7,4′-dihydroxy-5,3′-dimethoxy-8-prenylflavan - Compound Card

7,4′-dihydroxy-5,3′-dimethoxy-8-prenylflavan

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7,4′-dihydroxy-5,3′-dimethoxy-8-prenylflavan

Structure
Zoomed Structure
  • Family: Plantae - Cyperaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavan
Canonical Smiles COc1cc(ccc1OC)C1CCc2c(O1)c(CC=C(C)C)c(cc2O)O
InChI InChI=1S/C22H26O5/c1-13(2)5-7-15-17(23)12-18(24)16-8-10-19(27-22(15)16)14-6-9-20(25-3)21(11-14)26-4/h5-6,9,11-12,19,23-24H,7-8,10H2,1-4H3
InChIKey DSTFQMMHFSBGGI-UHFFFAOYSA-N
Formula C22H26O5
HBA 5
HBD 2
MW 370.45
Rotatable Bonds 5
TPSA 68.15
LogP 4.69
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 27
Formal Charge 0
Fraction CSP3 0.36
Exact Mass 370.18
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Cyperus conglomeratus Cyperaceae Plantae 1423382

Showing of synonyms

  • Zaki A, Ross S, et al. (2018). New flavans and stilbenes from Cyperus conglomeratus. Phytochemistry Letters, 2018, 26, 159-163. [View]

No compound-protein relationship available.

Structure

SMILES: c1cccc(c12)OC(CC2)c3ccccc3

Level: 1

Mol. Weight: 370.45 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 370.45 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 370.45 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.69
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.680
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.47

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.010
Plasma Protein Binding
61.93
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Substrate
CYP 2C19 Inhibitor
Inhibitor
CYP 2C19 Substrate
Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
8.640
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.370
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.170
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.430
Micronucleos
Toxic
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Toxic
NR-PPAR-gamma
Safe
NR-TR
Toxic
T. Pyriformis
-1.710
Rat (Acute)
1.810
Rat (Chronic Oral)
2.420
Fathead Minnow
4.910
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
425.100
Hydration Free Energy
-7.090
Log(D) at pH=7.4
3.540
Log(P)
4.74
Log S
-5.28
Log(Vapor Pressure)
-7.55
Melting Point
126.36
pKa Acid
9.52
pKa Basic
6.6
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.9532
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9332
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9300
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9298
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 3 0.9223
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8938
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.8901
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8899
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8888
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8788
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8754
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8724
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8707
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8650
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.8623
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 5 0.8620
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8618
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8588
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.8496
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8492
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8429
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8419
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8409
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.8388
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8376
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8293
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8292
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8263
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 4 0.8262
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8260
Bromodomain testis-specific protein Q58F21 BRDT_HUMAN Homo sapiens 3 0.8210
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 3 0.8180
Heat shock protein 75 kDa, mitochondrial Q12931 TRAP1_HUMAN Homo sapiens 4 0.8175
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8164
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8148
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8134
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.8127
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.8114
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8110
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8110
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.8094
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8081
Pteridine reductase 1 Q01782 PTR1_LEIMA Leishmania major 3 0.8056
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.8032
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.8007
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7995
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7968
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7966
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7938
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7900
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7850
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 5 0.7849
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7844
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7839
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7828
Phosphatidylinositol 3-kinase catalytic subunit type 3 Q8NEB9 PK3C3_HUMAN Homo sapiens 4 0.7818
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7801
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7764
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 3 0.7739
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 3 0.7738
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7725
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 3 0.7723
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.7715
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7706
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7685
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7683
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7681
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7680
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7665
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7646
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7641
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7633
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7629
Thymidine phosphorylase P07650 TYPH_ECOLI Escherichia coli 4 0.7619
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7614
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7609
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7593
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.7588
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7570
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 5 0.7561
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7560
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7553
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7551
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7546
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7540
Tyrosine-protein kinase HCK P08631 HCK_HUMAN Homo sapiens 5 0.7533
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7530
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7530
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7522
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7489
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7489
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7474
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7469
Aminoglycoside 3'-phosphotransferase AphA1-IAB B0VD92 B0VD92_ACIBY Acinetobacter baumannii 3 0.7462
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7453
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7452
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 2 0.7449
Rhodopsin P02699 OPSD_BOVIN Bos taurus 3 0.7440
Ephrin type-A receptor 2 P29317 EPHA2_HUMAN Homo sapiens 3 0.7427
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7411
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7401
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7380
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 2 0.7375
RNA polymerase sigma factor SigA Q5SKW1 Q5SKW1_THET8 Thermus thermophilus 3 0.7345
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7344
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7337
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7328
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7303
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7294
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.7284
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 6 0.7283
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 3 0.7279
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7276
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7273
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7273
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7271
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7268
Liver carboxylesterase 1 P23141 EST1_HUMAN Homo sapiens 3 0.7268
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.7232
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7231
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 4 0.7230
Tubulin alpha-1B chain P81947 TBA1B_BOVIN Bos taurus 4 0.7216
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7216
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 4 0.7210
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7210
ABC-type polar amino acid transport system, ATPase component Q8RCC2 Q8RCC2_CALS4 Caldanaerobacter subterraneus subsp. tengcongensis 2 0.7201
Multidrug transporter MdfA P0AEY8 MDFA_ECOLI Escherichia coli 3 0.7179
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7176
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7176
Acetolactate synthase, chloroplastic P17597 ILVB_ARATH Arabidopsis thaliana 2 0.7170
Capsid scaffolding protein P88911 P88911_HHV8 Human herpesvirus 8 type M 3 0.7169
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7166
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7165
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7153
Ribosomal small subunit pseudouridine synthase A P0AA43 RSUA_ECOLI Escherichia coli 3 0.7153
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7143
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.7137
Dipeptidyl peptidase 4 P27487 DPP4_HUMAN Homo sapiens 3 0.7137
Dihydrofolate reductase P0ABQ4 DYR_ECOLI Escherichia coli 3 0.7136
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7129
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7121
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7116
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7115
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7112
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 2 0.7106
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7090
Angiotensin-converting enzyme 2 Q9BYF1 ACE2_HUMAN Homo sapiens 2 0.7085
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7081
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 2 0.7077
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7076
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7072
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7067
Fatty acid-binding protein, liver P80226 FABPL_CHICK Gallus gallus 3 0.7066
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 4 0.7064
O-methyltransferase family 2 D5STZ7 D5STZ7_PLAL2 Planctopirus limnophila 4 0.7055
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7055
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 3 0.7052
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 4 0.7052
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7050
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.7049
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.7048
3',5'-cyclic-AMP phosphodiesterase 4A P27815 PDE4A_HUMAN Homo sapiens 3 0.7040
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7035
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7032
Acetylcholinesterase P22303 ACES_HUMAN Homo sapiens 3 0.7021
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7015
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7010
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.7009
Carbonyl reductase [NADPH] 1 P16152 CBR1_HUMAN Homo sapiens 3 0.7008
Phytohormone-binding protein CSBP A0A1S3THR8 PHBP_VIGRR Vigna radiata var. radiata 3 0.7004
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7002

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