Natural Product: NPC156681

Natural Product ID:  NPC156681
Common Name:   8Alpha-O-(3,4-Dihydroxy-2-Methylenebutanoyloxy)-15-Oxo-5,7Alphah,6Betah-Eleman-1,3,11(13)-Trien-6,12-Olide
IUPAC Name:   [(3aR,4S,6S,7R,7aR)-6-ethenyl-6-methyl-3-methylidene-2-oxo-7-(3-oxoprop-1-en-2-yl)-4,5,7,7a-tetrahydro-3aH-1-benzofuran-4-yl] (3R)-3,4-dihydroxy-2-methylidenebutanoate
Synonyms:  
Molecular Formula:   C20H24O7
Standard InCHIKey:  UKOKIVWGORCEQR-XFNMEUKGSA-N
Standard InCHI:  InChI=1S/C20H24O7/c1-6-20(5)7-14(26-18(24)11(3)13(23)9-22)15-12(4)19(25)27-17(15)16(20)10(2)8-21/h6,8,13-17,22-23H,1-4,7,9H2,5H3/t13-,14-,15+,16+,17-,20+/m0/s1
Canonical SMILES:  OC[C@@H](C(=C)C(=O)O[C@H]1C[C@@](C)(C=C)[C@@H]([C@@H]2[C@@H]1C(=C)C(=O)O2)C(=C)C=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
NPO21525 Centaurea spinosa Species Asteraceae Eukaryota PMID[16180824]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens GI50 = 10000 nM 17279798
NPT395 Cell Line SF-268 Homo sapiens GI50 = 7700 nM 17279798
NPT377 Cell Line OVCAR-3 Homo sapiens GI50 = 4700 nM 1593282
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 0.625 ug/ml 25856683
NPT314 Organism Bacillus cereus Bacillus cereus MIC = 1.25 ug/ml 9644084
NPT397 Cell Line NCI-H460 Homo sapiens GI50 = 37000 nM 26048785
NPT395 Cell Line SF-268 Homo sapiens TGI = 38000 nM 26200131
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 5 ug/ml 18991460

  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 NPC156681 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
0.9789 High Similarity NPC308824
0.9368 High Similarity NPC284518
0.93 High Similarity NPC78966
0.93 High Similarity NPC284732
0.9286 High Similarity NPC164551
0.9271 High Similarity NPC474395
0.9208 High Similarity NPC37628
0.9184 High Similarity NPC242666
0.899 High Similarity NPC111292
0.8932 High Similarity NPC474243
0.8866 High Similarity NPC259042
0.8866 High Similarity NPC157686
0.8842 High Similarity NPC153853
0.8812 High Similarity NPC99510
0.8812 High Similarity NPC72842
0.8788 High Similarity NPC476807
0.8788 High Similarity NPC476806
0.8776 High Similarity NPC228766
0.8776 High Similarity NPC165528
0.8763 High Similarity NPC225474
0.8763 High Similarity NPC148000
0.8763 High Similarity NPC469596
0.8763 High Similarity NPC24861
0.87 High Similarity NPC47024
0.8687 High Similarity NPC473963
0.8627 High Similarity NPC61442
0.86 High Similarity NPC216478
0.8586 High Similarity NPC93245
0.8586 High Similarity NPC473964
0.8571 High Similarity NPC473434
0.8571 High Similarity NPC474841
0.8571 High Similarity NPC471446
0.8544 High Similarity NPC283850
0.8454 Intermediate Similarity NPC475776
0.8365 Intermediate Similarity NPC296950
0.8365 Intermediate Similarity NPC146731
0.8351 Intermediate Similarity NPC116620
0.8351 Intermediate Similarity NPC194642
0.8333 Intermediate Similarity NPC477655
0.8333 Intermediate Similarity NPC477656
0.8317 Intermediate Similarity NPC136781
0.8302 Intermediate Similarity NPC306265
0.8269 Intermediate Similarity NPC159533
0.8257 Intermediate Similarity NPC477126
0.8252 Intermediate Similarity NPC475958
0.8224 Intermediate Similarity NPC42662
0.8208 Intermediate Similarity NPC187435
0.8208 Intermediate Similarity NPC67321
0.8198 Intermediate Similarity NPC469684
0.8165 Intermediate Similarity NPC269530
0.8165 Intermediate Similarity NPC476801
0.8148 Intermediate Similarity NPC235014
0.8148 Intermediate Similarity NPC5103
0.8144 Intermediate Similarity NPC305029
0.8144 Intermediate Similarity NPC470012
0.8144 Intermediate Similarity NPC175293
0.8144 Intermediate Similarity NPC181103
0.8131 Intermediate Similarity NPC476802
0.8131 Intermediate Similarity NPC89171
0.8125 Intermediate Similarity NPC284707
0.8119 Intermediate Similarity NPC90014
0.8108 Intermediate Similarity NPC270478
0.8095 Intermediate Similarity NPC120321
0.8091 Intermediate Similarity NPC56448
0.8058 Intermediate Similarity NPC124512
0.8058 Intermediate Similarity NPC159763
0.8058 Intermediate Similarity NPC278386
0.8041 Intermediate Similarity NPC185638
0.8041 Intermediate Similarity NPC477920
0.8041 Intermediate Similarity NPC85698
0.8036 Intermediate Similarity NPC98249
0.8036 Intermediate Similarity NPC53396
0.8 Intermediate Similarity NPC476081
0.8 Intermediate Similarity NPC186363
0.8 Intermediate Similarity NPC473877
0.8 Intermediate Similarity NPC233345
0.798 Intermediate Similarity NPC253618
0.798 Intermediate Similarity NPC77001
0.7963 Intermediate Similarity NPC112895
0.7963 Intermediate Similarity NPC94377
0.7963 Intermediate Similarity NPC273155
0.7963 Intermediate Similarity NPC218123
0.7963 Intermediate Similarity NPC231278
0.7961 Intermediate Similarity NPC70145
0.7961 Intermediate Similarity NPC91695
0.7961 Intermediate Similarity NPC111348
0.7961 Intermediate Similarity NPC474921
0.7928 Intermediate Similarity NPC478212
0.7928 Intermediate Similarity NPC469496
0.7928 Intermediate Similarity NPC469454
0.7928 Intermediate Similarity NPC469463
0.7925 Intermediate Similarity NPC474165
0.7925 Intermediate Similarity NPC69171
0.7925 Intermediate Similarity NPC96217
0.7921 Intermediate Similarity NPC199543
0.7921 Intermediate Similarity NPC147272
0.7913 Intermediate Similarity NPC67569
0.7909 Intermediate Similarity NPC304180
0.7909 Intermediate Similarity NPC157476
0.7909 Intermediate Similarity NPC179798
0.7909 Intermediate Similarity NPC94650
0.7905 Intermediate Similarity NPC303559
0.7905 Intermediate Similarity NPC46848
0.7905 Intermediate Similarity NPC98225
0.7905 Intermediate Similarity NPC148279
0.79 Intermediate Similarity NPC158488
0.7895 Intermediate Similarity NPC38642
0.7885 Intermediate Similarity NPC316598
0.7885 Intermediate Similarity NPC78427
0.7885 Intermediate Similarity NPC16911
0.7876 Intermediate Similarity NPC475323
0.7876 Intermediate Similarity NPC58662
0.7876 Intermediate Similarity NPC473656
0.787 Intermediate Similarity NPC166993
0.787 Intermediate Similarity NPC143609
0.7864 Intermediate Similarity NPC234993
0.7864 Intermediate Similarity NPC242848
0.7864 Intermediate Similarity NPC134072
0.7864 Intermediate Similarity NPC256227
0.7864 Intermediate Similarity NPC202833
0.7857 Intermediate Similarity NPC238667
0.7857 Intermediate Similarity NPC73314
0.7857 Intermediate Similarity NPC9231
0.7857 Intermediate Similarity NPC117712
0.785 Intermediate Similarity NPC477127
0.785 Intermediate Similarity NPC258532
0.7845 Intermediate Similarity NPC470265
0.7845 Intermediate Similarity NPC23786
0.7843 Intermediate Similarity NPC57117
0.7835 Intermediate Similarity NPC470011
0.7835 Intermediate Similarity NPC97505
0.783 Intermediate Similarity NPC76866
0.783 Intermediate Similarity NPC88203
0.783 Intermediate Similarity NPC295791
0.783 Intermediate Similarity NPC304832
0.783 Intermediate Similarity NPC469606
0.783 Intermediate Similarity NPC286519
0.783 Intermediate Similarity NPC183571
0.783 Intermediate Similarity NPC58329
0.783 Intermediate Similarity NPC474709
0.783 Intermediate Similarity NPC214946
0.783 Intermediate Similarity NPC273005
0.783 Intermediate Similarity NPC148628
0.783 Intermediate Similarity NPC31058
0.783 Intermediate Similarity NPC275990
0.783 Intermediate Similarity NPC246736
0.7826 Intermediate Similarity NPC475003
0.7826 Intermediate Similarity NPC475885
0.7818 Intermediate Similarity NPC478209
0.7818 Intermediate Similarity NPC474567
0.7818 Intermediate Similarity NPC100908
0.781 Intermediate Similarity NPC476299
0.781 Intermediate Similarity NPC474012
0.781 Intermediate Similarity NPC474718
0.781 Intermediate Similarity NPC287676
0.781 Intermediate Similarity NPC470388
0.7807 Intermediate Similarity NPC478206
0.7807 Intermediate Similarity NPC146280
0.7807 Intermediate Similarity NPC478205
0.7807 Intermediate Similarity NPC124676
0.7807 Intermediate Similarity NPC108581
0.78 Intermediate Similarity NPC291875
0.78 Intermediate Similarity NPC206001
0.78 Intermediate Similarity NPC218927
0.7798 Intermediate Similarity NPC151393
0.7798 Intermediate Similarity NPC289702
0.7798 Intermediate Similarity NPC472218
0.7798 Intermediate Similarity NPC275539
0.7798 Intermediate Similarity NPC472219
0.7798 Intermediate Similarity NPC189075
0.7798 Intermediate Similarity NPC472217
0.7798 Intermediate Similarity NPC208461
0.7797 Intermediate Similarity NPC293112
0.7788 Intermediate Similarity NPC64318
0.7788 Intermediate Similarity NPC73911
0.7788 Intermediate Similarity NPC154363
0.7788 Intermediate Similarity NPC234858
0.7788 Intermediate Similarity NPC471127
0.7788 Intermediate Similarity NPC474333
0.7778 Intermediate Similarity NPC295366
0.7778 Intermediate Similarity NPC477125
0.7778 Intermediate Similarity NPC138908
0.7778 Intermediate Similarity NPC469789
0.7778 Intermediate Similarity NPC1679
0.7778 Intermediate Similarity NPC67251
0.7778 Intermediate Similarity NPC111952
0.7778 Intermediate Similarity NPC37600
0.7778 Intermediate Similarity NPC469607
0.7778 Intermediate Similarity NPC200957
0.7768 Intermediate Similarity NPC25909
0.7768 Intermediate Similarity NPC264153
0.7767 Intermediate Similarity NPC56369
0.7767 Intermediate Similarity NPC183012
0.7757 Intermediate Similarity NPC277074
0.7757 Intermediate Similarity NPC99266
0.7757 Intermediate Similarity NPC209298
0.7757 Intermediate Similarity NPC87927
0.7748 Intermediate Similarity NPC469656
0.7748 Intermediate Similarity NPC469655
0.7748 Intermediate Similarity NPC474846

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC156681 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
0.8058 Intermediate Similarity NPD4225 Approved
0.7798 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7565 Intermediate Similarity NPD7115 Discovery
0.7315 Intermediate Similarity NPD7639 Approved
0.7315 Intermediate Similarity NPD7640 Approved
0.7264 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7257 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD5344 Discontinued
0.7222 Intermediate Similarity NPD7638 Approved
0.7193 Intermediate Similarity NPD6371 Approved
0.7177 Intermediate Similarity NPD7319 Approved
0.7168 Intermediate Similarity NPD6686 Approved
0.7083 Intermediate Similarity NPD6319 Approved
0.7043 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7025 Intermediate Similarity NPD6921 Approved
0.6935 Remote Similarity NPD7507 Approved
0.693 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6916 Remote Similarity NPD5778 Approved
0.6916 Remote Similarity NPD5779 Approved
0.6893 Remote Similarity NPD1694 Approved
0.6887 Remote Similarity NPD6698 Approved
0.6887 Remote Similarity NPD46 Approved
0.6887 Remote Similarity NPD5785 Approved
0.6885 Remote Similarity NPD8516 Approved
0.6885 Remote Similarity NPD8513 Phase 3
0.6885 Remote Similarity NPD8515 Approved
0.6885 Remote Similarity NPD8517 Approved
0.6864 Remote Similarity NPD4632 Approved
0.6864 Remote Similarity NPD8133 Approved
0.6855 Remote Similarity NPD7492 Approved
0.6852 Remote Similarity NPD5282 Discontinued
0.6847 Remote Similarity NPD6648 Approved
0.6822 Remote Similarity NPD8034 Phase 2
0.6822 Remote Similarity NPD8035 Phase 2
0.6822 Remote Similarity NPD7637 Suspended
0.6822 Remote Similarity NPD7983 Approved
0.6803 Remote Similarity NPD6054 Approved
0.68 Remote Similarity NPD6616 Approved
0.6783 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6783 Remote Similarity NPD5697 Approved
0.6759 Remote Similarity NPD6399 Phase 3
0.6752 Remote Similarity NPD4634 Approved
0.6748 Remote Similarity NPD6015 Approved
0.6748 Remote Similarity NPD6016 Approved
0.6746 Remote Similarity NPD7078 Approved
0.6726 Remote Similarity NPD7632 Discontinued
0.6724 Remote Similarity NPD6881 Approved
0.6724 Remote Similarity NPD6899 Approved
0.6696 Remote Similarity NPD6008 Approved
0.6695 Remote Similarity NPD6649 Approved
0.6695 Remote Similarity NPD6650 Approved
0.6694 Remote Similarity NPD6370 Approved
0.6694 Remote Similarity NPD5988 Approved
0.6693 Remote Similarity NPD7736 Approved
0.6667 Remote Similarity NPD6012 Approved
0.6667 Remote Similarity NPD6013 Approved
0.6667 Remote Similarity NPD7902 Approved
0.6667 Remote Similarity NPD6411 Approved
0.6667 Remote Similarity NPD6014 Approved
0.664 Remote Similarity NPD8328 Phase 3
0.6639 Remote Similarity NPD8297 Approved
0.6614 Remote Similarity NPD8074 Phase 3
0.661 Remote Similarity NPD7102 Approved
0.661 Remote Similarity NPD7290 Approved
0.661 Remote Similarity NPD6883 Approved
0.6602 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6581 Remote Similarity NPD6011 Approved
0.6579 Remote Similarity NPD5211 Phase 2
0.6574 Remote Similarity NPD7838 Discovery
0.6571 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6557 Remote Similarity NPD6009 Approved
0.6557 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6555 Remote Similarity NPD8130 Phase 1
0.6555 Remote Similarity NPD6847 Approved
0.6555 Remote Similarity NPD6869 Approved
0.6555 Remote Similarity NPD6617 Approved
0.6555 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6552 Remote Similarity NPD5739 Approved
0.6552 Remote Similarity NPD6675 Approved
0.6552 Remote Similarity NPD6402 Approved
0.6552 Remote Similarity NPD7128 Approved
0.6545 Remote Similarity NPD7748 Approved
0.6532 Remote Similarity NPD6059 Approved
0.6525 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6525 Remote Similarity NPD6373 Approved
0.6525 Remote Similarity NPD6372 Approved
0.6514 Remote Similarity NPD7515 Phase 2
0.6509 Remote Similarity NPD3618 Phase 1
0.6504 Remote Similarity NPD7327 Approved
0.6504 Remote Similarity NPD7328 Approved
0.65 Remote Similarity NPD6882 Approved
0.6496 Remote Similarity NPD6412 Phase 2
0.6496 Remote Similarity NPD5701 Approved
0.6484 Remote Similarity NPD8293 Discontinued
0.6481 Remote Similarity NPD6101 Approved
0.6481 Remote Similarity NPD1695 Approved
0.6481 Remote Similarity NPD5764 Clinical (unspecified phase)
0.648 Remote Similarity NPD5983 Phase 2
0.6466 Remote Similarity NPD5141 Approved
0.6452 Remote Similarity NPD7516 Approved
0.6441 Remote Similarity NPD7320 Approved
0.6429 Remote Similarity NPD4697 Phase 3
0.6415 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6415 Remote Similarity NPD5363 Approved
0.6404 Remote Similarity NPD5286 Approved
0.6404 Remote Similarity NPD4696 Approved
0.6404 Remote Similarity NPD5285 Approved
0.6396 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6396 Remote Similarity NPD7900 Approved
0.6378 Remote Similarity NPD7604 Phase 2
0.6364 Remote Similarity NPD6053 Discontinued
0.6364 Remote Similarity NPD6079 Approved
0.6355 Remote Similarity NPD4249 Approved
0.6349 Remote Similarity NPD8033 Approved
0.6349 Remote Similarity NPD7503 Approved
0.6349 Remote Similarity NPD8378 Approved
0.6349 Remote Similarity NPD8380 Approved
0.6349 Remote Similarity NPD8296 Approved
0.6349 Remote Similarity NPD8335 Approved
0.6349 Remote Similarity NPD8379 Approved
0.6348 Remote Similarity NPD1700 Approved
0.6316 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6296 Remote Similarity NPD4251 Approved
0.6296 Remote Similarity NPD4250 Approved
0.6293 Remote Similarity NPD5224 Approved
0.6293 Remote Similarity NPD5225 Approved
0.6293 Remote Similarity NPD5226 Approved
0.6293 Remote Similarity NPD4633 Approved
0.6286 Remote Similarity NPD3667 Approved
0.6286 Remote Similarity NPD4269 Approved
0.6286 Remote Similarity NPD4270 Approved
0.6283 Remote Similarity NPD5221 Approved
0.6283 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6283 Remote Similarity NPD5222 Approved
0.6279 Remote Similarity NPD6336 Discontinued
0.627 Remote Similarity NPD8294 Approved
0.627 Remote Similarity NPD8377 Approved
0.6239 Remote Similarity NPD5175 Approved
0.6239 Remote Similarity NPD5174 Approved
0.6228 Remote Similarity NPD4755 Approved
0.6228 Remote Similarity NPD5173 Approved
0.6228 Remote Similarity NPD6083 Phase 2
0.6228 Remote Similarity NPD6084 Phase 2
0.6226 Remote Similarity NPD7154 Phase 3
0.622 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6214 Remote Similarity NPD6114 Approved
0.6214 Remote Similarity NPD6697 Approved
0.6214 Remote Similarity NPD6118 Approved
0.6214 Remote Similarity NPD6115 Approved
0.621 Remote Similarity NPD6274 Approved
0.6207 Remote Similarity NPD5223 Approved
0.6204 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6204 Remote Similarity NPD5786 Approved
0.6195 Remote Similarity NPD5695 Phase 3
0.619 Remote Similarity NPD7101 Approved
0.619 Remote Similarity NPD7100 Approved
0.619 Remote Similarity NPD5369 Approved
0.6182 Remote Similarity NPD5328 Approved
0.6174 Remote Similarity NPD5696 Approved
0.6168 Remote Similarity NPD4786 Approved
0.6168 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6165 Remote Similarity NPD7260 Phase 2
0.6161 Remote Similarity NPD4202 Approved
0.616 Remote Similarity NPD6317 Approved
0.6148 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6147 Remote Similarity NPD7524 Approved
0.6147 Remote Similarity NPD3573 Approved
0.614 Remote Similarity NPD7839 Suspended
0.6121 Remote Similarity NPD4700 Approved
0.6117 Remote Similarity NPD6116 Phase 1
0.6111 Remote Similarity NPD6335 Approved
0.6111 Remote Similarity NPD6314 Approved
0.6111 Remote Similarity NPD6313 Approved
0.6095 Remote Similarity NPD4252 Approved
0.6095 Remote Similarity NPD5790 Clinical (unspecified phase)
0.608 Remote Similarity NPD6868 Approved
0.6075 Remote Similarity NPD6695 Phase 3
0.6075 Remote Similarity NPD5362 Discontinued
0.6071 Remote Similarity NPD5284 Approved
0.6071 Remote Similarity NPD5281 Approved
0.6061 Remote Similarity NPD6033 Approved
0.6058 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6055 Remote Similarity NPD7146 Approved
0.6055 Remote Similarity NPD7334 Approved
0.6055 Remote Similarity NPD6409 Approved
0.6055 Remote Similarity NPD5330 Approved
0.6055 Remote Similarity NPD6684 Approved
0.6055 Remote Similarity NPD7521 Approved
0.6053 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6053 Remote Similarity NPD5210 Approved
0.6053 Remote Similarity NPD4629 Approved
0.6033 Remote Similarity NPD4729 Approved
0.6033 Remote Similarity NPD4730 Approved
0.6019 Remote Similarity NPD6117 Approved
0.6019 Remote Similarity NPD3666 Approved
0.6019 Remote Similarity NPD3133 Approved
0.6019 Remote Similarity NPD3665 Phase 1
0.6 Remote Similarity NPD6067 Discontinued
0.6 Remote Similarity NPD7642 Approved
0.5981 Remote Similarity NPD6435 Approved

Structure

External Identifiers

PubChem CID   13006379
ChEMBL   CHEMBL465547
ZINC  

Physicochemical Properties

Molecular Weight:  376.15
ALogP:  0.706
MLogP:  2.89
XLogP:  0.728
# Rotatable Bonds:  11
Polar Surface Area:  110.13
# H-Bond Aceptor:  7
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  27

Download Data

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