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Epicatechin (4beta→8) epigallocatechin

Family: Plantae - Celastraceae
Kingdom: Plantae
Class: Flavonoid
- Subclass: Biflavonoid

Canonical Smiles	Oc1cc(O)c2c(c1)O[C@@H]([C@@H](C2c1c(O)cc(c2c1O[C@@H]([C@@H](C2)O)c1cc(O)c(c(c1)O)O)O)O)c1ccc(c(c1)O)O
InChI	InChI=1S/C30H26O13/c31-12-6-17(35)23-22(7-12)42-29(10-1-2-14(32)16(34)3-10)27(41)25(23)24-18(36)9-15(33)13-8-21(39)28(43-30(13)24)11-4-19(37)26(40)20(38)5-11/h1-7,9,21,25,27-29,31-41H,8H2/t21-,25?,27-,28-,29-/m1/s1
InChIKey	YJMNEZANCYQLJR-RXRZWOQSSA-N
Formula	C₃₀H₂₆O₁₃
HBA	13
HBD	11
MW	594.53
Rotatable Bonds	3
TPSA	240.99
LogP	2.7
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	43
Formal Charge	0
Fraction CSP3	0.2
Exact Mass	594.14
Number of Lipinski Rule Violations	3

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Maytenus senegalensis	Celastraceae	Plantae	256095

Showing of synonyms

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: 476783

Nmrshiftdb2: 70023439

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 594.53 g/mol

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

Level: 2

Mol. Weight: 594.53 g/mol

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

Level: 2

Mol. Weight: 594.53 g/mol

SMILES: O1CCCc(c12)cccc2C3CCOc(c34)cccc4

Level: 1

Mol. Weight: 594.53 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 594.53 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 594.53 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 594.53 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.65
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.82
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 12.61

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.7
Plasma Protein Binding: 71.98
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: 12.24
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -2.6
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.05
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: -17246.49
Rat (Acute): 2.42
Rat (Chronic Oral): 4.41
Fathead Minnow: 38.28
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: 507.28
Hydration Free Energy: -3.17
Log(D) at pH=7.4: 0.73
Log(P): 1.27
Log S: -4.23
Log(Vapor Pressure): -16.41
Melting Point: 283.0
pKa Acid: 6.1
pKa Basic: 8.52

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	0.9001
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	3	0.9001
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8979
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8979
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8813
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.8813
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8804
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	5	0.8804
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8776
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8776
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.8594
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.8594
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8591
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	3	0.8591
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8537
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8537
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8482
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8482
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8481
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.8481
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8458
Flavoredoxin	Q72HI0	Q72HI0_THET2	Thermus thermophilus	3	0.8458
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8388
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.8388
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8369
Riboflavin synthase	P0AFU8	RISA_ECOLI	Escherichia coli	4	0.8369
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8336
WxcM-like protein	Q12KT8	Q12KT8_SHEDO	Shewanella denitrificans	4	0.8336
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8293
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.8293
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8248
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.8248
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.8193
Thymidylate synthase	P00469	TYSY_LACCA	Lacticaseibacillus casei	4	0.8193
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8176
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8176
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	4	0.8144
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	4	0.8144
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8129
rRNA N-glycosylase	D9J2T9	D9J2T9_MOMBA	Momordica balsamina	3	0.8129
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8103
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.8103
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8041
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.8041
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7993
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7993
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7987
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	3	0.7987
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7919
Peptidyl-prolyl cis-trans isomerase FKBP1A	P62942	FKB1A_HUMAN	Homo sapiens	3	0.7919
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7782
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7782
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7683
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7683
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7672
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7672
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7655
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7655
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7612
Glucose-1-phosphate thymidylyltransferase	Q9HU22	Q9HU22_PSEAE	Pseudomonas aeruginosa	3	0.7612
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.7515
Alpha amylase	B8CZ54	B8CZ54_HALOH	Halothermothrix orenii	3	0.7515
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7416
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7416
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7365
Serpin domain-containing protein	H0ZQY2	H0ZQY2_TAEGU	Taeniopygia guttata	3	0.7365
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7255
Lethal(3)malignant brain tumor-like protein 1	Q9Y468	LMBL1_HUMAN	Homo sapiens	3	0.7255
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7249
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	2	0.7249
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7247
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7247
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7216
Lactotransferrin	P24627	TRFL_BOVIN	Bos taurus	3	0.7216
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7208
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7208
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7203
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.7203
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7167
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	4	0.7167
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	4	0.7147
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	4	0.7147
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7144
Serine/threonine-protein kinase Chk1	O14757	CHK1_HUMAN	Homo sapiens	3	0.7144
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7131
UDP-galactopyranose mutase	Q48485	GLF1_KLEPN	Klebsiella pneumoniae	3	0.7131
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.7123
HTH-type transcriptional regulator TtgR	Q9AIU0	TTGR_PSEPT	Pseudomonas putida	4	0.7123
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7093
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.7093
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7068
L-lactate dehydrogenase A chain	P04642	LDHA_RAT	Rattus norvegicus	3	0.7068
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7054
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.7054
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7025
Nitric oxide synthase oxygenase	O34453	NOSO_BACSU	Bacillus subtilis	4	0.7025
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	5	0.7021
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	5	0.7021
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7007
Genome polyprotein	Q2YHF0	POLG_DEN4T	Dengue virus type 4	3	0.7007
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7002
Tubulin alpha-1B chain	P81947	TBA1B_BOVIN	Bos taurus	3	0.7002

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