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Procyanidin B6
- Family: Plantae - Rosaceae
- Kingdom: Plantae
- Class: Proanthocyanidin
| Canonical Smiles | Oc1cc(O)c2c(c1)O[C@@H]([C@H]([C@@H]2c1c(O)cc2c(c1O)C[C@@H]([C@H](O2)c1ccc(c(c1)O)O)O)O)c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C30H26O12/c31-13-7-19(36)24-23(8-13)42-30(12-2-4-16(33)18(35)6-12)28(40)26(24)25-20(37)10-22-14(27(25)39)9-21(38)29(41-22)11-1-3-15(32)17(34)5-11/h1-8,10,21,26,28-40H,9H2/t21-,26-,28-,29+,30+/m0/s1 |
| InChIKey | GMISZFQPFDAPGI-ZBRHZRBFSA-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 | Rosa canina | Rosaceae | Plantae | 74635 |
Showing of synonyms
Procyanidin B6
12798-58-2
Procyanidin dimer B6
CHEBI:75619
Catechin(4a->6)catechin
Catechin-(4alpha->6)-catechin
C-(4,6)-C
(2r,2'r,3s,3's,4r)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2h,2'h-4,6'-bichromene-3,3',5,5',7,7'-hexol
Procyanidol B6
SZ77QV8UB3
(2R,3S)-2-(3,4-dihydroxyphenyl)-6-[(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
(2R,2R,3S,3S,4R)-2,2-Bis(3,4-dihydroxyphenyl)-3,3,4,4-tetrahydro(4,6-bi-2H-1-benzopyran)-3,3,5,5,7,7-hexol
(4,6-Bi-2H-1-benzopyran)-3,3,5,5,7,7-hexol, 2,2-bis(3,4-dihydroxyphenyl)-3,3,4,4-tetrahydro-, (2R,2R,3S,3S,4R)-
UNII-SZ77QV8UB3
CHEMBL502984
SCHEMBL13999378
DTXSID001028815
Catechin-(4.alpha.-->6)catechin
HY-N12984
(+)-Catechin-(4alpha-6)-(+)-catechin
CS-1099836
(+)-CATECHIN-(4.ALPHA.-6)-(+)-CATECHIN
Q7247558
(2R,3S,4R)-2-(3,4-dihydroxyphenyl)-4-[(2R,3S)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-chroman-6-yl]chromane-3,5,7-triol
(4,6-BI-2H-1-BENZOPYRAN)-3,3,5,5,7,7-HEXOL, 2,2-BIS(3,4-DIHYDROXYPHENYL)-3,3,4,4-TETRAHYDRO-, (2R-(2.ALPHA.,3.BETA.,4.ALPHA.(2R*,3S*)))-
(4,6-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(2R*,3S*)))-
- 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]
Pubchem:
474540
Cas:
12798-58-2
Zinc:
ZINC000042806801
Chebi:
75619
Nmrshiftdb2:
60146453
Metabolights:
MTBLC75619
Chembl:
CHEMBL502984
No compound-protein relationship available.
SMILES: c1cccc(c12)OC(c3ccccc3)CC2c(c4)ccc(c45)OC(CC5)c6ccccc6
Level: 3
Mol. Weight: 578.53 g/mol
SMILES: c1cccc(c12)OCCC2c(c3)ccc(c34)OC(CC4)c5ccccc5
Level: 2
Mol. Weight: 578.53 g/mol
SMILES: c1cccc(c12)OC(c3ccccc3)CC2c(c4)ccc(c45)OCCC5
Level: 2
Mol. Weight: 578.53 g/mol
SMILES: c1cccc(c12)OCCC2c(c3)ccc(c34)OCCC4
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)
- -6.64
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.65
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 9.09
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.79
- Plasma Protein Binding
- 82.66
- 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
- 11.71
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.53
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.09
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 6.3
- 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
- -11868.81
- Rat (Acute)
- 2.4
- Rat (Chronic Oral)
- 4.27
- Fathead Minnow
- 27.5
- 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
- 524.23
- Hydration Free Energy
- -3.17
- Log(D) at pH=7.4
- 1.23
- Log(P)
- 2.29
- Log S
- -4.18
- Log(Vapor Pressure)
- -12.82
- Melting Point
- 302.94
- pKa Acid
- 6.47
- pKa Basic
- 7.54
| 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 | 0.9283 |
| cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A | Q9QYJ6 | PDE10_RAT | Rattus norvegicus | 4 | 0.8985 |
| Flavoredoxin | Q72HI0 | Q72HI0_THET2 | Thermus thermophilus | 3 | 0.8712 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8711 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.8595 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.8536 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.8478 |
| Heat shock protein 75 kDa, mitochondrial | Q12931 | TRAP1_HUMAN | Homo sapiens | 4 | 0.8468 |
| Mycocyclosin synthase | P9WPP7 | CP121_MYCTU | Mycobacterium tuberculosis | 3 | 0.8429 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8303 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8286 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8233 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8171 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 4 | 0.8164 |
| D-aminoacyl-tRNA deacylase | Q8IIS0 | DTD_PLAF7 | Plasmodium falciparum | 3 | 0.8158 |
| Tetracycline repressor protein class D | P0ACT4 | TETR4_ECOLX | Escherichia coli | 4 | 0.8122 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.8114 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8109 |
| Geranylgeranyl transferase type-2 subunit alpha | Q08602 | PGTA_RAT | Rattus norvegicus | 3 | 0.8108 |
| Proto-oncogene tyrosine-protein kinase Src | P00523 | SRC_CHICK | Gallus gallus | 3 | 0.8092 |
| HTH-type transcriptional regulator TtgR | Q9AIU0 | TTGR_PSEPT | Pseudomonas putida | 3 | 0.8057 |
| Beta-glucosidase 1A | Q25BW5 | BGL1A_PHACH | Phanerodontia chrysosporium | 3 | 0.8038 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7961 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 4 | 0.7900 |
| Thymidine phosphorylase | Q7CP66 | TYPH_SALTY | Salmonella typhimurium | 3 | 0.7847 |
| Endothiapepsin | P11838 | CARP_CRYPA | Cryphonectria parasitica | 4 | 0.7846 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.7757 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7754 |
| Lactotransferrin | P24627 | TRFL_BOVIN | Bos taurus | 3 | 0.7725 |
| Bromodomain-containing protein 4 | O60885 | BRD4_HUMAN | Homo sapiens | 3 | 0.7703 |
| Endoplasmin | P41148 | ENPL_CANLF | Canis lupus familiaris | 4 | 0.7686 |
| Polyribonucleotide nucleotidyltransferase | A7ZS61 | PNP_ECO24 | Escherichia coli O139:H28 | 4 | 0.7633 |
| Ras-related protein Ral-B | P11234 | RALB_HUMAN | Homo sapiens | 3 | 0.7620 |
| Ribonuclease J | H9CZL7 | H9CZL7_DEIRD | Deinococcus radiodurans | 3 | 0.7581 |
| Leucoanthocyanidin dioxygenase | Q96323 | LDOX_ARATH | Arabidopsis thaliana | 4 | 0.7542 |
| Acetylcholinesterase | P04058 | ACES_TETCF | Tetronarce californica | 3 | 0.7439 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 3 | 0.7437 |
| 1,4-alpha-glucan branching enzyme GlgB | A7ZSW5 | GLGB_ECO24 | Escherichia coli O139:H28 | 3 | 0.7435 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7434 |
| Serine/threonine-protein kinase 24 | Q9Y6E0 | STK24_HUMAN | Homo sapiens | 3 | 0.7422 |
| Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha | Q04631 | FNTA_RAT | Rattus norvegicus | 3 | 0.7400 |
| Serine/threonine-protein kinase Chk1 | O14757 | CHK1_HUMAN | Homo sapiens | 3 | 0.7386 |
| Maltokinase | A1TH50 | MAK_MYCVP | Mycolicibacterium vanbaalenii | 3 | 0.7380 |
| Tau-tubulin kinase 1 | Q5TCY1 | TTBK1_HUMAN | Homo sapiens | 4 | 0.7370 |
| Nitric oxide synthase, inducible | P29477 | NOS2_MOUSE | Mus musculus | 3 | 0.7357 |
| cGMP-dependent 3',5'-cyclic phosphodiesterase | O00408 | PDE2A_HUMAN | Homo sapiens | 3 | 0.7318 |
| Major strawberry allergen Fra a 1-3 | D0E0C7 | FRA13_FRAAN | Fragaria ananassa | 5 | 0.7317 |
| Gag-Pol polyprotein | P03367 | POL_HV1BR | Human immunodeficiency virus type 1 group M subtype B | 3 | 0.7280 |
| Bifunctional epoxide hydrolase 2 | P34913 | HYES_HUMAN | Homo sapiens | 3 | 0.7222 |
| Maltose/maltodextrin-binding periplasmic protein | P0AEX9 | MALE_ECOLI | Escherichia coli | 3 | 0.7191 |
| Prolyl tripeptidyl peptidase | Q7MUW6 | PTP_PORGI | Porphyromonas gingivalis | 3 | 0.7187 |
| Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic | Q43088 | RBCMT_PEA | Pisum sativum | 3 | 0.7178 |
| Tryptophan--tRNA ligase | Q9PIB4 | SYW_CAMJE | Campylobacter jejuni subsp. jejuni serotype O:2 | 4 | 0.7167 |
| Beta-lactoglobulin | P02754 | LACB_BOVIN | Bos taurus | 3 | 0.7145 |
| Aldo-keto reductase family 1 member D1 | P51857 | AK1D1_HUMAN | Homo sapiens | 3 | 0.7047 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 4 | 0.7031 |
| Mitochondrial poly(A) polymerase | F1NBW0 | F1NBW0_CHICK | Gallus gallus | 2 | 0.7022 |
| Heat shock protein HSP 90-alpha | P07900 | HS90A_HUMAN | Homo sapiens | 3 | 0.7017 |
| Tyrosine-protein kinase ABL1 | P00519 | ABL1_HUMAN | Homo sapiens | 3 | 0.7007 |