Natural Product: NPC258711

Natural Product ID:  NPC258711
Common Name:   Eupachlorin
IUPAC Name:   [(3aR,4R,6R,6aR,7R,9aS,9bS)-6-(chloromethyl)-6,7,9a-trihydroxy-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
Molecular Formula:   C20H25ClO7
Standard InCHIKey:  VCAKAFVZYNRGKS-WBNZXOOCSA-N
Standard InCHI:  InChI=1S/C20H25ClO7/c1-5-9(2)17(23)27-13-7-19(25,8-21)15-12(22)6-10(3)20(15,26)16-14(13)11(4)18(24)28-16/h5-6,12-16,22,25-26H,4,7-8H2,1-3H3/b9-5-/t12-,13-,14-,15+,16+,19+,20-/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]2O)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
NPO33469 Asteraceae Family Asteraceae Eukaryota PMID[18329753]
NPO26385 Eupatorium rotundifolium Species Asteraceae Eukaryota TCM_Taiwan*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT91 Cell Line KB Homo sapiens ED50 = 0.21 ug/ml 17336532
NPT91 Cell Line KB Homo sapiens ED50 = 0.51 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 NPC258711 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 NPC35069
0.9808 High Similarity NPC95290
0.9808 High Similarity NPC189338
0.9417 High Similarity NPC166115
0.9048 High Similarity NPC243998
0.9 High Similarity NPC255450
0.9 High Similarity NPC170692
0.8909 High Similarity NPC121816
0.8868 High Similarity NPC223450
0.8818 High Similarity NPC273242
0.8762 High Similarity NPC86077
0.8598 High Similarity NPC100487
0.8532 High Similarity NPC68248
0.8447 Intermediate Similarity NPC477131
0.8365 Intermediate Similarity NPC304886
0.835 Intermediate Similarity NPC475912
0.8349 Intermediate Similarity NPC54737
0.8318 Intermediate Similarity NPC150923
0.8269 Intermediate Similarity NPC262133
0.8269 Intermediate Similarity NPC470010
0.8269 Intermediate Similarity NPC323008
0.8269 Intermediate Similarity NPC470013
0.8269 Intermediate Similarity NPC198853
0.8257 Intermediate Similarity NPC203659
0.8252 Intermediate Similarity NPC133698
0.8252 Intermediate Similarity NPC131209
0.819 Intermediate Similarity NPC14961
0.819 Intermediate Similarity NPC270013
0.819 Intermediate Similarity NPC36954
0.8173 Intermediate Similarity NPC135776
0.8173 Intermediate Similarity NPC81419
0.8173 Intermediate Similarity NPC179746
0.8165 Intermediate Similarity NPC475945
0.8165 Intermediate Similarity NPC110989
0.8165 Intermediate Similarity NPC475871
0.8125 Intermediate Similarity NPC59489
0.8125 Intermediate Similarity NPC115352
0.8125 Intermediate Similarity NPC139838
0.8108 Intermediate Similarity NPC26617
0.8095 Intermediate Similarity NPC81386
0.8095 Intermediate Similarity NPC474035
0.8077 Intermediate Similarity NPC30515
0.8077 Intermediate Similarity NPC12172
0.8077 Intermediate Similarity NPC184463
0.8077 Intermediate Similarity NPC208886
0.8073 Intermediate Similarity NPC474747
0.8073 Intermediate Similarity NPC225353
0.8037 Intermediate Similarity NPC471150
0.8037 Intermediate Similarity NPC161493
0.8019 Intermediate Similarity NPC52044
0.8019 Intermediate Similarity NPC67584
0.8 Intermediate Similarity NPC124881
0.8 Intermediate Similarity NPC212486
0.8 Intermediate Similarity NPC476300
0.7982 Intermediate Similarity NPC474742
0.7981 Intermediate Similarity NPC51004
0.7981 Intermediate Similarity NPC474761
0.7981 Intermediate Similarity NPC476004
0.7963 Intermediate Similarity NPC473326
0.7963 Intermediate Similarity NPC187268
0.7961 Intermediate Similarity NPC202672
0.7944 Intermediate Similarity NPC476315
0.7944 Intermediate Similarity NPC213078
0.7928 Intermediate Similarity NPC474741
0.7905 Intermediate Similarity NPC475925
0.7905 Intermediate Similarity NPC473321
0.7895 Intermediate Similarity NPC257240
0.789 Intermediate Similarity NPC288876
0.789 Intermediate Similarity NPC70865
0.789 Intermediate Similarity NPC471381
0.789 Intermediate Similarity NPC186861
0.7885 Intermediate Similarity NPC32922
0.7885 Intermediate Similarity NPC307411
0.7885 Intermediate Similarity NPC295312
0.785 Intermediate Similarity NPC213698
0.785 Intermediate Similarity NPC472873
0.785 Intermediate Similarity NPC220221
0.785 Intermediate Similarity NPC170120
0.783 Intermediate Similarity NPC295204
0.783 Intermediate Similarity NPC288240
0.783 Intermediate Similarity NPC273579
0.783 Intermediate Similarity NPC162205
0.7818 Intermediate Similarity NPC171759
0.781 Intermediate Similarity NPC473619
0.781 Intermediate Similarity NPC129419
0.7798 Intermediate Similarity NPC474213
0.7798 Intermediate Similarity NPC141191
0.7798 Intermediate Similarity NPC221615
0.7788 Intermediate Similarity NPC91248
0.7788 Intermediate Similarity NPC153805
0.7778 Intermediate Similarity NPC18019
0.7778 Intermediate Similarity NPC279621
0.7778 Intermediate Similarity NPC24956
0.7757 Intermediate Similarity NPC127019
0.7757 Intermediate Similarity NPC303942
0.7757 Intermediate Similarity NPC57405
0.7739 Intermediate Similarity NPC477103
0.7724 Intermediate Similarity NPC470973
0.7714 Intermediate Similarity NPC215556
0.7714 Intermediate Similarity NPC268298
0.7714 Intermediate Similarity NPC474032
0.7706 Intermediate Similarity NPC169205
0.7706 Intermediate Similarity NPC108475
0.7706 Intermediate Similarity NPC181151
0.7706 Intermediate Similarity NPC170143
0.7706 Intermediate Similarity NPC474313
0.7706 Intermediate Similarity NPC213947
0.7692 Intermediate Similarity NPC46269
0.7692 Intermediate Similarity NPC190753
0.7692 Intermediate Similarity NPC186148
0.7692 Intermediate Similarity NPC106395
0.7685 Intermediate Similarity NPC163228
0.7685 Intermediate Similarity NPC476053
0.7685 Intermediate Similarity NPC471142
0.7679 Intermediate Similarity NPC475873
0.7672 Intermediate Similarity NPC287311
0.767 Intermediate Similarity NPC21469
0.7664 Intermediate Similarity NPC475838
0.7664 Intermediate Similarity NPC125674
0.7664 Intermediate Similarity NPC228451
0.7658 Intermediate Similarity NPC185141
0.7658 Intermediate Similarity NPC46998
0.7658 Intermediate Similarity NPC133907
0.7658 Intermediate Similarity NPC110443
0.7658 Intermediate Similarity NPC476270
0.7658 Intermediate Similarity NPC128733
0.7652 Intermediate Similarity NPC477102
0.7652 Intermediate Similarity NPC273433
0.7647 Intermediate Similarity NPC475323
0.7642 Intermediate Similarity NPC301969
0.7642 Intermediate Similarity NPC475855
0.7642 Intermediate Similarity NPC216284
0.7642 Intermediate Similarity NPC473448
0.7642 Intermediate Similarity NPC71533
0.7642 Intermediate Similarity NPC106510
0.7642 Intermediate Similarity NPC37607
0.7636 Intermediate Similarity NPC471144
0.7627 Intermediate Similarity NPC138303
0.7627 Intermediate Similarity NPC67290
0.7627 Intermediate Similarity NPC133677
0.7627 Intermediate Similarity NPC471380
0.7619 Intermediate Similarity NPC178875
0.7619 Intermediate Similarity NPC227379
0.7619 Intermediate Similarity NPC79549
0.7619 Intermediate Similarity NPC177629
0.7619 Intermediate Similarity NPC474471
0.7619 Intermediate Similarity NPC58219
0.7619 Intermediate Similarity NPC473715
0.7619 Intermediate Similarity NPC217983
0.7619 Intermediate Similarity NPC207114
0.7615 Intermediate Similarity NPC473859
0.7615 Intermediate Similarity NPC477921
0.7615 Intermediate Similarity NPC476009
0.7615 Intermediate Similarity NPC185553
0.7607 Intermediate Similarity NPC123855
0.7607 Intermediate Similarity NPC138757
0.7607 Intermediate Similarity NPC76550
0.7593 Intermediate Similarity NPC474247
0.7593 Intermediate Similarity NPC473316
0.7593 Intermediate Similarity NPC474338
0.7593 Intermediate Similarity NPC473330
0.7589 Intermediate Similarity NPC149371
0.7586 Intermediate Similarity NPC5103
0.757 Intermediate Similarity NPC261607
0.757 Intermediate Similarity NPC300312
0.757 Intermediate Similarity NPC111114
0.757 Intermediate Similarity NPC184063
0.7565 Intermediate Similarity NPC475960
0.7565 Intermediate Similarity NPC117604
0.7565 Intermediate Similarity NPC308191
0.7563 Intermediate Similarity NPC329869
0.7547 Intermediate Similarity NPC473564
0.7547 Intermediate Similarity NPC4986
0.7547 Intermediate Similarity NPC92974
0.7545 Intermediate Similarity NPC245521
0.7545 Intermediate Similarity NPC40812
0.7544 Intermediate Similarity NPC179891
0.7542 Intermediate Similarity NPC209058
0.7524 Intermediate Similarity NPC231889
0.7524 Intermediate Similarity NPC248602
0.7524 Intermediate Similarity NPC118601
0.7524 Intermediate Similarity NPC237540
0.7524 Intermediate Similarity NPC160138
0.7523 Intermediate Similarity NPC477922
0.7523 Intermediate Similarity NPC475900
0.7523 Intermediate Similarity NPC224689
0.7523 Intermediate Similarity NPC193645
0.7523 Intermediate Similarity NPC90121
0.7523 Intermediate Similarity NPC475659
0.7523 Intermediate Similarity NPC275960
0.7523 Intermediate Similarity NPC48803
0.7522 Intermediate Similarity NPC474775
0.7522 Intermediate Similarity NPC472755
0.75 Intermediate Similarity NPC471145
0.75 Intermediate Similarity NPC477950
0.75 Intermediate Similarity NPC38154
0.75 Intermediate Similarity NPC258216
0.75 Intermediate Similarity NPC137033
0.75 Intermediate Similarity NPC471146
0.75 Intermediate Similarity NPC47880

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC258711 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
0.8108 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7895 Intermediate Similarity NPD6371 Approved
0.7547 Intermediate Similarity NPD1695 Approved
0.7523 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7167 Intermediate Similarity NPD6053 Discontinued
0.7156 Intermediate Similarity NPD46 Approved
0.7156 Intermediate Similarity NPD6698 Approved
0.7009 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.6937 Remote Similarity NPD7983 Approved
0.685 Remote Similarity NPD5983 Phase 2
0.6847 Remote Similarity NPD7838 Discovery
0.6829 Remote Similarity NPD4632 Approved
0.6822 Remote Similarity NPD5362 Discontinued
0.6789 Remote Similarity NPD4249 Approved
0.6727 Remote Similarity NPD4250 Approved
0.6727 Remote Similarity NPD4251 Approved
0.6724 Remote Similarity NPD4225 Approved
0.6696 Remote Similarity NPD5785 Approved
0.6694 Remote Similarity NPD6686 Approved
0.6667 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6641 Remote Similarity NPD6336 Discontinued
0.6641 Remote Similarity NPD7507 Approved
0.661 Remote Similarity NPD5344 Discontinued
0.6581 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6562 Remote Similarity NPD7100 Approved
0.6552 Remote Similarity NPD4792 Clinical (unspecified phase)
0.6545 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6545 Remote Similarity NPD5363 Approved
0.6541 Remote Similarity NPD6033 Approved
0.6535 Remote Similarity NPD6009 Approved
0.6535 Remote Similarity NPD7115 Discovery
0.6522 Remote Similarity NPD5282 Discontinued
0.6514 Remote Similarity NPD7154 Phase 3
0.6493 Remote Similarity NPD7319 Approved
0.6486 Remote Similarity NPD5786 Approved
0.6484 Remote Similarity NPD6313 Approved
0.6484 Remote Similarity NPD6335 Approved
0.6484 Remote Similarity NPD6314 Approved
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
0.6444 Remote Similarity NPD5956 Approved
0.6435 Remote Similarity NPD5779 Approved
0.6435 Remote Similarity NPD5778 Approved
0.6434 Remote Similarity NPD7101 Approved
0.6422 Remote Similarity NPD6435 Approved
0.6393 Remote Similarity NPD6008 Approved
0.6389 Remote Similarity NPD4821 Approved
0.6389 Remote Similarity NPD4820 Approved
0.6389 Remote Similarity NPD4819 Approved
0.6389 Remote Similarity NPD4822 Approved
0.6389 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6385 Remote Similarity NPD6319 Approved
0.6316 Remote Similarity NPD7492 Approved
0.6273 Remote Similarity NPD4270 Approved
0.6273 Remote Similarity NPD4269 Approved
0.627 Remote Similarity NPD5215 Approved
0.6269 Remote Similarity NPD6616 Approved
0.626 Remote Similarity NPD6054 Approved
0.625 Remote Similarity NPD7640 Approved
0.625 Remote Similarity NPD6648 Approved
0.625 Remote Similarity NPD7639 Approved
0.624 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6239 Remote Similarity NPD5368 Approved
0.6222 Remote Similarity NPD7078 Approved
0.6222 Remote Similarity NPD8074 Phase 3
0.622 Remote Similarity NPD8297 Approved
0.6216 Remote Similarity NPD5332 Approved
0.6216 Remote Similarity NPD5331 Approved
0.6212 Remote Similarity NPD6015 Approved
0.6212 Remote Similarity NPD6016 Approved
0.621 Remote Similarity NPD5697 Approved
0.6204 Remote Similarity NPD4268 Approved
0.6204 Remote Similarity NPD4271 Approved
0.619 Remote Similarity NPD5169 Approved
0.6183 Remote Similarity NPD4522 Approved
0.6182 Remote Similarity NPD5369 Approved
0.6182 Remote Similarity NPD4790 Discontinued
0.6176 Remote Similarity NPD7736 Approved
0.6167 Remote Similarity NPD7638 Approved
0.6165 Remote Similarity NPD5988 Approved
0.6165 Remote Similarity NPD6370 Approved
0.616 Remote Similarity NPD7320 Approved
0.616 Remote Similarity NPD6881 Approved
0.616 Remote Similarity NPD6899 Approved
0.6142 Remote Similarity NPD5216 Approved
0.6142 Remote Similarity NPD6650 Approved
0.6142 Remote Similarity NPD5127 Approved
0.6142 Remote Similarity NPD6649 Approved
0.6142 Remote Similarity NPD5217 Approved
0.6136 Remote Similarity NPD6059 Approved
0.6129 Remote Similarity NPD7128 Approved
0.6129 Remote Similarity NPD5739 Approved
0.6129 Remote Similarity NPD6402 Approved
0.6129 Remote Similarity NPD6675 Approved
0.6124 Remote Similarity NPD5167 Approved
0.6111 Remote Similarity NPD6372 Approved
0.6111 Remote Similarity NPD6014 Approved
0.6111 Remote Similarity NPD6373 Approved
0.6111 Remote Similarity NPD6013 Approved
0.6111 Remote Similarity NPD6012 Approved
0.6107 Remote Similarity NPD7327 Approved
0.6107 Remote Similarity NPD7328 Approved
0.6103 Remote Similarity NPD8293 Discontinued
0.6091 Remote Similarity NPD4252 Approved
0.609 Remote Similarity NPD8033 Approved
0.608 Remote Similarity NPD5701 Approved
0.608 Remote Similarity NPD6412 Phase 2
0.6077 Remote Similarity NPD6868 Approved
0.6063 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6063 Remote Similarity NPD6883 Approved
0.6063 Remote Similarity NPD7102 Approved
0.6063 Remote Similarity NPD7290 Approved
0.6061 Remote Similarity NPD7516 Approved
0.6056 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6055 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6032 Remote Similarity NPD6011 Approved
0.6032 Remote Similarity NPD5128 Approved
0.6016 Remote Similarity NPD6617 Approved
0.6016 Remote Similarity NPD8130 Phase 1
0.6016 Remote Similarity NPD6847 Approved
0.6016 Remote Similarity NPD6869 Approved
0.6016 Remote Similarity NPD5211 Phase 2
0.6015 Remote Similarity NPD8294 Approved
0.6015 Remote Similarity NPD8377 Approved
0.6 Remote Similarity NPD7604 Phase 2
0.6 Remote Similarity NPD7839 Suspended
0.6 Remote Similarity NPD7642 Approved
0.5982 Remote Similarity NPD4752 Clinical (unspecified phase)
0.597 Remote Similarity NPD8378 Approved
0.597 Remote Similarity NPD8379 Approved
0.597 Remote Similarity NPD8335 Approved
0.597 Remote Similarity NPD7503 Approved
0.597 Remote Similarity NPD8296 Approved
0.597 Remote Similarity NPD8380 Approved
0.5969 Remote Similarity NPD6882 Approved
0.5965 Remote Similarity NPD1694 Approved
0.595 Remote Similarity NPD6083 Phase 2
0.595 Remote Similarity NPD6084 Phase 2
0.5938 Remote Similarity NPD4634 Approved
0.5932 Remote Similarity NPD7637 Suspended
0.5929 Remote Similarity NPD7260 Phase 2
0.5929 Remote Similarity NPD6110 Phase 1
0.592 Remote Similarity NPD5141 Approved
0.5917 Remote Similarity NPD5695 Phase 3
0.5912 Remote Similarity NPD8273 Phase 1
0.5906 Remote Similarity NPD5345 Clinical (unspecified phase)
0.5902 Remote Similarity NPD5696 Approved
0.5897 Remote Similarity NPD5764 Clinical (unspecified phase)
0.5897 Remote Similarity NPD6101 Approved
0.5891 Remote Similarity NPD1719 Phase 1
0.5887 Remote Similarity NPD6845 Suspended
0.5882 Remote Similarity NPD7829 Approved
0.5882 Remote Similarity NPD7830 Approved
0.5882 Remote Similarity NPD6399 Phase 3
0.5877 Remote Similarity NPD5766 Clinical (unspecified phase)
0.5865 Remote Similarity NPD7641 Discontinued
0.5862 Remote Similarity NPD7524 Approved
0.5854 Remote Similarity NPD5285 Approved
0.5854 Remote Similarity NPD5286 Approved
0.5854 Remote Similarity NPD4696 Approved
0.5852 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5841 Remote Similarity NPD4800 Clinical (unspecified phase)
0.5841 Remote Similarity NPD5209 Approved
0.5833 Remote Similarity NPD6274 Approved
0.5827 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5827 Remote Similarity NPD6614 Approved
0.582 Remote Similarity NPD4755 Approved
0.5798 Remote Similarity NPD6411 Approved
0.5797 Remote Similarity NPD8451 Approved
0.5781 Remote Similarity NPD5168 Approved
0.5769 Remote Similarity NPD2204 Approved
0.5769 Remote Similarity NPD6401 Clinical (unspecified phase)
0.576 Remote Similarity NPD5224 Approved
0.576 Remote Similarity NPD4633 Approved
0.576 Remote Similarity NPD5225 Approved
0.576 Remote Similarity NPD5226 Approved
0.576 Remote Similarity NPD5091 Approved
0.576 Remote Similarity NPD7632 Discontinued
0.5755 Remote Similarity NPD8448 Approved
0.5739 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5726 Remote Similarity NPD4700 Approved
0.5725 Remote Similarity NPD8340 Approved
0.5725 Remote Similarity NPD8341 Approved
0.5725 Remote Similarity NPD8299 Approved
0.5725 Remote Similarity NPD8342 Approved
0.5714 Remote Similarity NPD5175 Approved
0.5714 Remote Similarity NPD5174 Approved
0.5682 Remote Similarity NPD8133 Approved
0.568 Remote Similarity NPD5223 Approved
0.5676 Remote Similarity NPD8384 Approved
0.5672 Remote Similarity NPD6317 Approved
0.5667 Remote Similarity NPD5693 Phase 1
0.5667 Remote Similarity NPD5284 Approved
0.5667 Remote Similarity NPD5281 Approved
0.5656 Remote Similarity NPD4629 Approved
0.5656 Remote Similarity NPD5210 Approved
0.5656 Remote Similarity NPD5654 Approved
0.5656 Remote Similarity NPD6356 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   5281446
ChEMBL   CHEMBL437014
ZINC  

Physicochemical Properties

Molecular Weight:  412.13
ALogP:  0.895
MLogP:  2.78
XLogP:  0.489
# Rotatable Bonds:  11
Polar Surface Area:  113.29
# H-Bond Aceptor:  7
# H-Bond Donor:  3
# Rings:  3
# Heavy Atoms:  28

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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