| 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 23:39:43 UTC |
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| Update Date | 2022-03-07 02:55:44 UTC |
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| HMDB ID | HMDB0038360 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Theasinensin A |
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| Description | Theasinensin A belongs to the class of organic compounds known as complex tannins. These are tannins made of a catechin bound to a gallotannin or elagitannin. Theasinensin A is found, on average, in the highest concentration within a few different foods, such as teas (Camellia sinensis), red tea, and herbal tea and in a lower concentration in green tea and black tea. This could make theasinensin a a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Theasinensin A. |
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| Structure | OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC(O)=C(O)C(O)=C2C2=C(C=C(O)C(O)=C2O)[C@H]2OC3=C(C[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)=CC(O)=C3)C(O)=C1 InChI=1S/C44H34O22/c45-15-5-21(47)17-11-31(65-43(61)13-1-23(49)35(55)24(50)2-13)41(63-29(17)7-15)19-9-27(53)37(57)39(59)33(19)34-20(10-28(54)38(58)40(34)60)42-32(12-18-22(48)6-16(46)8-30(18)64-42)66-44(62)14-3-25(51)36(56)26(52)4-14/h1-10,31-32,41-42,45-60H,11-12H2/t31-,32-,41-,42-/m1/s1 |
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| Synonyms | Not Available |
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| Chemical Formula | C44H34O22 |
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| Average Molecular Weight | 914.734 |
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| Monoisotopic Molecular Weight | 914.154172735 |
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| IUPAC Name | (2R,3R)-2-{6'-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-2-yl]-2',3',4,4',5,6-hexahydroxy-[1,1'-biphenyl]-2-yl}-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate |
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| Traditional Name | (2R,3R)-2-{6'-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-2-yl]-2',3',4,4',5,6-hexahydroxy-[1,1'-biphenyl]-2-yl}-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate |
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| CAS Registry Number | 89064-31-3 |
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| SMILES | OC1=CC2=C(C[C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC(O)=C(O)C(O)=C2C2=C(C=C(O)C(O)=C2O)[C@H]2OC3=C(C[C@H]2OC(=O)C2=CC(O)=C(O)C(O)=C2)C(O)=CC(O)=C3)C(O)=C1 |
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| InChI Identifier | InChI=1S/C44H34O22/c45-15-5-21(47)17-11-31(65-43(61)13-1-23(49)35(55)24(50)2-13)41(63-29(17)7-15)19-9-27(53)37(57)39(59)33(19)34-20(10-28(54)38(58)40(34)60)42-32(12-18-22(48)6-16(46)8-30(18)64-42)66-44(62)14-3-25(51)36(56)26(52)4-14/h1-10,31-32,41-42,45-60H,11-12H2/t31-,32-,41-,42-/m1/s1 |
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| InChI Key | YUULFXAQUWEYNP-GXAWFILRSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as complex tannins. These are tannins made of a catechin bound to a gallotannin or elagitannin. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Tannins |
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| Sub Class | Complex tannins |
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| Direct Parent | Complex tannins |
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| Alternative Parents | |
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| Substituents | - Complex tannin
- Catechin gallate
- Epigallocatechin
- Catechin
- Flavan-3-ol
- Hydroxyflavonoid
- 7-hydroxyflavonoid
- 5-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 3'-hydroxyflavonoid
- Flavan
- Biphenol
- Galloyl ester
- Gallic acid or derivatives
- Biphenyl
- P-hydroxybenzoic acid ester
- M-hydroxybenzoic acid ester
- P-hydroxybenzoic acid alkyl ester
- 1-benzopyran
- Benzopyran
- Benzoate ester
- Chromane
- Benzenetriol
- Pyrogallol derivative
- Benzoic acid or derivatives
- Benzoyl
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- 1-hydroxy-4-unsubstituted benzenoid
- Monocyclic benzene moiety
- Benzenoid
- Dicarboxylic acid or derivatives
- Carboxylic acid ester
- Ether
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Carboxylic acid derivative
- Organooxygen compound
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic compounds |
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| External Descriptors | |
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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 | |
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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 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. Predicted by Afia on May 17, 2022. | 3.98 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 15.1409 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 3.89 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 101.9 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 1787.4 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 120.8 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 107.4 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 79.3 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 194.0 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 1088.9 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 | 574.8 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 1182.8 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 896.1 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 449.9 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 | 1924.5 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 308.6 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 438.4 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 576.2 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 582.3 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 | 784.5 seconds | 40023050 |
Predicted Kovats Retention IndicesNot Available |
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| MS/MS Spectra| Spectrum Type | Description | Splash Key | Deposition Date | Source | View |
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| Experimental LC-MS/MS | LC-MS/MS Spectrum - Theasinensin A , positive-QTOF | splash10-000i-0930300000-09eb58349fe15793d035 | 2017-09-14 | HMDB team, MONA | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Theasinensin A 10V, Positive-QTOF | splash10-00kr-0900000203-58c8d064e6520a64fef9 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Theasinensin A 20V, Positive-QTOF | splash10-0fe0-0900000100-66f241797c061dfe4381 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Theasinensin A 40V, Positive-QTOF | splash10-0fe0-1900000010-6d44b0c7bb14b5794b9c | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Theasinensin A 10V, Negative-QTOF | splash10-03di-0300000119-35c4d97fd0c28d371d3b | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Theasinensin A 20V, Negative-QTOF | splash10-07fr-0901211522-74eba17741422040ad24 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Theasinensin A 40V, Negative-QTOF | splash10-00or-0900000000-1ea7e5ed24733bccf719 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Theasinensin A 10V, Negative-QTOF | splash10-03di-0000000903-f57add13a8419943ef71 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Theasinensin A 20V, Negative-QTOF | splash10-03g0-0900000253-9bb7bc010bc2b859b955 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Theasinensin A 40V, Negative-QTOF | splash10-004i-0900000170-0819238d60a5ffea99e7 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Theasinensin A 10V, Positive-QTOF | splash10-00kb-0100000926-34ffa23f617263dbb9c9 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Theasinensin A 20V, Positive-QTOF | splash10-0gbj-0900000564-a0651e4364ae3c855c3a | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Theasinensin A 40V, Positive-QTOF | splash10-102a-1900020251-41265bea395eaa100ec5 | 2021-09-24 | Wishart Lab | View Spectrum |
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