| Record Information |
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| Version | 2.0 |
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| Created at | 2022-06-29 21:56:44 UTC |
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| Updated at | 2022-06-29 21:56:45 UTC |
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| NP-MRD ID | NP0140884 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Hautriwaic acid |
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| Description | Hautriwaic acid, also known as hautriwaate, belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. Hautriwaic acid is found in Baccharis calvescens, Baccharis chilco, Baccharis sarothroides, Croton setiger, Dodonaea viscosa and Nidorella ivifolia. Hautriwaic acid was first documented in 2012 (PMID: 22491678). Based on a literature review a small amount of articles have been published on Hautriwaic acid (PMID: 32927597) (PMID: 30525440) (PMID: 26166136) (PMID: 24075215). |
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| Structure | C[C@@H]1CC[C@]2(CO)[C@H](CCC=C2C(O)=O)[C@@]1(C)CCC1=COC=C1 InChI=1S/C20H28O4/c1-14-6-10-20(13-21)16(18(22)23)4-3-5-17(20)19(14,2)9-7-15-8-11-24-12-15/h4,8,11-12,14,17,21H,3,5-7,9-10,13H2,1-2H3,(H,22,23)/t14-,17-,19+,20-/m1/s1 |
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| Synonyms | | Value | Source |
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| Hautriwaate | Generator |
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| Chemical Formula | C20H28O4 |
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| Average Mass | 332.4400 Da |
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| Monoisotopic Mass | 332.19876 Da |
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| IUPAC Name | Not Available |
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| Traditional Name | Not Available |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@@H]1CC[C@]2(CO)[C@H](CCC=C2C(O)=O)[C@@]1(C)CCC1=COC=C1 |
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| InChI Identifier | InChI=1S/C20H28O4/c1-14-6-10-20(13-21)16(18(22)23)4-3-5-17(20)19(14,2)9-7-15-8-11-24-12-15/h4,8,11-12,14,17,21H,3,5-7,9-10,13H2,1-2H3,(H,22,23)/t14-,17-,19+,20-/m1/s1 |
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| InChI Key | PHKSUFCCGLWIMC-SIKIZQCASA-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 colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. |
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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 | Diterpenoids |
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| Direct Parent | Colensane and clerodane diterpenoids |
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| Alternative Parents | |
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| Substituents | - Clerodane diterpenoid
- Furan
- Heteroaromatic compound
- Carboxylic acid derivative
- Carboxylic acid
- Monocarboxylic acid or derivatives
- Organoheterocyclic compound
- Oxacycle
- Organooxygen compound
- Carbonyl group
- Organic oxygen compound
- Primary alcohol
- Organic oxide
- Alcohol
- Hydrocarbon derivative
- 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 | - Kaigongi MM, Lukhoba CW, Ochieng' PJ, Taylor M, Yenesew A, Makunga NP: LC-MS-Based Metabolomics for the Chemosystematics of Kenyan Dodonaea viscosa Jacq (Sapindaceae) Populations. Molecules. 2020 Sep 10;25(18):4130. doi: 10.3390/molecules25184130. [PubMed:32927597 ]
- Cai S, Bellampalli SS, Yu J, Li W, Ji Y, Wijeratne EMK, Dorame A, Luo S, Shan Z, Khanna M, Moutal A, Streicher JM, Gunatilaka AAL, Khanna R: (-)-Hardwickiic Acid and Hautriwaic Acid Induce Antinociception via Blockade of Tetrodotoxin-Sensitive Voltage-Dependent Sodium Channels. ACS Chem Neurosci. 2019 Mar 20;10(3):1716-1728. doi: 10.1021/acschemneuro.8b00617. Epub 2018 Dec 20. [PubMed:30525440 ]
- Salinas-Sanchez DO, Zamilpa A, Perez S, Herrera-Ruiz M, Tortoriello J, Gonzalez-Cortazar M, Jimenez-Ferrer E: Effect of Hautriwaic Acid Isolated from Dodonaea viscosa in a Model of Kaolin/Carrageenan-Induced Monoarthritis. Planta Med. 2015 Sep;81(14):1240-7. doi: 10.1055/s-0035-1546197. Epub 2015 Jul 10. [PubMed:26166136 ]
- Ali H, Kabir N, Muhammad A, Shah MR, Musharraf SG, Iqbal N, Nadeem S: Hautriwaic acid as one of the hepatoprotective constituent of Dodonaea viscosa. Phytomedicine. 2014 Jan 15;21(2):131-40. doi: 10.1016/j.phymed.2013.08.019. Epub 2013 Sep 24. [PubMed:24075215 ]
- Salinas-Sanchez DO, Herrera-Ruiz M, Perez S, Jimenez-Ferrer E, Zamilpa A: Anti-inflammatory activity of hautriwaic acid isolated from Dodonaea viscosa leaves. Molecules. 2012 Apr 10;17(4):4292-9. doi: 10.3390/molecules17044292. [PubMed:22491678 ]
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