Natural Product: NPC470137

Natural Product ID:  NPC470137
Common Name:   Macrolactin W
IUPAC Name:   1-O-[(3Z,5E,8S,9E,11Z,14S,16R,17E,19Z,24S)-14,16-dihydroxy-24-methyl-2-oxo-1-oxacyclotetracosa-3,5,9,11,17,19-hexaen-8-yl] 4-O-[(2R,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] butanedioate
Synonyms:   Macrolactin W
Molecular Formula:   C34H48O13
Standard InCHIKey:  PZILNXCOIHJJCW-MMFXVHKESA-N
Standard InCHI:  InChI=1S/C34H48O13/c1-23-13-7-3-2-4-8-14-24(36)21-25(37)15-9-5-10-16-26(17-11-6-12-18-28(38)44-23)45-29(39)19-20-30(40)47-34-33(43)32(42)31(41)27(22-35)46-34/h2,4-6,8-12,14,16,18,23-27,31-37,41-43H,3,7,13,15,17,19-22H2,1H3/b4-2-,9-5-,11-6+,14-8+,16-10+,18-12-/t23-,24-,25-,26+,27-,31-,32+,33-,34+/m0/s1
Canonical SMILES:  OC[C@@H]1O[C@H](OC(=O)CCC(=O)O[C@H]2C/C=C/C=CC(=O)O[C@@H](C)CCC/C=CC=C[C@@H](C[C@H](C/C=CC=C2)O)O)[C@H]([C@@H]([C@H]1O)O)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
NPO20523 Bacillus subtilis Species Bacillaceae Bacteria PMID[23488669]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 64 ug/ml 19653640
NPT19 Organism Escherichia coli Escherichia coli MIC = 64 ug/ml 19653640
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 64 ug/ml 19459645
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 64 ug/ml 12036347

  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 NPC470137 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
0.939 High Similarity NPC142111
0.939 High Similarity NPC473315
0.9277 High Similarity NPC473308
0.9268 High Similarity NPC251026
0.9059 High Similarity NPC208473
0.8953 High Similarity NPC475186
0.8953 High Similarity NPC118077
0.8864 High Similarity NPC473311
0.869 High Similarity NPC469469
0.8539 High Similarity NPC285588
0.8391 Intermediate Similarity NPC475035
0.8352 Intermediate Similarity NPC110072
0.8333 Intermediate Similarity NPC133377
0.8315 Intermediate Similarity NPC475037
0.8313 Intermediate Similarity NPC326661
0.8295 Intermediate Similarity NPC470124
0.8261 Intermediate Similarity NPC238090
0.8261 Intermediate Similarity NPC320552
0.8261 Intermediate Similarity NPC472196
0.8261 Intermediate Similarity NPC472195
0.8214 Intermediate Similarity NPC110813
0.8211 Intermediate Similarity NPC203627
0.8182 Intermediate Similarity NPC266718
0.8172 Intermediate Similarity NPC294293
0.8172 Intermediate Similarity NPC159698
0.8171 Intermediate Similarity NPC284006
0.814 Intermediate Similarity NPC163362
0.814 Intermediate Similarity NPC133226
0.814 Intermediate Similarity NPC127295
0.814 Intermediate Similarity NPC470147
0.809 Intermediate Similarity NPC475034
0.8043 Intermediate Similarity NPC327253
0.8023 Intermediate Similarity NPC180725
0.8023 Intermediate Similarity NPC470149
0.8023 Intermediate Similarity NPC470148
0.7907 Intermediate Similarity NPC248775
0.7895 Intermediate Similarity NPC170204
0.7857 Intermediate Similarity NPC472173
0.7857 Intermediate Similarity NPC472174
0.7857 Intermediate Similarity NPC471637
0.7857 Intermediate Similarity NPC57586
0.7857 Intermediate Similarity NPC2313
0.7857 Intermediate Similarity NPC154132
0.7857 Intermediate Similarity NPC475655
0.7857 Intermediate Similarity NPC475157
0.7849 Intermediate Similarity NPC118078
0.7841 Intermediate Similarity NPC236649
0.7841 Intermediate Similarity NPC21693
0.7816 Intermediate Similarity NPC1180
0.7791 Intermediate Similarity NPC474026
0.7766 Intermediate Similarity NPC469410
0.7766 Intermediate Similarity NPC472197
0.7738 Intermediate Similarity NPC132938
0.7723 Intermediate Similarity NPC315070
0.7711 Intermediate Similarity NPC476012
0.7711 Intermediate Similarity NPC476037
0.77 Intermediate Similarity NPC197736
0.7684 Intermediate Similarity NPC61201
0.7667 Intermediate Similarity NPC156089
0.7667 Intermediate Similarity NPC470313
0.7667 Intermediate Similarity NPC38295
0.7667 Intermediate Similarity NPC473500
0.766 Intermediate Similarity NPC473904
0.766 Intermediate Similarity NPC303451
0.766 Intermediate Similarity NPC6414
0.7634 Intermediate Similarity NPC137368
0.7629 Intermediate Similarity NPC306041
0.7609 Intermediate Similarity NPC47937
0.7586 Intermediate Similarity NPC233071
0.7579 Intermediate Similarity NPC9447
0.7579 Intermediate Similarity NPC472199
0.7579 Intermediate Similarity NPC477749
0.7558 Intermediate Similarity NPC285840
0.7558 Intermediate Similarity NPC327041
0.7553 Intermediate Similarity NPC139418
0.7529 Intermediate Similarity NPC329890
0.7529 Intermediate Similarity NPC329914
0.7526 Intermediate Similarity NPC469543
0.75 Intermediate Similarity NPC473663
0.75 Intermediate Similarity NPC28304
0.75 Intermediate Similarity NPC477314
0.75 Intermediate Similarity NPC320089
0.75 Intermediate Similarity NPC473723
0.75 Intermediate Similarity NPC182292
0.75 Intermediate Similarity NPC298255
0.75 Intermediate Similarity NPC182383
0.75 Intermediate Similarity NPC475173
0.75 Intermediate Similarity NPC473561
0.7475 Intermediate Similarity NPC475653
0.7473 Intermediate Similarity NPC229799
0.7473 Intermediate Similarity NPC286770
0.7473 Intermediate Similarity NPC284472
0.7471 Intermediate Similarity NPC188860
0.7471 Intermediate Similarity NPC229655
0.7449 Intermediate Similarity NPC173329
0.7449 Intermediate Similarity NPC255410
0.7449 Intermediate Similarity NPC288350
0.7447 Intermediate Similarity NPC280621
0.7447 Intermediate Similarity NPC233551
0.7447 Intermediate Similarity NPC48338
0.7447 Intermediate Similarity NPC20339
0.7447 Intermediate Similarity NPC40376
0.7447 Intermediate Similarity NPC21208
0.7444 Intermediate Similarity NPC280367
0.7439 Intermediate Similarity NPC146811
0.7426 Intermediate Similarity NPC195510
0.7426 Intermediate Similarity NPC13171
0.7426 Intermediate Similarity NPC201191
0.7423 Intermediate Similarity NPC472198
0.7416 Intermediate Similarity NPC179933
0.7416 Intermediate Similarity NPC321728
0.7412 Intermediate Similarity NPC293114
0.74 Intermediate Similarity NPC306344
0.74 Intermediate Similarity NPC255677
0.74 Intermediate Similarity NPC22149
0.7396 Intermediate Similarity NPC473707
0.7391 Intermediate Similarity NPC288471
0.7386 Intermediate Similarity NPC475711
0.7381 Intermediate Similarity NPC475982
0.7374 Intermediate Similarity NPC120299
0.7368 Intermediate Similarity NPC477748
0.7363 Intermediate Similarity NPC474959
0.7363 Intermediate Similarity NPC310450
0.7363 Intermediate Similarity NPC11383
0.7363 Intermediate Similarity NPC475046
0.7353 Intermediate Similarity NPC267869
0.7353 Intermediate Similarity NPC234304
0.7353 Intermediate Similarity NPC197541
0.7353 Intermediate Similarity NPC118761
0.7353 Intermediate Similarity NPC284929
0.7347 Intermediate Similarity NPC300710
0.734 Intermediate Similarity NPC178215
0.734 Intermediate Similarity NPC316138
0.734 Intermediate Similarity NPC45409
0.734 Intermediate Similarity NPC313658
0.7333 Intermediate Similarity NPC133625
0.7327 Intermediate Similarity NPC20673
0.7327 Intermediate Similarity NPC219038
0.7326 Intermediate Similarity NPC185186
0.7326 Intermediate Similarity NPC327383
0.732 Intermediate Similarity NPC11456
0.7317 Intermediate Similarity NPC19769
0.7312 Intermediate Similarity NPC471494
0.73 Intermediate Similarity NPC81483
0.73 Intermediate Similarity NPC61630
0.73 Intermediate Similarity NPC169468
0.73 Intermediate Similarity NPC307517
0.7294 Intermediate Similarity NPC474078
0.7292 Intermediate Similarity NPC239517
0.7292 Intermediate Similarity NPC202886
0.7292 Intermediate Similarity NPC117596
0.7282 Intermediate Similarity NPC86095
0.7273 Intermediate Similarity NPC54731
0.7262 Intermediate Similarity NPC63873
0.7255 Intermediate Similarity NPC471599
0.7255 Intermediate Similarity NPC310804
0.7255 Intermediate Similarity NPC261117
0.7255 Intermediate Similarity NPC250545
0.7255 Intermediate Similarity NPC473596
0.7255 Intermediate Similarity NPC222062
0.7253 Intermediate Similarity NPC8538
0.7253 Intermediate Similarity NPC297440
0.7253 Intermediate Similarity NPC184208
0.7253 Intermediate Similarity NPC315731
0.7245 Intermediate Similarity NPC256368
0.7241 Intermediate Similarity NPC107654
0.7241 Intermediate Similarity NPC315843
0.7238 Intermediate Similarity NPC193765
0.7234 Intermediate Similarity NPC114694
0.7234 Intermediate Similarity NPC232555
0.7234 Intermediate Similarity NPC107717
0.7234 Intermediate Similarity NPC171174
0.7234 Intermediate Similarity NPC311163
0.7234 Intermediate Similarity NPC240695
0.7234 Intermediate Similarity NPC134865
0.7234 Intermediate Similarity NPC69082
0.7234 Intermediate Similarity NPC142117
0.7234 Intermediate Similarity NPC103523
0.7234 Intermediate Similarity NPC62118
0.7234 Intermediate Similarity NPC475581
0.7234 Intermediate Similarity NPC279267
0.7234 Intermediate Similarity NPC231096
0.7229 Intermediate Similarity NPC201356
0.7228 Intermediate Similarity NPC244878
0.7216 Intermediate Similarity NPC472126
0.7216 Intermediate Similarity NPC472124
0.7216 Intermediate Similarity NPC472125
0.7216 Intermediate Similarity NPC477349
0.7209 Intermediate Similarity NPC475762
0.72 Intermediate Similarity NPC474194
0.72 Intermediate Similarity NPC476612
0.72 Intermediate Similarity NPC40812
0.72 Intermediate Similarity NPC476613
0.72 Intermediate Similarity NPC475332
0.7195 Intermediate Similarity NPC13143
0.7195 Intermediate Similarity NPC294813
0.7188 Intermediate Similarity NPC42598
0.7188 Intermediate Similarity NPC40066
0.7188 Intermediate Similarity NPC477011
0.7188 Intermediate Similarity NPC318963

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC470137 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
0.8211 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7474 Intermediate Similarity NPD7838 Discovery
0.7113 Intermediate Similarity NPD6698 Approved
0.7113 Intermediate Similarity NPD46 Approved
0.6916 Remote Similarity NPD6686 Approved
0.6869 Remote Similarity NPD7983 Approved
0.681 Remote Similarity NPD7830 Approved
0.681 Remote Similarity NPD7829 Approved
0.6783 Remote Similarity NPD8516 Approved
0.6783 Remote Similarity NPD8517 Approved
0.6783 Remote Similarity NPD8513 Phase 3
0.6783 Remote Similarity NPD8515 Approved
0.6744 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6727 Remote Similarity NPD8413 Clinical (unspecified phase)
0.66 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6522 Remote Similarity NPD7641 Discontinued
0.6496 Remote Similarity NPD8444 Approved
0.6442 Remote Similarity NPD7839 Suspended
0.6429 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6417 Remote Similarity NPD8451 Approved
0.6387 Remote Similarity NPD7642 Approved
0.6364 Remote Similarity NPD8448 Approved
0.6356 Remote Similarity NPD7503 Approved
0.6355 Remote Similarity NPD5344 Discontinued
0.6333 Remote Similarity NPD8341 Approved
0.6333 Remote Similarity NPD8299 Approved
0.6333 Remote Similarity NPD8342 Approved
0.6333 Remote Similarity NPD8340 Approved
0.6327 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6262 Remote Similarity NPD6648 Approved
0.6239 Remote Similarity NPD1407 Approved
0.623 Remote Similarity NPD8074 Phase 3
0.6216 Remote Similarity NPD7899 Clinical (unspecified phase)
0.621 Remote Similarity NPD8390 Approved
0.621 Remote Similarity NPD8392 Approved
0.621 Remote Similarity NPD8391 Approved
0.6083 Remote Similarity NPD8033 Approved
0.6061 Remote Similarity NPD6110 Phase 1
0.6053 Remote Similarity NPD6371 Approved
0.6047 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6019 Remote Similarity NPD4225 Approved
0.6 Remote Similarity NPD8294 Approved
0.6 Remote Similarity NPD896 Approved
0.6 Remote Similarity NPD898 Approved
0.6 Remote Similarity NPD6109 Phase 1
0.6 Remote Similarity NPD897 Approved
0.6 Remote Similarity NPD8377 Approved
0.598 Remote Similarity NPD4250 Approved
0.598 Remote Similarity NPD4251 Approved
0.5966 Remote Similarity NPD7328 Approved
0.5966 Remote Similarity NPD7327 Approved
0.595 Remote Similarity NPD8335 Approved
0.595 Remote Similarity NPD8378 Approved
0.595 Remote Similarity NPD8379 Approved
0.595 Remote Similarity NPD8296 Approved
0.595 Remote Similarity NPD8380 Approved
0.5918 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5917 Remote Similarity NPD7516 Approved
0.5905 Remote Similarity NPD7637 Suspended
0.5887 Remote Similarity NPD7507 Approved
0.5882 Remote Similarity NPD4249 Approved
0.5854 Remote Similarity NPD2269 Approved
0.5849 Remote Similarity NPD5778 Approved
0.5849 Remote Similarity NPD5779 Approved
0.5826 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5816 Remote Similarity NPD7329 Approved
0.5814 Remote Similarity NPD585 Clinical (unspecified phase)
0.581 Remote Similarity NPD5785 Approved
0.5789 Remote Similarity NPD6412 Phase 2
0.5773 Remote Similarity NPD4756 Discovery
0.576 Remote Similarity NPD8273 Phase 1
0.575 Remote Similarity NPD7500 Approved
0.5748 Remote Similarity NPD7319 Approved
0.5732 Remote Similarity NPD904 Phase 3
0.5732 Remote Similarity NPD905 Approved
0.5726 Remote Similarity NPD8328 Phase 3
0.5726 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5714 Remote Similarity NPD4271 Approved
0.5714 Remote Similarity NPD4268 Approved
0.5684 Remote Similarity NPD3181 Approved
0.5667 Remote Similarity NPD3197 Phase 1
0.5662 Remote Similarity NPD7266 Discontinued
0.5641 Remote Similarity NPD6421 Discontinued
0.5632 Remote Similarity NPD69 Approved
0.5632 Remote Similarity NPD9119 Approved
0.5631 Remote Similarity NPD5363 Approved
0.563 Remote Similarity NPD8133 Approved
0.562 Remote Similarity NPD7505 Discontinued
0.56 Remote Similarity NPD4820 Approved
0.56 Remote Similarity NPD4821 Approved
0.56 Remote Similarity NPD4819 Approved
0.56 Remote Similarity NPD4822 Approved

Structure

External Identifiers

PubChem CID   54581687
ChEMBL   CHEMBL1780188
ZINC  

Physicochemical Properties

Molecular Weight:  664.31
ALogP:  -0.7248
MLogP:  3.77
XLogP:  2.307
# Rotatable Bonds:  15
Polar Surface Area:  209.51
# H-Bond Aceptor:  13
# H-Bond Donor:  6
# Rings:  2
# Heavy Atoms:  47

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Biological Activities  
Similar NPs/Drugs