Natural Product: NPC53136

Natural Product ID:  NPC53136
Common Name:   4-Bromo-5-(Bromomethylene)-3-Butyl-2(5H)-Furanone
IUPAC Name:   (5Z)-4-bromo-5-(bromomethylidene)-3-butylfuran-2-one
Synonyms:  
Molecular Formula:   C9H10Br2O2
Standard InCHIKey:  UVJAGAXWVHGYRW-ALCCZGGFSA-N
Standard InCHI:  InChI=1S/C9H10Br2O2/c1-2-3-4-6-8(11)7(5-10)13-9(6)12/h5H,2-4H2,1H3/b7-5-
Canonical SMILES:  CCCCC1=C(Br)/C(=C/Br)/OC1=O
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
NPO14524 Delisea pulchra Species Bonnemaisoniaceae Eukaryota PMID[16933872]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MBC > 130 nM 11063613
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 100000 nM 11063613
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC = 50000 nM 11063613
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC = 30000 nM 11063613
NPT91 Cell Line KB Homo sapiens ED50 > 20 ug/ml 13678412
NPT2 Others Unspecified Inhibition = 39.9 % 10.1016/j.cropro.2012.04.001
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Activity > 50 % 26403929
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MBC > 130 nM 18808182
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 15000 nM 21036050
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MIC = 65000 nM 21036050
NPT91 Cell Line KB Homo sapiens ED50 > 20 ug/ml 24547740
NPT453 Cell Line HT-1080 Homo sapiens ED50 = 2.2 ug/ml PubChem BioAssay data set
NPT2 Others Unspecified ED50 = 10 ug/ml Open TG-GATES in vivo data: Organ Weight
NPT2 Others Unspecified ED50 > 20 ug/ml Open TG-GATES in vivo data: Biochemistry
NPT3085 Organism Penicillium oxalicum Penicillium oxalicum IZ = 3 mm 25978960
NPT133 Cell Line ZR-75-1 Homo sapiens ED50 = 10.2 ug/ml 22731892
NPT168 Cell Line P388 Mus musculus ED50 > 5 ug/ml 26042639
NPT2 Others Unspecified ED50 = 9.8 ug/ml 19433363
NPT91 Cell Line KB Homo sapiens ED50 > 20 ug/ml PubChem BioAssay data set
NPT6 Organism Plasmodium falciparum Plasmodium falciparum Activity > 50 % 19746919
NPT3085 Organism Penicillium oxalicum Penicillium oxalicum IZ = 3 mm 21623630
NPT2 Others Unspecified Inhibition = 75.8 % 16643031
NPT566 Organism Salmonella typhimurium Salmonella enterica subsp. enterica serovar Typhimurium IC50 = 23120 nM 23398362
NPT762 Cell Line A-431 Homo sapiens ED50 > 20 ug/ml 12798338
NPT2 Others Unspecified IC50 = 1362 nM 18215443
NPT2 Others Unspecified IC50 = 45000 nM 21168330
NPT1726 Organism Vibrio harveyi Vibrio harveyi GI50 = 65270 nM 8133298
NPT1034 Cell Line Lu1 Homo sapiens ED50 > 20 ug/ml 17194835
NPT2 Others Unspecified ED50 = 5.3 ug/ml 20194693
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MBC > 130 nM 31473
NPT79 Organism Bacillus subtilis Bacillus subtilis MBC = 100 nM 31473
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MBC > 130 nM 31473
NPT1460 Cell Line L929 Mus musculus Activity = 30 % 31473
NPT1548 Organism Pseudomonas aeruginosa PAO1 Pseudomonas aeruginosa PAO1 MIC > 130000 nM 31473
NPT1548 Organism Pseudomonas aeruginosa PAO1 Pseudomonas aeruginosa PAO1 MBC > 130 nM 31473
NPT858 Cell Line LNCaP Homo sapiens ED50 = 7.3 ug/ml 19654408
NPT17 Organism Staphylococcus epidermidis Staphylococcus epidermidis MBC > 130 nM 20585136
NPT2 Others Unspecified Inhibition = 5.9 % 23215538

  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 NPC53136 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
1.0 High Similarity NPC173409
0.9661 High Similarity NPC217537
0.8939 High Similarity NPC112983
0.8939 High Similarity NPC162571
0.8636 High Similarity NPC494
0.8594 High Similarity NPC475110
0.8429 Intermediate Similarity NPC238554
0.8429 Intermediate Similarity NPC225022
0.8261 Intermediate Similarity NPC146583
0.8143 Intermediate Similarity NPC177030
0.7857 Intermediate Similarity NPC269103
0.7857 Intermediate Similarity NPC124072
0.7808 Intermediate Similarity NPC228902
0.7808 Intermediate Similarity NPC24827
0.76 Intermediate Similarity NPC286816
0.76 Intermediate Similarity NPC199134
0.7465 Intermediate Similarity NPC475113
0.7465 Intermediate Similarity NPC299932
0.7273 Intermediate Similarity NPC133600
0.7206 Intermediate Similarity NPC132243
0.7162 Intermediate Similarity NPC188354
0.7067 Intermediate Similarity NPC469414
0.7067 Intermediate Similarity NPC329826
0.7 Intermediate Similarity NPC133904
0.7 Intermediate Similarity NPC131174
0.6944 Remote Similarity NPC287705
0.6944 Remote Similarity NPC218477
0.6923 Remote Similarity NPC478117
0.6901 Remote Similarity NPC248125
0.6883 Remote Similarity NPC68156
0.6818 Remote Similarity NPC86948
0.6812 Remote Similarity NPC151648
0.6795 Remote Similarity NPC85743
0.6795 Remote Similarity NPC102065
0.6761 Remote Similarity NPC220766
0.6761 Remote Similarity NPC182794
0.6712 Remote Similarity NPC474823
0.6667 Remote Similarity NPC429928
0.6667 Remote Similarity NPC191233
0.6667 Remote Similarity NPC173157
0.6667 Remote Similarity NPC186531
0.6667 Remote Similarity NPC84038
0.6667 Remote Similarity NPC315115
0.6667 Remote Similarity NPC133098
0.6622 Remote Similarity NPC475004
0.6622 Remote Similarity NPC232812
0.6579 Remote Similarity NPC474705
0.6575 Remote Similarity NPC21998
0.6575 Remote Similarity NPC203335
0.6533 Remote Similarity NPC67183
0.6533 Remote Similarity NPC37929
0.6533 Remote Similarity NPC64234
0.6528 Remote Similarity NPC470688
0.6528 Remote Similarity NPC471556
0.6522 Remote Similarity NPC286189
0.65 Remote Similarity NPC103560
0.6486 Remote Similarity NPC313444
0.6479 Remote Similarity NPC210303
0.6479 Remote Similarity NPC155849
0.6479 Remote Similarity NPC68110
0.6479 Remote Similarity NPC179087
0.6479 Remote Similarity NPC44343
0.6479 Remote Similarity NPC473737
0.6462 Remote Similarity NPC191643
0.6456 Remote Similarity NPC316324
0.641 Remote Similarity NPC478191
0.641 Remote Similarity NPC478194
0.641 Remote Similarity NPC478196
0.641 Remote Similarity NPC478192
0.641 Remote Similarity NPC478193
0.641 Remote Similarity NPC478195
0.64 Remote Similarity NPC265574
0.64 Remote Similarity NPC470693
0.64 Remote Similarity NPC473277
0.6377 Remote Similarity NPC189700
0.6364 Remote Similarity NPC287878
0.6364 Remote Similarity NPC144419
0.6351 Remote Similarity NPC132286
0.6341 Remote Similarity NPC42470
0.6338 Remote Similarity NPC15193
0.6329 Remote Similarity NPC123360
0.6316 Remote Similarity NPC316029
0.6316 Remote Similarity NPC315285
0.6316 Remote Similarity NPC315597
0.6301 Remote Similarity NPC471565
0.6301 Remote Similarity NPC476589
0.6301 Remote Similarity NPC471566
0.6282 Remote Similarity NPC476355
0.6282 Remote Similarity NPC117746
0.6282 Remote Similarity NPC474758
0.6282 Remote Similarity NPC259599
0.6282 Remote Similarity NPC15499
0.6282 Remote Similarity NPC294434
0.6269 Remote Similarity NPC478120
0.6269 Remote Similarity NPC218486
0.6267 Remote Similarity NPC470256
0.6267 Remote Similarity NPC470032
0.6267 Remote Similarity NPC238223
0.6267 Remote Similarity NPC280374
0.6267 Remote Similarity NPC79220
0.6267 Remote Similarity NPC276290
0.625 Remote Similarity NPC180290
0.625 Remote Similarity NPC474658
0.625 Remote Similarity NPC10572
0.625 Remote Similarity NPC135698
0.625 Remote Similarity NPC473825
0.625 Remote Similarity NPC54996
0.625 Remote Similarity NPC234084
0.625 Remote Similarity NPC57744
0.6234 Remote Similarity NPC163003
0.6216 Remote Similarity NPC116013
0.6216 Remote Similarity NPC37382
0.6203 Remote Similarity NPC329852
0.6197 Remote Similarity NPC309408
0.6197 Remote Similarity NPC130953
0.6197 Remote Similarity NPC79756
0.6176 Remote Similarity NPC49028
0.6173 Remote Similarity NPC315765
0.6173 Remote Similarity NPC299235
0.6173 Remote Similarity NPC471220
0.6173 Remote Similarity NPC128276
0.6164 Remote Similarity NPC471460
0.6164 Remote Similarity NPC475618
0.6163 Remote Similarity NPC469861
0.6163 Remote Similarity NPC469860
0.6163 Remote Similarity NPC130436
0.6154 Remote Similarity NPC269206
0.6154 Remote Similarity NPC295633
0.6154 Remote Similarity NPC236338
0.6154 Remote Similarity NPC58956
0.6133 Remote Similarity NPC225272
0.6133 Remote Similarity NPC472266
0.6133 Remote Similarity NPC194871
0.6125 Remote Similarity NPC27205
0.6119 Remote Similarity NPC473784
0.6098 Remote Similarity NPC63326
0.6098 Remote Similarity NPC472965
0.6098 Remote Similarity NPC264227
0.6098 Remote Similarity NPC178277
0.6098 Remote Similarity NPC265980
0.6098 Remote Similarity NPC63649
0.6098 Remote Similarity NPC150646
0.6087 Remote Similarity NPC150717
0.6087 Remote Similarity NPC221763
0.6076 Remote Similarity NPC140287
0.6076 Remote Similarity NPC470686
0.6071 Remote Similarity NPC8161
0.6049 Remote Similarity NPC53581
0.6049 Remote Similarity NPC103987
0.6049 Remote Similarity NPC187568
0.6049 Remote Similarity NPC41780
0.6047 Remote Similarity NPC281172
0.6032 Remote Similarity NPC270706
0.6027 Remote Similarity NPC2328
0.6027 Remote Similarity NPC217940
0.6027 Remote Similarity NPC474774
0.6026 Remote Similarity NPC129665
0.6026 Remote Similarity NPC257618
0.6024 Remote Similarity NPC474510
0.6023 Remote Similarity NPC475739
0.6023 Remote Similarity NPC472302
0.6 Remote Similarity NPC308294
0.6 Remote Similarity NPC142423
0.5976 Remote Similarity NPC108816
0.5976 Remote Similarity NPC93763
0.5976 Remote Similarity NPC222210
0.5976 Remote Similarity NPC63445
0.5974 Remote Similarity NPC236208
0.5974 Remote Similarity NPC88877
0.5974 Remote Similarity NPC476591
0.5972 Remote Similarity NPC98519
0.597 Remote Similarity NPC216407
0.597 Remote Similarity NPC151919
0.5955 Remote Similarity NPC95364
0.5955 Remote Similarity NPC142159
0.5952 Remote Similarity NPC325031
0.5952 Remote Similarity NPC471325
0.5938 Remote Similarity NPC128280
0.5926 Remote Similarity NPC235906
0.5926 Remote Similarity NPC473223
0.5909 Remote Similarity NPC27264
0.5904 Remote Similarity NPC270126
0.5904 Remote Similarity NPC471299
0.589 Remote Similarity NPC68044
0.5882 Remote Similarity NPC94875
0.5882 Remote Similarity NPC473529
0.5882 Remote Similarity NPC475159
0.5882 Remote Similarity NPC471326
0.5882 Remote Similarity NPC35556
0.5882 Remote Similarity NPC131002
0.5882 Remote Similarity NPC11332
0.5882 Remote Similarity NPC173609
0.5882 Remote Similarity NPC473712
0.5882 Remote Similarity NPC145914
0.5882 Remote Similarity NPC329829
0.5882 Remote Similarity NPC73310
0.5882 Remote Similarity NPC473780
0.5882 Remote Similarity NPC221231
0.5882 Remote Similarity NPC180363
0.5882 Remote Similarity NPC65930

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC53136 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
0.6061 Remote Similarity NPD6927 Phase 3
0.5882 Remote Similarity NPD5209 Approved
0.5867 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5854 Remote Similarity NPD4756 Discovery
0.5802 Remote Similarity NPD8039 Approved
0.5781 Remote Similarity NPD3174 Discontinued
0.5698 Remote Similarity NPD4752 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   9839657
ChEMBL   CHEMBL448241
ZINC  

Physicochemical Properties

Molecular Weight:  307.90
ALogP:  0.571
MLogP:  2.01
XLogP:  4.095
# Rotatable Bonds:  6
Polar Surface Area:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  13

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs