| 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 19:54:21 UTC |
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| Update Date | 2022-03-07 02:54:18 UTC |
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| HMDB ID | HMDB0034971 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | (1R,2R,3S,1'R)-Nepetalinic acid |
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| Description | (1R,2R,3S,1'R)-Nepetalinic acid, also known as (1R,2R,3S,1'r)-nepetalinate, belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. Based on a literature review a small amount of articles have been published on (1R,2R,3S,1'R)-Nepetalinic acid. |
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| Structure | CC(C1CCC(C)C1C(O)=O)C(O)=O InChI=1S/C10H16O4/c1-5-3-4-7(6(2)9(11)12)8(5)10(13)14/h5-8H,3-4H2,1-2H3,(H,11,12)(H,13,14) |
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| Synonyms | | Value | Source |
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| (1R,2R,3S,1'r)-Nepetalinate | Generator | | 2-(1-Carboxyethyl)-5-methylcyclopentane-1-carboxylate | HMDB |
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| Chemical Formula | C10H16O4 |
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| Average Molecular Weight | 200.2316 |
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| Monoisotopic Molecular Weight | 200.104859 |
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| IUPAC Name | 2-(1-carboxyethyl)-5-methylcyclopentane-1-carboxylic acid |
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| Traditional Name | 2-(1-carboxyethyl)-5-methylcyclopentane-1-carboxylic acid |
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| CAS Registry Number | 32603-11-5 |
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| SMILES | CC(C1CCC(C)C1C(O)=O)C(O)=O |
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| InChI Identifier | InChI=1S/C10H16O4/c1-5-3-4-7(6(2)9(11)12)8(5)10(13)14/h5-8H,3-4H2,1-2H3,(H,11,12)(H,13,14) |
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| InChI Key | OIFCPZGZZQQDNO-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as monocyclic monoterpenoids. These are monoterpenoids containing 1 ring in the isoprene chain. |
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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 | Monoterpenoids |
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| Direct Parent | Monocyclic monoterpenoids |
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| Alternative Parents | |
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| Substituents | - Monocyclic monoterpenoid
- Dicarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Organooxygen compound
- Carbonyl group
- Aliphatic homomonocyclic compound
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| Molecular Framework | Aliphatic homomonocyclic 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 | Not Available |
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| Role | Not Available |
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| Physical Properties |
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| State | Solid |
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| Experimental Molecular Properties | |
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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 Retention Times Underivatized| Chromatographic Method | Retention Time | Reference |
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| Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. | 3.4 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 10.6923 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 1.59 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 101.8 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 1511.8 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 273.4 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 106.4 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 167.6 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 103.1 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 368.8 seconds | 40023050 | | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 425.8 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 106.9 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 762.3 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 351.1 seconds | 40023050 | | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 1045.1 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 218.4 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 314.8 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 361.7 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 219.4 seconds | 40023050 | | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 208.7 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized| Derivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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| (1R,2R,3S,1'R)-Nepetalinic acid,1TMS,isomer #1 | CC1CCC(C(C)C(=O)O)C1C(=O)O[Si](C)(C)C | 1643.4 | Semi standard non polar | 33892256 | | (1R,2R,3S,1'R)-Nepetalinic acid,1TMS,isomer #2 | CC1CCC(C(C)C(=O)O[Si](C)(C)C)C1C(=O)O | 1677.0 | Semi standard non polar | 33892256 | | (1R,2R,3S,1'R)-Nepetalinic acid,2TMS,isomer #1 | CC1CCC(C(C)C(=O)O[Si](C)(C)C)C1C(=O)O[Si](C)(C)C | 1685.4 | Semi standard non polar | 33892256 | | (1R,2R,3S,1'R)-Nepetalinic acid,1TBDMS,isomer #1 | CC1CCC(C(C)C(=O)O)C1C(=O)O[Si](C)(C)C(C)(C)C | 1896.7 | Semi standard non polar | 33892256 | | (1R,2R,3S,1'R)-Nepetalinic acid,1TBDMS,isomer #2 | CC1CCC(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1C(=O)O | 1925.7 | Semi standard non polar | 33892256 | | (1R,2R,3S,1'R)-Nepetalinic acid,2TBDMS,isomer #1 | CC1CCC(C(C)C(=O)O[Si](C)(C)C(C)(C)C)C1C(=O)O[Si](C)(C)C(C)(C)C | 2131.1 | Semi standard non polar | 33892256 |
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| GC-MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted GC-MS | Predicted GC-MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-0pbc-9800000000-0f572492f0c92488312f | 2017-09-01 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid GC-MS (2 TMS) - 70eV, Positive | splash10-00bi-9362000000-7a98525d253a6a9ea4a4 | 2017-10-06 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 10V, Positive-QTOF | splash10-0zgi-0940000000-0e5748304e4a54e0224a | 2016-08-02 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 20V, Positive-QTOF | splash10-0a59-2900000000-14ee6157af01f646837a | 2016-08-02 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 40V, Positive-QTOF | splash10-0pb9-9300000000-c8df20d12196a9064d02 | 2016-08-02 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 10V, Negative-QTOF | splash10-052b-0900000000-a673b2e575c19e7283d7 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 20V, Negative-QTOF | splash10-0a4i-0900000000-f67859ddd6e2ee21c6ed | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 40V, Negative-QTOF | splash10-0c0r-8900000000-aed64bb80becde8315a8 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 10V, Positive-QTOF | splash10-0pc9-0920000000-a54b278f57d03315107a | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 20V, Positive-QTOF | splash10-0a4i-6900000000-cc290fc2938bb573ef9e | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 40V, Positive-QTOF | splash10-066u-9000000000-0376933603017085c162 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 10V, Negative-QTOF | splash10-054k-1900000000-ac8cc608cbe2c7cc428e | 2021-09-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 20V, Negative-QTOF | splash10-0bt9-0900000000-87f6863d6c4b9ae08c24 | 2021-09-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (1R,2R,3S,1'R)-Nepetalinic acid 40V, Negative-QTOF | splash10-0560-9700000000-bbe82686eac1ebcda6f9 | 2021-09-23 | Wishart Lab | View Spectrum |
NMR Spectra| Spectrum Type | Description | Deposition Date | Source | View |
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| Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum | | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-25 | Wishart Lab | View Spectrum |
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