7-acetyl-1,4-dimethylazulene - Compound Card

7-acetyl-1,4-dimethylazulene

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7-acetyl-1,4-dimethylazulene

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Azulene Derivative
Canonical Smiles CC(=O)c1ccc(c2c(c1)c(C)cc2)C
InChI InChI=1S/C14H14O/c1-9-4-6-12(11(3)15)8-14-10(2)5-7-13(9)14/h4-8H,1-3H3
InChIKey ZZVZGSYEPXXGHA-UHFFFAOYSA-N
Formula C14H14O
HBA 1
HBD 0
MW 198.26
Rotatable Bonds 1
TPSA 17.07
LogP 3.61
Number Rings 2
Number Aromatic Rings 0
Heavy Atom Count 15
Formal Charge 0
Fraction CSP3 0.21
Exact Mass 198.1
Number of Lipinski Rule Violations 0
# Species Family Kingdom NCBI Taxonomy ID
1 Artemisia arborescens Asteraceae Plantae 72386

Showing of synonyms

  • Marco JA, Sanz-Cervera JF, et al. (1997). Sesquiterpene lactones and lignans from Artemisia arborescens.. Phytochemistry,1997,44(6),1133-1137. [View]
Pubchem: 15109166
Nmrshiftdb2: 60074680

No compound-protein relationship available.

Structure

SMILES: c1ccc(c12)ccccc2

Level: 0

Mol. Weight: 198.26 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-4.43
Human Oral Bioavailability 20%
Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-4.13
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Non-Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-2.68

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Penetrable
Fraction Unbound (Human)
0.8
Plasma Protein Binding
36.29
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
Non-Substrate
CYP 2D6 Inhibitor
Inhibitor
CYP 2D6 Substrate
Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Non-Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
11.61
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Toxic
Avian
Safe
Bee
Safe
Bioconcentration Factor
1.42
Biodegradation
Safe
Carcinogenesis
Toxic
Crustacean
Toxic
Liver Injury I (DILI)
Toxic
Eye Corrosion
Toxic
Eye Irritation
Toxic
Maximum Tolerated Dose
0.69
Liver Injury II
Toxic
hERG Blockers
Safe
Daphnia Maga
4.5
Micronucleos
Safe
NR-AhR
Safe
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
4.43
Rat (Acute)
1.8
Rat (Chronic Oral)
2.41
Fathead Minnow
3.95
Respiratory Disease
Safe
Skin Sensitisation
Toxic
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Safe
SR-p53
Safe

General Properties

Boiling Point
294.89
Hydration Free Energy
-4.04
Log(D) at pH=7.4
2.94
Log(P)
3.45
Log S
-3.35
Log(Vapor Pressure)
-2.33
Melting Point
80.12
pKa Acid
13.52
pKa Basic
11.49
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.9345
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 3 0.9345
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9329
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9329
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9310
Cyclin-dependent kinase 2 P24941 CDK2_HUMAN Homo sapiens 3 0.9310
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9175
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9175
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9103
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.9103
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.9090
Albumin P02769 ALBU_BOVIN Bos taurus 3 0.9090
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 4 0.9041
Aldo-keto reductase family 1 member B10 O60218 AK1BA_HUMAN Homo sapiens 4 0.9041
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9012
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A Q9Y233 PDE10_HUMAN Homo sapiens 3 0.9012
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8993
Bromodomain-containing protein 2 P25440 BRD2_HUMAN Homo sapiens 3 0.8993
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8866
Casein kinase II subunit alpha P28523 CSK2A_MAIZE Zea mays 3 0.8866
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8852
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8852
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8735
2,7-dihydroxy-5-methyl-1-naphthoate 7-O-methyltransferase Q84HC8 NCSB1_STRCZ Streptomyces carzinostaticus 3 0.8735
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.8733
Odorant-binding protein P81245 OBP_PIG Sus scrofa 3 0.8733
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.8646
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.8646
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8601
Photosynthetic reaction center cytochrome c subunit P07173 CYCR_BLAVI Blastochloris viridis 3 0.8601
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8577
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8577
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8517
Carminomycin 4-O-methyltransferase DnrK Q06528 DNRK_STRPE Streptomyces peucetius 3 0.8517
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.8316
Dihydroorotate dehydrogenase (quinone), mitochondrial Q08210 PYRD_PLAF7 Plasmodium falciparum 3 0.8316
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8281
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoform P48736 PK3CG_HUMAN Homo sapiens 3 0.8281
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.8258
Casein kinase II subunit alpha' P19784 CSK22_HUMAN Homo sapiens 3 0.8258
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8212
Carbonic anhydrase 2 P00918 CAH2_HUMAN Homo sapiens 3 0.8212
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8046
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.8046
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8025
Basic phospholipase A2 VRV-PL-VIIIa P59071 PA2B8_DABRR Daboia russelii 2 0.8025
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8013
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.8013
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7928
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7928
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7919
Heat shock protein HSP 90-alpha P07900 HS90A_HUMAN Homo sapiens 3 0.7919
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7912
Beta-2 adrenergic receptor P07550 ADRB2_HUMAN Homo sapiens 3 0.7912
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7903
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 3 0.7903
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7890
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7890
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7863
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7863
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7775
Tetracycline repressor protein class D P0ACT4 TETR4_ECOLX Escherichia coli 3 0.7775
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7774
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7774
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7696
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 3 0.7696
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7675
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7675
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7662
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7662
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7657
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 2 0.7657
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7654
Thymidine kinase P0DTH5 KITH_HHV11 Human herpesvirus 1 2 0.7654
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7591
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7591
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7558
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7558
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7558
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7558
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7549
Ribosyldihydronicotinamide dehydrogenase [quinone] P16083 NQO2_HUMAN Homo sapiens 2 0.7549
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7542
Corticosteroid-binding globulin P08185 CBG_HUMAN Homo sapiens 3 0.7542
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7524
Mycinamicin III 3''-O-methyltransferase Q49492 MYCF_MICGR Micromonospora griseorubida 2 0.7524
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7519
Acetylcholinesterase P21836 ACES_MOUSE Mus musculus 2 0.7519
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7515
3',5'-cyclic-AMP phosphodiesterase 4D Q08499 PDE4D_HUMAN Homo sapiens 3 0.7515
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7497
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7497
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7461
Serine/threonine-protein kinase pim-1 P11309 PIM1_HUMAN Homo sapiens 4 0.7461
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7443
Tetracycline repressor protein class H P51561 TETR8_PASMD Pasteurella multocida 2 0.7443
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7417
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7417
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7417
CmeR Q7B8P6 Q7B8P6_CAMJU Campylobacter jejuni 2 0.7417
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7372
Nuclear receptor subfamily 4immunitygroup A member 1 P22736 NR4A1_HUMAN Homo sapiens 2 0.7372
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7315
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7315
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7304
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 2 0.7304
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7298
Metallo-beta-lactamase type 2 P26918 BLAB_AERHY Aeromonas hydrophila 2 0.7298
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7247
Steroid Delta-isomerase P00947 SDIS_COMTE Comamonas testosteroni 2 0.7247
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7246
3'-5' exoribonuclease Rv2179c P9WJ73 EXRBN_MYCTU Mycobacterium tuberculosis 2 0.7246
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7238
Mycocyclosin synthase P9WPP7 CP121_MYCTU Mycobacterium tuberculosis 2 0.7238
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7234
Aldo-keto reductase family 1 member B1 P80276 ALDR_PIG Sus scrofa 3 0.7234
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7223
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 4 0.7223
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7218
Alcohol dehydrogenase E chain P00327 ADH1E_HORSE Equus caballus 3 0.7218
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7212
Cytochrome P450 monooxygenase Q5YNS8 Q5YNS8_NOCFA Nocardia farcinica 2 0.7212
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7191
Enoyl-[acyl-carrier-protein] reductase [NADH] P9WGR1 INHA_MYCTU Mycobacterium tuberculosis 3 0.7191
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7177
Nuclear receptor ROR-beta P45446 RORB_RAT Rattus norvegicus 2 0.7177
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7171
Aldo-keto reductase family 1 member B1 P15121 ALDR_HUMAN Homo sapiens 3 0.7171
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7165
Class B acid phosphatase Q540U1 APHA_SALTM Salmonella typhimurium 2 0.7165
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7163
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7163
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7152
17-beta-hydroxysteroid dehydrogenase type 1 P14061 DHB1_HUMAN Homo sapiens 2 0.7152
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7131
Prostaglandin reductase 2 Q8N8N7 PTGR2_HUMAN Homo sapiens 2 0.7131
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7124
Sulfotransferase 2B1 O00204 ST2B1_HUMAN Homo sapiens 2 0.7124
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7115
Chitinase A Q9AMP1 Q9AMP1_VIBHA Vibrio harveyi 2 0.7115
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7105
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7105
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7100
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7100
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 4 0.7085
Aldo-keto reductase family 1 member A1 P50578 AK1A1_PIG Sus scrofa 4 0.7085
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7084
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7084
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7079
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7079
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7074
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7074
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7058
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7058
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7055
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7055
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7052
Aldo-keto reductase family 1 member D1 P51857 AK1D1_HUMAN Homo sapiens 2 0.7052
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7040
Steroid Delta-isomerase P07445 SDIS_PSEPU Pseudomonas putida 2 0.7040
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7036
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha Q04631 FNTA_RAT Rattus norvegicus 3 0.7036
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7031
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7031
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7026
Gag-Pol polyprotein P03366 POL_HV1B1 Human immunodeficiency virus type 1 group M subtype B 3 0.7026
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7013
Ferrochelatase, mitochondrial P22830 HEMH_HUMAN Homo sapiens 2 0.7013
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7011
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7011
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7003
Gag-Pol polyprotein P04585 POL_HV1H2 Human immunodeficiency virus type 1 group M subtype B 3 0.7003

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