Glabranin - Compound Card

Glabranin

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Glabranin

Structure
Zoomed Structure
  • Family: Plantae - Leguminosae/Fabaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavanone
Canonical Smiles CC(=CCc1c(O)cc(c2c1O[C@@H](CC2=O)c1ccccc1)O)C
InChI InChI=1S/C20H20O4/c1-12(2)8-9-14-15(21)10-16(22)19-17(23)11-18(24-20(14)19)13-6-4-3-5-7-13/h3-8,10,18,21-22H,9,11H2,1-2H3/t18-/m0/s1
InChIKey DAWSYIQAGQMLFS-SFHVURJKSA-N
Formula C20H20O4
HBA 4
HBD 2
MW 324.38
Rotatable Bonds 3
TPSA 66.76
LogP 4.31
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 24
Formal Charge 0
Fraction CSP3 0.25
Exact Mass 324.14
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Tephrosia purpurea Leguminosae/Fabaceae Plantae 228354
2 Tephrosia rhodesica Leguminosae/Fabaceae Plantae 556521

Showing of synonyms

  • Atilaw Y, Muiva-Mutisya L, et al. (2017). Four Prenylflavone Derivatives with Antiplasmodial Activities from the Stem of Tephrosia purpurea subsp. Leptostachya. Molecules, 2017, 22(9), 1514. [View]
  • Atilaw Y, Muiva-Mutisya L, et al. (2020). Prenylated Flavonoids from the Roots of Tephrosia rhodesica. Journal of natural products, 2020, 83(8), 2390–2398. [View]
Pubchem: 124049
Kegg Ligand: C09752
Chebi: 5368
Nmrshiftdb2: 60059141
Metabolights: MTBLC5368
Bindingdb: 26663
CPRiL: 420315
Structure

SMILES: c1cccc(c12)OC(CC2=O)c3ccccc3

Level: 1

Mol. Weight: 324.38 g/mol

Structure

SMILES: c1cccc(c12)OCCC2=O

Level: 0

Mol. Weight: 324.38 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 324.38 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.62
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.58
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.12

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.07
Plasma Protein Binding
83.97
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
Non-Substrate
CYP 3A4 Inhibitor
Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
5.76
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
0.78
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Toxic
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
0.36
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
7.05
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
Toxic
T. Pyriformis
1.93
Rat (Acute)
1.96
Rat (Chronic Oral)
2.56
Fathead Minnow
4.76
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
404.18
Hydration Free Energy
-9.67
Log(D) at pH=7.4
3.39
Log(P)
5.26
Log S
-5.28
Log(Vapor Pressure)
-8.07
Melting Point
140.85
pKa Acid
7.5
pKa Basic
6.29
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.9450
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.9336
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.9182
NADPH dehydrogenase 1 Q02899 OYE1_SACPS Saccharomyces pastorianus 3 0.9099
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.9082
Alpha-ketoglutarate-dependent dioxygenase FTO Q9C0B1 FTO_HUMAN Homo sapiens 3 0.8957
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 4 0.8859
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8844
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.8790
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8786
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.8711
APH(2'')-Id O68183 O68183_ENTCA Enterococcus casseliflavus 4 0.8666
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8621
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.8590
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.8557
Epidermal growth factor receptor P00533 EGFR_HUMAN Homo sapiens 3 0.8540
Dihydrofolate reductase O30463 O30463_MYCAV Mycobacterium avium 4 0.8527
Xylose isomerase P24300 XYLA_STRRU Streptomyces rubiginosus 3 0.8498
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.8492
Sterol 14alpha-demethylase P9WPP9 CP51_MYCTU Mycobacterium tuberculosis 3 0.8461
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 3 0.8444
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8415
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.8384
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.8382
Dihydrofolate reductase P16184 DYR_PNECA Pneumocystis carinii 4 0.8378
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8353
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8349
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 4 0.8306
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.8290
Dihydrofolate reductase Q83AB2 Q83AB2_COXBU Coxiella burnetii 4 0.8244
HTH-type transcriptional regulator QacR P0A0N3 QACR_STAAM Staphylococcus aureus 3 0.8244
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.8231
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 4 0.8216
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8213
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 4 0.8185
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 5 0.8179
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8178
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.8174
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.8163
Fibroblast growth factor receptor 1 P11362 FGFR1_HUMAN Homo sapiens 3 0.8158
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.8154
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8143
Toxoflavin degrading enzyme E3SET7 E3SET7_PAEPO Paenibacillus polymyxa 3 0.8142
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.8085
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.8065
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 4 0.7998
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7996
Purine nucleoside phosphorylase DeoD-type P0ABP8 DEOD_ECOLI Escherichia coli 3 0.7972
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 3 0.7971
Cytohesin-2 Q99418 CYH2_HUMAN Homo sapiens 3 0.7950
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.7946
Mitogen-activated protein kinase 14 Q16539 MK14_HUMAN Homo sapiens 3 0.7896
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 3 0.7888
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.7868
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7711
Probable NDP-rhamnosyltransferase Q9ALM8 Q9ALM8_SACSN Saccharopolyspora spinosa 3 0.7702
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7699
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 4 0.7695
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7683
Cyclin-dependent kinase 9 P50750 CDK9_HUMAN Homo sapiens 3 0.7652
Soluble cytochrome b562 P0ABE7 C562_ECOLX Escherichia coli 3 0.7629
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7621
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7605
Dihydrofolate reductase Q81R22 Q81R22_BACAN Bacillus anthracis 4 0.7603
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7601
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7600
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7598
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7584
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7570
Ephrin type-B receptor 4 P54760 EPHB4_HUMAN Homo sapiens 3 0.7519
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7509
Phosphoribosylformylglycinamidine synthase subunit PurL Q9X0X3 PURL_THEMA Thermotoga maritima 3 0.7506
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 3 0.7502
4-diphosphocytidyl-2-C-methyl-D-erythritol kinase O67060 ISPE_AQUAE Aquifex aeolicus 2 0.7499
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7495
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7489
Glycogen synthase kinase-3 beta P49841 GSK3B_HUMAN Homo sapiens 3 0.7488
Methionine aminopeptidase 2 P9WK19 MAP12_MYCTU Mycobacterium tuberculosis 3 0.7484
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7452
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7449
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7448
Estrogen receptor P03372 ESR1_HUMAN Homo sapiens 3 0.7444
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7441
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7421
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7413
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7406
Mitogen-activated protein kinase 8 P45983 MK08_HUMAN Homo sapiens 3 0.7398
Glucan 1,3-beta-glucosidase P29717 EXG1_CANAL Candida albicans 3 0.7387
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7378
Protein S100-A13 Q99584 S10AD_HUMAN Homo sapiens 3 0.7376
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7376
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7371
Orf1a polyprotein Q692E5 Q692E5_CVHSA SARS coronavirus TJF 2 0.7364
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7354
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7352
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7351
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7340
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7332
NADPH-dependent oxidoreductase 2-alkenal reductase Q39172 AER_ARATH Arabidopsis thaliana 2 0.7328
cGMP-specific 3',5'-cyclic phosphodiesterase O76074 PDE5A_HUMAN Homo sapiens 6 0.7322
Methionine aminopeptidase 1 P53582 MAP11_HUMAN Homo sapiens 3 0.7317
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7306
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7305
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7304
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7300
Anthocyanidin 3-O-glucosyltransferase UFGT P51094 UFOG_VITVI Vitis vinifera 3 0.7299
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.7299
Mitochondrial poly(A) polymerase F1NBW0 F1NBW0_CHICK Gallus gallus 2 0.7291
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 2 0.7288
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7284
Metallo-beta-lactamase type 2 P52699 BLAB_SERMA Serratia marcescens 3 0.7279
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7267
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7263
Peptidyl-prolyl cis-trans isomerase FKBP5 Q13451 FKBP5_HUMAN Homo sapiens 3 0.7258
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7250
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7248
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7245
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7242
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7242
Ras-related protein Ral-B P11234 RALB_HUMAN Homo sapiens 2 0.7230
Angiopoietin-1 receptor Q02763 TIE2_HUMAN Homo sapiens 3 0.7223
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7213
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 5 0.7212
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.7198
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 3 0.7196
Metallo-beta-lactamase type 2 C7C422 BLAN1_KLEPN Klebsiella pneumoniae 2 0.7194
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform O02697 PK3CG_PIG Sus scrofa 5 0.7192
Glutathione S-transferase F2 P46422 GSTF2_ARATH Arabidopsis thaliana 3 0.7188
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.7181
NADH:flavin oxidoreductase Sye1 Q8EEC8 Q8EEC8_SHEON Shewanella oneidensis 2 0.7181
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 3 0.7175
Tyrosine-protein kinase Lck P06239 LCK_HUMAN Homo sapiens 3 0.7166
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7164
Cytidine and deoxycytidylate deaminase zinc-binding region Q82Y41 Q82Y41_NITEU Nitrosomonas europaea 3 0.7158
Dihydrofolate reductase P9WNX1 DYR_MYCTU Mycobacterium tuberculosis 4 0.7157
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7156
Stromelysin-1 P08254 MMP3_HUMAN Homo sapiens 3 0.7149
Genome polyprotein O92972 POLG_HCVJ4 Hepatitis C virus genotype 1b 3 0.7148
Dihydrofolate reductase P00381 DYR_LACCA Lacticaseibacillus casei 4 0.7144
Histone deacetylase 7 Q8WUI4 HDAC7_HUMAN Homo sapiens 3 0.7136
Uridine phosphorylase Q5XA29 Q5XA29_STRP6 Streptococcus pyogenes serotype M6 3 0.7135
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7131
Carbonic anhydrase 1 P00915 CAH1_HUMAN Homo sapiens 2 0.7131
Ribosome-inactivating protein 3 P25891 RIP3_MAIZE Zea mays 3 0.7130
1-deoxy-D-xylulose 5-phosphate reductoisomerase P45568 DXR_ECOLI Escherichia coli 2 0.7128
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7128
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 5 0.7127
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7126
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7112
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7105
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 4 0.7103
Vascular endothelial growth factor receptor 2 P35968 VGFR2_HUMAN Homo sapiens 3 0.7093
Cytochrome P450 1A1 P04798 CP1A1_HUMAN Homo sapiens 3 0.7092
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7090
UDP-N-acetylmuramoyl-tripeptide--D-alanyl-D-alanine ligase Q8DNV6 Q8DNV6_STRR6 Streptococcus pneumoniae 3 0.7078
Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase Q9TQS6 DHDH_MACFA Macaca fascicularis 3 0.7077
Biflaviolin synthase CYP158A1 Q9KZF5 C1581_STRCO Streptomyces coelicolor / M145) 2 0.7075
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7069
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7066
CCA-adding enzyme O28126 CCA_ARCFU Archaeoglobus fulgidus 2 0.7058
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7052
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 2 0.7049
Prothrombin P00734 THRB_HUMAN Homo sapiens 2 0.7047
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 3 0.7043
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7036
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 3 0.7025
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7023
Tyrosine-protein kinase SYK P43405 KSYK_HUMAN Homo sapiens 4 0.7020
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7010
Genome polyprotein P26663 POLG_HCVBK Hepatitis C virus genotype 1b 3 0.7003

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