Natural Product: NPC471145

Natural Product ID:  NPC471145
Common Name:   Pungiolide A
IUPAC Name:   (3R,3aR,4'aR,5'S,6'aR,7R,8aS,9'aR,10'aR)-3'-acetyl-4'a-hydroxy-5',7-dimethyl-9'-methylidene-6-[(E)-3-oxobut-1-enyl]spiro[4,7,8,8a-tetrahydro-3aH-cyclohepta[b]furan-3,2'-5,6,6a,9a,10,10a-hexahydrofuro[1,2]cyclohepta[5,7-d]pyran]-2,8'-dione
Synonyms:  
Molecular Formula:   C29H34O8
Standard InCHIKey:  BGZGKGJBTWDZQU-PKNRYQKPSA-N
Standard InCHI:  InChI=1S/C29H34O8/c1-14-10-24-21(9-8-19(14)7-6-16(3)30)29(27(33)36-24)22(18(5)31)13-28(34)15(2)11-23-20(12-25(28)37-29)17(4)26(32)35-23/h6-8,13-15,20-21,23-25,34H,4,9-12H2,1-3,5H3/b7-6+/t14-,15+,20-,21-,23-,24+,25-,28+,29-/m1/s1
Canonical SMILES:  CC(=O)/C=C/C1=CC[C@@H]2[C@H](C[C@H]1C)OC(=O)[C@]12O[C@@H]2C[C@H]3[C@@H](C[C@@H]([C@]2(C=C1C(=O)C)O)C)OC(=O)C3=C
First Find Year:  
Max Developmental Stage:  
Synthetic Gene Cluster:   ;

  Species Source

Organism ID Organism Name Taxonomy Level Family SuperKingdom Isolation Part Collection Location Collection Time Reference
NPO32861 xanthium brasilicum Species Asteraceae Eukaryota PMID[23501116]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 > 30000 nM Open TG-GATES in vivo data: Biochemistry
NPT840 Individual Protein Transcriptional activator Myb Gallus gallus IC50 > 30000 nM 22276851
NPT840 Individual Protein Transcriptional activator Myb Gallus gallus IC50 = 50003.45 nM 18183025

  Similar Natural Products in NPASS

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

●  The left chart: Distribution of similarity level between NPC471145 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
0.9455 High Similarity NPC471146
0.8704 High Similarity NPC475871
0.8704 High Similarity NPC475945
0.8692 High Similarity NPC474742
0.8624 High Similarity NPC474741
0.8611 High Similarity NPC474747
0.8532 High Similarity NPC475873
0.8519 High Similarity NPC185141
0.8519 High Similarity NPC133907
0.8519 High Similarity NPC46998
0.8519 High Similarity NPC110443
0.8519 High Similarity NPC128733
0.844 Intermediate Similarity NPC149371
0.8364 Intermediate Similarity NPC472755
0.8349 Intermediate Similarity NPC47880
0.8319 Intermediate Similarity NPC38154
0.8304 Intermediate Similarity NPC26617
0.8288 Intermediate Similarity NPC203659
0.8288 Intermediate Similarity NPC100487
0.8273 Intermediate Similarity NPC472754
0.8224 Intermediate Similarity NPC475900
0.8198 Intermediate Similarity NPC110989
0.819 Intermediate Similarity NPC46269
0.819 Intermediate Similarity NPC106395
0.8182 Intermediate Similarity NPC472753
0.8148 Intermediate Similarity NPC476009
0.8125 Intermediate Similarity NPC472756
0.812 Intermediate Similarity NPC138303
0.812 Intermediate Similarity NPC133677
0.812 Intermediate Similarity NPC67290
0.8108 Intermediate Similarity NPC225353
0.8103 Intermediate Similarity NPC123855
0.8103 Intermediate Similarity NPC76550
0.8103 Intermediate Similarity NPC138757
0.8103 Intermediate Similarity NPC66108
0.8087 Intermediate Similarity NPC477103
0.8073 Intermediate Similarity NPC40812
0.8056 Intermediate Similarity NPC36954
0.8053 Intermediate Similarity NPC472749
0.8053 Intermediate Similarity NPC472751
0.8053 Intermediate Similarity NPC223450
0.8037 Intermediate Similarity NPC476300
0.8034 Intermediate Similarity NPC469454
0.8034 Intermediate Similarity NPC469463
0.8034 Intermediate Similarity NPC469496
0.8033 Intermediate Similarity NPC42747
0.8018 Intermediate Similarity NPC474339
0.8018 Intermediate Similarity NPC15993
0.8018 Intermediate Similarity NPC164598
0.8017 Intermediate Similarity NPC304180
0.8017 Intermediate Similarity NPC179798
0.8 Intermediate Similarity NPC477102
0.8 Intermediate Similarity NPC471144
0.7984 Intermediate Similarity NPC11732
0.7984 Intermediate Similarity NPC471940
0.7982 Intermediate Similarity NPC477513
0.7965 Intermediate Similarity NPC220964
0.7965 Intermediate Similarity NPC471143
0.7965 Intermediate Similarity NPC475676
0.7965 Intermediate Similarity NPC477510
0.7965 Intermediate Similarity NPC472748
0.7963 Intermediate Similarity NPC121825
0.7953 Intermediate Similarity NPC224623
0.7951 Intermediate Similarity NPC192309
0.7946 Intermediate Similarity NPC324017
0.7946 Intermediate Similarity NPC320019
0.7946 Intermediate Similarity NPC86077
0.7931 Intermediate Similarity NPC257240
0.792 Intermediate Similarity NPC172823
0.7913 Intermediate Similarity NPC233379
0.7913 Intermediate Similarity NPC14862
0.7913 Intermediate Similarity NPC474664
0.7903 Intermediate Similarity NPC471939
0.7895 Intermediate Similarity NPC9303
0.7895 Intermediate Similarity NPC16313
0.7895 Intermediate Similarity NPC475802
0.7895 Intermediate Similarity NPC243998
0.789 Intermediate Similarity NPC304886
0.7886 Intermediate Similarity NPC1538
0.7881 Intermediate Similarity NPC56448
0.7876 Intermediate Similarity NPC472747
0.7876 Intermediate Similarity NPC472750
0.7876 Intermediate Similarity NPC4620
0.787 Intermediate Similarity NPC81419
0.787 Intermediate Similarity NPC469645
0.787 Intermediate Similarity NPC469692
0.787 Intermediate Similarity NPC475912
0.787 Intermediate Similarity NPC179746
0.7869 Intermediate Similarity NPC470829
0.7869 Intermediate Similarity NPC473228
0.7863 Intermediate Similarity NPC287311
0.7857 Intermediate Similarity NPC201718
0.7857 Intermediate Similarity NPC476270
0.7857 Intermediate Similarity NPC13071
0.785 Intermediate Similarity NPC51004
0.7845 Intermediate Similarity NPC47951
0.7845 Intermediate Similarity NPC15218
0.7838 Intermediate Similarity NPC187761
0.7838 Intermediate Similarity NPC141191
0.7838 Intermediate Similarity NPC308567
0.7838 Intermediate Similarity NPC83895
0.7838 Intermediate Similarity NPC261377
0.7838 Intermediate Similarity NPC255592
0.7838 Intermediate Similarity NPC161855
0.7833 Intermediate Similarity NPC23046
0.7826 Intermediate Similarity NPC194620
0.7826 Intermediate Similarity NPC72813
0.7826 Intermediate Similarity NPC324327
0.7826 Intermediate Similarity NPC474421
0.7826 Intermediate Similarity NPC326994
0.7823 Intermediate Similarity NPC473919
0.7823 Intermediate Similarity NPC473709
0.7823 Intermediate Similarity NPC144625
0.7818 Intermediate Similarity NPC476315
0.7818 Intermediate Similarity NPC39859
0.7818 Intermediate Similarity NPC76862
0.7818 Intermediate Similarity NPC158416
0.7818 Intermediate Similarity NPC470883
0.7798 Intermediate Similarity NPC469632
0.7795 Intermediate Similarity NPC469351
0.7788 Intermediate Similarity NPC189609
0.7788 Intermediate Similarity NPC303653
0.7788 Intermediate Similarity NPC291500
0.7788 Intermediate Similarity NPC197835
0.7788 Intermediate Similarity NPC140591
0.7787 Intermediate Similarity NPC147635
0.7787 Intermediate Similarity NPC163693
0.7778 Intermediate Similarity NPC184463
0.7778 Intermediate Similarity NPC261607
0.7778 Intermediate Similarity NPC300312
0.7778 Intermediate Similarity NPC208886
0.7778 Intermediate Similarity NPC111114
0.7778 Intermediate Similarity NPC5103
0.7778 Intermediate Similarity NPC236999
0.7778 Intermediate Similarity NPC12172
0.7778 Intermediate Similarity NPC30515
0.7768 Intermediate Similarity NPC475949
0.7768 Intermediate Similarity NPC288876
0.7759 Intermediate Similarity NPC55972
0.7759 Intermediate Similarity NPC327286
0.7759 Intermediate Similarity NPC169888
0.7759 Intermediate Similarity NPC117604
0.7759 Intermediate Similarity NPC475960
0.7757 Intermediate Similarity NPC307411
0.7752 Intermediate Similarity NPC471136
0.7752 Intermediate Similarity NPC473548
0.7752 Intermediate Similarity NPC100017
0.7752 Intermediate Similarity NPC475154
0.7752 Intermediate Similarity NPC223356
0.7752 Intermediate Similarity NPC471137
0.7752 Intermediate Similarity NPC475500
0.7752 Intermediate Similarity NPC182266
0.775 Intermediate Similarity NPC54739
0.7748 Intermediate Similarity NPC169205
0.7748 Intermediate Similarity NPC474313
0.7742 Intermediate Similarity NPC473802
0.7739 Intermediate Similarity NPC469852
0.7731 Intermediate Similarity NPC209058
0.7727 Intermediate Similarity NPC14961
0.7727 Intermediate Similarity NPC471142
0.7727 Intermediate Similarity NPC270013
0.7706 Intermediate Similarity NPC135776
0.7705 Intermediate Similarity NPC477092
0.7699 Intermediate Similarity NPC477511
0.7699 Intermediate Similarity NPC150923
0.7699 Intermediate Similarity NPC264477
0.7685 Intermediate Similarity NPC476004
0.7685 Intermediate Similarity NPC474761
0.7679 Intermediate Similarity NPC187268
0.7679 Intermediate Similarity NPC470541
0.7679 Intermediate Similarity NPC54843
0.7672 Intermediate Similarity NPC266514
0.7672 Intermediate Similarity NPC469853
0.7672 Intermediate Similarity NPC470192
0.7658 Intermediate Similarity NPC31645
0.7658 Intermediate Similarity NPC185553
0.7658 Intermediate Similarity NPC17585
0.7658 Intermediate Similarity NPC473291
0.7656 Intermediate Similarity NPC477189
0.7656 Intermediate Similarity NPC475314
0.7656 Intermediate Similarity NPC251564
0.7656 Intermediate Similarity NPC475606
0.7652 Intermediate Similarity NPC309190
0.7647 Intermediate Similarity NPC95290
0.7647 Intermediate Similarity NPC317687
0.7647 Intermediate Similarity NPC189338
0.7636 Intermediate Similarity NPC167219
0.7636 Intermediate Similarity NPC190294
0.7636 Intermediate Similarity NPC477131
0.7636 Intermediate Similarity NPC474035
0.7636 Intermediate Similarity NPC81386
0.7634 Intermediate Similarity NPC68282
0.7632 Intermediate Similarity NPC473596
0.7632 Intermediate Similarity NPC471148
0.7632 Intermediate Similarity NPC66110
0.7627 Intermediate Similarity NPC115257
0.7627 Intermediate Similarity NPC161816
0.7623 Intermediate Similarity NPC13710
0.7623 Intermediate Similarity NPC475309
0.7623 Intermediate Similarity NPC475401

  Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

●  The left chart: Distribution of similarity level between NPC471145 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.8304 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7931 Intermediate Similarity NPD6371 Approved
0.7615 Intermediate Similarity NPD7983 Approved
0.7568 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD8513 Phase 3
0.7273 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7217 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7207 Intermediate Similarity NPD6698 Approved
0.7207 Intermediate Similarity NPD7838 Discovery
0.7207 Intermediate Similarity NPD46 Approved
0.7185 Intermediate Similarity NPD7966 Clinical (unspecified phase)
0.7168 Intermediate Similarity NPD5282 Discontinued
0.7165 Intermediate Similarity NPD8516 Approved
0.7165 Intermediate Similarity NPD8515 Approved
0.7165 Intermediate Similarity NPD8517 Approved
0.708 Intermediate Similarity NPD5779 Approved
0.708 Intermediate Similarity NPD5778 Approved
0.6894 Remote Similarity NPD8074 Phase 3
0.685 Remote Similarity NPD7115 Discovery
0.6822 Remote Similarity NPD6319 Approved
0.6814 Remote Similarity NPD1695 Approved
0.68 Remote Similarity NPD6053 Discontinued
0.678 Remote Similarity NPD4225 Approved
0.6757 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6754 Remote Similarity NPD5785 Approved
0.6752 Remote Similarity NPD7839 Suspended
0.6748 Remote Similarity NPD6686 Approved
0.6742 Remote Similarity NPD7492 Approved
0.6723 Remote Similarity NPD6648 Approved
0.6696 Remote Similarity NPD5786 Approved
0.6692 Remote Similarity NPD6616 Approved
0.6692 Remote Similarity NPD6054 Approved
0.6691 Remote Similarity NPD7260 Phase 2
0.6667 Remote Similarity NPD5344 Discontinued
0.6642 Remote Similarity NPD7078 Approved
0.6613 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6607 Remote Similarity NPD5363 Approved
0.6593 Remote Similarity NPD7736 Approved
0.6591 Remote Similarity NPD6370 Approved
0.6587 Remote Similarity NPD6649 Approved
0.6587 Remote Similarity NPD6650 Approved
0.6567 Remote Similarity NPD8273 Phase 1
0.6541 Remote Similarity NPD7642 Approved
0.6541 Remote Similarity NPD7829 Approved
0.6541 Remote Similarity NPD7830 Approved
0.6535 Remote Similarity NPD8297 Approved
0.6522 Remote Similarity NPD6845 Suspended
0.6522 Remote Similarity NPD6101 Approved
0.6522 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6515 Remote Similarity NPD6016 Approved
0.6515 Remote Similarity NPD6015 Approved
0.6466 Remote Similarity NPD5988 Approved
0.6444 Remote Similarity NPD8451 Approved
0.6439 Remote Similarity NPD6059 Approved
0.6429 Remote Similarity NPD6110 Phase 1
0.6429 Remote Similarity NPD6372 Approved
0.6429 Remote Similarity NPD6373 Approved
0.6423 Remote Similarity NPD7319 Approved
0.6418 Remote Similarity NPD8328 Phase 3
0.6412 Remote Similarity NPD7641 Discontinued
0.641 Remote Similarity NPD6411 Approved
0.6397 Remote Similarity NPD8448 Approved
0.6397 Remote Similarity NPD8293 Discontinued
0.6391 Remote Similarity NPD8444 Approved
0.637 Remote Similarity NPD8340 Approved
0.637 Remote Similarity NPD8299 Approved
0.637 Remote Similarity NPD8341 Approved
0.637 Remote Similarity NPD8342 Approved
0.6357 Remote Similarity NPD4632 Approved
0.6349 Remote Similarity NPD6881 Approved
0.6349 Remote Similarity NPD6899 Approved
0.6348 Remote Similarity NPD4251 Approved
0.6348 Remote Similarity NPD4250 Approved
0.6339 Remote Similarity NPD4270 Approved
0.6339 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6339 Remote Similarity NPD4269 Approved
0.6336 Remote Similarity NPD7500 Approved
0.6324 Remote Similarity NPD7507 Approved
0.6279 Remote Similarity NPD6882 Approved
0.6271 Remote Similarity NPD7637 Suspended
0.627 Remote Similarity NPD5697 Approved
0.6261 Remote Similarity NPD4249 Approved
0.6259 Remote Similarity NPD8392 Approved
0.6259 Remote Similarity NPD8391 Approved
0.6259 Remote Similarity NPD8390 Approved
0.625 Remote Similarity NPD7102 Approved
0.625 Remote Similarity NPD6883 Approved
0.625 Remote Similarity NPD5955 Clinical (unspecified phase)
0.625 Remote Similarity NPD5369 Approved
0.625 Remote Similarity NPD7290 Approved
0.6222 Remote Similarity NPD8080 Discontinued
0.622 Remote Similarity NPD7320 Approved
0.6212 Remote Similarity NPD6009 Approved
0.6202 Remote Similarity NPD6869 Approved
0.6202 Remote Similarity NPD6847 Approved
0.6202 Remote Similarity NPD6617 Approved
0.6202 Remote Similarity NPD8130 Phase 1
0.6195 Remote Similarity NPD6435 Approved
0.6195 Remote Similarity NPD5209 Approved
0.619 Remote Similarity NPD7128 Approved
0.619 Remote Similarity NPD6402 Approved
0.619 Remote Similarity NPD6675 Approved
0.619 Remote Similarity NPD5739 Approved
0.6182 Remote Similarity NPD4756 Discovery
0.6176 Remote Similarity NPD7604 Phase 2
0.6174 Remote Similarity NPD1694 Approved
0.6172 Remote Similarity NPD6013 Approved
0.6172 Remote Similarity NPD6012 Approved
0.6172 Remote Similarity NPD6014 Approved
0.6161 Remote Similarity NPD4252 Approved
0.6148 Remote Similarity NPD5983 Phase 2
0.6148 Remote Similarity NPD7503 Approved
0.6148 Remote Similarity NPD6921 Approved
0.614 Remote Similarity NPD7154 Phase 3
0.614 Remote Similarity NPD5362 Discontinued
0.6124 Remote Similarity NPD4634 Approved
0.6094 Remote Similarity NPD6011 Approved
0.609 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6087 Remote Similarity NPD6336 Discontinued
0.6077 Remote Similarity NPD2204 Approved
0.6063 Remote Similarity NPD6008 Approved
0.6048 Remote Similarity NPD7639 Approved
0.6048 Remote Similarity NPD7640 Approved
0.6047 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6042 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6029 Remote Similarity NPD8269 Approved
0.6029 Remote Similarity NPD8268 Approved
0.6029 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6029 Remote Similarity NPD8267 Approved
0.6029 Remote Similarity NPD8266 Approved
0.6018 Remote Similarity NPD4819 Approved
0.6018 Remote Similarity NPD5368 Approved
0.6018 Remote Similarity NPD4820 Approved
0.6018 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6018 Remote Similarity NPD4822 Approved
0.6018 Remote Similarity NPD4821 Approved
0.6016 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6016 Remote Similarity NPD5701 Approved
0.6016 Remote Similarity NPD6084 Phase 2
0.6016 Remote Similarity NPD6083 Phase 2
0.6 Remote Similarity NPD6033 Approved
0.5984 Remote Similarity NPD5695 Phase 3
0.5972 Remote Similarity NPD8415 Approved
0.5968 Remote Similarity NPD7638 Approved
0.5968 Remote Similarity NPD5696 Approved
0.5954 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5952 Remote Similarity NPD5211 Phase 2
0.595 Remote Similarity NPD6399 Phase 3
0.5915 Remote Similarity NPD5956 Approved
0.5913 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5897 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5891 Remote Similarity NPD6412 Phase 2
0.5882 Remote Similarity NPD7100 Approved
0.5882 Remote Similarity NPD7101 Approved
0.5878 Remote Similarity NPD2067 Discontinued
0.5859 Remote Similarity NPD5141 Approved
0.5852 Remote Similarity NPD7505 Discontinued
0.5841 Remote Similarity NPD4271 Approved
0.5841 Remote Similarity NPD4268 Approved
0.5841 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5839 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5833 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5809 Remote Similarity NPD7327 Approved
0.5809 Remote Similarity NPD6335 Approved
0.5809 Remote Similarity NPD7328 Approved
0.5808 Remote Similarity NPD7799 Discontinued
0.5806 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5798 Remote Similarity NPD7524 Approved
0.5797 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5797 Remote Similarity NPD8033 Approved
0.5794 Remote Similarity NPD5286 Approved
0.5794 Remote Similarity NPD5285 Approved
0.5794 Remote Similarity NPD4696 Approved
0.5778 Remote Similarity NPD6274 Approved
0.5778 Remote Similarity NPD690 Clinical (unspecified phase)
0.5766 Remote Similarity NPD7516 Approved
0.576 Remote Similarity NPD7902 Approved
0.5758 Remote Similarity NPD6421 Discontinued
0.575 Remote Similarity NPD6672 Approved
0.575 Remote Similarity NPD5737 Approved
0.5738 Remote Similarity NPD5284 Approved
0.5738 Remote Similarity NPD5694 Approved
0.5738 Remote Similarity NPD5693 Phase 1
0.5738 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5738 Remote Similarity NPD5281 Approved
0.5738 Remote Similarity NPD6050 Approved
0.5736 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5736 Remote Similarity NPD4057 Clinical (unspecified phase)
0.5735 Remote Similarity NPD6317 Approved
0.5735 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5726 Remote Similarity NPD5332 Approved
0.5726 Remote Similarity NPD5331 Approved
0.5725 Remote Similarity NPD8294 Approved
0.5725 Remote Similarity NPD8377 Approved
0.5723 Remote Similarity NPD8055 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6190 Approved
0.5714 Remote Similarity NPD7601 Clinical (unspecified phase)
0.5714 Remote Similarity NPD8039 Approved
0.5703 Remote Similarity NPD4633 Approved
0.5703 Remote Similarity NPD5224 Approved

Structure

External Identifiers

PubChem CID   73348839
ChEMBL   CHEMBL2380790
ZINC  

Physicochemical Properties

Molecular Weight:  510.23
ALogP:  -0.1242
MLogP:  3.77
XLogP:  1.704
# Rotatable Bonds:  8
Polar Surface Area:  116.2
# H-Bond Aceptor:  8
# H-Bond Donor:  1
# Rings:  5
# Heavy Atoms:  37

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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