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

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

Canonical Smiles	COc1c(O)cc(cc1O)[C@H]1Oc2c(C[C@H]1O)c(O)cc(c2C1[C@@H](O)[C@H](Oc2c1c(O)cc(c2)O)c1ccc(c(c1)O)O)O
InChI	InChI=1S/C31H28O13/c1-42-31-20(38)5-12(6-21(31)39)28-22(40)9-14-16(34)10-19(37)25(30(14)44-28)26-24-18(36)7-13(32)8-23(24)43-29(27(26)41)11-2-3-15(33)17(35)4-11/h2-8,10,22,26-29,32-41H,9H2,1H3/t22-,26?,27-,28-,29-/m1/s1
InChIKey	ADKHKBZKHGJXDZ-ATEOAPGCSA-N
Formula	C₃₁H₂₈O₁₃
HBA	13
HBD	10
MW	608.55
Rotatable Bonds	4
TPSA	229.99
LogP	3.0
Number Rings	6
Number Aromatic Rings	4
Heavy Atom Count	44
Formal Charge	0
Fraction CSP3	0.23
Exact Mass	608.15
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: 476784

Nmrshiftdb2: 70023441

No compound-protein relationship available.

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

Level: 3

Mol. Weight: 608.55 g/mol

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

Level: 2

Mol. Weight: 608.55 g/mol

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

Level: 2

Mol. Weight: 608.55 g/mol

SMILES: O1CCCc(c12)cccc2C3CCOc(c34)cccc4

Level: 1

Mol. Weight: 608.55 g/mol

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 608.55 g/mol

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 608.55 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 608.55 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.49
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Non-Absorbed
Madin-Darby Canine Kidney: -5.600
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Inhibitor
P-Glycoprotein Substrate: Substrate
Skin Permeability: 18.52

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.760
Plasma Protein Binding: 67.96
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: 11.620
Organic Cation Transporter 2: Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Toxic
Bioconcentration Factor: -1.380
Biodegradation: Safe
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Toxic
Eye Corrosion: Safe
Eye Irritation: Toxic
Maximum Tolerated Dose: 1.210
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 6.120
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: -28525.810
Rat (Acute): 2.410
Rat (Chronic Oral): 4.530
Fathead Minnow: 54.200
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: 436.390
Hydration Free Energy: -3.160
Log(D) at pH=7.4: 1.800
Log(P): 1.52
Log S: -5.54
Log(Vapor Pressure): -20.26
Melting Point: 258.51
pKa Acid: 6.8
pKa Basic: 6.28

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	0.9140
Histone deacetylase 4	P56524	HDAC4_HUMAN	Homo sapiens	3	0.9140
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8693
Ribosomal small subunit pseudouridine synthase A	P0AA43	RSUA_ECOLI	Escherichia coli	3	0.8693
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8688
Nuclear receptor subfamily 4immunitygroup A member 1	P22736	NR4A1_HUMAN	Homo sapiens	3	0.8688
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8561
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	3	0.8561
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8526
Multidrug-efflux transporter 1 regulator	P39075	BMRR_BACSU	Bacillus subtilis	3	0.8526
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.8526
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	4	0.8526
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8389
NADPH-dependent oxidoreductase 2-alkenal reductase	Q39172	AER_ARATH	Arabidopsis thaliana	3	0.8389
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8340
Homoserine dehydrogenase	P31116	DHOM_YEAST	Saccharomyces cerevisiae	4	0.8340
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	4	0.8047
Phenylalanine-4-hydroxylase	P00439	PH4H_HUMAN	Homo sapiens	4	0.8047
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8012
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	3	0.8012
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8010
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.8010
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7978
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7978
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7934
Acetylcholinesterase	P21836	ACES_MOUSE	Mus musculus	3	0.7934
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7903
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7903
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7860
NAD(P)H-hydrate epimerase	Q8K4Z3	NNRE_MOUSE	Mus musculus	3	0.7860
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7816
Epidermal growth factor receptor	P00533	EGFR_HUMAN	Homo sapiens	3	0.7816
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7711
Disks large homolog 1	Q12959	DLG1_HUMAN	Homo sapiens	3	0.7711
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7656
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q04631	FNTA_RAT	Rattus norvegicus	3	0.7656
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7620
Prothrombin	P00734	THRB_HUMAN	Homo sapiens	3	0.7620
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7601
Aldo-keto reductase family 1 member D1	P51857	AK1D1_HUMAN	Homo sapiens	2	0.7601
Diamine oxidase [copper-containing]	P19801	AOC1_HUMAN	Homo sapiens	3	0.7580
Diamine oxidase [copper-containing]	P19801	AOC1_HUMAN	Homo sapiens	3	0.7580
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7529
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7529
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7526
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7526
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7490
Tyrosine-protein kinase JAK2	O60674	JAK2_HUMAN	Homo sapiens	3	0.7490
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7462
Nitric oxide synthase, inducible	P29477	NOS2_MOUSE	Mus musculus	4	0.7462
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.7454
Geranylgeranyl transferase type-2 subunit alpha	Q08602	PGTA_RAT	Rattus norvegicus	3	0.7454
Albumin	P02768	ALBU_HUMAN	Homo sapiens	4	0.7437
Albumin	P02768	ALBU_HUMAN	Homo sapiens	4	0.7437
Pol polyprotein	P32542	POL_EIAVC	Equine infectious anemia virus	4	0.7384
Pol polyprotein	P32542	POL_EIAVC	Equine infectious anemia virus	4	0.7384
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7351
Leucoanthocyanidin dioxygenase	Q96323	LDOX_ARATH	Arabidopsis thaliana	4	0.7351
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.7334
Aldehyde dehydrogenase, mitochondrial	P05091	ALDH2_HUMAN	Homo sapiens	4	0.7334
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7308
Proton-gated ion channel	Q7NDN8	GLIC_GLOVI	Gloeobacter violaceus	3	0.7308
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7256
Uracil phosphoribosyltransferase	Q26998	UPP_TOXGO	Toxoplasma gondii	3	0.7256
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	5	0.7243
Reticuline oxidase	P30986	RETO_ESCCA	Eschscholzia californica	5	0.7243
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7240
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A	O76083	PDE9A_HUMAN	Homo sapiens	3	0.7240
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7210
Basic phospholipase A2 VRV-PL-VIIIa	P59071	PA2B8_DABRR	Daboia russelii	2	0.7210
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7158
Thymidine phosphorylase	Q7CP66	TYPH_SALTY	Salmonella typhimurium	3	0.7158
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	4	0.7137
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B	Q13370	PDE3B_HUMAN	Homo sapiens	4	0.7137
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7126
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7126
Cyclic GMP-AMP phosphodiesterase SMPDL3A	Q92484	ASM3A_HUMAN	Homo sapiens	2	0.7126
cGMP-dependent 3',5'-cyclic phosphodiesterase	O00408	PDE2A_HUMAN	Homo sapiens	3	0.7126
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7088
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7088
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7073
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha	Q4WP27	Q4WP27_ASPFU	Aspergillus fumigatus	3	0.7073
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7035
Neuropilin-1	O14786	NRP1_HUMAN	Homo sapiens	3	0.7035
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7026
Ribonuclease J	H9CZL7	H9CZL7_DEIRD	Deinococcus radiodurans	3	0.7026
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7021
Carbonic anhydrase 2	P00918	CAH2_HUMAN	Homo sapiens	3	0.7021

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