(-)-epicatechin (4beta→8) (-)-epicatechin - Compound Card

(-)-epicatechin (4beta→8) (-)-epicatechin

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(-)-epicatechin (4beta→8) (-)-epicatechin

Structure
Zoomed Structure
  • Family: Plantae - Rosaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Biflavonoid
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-/m1/s1
InChIKey XFZJEEAOWLFHDH-NFJBMHMQSA-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 Maytenus senegalensis Celastraceae Plantae 256095
2 Crataegus sinaica Rosaceae Plantae 298646
3 Rosa canina Rosaceae Plantae 74635

Showing of synonyms

  • 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]
  • 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]
  • Hussein G, Miyashiro H, et al. (1999). Inhibitory effects of Sudanese plant extracts on HIV-1 replication and HIV-1 protease. Phytotherapy Research,1999,13(1),31-36. [View] [PubMed]
Pubchem: 122738
Kegg Ligand: C17639
Chebi: 75632
Nmrshiftdb2: 60021299
Metabolights: MTBLC75632
CPRiL: 54587
Structure

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C4CC(c5ccccc5)Oc(c46)cccc6

Level: 3

Mol. Weight: 578.53 g/mol

Structure

SMILES: c1ccccc1C(O2)CCc(c23)cccc3C4CCOc(c45)cccc5

Level: 2

Mol. Weight: 578.53 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C3CC(c4ccccc4)Oc(c35)cccc5

Level: 2

Mol. Weight: 578.53 g/mol

Structure

SMILES: O1CCCc(c12)cccc2C3CCOc(c34)cccc4

Level: 1

Mol. Weight: 578.53 g/mol

Structure

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 578.53 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 578.53 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 578.53 g/mol

Anti-hiv

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
9.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.81
Plasma Protein Binding
80.76
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
11.83
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-1.83
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
6.21
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
-11810.99
Rat (Acute)
2.39
Rat (Chronic Oral)
4.23
Fathead Minnow
27.44
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
533.01
Hydration Free Energy
-3.17
Log(D) at pH=7.4
1.24
Log(P)
1.67
Log S
-4.35
Log(Vapor Pressure)
-12.63
Melting Point
281.57
pKa Acid
6.63
pKa Basic
7.18
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9053
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.9053
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.9013
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.9013
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8923
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8923
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8840
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.8840
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8816
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 5 0.8816
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8643
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8643
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.8568
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 3 0.8568
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8510
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8510
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8506
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8506
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8421
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8421
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8396
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.8396
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8360
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.8360
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8319
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8319
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.8315
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 4 0.8315
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8313
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 3 0.8313
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8235
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8235
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8208
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8208
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8188
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.8188
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 4 0.8155
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 4 0.8155
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8121
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.8121
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8099
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.8099
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8007
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8007
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8006
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q4WP27 Q4WP27_ASPFU Aspergillus fumigatus 3 0.8006
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7880
Peptidyl-prolyl cis-trans isomerase FKBP1A P62942 FKB1A_HUMAN Homo sapiens 3 0.7880
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7863
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7863
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7821
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7821
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7820
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.7820
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7771
Proton-gated ion channel Q7NDN8 GLIC_GLOVI Gloeobacter violaceus 3 0.7771
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7768
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.7768
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7748
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7748
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7657
Glucose-1-phosphate thymidylyltransferase Q9HU22 Q9HU22_PSEAE Pseudomonas aeruginosa 3 0.7657
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7623
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 3 0.7623
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7610
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 3 0.7610
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7594
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7594
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7551
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7551
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7477
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 3 0.7477
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7423
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7423
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7366
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7366
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7352
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7352
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7296
Lysozyme C II P11941 LYSC2_ONCMY Oncorhynchus mykiss 3 0.7296
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7267
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7267
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 4 0.7249
Chloramphenicol 3-O phosphotransferase Q56148 CPT_STRVP Streptomyces venezuelae 4 0.7249
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7230
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7230
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 4 0.7215
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 4 0.7215
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7214
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7214
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7211
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7211
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7211
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7211
Prostaglandin reductase 3 Q8N4Q0 PTGR3_HUMAN Homo sapiens 5 0.7152
Prostaglandin reductase 3 Q8N4Q0 PTGR3_HUMAN Homo sapiens 5 0.7152
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7139
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7139
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 4 0.7137
Geranylgeranyl transferase type-2 subunit alpha Q08602 PGTA_RAT Rattus norvegicus 4 0.7137
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7094
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7094
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7093
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7093
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 5 0.7026
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 5 0.7026
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7019
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7019
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7009
Genome polyprotein Q2YHF0 POLG_DEN4T Dengue virus type 4 3 0.7009

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