Natural Product: NPC189338

Natural Product ID:  NPC189338
Common Name:   Eupachlorin Acetate
IUPAC Name:   [(3aR,4R,6R,6aR,7R,9aS,9bS)-7-acetyloxy-6-(chloromethyl)-6,9a-dihydroxy-9-methyl-3-methylidene-2-oxo-3a,4,5,6a,7,9b-hexahydroazuleno[4,5-b]furan-4-yl] (Z)-2-methylbut-2-enoate
Synonyms:   Eupachlorin Acetate
Molecular Formula:   C22H27ClO8
Standard InCHIKey:  WVTMFOWXYVFVDE-UPVVJIFBSA-N
Standard InCHI:  InChI=1S/C22H27ClO8/c1-6-10(2)19(25)30-15-8-21(27,9-23)17-14(29-13(5)24)7-11(3)22(17,28)18-16(15)12(4)20(26)31-18/h6-7,14-18,27-28H,4,8-9H2,1-3,5H3/b10-6-/t14-,15-,16-,17+,18+,21+,22-/m1/s1
Canonical SMILES:  C/C=C(C(=O)O[C@@H]1C[C@](O)(CCl)[C@H]2[C@]([C@@H]3[C@@H]1C(=C)C(=O)O3)(O)C(=C[C@H]2OC(=O)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
NPO26385 Eupatorium rotundifolium Species Asteraceae Eukaryota TCM_Taiwan*
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 = 0.16 ug/ml 17336532
NPT91 Cell Line KB Homo sapiens ED50 = 0.35 umol/ml 18329753

  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 NPC189338 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
1.0 High Similarity NPC95290
0.9808 High Similarity NPC258711
0.9808 High Similarity NPC35069
0.9231 High Similarity NPC166115
0.9048 High Similarity NPC223450
0.9 High Similarity NPC255450
0.9 High Similarity NPC170692
0.8909 High Similarity NPC121816
0.8868 High Similarity NPC243998
0.8818 High Similarity NPC273242
0.8585 High Similarity NPC86077
0.8447 Intermediate Similarity NPC477131
0.8426 Intermediate Similarity NPC100487
0.8364 Intermediate Similarity NPC68248
0.8273 Intermediate Similarity NPC26617
0.8269 Intermediate Similarity NPC470010
0.8269 Intermediate Similarity NPC470013
0.8269 Intermediate Similarity NPC198853
0.8269 Intermediate Similarity NPC262133
0.8269 Intermediate Similarity NPC323008
0.8252 Intermediate Similarity NPC133698
0.819 Intermediate Similarity NPC304886
0.819 Intermediate Similarity NPC36954
0.8182 Intermediate Similarity NPC54737
0.8173 Intermediate Similarity NPC475912
0.8173 Intermediate Similarity NPC135776
0.8173 Intermediate Similarity NPC476300
0.8148 Intermediate Similarity NPC150923
0.8125 Intermediate Similarity NPC115352
0.8125 Intermediate Similarity NPC139838
0.8125 Intermediate Similarity NPC59489
0.8091 Intermediate Similarity NPC203659
0.8077 Intermediate Similarity NPC131209
0.8019 Intermediate Similarity NPC270013
0.8019 Intermediate Similarity NPC67584
0.8019 Intermediate Similarity NPC14961
0.8 Intermediate Similarity NPC475945
0.8 Intermediate Similarity NPC179746
0.8 Intermediate Similarity NPC81419
0.8 Intermediate Similarity NPC124881
0.8 Intermediate Similarity NPC475871
0.8 Intermediate Similarity NPC110989
0.7982 Intermediate Similarity NPC474742
0.7981 Intermediate Similarity NPC51004
0.7944 Intermediate Similarity NPC476315
0.7944 Intermediate Similarity NPC213078
0.7928 Intermediate Similarity NPC474741
0.7925 Intermediate Similarity NPC81386
0.7925 Intermediate Similarity NPC474035
0.7909 Intermediate Similarity NPC474747
0.7909 Intermediate Similarity NPC225353
0.7905 Intermediate Similarity NPC208886
0.7905 Intermediate Similarity NPC12172
0.7905 Intermediate Similarity NPC30515
0.7905 Intermediate Similarity NPC184463
0.7895 Intermediate Similarity NPC477103
0.789 Intermediate Similarity NPC186861
0.7885 Intermediate Similarity NPC32922
0.7885 Intermediate Similarity NPC307411
0.787 Intermediate Similarity NPC161493
0.787 Intermediate Similarity NPC471150
0.7869 Intermediate Similarity NPC470973
0.785 Intermediate Similarity NPC52044
0.783 Intermediate Similarity NPC212486
0.781 Intermediate Similarity NPC474761
0.781 Intermediate Similarity NPC476004
0.7807 Intermediate Similarity NPC477102
0.7798 Intermediate Similarity NPC473326
0.7798 Intermediate Similarity NPC221615
0.7798 Intermediate Similarity NPC187268
0.7788 Intermediate Similarity NPC202672
0.7788 Intermediate Similarity NPC91248
0.7778 Intermediate Similarity NPC279621
0.7757 Intermediate Similarity NPC127019
0.7748 Intermediate Similarity NPC149371
0.7739 Intermediate Similarity NPC257240
0.7736 Intermediate Similarity NPC475925
0.7736 Intermediate Similarity NPC473321
0.7727 Intermediate Similarity NPC471381
0.7727 Intermediate Similarity NPC288876
0.7727 Intermediate Similarity NPC70865
0.7714 Intermediate Similarity NPC295312
0.7712 Intermediate Similarity NPC329869
0.7706 Intermediate Similarity NPC170143
0.7706 Intermediate Similarity NPC245521
0.7706 Intermediate Similarity NPC213947
0.7706 Intermediate Similarity NPC108475
0.7706 Intermediate Similarity NPC181151
0.7692 Intermediate Similarity NPC190753
0.7685 Intermediate Similarity NPC220221
0.7685 Intermediate Similarity NPC163228
0.7685 Intermediate Similarity NPC471142
0.7685 Intermediate Similarity NPC476053
0.7685 Intermediate Similarity NPC472873
0.7685 Intermediate Similarity NPC170120
0.7685 Intermediate Similarity NPC213698
0.7679 Intermediate Similarity NPC475873
0.7672 Intermediate Similarity NPC287311
0.7664 Intermediate Similarity NPC273579
0.7664 Intermediate Similarity NPC295204
0.7664 Intermediate Similarity NPC288240
0.7664 Intermediate Similarity NPC162205
0.7658 Intermediate Similarity NPC47880
0.7658 Intermediate Similarity NPC171759
0.7652 Intermediate Similarity NPC273433
0.7647 Intermediate Similarity NPC471145
0.7647 Intermediate Similarity NPC471146
0.7642 Intermediate Similarity NPC473619
0.7642 Intermediate Similarity NPC475748
0.7642 Intermediate Similarity NPC37607
0.7642 Intermediate Similarity NPC129419
0.7642 Intermediate Similarity NPC301969
0.7636 Intermediate Similarity NPC471144
0.7636 Intermediate Similarity NPC474213
0.7636 Intermediate Similarity NPC141191
0.7627 Intermediate Similarity NPC471380
0.7619 Intermediate Similarity NPC178875
0.7619 Intermediate Similarity NPC79549
0.7619 Intermediate Similarity NPC153805
0.7615 Intermediate Similarity NPC24956
0.7615 Intermediate Similarity NPC18019
0.7615 Intermediate Similarity NPC476009
0.7593 Intermediate Similarity NPC473316
0.7593 Intermediate Similarity NPC474338
0.7593 Intermediate Similarity NPC474247
0.7593 Intermediate Similarity NPC303942
0.7593 Intermediate Similarity NPC473330
0.7593 Intermediate Similarity NPC57405
0.7586 Intermediate Similarity NPC471884
0.757 Intermediate Similarity NPC261607
0.757 Intermediate Similarity NPC111114
0.757 Intermediate Similarity NPC300312
0.7568 Intermediate Similarity NPC280963
0.7565 Intermediate Similarity NPC117604
0.7547 Intermediate Similarity NPC268298
0.7547 Intermediate Similarity NPC92974
0.7547 Intermediate Similarity NPC474032
0.7547 Intermediate Similarity NPC215556
0.7547 Intermediate Similarity NPC4986
0.7545 Intermediate Similarity NPC169205
0.7545 Intermediate Similarity NPC474313
0.7545 Intermediate Similarity NPC40812
0.7542 Intermediate Similarity NPC106395
0.7542 Intermediate Similarity NPC46269
0.7542 Intermediate Similarity NPC209058
0.7524 Intermediate Similarity NPC186148
0.7524 Intermediate Similarity NPC160138
0.7524 Intermediate Similarity NPC118601
0.7524 Intermediate Similarity NPC231889
0.7523 Intermediate Similarity NPC475900
0.7523 Intermediate Similarity NPC224689
0.7523 Intermediate Similarity NPC475659
0.7523 Intermediate Similarity NPC471141
0.7522 Intermediate Similarity NPC472755
0.75 Intermediate Similarity NPC15993
0.75 Intermediate Similarity NPC21469
0.75 Intermediate Similarity NPC110443
0.75 Intermediate Similarity NPC128733
0.75 Intermediate Similarity NPC228451
0.75 Intermediate Similarity NPC185141
0.75 Intermediate Similarity NPC133907
0.75 Intermediate Similarity NPC475323
0.75 Intermediate Similarity NPC475838
0.75 Intermediate Similarity NPC258216
0.75 Intermediate Similarity NPC476270
0.75 Intermediate Similarity NPC125674
0.75 Intermediate Similarity NPC46998
0.75 Intermediate Similarity NPC36754
0.7479 Intermediate Similarity NPC67290
0.7479 Intermediate Similarity NPC133677
0.7479 Intermediate Similarity NPC138303
0.7478 Intermediate Similarity NPC477513
0.7477 Intermediate Similarity NPC473448
0.7477 Intermediate Similarity NPC71533
0.7477 Intermediate Similarity NPC106510
0.7477 Intermediate Similarity NPC144133
0.7477 Intermediate Similarity NPC45125
0.7477 Intermediate Similarity NPC179394
0.7477 Intermediate Similarity NPC62815
0.7477 Intermediate Similarity NPC216284
0.7477 Intermediate Similarity NPC475855
0.7459 Intermediate Similarity NPC143755
0.7458 Intermediate Similarity NPC123855
0.7458 Intermediate Similarity NPC76550
0.7458 Intermediate Similarity NPC138757
0.7455 Intermediate Similarity NPC230800
0.7455 Intermediate Similarity NPC185553
0.7455 Intermediate Similarity NPC477921
0.7455 Intermediate Similarity NPC473859
0.7453 Intermediate Similarity NPC207114
0.7453 Intermediate Similarity NPC177629
0.7453 Intermediate Similarity NPC474471
0.7453 Intermediate Similarity NPC217983
0.7453 Intermediate Similarity NPC227379
0.7453 Intermediate Similarity NPC58219
0.7453 Intermediate Similarity NPC473715
0.7438 Intermediate Similarity NPC161060
0.7436 Intermediate Similarity NPC5103
0.7434 Intermediate Similarity NPC324017
0.7434 Intermediate Similarity NPC320019

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC189338 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
0.8273 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7739 Intermediate Similarity NPD6371 Approved
0.7547 Intermediate Similarity NPD1695 Approved
0.7364 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD46 Approved
0.7156 Intermediate Similarity NPD6698 Approved
0.7025 Intermediate Similarity NPD6053 Discontinued
0.7009 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.6937 Remote Similarity NPD7983 Approved
0.6847 Remote Similarity NPD7838 Discovery
0.6719 Remote Similarity NPD5983 Phase 2
0.6694 Remote Similarity NPD4632 Approved
0.6694 Remote Similarity NPD6686 Approved
0.6667 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5362 Discontinued
0.6641 Remote Similarity NPD7507 Approved
0.6636 Remote Similarity NPD4249 Approved
0.6581 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6581 Remote Similarity NPD4225 Approved
0.6577 Remote Similarity NPD4250 Approved
0.6577 Remote Similarity NPD4251 Approved
0.6549 Remote Similarity NPD5785 Approved
0.6522 Remote Similarity NPD5282 Discontinued
0.6515 Remote Similarity NPD6336 Discontinued
0.6493 Remote Similarity NPD7319 Approved
0.6471 Remote Similarity NPD5344 Discontinued
0.6462 Remote Similarity NPD8513 Phase 3
0.6462 Remote Similarity NPD8517 Approved
0.6462 Remote Similarity NPD8516 Approved
0.6462 Remote Similarity NPD8515 Approved
0.6434 Remote Similarity NPD7100 Approved
0.6418 Remote Similarity NPD6033 Approved
0.641 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6406 Remote Similarity NPD6009 Approved
0.6406 Remote Similarity NPD7115 Discovery
0.6396 Remote Similarity NPD5363 Approved
0.6396 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6393 Remote Similarity NPD6008 Approved
0.6385 Remote Similarity NPD6319 Approved
0.6364 Remote Similarity NPD7154 Phase 3
0.6357 Remote Similarity NPD6313 Approved
0.6357 Remote Similarity NPD6314 Approved
0.6357 Remote Similarity NPD6335 Approved
0.6339 Remote Similarity NPD5786 Approved
0.6324 Remote Similarity NPD5956 Approved
0.6308 Remote Similarity NPD7101 Approved
0.6293 Remote Similarity NPD5779 Approved
0.6293 Remote Similarity NPD5778 Approved
0.6273 Remote Similarity NPD6435 Approved
0.625 Remote Similarity NPD6648 Approved
0.6239 Remote Similarity NPD4821 Approved
0.6239 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6239 Remote Similarity NPD4819 Approved
0.6239 Remote Similarity NPD4822 Approved
0.6239 Remote Similarity NPD4820 Approved
0.6222 Remote Similarity NPD8074 Phase 3
0.622 Remote Similarity NPD8297 Approved
0.6194 Remote Similarity NPD7492 Approved
0.619 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6148 Remote Similarity NPD6616 Approved
0.6142 Remote Similarity NPD5215 Approved
0.6142 Remote Similarity NPD6650 Approved
0.6142 Remote Similarity NPD6649 Approved
0.6136 Remote Similarity NPD6054 Approved
0.6126 Remote Similarity NPD4270 Approved
0.6126 Remote Similarity NPD4269 Approved
0.6116 Remote Similarity NPD7640 Approved
0.6116 Remote Similarity NPD7639 Approved
0.6111 Remote Similarity NPD6372 Approved
0.6111 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6111 Remote Similarity NPD6373 Approved
0.6107 Remote Similarity NPD7327 Approved
0.6107 Remote Similarity NPD7328 Approved
0.6103 Remote Similarity NPD7078 Approved
0.6091 Remote Similarity NPD5368 Approved
0.609 Remote Similarity NPD8033 Approved
0.609 Remote Similarity NPD6016 Approved
0.609 Remote Similarity NPD6015 Approved
0.608 Remote Similarity NPD5697 Approved
0.6071 Remote Similarity NPD5331 Approved
0.6071 Remote Similarity NPD5332 Approved
0.6063 Remote Similarity NPD5169 Approved
0.6061 Remote Similarity NPD7516 Approved
0.6061 Remote Similarity NPD4522 Approved
0.6058 Remote Similarity NPD7736 Approved
0.6056 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6055 Remote Similarity NPD4268 Approved
0.6055 Remote Similarity NPD4271 Approved
0.6045 Remote Similarity NPD6370 Approved
0.6045 Remote Similarity NPD5988 Approved
0.6043 Remote Similarity NPD7260 Phase 2
0.6036 Remote Similarity NPD5369 Approved
0.6036 Remote Similarity NPD4790 Discontinued
0.6033 Remote Similarity NPD7638 Approved
0.6032 Remote Similarity NPD6881 Approved
0.6032 Remote Similarity NPD7320 Approved
0.6032 Remote Similarity NPD6899 Approved
0.6016 Remote Similarity NPD5216 Approved
0.6016 Remote Similarity NPD5127 Approved
0.6016 Remote Similarity NPD5217 Approved
0.6015 Remote Similarity NPD8294 Approved
0.6015 Remote Similarity NPD8377 Approved
0.6015 Remote Similarity NPD6059 Approved
0.6 Remote Similarity NPD5167 Approved
0.6 Remote Similarity NPD6675 Approved
0.6 Remote Similarity NPD7642 Approved
0.6 Remote Similarity NPD5739 Approved
0.6 Remote Similarity NPD7128 Approved
0.6 Remote Similarity NPD6845 Suspended
0.6 Remote Similarity NPD6402 Approved
0.6 Remote Similarity NPD7839 Suspended
0.5985 Remote Similarity NPD8293 Discontinued
0.5984 Remote Similarity NPD6014 Approved
0.5984 Remote Similarity NPD6012 Approved
0.5984 Remote Similarity NPD6013 Approved
0.5982 Remote Similarity NPD4752 Clinical (unspecified phase)
0.597 Remote Similarity NPD8335 Approved
0.597 Remote Similarity NPD8378 Approved
0.597 Remote Similarity NPD8379 Approved
0.597 Remote Similarity NPD8380 Approved
0.597 Remote Similarity NPD8296 Approved
0.597 Remote Similarity NPD7503 Approved
0.5969 Remote Similarity NPD6882 Approved
0.5965 Remote Similarity NPD1694 Approved
0.5954 Remote Similarity NPD6868 Approved
0.5952 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5952 Remote Similarity NPD5701 Approved
0.5952 Remote Similarity NPD6412 Phase 2
0.5946 Remote Similarity NPD4252 Approved
0.5938 Remote Similarity NPD7290 Approved
0.5938 Remote Similarity NPD7102 Approved
0.5938 Remote Similarity NPD6883 Approved
0.5917 Remote Similarity NPD5695 Phase 3
0.5912 Remote Similarity NPD8273 Phase 1
0.5909 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5906 Remote Similarity NPD6011 Approved
0.5906 Remote Similarity NPD5128 Approved
0.5902 Remote Similarity NPD5696 Approved
0.5891 Remote Similarity NPD8130 Phase 1
0.5891 Remote Similarity NPD6847 Approved
0.5891 Remote Similarity NPD6869 Approved
0.5891 Remote Similarity NPD6617 Approved
0.5887 Remote Similarity NPD5211 Phase 2
0.5882 Remote Similarity NPD7829 Approved
0.5882 Remote Similarity NPD6399 Phase 3
0.5882 Remote Similarity NPD7604 Phase 2
0.5882 Remote Similarity NPD7830 Approved
0.5865 Remote Similarity NPD7641 Discontinued
0.5841 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5841 Remote Similarity NPD5209 Approved
0.5827 Remote Similarity NPD6614 Approved
0.582 Remote Similarity NPD6083 Phase 2
0.582 Remote Similarity NPD6084 Phase 2
0.5814 Remote Similarity NPD4634 Approved
0.5798 Remote Similarity NPD7637 Suspended
0.5797 Remote Similarity NPD8451 Approved
0.5794 Remote Similarity NPD5141 Approved
0.5789 Remote Similarity NPD6110 Phase 1
0.5781 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5769 Remote Similarity NPD2204 Approved
0.5769 Remote Similarity NPD1719 Phase 1
0.5763 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5763 Remote Similarity NPD6101 Approved
0.576 Remote Similarity NPD5091 Approved
0.5755 Remote Similarity NPD8448 Approved
0.5739 Remote Similarity NPD5766 Clinical (unspecified phase)
0.5735 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5726 Remote Similarity NPD5286 Approved
0.5726 Remote Similarity NPD7524 Approved
0.5726 Remote Similarity NPD5285 Approved
0.5726 Remote Similarity NPD4696 Approved
0.5725 Remote Similarity NPD8341 Approved
0.5725 Remote Similarity NPD8299 Approved
0.5725 Remote Similarity NPD8340 Approved
0.5725 Remote Similarity NPD8342 Approved
0.5714 Remote Similarity NPD6274 Approved
0.5691 Remote Similarity NPD4755 Approved
0.5682 Remote Similarity NPD8133 Approved
0.5676 Remote Similarity NPD8384 Approved
0.5667 Remote Similarity NPD5693 Phase 1
0.5667 Remote Similarity NPD5284 Approved
0.5667 Remote Similarity NPD6411 Approved
0.5667 Remote Similarity NPD5281 Approved
0.5659 Remote Similarity NPD5168 Approved
0.5656 Remote Similarity NPD5654 Approved
0.5656 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5652 Remote Similarity NPD8328 Phase 3
0.5649 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5635 Remote Similarity NPD5226 Approved
0.5635 Remote Similarity NPD7632 Discontinued
0.5635 Remote Similarity NPD5224 Approved
0.5635 Remote Similarity NPD5225 Approved
0.5635 Remote Similarity NPD3653 Clinical (unspecified phase)
0.5635 Remote Similarity NPD4633 Approved
0.5634 Remote Similarity NPD8391 Approved
0.5634 Remote Similarity NPD8390 Approved
0.5634 Remote Similarity NPD8392 Approved
0.562 Remote Similarity NPD8444 Approved
0.5603 Remote Similarity NPD7338 Clinical (unspecified phase)
0.56 Remote Similarity NPD4700 Approved

Structure

External Identifiers

PubChem CID   5281447
ChEMBL   CHEMBL250952
ZINC  

Physicochemical Properties

Molecular Weight:  454.14
ALogP:  1.2741
MLogP:  2.89
XLogP:  1.229
# Rotatable Bonds:  13
Polar Surface Area:  119.36
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  31

Download Data

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