Isopentenyl adenine - Compound Card

Isopentenyl adenine

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Isopentenyl adenine

Structure
Zoomed Structure
  • Family: Plantae - Apocynaceae
  • Kingdom: Plantae
  • Class: Nucleotide
Canonical Smiles CC(=CCNc1ncnc2c1[nH]cn2)C
InChI InChI=1S/C10H13N5/c1-7(2)3-4-11-9-8-10(13-5-12-8)15-6-14-9/h3,5-6H,4H2,1-2H3,(H2,11,12,13,14,15)
InChIKey HYVABZIGRDEKCD-UHFFFAOYSA-N
Formula C10H13N5
HBA 4
HBD 2
MW 203.25
Rotatable Bonds 3
TPSA 66.49
LogP 1.73
Number Rings 2
Number Aromatic Rings 2
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.3
Exact Mass 203.12
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Holarrhena africana Apocynaceae Plantae 2708850

Showing of synonyms

  • Nnadi CO, Nwodo NJ, et al. (2017). Steroid alkaloids from Holarrhena africana with strong activity against Trypanosoma brucei rhodesiense. Molecules, 2017, 22(7), 1129. [View]
Pubchem: 92180
Kegg Ligand: C04083
Chebi: 17660
Nmrshiftdb2: 60027609
Drugbank: DB08768
Pdb Ligand: ZIP
CPRiL: 69452
Structure

SMILES: [nH]1cnc(c12)ncnc2

Level: 0

Mol. Weight: 203.25 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.72
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.1
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-0.96

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.57
Plasma Protein Binding
28.91
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
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
10.27
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Safe
Bioconcentration Factor
-1.01
Biodegradation
Toxic
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
0.77
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
6.71
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
1.19
Rat (Acute)
2.45
Rat (Chronic Oral)
1.66
Fathead Minnow
5.9
Respiratory Disease
Toxic
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
416.45
Hydration Free Energy
-7.81
Log(D) at pH=7.4
1.61
Log(P)
2.02
Log S
-2.73
Log(Vapor Pressure)
-9.59
Melting Point
200.26
pKa Acid
10.24
pKa Basic
4.46
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 3 0.9462
MAP kinase-activated protein kinase 2 P49137 MAPK2_HUMAN Homo sapiens 3 0.9201
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 4 0.9026
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.8980
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8959
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.8905
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8894
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8892
Hypoxanthine-guanine phosphoribosyltransferase P00492 HPRT_HUMAN Homo sapiens 4 0.8802
Thiamine-phosphate synthase P39594 THIE_BACSU Bacillus subtilis 3 0.8788
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.8752
Purine nucleoside phosphorylase B9JYS2 B9JYS2_AGRVS Agrobacterium vitis 4 0.8745
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8737
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8673
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.8667
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.8655
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8632
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8629
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8595
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.8523
Hexokinase-4 P35557 HXK4_HUMAN Homo sapiens 3 0.8494
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 3 0.8465
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.8455
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.8438
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.8407
Dual specificity mitogen-activated protein kinase kinase 1 Q02750 MP2K1_HUMAN Homo sapiens 3 0.8367
Sulfotransferase 1A1 P50225 ST1A1_HUMAN Homo sapiens 3 0.8306
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.8170
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.8139
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.8129
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8103
cAMP-dependent protein kinase catalytic subunit alpha P00517 KAPCA_BOVIN Bos taurus 4 0.8080
Tyrosine-protein kinase JAK1 P23458 JAK1_HUMAN Homo sapiens 3 0.8056
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8027
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 4 0.8015
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8003
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7931
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7926
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7926
Sex hormone-binding globulin P04278 SHBG_HUMAN Homo sapiens 3 0.7922
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7910
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.7891
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7877
Beta-secretase 1 P56817 BACE1_HUMAN Homo sapiens 2 0.7876
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7874
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7874
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7870
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 2 0.7867
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7829
Pteridine reductase O76290 O76290_TRYBB Trypanosoma brucei brucei 2 0.7815
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7793
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7766
Nuclear receptor subfamily 1 group I member 2 O75469 NR1I2_HUMAN Homo sapiens 3 0.7763
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7757
Ribonuclease J H9CZL7 H9CZL7_DEIRD Deinococcus radiodurans 3 0.7751
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7750
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7750
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7742
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 2 0.7739
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7727
Queuine tRNA-ribosyltransferase P28720 TGT_ZYMMO Zymomonas mobilis subsp. mobilis 3 0.7724
Acetylcholine-binding protein P58154 ACHP_LYMST Lymnaea stagnalis 3 0.7713
Pheromone-binding protein ASP1 Q9U9J6 Q9U9J6_APIME Apis mellifera 3 0.7696
Nuclear receptor ROR-gamma P51449 RORG_HUMAN Homo sapiens 2 0.7693
Capsid protein VP1 O56137 O56137_9VIRU Adeno-associated virus - 6 3 0.7681
3-alpha-hydroxysteroid dehydrogenase P23457 DIDH_RAT Rattus norvegicus 2 0.7671
Bifunctional epoxide hydrolase 2 P34913 HYES_HUMAN Homo sapiens 3 0.7657
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7647
Retinol dehydratase Q26490 Q26490_SPOFR Spodoptera frugiperda 3 0.7639
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7632
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7631
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.7629
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7624
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7580
Androgen receptor P10275 ANDR_HUMAN Homo sapiens 2 0.7576
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7568
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 2 0.7541
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7506
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7498
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7494
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7480
Histone-lysine N-methyltransferase SETD7 Q8WTS6 SETD7_HUMAN Homo sapiens 3 0.7476
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7467
HLA class I histocompatibility antigen, B alpha chain P01889 HLAB_HUMAN Homo sapiens 3 0.7466
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7462
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7460
Retinol-binding protein 1 P09455 RET1_HUMAN Homo sapiens 3 0.7446
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7446
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7431
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 2 0.7427
Retinol-binding protein 1 P02696 RET1_RAT Rattus norvegicus 3 0.7396
Bromodomain adjacent to zinc finger domain protein 2B Q9UIF8 BAZ2B_HUMAN Homo sapiens 2 0.7396
Scytalone dehydratase P56221 SCYD_MAGO7 Pyricularia oryzae 3 0.7392
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7390
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7382
Phospholipase A2, major isoenzyme P00592 PA21B_PIG Sus scrofa 3 0.7380
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7366
Rhodopsin P02699 OPSD_BOVIN Bos taurus 2 0.7358
Lanosterol synthase P48449 ERG7_HUMAN Homo sapiens 3 0.7355
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 2 0.7353
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 2 0.7338
Polyprotein Q80J95 Q80J95_9CALI Murine norovirus 1 2 0.7324
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7322
Aldo-keto reductase family 1 member C1 Q04828 AK1C1_HUMAN Homo sapiens 2 0.7321
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7315
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7309
Methylketone synthase I E0YCS2 E0YCS2_SOLHA Solanum habrochaites 2 0.7309
glutaryl-CoA dehydrogenase (ETF) Q3JP94 Q3JP94_BURP1 Burkholderia pseudomallei 2 0.7296
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7291
Pteridine reductase, putative Q581W1 Q581W1_TRYB2 Trypanosoma brucei brucei 3 0.7290
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7288
Methionine aminopeptidase 2 P50579 MAP2_HUMAN Homo sapiens 3 0.7280
Beta-1 adrenergic receptor P07700 ADRB1_MELGA Meleagris gallopavo 2 0.7265
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7258
Aminoglycoside N(3)-acetyltransferase A0A3P1UCA6 Q81P86_BACAN Bacillus anthracis 3 0.7256
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7255
cGMP-dependent 3',5'-cyclic phosphodiesterase O00408 PDE2A_HUMAN Homo sapiens 3 0.7252
Endothiapepsin P11838 CARP_CRYPA Cryphonectria parasitica 3 0.7249
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7242
Ribosomal RNA small subunit methyltransferase E Q5SKI6 Q5SKI6_THET8 Thermus thermophilus 3 0.7240
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7236
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 2 0.7232
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7232
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 2 0.7226
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7217
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7213
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7203
Nuclear receptor subfamily 1 group I member 3 O35627 NR1I3_MOUSE Mus musculus 2 0.7193
5-methyltetrahydropteroyltriglutamate--homocysteine methyltransferase 1 O50008 METE1_ARATH Arabidopsis thaliana 2 0.7191
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7190
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 2 0.7186
Bifunctional dihydrofolate reductase-thymidylate synthase Q27783 DRTS_TRYBB Trypanosoma brucei brucei 3 0.7159
Sphingosine 1-phosphate receptor 1 P21453 S1PR1_HUMAN Homo sapiens 3 0.7156
Fatty acid-binding protein, adipocyte P15090 FABP4_HUMAN Homo sapiens 2 0.7146
Cellular retinol-binding protein type II Q8UVG6 Q8UVG6_DANRE Danio rerio 3 0.7144
D-aminoacyl-tRNA deacylase Q8IIS0 DTD_PLAF7 Plasmodium falciparum 2 0.7142
11-beta-hydroxysteroid dehydrogenase 1 P28845 DHI1_HUMAN Homo sapiens 3 0.7140
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7131
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7130
Histidine kinase 4 Q9C5U0 AHK4_ARATH Arabidopsis thaliana 3 0.7130
Ferrichrome outer membrane transporter/phage receptor P06971 FHUA_ECOLI Escherichia coli 3 0.7129
Mitogen-activated protein kinase 1 P63086 MK01_RAT Rattus norvegicus 3 0.7122
NAD(P)H-hydrate epimerase Q8K4Z3 NNRE_MOUSE Mus musculus 3 0.7121
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 2 0.7111
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7110
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7106
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7098
ActVA 6 protein Q53908 Q53908_STRCH Streptomyces coelicolor 3 0.7098
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 2 0.7092
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7086
4,4'-diapophytoene synthase A9JQL9 CRTM_STAAU Staphylococcus aureus 2 0.7084
Norsolorinic acid synthase Q12053 AFLC_ASPPU Aspergillus parasiticus 2 0.7080
Phosphotriesterase Q5KZU5 Q5KZU5_GEOKA Geobacillus kaustophilus 3 0.7080
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7077
Glutathione S-transferase P P09211 GSTP1_HUMAN Homo sapiens 2 0.7074
Pentaerythritol tetranitrate reductase P71278 P71278_ENTCL Enterobacter cloacae 2 0.7070
Death-associated protein kinase 3 O43293 DAPK3_HUMAN Homo sapiens 2 0.7068
Serine/threonine-protein kinase N1 Q16512 PKN1_HUMAN Homo sapiens 3 0.7064
Ribosomal RNA small subunit methyltransferase E Q5SKI6 Q5SKI6_THET8 Thermus thermophilus 3 0.7059
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.7054
Cytochrome P450 S6BVH1 S6BVH1_RHOER Rhodococcus erythropolis 2 0.7053
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7051
Sphingosine 1-phosphate receptor 1 P21453 S1PR1_HUMAN Homo sapiens 3 0.7046
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7046
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 2 0.7046
Purine nucleoside phosphorylase P55859 PNPH_BOVIN Bos taurus 4 0.7036
Bifunctional dihydrofolate reductase-thymidylate synthase P13922 DRTS_PLAFK Plasmodium falciparum 3 0.7032
Albumin P02768 ALBU_HUMAN Homo sapiens 2 0.7028
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7024
Tryptophan synthase alpha chain P00929 TRPA_SALTY Salmonella typhimurium 2 0.7022
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7020
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 2 0.7018
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7008
Cytochrome P450 2E1 P05181 CP2E1_HUMAN Homo sapiens 3 0.7008

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