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

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

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

Structure
Zoomed Structure
  • Family: Plantae - Cyperaceae
  • Kingdom: Plantae
  • Class: Flavonoid
    • Subclass: Flavan
Canonical Smiles COc1cc(ccc1O)[C@@H]1CCc2c(O1)c(C)c(cc2OC)O
InChI InChI=1S/C18H20O5/c1-10-14(20)9-16(21-2)12-5-7-15(23-18(10)12)11-4-6-13(19)17(8-11)22-3/h4,6,8-9,15,19-20H,5,7H2,1-3H3/t15-/m0/s1
InChIKey UMHLYJUDKBXZDO-HNNXBMFYSA-N
Formula C18H20O5
HBA 5
HBD 2
MW 316.35
Rotatable Bonds 3
TPSA 68.15
LogP 3.49
Number Rings 3
Number Aromatic Rings 2
Heavy Atom Count 23
Formal Charge 0
Fraction CSP3 0.33
Exact Mass 316.13
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: 316.35 g/mol

Structure

SMILES: C1CCOc(c12)cccc2

Level: 0

Mol. Weight: 316.35 g/mol

Structure

SMILES: c1ccccc1

Level: 0

Mol. Weight: 316.35 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.59
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.750
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.14

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
1.170
Plasma Protein Binding
73.43
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
Non-Substrate
CYP 2C9 Inhibitor
Inhibitor
CYP 2C9 Substrate
Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
7.310
Organic Cation Transporter 2
Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
1.600
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Safe
Eye Corrosion
Safe
Eye Irritation
Toxic
Maximum Tolerated Dose
1.050
Liver Injury II
Toxic
hERG Blockers
Toxic
Daphnia Maga
5.960
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
2.370
Rat (Acute)
1.870
Rat (Chronic Oral)
2.240
Fathead Minnow
4.430
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
401.910
Hydration Free Energy
-9.160
Log(D) at pH=7.4
3.330
Log(P)
3.27
Log S
-4.75
Log(Vapor Pressure)
-7.12
Melting Point
141.11
pKa Acid
9.5
pKa Basic
5.13
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.9611
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.9583
Multidrug-efflux transporter 1 regulator P39075 BMRR_BACSU Bacillus subtilis 3 0.9311
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8927
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8926
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8800
cAMP-dependent protein kinase catalytic subunit alpha P17612 KAPCA_HUMAN Homo sapiens 3 0.8735
Thymidine phosphorylase Q7CP66 TYPH_SALTY Salmonella typhimurium 3 0.8672
Histone deacetylase 4 P56524 HDAC4_HUMAN Homo sapiens 3 0.8666
Uracil phosphoribosyltransferase Q26998 UPP_TOXGO Toxoplasma gondii 3 0.8656
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8634
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 3 0.8565
Peroxisome proliferator-activated receptor gamma P37231 PPARG_HUMAN Homo sapiens 4 0.8560
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8559
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8550
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8532
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.8524
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.8517
Sulfotransferase 2A1 Q06520 ST2A1_HUMAN Homo sapiens 4 0.8478
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.8431
Homoserine dehydrogenase P31116 DHOM_YEAST Saccharomyces cerevisiae 4 0.8404
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8403
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.8363
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.8285
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 3 0.8270
HTH-type transcriptional regulator QacR P0A0N4 QACR_STAAU Staphylococcus aureus 3 0.8259
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.8259
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 4 0.8251
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.8239
Rhodopsin kinase GRK1 P28327 GRK1_BOVIN Bos taurus 3 0.8229
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8205
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.8192
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.8168
Chitinase Q54276 Q54276_SERMA Serratia marcescens 3 0.8166
Aldo-keto reductase family 1 member C3 P42330 AK1C3_HUMAN Homo sapiens 3 0.8131
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.8128
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.8125
Purine nucleoside phosphorylase P00491 PNPH_HUMAN Homo sapiens 3 0.8103
DNA topoisomerase 4 subunit B H7C794 PARE_ENTFA Enterococcus faecalis 3 0.8091
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9QYJ6 PDE10_RAT Rattus norvegicus 4 0.8069
Hypoxanthine phosphoribosyltransferase Q4DRC4 Q4DRC4_TRYCC Trypanosoma cruzi 3 0.8035
Casein kinase II subunit alpha P68400 CSK21_HUMAN Homo sapiens 4 0.8013
Sulfide-quinone reductase B7JBP8 SQRD_ACIF2 Acidithiobacillus ferrooxidans) 4 0.8004
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.8001
Riboflavin synthase P0AFU8 RISA_ECOLI Escherichia coli 4 0.7999
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7992
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7990
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7989
Cytochrome P450 2C19 P33261 CP2CJ_HUMAN Homo sapiens 3 0.7954
UDP-glycosyltransferase 72B1 Q9M156 U72B1_ARATH Arabidopsis thaliana 4 0.7933
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7927
Chalcone--flavanone isomerase 1 P28012 CFI1_MEDSA Medicago sativa 4 0.7908
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7901
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7895
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7895
High affinity 3',5'-cyclic-AMP phosphodiesterase 7A Q13946 PDE7A_HUMAN Homo sapiens 3 0.7874
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7869
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7864
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7840
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7821
Flavoredoxin Q72HI0 Q72HI0_THET2 Thermus thermophilus 3 0.7806
Nodulin-13 P93330 NOD13_MEDTR Medicago truncatula 3 0.7791
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 3 0.7775
Tetracycline repressor protein class B from transposon Tn10 P04483 TETR2_ECOLX Escherichia coli 3 0.7748
Protein polybromo-1 Q86U86 PB1_HUMAN Homo sapiens 5 0.7743
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7736
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7719
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7711
Transthyretin Q9PTT3 Q9PTT3_SPAAU Sparus aurata 3 0.7710
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.7691
Gastrotropin P51161 FABP6_HUMAN Homo sapiens 3 0.7689
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 5 0.7667
Mitogen-activated protein kinase 1 P28482 MK01_HUMAN Homo sapiens 3 0.7661
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7659
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7641
Leucoanthocyanidin dioxygenase Q96323 LDOX_ARATH Arabidopsis thaliana 4 0.7632
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7632
Cyclic nucleotide-binding protein B8FW11 B8FW11_DESHD Desulfitobacterium hafniense 3 0.7629
Soluble acetylcholine receptor Q8WSF8 Q8WSF8_APLCA Aplysia californica 3 0.7615
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7610
HTH-type transcriptional repressor PurR P0ACP7 PURR_ECOLI Escherichia coli 3 0.7604
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7581
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7564
Nitric oxide synthase 1 P29476 NOS1_RAT Rattus norvegicus 3 0.7557
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7551
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7542
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7541
Nitric oxide synthase, inducible P29477 NOS2_MOUSE Mus musculus 3 0.7533
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.7518
TDP-4-oxo-6-deoxy-alpha-D-glucose-3,4-oxoisomerase Q6T1W8 FDTA_ANETH Aneurinibacillus thermoaerophilus 4 0.7503
GTPase KRas P01116 RASK_HUMAN Homo sapiens 3 0.7502
Proliferating cell nuclear antigen P12004 PCNA_HUMAN Homo sapiens 3 0.7500
Catechol O-methyltransferase P22734 COMT_RAT Rattus norvegicus 3 0.7499
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 3 0.7491
High affinity cGMP-specific 3',5'-cyclic phosphodiesterase 9A O76083 PDE9A_HUMAN Homo sapiens 3 0.7483
Major pollen allergen Bet v 1-A P15494 BEV1A_BETPN Betula pendula 3 0.7468
Ribosomal protein S6 kinase alpha-3 P18654 KS6A3_MOUSE Mus musculus 6 0.7465
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7459
Thymidylate synthase P0A886 TYSY_ECO57 Escherichia coli O157:H7 3 0.7447
Serine/threonine-protein kinase Chk1 O14757 CHK1_HUMAN Homo sapiens 3 0.7427
Aromatase P11511 CP19A_HUMAN Homo sapiens 3 0.7427
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7425
Heat shock protein HSP 90-beta P08238 HS90B_HUMAN Homo sapiens 3 0.7423
Deoxynucleoside kinase Q9XZT6 DNK_DROME Drosophila melanogaster 5 0.7421
Gag-Pol polyprotein P12497 POL_HV1N5 Human immunodeficiency virus type 1 group M subtype B 3 0.7410
Non-receptor tyrosine-protein kinase TYK2 P29597 TYK2_HUMAN Homo sapiens 4 0.7407
Lanosterol 14-alpha demethylase A6ZSR0 A6ZSR0_YEAS7 Saccharomyces cerevisiae 3 0.7405
Thymidine phosphorylase P07650 TYPH_ECOLI Escherichia coli 4 0.7398
Serine/threonine-protein kinase 10 O94804 STK10_HUMAN Homo sapiens 3 0.7388
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7365
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7360
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 4 0.7348
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 5 0.7347
rRNA N-glycosylase D9J2T9 D9J2T9_MOMBA Momordica balsamina 3 0.7345
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase Q05603 COBT_SALTY Salmonella typhimurium 2 0.7342
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7335
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 3 0.7329
HTH-type transcriptional regulator TtgR Q9AIU0 TTGR_PSEPT Pseudomonas putida 3 0.7329
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 2 0.7308
17beta-hydroxysteroid dehydrogenase O93874 O93874_COCLU Cochliobolus lunatus 4 0.7296
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 5 0.7294
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7293
Polymerase acidic protein C3W5S0 C3W5S0_I09A0 Influenza A virus 2 0.7293
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 4 0.7292
Serine/threonine-protein kinase 24 Q9Y6E0 STK24_HUMAN Homo sapiens 3 0.7281
Tyrosine-protein kinase JAK2 O60674 JAK2_HUMAN Homo sapiens 3 0.7281
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7280
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 3 0.7250
Glycogen synthase Q9V2J8 Q9V2J8_PYRAB Pyrococcus abyssi 3 0.7249
Neocarzinostatin P0A3R9 NCZS_STRCZ Streptomyces carzinostaticus 3 0.7240
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7236
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7235
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7234
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 P04191 AT2A1_RABIT Oryctolagus cuniculus 3 0.7226
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7218
Death-associated protein kinase 1 P53355 DAPK1_HUMAN Homo sapiens 4 0.7213
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7209
histidine kinase O32393 O32393_ARTPT Arthrospira platensis 3 0.7207
3',5'-cyclic-AMP phosphodiesterase 4B Q07343 PDE4B_HUMAN Homo sapiens 3 0.7199
Flavin-dependent thymidylate synthase Q9WYT0 THYX_THEMA Thermotoga maritima 3 0.7191
tyrosine--tRNA ligase Q4QFJ7 Q4QFJ7_LEIMA Leishmania major 3 0.7189
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 3 0.7187
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7186
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 4 0.7170
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.7167
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 3 0.7167
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 4 0.7154
Beta-galactoside-specific lectin 4 Q6ITZ3 ML4_VISAL Viscum album 2 0.7138
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 3 0.7127
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7125
Carbonic anhydrase 12 O43570 CAH12_HUMAN Homo sapiens 2 0.7123
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 5 0.7121
Nitric oxide synthase oxygenase O34453 NOSO_BACSU Bacillus subtilis 3 0.7117
Lethal factor P15917 LEF_BACAN Bacillus anthracis 3 0.7096
Histone deacetylase 8 Q9BY41 HDAC8_HUMAN Homo sapiens 3 0.7096
Ribulose-1,5 bisphosphate carboxylase/oxygenase large subunit N-methyltransferase, chloroplastic Q43088 RBCMT_PEA Pisum sativum 3 0.7087
Gag-Pol polyprotein P03367 POL_HV1BR Human immunodeficiency virus type 1 group M subtype B 4 0.7069
Bromodomain-containing protein 4 O60885 BRD4_HUMAN Homo sapiens 3 0.7056
Thymidylate synthase P00469 TYSY_LACCA Lacticaseibacillus casei 3 0.7045
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.7044
cGMP-inhibited 3',5'-cyclic phosphodiesterase 3B Q13370 PDE3B_HUMAN Homo sapiens 3 0.7041
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7038
Reticuline oxidase P30986 RETO_ESCCA Eschscholzia californica 4 0.7029
Poly [ADP-ribose] polymerase tankyrase-2 Q9H2K2 TNKS2_HUMAN Homo sapiens 4 0.7029
dTDP-4-dehydrorhamnose 3,5-epimerase A0A6L7H6N0 A0A1S0QLH9_BACAN Bacillus anthracis 3 0.7026
Glutamate receptor 2 P19491 GRIA2_RAT Rattus norvegicus 3 0.7024
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.7023
Dihydrofolate reductase P0A017 DYR_STAAU Staphylococcus aureus 3 0.7017
UDP-galactopyranose mutase Q48485 GLF1_KLEPN Klebsiella pneumoniae 3 0.7004

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