Natural Product: NPC24389

Natural Product ID:  NPC24389
Common Name:   Tirandamycin D
IUPAC Name:   (3E)-3-[(2E,4E,6R)-1-hydroxy-4-methyl-6-[(1S,5S,7R,8R)-4,5,8-trimethyl-2-oxo-6,9-dioxabicyclo[3.3.1]non-3-en-7-yl]hepta-2,4-dienylidene]pyrrolidine-2,4-dione
Synonyms:   Tirandamycin D
Molecular Formula:   C22H27NO6
Standard InCHIKey:  WORJTWSOUPGODS-KFBBACJUSA-N
Standard InCHI:  InChI=1S/C22H27NO6/c1-11(6-7-15(24)18-17(26)10-23-21(18)27)8-12(2)19-14(4)20-16(25)9-13(3)22(5,28-19)29-20/h6-9,12,14,19-20,24H,10H2,1-5H3,(H,23,27)/b7-6+,11-8+,18-15+/t12-,14-,19-,20+,22+/m1/s1
Canonical SMILES:  C/C(=C[C@H]([C@H]1O[C@@]2(C)O[C@@H]([C@@H]1C)C(=O)C=C2C)C)/C=C/C(=C1/C(=O)CN=C1O)/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
NPO30376 Streptomyces sp. Species Streptomycetaceae Bacteria PMID[19883065]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT175 Organism Enterococcus faecalis Enterococcus faecalis MIC > 9000 nM 23368966

  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 NPC24389 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
0.93 High Similarity NPC175531
0.8509 High Similarity NPC469515
0.8291 Intermediate Similarity NPC469494
0.7706 Intermediate Similarity NPC313234
0.7182 Intermediate Similarity NPC121857
0.7117 Intermediate Similarity NPC167380
0.708 Intermediate Similarity NPC469851
0.7059 Intermediate Similarity NPC469865
0.7016 Intermediate Similarity NPC315915
0.6975 Remote Similarity NPC170375
0.6967 Remote Similarity NPC476190
0.6967 Remote Similarity NPC27413
0.6967 Remote Similarity NPC271621
0.6967 Remote Similarity NPC59751
0.6891 Remote Similarity NPC476290
0.6864 Remote Similarity NPC475150
0.6838 Remote Similarity NPC469852
0.6832 Remote Similarity NPC263266
0.6829 Remote Similarity NPC316325
0.6818 Remote Similarity NPC32552
0.6807 Remote Similarity NPC473578
0.68 Remote Similarity NPC473808
0.678 Remote Similarity NPC469853
0.6777 Remote Similarity NPC476269
0.6774 Remote Similarity NPC296361
0.6748 Remote Similarity NPC315652
0.6748 Remote Similarity NPC7905
0.6742 Remote Similarity NPC314361
0.6727 Remote Similarity NPC475879
0.6724 Remote Similarity NPC469598
0.6724 Remote Similarity NPC128501
0.6721 Remote Similarity NPC5485
0.6698 Remote Similarity NPC16488
0.6692 Remote Similarity NPC329919
0.6692 Remote Similarity NPC477793
0.6667 Remote Similarity NPC316426
0.6667 Remote Similarity NPC476814
0.6667 Remote Similarity NPC476813
0.6667 Remote Similarity NPC315395
0.6612 Remote Similarity NPC127578
0.6583 Remote Similarity NPC307903
0.6583 Remote Similarity NPC140251
0.6583 Remote Similarity NPC327106
0.6574 Remote Similarity NPC281172
0.6555 Remote Similarity NPC271269
0.6535 Remote Similarity NPC473145
0.6525 Remote Similarity NPC474563
0.6522 Remote Similarity NPC315210
0.6522 Remote Similarity NPC315848
0.6518 Remote Similarity NPC166110
0.6518 Remote Similarity NPC472264
0.6514 Remote Similarity NPC291712
0.65 Remote Similarity NPC251330
0.6491 Remote Similarity NPC473334
0.6475 Remote Similarity NPC89408
0.6471 Remote Similarity NPC472616
0.646 Remote Similarity NPC248193
0.646 Remote Similarity NPC282644
0.646 Remote Similarity NPC29798
0.6457 Remote Similarity NPC245320
0.6449 Remote Similarity NPC469833
0.6449 Remote Similarity NPC469838
0.6446 Remote Similarity NPC471636
0.6446 Remote Similarity NPC287572
0.6444 Remote Similarity NPC78189
0.6435 Remote Similarity NPC175614
0.6435 Remote Similarity NPC475503
0.6423 Remote Similarity NPC230889
0.6417 Remote Similarity NPC472615
0.6417 Remote Similarity NPC154601
0.6408 Remote Similarity NPC315552
0.6406 Remote Similarity NPC31641
0.6406 Remote Similarity NPC477140
0.6406 Remote Similarity NPC477143
0.6404 Remote Similarity NPC121825
0.6404 Remote Similarity NPC143210
0.6404 Remote Similarity NPC471496
0.6396 Remote Similarity NPC106051
0.6385 Remote Similarity NPC16709
0.6379 Remote Similarity NPC208094
0.6379 Remote Similarity NPC476344
0.6379 Remote Similarity NPC265662
0.6372 Remote Similarity NPC32944
0.6372 Remote Similarity NPC193396
0.6364 Remote Similarity NPC261721
0.6364 Remote Similarity NPC199107
0.6364 Remote Similarity NPC232969
0.6356 Remote Similarity NPC244456
0.6356 Remote Similarity NPC469657
0.6348 Remote Similarity NPC150041
0.6348 Remote Similarity NPC12727
0.6348 Remote Similarity NPC295347
0.6339 Remote Similarity NPC95364
0.6339 Remote Similarity NPC471054
0.6339 Remote Similarity NPC142159
0.6333 Remote Similarity NPC133420
0.6316 Remote Similarity NPC469692
0.6316 Remote Similarity NPC475098
0.6316 Remote Similarity NPC469645
0.6316 Remote Similarity NPC189651
0.6306 Remote Similarity NPC476079
0.6306 Remote Similarity NPC103743
0.6306 Remote Similarity NPC241054
0.6306 Remote Similarity NPC45409
0.6306 Remote Similarity NPC113370
0.6303 Remote Similarity NPC197835
0.6303 Remote Similarity NPC189609
0.6303 Remote Similarity NPC303653
0.6303 Remote Similarity NPC291500
0.6303 Remote Similarity NPC140591
0.6299 Remote Similarity NPC243298
0.6293 Remote Similarity NPC195645
0.6293 Remote Similarity NPC165332
0.6293 Remote Similarity NPC180722
0.629 Remote Similarity NPC29501
0.629 Remote Similarity NPC21713
0.629 Remote Similarity NPC475608
0.6283 Remote Similarity NPC477865
0.6283 Remote Similarity NPC477866
0.6281 Remote Similarity NPC101106
0.6281 Remote Similarity NPC472433
0.6281 Remote Similarity NPC135216
0.6279 Remote Similarity NPC476815
0.6277 Remote Similarity NPC472428
0.6273 Remote Similarity NPC307112
0.6273 Remote Similarity NPC471223
0.6273 Remote Similarity NPC67081
0.627 Remote Similarity NPC471645
0.6261 Remote Similarity NPC477241
0.6261 Remote Similarity NPC470521
0.6261 Remote Similarity NPC469632
0.626 Remote Similarity NPC133729
0.626 Remote Similarity NPC474891
0.625 Remote Similarity NPC472011
0.625 Remote Similarity NPC199831
0.625 Remote Similarity NPC474827
0.625 Remote Similarity NPC473658
0.625 Remote Similarity NPC68001
0.625 Remote Similarity NPC474828
0.625 Remote Similarity NPC26078
0.6241 Remote Similarity NPC473249
0.6241 Remote Similarity NPC68293
0.6241 Remote Similarity NPC262845
0.624 Remote Similarity NPC66108
0.624 Remote Similarity NPC295444
0.624 Remote Similarity NPC273215
0.624 Remote Similarity NPC268327
0.6239 Remote Similarity NPC475083
0.6239 Remote Similarity NPC471462
0.6239 Remote Similarity NPC4834
0.6239 Remote Similarity NPC266842
0.6239 Remote Similarity NPC475646
0.6232 Remote Similarity NPC472430
0.623 Remote Similarity NPC250187
0.6228 Remote Similarity NPC470520
0.6218 Remote Similarity NPC316250
0.6218 Remote Similarity NPC224172
0.6218 Remote Similarity NPC472643
0.6214 Remote Similarity NPC316851
0.621 Remote Similarity NPC477997
0.621 Remote Similarity NPC113012
0.621 Remote Similarity NPC122926
0.6207 Remote Similarity NPC205546
0.6207 Remote Similarity NPC189764
0.6207 Remote Similarity NPC233273
0.6207 Remote Similarity NPC209355
0.6207 Remote Similarity NPC50902
0.6198 Remote Similarity NPC14537
0.6195 Remote Similarity NPC51358
0.6195 Remote Similarity NPC307092
0.619 Remote Similarity NPC475988
0.6186 Remote Similarity NPC35717
0.6186 Remote Similarity NPC234542
0.6182 Remote Similarity NPC31086
0.6179 Remote Similarity NPC476034
0.6179 Remote Similarity NPC474099
0.6179 Remote Similarity NPC474969
0.6174 Remote Similarity NPC59646
0.6174 Remote Similarity NPC242069
0.6174 Remote Similarity NPC320552
0.6172 Remote Similarity NPC475642
0.6161 Remote Similarity NPC316138
0.6161 Remote Similarity NPC472007
0.6161 Remote Similarity NPC313658
0.6161 Remote Similarity NPC23622
0.6148 Remote Similarity NPC472645
0.6148 Remote Similarity NPC472751
0.6148 Remote Similarity NPC472749
0.6148 Remote Similarity NPC473252
0.614 Remote Similarity NPC3436
0.614 Remote Similarity NPC475995
0.614 Remote Similarity NPC474098
0.614 Remote Similarity NPC327253
0.6134 Remote Similarity NPC473224
0.6132 Remote Similarity NPC82666
0.6132 Remote Similarity NPC471225
0.6132 Remote Similarity NPC97173
0.6129 Remote Similarity NPC133625
0.6129 Remote Similarity NPC298484
0.6129 Remote Similarity NPC38154

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC24389 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
0.6975 Remote Similarity NPD7601 Clinical (unspecified phase)
0.6829 Remote Similarity NPD7500 Approved
0.6694 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6591 Remote Similarity NPD6914 Discontinued
0.6484 Remote Similarity NPD7739 Clinical (unspecified phase)
0.6434 Remote Similarity NPD7624 Clinical (unspecified phase)
0.6434 Remote Similarity NPD7623 Phase 3
0.6293 Remote Similarity NPD7839 Suspended
0.6281 Remote Similarity NPD4211 Phase 1
0.6241 Remote Similarity NPD7747 Phase 1
0.6241 Remote Similarity NPD7746 Phase 1
0.6154 Remote Similarity NPD4228 Discovery
0.6154 Remote Similarity NPD7299 Clinical (unspecified phase)
0.6129 Remote Similarity NPD6413 Approved
0.6119 Remote Similarity NPD8074 Phase 3
0.605 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6047 Remote Similarity NPD7505 Discontinued
0.6036 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6015 Remote Similarity NPD7829 Approved
0.6015 Remote Similarity NPD7830 Approved
0.5983 Remote Similarity NPD5282 Discontinued
0.5952 Remote Similarity NPD6420 Discontinued
0.594 Remote Similarity NPD8080 Discontinued
0.5926 Remote Similarity NPD8451 Approved
0.5906 Remote Similarity NPD8413 Clinical (unspecified phase)
0.5896 Remote Similarity NPD7642 Approved
0.5882 Remote Similarity NPD8448 Approved
0.5878 Remote Similarity NPD7641 Discontinued
0.587 Remote Similarity NPD8391 Approved
0.587 Remote Similarity NPD8390 Approved
0.587 Remote Similarity NPD8392 Approved
0.5865 Remote Similarity NPD8444 Approved
0.5862 Remote Similarity NPD5785 Approved
0.5852 Remote Similarity NPD8341 Approved
0.5852 Remote Similarity NPD8340 Approved
0.5852 Remote Similarity NPD8342 Approved
0.5852 Remote Similarity NPD8299 Approved
0.5827 Remote Similarity NPD7260 Phase 2
0.5781 Remote Similarity NPD2204 Approved
0.5781 Remote Similarity NPD1719 Phase 1
0.5763 Remote Similarity NPD5779 Approved
0.5763 Remote Similarity NPD5778 Approved
0.5746 Remote Similarity NPD8513 Phase 3
0.5746 Remote Similarity NPD8274 Clinical (unspecified phase)
0.5726 Remote Similarity NPD1407 Approved
0.5714 Remote Similarity NPD5209 Approved
0.5704 Remote Similarity NPD8415 Approved
0.5704 Remote Similarity NPD2838 Clinical (unspecified phase)
0.5703 Remote Similarity NPD6421 Discontinued
0.5702 Remote Similarity NPD5363 Approved
0.5688 Remote Similarity NPD4756 Discovery
0.5678 Remote Similarity NPD7637 Suspended
0.5676 Remote Similarity NPD8259 Clinical (unspecified phase)
0.5667 Remote Similarity NPD1698 Clinical (unspecified phase)
0.5664 Remote Similarity NPD7154 Phase 3
0.5664 Remote Similarity NPD8387 Clinical (unspecified phase)
0.5656 Remote Similarity NPD4225 Approved
0.5641 Remote Similarity NPD6101 Approved
0.5641 Remote Similarity NPD5764 Clinical (unspecified phase)
0.563 Remote Similarity NPD5781 Clinical (unspecified phase)
0.563 Remote Similarity NPD8516 Approved
0.563 Remote Similarity NPD8515 Approved
0.563 Remote Similarity NPD8517 Approved

Structure

External Identifiers

PubChem CID   54728537
ChEMBL   CHEMBL1079496
ZINC  

Physicochemical Properties

Molecular Weight:  401.18
ALogP:  0.91
MLogP:  3.11
XLogP:  1.808
# Rotatable Bonds:  11
Polar Surface Area:  105.42
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  29

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs