Natural Product: NPC287089

Natural Product ID:  NPC287089
Common Name:   Eupacunoxin
IUPAC Name:   [(3aS,4R,5Z,7S,9S,10Z,11aR)-9-acetyloxy-7-hydroxy-6,10-dimethyl-3-methylidene-2-oxo-3a,4,7,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] (2R,3R)-2,3-dimethyloxirane-2-carboxylate
Synonyms:   Eupacunoxin
Molecular Formula:   C22H28O8
Standard InCHIKey:  QGXSKKOWDFZPIV-CXDYXSGLSA-N
Standard InCHI:  InChI=1S/C22H28O8/c1-10-7-18(29-21(26)22(6)13(4)30-22)19-12(3)20(25)28-17(19)8-11(2)16(9-15(10)24)27-14(5)23/h7-8,13,15-19,24H,3,9H2,1-2,4-6H3/b10-7-,11-8-/t13-,15+,16+,17-,18-,19+,22-/m1/s1
Canonical SMILES:  CC(=O)O[C@H]1C[C@H](O)/C(=C[C@H]([C@@H]2[C@@H](/C=C1/C)OC(=O)C2=C)OC(=O)[C@]1(C)O[C@@H]1C)/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
NPO33469 Asteraceae Family Asteraceae Eukaryota PMID[18329753]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT91 Cell Line KB Homo sapiens ED50 = 2.1 ug/ml 20795741
NPT91 Cell Line KB Homo sapiens ED50 = 5 umol/ml 11325240

  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 NPC287089 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
0.8736 High Similarity NPC266957
0.871 High Similarity NPC475949
0.8537 High Similarity NPC68819
0.8444 Intermediate Similarity NPC474232
0.8409 Intermediate Similarity NPC469910
0.8391 Intermediate Similarity NPC158756
0.8333 Intermediate Similarity NPC471148
0.8295 Intermediate Similarity NPC470755
0.8276 Intermediate Similarity NPC116543
0.8261 Intermediate Similarity NPC165383
0.8229 Intermediate Similarity NPC474339
0.8229 Intermediate Similarity NPC164598
0.8222 Intermediate Similarity NPC476805
0.8222 Intermediate Similarity NPC475819
0.8222 Intermediate Similarity NPC476803
0.8211 Intermediate Similarity NPC471144
0.8191 Intermediate Similarity NPC17585
0.8191 Intermediate Similarity NPC279621
0.8191 Intermediate Similarity NPC473859
0.8191 Intermediate Similarity NPC230800
0.8182 Intermediate Similarity NPC477513
0.8125 Intermediate Similarity NPC288876
0.8105 Intermediate Similarity NPC471140
0.8085 Intermediate Similarity NPC475659
0.8085 Intermediate Similarity NPC471142
0.8068 Intermediate Similarity NPC131669
0.8068 Intermediate Similarity NPC169575
0.8068 Intermediate Similarity NPC40746
0.8068 Intermediate Similarity NPC473390
0.8046 Intermediate Similarity NPC24417
0.7979 Intermediate Similarity NPC57405
0.7979 Intermediate Similarity NPC121825
0.7979 Intermediate Similarity NPC474247
0.7979 Intermediate Similarity NPC303942
0.7978 Intermediate Similarity NPC476804
0.7955 Intermediate Similarity NPC229825
0.7955 Intermediate Similarity NPC11383
0.7955 Intermediate Similarity NPC474959
0.7955 Intermediate Similarity NPC310450
0.7955 Intermediate Similarity NPC475046
0.7938 Intermediate Similarity NPC477512
0.7921 Intermediate Similarity NPC14862
0.7921 Intermediate Similarity NPC233379
0.7921 Intermediate Similarity NPC474664
0.7907 Intermediate Similarity NPC318481
0.79 Intermediate Similarity NPC475802
0.7895 Intermediate Similarity NPC477922
0.7889 Intermediate Similarity NPC255307
0.7872 Intermediate Similarity NPC475838
0.7872 Intermediate Similarity NPC469692
0.7872 Intermediate Similarity NPC228451
0.7872 Intermediate Similarity NPC469645
0.7872 Intermediate Similarity NPC475302
0.7872 Intermediate Similarity NPC125674
0.7865 Intermediate Similarity NPC229799
0.7865 Intermediate Similarity NPC286770
0.7865 Intermediate Similarity NPC284472
0.7857 Intermediate Similarity NPC476590
0.7857 Intermediate Similarity NPC110443
0.7857 Intermediate Similarity NPC185141
0.7857 Intermediate Similarity NPC114727
0.7857 Intermediate Similarity NPC477511
0.7857 Intermediate Similarity NPC264477
0.7857 Intermediate Similarity NPC201718
0.7857 Intermediate Similarity NPC133907
0.7857 Intermediate Similarity NPC46998
0.7857 Intermediate Similarity NPC128733
0.7843 Intermediate Similarity NPC15218
0.7822 Intermediate Similarity NPC474421
0.7822 Intermediate Similarity NPC72813
0.7822 Intermediate Similarity NPC194620
0.7822 Intermediate Similarity NPC326994
0.7822 Intermediate Similarity NPC324327
0.7816 Intermediate Similarity NPC167881
0.7816 Intermediate Similarity NPC98557
0.7812 Intermediate Similarity NPC476315
0.7812 Intermediate Similarity NPC477921
0.7802 Intermediate Similarity NPC475461
0.7802 Intermediate Similarity NPC305475
0.7778 Intermediate Similarity NPC191476
0.7778 Intermediate Similarity NPC114979
0.7778 Intermediate Similarity NPC149371
0.7778 Intermediate Similarity NPC96259
0.7778 Intermediate Similarity NPC141193
0.7767 Intermediate Similarity NPC115257
0.7767 Intermediate Similarity NPC161816
0.7766 Intermediate Similarity NPC158061
0.7766 Intermediate Similarity NPC473321
0.7765 Intermediate Similarity NPC473582
0.7745 Intermediate Similarity NPC55972
0.7745 Intermediate Similarity NPC327286
0.7745 Intermediate Similarity NPC169888
0.7723 Intermediate Similarity NPC16313
0.7723 Intermediate Similarity NPC9303
0.7708 Intermediate Similarity NPC14961
0.7708 Intermediate Similarity NPC270013
0.7701 Intermediate Similarity NPC471465
0.7701 Intermediate Similarity NPC196653
0.77 Intermediate Similarity NPC472755
0.7684 Intermediate Similarity NPC288240
0.7684 Intermediate Similarity NPC162205
0.7684 Intermediate Similarity NPC295204
0.7684 Intermediate Similarity NPC273579
0.7677 Intermediate Similarity NPC47880
0.7674 Intermediate Similarity NPC301207
0.767 Intermediate Similarity NPC475922
0.7667 Intermediate Similarity NPC59097
0.766 Intermediate Similarity NPC469368
0.766 Intermediate Similarity NPC473619
0.766 Intermediate Similarity NPC475855
0.7647 Intermediate Similarity NPC326504
0.7647 Intermediate Similarity NPC473489
0.764 Intermediate Similarity NPC150502
0.764 Intermediate Similarity NPC52861
0.7634 Intermediate Similarity NPC473715
0.7624 Intermediate Similarity NPC471143
0.7624 Intermediate Similarity NPC477510
0.7624 Intermediate Similarity NPC475676
0.7624 Intermediate Similarity NPC220964
0.7614 Intermediate Similarity NPC99651
0.7609 Intermediate Similarity NPC469483
0.7604 Intermediate Similarity NPC471147
0.7604 Intermediate Similarity NPC474035
0.7604 Intermediate Similarity NPC81386
0.7586 Intermediate Similarity NPC7563
0.7586 Intermediate Similarity NPC474818
0.7586 Intermediate Similarity NPC51809
0.7586 Intermediate Similarity NPC476028
0.7586 Intermediate Similarity NPC176329
0.7586 Intermediate Similarity NPC171204
0.7586 Intermediate Similarity NPC49302
0.7586 Intermediate Similarity NPC320630
0.7586 Intermediate Similarity NPC141789
0.7586 Intermediate Similarity NPC125365
0.7586 Intermediate Similarity NPC116177
0.7561 Intermediate Similarity NPC194871
0.7553 Intermediate Similarity NPC474032
0.7526 Intermediate Similarity NPC36954
0.7526 Intermediate Similarity NPC471141
0.7525 Intermediate Similarity NPC4620
0.75 Intermediate Similarity NPC21469
0.75 Intermediate Similarity NPC279214
0.75 Intermediate Similarity NPC221095
0.75 Intermediate Similarity NPC93763
0.75 Intermediate Similarity NPC212486
0.75 Intermediate Similarity NPC108816
0.75 Intermediate Similarity NPC473471
0.75 Intermediate Similarity NPC267231
0.75 Intermediate Similarity NPC475912
0.75 Intermediate Similarity NPC476270
0.7475 Intermediate Similarity NPC473326
0.7474 Intermediate Similarity NPC144133
0.7474 Intermediate Similarity NPC179394
0.7471 Intermediate Similarity NPC209113
0.7471 Intermediate Similarity NPC256640
0.7471 Intermediate Similarity NPC16279
0.7471 Intermediate Similarity NPC127118
0.7471 Intermediate Similarity NPC205615
0.7453 Intermediate Similarity NPC473877
0.7451 Intermediate Similarity NPC474741
0.7451 Intermediate Similarity NPC472756
0.7449 Intermediate Similarity NPC306041
0.7447 Intermediate Similarity NPC475902
0.7447 Intermediate Similarity NPC260343
0.7444 Intermediate Similarity NPC141810
0.7426 Intermediate Similarity NPC472754
0.7423 Intermediate Similarity NPC469632
0.7419 Intermediate Similarity NPC150755
0.7419 Intermediate Similarity NPC50637
0.7416 Intermediate Similarity NPC475210
0.7416 Intermediate Similarity NPC270126
0.7396 Intermediate Similarity NPC20713
0.7386 Intermediate Similarity NPC474278
0.7386 Intermediate Similarity NPC97516
0.7381 Intermediate Similarity NPC476591
0.7381 Intermediate Similarity NPC88877
0.7368 Intermediate Similarity NPC151770
0.7363 Intermediate Similarity NPC474252
0.7356 Intermediate Similarity NPC161038
0.7353 Intermediate Similarity NPC475945
0.7353 Intermediate Similarity NPC474166
0.7353 Intermediate Similarity NPC19239
0.7353 Intermediate Similarity NPC475871
0.734 Intermediate Similarity NPC72513
0.734 Intermediate Similarity NPC471738
0.7333 Intermediate Similarity NPC281132
0.7327 Intermediate Similarity NPC472753
0.7327 Intermediate Similarity NPC473332
0.732 Intermediate Similarity NPC476300
0.7312 Intermediate Similarity NPC261380
0.7312 Intermediate Similarity NPC165162
0.7308 Intermediate Similarity NPC266514
0.73 Intermediate Similarity NPC474213
0.73 Intermediate Similarity NPC161855
0.7292 Intermediate Similarity NPC475748
0.7283 Intermediate Similarity NPC474703
0.7283 Intermediate Similarity NPC44261
0.7273 Intermediate Similarity NPC76862
0.7273 Intermediate Similarity NPC39859
0.7273 Intermediate Similarity NPC158416

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC287089 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
0.7143 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7128 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD6698 Approved
0.7113 Intermediate Similarity NPD46 Approved
0.6961 Remote Similarity NPD4225 Approved
0.6939 Remote Similarity NPD7838 Discovery
0.6789 Remote Similarity NPD6371 Approved
0.67 Remote Similarity NPD7983 Approved
0.6667 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6635 Remote Similarity NPD8029 Clinical (unspecified phase)
0.66 Remote Similarity NPD5785 Approved
0.6596 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6577 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6458 Remote Similarity NPD5209 Approved
0.6435 Remote Similarity NPD7115 Discovery
0.6429 Remote Similarity NPD5363 Approved
0.6421 Remote Similarity NPD4822 Approved
0.6421 Remote Similarity NPD4820 Approved
0.6421 Remote Similarity NPD4821 Approved
0.6421 Remote Similarity NPD4252 Approved
0.6421 Remote Similarity NPD4819 Approved
0.6392 Remote Similarity NPD7154 Phase 3
0.6383 Remote Similarity NPD4271 Approved
0.6383 Remote Similarity NPD4268 Approved
0.6364 Remote Similarity NPD4249 Approved
0.6355 Remote Similarity NPD5344 Discontinued
0.6337 Remote Similarity NPD1695 Approved
0.6322 Remote Similarity NPD2685 Clinical (unspecified phase)
0.63 Remote Similarity NPD4251 Approved
0.63 Remote Similarity NPD4250 Approved
0.6289 Remote Similarity NPD4269 Approved
0.6289 Remote Similarity NPD4270 Approved
0.6283 Remote Similarity NPD2204 Approved
0.6263 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6224 Remote Similarity NPD6110 Phase 1
0.62 Remote Similarity NPD5786 Approved
0.6186 Remote Similarity NPD5369 Approved
0.6162 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6111 Remote Similarity NPD6648 Approved
0.6105 Remote Similarity NPD4756 Discovery
0.6095 Remote Similarity NPD5282 Discontinued
0.6083 Remote Similarity NPD8516 Approved
0.6083 Remote Similarity NPD8513 Phase 3
0.6083 Remote Similarity NPD8515 Approved
0.6083 Remote Similarity NPD8517 Approved
0.6061 Remote Similarity NPD5362 Discontinued
0.6058 Remote Similarity NPD7637 Suspended
0.6019 Remote Similarity NPD5370 Suspended
0.6018 Remote Similarity NPD6686 Approved
0.6 Remote Similarity NPD7601 Clinical (unspecified phase)
0.6 Remote Similarity NPD5778 Approved
0.6 Remote Similarity NPD6109 Phase 1
0.6 Remote Similarity NPD5779 Approved
0.5981 Remote Similarity NPD4792 Clinical (unspecified phase)
0.5981 Remote Similarity NPD7839 Suspended
0.5905 Remote Similarity NPD4810 Clinical (unspecified phase)
0.59 Remote Similarity NPD5332 Approved
0.59 Remote Similarity NPD5331 Approved
0.5876 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5862 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5859 Remote Similarity NPD4790 Discontinued
0.5854 Remote Similarity NPD7642 Approved
0.584 Remote Similarity NPD8074 Phase 3
0.5814 Remote Similarity NPD69 Approved
0.5814 Remote Similarity NPD9119 Approved
0.5814 Remote Similarity NPD585 Clinical (unspecified phase)
0.5812 Remote Similarity NPD8297 Approved
0.5802 Remote Similarity NPD7966 Clinical (unspecified phase)
0.58 Remote Similarity NPD6435 Approved
0.5776 Remote Similarity NPD5955 Clinical (unspecified phase)
0.576 Remote Similarity NPD8273 Phase 1
0.5738 Remote Similarity NPD6319 Approved
0.5726 Remote Similarity NPD7829 Approved
0.5726 Remote Similarity NPD6649 Approved
0.5726 Remote Similarity NPD7830 Approved
0.5726 Remote Similarity NPD6650 Approved
0.5714 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6101 Approved
0.5698 Remote Similarity NPD9118 Approved
0.569 Remote Similarity NPD6372 Approved
0.569 Remote Similarity NPD4061 Clinical (unspecified phase)
0.569 Remote Similarity NPD6373 Approved
0.5676 Remote Similarity NPD7639 Approved
0.5676 Remote Similarity NPD7640 Approved
0.567 Remote Similarity NPD819 Approved
0.567 Remote Similarity NPD818 Approved
0.5667 Remote Similarity NPD3197 Phase 1
0.5652 Remote Similarity NPD4247 Clinical (unspecified phase)
0.5652 Remote Similarity NPD5697 Approved
0.5644 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5636 Remote Similarity NPD6083 Phase 2
0.5636 Remote Similarity NPD6084 Phase 2
0.5631 Remote Similarity NPD1694 Approved
0.5607 Remote Similarity NPD6411 Approved
0.5603 Remote Similarity NPD6881 Approved
0.5603 Remote Similarity NPD6899 Approved
0.56 Remote Similarity NPD5368 Approved

Structure

External Identifiers

PubChem CID   5281451
ChEMBL   CHEMBL484877
ZINC  

Physicochemical Properties

Molecular Weight:  420.18
ALogP:  0.8223
MLogP:  3
XLogP:  0.964
# Rotatable Bonds:  11
Polar Surface Area:  111.66
# H-Bond Aceptor:  8
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  30

Download Data

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Similar NPs/Drugs