| Record Information |
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| Version | 5.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2012-09-12 00:42:40 UTC |
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| Update Date | 2022-03-07 02:56:09 UTC |
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| HMDB ID | HMDB0039300 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 3,3'-Di-O-galloylprodelphinidin B5 |
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| Description | 3,3'-Di-O-galloylprodelphinidin B5 belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. 3,3'-Di-O-galloylprodelphinidin B5 has been detected, but not quantified in, several different foods, such as herbal tea, red tea, green tea, black tea, and fruits. This could make 3,3'-di-O-galloylprodelphinidin B5 a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3,3'-Di-O-galloylprodelphinidin B5. |
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| Structure | OC1=CC(O)=C2C(C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(OC2=C1)C1=CC(O)=C(O)C(O)=C1)C1=C(O)C2=C(OC(C(C2)OC(=O)C2=CC(O)=C(O)C(O)=C2)C2=CC(O)=C(O)C(O)=C2)C=C1O InChI=1S/C44H34O22/c45-17-9-19(46)32-30(10-17)64-41(14-3-23(50)37(58)24(51)4-14)42(66-44(62)16-7-27(54)39(60)28(55)8-16)34(32)33-20(47)12-29-18(35(33)56)11-31(40(63-29)13-1-21(48)36(57)22(49)2-13)65-43(61)15-5-25(52)38(59)26(53)6-15/h1-10,12,31,34,40-42,45-60H,11H2 |
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| Synonyms | | Value | Source |
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| 3-O-Galloylepigallocatechin-(4beta->6)-epigallocatechin-3-O-gallate | HMDB | | 6-[5,7-Dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acid | Generator | | Prodelphinidin b5 3,3'-digallic acid | Generator |
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| Chemical Formula | C44H34O22 |
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| Average Molecular Weight | 914.7276 |
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| Monoisotopic Molecular Weight | 914.154172772 |
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| IUPAC Name | 4-[5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate |
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| Traditional Name | 4-[5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate |
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| CAS Registry Number | 86588-87-6 |
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| SMILES | OC1=CC(O)=C2C(C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C(OC2=C1)C1=CC(O)=C(O)C(O)=C1)C1=C(O)C2=C(OC(C(C2)OC(=O)C2=CC(O)=C(O)C(O)=C2)C2=CC(O)=C(O)C(O)=C2)C=C1O |
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| InChI Identifier | InChI=1S/C44H34O22/c45-17-9-19(46)32-30(10-17)64-41(14-3-23(50)37(58)24(51)4-14)42(66-44(62)16-7-27(54)39(60)28(55)8-16)34(32)33-20(47)12-29-18(35(33)56)11-31(40(63-29)13-1-21(48)36(57)22(49)2-13)65-43(61)15-5-25(52)38(59)26(53)6-15/h1-10,12,31,34,40-42,45-60H,11H2 |
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| InChI Key | LXQFRGHXODSYNA-UHFFFAOYSA-N |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Flavonoids |
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| Sub Class | Biflavonoids and polyflavonoids |
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| Direct Parent | Biflavonoids and polyflavonoids |
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| Alternative Parents | |
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| Substituents | - B-type proanthocyanidin
- Proanthocyanidin
- Bi- and polyflavonoid skeleton
- Catechin gallate
- Epigallocatechin
- Catechin
- Hydroxyflavonoid
- Flavan-3-ol
- 3'-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 7-hydroxyflavonoid
- 5-hydroxyflavonoid
- Flavan
- Galloyl ester
- Gallic acid or derivatives
- M-hydroxybenzoic acid ester
- P-hydroxybenzoic acid ester
- P-hydroxybenzoic acid alkyl ester
- Benzoate ester
- Chromane
- Benzopyran
- 1-benzopyran
- Benzenetriol
- Benzoic acid or derivatives
- Pyrogallol derivative
- Benzoyl
- Phenol
- Alkyl aryl ether
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Benzenoid
- Dicarboxylic acid or derivatives
- Monocyclic benzene moiety
- Carboxylic acid ester
- Polyol
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Ether
- Organooxygen compound
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic 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 | |
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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. | 3.85 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 14.3696 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 4.2 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 134.4 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 1748.8 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 118.9 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 102.3 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 80.8 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 144.5 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 1005.8 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 | 582.1 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 1152.6 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 870.2 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 400.3 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 | 1777.5 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 288.6 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 421.1 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 562.1 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 609.5 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 | 865.1 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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| Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprodelphinidin B5 10V, Positive-QTOF | splash10-0002-0300190413-ce42604eb3d32e1e8cf4 | 2016-08-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprodelphinidin B5 20V, Positive-QTOF | splash10-0pbc-0980782110-fea4e15c428f42b78d11 | 2016-08-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprodelphinidin B5 40V, Positive-QTOF | splash10-0zfr-0890210000-b7b8d1e97cf75646daf2 | 2016-08-01 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprodelphinidin B5 10V, Negative-QTOF | splash10-03di-0300000419-346ebf0304fbb30c54a5 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprodelphinidin B5 20V, Negative-QTOF | splash10-016r-0904100731-0149d58a6f91efc7d62d | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprodelphinidin B5 40V, Negative-QTOF | splash10-016r-0901100200-6cd565d8d06ede8f51ca | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprodelphinidin B5 10V, Negative-QTOF | splash10-03di-0000000109-96a7bc0c71d93a40c23c | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprodelphinidin B5 20V, Negative-QTOF | splash10-01p5-0500010962-459650ca9e1cf0f93a25 | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprodelphinidin B5 40V, Negative-QTOF | splash10-056r-0900210180-9c3dfc964fb9cd59ef8b | 2021-09-22 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprodelphinidin B5 10V, Positive-QTOF | splash10-00ks-0000005911-6375c3c7e0bc75d31115 | 2021-09-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprodelphinidin B5 20V, Positive-QTOF | splash10-0aos-0510600696-37402cdfee6478a42f2f | 2021-09-23 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprodelphinidin B5 40V, Positive-QTOF | splash10-0ktg-0600023893-38a7061ee7ac920a8dce | 2021-09-23 | Wishart Lab | View Spectrum |
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