNA-mRNA interaction networks during the growth of liver tissue through rabbit models. Front Vet Sci. 2022 Sep 1;9:998796. doi: 10.3389/fvets.2022.998796. eCollection 2022. [PubMed:36118359 ]
- de Vasconcelos DAA, Nachbar RT, Pinheiro CH, do Amaral CL, Crisma AR, Vitzel KF, Abreu P, Alonso-Vale MI, Lopes AB, Bento-Santos A, Falcao-Tebas F, de Santana DF, do Nascimento E, Curi R, Pithon-Curi TC, Hirabara SM, Leandro CG: Maternal low-protein diet reduces skeletal muscle protein synthesis and mass via Akt-mTOR pathway in adult rats. Front Nutr. 2022 Aug 30;9:947458. doi: 10.3389/fnut.2022.947458. eCollection 2022. [PubMed:36110404 ]
- Takei H, Narushima S, Suzuki M, Kakiyama G, Sasaki T, Murai T, Yamashiro Y, Nittono H: Characterization of long-chain fatty acid-linked bile acids: a major conjugation form of 3beta-hydroxy bile acids in feces. J Lipid Res. 2022 Oct;63(10):100275. doi: 10.1016/j.jlr.2022.100275. Epub 2022 Sep 9. [PubMed:36089004 ]
- LOTUS database [Link]
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