Record Information |
---|
Version | 5.0 |
---|
Status | Expected but not Quantified |
---|
Creation Date | 2021-09-23 18:22:57 UTC |
---|
Update Date | 2021-09-23 18:22:57 UTC |
---|
HMDB ID | HMDB0302517 |
---|
Secondary Accession Numbers | None |
---|
Metabolite Identification |
---|
Common Name | Proanthocyanidins |
---|
Description | Proanthocyanidins, also known as zangrado or polyhydroxyflavan-3-ol, is a member of the class of compounds known as biflavonoids and polyflavonoids. Biflavonoids and polyflavonoids 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''. Proanthocyanidins is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Proanthocyanidins can be found in a number of food items such as roselle, allspice, cocoa bean, and sweet bay, which makes proanthocyanidins a potential biomarker for the consumption of these food products. Proanthocyanidins were discovered in 1947 by Jacques Masquelier, who developed and patented techniques for the extraction of oligomeric proanthocyanidins from pine bark and grape seeds. Often associated with consumer products made from cranberries, grape seeds or red wine, proanthocyanidins were once proposed as factors inhibiting urinary tract infections in women, but this research has been refuted by expert scientific committees . |
---|
Structure | [H][C@@]1(O)CC2=C(OC1([H])C1=CC(O)=C(OC)C(O)=C1)C(=C(O)C=C2O)[C@@]1([H])C2=C(O)C=C(O)C=C2O[C@]([H])(C2=CC=C(O)C=C2)[C@]1([H])O InChI=1S/C31H28O12/c1-41-31-20(37)6-13(7-21(31)38)28-22(39)10-16-17(34)11-19(36)25(30(16)43-28)26-24-18(35)8-15(33)9-23(24)42-29(27(26)40)12-2-4-14(32)5-3-12/h2-9,11,22,26-29,32-40H,10H2,1H3/t22-,26-,27-,28?,29-/m1/s1 |
---|
Synonyms | Value | Source |
---|
Zangrado | MeSH | Polyhydroxyflavan-3-ol | MeSH | Proanthocyanidins | MeSH | Polymers, anthocyanidin | MeSH | Procyanidins | MeSH | Anthocyanidin polymers | MeSH | Condensed tannin | MeSH | Condensed tannins | MeSH | Tannin, condensed | MeSH | Tannins, condensed | MeSH | Proanthocyanidin | MeSH |
|
---|
Chemical Formula | C31H28O12 |
---|
Average Molecular Weight | 592.553 |
---|
Monoisotopic Molecular Weight | 592.158076342 |
---|
IUPAC Name | (2R,3R,4R)-4-[(3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol |
---|
Traditional Name | (2R,3R,4R)-4-[(3R)-2-(3,5-dihydroxy-4-methoxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-8-yl]-2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol |
---|
CAS Registry Number | Not Available |
---|
SMILES | [H][C@@]1(O)CC2=C(OC1([H])C1=CC(O)=C(OC)C(O)=C1)C(=C(O)C=C2O)[C@@]1([H])C2=C(O)C=C(O)C=C2O[C@]([H])(C2=CC=C(O)C=C2)[C@]1([H])O |
---|
InChI Identifier | InChI=1S/C31H28O12/c1-41-31-20(37)6-13(7-21(31)38)28-22(39)10-16-17(34)11-19(36)25(30(16)43-28)26-24-18(35)8-15(33)9-23(24)42-29(27(26)40)12-2-4-14(32)5-3-12/h2-9,11,22,26-29,32-40H,10H2,1H3/t22-,26-,27-,28?,29-/m1/s1 |
---|
InChI Key | JPFCOVZKLAXXOE-XBNSMERZSA-N |
---|
Chemical Taxonomy |
---|
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''. |
---|
Kingdom | Organic compounds |
---|
Super Class | Phenylpropanoids and polyketides |
---|
Class | Flavonoids |
---|
Sub Class | Biflavonoids and polyflavonoids |
---|
Direct Parent | Biflavonoids and polyflavonoids |
---|
Alternative Parents | |
---|
Substituents | - B-type proanthocyanidin
- Bi- and polyflavonoid skeleton
- Proanthocyanidin
- Epigallocatechin
- Catechin
- 4p-methoxyflavonoid-skeleton
- 3'-hydroxyflavonoid
- 3-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavan-3-ol
- Hydroxyflavonoid
- Flavan
- Chromane
- Benzopyran
- 1-benzopyran
- Methoxyphenol
- Resorcinol
- Phenol ether
- Anisole
- Phenoxy compound
- Methoxybenzene
- Phenol
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- 1-hydroxy-4-unsubstituted benzenoid
- Benzenoid
- Monocyclic benzene moiety
- Secondary alcohol
- Polyol
- Ether
- Oxacycle
- Organoheterocyclic compound
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Organic oxygen compound
- Aromatic heteropolycyclic compound
|
---|
Molecular Framework | Aromatic heteropolycyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Physiological effect | Not Available |
---|
Disposition | |
---|
Process | Not Available |
---|
Role | |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Molecular Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | |
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
Proanthocyanidins,2TMS,isomer #16 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 5441.5 | Semi standard non polar | 33892256 | Proanthocyanidins,2TMS,isomer #16 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 4695.2 | Standard non polar | 33892256 | Proanthocyanidins,2TMS,isomer #16 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 7504.8 | Standard polar | 33892256 | Proanthocyanidins,3TMS,isomer #13 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 5264.1 | Semi standard non polar | 33892256 | Proanthocyanidins,3TMS,isomer #13 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 4541.4 | Standard non polar | 33892256 | Proanthocyanidins,3TMS,isomer #13 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 6949.2 | Standard polar | 33892256 | Proanthocyanidins,3TMS,isomer #34 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 5249.9 | Semi standard non polar | 33892256 | Proanthocyanidins,3TMS,isomer #34 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 4565.2 | Standard non polar | 33892256 | Proanthocyanidins,3TMS,isomer #34 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 6893.0 | Standard polar | 33892256 | Proanthocyanidins,3TMS,isomer #44 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 5208.7 | Semi standard non polar | 33892256 | Proanthocyanidins,3TMS,isomer #44 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 4527.3 | Standard non polar | 33892256 | Proanthocyanidins,3TMS,isomer #44 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 6845.4 | Standard polar | 33892256 | Proanthocyanidins,3TMS,isomer #48 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 5205.5 | Semi standard non polar | 33892256 | Proanthocyanidins,3TMS,isomer #48 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 4549.9 | Standard non polar | 33892256 | Proanthocyanidins,3TMS,isomer #48 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 6841.8 | Standard polar | 33892256 | Proanthocyanidins,3TMS,isomer #49 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O | 5238.7 | Semi standard non polar | 33892256 | Proanthocyanidins,3TMS,isomer #49 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O | 4595.9 | Standard non polar | 33892256 | Proanthocyanidins,3TMS,isomer #49 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O | 6723.6 | Standard polar | 33892256 | Proanthocyanidins,3TMS,isomer #50 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 5229.2 | Semi standard non polar | 33892256 | Proanthocyanidins,3TMS,isomer #50 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 4608.6 | Standard non polar | 33892256 | Proanthocyanidins,3TMS,isomer #50 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 6905.6 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #12 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 5131.4 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #12 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 4456.7 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #12 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 6520.4 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #22 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 5067.5 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #22 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 4409.9 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #22 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 6462.3 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #32 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 5064.8 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #32 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 4439.6 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #32 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 6482.0 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #33 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O | 5077.4 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #33 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O | 4482.5 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #33 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O | 6408.5 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #34 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 5082.3 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #34 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 4514.9 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #34 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O[Si](C)(C)C)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 6526.5 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #47 | COC1=C(O[Si](C)(C)C)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 5152.2 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #47 | COC1=C(O[Si](C)(C)C)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 4437.6 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #47 | COC1=C(O[Si](C)(C)C)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 6456.6 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #57 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 5062.0 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #57 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 4426.6 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #57 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 6445.0 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #67 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 5069.7 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #67 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 4453.2 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #67 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 6447.7 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #68 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 5102.7 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #68 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 4493.3 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #68 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O[Si](C)(C)C | 6376.2 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #69 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C | 5090.6 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #69 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C | 4511.2 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #69 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O[Si](C)(C)C | 6492.8 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #77 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 5012.2 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #77 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 4410.3 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #77 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 6406.5 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #78 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O | 5027.6 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #78 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O | 4453.3 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #78 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O | 6341.6 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #79 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 5009.2 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #79 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 4463.3 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #79 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 6451.8 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #83 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O | 5036.6 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #83 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O | 4473.5 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #83 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O)C=C1O | 6351.8 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #84 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 5020.3 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #84 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 4495.3 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #84 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 6455.8 | Standard polar | 33892256 | Proanthocyanidins,4TMS,isomer #85 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 5035.1 | Semi standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #85 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 4535.1 | Standard non polar | 33892256 | Proanthocyanidins,4TMS,isomer #85 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O[Si](C)(C)C)C=C3)[C@@H]2O[Si](C)(C)C)C=C1O | 6381.8 | Standard polar | 33892256 | Proanthocyanidins,2TBDMS,isomer #16 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C(C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 5904.0 | Semi standard non polar | 33892256 | Proanthocyanidins,2TBDMS,isomer #16 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C(C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 4974.7 | Standard non polar | 33892256 | Proanthocyanidins,2TBDMS,isomer #16 | COC1=C(O)C=C(C2OC3=C(C[C@H]2O)C(O)=CC(O[Si](C)(C)C(C)(C)C)=C3[C@H]2C3=C(O[Si](C)(C)C(C)(C)C)C=C(O)C=C3O[C@H](C3=CC=C(O)C=C3)[C@@H]2O)C=C1O | 7221.3 | Standard polar | 33892256 |
|
---|