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Proanthocyanidin A-2
- Family: Plantae - Rubiaceae
- Kingdom: Plantae
-
Class: Flavonoid
- Subclass: Proanthocyanidin
| Canonical Smiles | Oc1cc(O)c2c(c1)O[C@@]1([C@@H]([C@H]2c2c(O1)cc(c1c2O[C@@H]([C@@H](C1)O)c1ccc(c(c1)O)O)O)O)c1ccc(c(c1)O)O |
|---|---|
| InChI | InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27-,29-,30+/m1/s1 |
| InChIKey | NSEWTSAADLNHNH-LSBOWGMISA-N |
| Formula | C30H24O12 |
| HBA | 12 |
| HBD | 9 |
| MW | 576.51 |
| Rotatable Bonds | 2 |
| TPSA | 209.76 |
| LogP | 2.79 |
| Number Rings | 7 |
| Number Aromatic Rings | 4 |
| Heavy Atom Count | 42 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.2 |
| Exact Mass | 576.13 |
| Number of Lipinski Rule Violations | 3 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Crataegus sinaica | Rosaceae | Plantae | 298646 |
| 2 | Psorospermum densipunctatum | Hypericaceae | Plantae | 999533 |
| 3 | Tamarix articulata | Tamaricaceae | Plantae | 189786 |
| 4 | Ixora coccinea | Rubiaceae | Plantae | 43503 |
Showing of synonyms
Proanthocyanidin A-2
Procyanidin A2
UQN6668Q4R
LITCHIDERM LS-9704 COMPONENT
8,14-METHANO-2H,14H-1-BENZOPYRANO(7,8-D)(1,3)BENZODIOXOCIN-3,5,11,13,15-PENTOL, 2,8-BIS(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-, (2R,3R,8S,14R,15R)-
8,14-Methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R,8S,14R,15R)-
(+)-EPICATECHIN-(4beta-8,2beta-O-7)-EPICATECHIN
Proanthocyanidin A2
41743-41-3
Procyanidol A2
Procyanidin dimer A2
CHEBI:28472
Epicatechin-(2beta->7,4beta->8)-epicatechin
CHEMBL286933
(2r,3r,8s,14r,15r)-2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-2h,14h-8,14-methanochromeno[7,8-d][1,3]benzodioxocine-3,5,11,13,15-pentol
(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.02,11.03,8.015,20]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
(+)-Proanthocyanidin A2
Dimeric catechin
(+)-Epicatechin-(4.beta.-8,2.beta.-O-7)-epicatechin
Bis(3,4-dihydroxyphenyl)[?]pentol
(2R,3R,8S,14R,15R)-2,8-Bis(3,4-dihydroxyphenyl)-3,4-dihydro-2H,14H-8,14-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-3,5,11,13,15-pentaol
Procyanidoepicatechin
Procyanidin A2 (Standard)
UNII-UQN6668Q4R
SCHEMBL981582
HY-N2343R
DTXSID00904175
Procyanidin A2, analytical standard
BDBM50478905
EC-(4b,8)(2b,7)-EC
AKOS037514797
FP75067
2,14-Bis(3,4-dihydroxyphenyl)-3,4-dihydro-8,14-methano-2H,8H,14H-1-benzopyrano(8,7-c)(1,5)benzodioxocin-3,5,9,11,15-pentol
AC-35008
DA-77078
Epicatechin-(2b->7,4b->8)-epicatechin
MS-30365
Q7247550
Epicatechin-(4.beta.-->8,2.beta.-->O-->7)epicatechin
(1R,5R,6R,13S,21R)-5,13-bis(3,4-dihydroxyphenyl)-4,12,14-trioxapentacyclo[11.7.1.0(2),(1)(1).0(3),?.0(1)?,(2)?]henicosa-2(11),3(8),9,15,17,19-hexaene-6,9,17,19,21-pentol
8,14-Methano-2H,14H-1,7,9-trioxabenzo[6,7]cycloocta[1,2-a]naphthalene-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R,8S,14R,15R)-
8,14-Methano-2H,14H-1-benzopyrano[7,8-d][1,3]benzodioxocin-3,5,11,13,15-pentol, 2,8-bis(3,4-dihydroxyphenyl)-3,4-dihydro-, [2R-(2.alpha,3.alpha.,8.beta.,14.beta.,15R*)]-
8,14-Methano-2H,8H,14H-1-benzopyrano(8,7-c)(1,5)benzodioxocin-3,5,9,11,15-pentol, 2,14-bis(3,4-dihydroxyphenyl)-3,4-dihydro-
Proanthocyanidin A2\, Procyanidol A2\, Procyanidoepicatechin\, Epicatechin-(2beta->7\,4beta->8)-epicatechin
- Shahat AA, Ismail SI, et al. (1998). Anti-HIV activity of flavonoids and proanthocyanidins from Crataegus sinaica. Phytomedicine,1998,5(2),133-136. [View] [PubMed]
- Tanemossu S, Franke K, et al. (2015). Chemical constituents of Psorospermum densipunctatum (Hypericaceae). Biochemical Systematics and Ecology, 2015, 59, 174-176. [View]
- Shaalan Y.M, Handoussa H, et al. (2018). Destabilizing the interplay between miR-1275 and IGF2BPs by Tamarix articulata and quercetin in hepatocellular carcinoma. Nat Prod Res,2018,32(18),2217-2220. [View] [PubMed]
- Idowu TO, Ogundaini AO, et al. (2010). Doubly linked, A-type proanthocyanidin trimer and other constituents of Ixora coccinea leaves and their antioxidant and antibacterial properties. Phytochemistry,2010,71(17–18),2092-2098. [View]
Pubchem:
124025
Cas:
41743-41-3
Gnps:
CCMSLIB00006424586
Zinc:
ZINC000004098619
Kegg Ligand:
C10237
Chebi:
28472
Metabolights:
MTBLC28472
Chembl:
CHEMBL286933
Bindingdb:
50478905
CPRiL:
78522
SMILES: c1ccccc1C23CC(c4c(O3)cccc4)c5c6c(ccc5O2)CCC(O6)c7ccccc7
Level: 2
Mol. Weight: 576.51 g/mol
SMILES: c1ccccc1C(O2)CCc(c2c34)ccc3OC5CC4c6c(O5)cccc6
Level: 1
Mol. Weight: 576.51 g/mol
SMILES: O1c2ccc(CCCO3)c3c2C(c4c(O5)cccc4)CC15c6ccccc6
Level: 1
Mol. Weight: 576.51 g/mol
SMILES: O1CCCc(c1c23)ccc2OC4CC3c5c(O4)cccc5
Level: 0
Mol. Weight: 576.51 g/mol
SMILES: c1ccccc1
Level: 0
Mol. Weight: 576.51 g/mol
Anti-hiv
Antibacterial
Absorption
- Caco-2 (logPapp)
- -6.51
- Human Oral Bioavailability 20%
- Non-Bioavailable
- Human Intestinal Absorption
- Non-Absorbed
- Madin-Darby Canine Kidney
- -5.26
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Inhibitor
- P-Glycoprotein Substrate
- Substrate
- Skin Permeability
- 10.71
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 1.06
- Plasma Protein Binding
- 82.58
- 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
- 11.72
- Organic Cation Transporter 2
- Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.17
- Biodegradation
- Safe
- Carcinogenesis
- Safe
- Crustacean
- Toxic
- Liver Injury I (DILI)
- Toxic
- Eye Corrosion
- Safe
- Eye Irritation
- Toxic
- Maximum Tolerated Dose
- 1.42
- Liver Injury II
- Toxic
- hERG Blockers
- Safe
- Daphnia Maga
- 5.98
- 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
- -15163.83
- Rat (Acute)
- 2.42
- Rat (Chronic Oral)
- 3.81
- Fathead Minnow
- 36.38
- 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
- 488.48
- Hydration Free Energy
- -3.17
- Log(D) at pH=7.4
- 1.6
- Log(P)
- 1.85
- Log S
- -4.34
- Log(Vapor Pressure)
- -15.56
- Melting Point
- 305.52
- pKa Acid
- 5.63
- pKa Basic
- 7.89
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.9283 |
| Homoserine dehydrogenase | P31116 | DHOM_YEAST | Saccharomyces cerevisiae | 4 | 0.9283 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8973 |
| Nuclear receptor subfamily 4immunitygroup A member 1 | P22736 | NR4A1_HUMAN | Homo sapiens | 3 | 0.8973 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8661 |
| Cyclin-dependent kinase 2 | P24941 | CDK2_HUMAN | Homo sapiens | 3 | 0.8661 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8577 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.8577 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8403 |
| Carbonic anhydrase 2 | P00918 | CAH2_HUMAN | Homo sapiens | 3 | 0.8403 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8394 |
| Histone deacetylase 4 | P56524 | HDAC4_HUMAN | Homo sapiens | 3 | 0.8394 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8324 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8324 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8315 |
| Uracil phosphoribosyltransferase | Q26998 | UPP_TOXGO | Toxoplasma gondii | 3 | 0.8315 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8254 |
| Tyrosine-protein kinase JAK2 | O60674 | JAK2_HUMAN | Homo sapiens | 3 | 0.8254 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8159 |
| NAD(P)H-hydrate epimerase | Q8K4Z3 | NNRE_MOUSE | Mus musculus | 3 | 0.8159 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8077 |
| Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase | Q05603 | COBT_SALTY | Salmonella typhimurium | 3 | 0.8077 |
| Multidrug-efflux transporter 1 regulator | P39075 | BMRR_BACSU | Bacillus subtilis | 3 | 0.7924 |
| Multidrug-efflux transporter 1 regulator | P39075 | BMRR_BACSU | Bacillus subtilis | 3 | 0.7924 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7706 |
| Chitinase A | Q9AMP1 | Q9AMP1_VIBHA | Vibrio harveyi | 3 | 0.7706 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7701 |
| Nitric oxide synthase oxygenase | O34453 | NOSO_BACSU | Bacillus subtilis | 4 | 0.7701 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7644 |
| 3',5'-cyclic-AMP phosphodiesterase 4D | Q08499 | PDE4D_HUMAN | Homo sapiens | 3 | 0.7644 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7552 |
| Basic phospholipase A2 VRV-PL-VIIIa | P59071 | PA2B8_DABRR | Daboia russelii | 2 | 0.7552 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.7443 |
| HTH-type transcriptional regulator QacR | P0A0N3 | QACR_STAAM | Staphylococcus aureus | 3 | 0.7443 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7429 |
| Type IV / VI secretion system DotU domain-containing protein | Q9KN50 | Q9KN50_VIBCH | Vibrio cholerae serotype O1 | 3 | 0.7429 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7181 |
| Lactoylglutathione lyase | Q9CPU0 | LGUL_MOUSE | Mus musculus | 2 | 0.7181 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7138 |
| rRNA N-glycosylase | D9J2T9 | D9J2T9_MOMBA | Momordica balsamina | 3 | 0.7138 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7130 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7130 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7092 |
| High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A | O76083 | PDE9A_HUMAN | Homo sapiens | 3 | 0.7092 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 4 | 0.7012 |
| Phenylalanine-4-hydroxylase | P00439 | PH4H_HUMAN | Homo sapiens | 4 | 0.7012 |