Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 21:52:05 UTC |
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Update Date | 2022-03-07 02:55:01 UTC |
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HMDB ID | HMDB0036701 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid |
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Description | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid, also known as (ent-6α,7α,12α)-6,7,12-trihydroxy-16-kauren-19-Oate, belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). |
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Structure | CC12CCCC(C)(C1C(O)C(O)C13CC(C(O)CC21)C(=C)C3)C(O)=O InChI=1S/C20H30O5/c1-10-8-20-9-11(10)12(21)7-13(20)18(2)5-4-6-19(3,17(24)25)15(18)14(22)16(20)23/h11-16,21-23H,1,4-9H2,2-3H3,(H,24,25) |
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Synonyms | Value | Source |
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(ent-6a,7a,12a)-6,7,12-Trihydroxy-16-kauren-19-Oate | Generator | (ent-6a,7a,12a)-6,7,12-Trihydroxy-16-kauren-19-Oic acid | Generator | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-Oate | Generator | (ent-6Α,7α,12α)-6,7,12-trihydroxy-16-kauren-19-Oate | Generator | (ent-6Α,7α,12α)-6,7,12-trihydroxy-16-kauren-19-Oic acid | Generator | 2,3,12-Trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylate | Generator |
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Chemical Formula | C20H30O5 |
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Average Molecular Weight | 350.4492 |
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Monoisotopic Molecular Weight | 350.20932407 |
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IUPAC Name | 2,3,12-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid |
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Traditional Name | 2,3,12-trihydroxy-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carboxylic acid |
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CAS Registry Number | 90806-33-0 |
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SMILES | CC12CCCC(C)(C1C(O)C(O)C13CC(C(O)CC21)C(=C)C3)C(O)=O |
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InChI Identifier | InChI=1S/C20H30O5/c1-10-8-20-9-11(10)12(21)7-13(20)18(2)5-4-6-19(3,17(24)25)15(18)14(22)16(20)23/h11-16,21-23H,1,4-9H2,2-3H3,(H,24,25) |
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InChI Key | GDUDOACZUAVXMK-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as kaurane diterpenoids. These are diterpene alkaloids with a structure that is based on the kaurane skeleton. Kaurane is a tetracyclic compound that arises by cyclisation of a pimarane precursor followed by rearrangement. It possesses a [3,2,1]-bicyclic ring system with C15-C16 bridge connected to C13, forming the five-membered ring D. |
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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 | Kaurane diterpenoids |
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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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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Not Available |
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Experimental Molecular 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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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedMetabolite | SMILES | Kovats RI Value | Column Type | Reference |
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(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid | CC12CCCC(C)(C1C(O)C(O)C13CC(C(O)CC21)C(=C)C3)C(O)=O | 3066.3 | Standard polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid | CC12CCCC(C)(C1C(O)C(O)C13CC(C(O)CC21)C(=C)C3)C(O)=O | 2793.1 | Standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid | CC12CCCC(C)(C1C(O)C(O)C13CC(C(O)CC21)C(=C)C3)C(O)=O | 3016.2 | Semi standard non polar | 33892256 |
DerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TMS,isomer #1 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C)C3O | 3015.8 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TMS,isomer #2 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O)C1C(O)C3O[Si](C)(C)C | 3007.0 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TMS,isomer #3 | C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O)C3O | 3030.9 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TMS,isomer #4 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O)C3O | 2947.1 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TMS,isomer #1 | C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C)C3O | 2946.1 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TMS,isomer #2 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O[Si](C)(C)C)C3O | 2913.3 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TMS,isomer #3 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C)C3O[Si](C)(C)C | 2985.5 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TMS,isomer #4 | C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O)C3O[Si](C)(C)C | 2956.6 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TMS,isomer #5 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O)C3O[Si](C)(C)C | 2891.2 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TMS,isomer #6 | C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O)C3O | 2939.6 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TMS,isomer #1 | C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O[Si](C)(C)C)C3O | 2862.4 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TMS,isomer #2 | C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C)C3O[Si](C)(C)C | 2912.1 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TMS,isomer #3 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O[Si](C)(C)C)C3O[Si](C)(C)C | 2902.4 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TMS,isomer #4 | C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O)C3O[Si](C)(C)C | 2862.8 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,4TMS,isomer #1 | C=C1CC23CC1C(O[Si](C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C)C1C(O[Si](C)(C)C)C3O[Si](C)(C)C | 2875.8 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TBDMS,isomer #1 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C(C)(C)C)C3O | 3266.2 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TBDMS,isomer #2 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O)C1C(O)C3O[Si](C)(C)C(C)(C)C | 3250.6 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TBDMS,isomer #3 | C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O)C3O | 3275.5 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,1TBDMS,isomer #4 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O)C3O | 3224.6 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TBDMS,isomer #1 | C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C(C)(C)C)C3O | 3424.2 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TBDMS,isomer #2 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O[Si](C)(C)C(C)(C)C)C3O | 3413.7 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TBDMS,isomer #3 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C | 3483.0 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TBDMS,isomer #4 | C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O)C3O[Si](C)(C)C(C)(C)C | 3424.3 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TBDMS,isomer #5 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O)C3O[Si](C)(C)C(C)(C)C | 3387.8 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,2TBDMS,isomer #6 | C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O)C3O | 3431.7 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TBDMS,isomer #1 | C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O[Si](C)(C)C(C)(C)C)C3O | 3566.4 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TBDMS,isomer #2 | C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O)C1C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C | 3622.4 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TBDMS,isomer #3 | C=C1CC23CC1C(O)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C | 3618.8 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,3TBDMS,isomer #4 | C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O)C3O[Si](C)(C)C(C)(C)C | 3566.8 | Semi standard non polar | 33892256 | (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid,4TBDMS,isomer #1 | C=C1CC23CC1C(O[Si](C)(C)C(C)(C)C)CC2C1(C)CCCC(C)(C(=O)O[Si](C)(C)C(C)(C)C)C1C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C | 3792.3 | Semi standard non polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-053r-3539000000-69a6004b0e95d7a7768c | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid GC-MS (4 TMS) - 70eV, Positive | splash10-00di-1001169000-ab6a3b4aeae04d580374 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid 10V, Positive-QTOF | splash10-0f89-0019000000-f9db9a7526cb5f5096fd | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid 20V, Positive-QTOF | splash10-00li-0159000000-de2a349411ad318f24f2 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid 40V, Positive-QTOF | splash10-000i-5294000000-8750b5aacd1fddcdf052 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid 10V, Negative-QTOF | splash10-0002-0019000000-cd4d4a13f20040b0016b | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid 20V, Negative-QTOF | splash10-053j-0049000000-cb78c8c447f071d13495 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid 40V, Negative-QTOF | splash10-000i-3097000000-d6cf9a8e8011d40ce5dc | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid 10V, Negative-QTOF | splash10-0002-0009000000-fcf5b98fd26ec15b6b62 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid 20V, Negative-QTOF | splash10-0002-0029000000-10965c6d72d1642fa0f3 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid 40V, Negative-QTOF | splash10-0012-1059000000-5312b617a5c9332dc98b | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid 10V, Positive-QTOF | splash10-0udi-0009000000-da9110d5056c23c2b133 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid 20V, Positive-QTOF | splash10-0uyr-1089000000-7de39006620ff7b695b5 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (ent-6alpha,7alpha,12alpha)-6,7,12-Trihydroxy-16-kauren-19-oic acid 40V, Positive-QTOF | splash10-0673-9374000000-273adce0b43d507b1e25 | 2021-09-25 | Wishart Lab | View Spectrum |
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