Natural Product: NPC473311

Natural Product ID:  NPC473311
Common Name:   Macrolactin O
IUPAC Name:   (3Z,5E,8S,9E,11Z,14S,19E,24R)-14-hydroxy-24-methyl-8-[(2S,3S,4R,5R,6S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1-oxacyclotetracosa-3,5,9,11,19-pentaene-2,16-dione
Synonyms:   Macrolactin O
Molecular Formula:   C30H44O10
Standard InCHIKey:  WPGAONUYAGVAII-PMZILUDRSA-N
Standard InCHI:  InChI=1S/C30H44O10/c1-21-13-7-3-2-4-8-14-22(32)19-23(33)15-9-5-10-16-24(17-11-6-12-18-26(34)38-21)39-30-29(37)28(36)27(35)25(20-31)40-30/h2,4-6,9-12,16,18,21,23-25,27-31,33,35-37H,3,7-8,13-15,17,19-20H2,1H3/b4-2+,9-5-,11-6+,16-10+,18-12-/t21-,23+,24-,25+,27+,28-,29+,30+/m1/s1
Canonical SMILES:  OC[C@@H]1O[C@H](O[C@H]2C/C=C/C=CC(=O)O[C@H](C)CCC/C=C/CCC(=O)C[C@H](C/C=CC=C2)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
NPO32689 bacillus sp. ah159-1 Species NA NA PMID[17887720]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT6049 Individual Protein Peptide deformylase Staphylococcus aureus subsp. aureus Mu50 IC50 = 53500 nM 23036956
NPT19 Organism Escherichia coli Escherichia coli MIC = 100 ug/ml 9868159

  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 NPC473311 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
0.907 High Similarity NPC208473
0.9059 High Similarity NPC473308
0.9048 High Similarity NPC251026
0.8941 High Similarity NPC142111
0.8941 High Similarity NPC473315
0.8929 High Similarity NPC469469
0.8864 High Similarity NPC470137
0.8523 High Similarity NPC470124
0.8333 Intermediate Similarity NPC475186
0.8333 Intermediate Similarity NPC118077
0.8333 Intermediate Similarity NPC475037
0.8191 Intermediate Similarity NPC294293
0.8152 Intermediate Similarity NPC285588
0.814 Intermediate Similarity NPC133377
0.814 Intermediate Similarity NPC182292
0.8118 Intermediate Similarity NPC326661
0.8111 Intermediate Similarity NPC475034
0.8085 Intermediate Similarity NPC320552
0.8085 Intermediate Similarity NPC472196
0.8085 Intermediate Similarity NPC472195
0.8085 Intermediate Similarity NPC238090
0.8068 Intermediate Similarity NPC21693
0.8068 Intermediate Similarity NPC280367
0.8068 Intermediate Similarity NPC236649
0.8065 Intermediate Similarity NPC327253
0.8046 Intermediate Similarity NPC180725
0.8023 Intermediate Similarity NPC474026
0.8023 Intermediate Similarity NPC110813
0.8 Intermediate Similarity NPC260396
0.8 Intermediate Similarity NPC475035
0.8 Intermediate Similarity NPC266718
0.8 Intermediate Similarity NPC159698
0.7979 Intermediate Similarity NPC110072
0.7979 Intermediate Similarity NPC469410
0.7979 Intermediate Similarity NPC472199
0.7955 Intermediate Similarity NPC133226
0.7955 Intermediate Similarity NPC470147
0.7931 Intermediate Similarity NPC248775
0.7917 Intermediate Similarity NPC170204
0.7889 Intermediate Similarity NPC473500
0.7889 Intermediate Similarity NPC284472
0.7889 Intermediate Similarity NPC38295
0.7889 Intermediate Similarity NPC229799
0.7889 Intermediate Similarity NPC156089
0.7889 Intermediate Similarity NPC286770
0.7889 Intermediate Similarity NPC470313
0.7879 Intermediate Similarity NPC57586
0.7879 Intermediate Similarity NPC2313
0.7879 Intermediate Similarity NPC154132
0.7879 Intermediate Similarity NPC475655
0.7879 Intermediate Similarity NPC471637
0.7879 Intermediate Similarity NPC475157
0.7872 Intermediate Similarity NPC118078
0.7841 Intermediate Similarity NPC1180
0.7841 Intermediate Similarity NPC470149
0.7841 Intermediate Similarity NPC470148
0.7822 Intermediate Similarity NPC469869
0.7812 Intermediate Similarity NPC472198
0.7802 Intermediate Similarity NPC288471
0.7789 Intermediate Similarity NPC9447
0.7778 Intermediate Similarity NPC11383
0.7778 Intermediate Similarity NPC310450
0.7778 Intermediate Similarity NPC474959
0.7778 Intermediate Similarity NPC475046
0.7767 Intermediate Similarity NPC193765
0.7765 Intermediate Similarity NPC329914
0.7755 Intermediate Similarity NPC266842
0.7753 Intermediate Similarity NPC127295
0.7753 Intermediate Similarity NPC163362
0.7738 Intermediate Similarity NPC476012
0.7723 Intermediate Similarity NPC197736
0.7708 Intermediate Similarity NPC61201
0.7708 Intermediate Similarity NPC320089
0.7684 Intermediate Similarity NPC303451
0.7684 Intermediate Similarity NPC6414
0.7677 Intermediate Similarity NPC203627
0.7677 Intermediate Similarity NPC161855
0.7674 Intermediate Similarity NPC472173
0.766 Intermediate Similarity NPC137368
0.7653 Intermediate Similarity NPC306041
0.7634 Intermediate Similarity NPC47937
0.7614 Intermediate Similarity NPC233071
0.7614 Intermediate Similarity NPC475711
0.7604 Intermediate Similarity NPC477749
0.7604 Intermediate Similarity NPC472197
0.7596 Intermediate Similarity NPC472507
0.7596 Intermediate Similarity NPC473807
0.7586 Intermediate Similarity NPC327041
0.7586 Intermediate Similarity NPC285840
0.7579 Intermediate Similarity NPC14901
0.7579 Intermediate Similarity NPC130359
0.7576 Intermediate Similarity NPC476612
0.7576 Intermediate Similarity NPC476613
0.7576 Intermediate Similarity NPC40812
0.7573 Intermediate Similarity NPC315070
0.7558 Intermediate Similarity NPC327383
0.7558 Intermediate Similarity NPC185186
0.7558 Intermediate Similarity NPC329890
0.7551 Intermediate Similarity NPC469543
0.7549 Intermediate Similarity NPC309398
0.7529 Intermediate Similarity NPC476037
0.7527 Intermediate Similarity NPC182383
0.7526 Intermediate Similarity NPC473723
0.7526 Intermediate Similarity NPC473663
0.7526 Intermediate Similarity NPC475173
0.7526 Intermediate Similarity NPC473561
0.75 Intermediate Similarity NPC198422
0.75 Intermediate Similarity NPC202886
0.75 Intermediate Similarity NPC49392
0.75 Intermediate Similarity NPC190400
0.75 Intermediate Similarity NPC473904
0.75 Intermediate Similarity NPC475879
0.75 Intermediate Similarity NPC188860
0.75 Intermediate Similarity NPC472015
0.75 Intermediate Similarity NPC40182
0.7475 Intermediate Similarity NPC476066
0.7475 Intermediate Similarity NPC473765
0.7475 Intermediate Similarity NPC475164
0.7475 Intermediate Similarity NPC473605
0.7475 Intermediate Similarity NPC475593
0.7475 Intermediate Similarity NPC173329
0.7475 Intermediate Similarity NPC475540
0.7475 Intermediate Similarity NPC255410
0.7475 Intermediate Similarity NPC475375
0.7475 Intermediate Similarity NPC473291
0.7475 Intermediate Similarity NPC475525
0.7475 Intermediate Similarity NPC288350
0.7475 Intermediate Similarity NPC475241
0.7474 Intermediate Similarity NPC233551
0.7474 Intermediate Similarity NPC40376
0.7474 Intermediate Similarity NPC48338
0.7474 Intermediate Similarity NPC471755
0.7474 Intermediate Similarity NPC471756
0.7474 Intermediate Similarity NPC21208
0.7474 Intermediate Similarity NPC280621
0.7474 Intermediate Similarity NPC20339
0.7473 Intermediate Similarity NPC297440
0.7471 Intermediate Similarity NPC474321
0.7471 Intermediate Similarity NPC472174
0.7455 Intermediate Similarity NPC13710
0.7453 Intermediate Similarity NPC472508
0.7451 Intermediate Similarity NPC471599
0.7451 Intermediate Similarity NPC201191
0.7449 Intermediate Similarity NPC256368
0.7449 Intermediate Similarity NPC25701
0.7449 Intermediate Similarity NPC2003
0.7447 Intermediate Similarity NPC477015
0.7444 Intermediate Similarity NPC321728
0.7444 Intermediate Similarity NPC469747
0.7444 Intermediate Similarity NPC263574
0.7442 Intermediate Similarity NPC293114
0.7442 Intermediate Similarity NPC475762
0.7423 Intermediate Similarity NPC473707
0.7423 Intermediate Similarity NPC477349
0.7419 Intermediate Similarity NPC41856
0.7411 Intermediate Similarity NPC470829
0.7411 Intermediate Similarity NPC473228
0.7404 Intermediate Similarity NPC476740
0.7404 Intermediate Similarity NPC476738
0.74 Intermediate Similarity NPC120299
0.74 Intermediate Similarity NPC472290
0.7396 Intermediate Similarity NPC139418
0.7396 Intermediate Similarity NPC477748
0.7396 Intermediate Similarity NPC477017
0.7396 Intermediate Similarity NPC477016
0.7386 Intermediate Similarity NPC473948
0.7379 Intermediate Similarity NPC474581
0.7379 Intermediate Similarity NPC475367
0.7379 Intermediate Similarity NPC473816
0.7374 Intermediate Similarity NPC300710
0.7368 Intermediate Similarity NPC45409
0.7368 Intermediate Similarity NPC178215
0.7368 Intermediate Similarity NPC316138
0.7368 Intermediate Similarity NPC313658
0.7358 Intermediate Similarity NPC133625
0.7356 Intermediate Similarity NPC284006
0.7356 Intermediate Similarity NPC132938
0.7353 Intermediate Similarity NPC476611
0.7353 Intermediate Similarity NPC4637
0.7353 Intermediate Similarity NPC98859
0.7353 Intermediate Similarity NPC219038
0.7347 Intermediate Similarity NPC473520
0.7347 Intermediate Similarity NPC478036
0.7347 Intermediate Similarity NPC11456
0.7347 Intermediate Similarity NPC478037
0.734 Intermediate Similarity NPC477013
0.734 Intermediate Similarity NPC120398
0.734 Intermediate Similarity NPC322529
0.734 Intermediate Similarity NPC329615
0.734 Intermediate Similarity NPC329838
0.734 Intermediate Similarity NPC471567
0.734 Intermediate Similarity NPC477014
0.734 Intermediate Similarity NPC471494
0.7333 Intermediate Similarity NPC477314
0.7333 Intermediate Similarity NPC254538
0.7333 Intermediate Similarity NPC474285
0.7327 Intermediate Similarity NPC83895
0.7327 Intermediate Similarity NPC255592
0.7327 Intermediate Similarity NPC261377
0.7327 Intermediate Similarity NPC475653

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC473311 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
0.7677 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD7838 Discovery
0.75 Intermediate Similarity NPD46 Approved
0.75 Intermediate Similarity NPD6698 Approved
0.7281 Intermediate Similarity NPD7829 Approved
0.7281 Intermediate Similarity NPD7830 Approved
0.7264 Intermediate Similarity NPD6686 Approved
0.7245 Intermediate Similarity NPD7983 Approved
0.7105 Intermediate Similarity NPD8444 Approved
0.6983 Remote Similarity NPD7642 Approved
0.6957 Remote Similarity NPD8516 Approved
0.6957 Remote Similarity NPD8517 Approved
0.6957 Remote Similarity NPD8513 Phase 3
0.6957 Remote Similarity NPD8515 Approved
0.6842 Remote Similarity NPD7641 Discontinued
0.6796 Remote Similarity NPD7839 Suspended
0.6723 Remote Similarity NPD8451 Approved
0.6667 Remote Similarity NPD8448 Approved
0.6607 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6591 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6545 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6525 Remote Similarity NPD7503 Approved
0.6518 Remote Similarity NPD6371 Approved
0.6504 Remote Similarity NPD8390 Approved
0.6504 Remote Similarity NPD8392 Approved
0.6504 Remote Similarity NPD8391 Approved
0.65 Remote Similarity NPD8341 Approved
0.65 Remote Similarity NPD8299 Approved
0.65 Remote Similarity NPD8340 Approved
0.65 Remote Similarity NPD8342 Approved
0.6471 Remote Similarity NPD4246 Clinical (unspecified phase)
0.6471 Remote Similarity NPD8522 Clinical (unspecified phase)
0.6393 Remote Similarity NPD8074 Phase 3
0.6389 Remote Similarity NPD5344 Discontinued
0.6364 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6346 Remote Similarity NPD5778 Approved
0.6346 Remote Similarity NPD5779 Approved
0.6327 Remote Similarity NPD5209 Approved
0.6325 Remote Similarity NPD7500 Approved
0.6311 Remote Similarity NPD5785 Approved
0.6296 Remote Similarity NPD6648 Approved
0.629 Remote Similarity NPD7319 Approved
0.625 Remote Similarity NPD7637 Suspended
0.625 Remote Similarity NPD6412 Phase 2
0.6222 Remote Similarity NPD896 Approved
0.6222 Remote Similarity NPD898 Approved
0.6222 Remote Similarity NPD897 Approved
0.6204 Remote Similarity NPD4225 Approved
0.6202 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6179 Remote Similarity NPD7507 Approved
0.6176 Remote Similarity NPD4250 Approved
0.6176 Remote Similarity NPD4251 Approved
0.6148 Remote Similarity NPD8328 Phase 3
0.6146 Remote Similarity NPD4756 Discovery
0.6139 Remote Similarity NPD5363 Approved
0.6134 Remote Similarity NPD7327 Approved
0.6134 Remote Similarity NPD7328 Approved
0.6122 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6116 Remote Similarity NPD8033 Approved
0.6083 Remote Similarity NPD7516 Approved
0.6078 Remote Similarity NPD4249 Approved
0.6075 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6067 Remote Similarity NPD3197 Phase 1
0.6058 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6058 Remote Similarity NPD6101 Approved
0.6048 Remote Similarity NPD8273 Phase 1
0.6034 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6033 Remote Similarity NPD8377 Approved
0.6033 Remote Similarity NPD8294 Approved
0.602 Remote Similarity NPD7329 Approved
0.5984 Remote Similarity NPD8380 Approved
0.5984 Remote Similarity NPD8379 Approved
0.5984 Remote Similarity NPD8378 Approved
0.5984 Remote Similarity NPD8296 Approved
0.5984 Remote Similarity NPD8335 Approved
0.5982 Remote Similarity NPD1407 Approved
0.596 Remote Similarity NPD4252 Approved
0.5943 Remote Similarity NPD6411 Approved
0.5941 Remote Similarity NPD6110 Phase 1
0.5935 Remote Similarity NPD8080 Discontinued
0.5918 Remote Similarity NPD4268 Approved
0.5918 Remote Similarity NPD4271 Approved
0.5917 Remote Similarity NPD7115 Discovery
0.5895 Remote Similarity NPD3181 Approved
0.5862 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5862 Remote Similarity NPD6109 Phase 1
0.5842 Remote Similarity NPD4269 Approved
0.5842 Remote Similarity NPD4270 Approved
0.5833 Remote Similarity NPD5282 Discontinued
0.5827 Remote Similarity NPD7736 Approved
0.5806 Remote Similarity NPD6370 Approved
0.58 Remote Similarity NPD4820 Approved
0.58 Remote Similarity NPD4819 Approved
0.58 Remote Similarity NPD4821 Approved
0.58 Remote Similarity NPD4822 Approved
0.5798 Remote Similarity NPD8133 Approved
0.5785 Remote Similarity NPD8137 Clinical (unspecified phase)
0.5785 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5784 Remote Similarity NPD7154 Phase 3
0.5776 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5769 Remote Similarity NPD5786 Approved
0.5766 Remote Similarity NPD7638 Approved
0.5743 Remote Similarity NPD5369 Approved
0.5726 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5714 Remote Similarity NPD7492 Approved
0.5714 Remote Similarity NPD7639 Approved
0.5714 Remote Similarity NPD7640 Approved
0.5714 Remote Similarity NPD2269 Approved
0.5693 Remote Similarity NPD7266 Discontinued
0.5692 Remote Similarity NPD7260 Phase 2
0.5686 Remote Similarity NPD6435 Approved
0.5678 Remote Similarity NPD6421 Discontinued
0.5673 Remote Similarity NPD1733 Clinical (unspecified phase)
0.5669 Remote Similarity NPD6616 Approved
0.5656 Remote Similarity NPD7505 Discontinued
0.5648 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5645 Remote Similarity NPD6319 Approved
0.5645 Remote Similarity NPD6054 Approved
0.5645 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5634 Remote Similarity NPD8389 Clinical (unspecified phase)
0.5625 Remote Similarity NPD8293 Discontinued
0.5625 Remote Similarity NPD7078 Approved
0.5612 Remote Similarity NPD8039 Approved
0.5607 Remote Similarity NPD5370 Suspended
0.5604 Remote Similarity NPD8961 Approved
0.56 Remote Similarity NPD5784 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   44444957
ChEMBL   CHEMBL399664
ZINC  

Physicochemical Properties

Molecular Weight:  564.29
ALogP:  -0.374
MLogP:  3.66
XLogP:  2.164
# Rotatable Bonds:  9
Polar Surface Area:  162.98
# H-Bond Aceptor:  10
# H-Bond Donor:  5
# Rings:  2
# Heavy Atoms:  40

Download Data

Data Type Select
General Info & Identifiers & Properties  
Structure MOL file  
Source Organisms  
Biological Activities  
Similar NPs/Drugs