Record Information |
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Version | 1.0 |
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Created at | 2020-12-09 03:43:43 UTC |
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Updated at | 2021-08-19 23:59:42 UTC |
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NP-MRD ID | NP0006794 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Alpha-Gurjunene |
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Provided By | NPAtlas![NPAtlas Logo](/attributions/npatlas_logo_square_small.png) |
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Description | Gurjunene-alpha, also known as gurjunene-α, belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Gurjunene-alpha 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. Alpha-Gurjunene is found in Aloysia citrodora, Aristolochia elegans, Artemisia vulgaris, Arum maculatum, Austromyrtus dulcis, Baccharis articulata, Balsamum tolutanum, Cinnamomum parthenoxylon, Cistus incanus, Cistus monspeliensis, Commiphora sphaerocarpa, Cyperus rotundus L. , Dipterocarpus kerrii, Duguetia confinis, Eucalyptus cloeziana, Eucalyptus globulus, Grindelia hirsutula, Hedyosmum costaricense, Helichrysum italicum, Helichrysum nudifolium, Helichrysum odoratissimum, Helichrysum stoechas, Humulus lupulus, Hypericum hircinum, Lavandula latifolia, Lavandula stoechas, Lepechinia chamaedryoides, Lepechinia floribunda, Melaleuca alternifolia, Melaleuca quinquenervia, Micromeria sinaica, Myroxylon balsamum var.balsamum , Osbornia octodonta, Ozothamnus retusus, Pelargonium quercifolium, Pimenta racemosa, Piper gaudichaudianum, Piper guineense, Plagiochila rutilans, Porella canariensis, Pseudowintera colorata, Salvia reuteriana, Santolina chamaecyparissus, Schinus molle, Senecio linearifolius, Solidago gigantea, Streptomyces, Syzygium nervosum, Teucrium pestalozzae, Thymus broussonetti, Thymus maroccanus, Thymus marschallianus, Thymus praecos, Toona ciliata, Valeriana officinalis, Vitex agnus-castus and Vitex negundo. It was first documented in 1999 (PMID: 10190971). Based on a literature review a small amount of articles have been published on Gurjunene-alpha (PMID: 17193176) (PMID: 19731610) (PMID: 23365607) (PMID: 24371539). |
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Structure | [H]C([H])([H])C1=C2[C@@]3([H])[C@@]([H])(C([H])([H])C([H])([H])[C@@]([H])(C([H])([H])[H])[C@@]2([H])C([H])([H])C1([H])[H])C3(C([H])([H])[H])C([H])([H])[H] InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h9,11-12,14H,5-8H2,1-4H3/t9-,11-,12-,14-/m1/s1 |
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Synonyms | Value | Source |
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Gurjunene-a | Generator | Gurjunene-α | Generator | (-)-a-Gurjunene | HMDB | (-)-Α-gurjunene | HMDB | a-Gurjunene | HMDB | Α-gurjunene | HMDB |
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Chemical Formula | C15H24 |
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Average Mass | 204.3570 Da |
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Monoisotopic Mass | 204.18780 Da |
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IUPAC Name | (1aS,4aR,5R,7aR)-1,1,2,5-tetramethyl-1H,1aH,3H,4H,4aH,5H,6H,7H,7aH-cyclopropa[e]azulene |
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Traditional Name | (1aS,4aR,5R,7aR)-1,1,2,5-tetramethyl-1aH,3H,4H,4aH,5H,6H,7H,7aH-cyclopropa[e]azulene |
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CAS Registry Number | Not Available |
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SMILES | C[C@@H]1CC[C@@H]2[C@H](C3=C(C)CC[C@H]13)C2(C)C |
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InChI Identifier | InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h9,11-12,14H,5-8H2,1-4H3/t9-,11-,12-,14-/m1/s1 |
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InChI Key | SPCXZDDGSGTVAW-XIDUGBJDSA-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, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, 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 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. |
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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 | Sesquiterpenoids |
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Direct Parent | 5,10-cycloaromadendrane sesquiterpenoids |
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Alternative Parents | Not Available |
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Substituents | Not Available |
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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 | |
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Predicted Properties | |
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