Natural Product: NPC118601

Natural Product ID:  NPC118601
Common Name:   (3As,6R,6Ar,9Ar,9Bs)-6-Hydroxy-6-Methyl-3,9-Dimethyleneoctahydroazuleno[4,5-B]Furan-2,8(3H,9Bh)-Dione
IUPAC Name:   (3aS,6R,6aR,9aR,9bS)-6-hydroxy-6-methyl-3,9-dimethylidene-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-2,8-dione
Synonyms:  
Molecular Formula:   C15H18O4
Standard InCHIKey:  ZFIYHRXIURBIFJ-WXDRJKLISA-N
Standard InCHI:  InChI=1S/C15H18O4/c1-7-9-4-5-15(3,18)10-6-11(16)8(2)12(10)13(9)19-14(7)17/h9-10,12-13,18H,1-2,4-6H2,3H3/t9-,10+,12-,13-,15+/m0/s1
Canonical SMILES:  C=C1C(=O)C[C@@H]2[C@H]1[C@H]1OC(=O)C(=C)[C@@H]1CC[C@@]2(C)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
NPO10533 Ixeris chinensis Species Asteraceae Eukaryota PMID[17067155]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT81 Cell Line A549 Homo sapiens IC50 = 64900 nM 24440480
NPT81 Cell Line A549 Homo sapiens IC50 = 10900 nM 18268091
NPT81 Cell Line A549 Homo sapiens IC50 = 11400 nM 20850299

  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 NPC118601 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
0.9878 High Similarity NPC178875
0.9419 High Similarity NPC153590
0.9205 High Similarity NPC163228
0.9195 High Similarity NPC135776
0.9176 High Similarity NPC79549
0.9167 High Similarity NPC470242
0.9167 High Similarity NPC309757
0.9167 High Similarity NPC236692
0.907 High Similarity NPC215556
0.9048 High Similarity NPC204105
0.9048 High Similarity NPC284534
0.9048 High Similarity NPC300082
0.8989 High Similarity NPC476053
0.8977 High Similarity NPC308656
0.8977 High Similarity NPC200237
0.8977 High Similarity NPC60386
0.8977 High Similarity NPC473273
0.8977 High Similarity NPC473234
0.8977 High Similarity NPC473263
0.8966 High Similarity NPC216284
0.8953 High Similarity NPC217983
0.8953 High Similarity NPC207114
0.8941 High Similarity NPC187661
0.8929 High Similarity NPC224386
0.8929 High Similarity NPC194859
0.8916 High Similarity NPC246076
0.8889 High Similarity NPC91771
0.8889 High Similarity NPC142529
0.8876 High Similarity NPC473331
0.8864 High Similarity NPC155215
0.8864 High Similarity NPC184063
0.8851 High Similarity NPC12872
0.8851 High Similarity NPC32922
0.8851 High Similarity NPC168679
0.8851 High Similarity NPC155935
0.8837 High Similarity NPC190753
0.8837 High Similarity NPC270270
0.881 High Similarity NPC54468
0.8791 High Similarity NPC471150
0.8765 High Similarity NPC208223
0.8764 High Similarity NPC258216
0.875 High Similarity NPC297474
0.875 High Similarity NPC19087
0.875 High Similarity NPC35809
0.875 High Similarity NPC54065
0.8721 High Similarity NPC56593
0.8721 High Similarity NPC67493
0.8675 High Similarity NPC73052
0.8675 High Similarity NPC293418
0.8675 High Similarity NPC51507
0.8675 High Similarity NPC290508
0.8652 High Similarity NPC133698
0.8652 High Similarity NPC57304
0.8652 High Similarity NPC131209
0.8652 High Similarity NPC35959
0.8652 High Similarity NPC29821
0.8652 High Similarity NPC191339
0.8652 High Similarity NPC171360
0.8652 High Similarity NPC133888
0.8652 High Similarity NPC293001
0.8652 High Similarity NPC286341
0.8652 High Similarity NPC63193
0.8636 High Similarity NPC38392
0.8621 High Similarity NPC201658
0.8621 High Similarity NPC186148
0.8602 High Similarity NPC471381
0.8602 High Similarity NPC186861
0.8588 High Similarity NPC245665
0.8588 High Similarity NPC128246
0.8587 High Similarity NPC213947
0.8587 High Similarity NPC311904
0.8587 High Similarity NPC108475
0.8587 High Similarity NPC170143
0.8571 High Similarity NPC475900
0.8571 High Similarity NPC472873
0.8571 High Similarity NPC126248
0.8523 High Similarity NPC91248
0.8523 High Similarity NPC177629
0.8523 High Similarity NPC58219
0.8511 High Similarity NPC171759
0.8506 High Similarity NPC304558
0.8506 High Similarity NPC64153
0.8506 High Similarity NPC238593
0.8478 Intermediate Similarity NPC476009
0.8462 Intermediate Similarity NPC477131
0.8462 Intermediate Similarity NPC127019
0.8462 Intermediate Similarity NPC323008
0.8462 Intermediate Similarity NPC470010
0.8462 Intermediate Similarity NPC470013
0.8462 Intermediate Similarity NPC262133
0.8462 Intermediate Similarity NPC198853
0.8452 Intermediate Similarity NPC258965
0.8452 Intermediate Similarity NPC156658
0.8444 Intermediate Similarity NPC475925
0.8427 Intermediate Similarity NPC92974
0.8427 Intermediate Similarity NPC472872
0.8409 Intermediate Similarity NPC24728
0.8395 Intermediate Similarity NPC143979
0.8395 Intermediate Similarity NPC320537
0.8391 Intermediate Similarity NPC235792
0.8387 Intermediate Similarity NPC474313
0.8372 Intermediate Similarity NPC111409
0.837 Intermediate Similarity NPC67584
0.837 Intermediate Similarity NPC213698
0.837 Intermediate Similarity NPC170120
0.837 Intermediate Similarity NPC52044
0.8353 Intermediate Similarity NPC47635
0.8333 Intermediate Similarity NPC62815
0.8333 Intermediate Similarity NPC301969
0.8333 Intermediate Similarity NPC37607
0.8315 Intermediate Similarity NPC202672
0.8315 Intermediate Similarity NPC471149
0.8298 Intermediate Similarity NPC45125
0.8295 Intermediate Similarity NPC474949
0.8295 Intermediate Similarity NPC162071
0.8295 Intermediate Similarity NPC475019
0.8295 Intermediate Similarity NPC474762
0.8295 Intermediate Similarity NPC476015
0.828 Intermediate Similarity NPC24956
0.828 Intermediate Similarity NPC213078
0.828 Intermediate Similarity NPC18019
0.8276 Intermediate Similarity NPC156485
0.8242 Intermediate Similarity NPC12172
0.8242 Intermediate Similarity NPC208886
0.8235 Intermediate Similarity NPC6823
0.8222 Intermediate Similarity NPC474951
0.8222 Intermediate Similarity NPC307411
0.8222 Intermediate Similarity NPC283409
0.8222 Intermediate Similarity NPC173926
0.8191 Intermediate Similarity NPC181151
0.8191 Intermediate Similarity NPC161493
0.8182 Intermediate Similarity NPC149725
0.8182 Intermediate Similarity NPC329749
0.8182 Intermediate Similarity NPC304509
0.8182 Intermediate Similarity NPC47958
0.8172 Intermediate Similarity NPC304886
0.8171 Intermediate Similarity NPC215030
0.8163 Intermediate Similarity NPC54737
0.8152 Intermediate Similarity NPC81419
0.8152 Intermediate Similarity NPC179746
0.8132 Intermediate Similarity NPC51004
0.8111 Intermediate Similarity NPC224652
0.8105 Intermediate Similarity NPC221615
0.8085 Intermediate Similarity NPC126156
0.8068 Intermediate Similarity NPC470238
0.8068 Intermediate Similarity NPC474780
0.8068 Intermediate Similarity NPC138647
0.8065 Intermediate Similarity NPC190294
0.8043 Intermediate Similarity NPC184463
0.8043 Intermediate Similarity NPC70251
0.8043 Intermediate Similarity NPC475881
0.8043 Intermediate Similarity NPC30515
0.8041 Intermediate Similarity NPC474747
0.8041 Intermediate Similarity NPC80144
0.8023 Intermediate Similarity NPC74673
0.8023 Intermediate Similarity NPC474981
0.8023 Intermediate Similarity NPC69271
0.8022 Intermediate Similarity NPC4986
0.8022 Intermediate Similarity NPC295312
0.8022 Intermediate Similarity NPC268298
0.8 Intermediate Similarity NPC5130
0.798 Intermediate Similarity NPC223450
0.798 Intermediate Similarity NPC243998
0.7979 Intermediate Similarity NPC48803
0.7979 Intermediate Similarity NPC275960
0.7979 Intermediate Similarity NPC90121
0.7979 Intermediate Similarity NPC193645
0.7959 Intermediate Similarity NPC475871
0.7959 Intermediate Similarity NPC475945
0.7957 Intermediate Similarity NPC475912
0.7957 Intermediate Similarity NPC472874
0.7957 Intermediate Similarity NPC212486
0.7957 Intermediate Similarity NPC475788
0.7957 Intermediate Similarity NPC476300
0.7955 Intermediate Similarity NPC39588
0.7955 Intermediate Similarity NPC272814
0.7955 Intermediate Similarity NPC128429
0.7955 Intermediate Similarity NPC474472
0.7955 Intermediate Similarity NPC257358
0.7938 Intermediate Similarity NPC67296
0.7938 Intermediate Similarity NPC150923
0.7938 Intermediate Similarity NPC474742
0.7935 Intermediate Similarity NPC129419
0.7935 Intermediate Similarity NPC474323
0.7935 Intermediate Similarity NPC206614
0.7935 Intermediate Similarity NPC106510
0.7935 Intermediate Similarity NPC71533
0.7931 Intermediate Similarity NPC35089
0.7931 Intermediate Similarity NPC10276
0.7921 Intermediate Similarity NPC139838
0.7921 Intermediate Similarity NPC59489
0.7917 Intermediate Similarity NPC249171
0.7917 Intermediate Similarity NPC49833
0.7912 Intermediate Similarity NPC53158
0.7907 Intermediate Similarity NPC182550
0.7901 Intermediate Similarity NPC5714
0.7895 Intermediate Similarity NPC470883
0.7895 Intermediate Similarity NPC31645
0.7895 Intermediate Similarity NPC39859
0.7895 Intermediate Similarity NPC76862

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC118601 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
0.8022 Intermediate Similarity NPD1695 Approved
0.7979 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7549 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7391 Intermediate Similarity NPD1733 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD6053 Discontinued
0.7009 Intermediate Similarity NPD6371 Approved
0.6882 Remote Similarity NPD6435 Approved
0.6837 Remote Similarity NPD5785 Approved
0.68 Remote Similarity NPD5282 Discontinued
0.6792 Remote Similarity NPD6008 Approved
0.6774 Remote Similarity NPD5369 Approved
0.6771 Remote Similarity NPD5786 Approved
0.6771 Remote Similarity NPD4249 Approved
0.6701 Remote Similarity NPD4250 Approved
0.6701 Remote Similarity NPD4251 Approved
0.6667 Remote Similarity NPD5363 Approved
0.6667 Remote Similarity NPD46 Approved
0.6667 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5368 Approved
0.6667 Remote Similarity NPD6698 Approved
0.6632 Remote Similarity NPD5362 Discontinued
0.6535 Remote Similarity NPD6399 Phase 3
0.6526 Remote Similarity NPD4270 Approved
0.6526 Remote Similarity NPD4269 Approved
0.6495 Remote Similarity NPD1694 Approved
0.6436 Remote Similarity NPD7983 Approved
0.6381 Remote Similarity NPD7638 Approved
0.6373 Remote Similarity NPD5778 Approved
0.6373 Remote Similarity NPD5779 Approved
0.6337 Remote Similarity NPD7838 Discovery
0.6321 Remote Similarity NPD7640 Approved
0.6321 Remote Similarity NPD7639 Approved
0.6316 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6316 Remote Similarity NPD4820 Approved
0.6316 Remote Similarity NPD4822 Approved
0.6316 Remote Similarity NPD4821 Approved
0.6316 Remote Similarity NPD4819 Approved
0.6316 Remote Similarity NPD4252 Approved
0.6289 Remote Similarity NPD7154 Phase 3
0.6277 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6275 Remote Similarity NPD8034 Phase 2
0.6275 Remote Similarity NPD8035 Phase 2
0.6273 Remote Similarity NPD5697 Approved
0.6228 Remote Similarity NPD4632 Approved
0.6226 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6216 Remote Similarity NPD6881 Approved
0.6216 Remote Similarity NPD7320 Approved
0.6216 Remote Similarity NPD6011 Approved
0.6216 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6216 Remote Similarity NPD6899 Approved
0.6216 Remote Similarity NPD6686 Approved
0.6195 Remote Similarity NPD6649 Approved
0.6195 Remote Similarity NPD6650 Approved
0.6195 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6186 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6182 Remote Similarity NPD5739 Approved
0.6182 Remote Similarity NPD6402 Approved
0.6182 Remote Similarity NPD6675 Approved
0.6182 Remote Similarity NPD7128 Approved
0.6161 Remote Similarity NPD6373 Approved
0.6161 Remote Similarity NPD6014 Approved
0.6161 Remote Similarity NPD6012 Approved
0.6161 Remote Similarity NPD6372 Approved
0.6161 Remote Similarity NPD6013 Approved
0.616 Remote Similarity NPD6845 Suspended
0.6126 Remote Similarity NPD5701 Approved
0.6122 Remote Similarity NPD5332 Approved
0.6122 Remote Similarity NPD5331 Approved
0.6116 Remote Similarity NPD7492 Approved
0.6106 Remote Similarity NPD6883 Approved
0.6106 Remote Similarity NPD7102 Approved
0.6106 Remote Similarity NPD7290 Approved
0.6105 Remote Similarity NPD4802 Phase 2
0.6105 Remote Similarity NPD4268 Approved
0.6105 Remote Similarity NPD4271 Approved
0.6105 Remote Similarity NPD4238 Approved
0.6095 Remote Similarity NPD5695 Phase 3
0.6082 Remote Similarity NPD4790 Discontinued
0.608 Remote Similarity NPD7260 Phase 2
0.6078 Remote Similarity NPD6101 Approved
0.6078 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6075 Remote Similarity NPD5696 Approved
0.6075 Remote Similarity NPD4225 Approved
0.6068 Remote Similarity NPD7115 Discovery
0.6068 Remote Similarity NPD6009 Approved
0.6066 Remote Similarity NPD6616 Approved
0.6066 Remote Similarity NPD7507 Approved
0.6053 Remote Similarity NPD6847 Approved
0.6053 Remote Similarity NPD6617 Approved
0.6053 Remote Similarity NPD8130 Phase 1
0.6053 Remote Similarity NPD6869 Approved
0.605 Remote Similarity NPD6319 Approved
0.605 Remote Similarity NPD6054 Approved
0.6016 Remote Similarity NPD7078 Approved
0.6 Remote Similarity NPD8266 Approved
0.6 Remote Similarity NPD8267 Approved
0.6 Remote Similarity NPD6015 Approved
0.6 Remote Similarity NPD6882 Approved
0.6 Remote Similarity NPD8516 Approved
0.6 Remote Similarity NPD8515 Approved
0.6 Remote Similarity NPD8268 Approved
0.6 Remote Similarity NPD6016 Approved
0.6 Remote Similarity NPD8297 Approved
0.6 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6 Remote Similarity NPD8517 Approved
0.6 Remote Similarity NPD8513 Phase 3
0.6 Remote Similarity NPD8269 Approved
0.6 Remote Similarity NPD5983 Phase 2
0.5981 Remote Similarity NPD6083 Phase 2
0.5981 Remote Similarity NPD6084 Phase 2
0.598 Remote Similarity NPD6903 Approved
0.5968 Remote Similarity NPD7736 Approved
0.5965 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5963 Remote Similarity NPD5344 Discontinued
0.5962 Remote Similarity NPD5281 Approved
0.5962 Remote Similarity NPD5693 Phase 1
0.5962 Remote Similarity NPD6411 Approved
0.5962 Remote Similarity NPD5284 Approved
0.596 Remote Similarity NPD4788 Approved
0.595 Remote Similarity NPD5988 Approved
0.595 Remote Similarity NPD6370 Approved
0.5948 Remote Similarity NPD8133 Approved
0.5943 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5941 Remote Similarity NPD7521 Approved
0.5941 Remote Similarity NPD7146 Approved
0.5941 Remote Similarity NPD7334 Approved
0.5941 Remote Similarity NPD5330 Approved
0.5941 Remote Similarity NPD6684 Approved
0.5941 Remote Similarity NPD6409 Approved
0.592 Remote Similarity NPD7319 Approved
0.5917 Remote Similarity NPD6059 Approved
0.5913 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5909 Remote Similarity NPD7632 Discontinued
0.5909 Remote Similarity NPD5211 Phase 2
0.5902 Remote Similarity NPD7604 Phase 2
0.5888 Remote Similarity NPD7839 Suspended
0.5887 Remote Similarity NPD8293 Discontinued
0.5877 Remote Similarity NPD4061 Clinical (unspecified phase)
0.5872 Remote Similarity NPD6648 Approved
0.5872 Remote Similarity NPD5286 Approved
0.5872 Remote Similarity NPD4696 Approved
0.5872 Remote Similarity NPD5285 Approved
0.5865 Remote Similarity NPD5207 Approved
0.5859 Remote Similarity NPD3667 Approved
0.5859 Remote Similarity NPD5209 Approved
0.5847 Remote Similarity NPD6274 Approved
0.5843 Remote Similarity NPD7341 Phase 2
0.5842 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5841 Remote Similarity NPD6412 Phase 2
0.5833 Remote Similarity NPD4755 Approved
0.5833 Remote Similarity NPD7902 Approved
0.5825 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5825 Remote Similarity NPD5737 Approved
0.5825 Remote Similarity NPD6672 Approved
0.5818 Remote Similarity NPD5223 Approved
0.5818 Remote Similarity NPD1700 Approved
0.5814 Remote Similarity NPD3198 Approved
0.581 Remote Similarity NPD7637 Suspended
0.581 Remote Similarity NPD6079 Approved
0.5806 Remote Similarity NPD6336 Discontinued
0.5804 Remote Similarity NPD5141 Approved
0.5798 Remote Similarity NPD6317 Approved
0.5784 Remote Similarity NPD3618 Phase 1
0.5778 Remote Similarity NPD7331 Phase 2
0.5769 Remote Similarity NPD5328 Approved
0.5766 Remote Similarity NPD5225 Approved
0.5766 Remote Similarity NPD4633 Approved
0.5766 Remote Similarity NPD5226 Approved
0.5766 Remote Similarity NPD5224 Approved
0.576 Remote Similarity NPD8074 Phase 3
0.575 Remote Similarity NPD6314 Approved
0.575 Remote Similarity NPD6335 Approved
0.575 Remote Similarity NPD6313 Approved
0.5743 Remote Similarity NPD3666 Approved
0.5743 Remote Similarity NPD7338 Clinical (unspecified phase)
0.5743 Remote Similarity NPD3665 Phase 1
0.5743 Remote Similarity NPD3133 Approved
0.5743 Remote Similarity NPD4786 Approved
0.5741 Remote Similarity NPD5222 Approved
0.5741 Remote Similarity NPD4697 Phase 3
0.5741 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5741 Remote Similarity NPD5221 Approved
0.5727 Remote Similarity NPD4700 Approved
0.5714 Remote Similarity NPD5175 Approved
0.5714 Remote Similarity NPD5174 Approved
0.5702 Remote Similarity NPD7100 Approved
0.5702 Remote Similarity NPD7101 Approved
0.5702 Remote Similarity NPD5954 Clinical (unspecified phase)
0.5701 Remote Similarity NPD7748 Approved
0.5701 Remote Similarity NPD6001 Approved
0.57 Remote Similarity NPD4800 Clinical (unspecified phase)
0.569 Remote Similarity NPD4634 Approved
0.5688 Remote Similarity NPD5173 Approved
0.5667 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5664 Remote Similarity NPD4057 Clinical (unspecified phase)
0.5664 Remote Similarity NPD4056 Clinical (unspecified phase)
0.5648 Remote Similarity NPD5210 Approved
0.5648 Remote Similarity NPD4629 Approved
0.5645 Remote Similarity NPD7642 Approved
0.5644 Remote Similarity NPD6695 Phase 3

Structure

External Identifiers

PubChem CID   637093
ChEMBL   CHEMBL518687
ZINC  

Physicochemical Properties

Molecular Weight:  262.12
ALogP:  0.2123
MLogP:  2.67
XLogP:  0.489
# Rotatable Bonds:  2
Polar Surface Area:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  19

Download Data

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