Natural Product: NPC475688

Natural Product ID:  NPC475688
Common Name:   N-(2,3-Dibromo-4,5-Dihydroxybenzyl)Pyroglutamic Acid
IUPAC Name:   1-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]-5-oxopyrrolidine-2-carboxylic acid
Synonyms:  
Molecular Formula:   C12H11Br2NO5
Standard InCHIKey:  HBQXJYDRHBZVJG-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C12H11Br2NO5/c13-9-5(3-7(16)11(18)10(9)14)4-15-6(12(19)20)1-2-8(15)17/h3,6,16,18H,1-2,4H2,(H,19,20)
Canonical SMILES:  OC(=O)C1CCC(=O)N1Cc1cc(O)c(c(c1Br)Br)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
NPO14137 Rhodomela confervoides Species Rhodomelaceae Eukaryota PMID[15921411]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT547 Cell Line BGC-823 Homo sapiens IC50 > 10 ug/ml 137981
NPT81 Cell Line A549 Homo sapiens IC50 > 10 ug/ml 137981
NPT20 Organism Candida albicans Candida albicans MIC50 > 100 ug/ml 22779787
NPT19 Organism Escherichia coli Escherichia coli MIC50 > 100 ug/ml 22779787
NPT181 Cell Line Bel-7402 Homo sapiens IC50 > 10 ug/ml 11076561
NPT83 Cell Line MCF7 Homo sapiens IC50 > 10 ug/ml 12350152
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC50 > 100 ug/ml 12350152
NPT180 Cell Line HCT-8 Homo sapiens IC50 > 10 ug/ml 20038624

  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 NPC475688 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
0.975 High Similarity NPC475120
0.9123 High Similarity NPC473941
0.85 High Similarity NPC226514
0.8035 Intermediate Similarity NPC288747
0.7919 Intermediate Similarity NPC191557
0.7596 Intermediate Similarity NPC249113
0.7486 Intermediate Similarity NPC129885
0.7321 Intermediate Similarity NPC125852
0.7134 Intermediate Similarity NPC243404
0.6914 Remote Similarity NPC142776
0.681 Remote Similarity NPC220311
0.6765 Remote Similarity NPC238412
0.6748 Remote Similarity NPC137117
0.6747 Remote Similarity NPC474087
0.6706 Remote Similarity NPC199089
0.6687 Remote Similarity NPC150929
0.6686 Remote Similarity NPC471328
0.6684 Remote Similarity NPC65714
0.6647 Remote Similarity NPC109580
0.6627 Remote Similarity NPC145888
0.6627 Remote Similarity NPC16031
0.6627 Remote Similarity NPC161593
0.6626 Remote Similarity NPC47790
0.6615 Remote Similarity NPC230539
0.659 Remote Similarity NPC470709
0.6583 Remote Similarity NPC471592
0.6557 Remote Similarity NPC474535
0.6548 Remote Similarity NPC85049
0.6548 Remote Similarity NPC474536
0.6527 Remote Similarity NPC13004
0.6522 Remote Similarity NPC475697
0.6513 Remote Similarity NPC80337
0.651 Remote Similarity NPC73555
0.6509 Remote Similarity NPC160081
0.6509 Remote Similarity NPC226493
0.6494 Remote Similarity NPC251439
0.6491 Remote Similarity NPC244890
0.6491 Remote Similarity NPC163560
0.6481 Remote Similarity NPC117759
0.6481 Remote Similarity NPC38483
0.648 Remote Similarity NPC234069
0.6471 Remote Similarity NPC88667
0.6453 Remote Similarity NPC6913
0.6453 Remote Similarity NPC245386
0.645 Remote Similarity NPC105702
0.6447 Remote Similarity NPC64140
0.6447 Remote Similarity NPC174122
0.6437 Remote Similarity NPC40321
0.6429 Remote Similarity NPC96275
0.6416 Remote Similarity NPC313694
0.6416 Remote Similarity NPC242159
0.6414 Remote Similarity NPC248822
0.6407 Remote Similarity NPC318965
0.6398 Remote Similarity NPC135006
0.6396 Remote Similarity NPC246591
0.6384 Remote Similarity NPC184632
0.6382 Remote Similarity NPC64066
0.6379 Remote Similarity NPC224663
0.6374 Remote Similarity NPC33338
0.6374 Remote Similarity NPC302171
0.6374 Remote Similarity NPC300020
0.6369 Remote Similarity NPC321561
0.6354 Remote Similarity NPC473608
0.6347 Remote Similarity NPC171372
0.6337 Remote Similarity NPC474135
0.6335 Remote Similarity NPC50782
0.6307 Remote Similarity NPC160932
0.6303 Remote Similarity NPC56634
0.6294 Remote Similarity NPC214553
0.6287 Remote Similarity NPC84606
0.6277 Remote Similarity NPC61004
0.6265 Remote Similarity NPC136543
0.6264 Remote Similarity NPC5194
0.6264 Remote Similarity NPC262166
0.6264 Remote Similarity NPC261934
0.6263 Remote Similarity NPC475123
0.6263 Remote Similarity NPC475204
0.6257 Remote Similarity NPC16188
0.6257 Remote Similarity NPC474614
0.625 Remote Similarity NPC26108
0.625 Remote Similarity NPC271942
0.6242 Remote Similarity NPC474146
0.6238 Remote Similarity NPC80514
0.6236 Remote Similarity NPC118794
0.6236 Remote Similarity NPC89341
0.6229 Remote Similarity NPC470249
0.6228 Remote Similarity NPC219444
0.6219 Remote Similarity NPC102245
0.6215 Remote Similarity NPC323123
0.6198 Remote Similarity NPC137627
0.6196 Remote Similarity NPC79844
0.6185 Remote Similarity NPC208757
0.6185 Remote Similarity NPC110800
0.618 Remote Similarity NPC66518
0.6176 Remote Similarity NPC43706
0.6175 Remote Similarity NPC56685
0.6166 Remote Similarity NPC473354
0.6165 Remote Similarity NPC473450
0.6158 Remote Similarity NPC170170
0.6158 Remote Similarity NPC476989
0.6158 Remote Similarity NPC470250
0.6158 Remote Similarity NPC219233
0.6158 Remote Similarity NPC211468
0.6158 Remote Similarity NPC294516
0.6158 Remote Similarity NPC107938
0.615 Remote Similarity NPC147847
0.615 Remote Similarity NPC37205
0.615 Remote Similarity NPC160931
0.614 Remote Similarity NPC474147
0.614 Remote Similarity NPC473708
0.6138 Remote Similarity NPC63931
0.6136 Remote Similarity NPC301050
0.6136 Remote Similarity NPC470248
0.6136 Remote Similarity NPC131204
0.6133 Remote Similarity NPC109346
0.6131 Remote Similarity NPC229213
0.6129 Remote Similarity NPC470708
0.6127 Remote Similarity NPC257390
0.6121 Remote Similarity NPC85276
0.612 Remote Similarity NPC233702
0.612 Remote Similarity NPC178097
0.6114 Remote Similarity NPC273755
0.6111 Remote Similarity NPC59387
0.6108 Remote Similarity NPC476268
0.6108 Remote Similarity NPC227976
0.6102 Remote Similarity NPC471283
0.61 Remote Similarity NPC174607
0.6095 Remote Similarity NPC473572
0.6095 Remote Similarity NPC474169
0.6094 Remote Similarity NPC46009
0.6092 Remote Similarity NPC474753
0.6087 Remote Similarity NPC202198
0.6084 Remote Similarity NPC319950
0.6082 Remote Similarity NPC471165
0.608 Remote Similarity NPC312155
0.608 Remote Similarity NPC138083
0.6074 Remote Similarity NPC115803
0.6062 Remote Similarity NPC89831
0.6051 Remote Similarity NPC50016
0.605 Remote Similarity NPC77435
0.605 Remote Similarity NPC259071
0.6041 Remote Similarity NPC32064
0.6034 Remote Similarity NPC473724
0.6033 Remote Similarity NPC476571
0.6033 Remote Similarity NPC147390
0.6033 Remote Similarity NPC428
0.6033 Remote Similarity NPC135538
0.6033 Remote Similarity NPC246587
0.6033 Remote Similarity NPC24233
0.6025 Remote Similarity NPC222084
0.6022 Remote Similarity NPC119669
0.6022 Remote Similarity NPC79076
0.6022 Remote Similarity NPC81026
0.602 Remote Similarity NPC256935
0.6019 Remote Similarity NPC24228
0.6012 Remote Similarity NPC55113
0.601 Remote Similarity NPC40234
0.601 Remote Similarity NPC21885
0.601 Remote Similarity NPC476321
0.6 Remote Similarity NPC111485
0.6 Remote Similarity NPC159767
0.6 Remote Similarity NPC469539
0.6 Remote Similarity NPC106551
0.6 Remote Similarity NPC281686
0.6 Remote Similarity NPC188867
0.6 Remote Similarity NPC469540
0.6 Remote Similarity NPC155506
0.6 Remote Similarity NPC102760
0.6 Remote Similarity NPC473402
0.6 Remote Similarity NPC476227
0.5991 Remote Similarity NPC223223
0.599 Remote Similarity NPC293624
0.599 Remote Similarity NPC45037
0.5989 Remote Similarity NPC294249
0.5988 Remote Similarity NPC134219
0.5988 Remote Similarity NPC323775
0.5988 Remote Similarity NPC236347
0.5983 Remote Similarity NPC82472
0.598 Remote Similarity NPC471526
0.598 Remote Similarity NPC474745
0.5979 Remote Similarity NPC328494
0.5979 Remote Similarity NPC230611
0.5979 Remote Similarity NPC210140
0.5979 Remote Similarity NPC147091
0.5978 Remote Similarity NPC156356
0.5978 Remote Similarity NPC473491
0.5978 Remote Similarity NPC191376
0.5978 Remote Similarity NPC321505
0.5978 Remote Similarity NPC20755
0.5978 Remote Similarity NPC179825
0.5978 Remote Similarity NPC231572
0.5977 Remote Similarity NPC120251
0.5977 Remote Similarity NPC474091
0.5976 Remote Similarity NPC142599
0.5976 Remote Similarity NPC27581
0.5976 Remote Similarity NPC142577
0.5969 Remote Similarity NPC476331
0.5969 Remote Similarity NPC205167
0.5968 Remote Similarity NPC220858
0.5968 Remote Similarity NPC151895

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC475688 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
0.6885 Remote Similarity NPD4010 Discontinued
0.6747 Remote Similarity NPD9718 Approved
0.6627 Remote Similarity NPD9569 Approved
0.6556 Remote Similarity NPD824 Approved
0.6548 Remote Similarity NPD9536 Phase 1
0.6548 Remote Similarity NPD9537 Phase 1
0.6536 Remote Similarity NPD1670 Discontinued
0.6489 Remote Similarity NPD5137 Approved
0.6471 Remote Similarity NPD259 Phase 1
0.6443 Remote Similarity NPD7281 Phase 3
0.6443 Remote Similarity NPD7280 Phase 3
0.6395 Remote Similarity NPD555 Phase 2
0.6373 Remote Similarity NPD6297 Approved
0.6369 Remote Similarity NPD258 Approved
0.6369 Remote Similarity NPD257 Approved
0.625 Remote Similarity NPD9570 Approved
0.6244 Remote Similarity NPD6851 Approved
0.6244 Remote Similarity NPD6853 Approved
0.623 Remote Similarity NPD6687 Approved
0.623 Remote Similarity NPD6688 Approved
0.6223 Remote Similarity NPD2098 Approved
0.6221 Remote Similarity NPD1329 Clinical (unspecified phase)
0.6221 Remote Similarity NPD1330 Phase 2
0.6149 Remote Similarity NPD825 Approved
0.6149 Remote Similarity NPD826 Approved
0.6129 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6127 Remote Similarity NPD598 Approved
0.6127 Remote Similarity NPD601 Approved
0.6127 Remote Similarity NPD597 Approved
0.6118 Remote Similarity NPD3055 Approved
0.6118 Remote Similarity NPD3053 Approved
0.6117 Remote Similarity NPD2097 Approved
0.6114 Remote Similarity NPD275 Approved
0.6114 Remote Similarity NPD274 Approved
0.6105 Remote Similarity NPD8303 Discontinued
0.6094 Remote Similarity NPD4652 Approved
0.6092 Remote Similarity NPD1130 Approved
0.6092 Remote Similarity NPD1132 Approved
0.6092 Remote Similarity NPD1136 Approved
0.6067 Remote Similarity NPD1632 Clinical (unspecified phase)
0.6059 Remote Similarity NPD5165 Clinical (unspecified phase)
0.6059 Remote Similarity NPD3125 Approved
0.6049 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6045 Remote Similarity NPD743 Approved
0.6 Remote Similarity NPD9568 Approved
0.5989 Remote Similarity NPD817 Approved
0.5989 Remote Similarity NPD823 Approved
0.5988 Remote Similarity NPD9619 Approved
0.5988 Remote Similarity NPD9620 Approved
0.5988 Remote Similarity NPD9621 Approved
0.598 Remote Similarity NPD7132 Clinical (unspecified phase)
0.5966 Remote Similarity NPD3061 Approved
0.5966 Remote Similarity NPD3059 Approved
0.5966 Remote Similarity NPD3062 Approved
0.5965 Remote Similarity NPD5310 Approved
0.5965 Remote Similarity NPD5311 Approved
0.5965 Remote Similarity NPD9634 Clinical (unspecified phase)
0.5961 Remote Similarity NPD6377 Clinical (unspecified phase)
0.5956 Remote Similarity NPD6884 Clinical (unspecified phase)
0.5956 Remote Similarity NPD3845 Phase 1
0.5951 Remote Similarity NPD9377 Approved
0.5951 Remote Similarity NPD9379 Approved
0.5939 Remote Similarity NPD5313 Approved
0.5939 Remote Similarity NPD5312 Approved
0.5938 Remote Similarity NPD8245 Clinical (unspecified phase)
0.5928 Remote Similarity NPD4166 Phase 2
0.5928 Remote Similarity NPD1293 Approved
0.5924 Remote Similarity NPD2421 Approved
0.5924 Remote Similarity NPD2420 Approved
0.5904 Remote Similarity NPD1337 Clinical (unspecified phase)
0.5899 Remote Similarity NPD5314 Approved
0.5885 Remote Similarity NPD8095 Phase 1
0.587 Remote Similarity NPD2422 Clinical (unspecified phase)
0.5855 Remote Similarity NPD1168 Approved
0.5854 Remote Similarity NPD5525 Clinical (unspecified phase)
0.5851 Remote Similarity NPD3455 Phase 2
0.5848 Remote Similarity NPD2337 Clinical (unspecified phase)
0.5846 Remote Similarity NPD1161 Approved
0.5825 Remote Similarity NPD2041 Clinical (unspecified phase)
0.5825 Remote Similarity NPD2042 Clinical (unspecified phase)
0.5814 Remote Similarity NPD9622 Approved
0.5814 Remote Similarity NPD1421 Approved
0.5814 Remote Similarity NPD1420 Approved
0.5795 Remote Similarity NPD2017 Approved
0.5795 Remote Similarity NPD2889 Approved
0.5795 Remote Similarity NPD2890 Approved
0.5795 Remote Similarity NPD2888 Approved
0.5795 Remote Similarity NPD6107 Approved
0.5789 Remote Similarity NPD4762 Approved
0.5789 Remote Similarity NPD4761 Approved
0.5784 Remote Similarity NPD3141 Discontinued
0.5767 Remote Similarity NPD746 Clinical (unspecified phase)
0.5765 Remote Similarity NPD9381 Approved
0.5765 Remote Similarity NPD9384 Approved
0.5763 Remote Similarity NPD3145 Approved
0.5763 Remote Similarity NPD2078 Clinical (unspecified phase)
0.5763 Remote Similarity NPD8398 Clinical (unspecified phase)
0.5763 Remote Similarity NPD2028 Clinical (unspecified phase)
0.5763 Remote Similarity NPD3144 Approved
0.5756 Remote Similarity NPD3073 Approved
0.5756 Remote Similarity NPD3072 Approved
0.5756 Remote Similarity NPD3071 Approved
0.5749 Remote Similarity NPD255 Approved
0.5749 Remote Similarity NPD256 Approved
0.5745 Remote Similarity NPD3639 Approved
0.5745 Remote Similarity NPD3641 Approved
0.5745 Remote Similarity NPD3640 Phase 3
0.5739 Remote Similarity NPD4207 Discontinued
0.573 Remote Similarity NPD2674 Phase 3
0.5729 Remote Similarity NPD2978 Approved
0.5729 Remote Similarity NPD2977 Approved
0.5723 Remote Similarity NPD1755 Approved
0.5722 Remote Similarity NPD2492 Phase 1
0.5714 Remote Similarity NPD4210 Discontinued
0.5707 Remote Similarity NPD2898 Approved
0.5706 Remote Similarity NPD3136 Phase 2
0.5694 Remote Similarity NPD4413 Clinical (unspecified phase)
0.5691 Remote Similarity NPD2183 Approved
0.5691 Remote Similarity NPD2184 Approved
0.5663 Remote Similarity NPD2904 Discontinued
0.5663 Remote Similarity NPD5677 Discontinued
0.5661 Remote Similarity NPD6662 Clinical (unspecified phase)
0.5659 Remote Similarity NPD1169 Approved
0.5652 Remote Similarity NPD4664 Clinical (unspecified phase)
0.5652 Remote Similarity NPD9244 Approved
0.5647 Remote Similarity NPD316 Approved
0.5645 Remote Similarity NPD302 Approved
0.5642 Remote Similarity NPD5745 Approved
0.564 Remote Similarity NPD5564 Approved
0.5638 Remote Similarity NPD3146 Approved
0.5638 Remote Similarity NPD3688 Clinical (unspecified phase)
0.5638 Remote Similarity NPD1754 Clinical (unspecified phase)
0.5632 Remote Similarity NPD3686 Approved
0.5632 Remote Similarity NPD3687 Approved
0.5622 Remote Similarity NPD4237 Approved
0.5622 Remote Similarity NPD4236 Phase 3
0.561 Remote Similarity NPD5946 Clinical (unspecified phase)
0.5607 Remote Similarity NPD4706 Clinical (unspecified phase)
0.56 Remote Similarity NPD5200 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   11338800
ChEMBL   CHEMBL511678
ZINC  

Physicochemical Properties

Molecular Weight:  406.90
ALogP:  -0.4163
MLogP:  1.9
XLogP:  0.961
# Rotatable Bonds:  8
Polar Surface Area:  98.07
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  20

Download Data

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Biological Activities  
Similar NPs/Drugs