Natural Product: NPC476009

Natural Product ID:  NPC476009
Common Name:   (1S,5S,6R,7S,9R,10S)-5-Methylbutanoyloxy-1,4,9-Trihydroxy-2-Oxaxanth-11-En-6,12-Olide
IUPAC Name:   [(3aR,5R,6S,7S,8S,8aR)-5,7-dihydroxy-7-(3-hydroxybutanoyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,6,8,8a-hexahydrocyclohepta[b]furan-8-yl] 2-methylbutanoate
Synonyms:  
Molecular Formula:   C20H30O8
Standard InCHIKey:  CFNPAWULBAZKEI-FOFWQADPSA-N
Standard InCHI:  InChI=1S/C20H30O8/c1-6-9(2)18(24)28-17-16-13(11(4)19(25)27-16)8-14(22)12(5)20(17,26)15(23)7-10(3)21/h9-10,12-14,16-17,21-22,26H,4,6-8H2,1-3,5H3/t9?,10?,12-,13+,14+,16+,17-,20+/m0/s1
Canonical SMILES:  CCC(C(=O)O[C@H]1[C@@H]2OC(=O)C(=C)[C@H]2C[C@H]([C@@H]([C@@]1(O)C(=O)CC(O)C)C)O)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
NPO21597 Ratibida columnifera Species Asteraceae Eukaryota PMID[10579870]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified ED50 > 20 ug/ml 16933872
NPT1851 Cell Line Col2 Homo sapiens ED50 = 8.7 ug/ml 22119127
NPT858 Cell Line LNCaP Homo sapiens ED50 = 8.1 ug/ml 19084294
NPT2 Others Unspecified ED50 = 9 ug/ml 23558238
NPT91 Cell Line KB Homo sapiens ED50 = 12.7 ug/ml 19786608
NPT2 Others Unspecified ED50 > 20 ug/ml 18393465
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 16.8 ug/ml 20092288

  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 NPC476009 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
0.9667 High Similarity NPC475900
0.9348 High Similarity NPC39859
0.9348 High Similarity NPC158416
0.9348 High Similarity NPC470883
0.9348 High Similarity NPC76862
0.9263 High Similarity NPC474747
0.9167 High Similarity NPC475945
0.9167 High Similarity NPC475871
0.913 High Similarity NPC190294
0.9043 High Similarity NPC474313
0.8958 High Similarity NPC474742
0.8901 High Similarity NPC173926
0.8878 High Similarity NPC474741
0.8842 High Similarity NPC328562
0.8842 High Similarity NPC323421
0.8776 High Similarity NPC475873
0.8763 High Similarity NPC47880
0.8737 High Similarity NPC31645
0.8696 High Similarity NPC474951
0.8696 High Similarity NPC92974
0.8681 High Similarity NPC186148
0.8681 High Similarity NPC190753
0.8673 High Similarity NPC149371
0.8646 High Similarity NPC471150
0.8632 High Similarity NPC163228
0.8617 High Similarity NPC475788
0.8602 High Similarity NPC65359
0.8587 High Similarity NPC177629
0.8587 High Similarity NPC58219
0.8571 High Similarity NPC475019
0.8571 High Similarity NPC474762
0.8571 High Similarity NPC474949
0.8571 High Similarity NPC201718
0.8571 High Similarity NPC470242
0.8571 High Similarity NPC476015
0.8557 High Similarity NPC471144
0.8542 High Similarity NPC142529
0.8542 High Similarity NPC91771
0.8526 High Similarity NPC473331
0.8511 High Similarity NPC184063
0.8511 High Similarity NPC184463
0.8511 High Similarity NPC329952
0.85 High Similarity NPC203659
0.8485 Intermediate Similarity NPC324017
0.8485 Intermediate Similarity NPC225353
0.8485 Intermediate Similarity NPC320019
0.8478 Intermediate Similarity NPC118601
0.8462 Intermediate Similarity NPC329749
0.8454 Intermediate Similarity NPC311904
0.8438 Intermediate Similarity NPC36954
0.8421 Intermediate Similarity NPC473263
0.8421 Intermediate Similarity NPC308656
0.8421 Intermediate Similarity NPC60386
0.8421 Intermediate Similarity NPC476300
0.8421 Intermediate Similarity NPC212486
0.8421 Intermediate Similarity NPC473234
0.8421 Intermediate Similarity NPC475912
0.8421 Intermediate Similarity NPC153590
0.8421 Intermediate Similarity NPC473273
0.8416 Intermediate Similarity NPC44004
0.8404 Intermediate Similarity NPC19087
0.84 Intermediate Similarity NPC472755
0.84 Intermediate Similarity NPC110989
0.8387 Intermediate Similarity NPC53158
0.8387 Intermediate Similarity NPC178875
0.8387 Intermediate Similarity NPC202672
0.8384 Intermediate Similarity NPC15993
0.8384 Intermediate Similarity NPC476270
0.8352 Intermediate Similarity NPC3464
0.8352 Intermediate Similarity NPC474780
0.8352 Intermediate Similarity NPC151176
0.8352 Intermediate Similarity NPC475963
0.8333 Intermediate Similarity NPC26617
0.8333 Intermediate Similarity NPC477513
0.8317 Intermediate Similarity NPC100487
0.8316 Intermediate Similarity NPC208886
0.8316 Intermediate Similarity NPC469627
0.8316 Intermediate Similarity NPC12172
0.8316 Intermediate Similarity NPC70251
0.8316 Intermediate Similarity NPC475881
0.8316 Intermediate Similarity NPC30515
0.83 Intermediate Similarity NPC472754
0.8298 Intermediate Similarity NPC38392
0.8298 Intermediate Similarity NPC12872
0.8298 Intermediate Similarity NPC168679
0.8298 Intermediate Similarity NPC307411
0.8283 Intermediate Similarity NPC471381
0.8283 Intermediate Similarity NPC475949
0.8283 Intermediate Similarity NPC186861
0.8261 Intermediate Similarity NPC47958
0.8261 Intermediate Similarity NPC149725
0.8261 Intermediate Similarity NPC304509
0.8247 Intermediate Similarity NPC472873
0.8247 Intermediate Similarity NPC270013
0.8247 Intermediate Similarity NPC14961
0.8229 Intermediate Similarity NPC81419
0.8229 Intermediate Similarity NPC179746
0.8229 Intermediate Similarity NPC200237
0.8218 Intermediate Similarity NPC473148
0.8211 Intermediate Similarity NPC474323
0.8211 Intermediate Similarity NPC51004
0.8211 Intermediate Similarity NPC206614
0.82 Intermediate Similarity NPC110443
0.82 Intermediate Similarity NPC133907
0.82 Intermediate Similarity NPC474339
0.82 Intermediate Similarity NPC46998
0.82 Intermediate Similarity NPC164598
0.82 Intermediate Similarity NPC171759
0.82 Intermediate Similarity NPC128733
0.82 Intermediate Similarity NPC185141
0.82 Intermediate Similarity NPC472753
0.8191 Intermediate Similarity NPC207114
0.8191 Intermediate Similarity NPC217983
0.8173 Intermediate Similarity NPC38154
0.8172 Intermediate Similarity NPC304558
0.8172 Intermediate Similarity NPC236692
0.8172 Intermediate Similarity NPC309757
0.8163 Intermediate Similarity NPC476315
0.8163 Intermediate Similarity NPC473859
0.8148 Intermediate Similarity NPC471146
0.8148 Intermediate Similarity NPC471145
0.8144 Intermediate Similarity NPC81386
0.8144 Intermediate Similarity NPC474035
0.8137 Intermediate Similarity NPC472756
0.8125 Intermediate Similarity NPC286341
0.8125 Intermediate Similarity NPC191339
0.8119 Intermediate Similarity NPC471148
0.8119 Intermediate Similarity NPC80144
0.8105 Intermediate Similarity NPC215556
0.81 Intermediate Similarity NPC288876
0.8085 Intermediate Similarity NPC5130
0.8081 Intermediate Similarity NPC170143
0.8081 Intermediate Similarity NPC213947
0.8081 Intermediate Similarity NPC108475
0.8061 Intermediate Similarity NPC475659
0.8061 Intermediate Similarity NPC476053
0.8061 Intermediate Similarity NPC471142
0.8058 Intermediate Similarity NPC54737
0.8058 Intermediate Similarity NPC243998
0.8058 Intermediate Similarity NPC223450
0.8043 Intermediate Similarity NPC128429
0.8041 Intermediate Similarity NPC469645
0.8041 Intermediate Similarity NPC135776
0.8041 Intermediate Similarity NPC469692
0.8039 Intermediate Similarity NPC4620
0.8021 Intermediate Similarity NPC216284
0.8021 Intermediate Similarity NPC476004
0.8021 Intermediate Similarity NPC297474
0.8021 Intermediate Similarity NPC54065
0.8021 Intermediate Similarity NPC474761
0.802 Intermediate Similarity NPC67296
0.8 Intermediate Similarity NPC249171
0.8 Intermediate Similarity NPC79549
0.8 Intermediate Similarity NPC49833
0.8 Intermediate Similarity NPC474213
0.8 Intermediate Similarity NPC59489
0.8 Intermediate Similarity NPC139838
0.7979 Intermediate Similarity NPC187661
0.7979 Intermediate Similarity NPC238593
0.7961 Intermediate Similarity NPC475676
0.7961 Intermediate Similarity NPC220964
0.7959 Intermediate Similarity NPC121825
0.7941 Intermediate Similarity NPC86077
0.7938 Intermediate Similarity NPC20713
0.7938 Intermediate Similarity NPC133888
0.7938 Intermediate Similarity NPC35959
0.7938 Intermediate Similarity NPC171360
0.7938 Intermediate Similarity NPC57304
0.7938 Intermediate Similarity NPC29821
0.7938 Intermediate Similarity NPC293001
0.7938 Intermediate Similarity NPC131209
0.7938 Intermediate Similarity NPC133698
0.7938 Intermediate Similarity NPC63193
0.7925 Intermediate Similarity NPC477103
0.7917 Intermediate Similarity NPC155935
0.7912 Intermediate Similarity NPC474981
0.7905 Intermediate Similarity NPC68248
0.7905 Intermediate Similarity NPC37628
0.79 Intermediate Similarity NPC181151
0.79 Intermediate Similarity NPC169205
0.79 Intermediate Similarity NPC304445
0.79 Intermediate Similarity NPC40812
0.79 Intermediate Similarity NPC236580
0.7895 Intermediate Similarity NPC248602
0.7895 Intermediate Similarity NPC201658
0.7885 Intermediate Similarity NPC474101
0.7879 Intermediate Similarity NPC322188
0.7879 Intermediate Similarity NPC48803
0.7879 Intermediate Similarity NPC193645
0.7879 Intermediate Similarity NPC275960
0.7879 Intermediate Similarity NPC90121
0.7879 Intermediate Similarity NPC304886
0.7857 Intermediate Similarity NPC295204
0.7857 Intermediate Similarity NPC273579
0.7857 Intermediate Similarity NPC288240
0.7857 Intermediate Similarity NPC162205
0.7857 Intermediate Similarity NPC475302
0.785 Intermediate Similarity NPC287311
0.7849 Intermediate Similarity NPC257358
0.7849 Intermediate Similarity NPC474472

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476009 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
0.8333 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7879 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7757 Intermediate Similarity NPD6371 Approved
0.74 Intermediate Similarity NPD7983 Approved
0.732 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.73 Intermediate Similarity NPD46 Approved
0.73 Intermediate Similarity NPD6698 Approved
0.7248 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.72 Intermediate Similarity NPD1695 Approved
0.7087 Intermediate Similarity NPD5282 Discontinued
0.7054 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.6961 Remote Similarity NPD7838 Discovery
0.6864 Remote Similarity NPD6319 Approved
0.6822 Remote Similarity NPD4225 Approved
0.6807 Remote Similarity NPD8516 Approved
0.6807 Remote Similarity NPD8513 Phase 3
0.6807 Remote Similarity NPD8515 Approved
0.6807 Remote Similarity NPD8517 Approved
0.6786 Remote Similarity NPD6686 Approved
0.6667 Remote Similarity NPD5778 Approved
0.6667 Remote Similarity NPD5779 Approved
0.6667 Remote Similarity NPD6921 Approved
0.6635 Remote Similarity NPD5785 Approved
0.6589 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6569 Remote Similarity NPD5786 Approved
0.6566 Remote Similarity NPD5369 Approved
0.6552 Remote Similarity NPD6053 Discontinued
0.6532 Remote Similarity NPD8074 Phase 3
0.6529 Remote Similarity NPD8267 Approved
0.6529 Remote Similarity NPD8268 Approved
0.6529 Remote Similarity NPD8269 Approved
0.6529 Remote Similarity NPD8266 Approved
0.6514 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6504 Remote Similarity NPD7492 Approved
0.65 Remote Similarity NPD6435 Approved
0.6496 Remote Similarity NPD4632 Approved
0.6471 Remote Similarity NPD7115 Discovery
0.6471 Remote Similarity NPD5363 Approved
0.6452 Remote Similarity NPD6616 Approved
0.6446 Remote Similarity NPD6054 Approved
0.6423 Remote Similarity NPD7642 Approved
0.6423 Remote Similarity NPD8328 Phase 3
0.641 Remote Similarity NPD8297 Approved
0.64 Remote Similarity NPD7078 Approved
0.6396 Remote Similarity NPD5344 Discontinued
0.6393 Remote Similarity NPD6016 Approved
0.6393 Remote Similarity NPD6015 Approved
0.6381 Remote Similarity NPD6101 Approved
0.6381 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6372 Remote Similarity NPD4057 Clinical (unspecified phase)
0.6372 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6356 Remote Similarity NPD8133 Approved
0.6349 Remote Similarity NPD7736 Approved
0.6341 Remote Similarity NPD6370 Approved
0.6341 Remote Similarity NPD8080 Discontinued
0.6341 Remote Similarity NPD5988 Approved
0.6337 Remote Similarity NPD4270 Approved
0.6337 Remote Similarity NPD4269 Approved
0.6337 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6333 Remote Similarity NPD8295 Clinical (unspecified phase)
0.633 Remote Similarity NPD7839 Suspended
0.6325 Remote Similarity NPD6649 Approved
0.6325 Remote Similarity NPD6650 Approved
0.6311 Remote Similarity NPD6059 Approved
0.63 Remote Similarity NPD5368 Approved
0.6299 Remote Similarity NPD7319 Approved
0.6293 Remote Similarity NPD6372 Approved
0.6293 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6293 Remote Similarity NPD6373 Approved
0.627 Remote Similarity NPD8293 Discontinued
0.6262 Remote Similarity NPD6411 Approved
0.6261 Remote Similarity NPD5697 Approved
0.626 Remote Similarity NPD8274 Clinical (unspecified phase)
0.625 Remote Similarity NPD4249 Approved
0.6239 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6239 Remote Similarity NPD4634 Approved
0.6207 Remote Similarity NPD6881 Approved
0.6207 Remote Similarity NPD6899 Approved
0.6202 Remote Similarity NPD7260 Phase 2
0.6198 Remote Similarity NPD6009 Approved
0.619 Remote Similarity NPD4250 Approved
0.619 Remote Similarity NPD7507 Approved
0.619 Remote Similarity NPD4251 Approved
0.619 Remote Similarity NPD8451 Approved
0.619 Remote Similarity NPD8273 Phase 1
0.6186 Remote Similarity NPD2204 Approved
0.6174 Remote Similarity NPD7128 Approved
0.6174 Remote Similarity NPD6402 Approved
0.6174 Remote Similarity NPD5739 Approved
0.6174 Remote Similarity NPD6675 Approved
0.616 Remote Similarity NPD7829 Approved
0.616 Remote Similarity NPD7830 Approved
0.6154 Remote Similarity NPD6012 Approved
0.6154 Remote Similarity NPD6845 Suspended
0.6154 Remote Similarity NPD6014 Approved
0.6154 Remote Similarity NPD6013 Approved
0.6148 Remote Similarity NPD7641 Discontinued
0.6142 Remote Similarity NPD8448 Approved
0.6139 Remote Similarity NPD4252 Approved
0.6134 Remote Similarity NPD6882 Approved
0.6129 Remote Similarity NPD5983 Phase 2
0.6129 Remote Similarity NPD8444 Approved
0.6121 Remote Similarity NPD5701 Approved
0.6117 Remote Similarity NPD7154 Phase 3
0.6117 Remote Similarity NPD6110 Phase 1
0.6102 Remote Similarity NPD7290 Approved
0.6102 Remote Similarity NPD6883 Approved
0.6102 Remote Similarity NPD7102 Approved
0.6068 Remote Similarity NPD7320 Approved
0.6068 Remote Similarity NPD6011 Approved
0.6066 Remote Similarity NPD8137 Clinical (unspecified phase)
0.605 Remote Similarity NPD6869 Approved
0.605 Remote Similarity NPD6847 Approved
0.605 Remote Similarity NPD8130 Phase 1
0.605 Remote Similarity NPD6617 Approved
0.6034 Remote Similarity NPD6008 Approved
0.6032 Remote Similarity NPD7604 Phase 2
0.6018 Remote Similarity NPD6648 Approved
0.6 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6 Remote Similarity NPD1694 Approved
0.6 Remote Similarity NPD8392 Approved
0.6 Remote Similarity NPD8391 Approved
0.6 Remote Similarity NPD8390 Approved
0.5984 Remote Similarity NPD8341 Approved
0.5984 Remote Similarity NPD8299 Approved
0.5984 Remote Similarity NPD8340 Approved
0.5984 Remote Similarity NPD8342 Approved
0.5983 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5983 Remote Similarity NPD6412 Phase 2
0.5982 Remote Similarity NPD6083 Phase 2
0.5982 Remote Similarity NPD6084 Phase 2
0.598 Remote Similarity NPD4819 Approved
0.598 Remote Similarity NPD4820 Approved
0.598 Remote Similarity NPD5790 Clinical (unspecified phase)
0.598 Remote Similarity NPD4822 Approved
0.598 Remote Similarity NPD4821 Approved
0.5965 Remote Similarity NPD1700 Approved
0.5962 Remote Similarity NPD5362 Discontinued
0.5946 Remote Similarity NPD5695 Phase 3
0.5938 Remote Similarity NPD6336 Discontinued
0.5929 Remote Similarity NPD7638 Approved
0.5929 Remote Similarity NPD5696 Approved
0.5914 Remote Similarity NPD7909 Approved
0.5913 Remote Similarity NPD8085 Approved
0.5913 Remote Similarity NPD8084 Approved
0.5913 Remote Similarity NPD8139 Approved
0.5913 Remote Similarity NPD8138 Approved
0.5913 Remote Similarity NPD5211 Phase 2
0.5913 Remote Similarity NPD8086 Approved
0.5913 Remote Similarity NPD8082 Approved
0.5913 Remote Similarity NPD8083 Approved
0.5909 Remote Similarity NPD6399 Phase 3
0.5896 Remote Similarity NPD8387 Clinical (unspecified phase)
0.5882 Remote Similarity NPD8132 Clinical (unspecified phase)
0.5877 Remote Similarity NPD5286 Approved
0.5877 Remote Similarity NPD4696 Approved
0.5877 Remote Similarity NPD7639 Approved
0.5877 Remote Similarity NPD5285 Approved
0.5877 Remote Similarity NPD7640 Approved
0.5865 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5865 Remote Similarity NPD5209 Approved
0.5862 Remote Similarity NPD8276 Approved
0.5862 Remote Similarity NPD8275 Approved
0.5854 Remote Similarity NPD6274 Approved
0.5846 Remote Similarity NPD6033 Approved
0.5843 Remote Similarity NPD73 Approved
0.5841 Remote Similarity NPD4755 Approved
0.5821 Remote Similarity NPD8415 Approved
0.5818 Remote Similarity NPD7637 Suspended
0.5812 Remote Similarity NPD5141 Approved
0.5812 Remote Similarity NPD8081 Approved
0.5785 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5784 Remote Similarity NPD4271 Approved
0.5784 Remote Similarity NPD4802 Phase 2
0.5784 Remote Similarity NPD4268 Approved
0.5784 Remote Similarity NPD5784 Clinical (unspecified phase)
0.5784 Remote Similarity NPD4238 Approved
0.5776 Remote Similarity NPD5224 Approved
0.5776 Remote Similarity NPD5225 Approved
0.5776 Remote Similarity NPD4633 Approved
0.5776 Remote Similarity NPD5226 Approved
0.5763 Remote Similarity NPD8393 Approved
0.5758 Remote Similarity NPD5956 Approved
0.5748 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5739 Remote Similarity NPD4700 Approved
0.5729 Remote Similarity NPD896 Approved
0.5729 Remote Similarity NPD897 Approved
0.5729 Remote Similarity NPD898 Approved
0.5726 Remote Similarity NPD5174 Approved
0.5726 Remote Similarity NPD5175 Approved
0.5714 Remote Similarity NPD7101 Approved
0.5714 Remote Similarity NPD7100 Approved
0.569 Remote Similarity NPD5223 Approved
0.568 Remote Similarity NPD7500 Approved
0.568 Remote Similarity NPD6317 Approved
0.5676 Remote Similarity NPD8035 Phase 2
0.5676 Remote Similarity NPD5693 Phase 1
0.5676 Remote Similarity NPD8034 Phase 2
0.5667 Remote Similarity NPD4730 Approved
0.5667 Remote Similarity NPD4729 Approved

Structure

External Identifiers

PubChem CID   44575375
ChEMBL   CHEMBL521423
ZINC  

Physicochemical Properties

Molecular Weight:  398.19
ALogP:  -1.5744
MLogP:  2.78
XLogP:  -0.136
# Rotatable Bonds:  14
Polar Surface Area:  130.36
# H-Bond Aceptor:  8
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  28

Download Data

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