Natural Product: NPC230539

Natural Product ID:  NPC230539
Common Name:   Amathaspiramide B
IUPAC Name:   (5S,8R,9R)-9-(2,4-dibromo-5-methoxyphenyl)-8-hydroxy-1,7-dimethyl-1,7-diazaspiro[4.4]nonane-2,6-dione
Synonyms:  
Molecular Formula:   C16H18Br2N2O4
Standard InCHIKey:  MLOALGRVDHEDCC-LZWOXQAQSA-N
Standard InCHI:  InChI=1S/C16H18Br2N2O4/c1-19-14(22)13(8-6-11(24-3)10(18)7-9(8)17)16(15(19)23)5-4-12(21)20(16)2/h6-7,13-14,22H,4-5H2,1-3H3/t13-,14+,16-/m0/s1
Canonical SMILES:  COc1cc(c(cc1Br)Br)[C@H]1[C@@H](O)N(C(=O)[C@@]21CCC(=O)N2C)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
NPO3299 Amathia wilsoni Species Vesiculariidae Eukaryota PMID[10346946]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT168 Cell Line P388 Mus musculus IC50 > 12.5 ug/ml 24900468

  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 NPC230539 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
0.9881 High Similarity NPC80337
0.9538 High Similarity NPC64066
0.9096 High Similarity NPC102245
0.731 Intermediate Similarity NPC470248
0.7225 Intermediate Similarity NPC470250
0.7209 Intermediate Similarity NPC470249
0.7052 Intermediate Similarity NPC235633
0.6866 Remote Similarity NPC473941
0.6853 Remote Similarity NPC102760
0.6834 Remote Similarity NPC147847
0.6816 Remote Similarity NPC470247
0.6798 Remote Similarity NPC470709
0.6784 Remote Similarity NPC174607
0.6782 Remote Similarity NPC227953
0.6766 Remote Similarity NPC248822
0.6763 Remote Similarity NPC135173
0.6754 Remote Similarity NPC469505
0.6751 Remote Similarity NPC167763
0.6751 Remote Similarity NPC470903
0.6751 Remote Similarity NPC470112
0.6737 Remote Similarity NPC469479
0.6735 Remote Similarity NPC475120
0.6734 Remote Similarity NPC259071
0.6734 Remote Similarity NPC77435
0.6722 Remote Similarity NPC308571
0.6703 Remote Similarity NPC469711
0.67 Remote Similarity NPC474678
0.67 Remote Similarity NPC471338
0.6684 Remote Similarity NPC472923
0.6667 Remote Similarity NPC475843
0.6667 Remote Similarity NPC471337
0.665 Remote Similarity NPC204970
0.663 Remote Similarity NPC324081
0.6615 Remote Similarity NPC475688
0.6599 Remote Similarity NPC475421
0.6598 Remote Similarity NPC477255
0.6587 Remote Similarity NPC473450
0.6585 Remote Similarity NPC202866
0.6576 Remote Similarity NPC296085
0.6567 Remote Similarity NPC8093
0.6567 Remote Similarity NPC121571
0.6559 Remote Similarity NPC262166
0.655 Remote Similarity NPC477254
0.6505 Remote Similarity NPC59827
0.6505 Remote Similarity NPC184933
0.6502 Remote Similarity NPC230098
0.65 Remote Similarity NPC99723
0.6488 Remote Similarity NPC319549
0.6486 Remote Similarity NPC71629
0.6473 Remote Similarity NPC33256
0.6471 Remote Similarity NPC283207
0.6464 Remote Similarity NPC40321
0.6456 Remote Similarity NPC94499
0.6453 Remote Similarity NPC4910
0.6444 Remote Similarity NPC106606
0.6436 Remote Similarity NPC299806
0.6422 Remote Similarity NPC246591
0.6418 Remote Similarity NPC474745
0.6411 Remote Similarity NPC477527
0.6392 Remote Similarity NPC254700
0.6387 Remote Similarity NPC319320
0.6387 Remote Similarity NPC287757
0.6383 Remote Similarity NPC56685
0.6383 Remote Similarity NPC258222
0.6378 Remote Similarity NPC476002
0.6374 Remote Similarity NPC128877
0.6373 Remote Similarity NPC329731
0.6372 Remote Similarity NPC470746
0.6372 Remote Similarity NPC471336
0.6368 Remote Similarity NPC474325
0.6364 Remote Similarity NPC164608
0.635 Remote Similarity NPC304675
0.6345 Remote Similarity NPC100566
0.6345 Remote Similarity NPC328494
0.6343 Remote Similarity NPC110131
0.6341 Remote Similarity NPC162694
0.6333 Remote Similarity NPC293624
0.633 Remote Similarity NPC214239
0.6324 Remote Similarity NPC475981
0.6324 Remote Similarity NPC474746
0.6324 Remote Similarity NPC276120
0.6319 Remote Similarity NPC194359
0.6319 Remote Similarity NPC474673
0.6319 Remote Similarity NPC28641
0.6318 Remote Similarity NPC237044
0.6318 Remote Similarity NPC35680
0.6311 Remote Similarity NPC64140
0.6311 Remote Similarity NPC174122
0.6311 Remote Similarity NPC174629
0.6298 Remote Similarity NPC65714
0.6296 Remote Similarity NPC261934
0.6296 Remote Similarity NPC202198
0.6296 Remote Similarity NPC5194
0.6293 Remote Similarity NPC96275
0.6281 Remote Similarity NPC474708
0.6279 Remote Similarity NPC195787
0.6279 Remote Similarity NPC246140
0.6276 Remote Similarity NPC473502
0.6276 Remote Similarity NPC320104
0.6274 Remote Similarity NPC123140
0.6269 Remote Similarity NPC133817
0.6269 Remote Similarity NPC476443
0.6268 Remote Similarity NPC80514
0.6263 Remote Similarity NPC47672
0.6263 Remote Similarity NPC181653
0.6263 Remote Similarity NPC68967
0.6263 Remote Similarity NPC190332
0.6262 Remote Similarity NPC234069
0.6257 Remote Similarity NPC189908
0.6256 Remote Similarity NPC165797
0.6256 Remote Similarity NPC249274
0.6256 Remote Similarity NPC4304
0.6256 Remote Similarity NPC205167
0.625 Remote Similarity NPC251439
0.6244 Remote Similarity NPC234772
0.6239 Remote Similarity NPC122886
0.6238 Remote Similarity NPC474470
0.6238 Remote Similarity NPC149962
0.6238 Remote Similarity NPC308709
0.6238 Remote Similarity NPC32064
0.6233 Remote Similarity NPC477666
0.6232 Remote Similarity NPC29531
0.6231 Remote Similarity NPC266176
0.6231 Remote Similarity NPC82533
0.6231 Remote Similarity NPC158148
0.6231 Remote Similarity NPC475845
0.6231 Remote Similarity NPC290759
0.6228 Remote Similarity NPC74216
0.6226 Remote Similarity NPC123859
0.6222 Remote Similarity NPC71539
0.6222 Remote Similarity NPC250960
0.6219 Remote Similarity NPC475976
0.6215 Remote Similarity NPC475747
0.6215 Remote Similarity NPC286135
0.6211 Remote Similarity NPC226514
0.6211 Remote Similarity NPC109968
0.6209 Remote Similarity NPC144314
0.6209 Remote Similarity NPC109580
0.6209 Remote Similarity NPC471592
0.6205 Remote Similarity NPC10653
0.6205 Remote Similarity NPC318525
0.6205 Remote Similarity NPC59028
0.6205 Remote Similarity NPC475697
0.6205 Remote Similarity NPC92191
0.6204 Remote Similarity NPC80472
0.6203 Remote Similarity NPC16188
0.6201 Remote Similarity NPC195902
0.62 Remote Similarity NPC476227
0.62 Remote Similarity NPC26108
0.6197 Remote Similarity NPC242728
0.6197 Remote Similarity NPC138830
0.6195 Remote Similarity NPC206061
0.6195 Remote Similarity NPC138083
0.6193 Remote Similarity NPC218614
0.6193 Remote Similarity NPC302597
0.619 Remote Similarity NPC471563
0.6181 Remote Similarity NPC474324
0.6181 Remote Similarity NPC57812
0.6181 Remote Similarity NPC252960
0.6181 Remote Similarity NPC298186
0.6181 Remote Similarity NPC301189
0.618 Remote Similarity NPC280736
0.6179 Remote Similarity NPC50548
0.6179 Remote Similarity NPC100863
0.6172 Remote Similarity NPC196231
0.6171 Remote Similarity NPC471335
0.617 Remote Similarity NPC9373
0.6169 Remote Similarity NPC470739
0.6169 Remote Similarity NPC225597
0.6169 Remote Similarity NPC477640
0.6167 Remote Similarity NPC257390
0.6166 Remote Similarity NPC233926
0.6166 Remote Similarity NPC156311
0.6162 Remote Similarity NPC186617
0.6162 Remote Similarity NPC231198
0.6161 Remote Similarity NPC470646
0.6157 Remote Similarity NPC470484
0.6154 Remote Similarity NPC474811
0.6154 Remote Similarity NPC118099
0.6154 Remote Similarity NPC241794
0.6154 Remote Similarity NPC151706
0.6154 Remote Similarity NPC474855
0.6154 Remote Similarity NPC9687
0.6154 Remote Similarity NPC141440
0.6154 Remote Similarity NPC293377
0.6154 Remote Similarity NPC79465
0.6154 Remote Similarity NPC475598
0.6154 Remote Similarity NPC260045
0.6154 Remote Similarity NPC474787
0.6154 Remote Similarity NPC90194
0.6154 Remote Similarity NPC76785
0.6154 Remote Similarity NPC474535
0.6154 Remote Similarity NPC475318
0.6154 Remote Similarity NPC273907
0.6154 Remote Similarity NPC476102
0.6154 Remote Similarity NPC49577
0.615 Remote Similarity NPC135349
0.615 Remote Similarity NPC58766
0.615 Remote Similarity NPC79076
0.615 Remote Similarity NPC267414

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC230539 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
0.7062 Intermediate Similarity NPD7280 Phase 3
0.7062 Intermediate Similarity NPD7281 Phase 3
0.6828 Remote Similarity NPD7248 Discontinued
0.6596 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6595 Remote Similarity NPD2184 Approved
0.6595 Remote Similarity NPD2183 Approved
0.6579 Remote Similarity NPD5967 Approved
0.6513 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6497 Remote Similarity NPD2245 Discovery
0.6488 Remote Similarity NPD7296 Approved
0.6484 Remote Similarity NPD3655 Clinical (unspecified phase)
0.6462 Remote Similarity NPD4010 Discontinued
0.6462 Remote Similarity NPD4166 Phase 2
0.6436 Remote Similarity NPD4210 Discontinued
0.6422 Remote Similarity NPD6040 Clinical (unspecified phase)
0.64 Remote Similarity NPD6297 Approved
0.6383 Remote Similarity NPD1670 Discontinued
0.6382 Remote Similarity NPD5313 Approved
0.6382 Remote Similarity NPD5312 Approved
0.6368 Remote Similarity NPD6875 Approved
0.6368 Remote Similarity NPD6876 Approved
0.6364 Remote Similarity NPD3158 Phase 1
0.6364 Remote Similarity NPD3157 Approved
0.6359 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6359 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6355 Remote Similarity NPD6851 Approved
0.6355 Remote Similarity NPD7090 Clinical (unspecified phase)
0.6355 Remote Similarity NPD6853 Approved
0.6345 Remote Similarity NPD5137 Approved
0.6337 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6296 Remote Similarity NPD7131 Phase 3
0.6296 Remote Similarity NPD6662 Clinical (unspecified phase)
0.6287 Remote Similarity NPD1298 Discontinued
0.6278 Remote Similarity NPD2238 Phase 2
0.6269 Remote Similarity NPD5773 Approved
0.6269 Remote Similarity NPD6668 Clinical (unspecified phase)
0.6269 Remote Similarity NPD5772 Approved
0.625 Remote Similarity NPD5165 Clinical (unspecified phase)
0.625 Remote Similarity NPD7109 Clinical (unspecified phase)
0.625 Remote Similarity NPD7110 Phase 1
0.6238 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6211 Remote Similarity NPD5586 Clinical (unspecified phase)
0.6183 Remote Similarity NPD4236 Phase 3
0.6183 Remote Similarity NPD4237 Approved
0.6181 Remote Similarity NPD6687 Approved
0.6181 Remote Similarity NPD6688 Approved
0.6176 Remote Similarity NPD4419 Clinical (unspecified phase)
0.617 Remote Similarity NPD6666 Approved
0.617 Remote Similarity NPD6667 Approved
0.615 Remote Similarity NPD7810 Phase 3
0.615 Remote Similarity NPD5754 Discontinued
0.615 Remote Similarity NPD7811 Phase 3
0.6138 Remote Similarity NPD5297 Approved
0.6133 Remote Similarity NPD5745 Approved
0.6126 Remote Similarity NPD3641 Approved
0.6126 Remote Similarity NPD3639 Approved
0.6126 Remote Similarity NPD3640 Phase 3
0.6111 Remote Similarity NPD2041 Clinical (unspecified phase)
0.6111 Remote Similarity NPD2042 Clinical (unspecified phase)
0.6096 Remote Similarity NPD6860 Clinical (unspecified phase)
0.6092 Remote Similarity NPD2667 Approved
0.6092 Remote Similarity NPD2668 Approved
0.6089 Remote Similarity NPD2040 Clinical (unspecified phase)
0.6089 Remote Similarity NPD7177 Discontinued
0.6087 Remote Similarity NPD743 Approved
0.608 Remote Similarity NPD2233 Approved
0.608 Remote Similarity NPD7485 Phase 3
0.608 Remote Similarity NPD7484 Phase 3
0.608 Remote Similarity NPD2232 Approved
0.608 Remote Similarity NPD2230 Approved
0.6075 Remote Similarity NPD8095 Phase 1
0.6068 Remote Similarity NPD3337 Discontinued
0.6067 Remote Similarity NPD8398 Clinical (unspecified phase)
0.6062 Remote Similarity NPD824 Approved
0.6061 Remote Similarity NPD8245 Clinical (unspecified phase)
0.6061 Remote Similarity NPD6315 Phase 2
0.6059 Remote Similarity NPD3050 Clinical (unspecified phase)
0.6055 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6034 Remote Similarity NPD7432 Phase 2
0.6032 Remote Similarity NPD2219 Phase 1
0.6029 Remote Similarity NPD4157 Discontinued
0.6022 Remote Similarity NPD5746 Approved
0.6021 Remote Similarity NPD7020 Approved
0.6021 Remote Similarity NPD7019 Approved
0.6011 Remote Similarity NPD2654 Approved
0.6009 Remote Similarity NPD4040 Phase 1
0.6 Remote Similarity NPD6385 Approved
0.6 Remote Similarity NPD6386 Approved
0.599 Remote Similarity NPD2968 Approved
0.599 Remote Similarity NPD5616 Clinical (unspecified phase)
0.599 Remote Similarity NPD2971 Approved
0.599 Remote Similarity NPD7613 Discontinued
0.599 Remote Similarity NPD4078 Clinical (unspecified phase)
0.5981 Remote Similarity NPD2974 Approved
0.5981 Remote Similarity NPD2973 Approved
0.5981 Remote Similarity NPD2975 Approved
0.5981 Remote Similarity NPD5564 Approved
0.598 Remote Similarity NPD6042 Phase 2
0.598 Remote Similarity NPD42 Phase 2
0.5972 Remote Similarity NPD2490 Approved
0.5972 Remote Similarity NPD4580 Approved
0.5972 Remote Similarity NPD6505 Approved
0.5972 Remote Similarity NPD6504 Approved
0.5972 Remote Similarity NPD2488 Approved
0.597 Remote Similarity NPD7315 Approved
0.597 Remote Similarity NPD3051 Approved
0.5969 Remote Similarity NPD4227 Discontinued
0.5969 Remote Similarity NPD7837 Clinical (unspecified phase)
0.5962 Remote Similarity NPD6618 Phase 2
0.5956 Remote Similarity NPD7086 Phase 2
0.5955 Remote Similarity NPD1421 Approved
0.5955 Remote Similarity NPD1420 Approved
0.5951 Remote Similarity NPD5484 Approved
0.5951 Remote Similarity NPD5485 Approved
0.5947 Remote Similarity NPD7910 Clinical (unspecified phase)
0.5947 Remote Similarity NPD3692 Discontinued
0.5946 Remote Similarity NPD8172 Phase 2
0.5946 Remote Similarity NPD8173 Phase 2
0.5946 Remote Similarity NPD4579 Clinical (unspecified phase)
0.5944 Remote Similarity NPD7905 Discontinued
0.5941 Remote Similarity NPD2969 Approved
0.5941 Remote Similarity NPD2970 Approved
0.5939 Remote Similarity NPD6818 Clinical (unspecified phase)
0.5938 Remote Similarity NPD3688 Clinical (unspecified phase)
0.5938 Remote Similarity NPD3146 Approved
0.5934 Remote Similarity NPD2669 Clinical (unspecified phase)
0.5931 Remote Similarity NPD6620 Discovery
0.592 Remote Similarity NPD2516 Approved
0.592 Remote Similarity NPD6107 Approved
0.5918 Remote Similarity NPD4772 Phase 2
0.5918 Remote Similarity NPD4773 Phase 2
0.5918 Remote Similarity NPD4424 Discontinued
0.5917 Remote Similarity NPD6863 Phase 2
0.5916 Remote Similarity NPD6884 Clinical (unspecified phase)
0.5911 Remote Similarity NPD3451 Clinical (unspecified phase)
0.5909 Remote Similarity NPD2560 Approved
0.5909 Remote Similarity NPD8161 Suspended
0.5909 Remote Similarity NPD2563 Approved
0.5899 Remote Similarity NPD7501 Clinical (unspecified phase)
0.5897 Remote Similarity NPD6591 Clinical (unspecified phase)
0.5893 Remote Similarity NPD7827 Phase 1
0.5891 Remote Similarity NPD6071 Discontinued
0.5891 Remote Similarity NPD2517 Approved
0.5891 Remote Similarity NPD7608 Discontinued
0.5889 Remote Similarity NPD1318 Phase 2
0.5888 Remote Similarity NPD7669 Phase 3
0.5888 Remote Similarity NPD6844 Discontinued
0.588 Remote Similarity NPD4420 Approved
0.5874 Remote Similarity NPD5557 Phase 1
0.5874 Remote Similarity NPD4956 Approved
0.5872 Remote Similarity NPD2494 Approved
0.5872 Remote Similarity NPD2493 Approved
0.5871 Remote Similarity NPD2904 Discontinued
0.587 Remote Similarity NPD6997 Phase 2
0.5864 Remote Similarity NPD4583 Approved
0.5864 Remote Similarity NPD5241 Discontinued
0.5864 Remote Similarity NPD4582 Approved
0.586 Remote Similarity NPD4362 Clinical (unspecified phase)
0.586 Remote Similarity NPD5582 Discontinued
0.586 Remote Similarity NPD5725 Approved
0.586 Remote Similarity NPD4361 Phase 2
0.5855 Remote Similarity NPD1754 Clinical (unspecified phase)
0.5851 Remote Similarity NPD6032 Approved
0.585 Remote Similarity NPD6533 Clinical (unspecified phase)
0.5849 Remote Similarity NPD6377 Clinical (unspecified phase)
0.5847 Remote Similarity NPD9718 Approved
0.5846 Remote Similarity NPD3686 Approved
0.5846 Remote Similarity NPD3687 Approved
0.5845 Remote Similarity NPD5006 Approved
0.5845 Remote Similarity NPD5005 Approved
0.5845 Remote Similarity NPD3057 Approved
0.5842 Remote Similarity NPD3060 Approved
0.5838 Remote Similarity NPD7193 Clinical (unspecified phase)
0.5833 Remote Similarity NPD2489 Approved
0.5833 Remote Similarity NPD7124 Phase 2
0.5833 Remote Similarity NPD6894 Phase 1
0.5833 Remote Similarity NPD4481 Phase 3
0.5833 Remote Similarity NPD27 Approved
0.5829 Remote Similarity NPD6896 Approved
0.5829 Remote Similarity NPD4434 Approved
0.5829 Remote Similarity NPD6895 Approved
0.5825 Remote Similarity NPD6390 Discontinued
0.5824 Remote Similarity NPD4177 Approved
0.5824 Remote Similarity NPD4175 Approved
0.5818 Remote Similarity NPD4004 Approved
0.5818 Remote Similarity NPD4002 Approved
0.5817 Remote Similarity NPD5039 Approved
0.5817 Remote Similarity NPD7038 Approved
0.5817 Remote Similarity NPD7039 Approved
0.5816 Remote Similarity NPD2651 Approved
0.5816 Remote Similarity NPD2649 Approved
0.5815 Remote Similarity NPD5718 Phase 2
0.5808 Remote Similarity NPD5355 Approved
0.5808 Remote Similarity NPD5356 Approved
0.5805 Remote Similarity NPD6720 Clinical (unspecified phase)
0.5802 Remote Similarity NPD7243 Clinical (unspecified phase)
0.5802 Remote Similarity NPD7291 Discontinued
0.5802 Remote Similarity NPD4435 Approved
0.5801 Remote Similarity NPD4098 Discontinued
0.5799 Remote Similarity NPD3450 Approved

Structure

External Identifiers

PubChem CID   10671715
ChEMBL   CHEMBL491701
ZINC  

Physicochemical Properties

Molecular Weight:  459.96
ALogP:  0.0321
MLogP:  2.34
XLogP:  1.12
# Rotatable Bonds:  8
Polar Surface Area:  70.08
# H-Bond Aceptor:  5
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  24

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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