Natural Product: NPC52587

Natural Product ID:  NPC52587
Common Name:   Epothilone A9
IUPAC Name:   (1R,5S,6S,7R,10S,14S,16S)-6,10-dihydroxy-14-[(E)-3-hydroxy-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-5,7,9,9-tetramethyl-13,17-dioxabicyclo[14.1.0]heptadecane-8,12-dione
Synonyms:   Epothilone A9
Molecular Formula:   C26H39NO7S
Standard InCHIKey:  XSZHNNYJIPRFJZ-MSYOXSAWSA-N
Standard InCHI:  InChI=1S/C26H39NO7S/c1-14-7-6-8-19-21(33-19)10-20(17(12-28)9-18-13-35-16(3)27-18)34-23(30)11-22(29)26(4,5)25(32)15(2)24(14)31/h9,13-15,19-22,24,28-29,31H,6-8,10-12H2,1-5H3/b17-9+/t14-,15+,19+,20-,21-,22-,24-/m0/s1
Canonical SMILES:  OC/C(=Cc1csc(n1)C)/[C@H]1OC(=O)C[C@H](O)C(C)(C)C(=O)[C@H](C)[C@H]([C@H](CCC[C@@H]2[C@H](C1)O2)C)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
NPO32627 sorangium cellulosum, strains so ce90/b2 Species Polyangiaceae Bacteria PMID[11473410]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1460 Cell Line L929 Mus musculus IC50 = 0.1 ug/ml 18357994

  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 NPC52587 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
0.9862 High Similarity NPC212214
0.9795 High Similarity NPC21126
0.9728 High Similarity NPC474538
0.9726 High Similarity NPC202591
0.9724 High Similarity NPC474515
0.9724 High Similarity NPC206724
0.9662 High Similarity NPC231110
0.9597 High Similarity NPC312887
0.9589 High Similarity NPC154873
0.9524 High Similarity NPC268063
0.9524 High Similarity NPC224609
0.9521 High Similarity NPC475737
0.9521 High Similarity NPC474094
0.9521 High Similarity NPC185665
0.9456 High Similarity NPC474090
0.9456 High Similarity NPC61667
0.9456 High Similarity NPC45576
0.9456 High Similarity NPC109498
0.9456 High Similarity NPC252616
0.9456 High Similarity NPC32583
0.9456 High Similarity NPC163147
0.9388 High Similarity NPC474067
0.9384 High Similarity NPC474103
0.9384 High Similarity NPC474068
0.9384 High Similarity NPC474064
0.9384 High Similarity NPC82436
0.9333 High Similarity NPC127775
0.932 High Similarity NPC474080
0.932 High Similarity NPC474102
0.932 High Similarity NPC474079
0.932 High Similarity NPC157194
0.932 High Similarity NPC475683
0.932 High Similarity NPC21449
0.9048 High Similarity NPC474069
0.8435 Intermediate Similarity NPC474070
0.7959 Intermediate Similarity NPC475604
0.7755 Intermediate Similarity NPC475568
0.7262 Intermediate Similarity NPC315252
0.7222 Intermediate Similarity NPC190329
0.7151 Intermediate Similarity NPC12660
0.711 Intermediate Similarity NPC54983
0.6994 Remote Similarity NPC469801
0.697 Remote Similarity NPC319751
0.6919 Remote Similarity NPC186452
0.6879 Remote Similarity NPC211555
0.6845 Remote Similarity NPC119481
0.6786 Remote Similarity NPC473398
0.678 Remote Similarity NPC101980
0.678 Remote Similarity NPC470146
0.678 Remote Similarity NPC97078
0.6497 Remote Similarity NPC522
0.6497 Remote Similarity NPC56058
0.6374 Remote Similarity NPC164006
0.6321 Remote Similarity NPC165538
0.6302 Remote Similarity NPC122427
0.6233 Remote Similarity NPC469858
0.6222 Remote Similarity NPC210424
0.6218 Remote Similarity NPC329961
0.6209 Remote Similarity NPC475554
0.6203 Remote Similarity NPC132662
0.6167 Remote Similarity NPC216720
0.6096 Remote Similarity NPC473704
0.6054 Remote Similarity NPC24990
0.6043 Remote Similarity NPC134480
0.6019 Remote Similarity NPC14877
0.6019 Remote Similarity NPC475350
0.6019 Remote Similarity NPC145178
0.5978 Remote Similarity NPC14101
0.5947 Remote Similarity NPC161242
0.5933 Remote Similarity NPC251036
0.5864 Remote Similarity NPC476080
0.5864 Remote Similarity NPC475534
0.5852 Remote Similarity NPC475390
0.5851 Remote Similarity NPC476103
0.5803 Remote Similarity NPC229160
0.5803 Remote Similarity NPC25316
0.5803 Remote Similarity NPC263485
0.5775 Remote Similarity NPC473886
0.5771 Remote Similarity NPC106235
0.5771 Remote Similarity NPC239660
0.5751 Remote Similarity NPC475330
0.5722 Remote Similarity NPC174652
0.5695 Remote Similarity NPC475196
0.5663 Remote Similarity NPC161143
0.5648 Remote Similarity NPC475455
0.5632 Remote Similarity NPC30527

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC52587 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
0.9795 High Similarity NPD6910 Phase 3
0.9527 High Similarity NPD6911 Discontinued
0.9521 High Similarity NPD6907 Phase 2
0.9286 High Similarity NPD6916 Clinical (unspecified phase)
0.8581 High Similarity NPD6915 Approved
0.7231 Intermediate Similarity NPD7496 Phase 2
0.6344 Remote Similarity NPD2957 Phase 2
0.6307 Remote Similarity NPD5189 Clinical (unspecified phase)
0.6236 Remote Similarity NPD5634 Approved
0.6051 Remote Similarity NPD6348 Clinical (unspecified phase)
0.6012 Remote Similarity NPD1083 Clinical (unspecified phase)
0.5918 Remote Similarity NPD6349 Phase 1
0.582 Remote Similarity NPD6870 Phase 1
0.5771 Remote Similarity NPD8339 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   11092425
ChEMBL   CHEMBL512170
ZINC  

Physicochemical Properties

Molecular Weight:  509.24
ALogP:  -0.4474
MLogP:  3.33
XLogP:  1.47
# Rotatable Bonds:  11
Polar Surface Area:  157.72
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  35

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs