Natural Product: NPC304495

Natural Product ID:  NPC304495
Common Name:   22,23-Dihydrocucurbitacin E
IUPAC Name:   [(6R)-6-[(8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-8,10,12,15,16,17-hexahydro-7H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxoheptan-2-yl] acetate
Synonyms:   22,23-Dihydrocucurbitacin E
Molecular Formula:   C32H46O8
Standard InCHIKey:  XZBVNQWNPRMHRH-LAMASETHSA-N
Standard InCHI:  InChI=1S/C32H46O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,14,19,21-22,25,34-35,39H,11-13,15-16H2,1-9H3/t19-,21-,22+,25+,29+,30-,31+,32+/m1/s1
Canonical SMILES:  CC(=O)OC(CCC(=O)[C@@]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC(=O)[C@@]1([C@H]2CC=C2[C@H]1C=C(O)C(=O)C2(C)C)C)C)(O)C)(C)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
NPO27538 Hemsleya macrosperma Species Cucurbitaceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT24 Organism Human immunodeficiency virus 1 Human immunodeficiency virus 1 EC50 = 2.4 ug/ml 18088099
NPT1452 Cell Line C8166 Homo sapiens CC50 = 21.6 ug/ml 18088099
NPT2 Others Unspecified Ratio CC50/EC50 = 9.2 18088099
NPT81 Cell Line A549 Homo sapiens IC50 > 100000 nM 22472043

  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 NPC304495 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
0.9314 High Similarity NPC196528
0.92 High Similarity NPC474720
0.9151 High Similarity NPC221144
0.8972 High Similarity NPC170487
0.8899 High Similarity NPC148458
0.8879 High Similarity NPC118860
0.8879 High Similarity NPC231589
0.8879 High Similarity NPC214797
0.8868 High Similarity NPC241927
0.8868 High Similarity NPC258543
0.8868 High Similarity NPC470257
0.8857 High Similarity NPC58370
0.8857 High Similarity NPC43285
0.8818 High Similarity NPC239273
0.8796 High Similarity NPC475524
0.8796 High Similarity NPC100267
0.8796 High Similarity NPC280782
0.8727 High Similarity NPC270958
0.8716 High Similarity NPC202889
0.8713 High Similarity NPC42042
0.8704 High Similarity NPC43775
0.8673 High Similarity NPC42675
0.8661 High Similarity NPC472933
0.8649 High Similarity NPC472934
0.8624 High Similarity NPC71348
0.8611 High Similarity NPC197428
0.8598 High Similarity NPC470269
0.8585 High Similarity NPC181265
0.8571 High Similarity NPC111323
0.8571 High Similarity NPC118638
0.8545 High Similarity NPC52634
0.8545 High Similarity NPC472926
0.8529 High Similarity NPC49371
0.8522 High Similarity NPC141196
0.8522 High Similarity NPC1980
0.8522 High Similarity NPC238005
0.8505 High Similarity NPC44063
0.8491 Intermediate Similarity NPC235889
0.8482 Intermediate Similarity NPC472927
0.8482 Intermediate Similarity NPC471854
0.8476 Intermediate Similarity NPC473928
0.8476 Intermediate Similarity NPC22388
0.8462 Intermediate Similarity NPC218383
0.8426 Intermediate Similarity NPC94529
0.8416 Intermediate Similarity NPC206810
0.8411 Intermediate Similarity NPC96377
0.8407 Intermediate Similarity NPC311554
0.8407 Intermediate Similarity NPC257457
0.8403 Intermediate Similarity NPC213634
0.8396 Intermediate Similarity NPC140723
0.8378 Intermediate Similarity NPC194100
0.8378 Intermediate Similarity NPC962
0.8376 Intermediate Similarity NPC198714
0.8376 Intermediate Similarity NPC93368
0.8365 Intermediate Similarity NPC197386
0.8365 Intermediate Similarity NPC147954
0.8349 Intermediate Similarity NPC2766
0.8333 Intermediate Similarity NPC475294
0.8318 Intermediate Similarity NPC29705
0.8318 Intermediate Similarity NPC137657
0.8318 Intermediate Similarity NPC310586
0.8318 Intermediate Similarity NPC255309
0.8318 Intermediate Similarity NPC96268
0.8305 Intermediate Similarity NPC152091
0.8302 Intermediate Similarity NPC15396
0.8302 Intermediate Similarity NPC87351
0.8291 Intermediate Similarity NPC277191
0.8291 Intermediate Similarity NPC190846
0.8286 Intermediate Similarity NPC241221
0.8286 Intermediate Similarity NPC167974
0.8276 Intermediate Similarity NPC222688
0.8273 Intermediate Similarity NPC129689
0.8261 Intermediate Similarity NPC109973
0.8252 Intermediate Similarity NPC469599
0.8241 Intermediate Similarity NPC472935
0.8241 Intermediate Similarity NPC231530
0.8241 Intermediate Similarity NPC278628
0.8235 Intermediate Similarity NPC25750
0.823 Intermediate Similarity NPC49492
0.823 Intermediate Similarity NPC266728
0.8224 Intermediate Similarity NPC159442
0.8224 Intermediate Similarity NPC236390
0.8224 Intermediate Similarity NPC117185
0.8224 Intermediate Similarity NPC311612
0.8214 Intermediate Similarity NPC250109
0.8214 Intermediate Similarity NPC472929
0.8208 Intermediate Similarity NPC99411
0.8208 Intermediate Similarity NPC472924
0.8198 Intermediate Similarity NPC115303
0.8198 Intermediate Similarity NPC472928
0.819 Intermediate Similarity NPC271387
0.819 Intermediate Similarity NPC153792
0.8182 Intermediate Similarity NPC286174
0.8182 Intermediate Similarity NPC77947
0.8182 Intermediate Similarity NPC250018
0.8174 Intermediate Similarity NPC319570
0.8174 Intermediate Similarity NPC5292
0.8173 Intermediate Similarity NPC328162
0.8173 Intermediate Similarity NPC305483
0.8173 Intermediate Similarity NPC58052
0.8173 Intermediate Similarity NPC173272
0.8173 Intermediate Similarity NPC96859
0.8173 Intermediate Similarity NPC111684
0.8173 Intermediate Similarity NPC125622
0.8165 Intermediate Similarity NPC220974
0.8165 Intermediate Similarity NPC472925
0.8148 Intermediate Similarity NPC2436
0.8148 Intermediate Similarity NPC216245
0.8148 Intermediate Similarity NPC228669
0.8148 Intermediate Similarity NPC135854
0.8148 Intermediate Similarity NPC470251
0.8148 Intermediate Similarity NPC164835
0.8142 Intermediate Similarity NPC474181
0.8142 Intermediate Similarity NPC471398
0.8142 Intermediate Similarity NPC473898
0.8142 Intermediate Similarity NPC470953
0.8137 Intermediate Similarity NPC154101
0.8136 Intermediate Similarity NPC473255
0.8131 Intermediate Similarity NPC473788
0.8131 Intermediate Similarity NPC56498
0.8131 Intermediate Similarity NPC475320
0.8131 Intermediate Similarity NPC195290
0.8131 Intermediate Similarity NPC53222
0.8131 Intermediate Similarity NPC204450
0.8131 Intermediate Similarity NPC475558
0.8131 Intermediate Similarity NPC308726
0.8131 Intermediate Similarity NPC308351
0.8131 Intermediate Similarity NPC119601
0.8131 Intermediate Similarity NPC271266
0.812 Intermediate Similarity NPC216866
0.8119 Intermediate Similarity NPC326627
0.8119 Intermediate Similarity NPC310010
0.8119 Intermediate Similarity NPC54689
0.8119 Intermediate Similarity NPC477943
0.8115 Intermediate Similarity NPC469674
0.8113 Intermediate Similarity NPC144956
0.8113 Intermediate Similarity NPC83709
0.8113 Intermediate Similarity NPC287833
0.8113 Intermediate Similarity NPC472972
0.8113 Intermediate Similarity NPC476274
0.8108 Intermediate Similarity NPC27551
0.8108 Intermediate Similarity NPC206595
0.8108 Intermediate Similarity NPC114961
0.8108 Intermediate Similarity NPC473627
0.8103 Intermediate Similarity NPC79579
0.8095 Intermediate Similarity NPC18509
0.8095 Intermediate Similarity NPC43747
0.8091 Intermediate Similarity NPC295244
0.8087 Intermediate Similarity NPC153440
0.8077 Intermediate Similarity NPC69548
0.8077 Intermediate Similarity NPC184848
0.8077 Intermediate Similarity NPC317586
0.8077 Intermediate Similarity NPC470016
0.8077 Intermediate Similarity NPC48330
0.8077 Intermediate Similarity NPC241156
0.8077 Intermediate Similarity NPC472932
0.8073 Intermediate Similarity NPC475571
0.807 Intermediate Similarity NPC190286
0.8058 Intermediate Similarity NPC233118
0.8058 Intermediate Similarity NPC243866
0.8058 Intermediate Similarity NPC152897
0.8058 Intermediate Similarity NPC109414
0.8058 Intermediate Similarity NPC66429
0.8056 Intermediate Similarity NPC33973
0.8056 Intermediate Similarity NPC70967
0.8056 Intermediate Similarity NPC191892
0.8053 Intermediate Similarity NPC73455
0.8053 Intermediate Similarity NPC200944
0.8039 Intermediate Similarity NPC289213
0.8037 Intermediate Similarity NPC163372
0.8037 Intermediate Similarity NPC476240
0.8037 Intermediate Similarity NPC477053
0.8037 Intermediate Similarity NPC474327
0.8037 Intermediate Similarity NPC476223
0.8037 Intermediate Similarity NPC477051
0.8037 Intermediate Similarity NPC146822
0.8037 Intermediate Similarity NPC477052
0.8037 Intermediate Similarity NPC302537
0.8037 Intermediate Similarity NPC124211
0.8037 Intermediate Similarity NPC224720
0.8036 Intermediate Similarity NPC207689
0.8036 Intermediate Similarity NPC470281
0.8034 Intermediate Similarity NPC470921
0.8034 Intermediate Similarity NPC46570
0.8033 Intermediate Similarity NPC471855
0.802 Intermediate Similarity NPC294480
0.802 Intermediate Similarity NPC183546
0.8019 Intermediate Similarity NPC235464
0.8019 Intermediate Similarity NPC166745
0.8019 Intermediate Similarity NPC477813
0.8019 Intermediate Similarity NPC119036
0.8019 Intermediate Similarity NPC114274
0.8019 Intermediate Similarity NPC477854
0.8017 Intermediate Similarity NPC221414
0.8 Intermediate Similarity NPC473265
0.8 Intermediate Similarity NPC328371
0.8 Intermediate Similarity NPC185
0.8 Intermediate Similarity NPC155676
0.8 Intermediate Similarity NPC470882
0.8 Intermediate Similarity NPC95565

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC304495 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
0.8704 High Similarity NPD6650 Approved
0.8704 High Similarity NPD6649 Approved
0.8692 High Similarity NPD6372 Approved
0.8692 High Similarity NPD6373 Approved
0.8627 High Similarity NPD6083 Phase 2
0.8627 High Similarity NPD6084 Phase 2
0.8624 High Similarity NPD8297 Approved
0.8614 High Similarity NPD5695 Phase 3
0.8598 High Similarity NPD6881 Approved
0.8598 High Similarity NPD6899 Approved
0.8585 High Similarity NPD6675 Approved
0.8585 High Similarity NPD5739 Approved
0.8585 High Similarity NPD6402 Approved
0.8585 High Similarity NPD7128 Approved
0.8532 High Similarity NPD8130 Phase 1
0.8505 High Similarity NPD5697 Approved
0.8455 Intermediate Similarity NPD6882 Approved
0.844 Intermediate Similarity NPD7102 Approved
0.844 Intermediate Similarity NPD7290 Approved
0.844 Intermediate Similarity NPD6883 Approved
0.8426 Intermediate Similarity NPD7320 Approved
0.8365 Intermediate Similarity NPD5696 Approved
0.8364 Intermediate Similarity NPD6869 Approved
0.8364 Intermediate Similarity NPD6847 Approved
0.8364 Intermediate Similarity NPD6617 Approved
0.8349 Intermediate Similarity NPD6013 Approved
0.8349 Intermediate Similarity NPD6014 Approved
0.8349 Intermediate Similarity NPD6012 Approved
0.8333 Intermediate Similarity NPD5701 Approved
0.8261 Intermediate Similarity NPD6319 Approved
0.8257 Intermediate Similarity NPD6011 Approved
0.8214 Intermediate Similarity NPD4632 Approved
0.8119 Intermediate Similarity NPD4753 Phase 2
0.8113 Intermediate Similarity NPD5286 Approved
0.8113 Intermediate Similarity NPD5285 Approved
0.8113 Intermediate Similarity NPD4696 Approved
0.8095 Intermediate Similarity NPD4755 Approved
0.8077 Intermediate Similarity NPD5210 Approved
0.8077 Intermediate Similarity NPD4629 Approved
0.8036 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.8 Intermediate Similarity NPD6009 Approved
0.7983 Intermediate Similarity NPD7492 Approved
0.7963 Intermediate Similarity NPD5224 Approved
0.7963 Intermediate Similarity NPD5226 Approved
0.7963 Intermediate Similarity NPD5225 Approved
0.7963 Intermediate Similarity NPD5211 Phase 2
0.7963 Intermediate Similarity NPD4633 Approved
0.7961 Intermediate Similarity NPD6050 Approved
0.7949 Intermediate Similarity NPD6054 Approved
0.7944 Intermediate Similarity NPD4700 Approved
0.7941 Intermediate Similarity NPD6080 Approved
0.7941 Intermediate Similarity NPD6904 Approved
0.7941 Intermediate Similarity NPD6673 Approved
0.7934 Intermediate Similarity NPD7736 Approved
0.7917 Intermediate Similarity NPD6616 Approved
0.7913 Intermediate Similarity NPD6274 Approved
0.7909 Intermediate Similarity NPD6008 Approved
0.7899 Intermediate Similarity NPD7604 Phase 2
0.789 Intermediate Similarity NPD5175 Approved
0.789 Intermediate Similarity NPD5174 Approved
0.7881 Intermediate Similarity NPD5983 Phase 2
0.787 Intermediate Similarity NPD5223 Approved
0.7864 Intermediate Similarity NPD5692 Phase 3
0.7863 Intermediate Similarity NPD7101 Approved
0.7863 Intermediate Similarity NPD7100 Approved
0.7851 Intermediate Similarity NPD8293 Discontinued
0.7851 Intermediate Similarity NPD7078 Approved
0.7843 Intermediate Similarity NPD5737 Approved
0.7843 Intermediate Similarity NPD6672 Approved
0.7822 Intermediate Similarity NPD5690 Phase 2
0.7822 Intermediate Similarity NPD5330 Approved
0.7822 Intermediate Similarity NPD7334 Approved
0.7822 Intermediate Similarity NPD7521 Approved
0.7822 Intermediate Similarity NPD7146 Approved
0.7822 Intermediate Similarity NPD6684 Approved
0.7822 Intermediate Similarity NPD6409 Approved
0.7818 Intermediate Similarity NPD5141 Approved
0.7815 Intermediate Similarity NPD6370 Approved
0.7807 Intermediate Similarity NPD6053 Discontinued
0.7797 Intermediate Similarity NPD6059 Approved
0.7788 Intermediate Similarity NPD5284 Approved
0.7788 Intermediate Similarity NPD5281 Approved
0.7788 Intermediate Similarity NPD4634 Approved
0.7788 Intermediate Similarity NPD5694 Approved
0.7778 Intermediate Similarity NPD6335 Approved
0.7769 Intermediate Similarity NPD6336 Discontinued
0.7768 Intermediate Similarity NPD4729 Approved
0.7768 Intermediate Similarity NPD4730 Approved
0.7748 Intermediate Similarity NPD4767 Approved
0.7748 Intermediate Similarity NPD4768 Approved
0.7731 Intermediate Similarity NPD6015 Approved
0.7731 Intermediate Similarity NPD6016 Approved
0.7723 Intermediate Similarity NPD5329 Approved
0.7714 Intermediate Similarity NPD6399 Phase 3
0.7692 Intermediate Similarity NPD6317 Approved
0.7679 Intermediate Similarity NPD6412 Phase 2
0.767 Intermediate Similarity NPD6903 Approved
0.767 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7667 Intermediate Similarity NPD5988 Approved
0.7664 Intermediate Similarity NPD5222 Approved
0.7664 Intermediate Similarity NPD5221 Approved
0.7664 Intermediate Similarity NPD5220 Clinical (unspecified phase)
0.7664 Intermediate Similarity NPD4697 Phase 3
0.7647 Intermediate Similarity NPD6098 Approved
0.7647 Intermediate Similarity NPD5280 Approved
0.7647 Intermediate Similarity NPD5279 Phase 3
0.7647 Intermediate Similarity NPD4694 Approved
0.7632 Intermediate Similarity NPD5251 Approved
0.7632 Intermediate Similarity NPD5250 Approved
0.7632 Intermediate Similarity NPD5249 Phase 3
0.7632 Intermediate Similarity NPD5247 Approved
0.7632 Intermediate Similarity NPD5248 Approved
0.7627 Intermediate Similarity NPD6313 Approved
0.7627 Intermediate Similarity NPD6314 Approved
0.7624 Intermediate Similarity NPD3666 Approved
0.7624 Intermediate Similarity NPD4197 Approved
0.7624 Intermediate Similarity NPD3133 Approved
0.7624 Intermediate Similarity NPD3665 Phase 1
0.7619 Intermediate Similarity NPD6079 Approved
0.7619 Intermediate Similarity NPD5693 Phase 1
0.7611 Intermediate Similarity NPD5128 Approved
0.7596 Intermediate Similarity NPD5328 Approved
0.7593 Intermediate Similarity NPD5173 Approved
0.7583 Intermediate Similarity NPD6908 Approved
0.7583 Intermediate Similarity NPD6909 Approved
0.7583 Intermediate Similarity NPD6291 Clinical (unspecified phase)
0.757 Intermediate Similarity NPD6356 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD4754 Approved
0.7524 Intermediate Similarity NPD5207 Approved
0.7523 Intermediate Similarity NPD7638 Approved
0.7458 Intermediate Similarity NPD6868 Approved
0.7455 Intermediate Similarity NPD7639 Approved
0.7455 Intermediate Similarity NPD7640 Approved
0.7426 Intermediate Similarity NPD4223 Phase 3
0.7426 Intermediate Similarity NPD4221 Approved
0.7414 Intermediate Similarity NPD5217 Approved
0.7414 Intermediate Similarity NPD5215 Approved
0.7414 Intermediate Similarity NPD5216 Approved
0.7407 Intermediate Similarity NPD5654 Approved
0.7383 Intermediate Similarity NPD4202 Approved
0.7353 Intermediate Similarity NPD4788 Approved
0.7339 Intermediate Similarity NPD7507 Approved
0.7333 Intermediate Similarity NPD5208 Approved
0.7328 Intermediate Similarity NPD5169 Approved
0.7328 Intermediate Similarity NPD5135 Approved
0.7328 Intermediate Similarity NPD5134 Clinical (unspecified phase)
0.7317 Intermediate Similarity NPD8328 Phase 3
0.7315 Intermediate Similarity NPD7748 Approved
0.7308 Intermediate Similarity NPD3618 Phase 1
0.7282 Intermediate Similarity NPD4786 Approved
0.7273 Intermediate Similarity NPD7902 Approved
0.7273 Intermediate Similarity NPD5959 Approved
0.7265 Intermediate Similarity NPD5127 Approved
0.725 Intermediate Similarity NPD7115 Discovery
0.7222 Intermediate Similarity NPD6033 Approved
0.7217 Intermediate Similarity NPD6614 Approved
0.7188 Intermediate Similarity NPD7260 Phase 2
0.7165 Intermediate Similarity NPD7319 Approved
0.7156 Intermediate Similarity NPD6001 Approved
0.7155 Intermediate Similarity NPD6686 Approved
0.7143 Intermediate Similarity NPD4690 Approved
0.7143 Intermediate Similarity NPD4689 Approved
0.7143 Intermediate Similarity NPD4693 Phase 3
0.7143 Intermediate Similarity NPD5205 Approved
0.7143 Intermediate Similarity NPD4138 Approved
0.7143 Intermediate Similarity NPD4688 Approved
0.7143 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.713 Intermediate Similarity NPD6411 Approved
0.713 Intermediate Similarity NPD7515 Phase 2
0.7103 Intermediate Similarity NPD7285 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD6435 Approved
0.7087 Intermediate Similarity NPD3667 Approved
0.7083 Intermediate Similarity NPD5167 Approved
0.7069 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD5133 Approved
0.7059 Intermediate Similarity NPD4695 Discontinued
0.703 Intermediate Similarity NPD3617 Approved
0.7018 Intermediate Similarity NPD5091 Approved
0.7016 Intermediate Similarity NPD7503 Approved
0.7009 Intermediate Similarity NPD5168 Approved
0.7 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7900 Approved
0.7 Intermediate Similarity NPD5282 Discontinued
0.6992 Remote Similarity NPD4522 Approved
0.6977 Remote Similarity NPD5956 Approved
0.6972 Remote Similarity NPD8035 Phase 2
0.6972 Remote Similarity NPD8034 Phase 2
0.6961 Remote Similarity NPD4195 Approved
0.6957 Remote Similarity NPD6052 Approved
0.6949 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6944 Remote Similarity NPD6101 Approved
0.6944 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6916 Remote Similarity NPD3573 Approved
0.6909 Remote Similarity NPD5779 Approved
0.6909 Remote Similarity NPD5778 Approved
0.6893 Remote Similarity NPD5368 Approved
0.6891 Remote Similarity NPD6371 Approved
0.6881 Remote Similarity NPD4096 Approved
0.6881 Remote Similarity NPD5785 Approved
0.687 Remote Similarity NPD6845 Suspended

Structure

External Identifiers

PubChem CID   21577087
ChEMBL   CHEMBL256519
ZINC  

Physicochemical Properties

Molecular Weight:  558.32
ALogP:  1.0961
MLogP:  4.1
XLogP:  3.559
# Rotatable Bonds:  19
Polar Surface Area:  138.2
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  4
# Heavy Atoms:  40

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General Info & Identifiers & Properties  
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Biological Activities  
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