Record Information |
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Version | 1.0 |
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Created at | 2021-06-19 23:23:30 UTC |
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Updated at | 2021-08-20 00:00:26 UTC |
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NP-MRD ID | NP0032641 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | dehydroabietic acid |
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Provided By | JEOL Database |
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Description | Dehydroabietic acid, also known as dehydroabietate, belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Dehydroabietic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. dehydroabietic acid is found in Abies pinsapo, Abies spectabilis, Cedrus deodara, Cedrus libani, Anisochilus harmandii, Homo sapiens, Isodon interruptus, Isodon nervosus, Juniperus chinensis, Juniperus sabina, Larix decidua, Larix kaempferi, Phlebiopsis gigantea, Picea ajanensis, Sitka spruce, Pinus densiflora, Pinus massoniana, Pinus palustris, Pinus pumila, Pinus resinosa, Pinus strobus, Pinus sylvestris, Pinus yunnanensis, Pistacia lentiscus, Porodaedalea pini, Relhania corymbosa, Salvia tomentosa and Trametes Versicolor. It was first documented in 2002 (PMID: 12000325). Based on a literature review a significant number of articles have been published on Dehydroabietic acid (PMID: 17439666) (PMID: 19753653) (PMID: 21725812) (PMID: 21742316). |
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Structure | [H]OC(=O)[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2(C3=C(C([H])=C(C([H])=C3[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@]12[H])C([H])([H])[H] InChI=1S/C20H28O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s1 |
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Synonyms | Value | Source |
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(-)-Dehydroabietic acid | ChEBI | 1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylic acid | ChEBI | 13-Isopropylpodocarpa-8,11,13-trien-15-Oic acid | ChEBI | Abieta-8,11,13-trien-18-Oic acid | ChEBI | Dehydroabietate | ChEBI | (-)-Dehydroabietate | Generator | 1,2,3,4,4a,9,10,10a-Octahydro-1,4a-dimethyl-7-(1-methylethyl)-1-phenanthrenecarboxylate | Generator | 13-Isopropylpodocarpa-8,11,13-trien-15-Oate | Generator | Abieta-8,11,13-trien-18-Oate | Generator | (+)-Dehydroabietic acid | HMDB |
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Chemical Formula | C20H28O2 |
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Average Mass | 300.4420 Da |
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Monoisotopic Mass | 300.20893 Da |
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IUPAC Name | (1R,4aS,10aR)-1,4a-dimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylic acid |
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Traditional Name | (-)-dehydroabietic acid |
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CAS Registry Number | Not Available |
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SMILES | [H]OC(=O)[C@]1(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@@]2(C3=C(C([H])=C(C([H])=C3[H])C([H])(C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])[C@@]12[H])C([H])([H])[H] |
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InChI Identifier | InChI=1S/C20H28O2/c1-13(2)14-6-8-16-15(12-14)7-9-17-19(16,3)10-5-11-20(17,4)18(21)22/h6,8,12-13,17H,5,7,9-11H2,1-4H3,(H,21,22)/t17-,19-,20-/m1/s1 |
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InChI Key | NFWKVWVWBFBAOV-MISYRCLQSA-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, 600 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, C6D6 (H),CDCl3 (C), simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, C6D6 (H),CDCl3 (C), 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 diterpenoids. These are terpene compounds formed by four 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 | Diterpenoids |
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Direct Parent | Diterpenoids |
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Alternative Parents | |
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Substituents | - Diterpenoid
- Abietane diterpenoid
- Phenanthrene
- Hydrophenanthrene
- Tetralin
- Benzenoid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aromatic homopolycyclic compound
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Molecular Framework | Aromatic homopolycyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Not Available |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Castrillo JI, Zeef LA, Hoyle DC, Zhang N, Hayes A, Gardner DC, Cornell MJ, Petty J, Hakes L, Wardleworth L, Rash B, Brown M, Dunn WB, Broadhurst D, O'Donoghue K, Hester SS, Dunkley TP, Hart SR, Swainston N, Li P, Gaskell SJ, Paton NW, Lilley KS, Kell DB, Oliver SG: Growth control of the eukaryote cell: a systems biology study in yeast. J Biol. 2007;6(2):4. doi: 10.1186/jbiol54. [PubMed:17439666 ]
- Johansen JD, Heydorn S, Menne T: Oak moss extracts in the diagnosis of fragrance contact allergy. Contact Dermatitis. 2002 Mar;46(3):157-61. doi: 10.1034/j.1600-0536.2002.460306.x. [PubMed:12000325 ]
- Kang MS, Hirai S, Goto T, Kuroyanagi K, Kim YI, Ohyama K, Uemura T, Lee JY, Sakamoto T, Ezaki Y, Yu R, Takahashi N, Kawada T: Dehydroabietic acid, a diterpene, improves diabetes and hyperlipidemia in obese diabetic KK-Ay mice. Biofactors. 2009 Sep-Oct;35(5):442-8. doi: 10.1002/biof.58. [PubMed:19753653 ]
- Jang HJ, Yang KS: Inhibition of nitric oxide production in RAW 264.7 macrophages by diterpenoids from Phellinus pini. Arch Pharm Res. 2011 Jun;34(6):913-7. doi: 10.1007/s12272-011-0608-z. Epub 2011 Jul 2. [PubMed:21725812 ]
- Xu X, Duan W, Huang M, Li G: Synthesis of cellulose dehydroabietate in ionic liquid [bmim]Br. Carbohydr Res. 2011 Sep 27;346(13):2024-7. doi: 10.1016/j.carres.2011.06.011. Epub 2011 Jun 16. [PubMed:21742316 ]
- van Beek, T. A., et al. (2007). van Beek, T. A., et al, J. Nat. Prod. 70, 154 (2007) . J. Nat. Prod..
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