3-methoxy-7-O-beta-(6′′-galloylglucopyranoside) kaempferol - Compound Card

3-methoxy-7-O-beta-(6′′-galloylglucopyranoside) kaempferol

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3-methoxy-7-O-beta-(6′′-galloylglucopyranoside) kaempferol

Structure
Zoomed Structure
  • Family: Plantae - Cistaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanol Glycoside
Canonical Smiles COc1c(oc2c(c1=O)c(O)cc(c2)O[C@H]1O[C@@H](COC(=O)c2cc(O)c(c(c2)O)O)[C@@H]([C@H]([C@@H]1O)O)O)c1ccc(cc1)O
InChI InChI=1S/C29H26O15/c1-40-27-23(36)20-15(31)8-14(9-18(20)43-26(27)11-2-4-13(30)5-3-11)42-29-25(38)24(37)22(35)19(44-29)10-41-28(39)12-6-16(32)21(34)17(33)7-12/h2-9,19,22,24-25,29-35,37-38H,10H2,1H3/t19-,22-,24+,25-,29-/m0/s1
InChIKey WRZIFQDTKJVDFU-WWCFVODUSA-N
Formula C29H26O15
HBA 15
HBD 8
MW 614.51
Rotatable Bonds 7
TPSA 246.04
LogP 1.04
Number Rings 5
Number Aromatic Rings 4
Heavy Atom Count 44
Formal Charge 0
Fraction CSP3 0.24
Exact Mass 614.13
Number of Lipinski Rule Violations 3
# Species Family Kingdom NCBI Taxonomy ID
1 Fumana montana Cistaceae Plantae 441235

Showing of synonyms

  • Laraoui H, Haba H, et al. (2019). A new flavanone sulfonate and other phenolic compounds from Fumana montana. Biochemical Systematics and Ecology, 2019, 86, 103927. [View]

No compound-protein relationship available.

Structure

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)Oc(cc3)cc(c34)oc(cc4=O)-c5ccccc5

Level: 3

Mol. Weight: 614.51 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCC(O2)Oc(cc3)cc(c34)occc4=O

Level: 2

Mol. Weight: 614.51 g/mol

Structure

SMILES: c1ccccc1-c(cc2=O)oc(c23)cc(cc3)OC4CCCCO4

Level: 2

Mol. Weight: 614.51 g/mol

Structure

SMILES: O=c1ccoc(c12)cc(cc2)OC3CCCCO3

Level: 1

Mol. Weight: 614.51 g/mol

Structure

SMILES: c1cccc(c12)oc(cc2=O)-c3ccccc3

Level: 1

Mol. Weight: 614.51 g/mol

Structure

SMILES: c1ccccc1C(=O)OCC2CCCCO2

Level: 1

Mol. Weight: 614.51 g/mol

Structure

SMILES: c1cccc(c12)occc2=O

Level: 0

Mol. Weight: 614.51 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 614.51 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 614.51 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-6.84
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Non-Absorbed
Madin-Darby Canine Kidney
-5.170
Human Oral Bioavailability 50%
Non-Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Substrate
Skin Permeability
14.66

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.870
Plasma Protein Binding
74.72
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
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
12.590
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-2.110
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
1.060
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.910
Micronucleos
Toxic
NR-AhR
Toxic
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
-24599.150
Rat (Acute)
2.400
Rat (Chronic Oral)
4.120
Fathead Minnow
50.760
Respiratory Disease
Safe
Skin Sensitisation
Safe
SR-ARE
Toxic
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Toxic

General Properties

Boiling Point
398.880
Hydration Free Energy
-2.970
Log(D) at pH=7.4
1.490
Log(P)
1.95
Log S
-6.22
Log(Vapor Pressure)
-15.97
Melting Point
225.46
pKa Acid
5.88
pKa Basic
5.56
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Cathepsin S P25774 CATS_HUMAN Homo sapiens 3 0.9569
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.9376
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.9339
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.9315
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.9210
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.9059
Glycogen phosphorylase, muscle form P00489 PYGM_RABIT Oryctolagus cuniculus 3 0.9042
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8931
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8928
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 4 0.8891
Capsid protein Q9WBP8 Q9WBP8_9VIRU Adeno-associated virus - 1 3 0.8852
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 3 0.8818
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8808
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8794
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.8763
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.8762
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8696
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8682
2',3'-cyclic-nucleotide 3'-phosphodiesterase P16330 CN37_MOUSE Mus musculus 3 0.8594
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8585
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8582
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8544
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8528
Valacyclovir hydrolase Q86WA6 BPHL_HUMAN Homo sapiens 3 0.8461
WxcM-like protein Q12KT8 Q12KT8_SHEDO Shewanella denitrificans 4 0.8450
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.8450
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8396
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8395
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.8393
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8341
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8336
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8272
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8268
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8238
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.8225
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8192
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 3 0.8180
ATP synthase subunit alpha, mitochondrial P19483 ATPA_BOVIN Bos taurus 3 0.8154
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.8134
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8119
Ephrin type-B receptor 2 P54763 EPHB2_MOUSE Mus musculus 3 0.8113
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.8101
Fibroblast growth factor receptor 2 P21802 FGFR2_HUMAN Homo sapiens 3 0.8085
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.8085
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8058
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.8055
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8032
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8010
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7955
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7943
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.7938
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 3 0.7924
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7920
Mitogen-activated protein kinase kinase kinase 5 Q99683 M3K5_HUMAN Homo sapiens 3 0.7912
Phenylalanine-4-hydroxylase P00439 PH4H_HUMAN Homo sapiens 3 0.7874
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7868
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7860
Disks large homolog 1 Q12959 DLG1_HUMAN Homo sapiens 4 0.7846
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 4 0.7842
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.7839
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7819
ATP-dependent molecular chaperone HSP82 P02829 HSP82_YEAST Saccharomyces cerevisiae 3 0.7810
Serine/threonine-protein kinase SKY1 Q03656 SKY1_YEAST Saccharomyces cerevisiae 3 0.7795
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7763
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7762
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 3 0.7762
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7737
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7724
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.7701
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7673
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7635
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7602
Protein ppBat Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron VPI-5482 2 0.7579
S-adenosylmethionine decarboxylase proenzyme P17707 DCAM_HUMAN Homo sapiens 4 0.7559
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7547
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7530
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7490
Lactotransferrin P24627 TRFL_BOVIN Bos taurus 2 0.7483
LIM domain kinase 1 P53667 LIMK1_HUMAN Homo sapiens 3 0.7471
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7459
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7458
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 3 0.7446
Alpha amylase B8CZ54 B8CZ54_HALOH Halothermothrix orenii 3 0.7445
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7438
Flavin-dependent monooxygenase Q93L51 TETX_BACT4 Bacteroides thetaiotaomicron 3 0.7413
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7409
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7407
Potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 4 Q9Y3Q4 HCN4_HUMAN Homo sapiens 4 0.7398
Succinate dehydrogenase flavoprotein subunit P0AC41 SDHA_ECOLI Escherichia coli 3 0.7397
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7385
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7380
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7355
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7337
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7333
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7325
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.7319
Biotin carboxylase P24182 ACCC_ECOLI Escherichia coli 3 0.7311
Deoxycytidine kinase P27707 DCK_HUMAN Homo sapiens 4 0.7309
Single-strand selective monofunctional uracil DNA glycosylase Q9YGN6 SMUG1_XENLA Xenopus laevis 4 0.7286
Cytosolic purine 5'-nucleotidase P49902 5NTC_HUMAN Homo sapiens 2 0.7285
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.7281
Serine/threonine-protein kinase toxin HipA P23874 HIPA_ECOLI Escherichia coli 3 0.7271
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7269
Acyl-coenzyme A synthetase ACSM2A, mitochondrial Q08AH3 ACS2A_HUMAN Homo sapiens 2 0.7269
4-hydroxyphenylacetate 3-monooxygenase Q8YHT7 Q8YHT7_BRUME Brucella melitensis biotype 1 2 0.7261
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7259
Polyribonucleotide nucleotidyltransferase A7ZS61 PNP_ECO24 Escherichia coli O139:H28 3 0.7256
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 3 0.7252
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7247
Putative protease I Q8A8A4 Q8A8A4_BACTN Bacteroides thetaiotaomicron 2 0.7246
Nucleoprotein P33469 NCAP_CVHOC Human coronavirus OC43 3 0.7243
Uridine phosphorylase Q9KT71 Q9KT71_VIBCH Vibrio cholerae serotype O1 4 0.7238
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7234
Proto-oncogene tyrosine-protein kinase Src P00523 SRC_CHICK Gallus gallus 3 0.7230
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7225
Thymidylate synthase P0A884 TYSY_ECOLI Escherichia coli 4 0.7222
tRNA (cytidine(56)-2'-O)-methyltransferase O58214 TRM56_PYRHO Pyrococcus horikoshii 4 0.7219
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 4 0.7209
Lethal(3)malignant brain tumor-like protein 1 Q9Y468 LMBL1_HUMAN Homo sapiens 3 0.7205
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7203
3-alpha-(or 20-beta)-hydroxysteroid dehydrogenase P19992 HSD_STREX Streptomyces exfoliatus 2 0.7193
NAD-dependent protein deacetylase Q9WYW0 NPD_THEMA Thermotoga maritima 3 0.7193
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7187
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7185
Peripheral plasma membrane protein CASK O14936 CSKP_HUMAN Homo sapiens 3 0.7180
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7176
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.7175
Bifunctional dihydrofolate reductase-thymidylate synthase O02604 DRTS_PLAVI Plasmodium vivax 3 0.7165
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7162
EbrA repressor Q79SH7 Q79SH7_STRLI Streptomyces lividans 3 0.7145
Transthyretin P02767 TTHY_RAT Rattus norvegicus 2 0.7144
Orotidine 5'-phosphate decarboxylase Q9KQT7 PYRF_VIBCH Vibrio cholerae serotype O1 4 0.7143
chitinase B0Y2Y2 B0Y2Y2_ASPFC Aspergillus fumigatus 4 0.7142
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7122
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7117
Methyltransferase D0VX01 D0VX01_WSLV Wesselsbron virus 4 0.7100
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7098
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7097
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7096
DNA mismatch repair protein Msh2 P43246 MSH2_HUMAN Homo sapiens 3 0.7096
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7096
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7096
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7087
Protein mono-ADP-ribosyltransferase PARP3 Q9Y6F1 PARP3_HUMAN Homo sapiens 3 0.7082
Hygromycin-B 4-O-kinase P00557 KHYB_ECOLX Escherichia coli 3 0.7073
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7064
DNA-directed DNA polymerase Q38087 DPOL_BPR69 Escherichia phage RB69 4 0.7061
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7059
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.7057
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7055
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 3 0.7044
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7040
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7028
Threonine--tRNA ligase P0A8M3 SYT_ECOLI Escherichia coli 3 0.7018
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7017

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