Natural Product: NPC259071

Natural Product ID:  NPC259071
Common Name:   Araplysillin I
IUPAC Name:   (5S,6R)-N-[3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl]-7,9-dibromo-6-hydroxy-8-methoxy-1-oxa-2-azaspiro[4.5]deca-2,7,9-triene-3-carboxamide
Synonyms:   Araplysillin I
Molecular Formula:   C21H23Br4N3O5
Standard InCHIKey:  DJOILUOUAWXGIG-PZJWPPBQSA-N
Standard InCHI:  InChI=1S/C21H23Br4N3O5/c1-31-18-14(24)9-21(19(29)16(18)25)10-15(28-33-21)20(30)27-5-2-6-32-17-12(22)7-11(3-4-26)8-13(17)23/h7-9,19,29H,2-6,10,26H2,1H3,(H,27,30)/t19-,21+/m0/s1
Canonical SMILES:  NCCc1cc(Br)c(c(c1)Br)OCCCNC(=O)C1=NO[C@@]2(C1)C=C(Br)C(=C([C@@H]2O)Br)OC
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
NPO32712 suberea ianthelliformis Species Aplysinellidae Eukaryota PMID[22515429]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1548 Organism Pseudomonas aeruginosa PAO1 Pseudomonas aeruginosa PAO1 Inhibition = 65 % 17482821
NPT16 Organism Staphylococcus aureus Staphylococcus aureus Inhibition = 60 % 22037378

  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 NPC259071 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 NPC77435
0.9649 High Similarity NPC227953
0.9593 High Similarity NPC202866
0.9471 High Similarity NPC174607
0.9415 High Similarity NPC147847
0.9075 High Similarity NPC8093
0.9075 High Similarity NPC121571
0.8876 High Similarity NPC474678
0.8876 High Similarity NPC477255
0.8876 High Similarity NPC471338
0.8827 High Similarity NPC475843
0.8636 High Similarity NPC477254
0.8587 High Similarity NPC471337
0.8486 Intermediate Similarity NPC123140
0.8272 Intermediate Similarity NPC471336
0.8272 Intermediate Similarity NPC470746
0.8177 Intermediate Similarity NPC471339
0.798 Intermediate Similarity NPC471335
0.7965 Intermediate Similarity NPC156311
0.7791 Intermediate Similarity NPC469711
0.7674 Intermediate Similarity NPC76412
0.7665 Intermediate Similarity NPC128877
0.7633 Intermediate Similarity NPC308571
0.763 Intermediate Similarity NPC258222
0.7586 Intermediate Similarity NPC47672
0.7557 Intermediate Similarity NPC233926
0.7529 Intermediate Similarity NPC109968
0.7487 Intermediate Similarity NPC248822
0.7485 Intermediate Similarity NPC78530
0.7384 Intermediate Similarity NPC135349
0.7356 Intermediate Similarity NPC71629
0.7294 Intermediate Similarity NPC474673
0.7292 Intermediate Similarity NPC246591
0.7283 Intermediate Similarity NPC470472
0.7278 Intermediate Similarity NPC470471
0.7273 Intermediate Similarity NPC473450
0.7257 Intermediate Similarity NPC296085
0.7193 Intermediate Similarity NPC470470
0.7168 Intermediate Similarity NPC474128
0.7107 Intermediate Similarity NPC80514
0.7091 Intermediate Similarity NPC272463
0.7062 Intermediate Similarity NPC96275
0.7048 Intermediate Similarity NPC110131
0.7005 Intermediate Similarity NPC102245
0.7 Intermediate Similarity NPC143450
0.6919 Remote Similarity NPC64066
0.6888 Remote Similarity NPC473892
0.6888 Remote Similarity NPC471591
0.6888 Remote Similarity NPC475658
0.6853 Remote Similarity NPC473409
0.6853 Remote Similarity NPC82741
0.6853 Remote Similarity NPC141405
0.6823 Remote Similarity NPC226001
0.6818 Remote Similarity NPC283207
0.6802 Remote Similarity NPC247018
0.6802 Remote Similarity NPC307123
0.6802 Remote Similarity NPC97870
0.68 Remote Similarity NPC65714
0.6788 Remote Similarity NPC207819
0.6788 Remote Similarity NPC473462
0.6788 Remote Similarity NPC298981
0.6788 Remote Similarity NPC126128
0.6788 Remote Similarity NPC110454
0.6751 Remote Similarity NPC49172
0.6736 Remote Similarity NPC469979
0.6734 Remote Similarity NPC230539
0.6718 Remote Similarity NPC475396
0.6717 Remote Similarity NPC80337
0.67 Remote Similarity NPC471592
0.6686 Remote Similarity NPC474087
0.6684 Remote Similarity NPC74618
0.6684 Remote Similarity NPC225130
0.6684 Remote Similarity NPC301941
0.6684 Remote Similarity NPC214188
0.6683 Remote Similarity NPC469721
0.6667 Remote Similarity NPC254700
0.6648 Remote Similarity NPC20755
0.6647 Remote Similarity NPC475735
0.6647 Remote Similarity NPC473724
0.6618 Remote Similarity NPC469731
0.6616 Remote Similarity NPC138083
0.661 Remote Similarity NPC213471
0.659 Remote Similarity NPC474091
0.6582 Remote Similarity NPC290534
0.6571 Remote Similarity NPC169766
0.6571 Remote Similarity NPC132308
0.657 Remote Similarity NPC477220
0.6557 Remote Similarity NPC324081
0.6555 Remote Similarity NPC81845
0.655 Remote Similarity NPC144823
0.6514 Remote Similarity NPC474753
0.6505 Remote Similarity NPC235033
0.6505 Remote Similarity NPC73132
0.6505 Remote Similarity NPC476268
0.6505 Remote Similarity NPC471235
0.65 Remote Similarity NPC204546
0.65 Remote Similarity NPC276120
0.6497 Remote Similarity NPC235633
0.6492 Remote Similarity NPC469479
0.6491 Remote Similarity NPC158672
0.6491 Remote Similarity NPC1702
0.648 Remote Similarity NPC40321
0.6461 Remote Similarity NPC470248
0.6461 Remote Similarity NPC470249
0.6453 Remote Similarity NPC320242
0.645 Remote Similarity NPC66855
0.645 Remote Similarity NPC299806
0.645 Remote Similarity NPC315542
0.6443 Remote Similarity NPC89831
0.6441 Remote Similarity NPC303993
0.6425 Remote Similarity NPC280022
0.6425 Remote Similarity NPC197045
0.642 Remote Similarity NPC470392
0.6414 Remote Similarity NPC32064
0.6406 Remote Similarity NPC67658
0.6404 Remote Similarity NPC196708
0.6402 Remote Similarity NPC295795
0.6402 Remote Similarity NPC319320
0.6402 Remote Similarity NPC287757
0.64 Remote Similarity NPC135173
0.6392 Remote Similarity NPC196091
0.6392 Remote Similarity NPC475123
0.6392 Remote Similarity NPC475204
0.6392 Remote Similarity NPC471568
0.6392 Remote Similarity NPC473693
0.6392 Remote Similarity NPC46009
0.6389 Remote Similarity NPC470886
0.6378 Remote Similarity NPC164608
0.6378 Remote Similarity NPC471165
0.6374 Remote Similarity NPC116562
0.6374 Remote Similarity NPC313173
0.6364 Remote Similarity NPC242728
0.6364 Remote Similarity NPC11449
0.6355 Remote Similarity NPC124626
0.6354 Remote Similarity NPC470709
0.6349 Remote Similarity NPC56635
0.6345 Remote Similarity NPC50016
0.634 Remote Similarity NPC186617
0.634 Remote Similarity NPC469505
0.6333 Remote Similarity NPC473262
0.6333 Remote Similarity NPC300912
0.6333 Remote Similarity NPC202166
0.6333 Remote Similarity NPC473261
0.633 Remote Similarity NPC256689
0.633 Remote Similarity NPC470710
0.633 Remote Similarity NPC123011
0.6327 Remote Similarity NPC273755
0.6325 Remote Similarity NPC115803
0.6324 Remote Similarity NPC132771
0.6324 Remote Similarity NPC64140
0.6324 Remote Similarity NPC174122
0.6321 Remote Similarity NPC14339
0.6305 Remote Similarity NPC94862
0.6301 Remote Similarity NPC260270
0.6296 Remote Similarity NPC92235
0.6293 Remote Similarity NPC473378
0.6293 Remote Similarity NPC473407
0.6289 Remote Similarity NPC473502
0.6287 Remote Similarity NPC206061
0.6286 Remote Similarity NPC477551
0.6281 Remote Similarity NPC119652
0.6281 Remote Similarity NPC97526
0.6281 Remote Similarity NPC475615
0.6278 Remote Similarity NPC309667
0.6278 Remote Similarity NPC106606
0.6275 Remote Similarity NPC470951
0.6275 Remote Similarity NPC234069
0.627 Remote Similarity NPC313414
0.627 Remote Similarity NPC9373
0.6269 Remote Similarity NPC158900
0.6269 Remote Similarity NPC63931
0.6269 Remote Similarity NPC472923
0.6268 Remote Similarity NPC477550
0.6268 Remote Similarity NPC477552
0.6264 Remote Similarity NPC136112
0.6264 Remote Similarity NPC141739
0.6262 Remote Similarity NPC79130
0.6256 Remote Similarity NPC156055
0.625 Remote Similarity NPC283079
0.625 Remote Similarity NPC308709
0.625 Remote Similarity NPC197125
0.6244 Remote Similarity NPC240130
0.6244 Remote Similarity NPC61332
0.6244 Remote Similarity NPC306804
0.6243 Remote Similarity NPC145149
0.6233 Remote Similarity NPC243633
0.6233 Remote Similarity NPC175150
0.6229 Remote Similarity NPC218323
0.6225 Remote Similarity NPC4910
0.6224 Remote Similarity NPC40234
0.6223 Remote Similarity NPC56685
0.622 Remote Similarity NPC144314
0.6219 Remote Similarity NPC473404
0.6218 Remote Similarity NPC67080
0.6216 Remote Similarity NPC119569
0.6215 Remote Similarity NPC99280
0.6212 Remote Similarity NPC26108
0.6212 Remote Similarity NPC473354
0.6209 Remote Similarity NPC470250
0.6207 Remote Similarity NPC235194

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC259071 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
0.6979 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6802 Remote Similarity NPD1423 Approved
0.6761 Remote Similarity NPD2240 Approved
0.6761 Remote Similarity NPD2239 Approved
0.675 Remote Similarity NPD5165 Clinical (unspecified phase)
0.6742 Remote Similarity NPD2976 Clinical (unspecified phase)
0.6684 Remote Similarity NPD7485 Phase 3
0.6684 Remote Similarity NPD7484 Phase 3
0.6667 Remote Similarity NPD7131 Phase 3
0.6573 Remote Similarity NPD3175 Clinical (unspecified phase)
0.6573 Remote Similarity NPD1725 Approved
0.6567 Remote Similarity NPD6377 Clinical (unspecified phase)
0.6562 Remote Similarity NPD7608 Discontinued
0.6557 Remote Similarity NPD3536 Discontinued
0.6556 Remote Similarity NPD2458 Approved
0.6556 Remote Similarity NPD2460 Phase 3
0.6556 Remote Similarity NPD4162 Approved
0.6556 Remote Similarity NPD2459 Approved
0.655 Remote Similarity NPD3863 Clinical (unspecified phase)
0.6538 Remote Similarity NPD3281 Clinical (unspecified phase)
0.6535 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6526 Remote Similarity NPD8031 Discontinued
0.6524 Remote Similarity NPD2541 Clinical (unspecified phase)
0.6497 Remote Similarity NPD3052 Approved
0.6497 Remote Similarity NPD3054 Approved
0.6494 Remote Similarity NPD9718 Approved
0.6467 Remote Similarity NPD2874 Phase 2
0.6467 Remote Similarity NPD3985 Discontinued
0.6457 Remote Similarity NPD3056 Clinical (unspecified phase)
0.6453 Remote Similarity NPD1819 Approved
0.6453 Remote Similarity NPD1817 Approved
0.6453 Remote Similarity NPD1818 Approved
0.6453 Remote Similarity NPD1820 Approved
0.6453 Remote Similarity NPD1770 Clinical (unspecified phase)
0.6432 Remote Similarity NPD1975 Clinical (unspecified phase)
0.642 Remote Similarity NPD2245 Discovery
0.641 Remote Similarity NPD3451 Clinical (unspecified phase)
0.64 Remote Similarity NPD5163 Phase 2
0.64 Remote Similarity NPD3166 Approved
0.64 Remote Similarity NPD3167 Approved
0.64 Remote Similarity NPD3180 Approved
0.64 Remote Similarity NPD3179 Approved
0.64 Remote Similarity NPD3164 Approved
0.64 Remote Similarity NPD3165 Approved
0.6398 Remote Similarity NPD5586 Clinical (unspecified phase)
0.639 Remote Similarity NPD4466 Phase 1
0.6382 Remote Similarity NPD1298 Discontinued
0.6378 Remote Similarity NPD5348 Clinical (unspecified phase)
0.6373 Remote Similarity NPD2041 Clinical (unspecified phase)
0.6373 Remote Similarity NPD2042 Clinical (unspecified phase)
0.6364 Remote Similarity NPD3687 Approved
0.6364 Remote Similarity NPD3686 Approved
0.6354 Remote Similarity NPD1307 Phase 2
0.6354 Remote Similarity NPD1309 Phase 2
0.6349 Remote Similarity NPD6677 Suspended
0.6349 Remote Similarity NPD7118 Clinical (unspecified phase)
0.6345 Remote Similarity NPD2822 Clinical (unspecified phase)
0.6327 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6324 Remote Similarity NPD6087 Phase 1
0.6321 Remote Similarity NPD6315 Phase 2
0.6319 Remote Similarity NPD7596 Clinical (unspecified phase)
0.6319 Remote Similarity NPD3655 Clinical (unspecified phase)
0.6316 Remote Similarity NPD5355 Approved
0.6316 Remote Similarity NPD5356 Approved
0.6294 Remote Similarity NPD5605 Phase 2
0.629 Remote Similarity NPD6419 Discontinued
0.6289 Remote Similarity NPD2904 Discontinued
0.6284 Remote Similarity NPD3060 Approved
0.6283 Remote Similarity NPD5773 Approved
0.6283 Remote Similarity NPD3465 Clinical (unspecified phase)
0.6283 Remote Similarity NPD5772 Approved
0.6281 Remote Similarity NPD5557 Phase 1
0.6269 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6264 Remote Similarity NPD1794 Approved
0.6257 Remote Similarity NPD7526 Approved
0.6257 Remote Similarity NPD4186 Clinical (unspecified phase)
0.6257 Remote Similarity NPD52 Approved
0.6257 Remote Similarity NPD7527 Clinical (unspecified phase)
0.6256 Remote Similarity NPD3153 Approved
0.6256 Remote Similarity NPD3154 Approved
0.6243 Remote Similarity NPD2649 Approved
0.6243 Remote Similarity NPD2651 Approved
0.6243 Remote Similarity NPD824 Approved
0.6238 Remote Similarity NPD7811 Phase 3
0.6238 Remote Similarity NPD7810 Phase 3
0.6237 Remote Similarity NPD6862 Phase 2
0.6236 Remote Similarity NPD3162 Approved
0.6236 Remote Similarity NPD3163 Approved
0.6231 Remote Similarity NPD6042 Phase 2
0.6231 Remote Similarity NPD42 Phase 2
0.623 Remote Similarity NPD4018 Clinical (unspecified phase)
0.623 Remote Similarity NPD7153 Discontinued
0.6223 Remote Similarity NPD1670 Discontinued
0.6219 Remote Similarity NPD7038 Approved
0.6219 Remote Similarity NPD7039 Approved
0.6212 Remote Similarity NPD3366 Approved
0.6211 Remote Similarity NPD2592 Discontinued
0.6209 Remote Similarity NPD2161 Phase 2
0.6207 Remote Similarity NPD6853 Approved
0.6207 Remote Similarity NPD6851 Approved
0.6203 Remote Similarity NPD3157 Approved
0.6203 Remote Similarity NPD1771 Clinical (unspecified phase)
0.6203 Remote Similarity NPD4662 Approved
0.6203 Remote Similarity NPD3158 Phase 1
0.6203 Remote Similarity NPD4661 Approved
0.6202 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6201 Remote Similarity NPD3597 Clinical (unspecified phase)
0.6198 Remote Similarity NPD7972 Discontinued
0.619 Remote Similarity NPD4124 Clinical (unspecified phase)
0.6183 Remote Similarity NPD5295 Discontinued
0.6181 Remote Similarity NPD6620 Discovery
0.6181 Remote Similarity NPD3909 Discontinued
0.6178 Remote Similarity NPD6072 Discontinued
0.6175 Remote Similarity NPD3656 Approved
0.617 Remote Similarity NPD2183 Approved
0.617 Remote Similarity NPD7613 Discontinued
0.617 Remote Similarity NPD2184 Approved
0.6169 Remote Similarity NPD6297 Approved
0.6166 Remote Similarity NPD7318 Phase 3
0.6166 Remote Similarity NPD5967 Approved
0.6158 Remote Similarity NPD2614 Approved
0.6154 Remote Similarity NPD8245 Clinical (unspecified phase)
0.6149 Remote Similarity NPD3676 Clinical (unspecified phase)
0.6149 Remote Similarity NPD2428 Approved
0.6149 Remote Similarity NPD2429 Approved
0.6138 Remote Similarity NPD6662 Clinical (unspecified phase)
0.6133 Remote Similarity NPD2653 Approved
0.6129 Remote Similarity NPD2677 Approved
0.6126 Remote Similarity NPD1337 Clinical (unspecified phase)
0.6124 Remote Similarity NPD3136 Phase 2
0.6122 Remote Similarity NPD4666 Phase 3
0.6117 Remote Similarity NPD7020 Approved
0.6117 Remote Similarity NPD7019 Approved
0.6117 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6114 Remote Similarity NPD2977 Approved
0.6114 Remote Similarity NPD2978 Approved
0.6111 Remote Similarity NPD3140 Approved
0.6111 Remote Similarity NPD5137 Approved
0.6111 Remote Similarity NPD3142 Approved
0.6111 Remote Similarity NPD2216 Approved
0.6111 Remote Similarity NPD2215 Approved
0.6108 Remote Similarity NPD5061 Approved
0.6108 Remote Similarity NPD5062 Approved
0.6105 Remote Similarity NPD2556 Approved
0.6105 Remote Similarity NPD2554 Approved
0.6102 Remote Similarity NPD2250 Discontinued
0.6092 Remote Similarity NPD2231 Phase 2
0.6092 Remote Similarity NPD2235 Phase 2
0.6089 Remote Similarity NPD3823 Discontinued
0.6085 Remote Similarity NPD2186 Approved
0.6082 Remote Similarity NPD2296 Approved
0.6075 Remote Similarity NPD6863 Phase 2
0.6075 Remote Similarity NPD1662 Clinical (unspecified phase)
0.6075 Remote Similarity NPD4971 Clinical (unspecified phase)
0.6073 Remote Similarity NPD3866 Clinical (unspecified phase)
0.6071 Remote Similarity NPD5709 Phase 3
0.6068 Remote Similarity NPD6089 Clinical (unspecified phase)
0.6066 Remote Similarity NPD2154 Approved
0.6066 Remote Similarity NPD2156 Approved
0.6066 Remote Similarity NPD2155 Approved
0.6062 Remote Similarity NPD7577 Discontinued
0.6062 Remote Similarity NPD7317 Phase 3
0.6056 Remote Similarity NPD5745 Approved
0.6056 Remote Similarity NPD1726 Clinical (unspecified phase)
0.6056 Remote Similarity NPD839 Approved
0.6056 Remote Similarity NPD840 Approved
0.6051 Remote Similarity NPD4581 Clinical (unspecified phase)
0.6043 Remote Similarity NPD3692 Discontinued
0.6043 Remote Similarity NPD5160 Discontinued
0.6042 Remote Similarity NPD6876 Approved
0.6042 Remote Similarity NPD6875 Approved
0.6039 Remote Similarity NPD3490 Discontinued
0.6033 Remote Similarity NPD3156 Discontinued
0.603 Remote Similarity NPD2388 Discontinued
0.603 Remote Similarity NPD8051 Clinical (unspecified phase)
0.6029 Remote Similarity NPD7190 Clinical (unspecified phase)
0.6029 Remote Similarity NPD3936 Clinical (unspecified phase)
0.602 Remote Similarity NPD5940 Clinical (unspecified phase)
0.6012 Remote Similarity NPD821 Approved
0.6011 Remote Similarity NPD6667 Approved
0.6011 Remote Similarity NPD743 Approved
0.6011 Remote Similarity NPD6666 Approved
0.6011 Remote Similarity NPD5266 Clinical (unspecified phase)
0.601 Remote Similarity NPD7109 Clinical (unspecified phase)
0.601 Remote Similarity NPD7110 Phase 1
0.601 Remote Similarity NPD3511 Discontinued
0.6 Remote Similarity NPD6390 Discontinued
0.6 Remote Similarity NPD7316 Discontinued
0.599 Remote Similarity NPD5095 Phase 3
0.599 Remote Similarity NPD6523 Clinical (unspecified phase)
0.599 Remote Similarity NPD3933 Discontinued
0.599 Remote Similarity NPD3857 Clinical (unspecified phase)
0.599 Remote Similarity NPD5096 Phase 3
0.5983 Remote Similarity NPD8059 Phase 3
0.5983 Remote Similarity NPD8058 Clinical (unspecified phase)
0.5981 Remote Similarity NPD6519 Phase 2
0.598 Remote Similarity NPD4010 Discontinued
0.5979 Remote Similarity NPD1774 Approved
0.5973 Remote Similarity NPD3336 Discovery
0.5972 Remote Similarity NPD7256 Discontinued

Structure

External Identifiers

PubChem CID   23426312
ChEMBL   CHEMBL2047175
ZINC  

Physicochemical Properties

Molecular Weight:  712.84
ALogP:  0.5631
MLogP:  2.45
XLogP:  3.723
# Rotatable Bonds:  17
Polar Surface Area:  115.4
# H-Bond Aceptor:  5
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  33

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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