| 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 00:42:35 UTC |
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| Update Date | 2022-03-07 02:56:09 UTC |
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| HMDB ID | HMDB0039299 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | 3,3'-Di-O-galloylprocyanidin B5 |
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| Description | 3,3'-Di-O-galloylprocyanidin 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-galloylprocyanidin B5 has been detected, but not quantified in, several different foods, such as red tea, black tea, herbal tea, green tea, and green vegetables. This could make 3,3'-di-O-galloylprocyanidin 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-galloylprocyanidin B5. |
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| Structure | OC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C3=C(O[C@@H]([C@@H](C3)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)C(O)=C1 InChI=1S/C44H34O20/c45-19-11-25(50)34-32(12-19)62-41(16-2-4-22(47)24(49)6-16)42(64-44(60)18-9-29(54)39(58)30(55)10-18)36(34)35-26(51)14-31-20(37(35)56)13-33(40(61-31)15-1-3-21(46)23(48)5-15)63-43(59)17-7-27(52)38(57)28(53)8-17/h1-12,14,33,36,40-42,45-58H,13H2/t33-,36-,40-,41-,42-/m1/s1 |
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| Synonyms | | Value | Source |
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| 3-O-Galloylepicatechin-(4beta->6)-epicatechin-3-O-gallate | HMDB | | Procyanidin b-5 3,3'-di-O-gallate | HMDB | | Procyanidin b5 3,3'-di-O-gallate | HMDB | | (2R,3R)-2-(3,4-Dihydroxyphenyl)-6-[(2R,3R,4S)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoic acid | Generator | | Procyanidin b5 3,3'-digallic acid | Generator |
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| Chemical Formula | C44H34O20 |
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| Average Molecular Weight | 882.7288 |
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| Monoisotopic Molecular Weight | 882.164343528 |
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| IUPAC Name | (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate |
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| Traditional Name | (2R,3R,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-6-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate |
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| CAS Registry Number | 106533-60-2 |
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| SMILES | OC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC=C(O)C(O)=C2)C2=C(O)C3=C(O[C@@H]([C@@H](C3)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)C(O)=C1 |
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| InChI Identifier | InChI=1S/C44H34O20/c45-19-11-25(50)34-32(12-19)62-41(16-2-4-22(47)24(49)6-16)42(64-44(60)18-9-29(54)39(58)30(55)10-18)36(34)35-26(51)14-31-20(37(35)56)13-33(40(61-31)15-1-3-21(46)23(48)5-15)63-43(59)17-7-27(52)38(57)28(53)8-17/h1-12,14,33,36,40-42,45-58H,13H2/t33-,36-,40-,41-,42-/m1/s1 |
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| InChI Key | LFBGVECYPPCVDS-QNPRKUGLSA-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
- Catechin
- Hydroxyflavonoid
- Flavan-3-ol
- 3'-hydroxyflavonoid
- 7-hydroxyflavonoid
- 5-hydroxyflavonoid
- 4'-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
- Catechol
- Alkyl aryl ether
- Phenol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Dicarboxylic acid or derivatives
- Benzenoid
- Monocyclic benzene moiety
- Carboxylic acid ester
- Polyol
- Ether
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Organic oxide
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- 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. | 3.42 minutes | 32390414 | | Predicted by Siyang on May 30, 2022 | 14.349 minutes | 33406817 | | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 3.79 minutes | 32390414 | | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 92.5 seconds | 40023050 | | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 2074.9 seconds | 40023050 | | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 119.2 seconds | 40023050 | | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 125.0 seconds | 40023050 | | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 88.5 seconds | 40023050 | | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 167.0 seconds | 40023050 | | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 1019.1 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 | 630.2 seconds | 40023050 | | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 842.9 seconds | 40023050 | | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 910.5 seconds | 40023050 | | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 513.9 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 | 1859.0 seconds | 40023050 | | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 336.1 seconds | 40023050 | | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 445.5 seconds | 40023050 | | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 446.8 seconds | 40023050 | | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 444.9 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 | 635.8 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatized |
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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-galloylprocyanidin B5 10V, Positive-QTOF | splash10-0h0r-0510090450-63ffcd0d28bc59174ac6 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 20V, Positive-QTOF | splash10-0f6x-0962370210-d5100a5daad246a350c4 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 40V, Positive-QTOF | splash10-0zfr-0980010010-d685131fe4fbd1c54354 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 10V, Negative-QTOF | splash10-001i-0300000390-81e6ebc0684396851459 | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 20V, Negative-QTOF | splash10-0gdi-0903100440-bbdd35b047bcb5fc9ecf | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 40V, Negative-QTOF | splash10-016r-0900001000-b02b0171cd108205f5ed | 2016-08-03 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 10V, Negative-QTOF | splash10-003r-0010000590-2866434216c3712c0e99 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 20V, Negative-QTOF | splash10-03e9-0501120790-93b127f1f166f07b2c83 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 40V, Negative-QTOF | splash10-00b9-1300010290-47d215c25d269d17708c | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 10V, Positive-QTOF | splash10-02h9-0100012960-9834338d49f07b6c2547 | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 20V, Positive-QTOF | splash10-01si-0300132890-6c868b630a67f9eac48d | 2021-09-24 | Wishart Lab | View Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 3,3'-Di-O-galloylprocyanidin B5 40V, Positive-QTOF | splash10-004i-0500041490-5256c67a9468e6492173 | 2021-09-24 | Wishart Lab | View Spectrum |
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