Natural Product: NPC186452

Natural Product ID:  NPC186452
Common Name:   Epothilone H2
IUPAC Name:   (4S,7R,8S,9S,13Z,16S)-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-(2-methyl-1,3-oxazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadec-13-ene-2,6-dione
Synonyms:   Epothilone H2
Molecular Formula:   C27H41NO6
Standard InCHIKey:  QJBTYCVYJKZKMC-GIQCAXHBSA-N
Standard InCHI:  InChI=1S/C27H41NO6/c1-16-9-8-10-17(2)25(31)19(4)26(32)27(6,7)23(29)14-24(30)34-22(12-11-16)18(3)13-21-15-33-20(5)28-21/h11,13,15,17,19,22-23,25,29,31H,8-10,12,14H2,1-7H3/b16-11-,18-13+/t17-,19+,22-,23-,25-/m0/s1
Canonical SMILES:  O=C1O[C@@H](C/C=C(/C)CCC[C@@H]([C@@H]([C@H](C(=O)C([C@H](C1)O)(C)C)C)O)C)/C(=C/c1coc(n1)C)/C
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 = 0.011 ug/ml 10.1039/C3MD00094J

  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 NPC186452 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
0.9932 High Similarity NPC211555
0.9733 High Similarity NPC12660
0.9669 High Similarity NPC54983
0.7844 Intermediate Similarity NPC30527
0.7719 Intermediate Similarity NPC475455
0.7401 Intermediate Similarity NPC58001
0.7401 Intermediate Similarity NPC314523
0.7229 Intermediate Similarity NPC475737
0.7229 Intermediate Similarity NPC185665
0.7229 Intermediate Similarity NPC474094
0.7186 Intermediate Similarity NPC45576
0.7186 Intermediate Similarity NPC163147
0.7186 Intermediate Similarity NPC32583
0.7186 Intermediate Similarity NPC154873
0.7186 Intermediate Similarity NPC109498
0.7186 Intermediate Similarity NPC252616
0.7186 Intermediate Similarity NPC474090
0.7186 Intermediate Similarity NPC61667
0.7181 Intermediate Similarity NPC476829
0.7176 Intermediate Similarity NPC231110
0.7143 Intermediate Similarity NPC224609
0.7143 Intermediate Similarity NPC268063
0.7135 Intermediate Similarity NPC312887
0.7126 Intermediate Similarity NPC474067
0.7108 Intermediate Similarity NPC82436
0.7108 Intermediate Similarity NPC474103
0.7108 Intermediate Similarity NPC474068
0.7108 Intermediate Similarity NPC474064
0.7066 Intermediate Similarity NPC474080
0.7066 Intermediate Similarity NPC474079
0.7066 Intermediate Similarity NPC21449
0.7066 Intermediate Similarity NPC474102
0.7066 Intermediate Similarity NPC157194
0.7066 Intermediate Similarity NPC475683
0.7018 Intermediate Similarity NPC127775
0.7 Intermediate Similarity NPC212214
0.6959 Remote Similarity NPC21126
0.6919 Remote Similarity NPC52587
0.6919 Remote Similarity NPC474538
0.6901 Remote Similarity NPC202591
0.6882 Remote Similarity NPC206724
0.6882 Remote Similarity NPC474515
0.6826 Remote Similarity NPC474069
0.6524 Remote Similarity NPC476828
0.648 Remote Similarity NPC208297
0.648 Remote Similarity NPC224395
0.6459 Remote Similarity NPC476831
0.6459 Remote Similarity NPC476826
0.6459 Remote Similarity NPC476827
0.6445 Remote Similarity NPC325683
0.6429 Remote Similarity NPC477219
0.6429 Remote Similarity NPC476830
0.6398 Remote Similarity NPC37924
0.6368 Remote Similarity NPC476832
0.6345 Remote Similarity NPC295653
0.6345 Remote Similarity NPC107458
0.6326 Remote Similarity NPC322800
0.6326 Remote Similarity NPC168135
0.6287 Remote Similarity NPC258022
0.6284 Remote Similarity NPC477589
0.6284 Remote Similarity NPC477587
0.6279 Remote Similarity NPC177432
0.6279 Remote Similarity NPC299035
0.625 Remote Similarity NPC477218
0.6227 Remote Similarity NPC477590
0.6227 Remote Similarity NPC477586
0.6227 Remote Similarity NPC477588
0.6227 Remote Similarity NPC477585
0.6224 Remote Similarity NPC58112
0.6224 Remote Similarity NPC306300
0.6224 Remote Similarity NPC88938
0.622 Remote Similarity NPC309919
0.619 Remote Similarity NPC474070
0.6143 Remote Similarity NPC49195
0.6091 Remote Similarity NPC199461
0.6091 Remote Similarity NPC103452
0.6091 Remote Similarity NPC46313
0.604 Remote Similarity NPC48323
0.604 Remote Similarity NPC289029
0.5808 Remote Similarity NPC72715
0.5774 Remote Similarity NPC475604
0.5625 Remote Similarity NPC209981

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC186452 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
0.7229 Intermediate Similarity NPD6907 Phase 2
0.7059 Intermediate Similarity NPD6347 Phase 2
0.6959 Remote Similarity NPD6910 Phase 3
0.6931 Remote Similarity NPD7490 Discontinued
0.686 Remote Similarity NPD6911 Discontinued
0.6649 Remote Similarity NPD7896 Approved
0.6648 Remote Similarity NPD6916 Clinical (unspecified phase)
0.6346 Remote Similarity NPD6974 Phase 3
0.6311 Remote Similarity NPD4667 Clinical (unspecified phase)
0.6145 Remote Similarity NPD6915 Approved
0.6129 Remote Similarity NPD6870 Phase 1
0.6089 Remote Similarity NPD2779 Approved
0.602 Remote Similarity NPD6857 Phase 3
0.5972 Remote Similarity NPD2433 Clinical (unspecified phase)
0.5943 Remote Similarity NPD5443 Clinical (unspecified phase)
0.5941 Remote Similarity NPD2778 Approved
0.5926 Remote Similarity NPD7547 Clinical (unspecified phase)
0.5924 Remote Similarity NPD1638 Discovery
0.5864 Remote Similarity NPD4898 Clinical (unspecified phase)
0.5804 Remote Similarity NPD7853 Phase 2
0.5787 Remote Similarity NPD7180 Phase 3
0.5695 Remote Similarity NPD7284 Clinical (unspecified phase)
0.5695 Remote Similarity NPD1867 Approved
0.566 Remote Similarity NPD2081 Clinical (unspecified phase)
0.5654 Remote Similarity NPD3945 Discontinued
0.5637 Remote Similarity NPD5512 Phase 3
0.5628 Remote Similarity NPD6169 Phase 1
0.5614 Remote Similarity NPD4394 Clinical (unspecified phase)
0.5611 Remote Similarity NPD6247 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   9804980
ChEMBL   CHEMBL471687
ZINC  

Physicochemical Properties

Molecular Weight:  475.29
ALogP:  1.9617
MLogP:  3.66
XLogP:  3.127
# Rotatable Bonds:  11
Polar Surface Area:  109.86
# H-Bond Aceptor:  6
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  34

Download Data

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Similar NPs/Drugs