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Procyanidin B3
- Family: Plantae - Rosaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Proanthocyanidin
| Canonical Smiles | Oc1cc(O)c2c(c1)O[C@@H]([C@H]([C@@H]2c1c(O)cc(c2c1O[C@@H]([C@H](C2)O)c1ccc(c(c1)O)O)O)O)c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26-,27-,28+,29+/m0/s1 |
| InChIKey | XFZJEEAOWLFHDH-AVFWISQGSA-N |
| Formula | C30H26O12 |
| HBA | 12 |
| HBD | 10 |
| MW | 578.53 |
| Rotatable Bonds | 3 |
| TPSA | 220.76 |
| LogP | 3.0 |
| Number Rings | 6 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 42 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.2 |
| Exact Mass | 578.14 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Gilbertiodendron dewevrei | Caesalpinioideae | Plantae | 162777 |
| 2 | Rosa canina | Rosaceae | Plantae | 74635 |
Showing of synonyms
Procyanidin B3
23567-23-9
Proanthocyanidin B3
Procyanidin B-3
CHEBI:75630
2TC1A0KEAQ
Catechin(4a->8)catechin
2,3-trans-proanthocyanidin
Catechin-(4alpha->8)-catechin
PROCYANIDOL B3S
C-(4a,8)-C
(2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
[4,8'-Bi-2H-1-benzopyran]-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R,2'R,3S,3'S,4S)-
(-)-PROCYANIDIN B3
DTXSID60178193
(4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R,2'R,3S,3'S,4S)-
(2R-(2alpha,3beta,4alpha(2'R*,3'S*)))-2,2'-Bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-(4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol
(4,8'-Bi-2H-1-benzopyran)-3,3',5,5',7,7'-hexol, 2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-, (2R-(2alpha,3beta,4alpha(2'R*,3'S*)))-
(2R,2'R,3S,3'S,4S)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5,5',7,7'-hexol
(2R,3S)-2-(3,4-dihydroxyphenyl)-8-((2R,3S,4S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl)-3,4-dihydro-2H-chromene-3,5,7-triol
Afzelechin-(4alpha-
Proanthocyanidin B-3
Catechin 4-8 catechin
Catechin 4alpha-8 catechin
DTXCID90100684
CHEMBL501490
(2R,2'R,3S,3'S,4S)-2,2'-Bis(3,4-dihydroxyphenyl)-[4,8'-bichromane]-3,3',5,5',7,7'-hexaol
UNII-2TC1A0KEAQ
PROCYANIDINB3
Procyanidin B3 (Standard)
Catechin-(4a?8)-catechin
Catechin-(4?->8)-catechin
SCHEMBL677697
HY-N2345R
XFZJEEAOWLFHDH-AVFWISQGSA-N
Catechin-(4.alpha.-->8)catechin
HY-N2345
BDBM50447858
LMPK12030003
MSK169527
AKOS016009332
FP65542
AC-35059
DA-66881
MS-30396
1ST169527
CS-0021307
NS00094744
Q7247553
(2R,3S,4S)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-8-yl]chromane-3,5,7-triol
- Fetni S, Bertella N, et al. (2020). Composition and biological activity of the Algerian plant Rosa canina L by HPLC-UV-MS. Arabian Journal of Chemistry, 2020, 13(1), 1105-1119. [View]
- Stephanie DM, Stéphane FFY, et al. (2022). Dewerin and gilbertionol two new secondary metabolites from the stem bark of Gilbertiodendron dewevrei (De Wild) J. Leonard.. Natural product research,2022, 36(1), 214-222. [View] [PubMed]
Pubchem:
146798
Cas:
23567-23-9
Gnps:
CCMSLIB00000209692
Zinc:
ZINC000042804873
Chebi:
75630
Nmrshiftdb2:
60021295
Metabolights:
MTBLC75630
Chembl:
CHEMBL501490
Comptox:
DTXSID60178193
Bindingdb:
50447858
CPRiL:
97807
SMILES: c1ccccc1C(O2)CCc(c23)cccc3C4CC(c5ccccc5)Oc(c46)cccc6
Level: 3
Mol. Weight: 578.53 g/mol
SMILES: c1ccccc1C(O2)CCc(c23)cccc3C4CCOc(c45)cccc5
Level: 2
Mol. Weight: 578.53 g/mol
SMILES: O1CCCc(c12)cccc2C3CC(c4ccccc4)Oc(c35)cccc5
Level: 2
Mol. Weight: 578.53 g/mol
SMILES: O1CCCc(c12)cccc2C3CCOc(c34)cccc4
Level: 1
Mol. Weight: 578.53 g/mol
SMILES: c1cccc(c12)OC(CC2)c3ccccc3
Level: 1
Mol. Weight: 578.53 g/mol
SMILES: C1CCOc(c12)cccc2
Level: 0
Mol. Weight: 578.53 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 578.53 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -6.62
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.63
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 9.1
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.81
- Plasma Protein Binding
- 80.42
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 11.84
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.57
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.13
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.22
- Micronucleos
- Toxic
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -11810.77
- Rat (Acute)
- 2.39
- Rat (Chronic Oral)
- 4.22
- Fathead Minnow
- 27.48
- Respiratory Disease
- Toxic
- Skin Sensitisation
- Safe
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 531.84
- Hydration Free Energy
- -3.17
- Log(D) at pH=7.4
- 1.27
- Log(P)
- 1.61
- Log S
- -4.34
- Log(Vapor Pressure)
- -12.62
- Melting Point
- 280.38
- pKa Acid
- 6.64
- pKa Basic
- 7.23
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8961 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8918 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q4WP27 | Q4WP27_ASPFU | Aspergillus fumigatus | 3 | 0.8615 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.8521 |
| Cathepsin S | P25774 | CATS_HUMAN | Homo sapiens | 3 | 0.8434 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.8369 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8299 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8289 |
| Geranylgeranyl transferase type-2 subunit alpha | Q08602 | PGTA_RAT | Rattus norvegicus | 3 | 0.8281 |
| Ribosomal small subunit pseudouridine synthase A | P0AA43 | RSUA_ECOLI | Escherichia coli | 3 | 0.8147 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.8065 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7939 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7886 |
| Insulin-degrading enzyme | P14735 | IDE_HUMAN | Homo sapiens | 3 | 0.7820 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7640 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.7607 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7557 |
| Disks large homolog 1 | Q12959 | DLG1_HUMAN | Homo sapiens | 3 | 0.7538 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.7523 |
| Gag-Pol polyprotein | P12497 | POL_HV1N5 | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7464 |
| Purine nucleoside phosphorylase | P00491 | PNPH_HUMAN | Homo sapiens | 3 | 0.7422 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7384 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.7363 |
| 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase | Q3JRA0 | ISPF_BURP1 | Burkholderia pseudomallei | 4 | 0.7349 |
| Beta-secretase 1 | P56817 | BACE1_HUMAN | Homo sapiens | 3 | 0.7342 |
| S-adenosylmethionine decarboxylase proenzyme | P17707 | DCAM_HUMAN | Homo sapiens | 3 | 0.7162 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7124 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | P49354 | FNTA_HUMAN | Homo sapiens | 3 | 0.7103 |
| Epidermal growth factor receptor | P00533 | EGFR_HUMAN | Homo sapiens | 3 | 0.7096 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7062 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7055 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7034 |
| Acetolactate synthase, chloroplastic | P17597 | ILVB_ARATH | Arabidopsis thaliana | 2 | 0.7017 |
| Riboflavin biosynthesis protein | Q9WZW1 | Q9WZW1_THEMA | Thermotoga maritima | 4 | 0.7010 |