Dimethyl ellagic acid - Compound Card

Dimethyl ellagic acid

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Dimethyl ellagic acid

Structure
Zoomed Structure
  • Family: Plantae - Combretaceae
  • Kingdom: Plantae
  • Class: Tannin
    • Subclass: Ellagitannin
Canonical Smiles COc1c(O)cc2c3c1oc(=O)c1c3c(oc2=O)c(c(c1)O)OC
InChI InChI=1S/C16H10O8/c1-21-11-7(17)3-5-9-10-6(15(19)23-13(9)11)4-8(18)12(22-2)14(10)24-16(5)20/h3-4,17-18H,1-2H3
InChIKey KLAGYIBJNXLDTL-UHFFFAOYSA-N
Formula C16H10O8
HBA 8
HBD 2
MW 330.25
Rotatable Bonds 2
TPSA 119.34
LogP 1.92
Number Rings 4
Number Aromatic Rings 4
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.12
Exact Mass 330.04
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Terminalia species Combretaceae Plantae 39992
2 Reaumuria vermiculata Tamaricaceae Plantae 1518163
3 Terminalia brownii Combretaceae Plantae 1548809
4 Dacryodes edulis Burseraceae Plantae 246365
5 Desbordesia glaucescens Irvingiaceae Plantae 300981
6 Klainedoxa gabonensis Irvingiaceae Plantae 289639
7 Chrozophora oblongifolia Euphorbiaceae Plantae 344429
8 Melaleuca ericifolia Myrtaceae Plantae 73757
9 Combretum racemosum Combretaceae Plantae 2998935

Showing of synonyms

  • Famojuro TI, Adeyemi AA, et al. (2021). Anti-sickling activities of two isolated compounds from the root of Combretum racemosum P. beauv. (Combretaceae). Journal of Ethnopharmacology,2021,273, 113992. [View]
  • Wansi JD, Chiozem DD, et al. (2010). Antimicrobial and antioxidant effects of phenolic constituents from Klainedoxa gabonensis.. Pharmaceutical biology,2010, 48(10), 1124-1129. [View] [PubMed]
  • Nawwar MA, Ayoub NA, et al. (2012). Cytotoxic ellagitannins from Reaumuria vermiculata. Fitoterapia,2012,83(7),1256-1266. [View] [PubMed]
  • Kamel M.R, Nafady A.M, et al. (2021). Ent-trachylobane-3β-hydroperoxide, a new diterpene from the root bark of Chrozophora oblongifolia (Fam.; Euphorbiaceae). Natural product research, 2021, 35(19), 3177-3184. [View] [PubMed]
  • Hussein S.A, Hashim A.N, et al. (2007). Ericifolin: An eugenol 5-O-galloylglucoside and other phenolics from Melaleuca ericifolia. Phytochemistry,2007, 68(10), 1464-70. [View] [PubMed]
  • Dongmo KJJ, Tali MBT, et al. (2023). In vitro antiplasmodial activity and toxicological profile of extracts, fractions and chemical constituents of leaves and stem bark from Dacryodes edulis (Burseraceae).. BMC complementary medicine and therapies,2023, 23(1), 211. [View] [PubMed]
  • Kuete V, Dongmo Mafodong F, et al. (2017). In vitro cytotoxicity of compounds isolated from Desbordesia glaucescens against human carcinoma cell lines. South African Journal of Botany, 2017, 111, 37-43. [View]
  • Machumi F, Midiwo JO, et al. (2013). Phytochemical, antimicrobial and antiplasmodial investigations of Terminalia brownii. Natural Product Communications,2013,8(6),761-764. [View] [PubMed]
  • Pfundstein B, El Desouky SK, et al. (2010). Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): Characterization, quantitation and determination of antioxidant capacities. Phytochemistry,2010,71(10),1132-1148. [View] [PubMed]
CPRiL: 24004
Structure

SMILES: c12c3c4c(=O)oc2cccc1c(=O)oc3ccc4

Level: 0

Mol. Weight: 330.25 g/mol

Anti-plasmodial
Anti-sickling
Antimicrobial
Antioxidant
Cancer cell growth inhibitory

Absorption

Caco-2 (logPapp)
-4.75
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.710
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.07

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
1.540
Plasma Protein Binding
81.98
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Inhibitor
CYP 1A2 Inhibitor
Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
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
6.520
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.540
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.250
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
5.930
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
1.880
Rat (Acute)
2.310
Rat (Chronic Oral)
2.680
Fathead Minnow
4.960
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
495.460
Hydration Free Energy
-9.010
Log(D) at pH=7.4
4.310
Log(P)
1.56
Log S
-5.3
Log(Vapor Pressure)
-7.64
Melting Point
290.75
pKa Acid
8.21
pKa Basic
0.9
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9483
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9483
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9236
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9236
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.9051
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.9051
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9008
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.9008
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8976
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.8976
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8955
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8955
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8945
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.8945
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8848
NAD(P)H dehydrogenase [quinone] 1 P15559 NQO1_HUMAN Homo sapiens 4 0.8848
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8722
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8722
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8675
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8675
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8618
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8618
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8594
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.8594
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8472
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8472
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8462
2-phospho-L-lactate transferase Q8PVT6 COFD_METMA Methanosarcina mazei 3 0.8462
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8355
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8355
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8310
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8310
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8198
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 3 0.8198
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8130
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8130
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.8122
cAMP-dependent protein kinase catalytic subunit alpha P05132 KAPCA_MOUSE Mus musculus 3 0.8122
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8028
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.8028
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8011
NAD-capped RNA hydrolase NudC P32664 NUDC_ECOLI Escherichia coli 3 0.8011
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8002
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8002
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7993
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7993
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7984
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.7984
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7859
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7859
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7846
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7846
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7827
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7827
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7678
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7678
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7660
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7660
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7624
DNA polymerase III subunit epsilon P03007 DPO3E_ECOLI Escherichia coli 3 0.7624
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7598
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7598
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7572
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7572
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7555
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 3 0.7555
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7531
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7531
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7512
Biflaviolin synthase CYP158A2 Q9FCA6 C1582_STRCO Streptomyces coelicolor / M145) 3 0.7512
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7505
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7505
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7500
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7500
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7487
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 3 0.7487
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7486
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7486
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7470
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 3 0.7470
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7436
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7436
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7432
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7432
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7417
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7417
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7413
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7413
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7412
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7412
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7411
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7411
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7398
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7398
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7393
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7393
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7363
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 3 0.7363
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7360
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7360
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7338
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7338
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7317
cAMP-dependent protein kinase type II-beta regulatory subunit P12369 KAP3_RAT Rattus norvegicus 3 0.7317
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7304
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7304
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7275
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7275
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7264
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 3 0.7264
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7259
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7259
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7256
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7256
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7249
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7249
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7239
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.7239
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7237
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7237
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7206
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7206
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7201
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7201
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7180
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7180
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7162
Pancreatic alpha-amylase P04746 AMYP_HUMAN Homo sapiens 2 0.7162
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7139
Protoporphyrinogen oxidase, mitochondrial O24164 PPOM_TOBAC Nicotiana tabacum 2 0.7139
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7127
Protoporphyrinogen oxidase P50336 PPOX_HUMAN Homo sapiens 3 0.7127
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7114
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7114
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7102
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7102
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7089
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.7089
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7089
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7089
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7078
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7078
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7041
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7041
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7022
Diphtheria toxin P00588 DTX_CORBE Corynephage beta 3 0.7022

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