Natural Product: NPC474658

Natural Product ID:  NPC474658
Common Name:   Anthecotulide
IUPAC Name:   4-[(2E)-3,7-dimethyl-5-oxoocta-2,6-dienyl]-3-methylideneoxolan-2-one
Synonyms:   Anthecotulide
Molecular Formula:   C15H20O3
Standard InCHIKey:  WSKLYRKBPFVGEJ-VZUCSPMQSA-N
Standard InCHI:  InChI=1S/C15H20O3/c1-10(2)7-14(16)8-11(3)5-6-13-9-18-15(17)12(13)4/h5,7,13H,4,6,8-9H2,1-3H3/b11-5+
Canonical SMILES:  C/C(=CCC1COC(=O)C1=C)/CC(=O)C=C(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
NPO20111 Anthemis auriculata Species Asteraceae Eukaryota PMID[16643047]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT19 Organism Escherichia coli Escherichia coli MIC = 101000 nM 16488146
NPT172 Organism Proteus mirabilis Proteus mirabilis MIC = 202000 nM 16488146
NPT141 Organism Agrobacterium tumefaciens Agrobacterium tumefaciens MIC = 101000 nM 16488146
NPT18 Organism Pseudomonas aeruginosa Pseudomonas aeruginosa MIC = 202000 nM 11277765
NPT3729 Organism Pseudomonas tolaasii Pseudomonas tolaasii MIC = 202000 nM 11277765
NPT3608 Organism Salmonella enteritidis Salmonella enterica subsp. enterica serovar Enteritidis MIC = 202000 nM 11277765
NPT20 Organism Candida albicans Candida albicans MIC = 101000 nM 18808182
NPT314 Organism Bacillus cereus Bacillus cereus MIC = 51000 nM 17582775
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 51000 nM 17582775
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 101000 nM 17582775
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 101000 nM 20805391

  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 NPC474658 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
0.9206 High Similarity NPC470256
0.9062 High Similarity NPC476591
0.9062 High Similarity NPC88877
0.875 High Similarity NPC194871
0.8548 High Similarity NPC151648
0.8529 High Similarity NPC114727
0.8529 High Similarity NPC476590
0.8261 Intermediate Similarity NPC476355
0.8235 Intermediate Similarity NPC163003
0.8143 Intermediate Similarity NPC226669
0.8143 Intermediate Similarity NPC193351
0.8143 Intermediate Similarity NPC155587
0.8143 Intermediate Similarity NPC138408
0.8116 Intermediate Similarity NPC58956
0.8116 Intermediate Similarity NPC295633
0.8116 Intermediate Similarity NPC269206
0.8028 Intermediate Similarity NPC123360
0.8 Intermediate Similarity NPC140287
0.8 Intermediate Similarity NPC117746
0.8 Intermediate Similarity NPC259599
0.8 Intermediate Similarity NPC15499
0.8 Intermediate Similarity NPC294434
0.7945 Intermediate Similarity NPC472965
0.7945 Intermediate Similarity NPC63649
0.7945 Intermediate Similarity NPC270126
0.7945 Intermediate Similarity NPC264227
0.7917 Intermediate Similarity NPC187568
0.7917 Intermediate Similarity NPC65603
0.7917 Intermediate Similarity NPC41780
0.791 Intermediate Similarity NPC203335
0.7879 Intermediate Similarity NPC470688
0.7838 Intermediate Similarity NPC302426
0.7812 Intermediate Similarity NPC79756
0.7808 Intermediate Similarity NPC108816
0.7808 Intermediate Similarity NPC93763
0.7778 Intermediate Similarity NPC68819
0.7778 Intermediate Similarity NPC235906
0.7761 Intermediate Similarity NPC248125
0.7703 Intermediate Similarity NPC178277
0.7681 Intermediate Similarity NPC476059
0.7681 Intermediate Similarity NPC473603
0.7671 Intermediate Similarity NPC7563
0.7671 Intermediate Similarity NPC470240
0.7671 Intermediate Similarity NPC320630
0.7671 Intermediate Similarity NPC476794
0.7671 Intermediate Similarity NPC171204
0.7671 Intermediate Similarity NPC57744
0.7671 Intermediate Similarity NPC116177
0.7671 Intermediate Similarity NPC476028
0.7671 Intermediate Similarity NPC141789
0.7671 Intermediate Similarity NPC97516
0.7647 Intermediate Similarity NPC21998
0.7632 Intermediate Similarity NPC173609
0.7627 Intermediate Similarity NPC236338
0.7606 Intermediate Similarity NPC287878
0.76 Intermediate Similarity NPC69271
0.76 Intermediate Similarity NPC223904
0.76 Intermediate Similarity NPC281132
0.76 Intermediate Similarity NPC74673
0.7576 Intermediate Similarity NPC474774
0.7576 Intermediate Similarity NPC68110
0.7568 Intermediate Similarity NPC471465
0.7568 Intermediate Similarity NPC128276
0.7568 Intermediate Similarity NPC267231
0.7568 Intermediate Similarity NPC196653
0.7568 Intermediate Similarity NPC472960
0.7532 Intermediate Similarity NPC39588
0.75 Intermediate Similarity NPC10276
0.75 Intermediate Similarity NPC471325
0.75 Intermediate Similarity NPC25684
0.75 Intermediate Similarity NPC35089
0.75 Intermediate Similarity NPC301477
0.75 Intermediate Similarity NPC281949
0.75 Intermediate Similarity NPC474758
0.7467 Intermediate Similarity NPC617
0.7467 Intermediate Similarity NPC470244
0.7467 Intermediate Similarity NPC167881
0.7467 Intermediate Similarity NPC98557
0.7467 Intermediate Similarity NPC182550
0.7467 Intermediate Similarity NPC470239
0.7465 Intermediate Similarity NPC129665
0.7458 Intermediate Similarity NPC135698
0.7436 Intermediate Similarity NPC115786
0.7432 Intermediate Similarity NPC10572
0.7397 Intermediate Similarity NPC329852
0.7385 Intermediate Similarity NPC286189
0.7377 Intermediate Similarity NPC170167
0.7377 Intermediate Similarity NPC151919
0.7368 Intermediate Similarity NPC276356
0.7361 Intermediate Similarity NPC472956
0.7353 Intermediate Similarity NPC133904
0.7353 Intermediate Similarity NPC131174
0.7342 Intermediate Similarity NPC33570
0.7342 Intermediate Similarity NPC161957
0.7342 Intermediate Similarity NPC21471
0.7333 Intermediate Similarity NPC299235
0.7333 Intermediate Similarity NPC15789
0.7313 Intermediate Similarity NPC155849
0.7308 Intermediate Similarity NPC40746
0.7308 Intermediate Similarity NPC215294
0.7308 Intermediate Similarity NPC169575
0.7308 Intermediate Similarity NPC116543
0.7308 Intermediate Similarity NPC59097
0.7308 Intermediate Similarity NPC318468
0.7297 Intermediate Similarity NPC266159
0.7297 Intermediate Similarity NPC27205
0.7297 Intermediate Similarity NPC472967
0.7286 Intermediate Similarity NPC218477
0.7273 Intermediate Similarity NPC141810
0.7273 Intermediate Similarity NPC275507
0.7273 Intermediate Similarity NPC42470
0.7273 Intermediate Similarity NPC24417
0.725 Intermediate Similarity NPC107787
0.7237 Intermediate Similarity NPC473981
0.7237 Intermediate Similarity NPC473980
0.7237 Intermediate Similarity NPC99651
0.7222 Intermediate Similarity NPC257618
0.7215 Intermediate Similarity NPC141193
0.7215 Intermediate Similarity NPC96259
0.7213 Intermediate Similarity NPC244452
0.7213 Intermediate Similarity NPC148056
0.7206 Intermediate Similarity NPC34883
0.72 Intermediate Similarity NPC195785
0.72 Intermediate Similarity NPC15975
0.7188 Intermediate Similarity NPC252860
0.7183 Intermediate Similarity NPC475982
0.7183 Intermediate Similarity NPC296522
0.7183 Intermediate Similarity NPC144511
0.7183 Intermediate Similarity NPC265574
0.7183 Intermediate Similarity NPC470693
0.7179 Intermediate Similarity NPC229825
0.7179 Intermediate Similarity NPC178676
0.7162 Intermediate Similarity NPC244166
0.7162 Intermediate Similarity NPC478194
0.7162 Intermediate Similarity NPC478192
0.7162 Intermediate Similarity NPC478191
0.7162 Intermediate Similarity NPC478195
0.7162 Intermediate Similarity NPC478196
0.7162 Intermediate Similarity NPC478193
0.7143 Intermediate Similarity NPC472266
0.7125 Intermediate Similarity NPC470755
0.7125 Intermediate Similarity NPC165162
0.7125 Intermediate Similarity NPC110405
0.7125 Intermediate Similarity NPC78089
0.7125 Intermediate Similarity NPC215364
0.7105 Intermediate Similarity NPC471220
0.7105 Intermediate Similarity NPC475699
0.7105 Intermediate Similarity NPC253749
0.7101 Intermediate Similarity NPC182794
0.7101 Intermediate Similarity NPC220766
0.7097 Intermediate Similarity NPC216407
0.7089 Intermediate Similarity NPC22611
0.7089 Intermediate Similarity NPC250315
0.7089 Intermediate Similarity NPC170286
0.7089 Intermediate Similarity NPC131669
0.7089 Intermediate Similarity NPC475947
0.7089 Intermediate Similarity NPC272814
0.7089 Intermediate Similarity NPC473390
0.7083 Intermediate Similarity NPC469660
0.7083 Intermediate Similarity NPC202011
0.7083 Intermediate Similarity NPC472955
0.7083 Intermediate Similarity NPC67183
0.7083 Intermediate Similarity NPC318766
0.7073 Intermediate Similarity NPC215831
0.7067 Intermediate Similarity NPC472959
0.7067 Intermediate Similarity NPC473223
0.7059 Intermediate Similarity NPC179087
0.7059 Intermediate Similarity NPC44343
0.7059 Intermediate Similarity NPC322457
0.7059 Intermediate Similarity NPC210303
0.7059 Intermediate Similarity NPC473737
0.7051 Intermediate Similarity NPC325031
0.7049 Intermediate Similarity NPC289388
0.7049 Intermediate Similarity NPC27264
0.7042 Intermediate Similarity NPC276290
0.7042 Intermediate Similarity NPC287705
0.7037 Intermediate Similarity NPC284902
0.7037 Intermediate Similarity NPC475461
0.7037 Intermediate Similarity NPC38576
0.7037 Intermediate Similarity NPC150755
0.7037 Intermediate Similarity NPC279859
0.7037 Intermediate Similarity NPC305475
0.7015 Intermediate Similarity NPC19241
0.7013 Intermediate Similarity NPC469690
0.7013 Intermediate Similarity NPC471299
0.7 Intermediate Similarity NPC191233
0.7 Intermediate Similarity NPC158756
0.7 Intermediate Similarity NPC163615
0.7 Intermediate Similarity NPC114979
0.7 Intermediate Similarity NPC191476
0.7 Intermediate Similarity NPC38569
0.7 Intermediate Similarity NPC476804
0.6988 Remote Similarity NPC73995
0.6988 Remote Similarity NPC268298
0.6986 Remote Similarity NPC186531
0.6986 Remote Similarity NPC84038
0.6974 Remote Similarity NPC53581
0.6974 Remote Similarity NPC103987
0.6974 Remote Similarity NPC474760
0.697 Remote Similarity NPC478096

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC474658 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
0.7213 Intermediate Similarity NPD6927 Phase 3
0.6962 Remote Similarity NPD5209 Approved
0.6914 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6914 Remote Similarity NPD1694 Approved
0.6857 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6721 Remote Similarity NPD5343 Approved
0.6591 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6588 Remote Similarity NPD1695 Approved
0.6543 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6322 Remote Similarity NPD5785 Approved
0.6282 Remote Similarity NPD1452 Discontinued
0.623 Remote Similarity NPD6097 Approved
0.623 Remote Similarity NPD6096 Approved
0.6119 Remote Similarity NPD9298 Approved
0.6118 Remote Similarity NPD5363 Approved
0.6087 Remote Similarity NPD8779 Phase 3
0.6076 Remote Similarity NPD8039 Approved
0.6022 Remote Similarity NPD4225 Approved
0.5955 Remote Similarity NPD46 Approved
0.5955 Remote Similarity NPD6698 Approved
0.593 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5926 Remote Similarity NPD4756 Discovery
0.5904 Remote Similarity NPD4252 Approved
0.5904 Remote Similarity NPD5790 Clinical (unspecified phase)
0.5882 Remote Similarity NPD7154 Phase 3
0.5873 Remote Similarity NPD4222 Approved
0.5873 Remote Similarity NPD3174 Discontinued
0.5867 Remote Similarity NPD6108 Clinical (unspecified phase)
0.5862 Remote Similarity NPD7521 Approved
0.5862 Remote Similarity NPD5330 Approved
0.5862 Remote Similarity NPD7334 Approved
0.5862 Remote Similarity NPD6409 Approved
0.5862 Remote Similarity NPD6684 Approved
0.5862 Remote Similarity NPD7146 Approved
0.5833 Remote Similarity NPD5369 Approved
0.5814 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5811 Remote Similarity NPD5325 Clinical (unspecified phase)
0.5778 Remote Similarity NPD7838 Discovery
0.5775 Remote Similarity NPD6109 Phase 1
0.5765 Remote Similarity NPD4269 Approved
0.5765 Remote Similarity NPD4270 Approved
0.5758 Remote Similarity NPD7899 Clinical (unspecified phase)
0.573 Remote Similarity NPD6672 Approved
0.573 Remote Similarity NPD6903 Approved
0.573 Remote Similarity NPD5737 Approved
0.573 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5714 Remote Similarity NPD5693 Phase 1
0.5698 Remote Similarity NPD5362 Discontinued
0.5684 Remote Similarity NPD8029 Clinical (unspecified phase)
0.5682 Remote Similarity NPD4249 Approved
0.5682 Remote Similarity NPD5786 Approved
0.5667 Remote Similarity NPD5783 Phase 3
0.5663 Remote Similarity NPD4268 Approved
0.5663 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5663 Remote Similarity NPD4271 Approved
0.5618 Remote Similarity NPD4251 Approved
0.5618 Remote Similarity NPD4250 Approved
0.5616 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5606 Remote Similarity NPD3173 Approved
0.5606 Remote Similarity NPD4220 Pre-registration
0.5604 Remote Similarity NPD5207 Approved

Structure

External Identifiers

PubChem CID   11962174
ChEMBL   CHEMBL478602
ZINC  

Physicochemical Properties

Molecular Weight:  248.14
ALogP:  2.3234
MLogP:  2.78
XLogP:  1.904
# Rotatable Bonds:  8
Polar Surface Area:  43.37
# H-Bond Aceptor:  3
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  18

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