Natural Product: NPC53158

Natural Product ID:  NPC53158
Common Name:   Lappalone
IUPAC Name:   (3R,3aR,6aR,9aR,9bR)-3-hydroxy-6,9-dimethylidene-3-(2-oxopropyl)-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-2-one
Synonyms:   Lappalone
Molecular Formula:   C17H22O4
Standard InCHIKey:  JPMPVNCPOBTSBR-CEEVZKBLSA-N
Standard InCHI:  InChI=1S/C17H22O4/c1-9-5-7-13-15(14-10(2)4-6-12(9)14)21-16(19)17(13,20)8-11(3)18/h12-15,20H,1-2,4-8H2,3H3/t12-,13+,14-,15-,17+/m0/s1
Canonical SMILES:  CC(=O)C[C@]1(O)C(=O)O[C@H]2[C@H]1CCC(=C)[C@H]1[C@@H]2C(=C)CC1
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
NPO30603 Saussurea lappa NA NA NA HerDing*
NPO25825 Saussurea costus Species Asteraceae Eukaryota TCMID*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT377 Cell Line OVCAR-3 Homo sapiens CD50 > 100 ug/ml 14510592
NPT165 Cell Line HeLa Homo sapiens CD50 > 100 ug/ml 14510592
NPT65 Cell Line HepG2 Homo sapiens CD50 > 100 ug/ml 14510592

  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 NPC53158 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
0.8667 High Similarity NPC475788
0.8571 High Similarity NPC51507
0.8478 Intermediate Similarity NPC475900
0.8387 Intermediate Similarity NPC476009
0.8352 Intermediate Similarity NPC469627
0.8298 Intermediate Similarity NPC474313
0.8242 Intermediate Similarity NPC65359
0.8132 Intermediate Similarity NPC12872
0.8132 Intermediate Similarity NPC168679
0.8111 Intermediate Similarity NPC201658
0.8111 Intermediate Similarity NPC190753
0.8085 Intermediate Similarity NPC163228
0.8065 Intermediate Similarity NPC473234
0.8065 Intermediate Similarity NPC473263
0.8065 Intermediate Similarity NPC60386
0.8065 Intermediate Similarity NPC308656
0.8065 Intermediate Similarity NPC473273
0.8061 Intermediate Similarity NPC475873
0.8041 Intermediate Similarity NPC474742
0.8 Intermediate Similarity NPC475491
0.8 Intermediate Similarity NPC238593
0.8 Intermediate Similarity NPC236692
0.8 Intermediate Similarity NPC309757
0.8 Intermediate Similarity NPC469626
0.7959 Intermediate Similarity NPC474747
0.7917 Intermediate Similarity NPC471150
0.7912 Intermediate Similarity NPC118601
0.7879 Intermediate Similarity NPC475945
0.7879 Intermediate Similarity NPC475871
0.7872 Intermediate Similarity NPC153590
0.7857 Intermediate Similarity NPC110443
0.7857 Intermediate Similarity NPC185141
0.7857 Intermediate Similarity NPC133907
0.7857 Intermediate Similarity NPC46998
0.7857 Intermediate Similarity NPC128733
0.7826 Intermediate Similarity NPC178875
0.7812 Intermediate Similarity NPC142529
0.7812 Intermediate Similarity NPC91771
0.7812 Intermediate Similarity NPC76862
0.7812 Intermediate Similarity NPC39859
0.7812 Intermediate Similarity NPC158416
0.7812 Intermediate Similarity NPC470883
0.7805 Intermediate Similarity NPC5714
0.78 Intermediate Similarity NPC474741
0.7789 Intermediate Similarity NPC473331
0.7766 Intermediate Similarity NPC184063
0.7755 Intermediate Similarity NPC186861
0.7745 Intermediate Similarity NPC117604
0.7742 Intermediate Similarity NPC173926
0.7742 Intermediate Similarity NPC474951
0.7732 Intermediate Similarity NPC213947
0.7732 Intermediate Similarity NPC170143
0.7732 Intermediate Similarity NPC108475
0.7732 Intermediate Similarity NPC311904
0.7727 Intermediate Similarity NPC258965
0.7727 Intermediate Similarity NPC156658
0.7723 Intermediate Similarity NPC44004
0.7684 Intermediate Similarity NPC200237
0.7684 Intermediate Similarity NPC469692
0.7684 Intermediate Similarity NPC469645
0.7667 Intermediate Similarity NPC54468
0.7667 Intermediate Similarity NPC111409
0.7667 Intermediate Similarity NPC128246
0.7667 Intermediate Similarity NPC245665
0.766 Intermediate Similarity NPC19087
0.7604 Intermediate Similarity NPC121825
0.7604 Intermediate Similarity NPC190294
0.7586 Intermediate Similarity NPC208223
0.7579 Intermediate Similarity NPC191339
0.7579 Intermediate Similarity NPC286341
0.7576 Intermediate Similarity NPC471381
0.757 Intermediate Similarity NPC54739
0.7558 Intermediate Similarity NPC179922
0.7553 Intermediate Similarity NPC38392
0.7528 Intermediate Similarity NPC293418
0.7528 Intermediate Similarity NPC290508
0.7528 Intermediate Similarity NPC73052
0.7528 Intermediate Similarity NPC6823
0.7527 Intermediate Similarity NPC186148
0.7527 Intermediate Similarity NPC179659
0.7526 Intermediate Similarity NPC476053
0.7526 Intermediate Similarity NPC472873
0.75 Intermediate Similarity NPC304624
0.75 Intermediate Similarity NPC171759
0.75 Intermediate Similarity NPC474053
0.75 Intermediate Similarity NPC47880
0.75 Intermediate Similarity NPC67296
0.7476 Intermediate Similarity NPC26617
0.7451 Intermediate Similarity NPC203659
0.7451 Intermediate Similarity NPC100487
0.7449 Intermediate Similarity NPC474297
0.7449 Intermediate Similarity NPC31645
0.7447 Intermediate Similarity NPC177629
0.7447 Intermediate Similarity NPC217983
0.7447 Intermediate Similarity NPC58219
0.7447 Intermediate Similarity NPC79549
0.7447 Intermediate Similarity NPC207114
0.7444 Intermediate Similarity NPC126248
0.7426 Intermediate Similarity NPC225353
0.7426 Intermediate Similarity NPC149371
0.7423 Intermediate Similarity NPC469632
0.7419 Intermediate Similarity NPC304558
0.7416 Intermediate Similarity NPC19841
0.7412 Intermediate Similarity NPC470243
0.7404 Intermediate Similarity NPC255082
0.7396 Intermediate Similarity NPC111114
0.7396 Intermediate Similarity NPC261607
0.7396 Intermediate Similarity NPC300312
0.7391 Intermediate Similarity NPC156485
0.7391 Intermediate Similarity NPC165287
0.7379 Intermediate Similarity NPC474101
0.7379 Intermediate Similarity NPC54737
0.7379 Intermediate Similarity NPC190867
0.7374 Intermediate Similarity NPC169205
0.7374 Intermediate Similarity NPC261372
0.7374 Intermediate Similarity NPC58267
0.7374 Intermediate Similarity NPC323421
0.7374 Intermediate Similarity NPC263674
0.7374 Intermediate Similarity NPC236580
0.7374 Intermediate Similarity NPC304445
0.7374 Intermediate Similarity NPC328562
0.7368 Intermediate Similarity NPC52198
0.7368 Intermediate Similarity NPC92974
0.7368 Intermediate Similarity NPC117405
0.7368 Intermediate Similarity NPC215556
0.7356 Intermediate Similarity NPC471491
0.7353 Intermediate Similarity NPC110989
0.7353 Intermediate Similarity NPC473148
0.7347 Intermediate Similarity NPC322188
0.7347 Intermediate Similarity NPC472469
0.7347 Intermediate Similarity NPC275960
0.7347 Intermediate Similarity NPC193645
0.7347 Intermediate Similarity NPC48803
0.7347 Intermediate Similarity NPC90121
0.734 Intermediate Similarity NPC197333
0.7339 Intermediate Similarity NPC471146
0.7339 Intermediate Similarity NPC471145
0.7333 Intermediate Similarity NPC103634
0.7327 Intermediate Similarity NPC472753
0.7327 Intermediate Similarity NPC477950
0.7327 Intermediate Similarity NPC201718
0.732 Intermediate Similarity NPC135776
0.7312 Intermediate Similarity NPC284534
0.7312 Intermediate Similarity NPC204105
0.7312 Intermediate Similarity NPC475206
0.7312 Intermediate Similarity NPC329749
0.7312 Intermediate Similarity NPC300082
0.7303 Intermediate Similarity NPC11796
0.7303 Intermediate Similarity NPC218817
0.73 Intermediate Similarity NPC45125
0.73 Intermediate Similarity NPC141191
0.7292 Intermediate Similarity NPC216284
0.7292 Intermediate Similarity NPC297474
0.7292 Intermediate Similarity NPC54065
0.7292 Intermediate Similarity NPC246173
0.7282 Intermediate Similarity NPC13385
0.7282 Intermediate Similarity NPC469629
0.7273 Intermediate Similarity NPC185553
0.7263 Intermediate Similarity NPC254572
0.7263 Intermediate Similarity NPC471047
0.7263 Intermediate Similarity NPC476708
0.7263 Intermediate Similarity NPC472008
0.7263 Intermediate Similarity NPC250687
0.7263 Intermediate Similarity NPC229407
0.7263 Intermediate Similarity NPC469628
0.7263 Intermediate Similarity NPC475906
0.7263 Intermediate Similarity NPC469653
0.7263 Intermediate Similarity NPC48824
0.7263 Intermediate Similarity NPC469631
0.7255 Intermediate Similarity NPC472754
0.7255 Intermediate Similarity NPC80144
0.7253 Intermediate Similarity NPC255580
0.7253 Intermediate Similarity NPC39411
0.7245 Intermediate Similarity NPC167219
0.7245 Intermediate Similarity NPC289004
0.7241 Intermediate Similarity NPC143979
0.7241 Intermediate Similarity NPC320537
0.7241 Intermediate Similarity NPC215030
0.7238 Intermediate Similarity NPC68248
0.7234 Intermediate Similarity NPC476015
0.7234 Intermediate Similarity NPC475019
0.7234 Intermediate Similarity NPC104961
0.7234 Intermediate Similarity NPC474949
0.7234 Intermediate Similarity NPC470242
0.7234 Intermediate Similarity NPC187661
0.7234 Intermediate Similarity NPC70555
0.7234 Intermediate Similarity NPC474762
0.7234 Intermediate Similarity NPC70422
0.7216 Intermediate Similarity NPC184463
0.7216 Intermediate Similarity NPC155215
0.7216 Intermediate Similarity NPC293001
0.7216 Intermediate Similarity NPC208886
0.7216 Intermediate Similarity NPC12172
0.7216 Intermediate Similarity NPC123177
0.7216 Intermediate Similarity NPC35959
0.7216 Intermediate Similarity NPC57304
0.7216 Intermediate Similarity NPC29821
0.7216 Intermediate Similarity NPC329952
0.7216 Intermediate Similarity NPC475925
0.7216 Intermediate Similarity NPC70595

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC53158 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
0.7476 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7347 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7253 Intermediate Similarity NPD5369 Approved
0.7234 Intermediate Similarity NPD5786 Approved
0.6989 Remote Similarity NPD6435 Approved
0.69 Remote Similarity NPD5282 Discontinued
0.6809 Remote Similarity NPD4269 Approved
0.6809 Remote Similarity NPD4270 Approved
0.6774 Remote Similarity NPD5368 Approved
0.67 Remote Similarity NPD7983 Approved
0.6667 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6667 Remote Similarity NPD6101 Approved
0.6636 Remote Similarity NPD6371 Approved
0.6634 Remote Similarity NPD6399 Phase 3
0.6632 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6598 Remote Similarity NPD5363 Approved
0.6596 Remote Similarity NPD4252 Approved
0.6562 Remote Similarity NPD5362 Discontinued
0.6545 Remote Similarity NPD6373 Approved
0.6545 Remote Similarity NPD6372 Approved
0.6535 Remote Similarity NPD6411 Approved
0.6505 Remote Similarity NPD5695 Phase 3
0.65 Remote Similarity NPD1695 Approved
0.6476 Remote Similarity NPD5696 Approved
0.6471 Remote Similarity NPD5778 Approved
0.6471 Remote Similarity NPD5779 Approved
0.6455 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6455 Remote Similarity NPD7320 Approved
0.6436 Remote Similarity NPD5785 Approved
0.6429 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6650 Approved
0.6429 Remote Similarity NPD6649 Approved
0.6422 Remote Similarity NPD6675 Approved
0.6422 Remote Similarity NPD6402 Approved
0.6422 Remote Similarity NPD5739 Approved
0.6422 Remote Similarity NPD7128 Approved
0.641 Remote Similarity NPD6319 Approved
0.6392 Remote Similarity NPD7154 Phase 3
0.6381 Remote Similarity NPD6083 Phase 2
0.6381 Remote Similarity NPD6084 Phase 2
0.6373 Remote Similarity NPD8034 Phase 2
0.6373 Remote Similarity NPD8035 Phase 2
0.6372 Remote Similarity NPD8297 Approved
0.6364 Remote Similarity NPD5697 Approved
0.6364 Remote Similarity NPD5701 Approved
0.6333 Remote Similarity NPD7492 Approved
0.633 Remote Similarity NPD4057 Clinical (unspecified phase)
0.633 Remote Similarity NPD4056 Clinical (unspecified phase)
0.6321 Remote Similarity NPD4225 Approved
0.6306 Remote Similarity NPD6899 Approved
0.6306 Remote Similarity NPD6881 Approved
0.6293 Remote Similarity NPD7115 Discovery
0.6281 Remote Similarity NPD6616 Approved
0.6271 Remote Similarity NPD6054 Approved
0.6271 Remote Similarity NPD6059 Approved
0.625 Remote Similarity NPD6012 Approved
0.625 Remote Similarity NPD4822 Approved
0.625 Remote Similarity NPD4820 Approved
0.625 Remote Similarity NPD4821 Approved
0.625 Remote Similarity NPD6014 Approved
0.625 Remote Similarity NPD5790 Clinical (unspecified phase)
0.625 Remote Similarity NPD4819 Approved
0.625 Remote Similarity NPD6013 Approved
0.623 Remote Similarity NPD7078 Approved
0.623 Remote Similarity NPD8293 Discontinued
0.6218 Remote Similarity NPD6015 Approved
0.6218 Remote Similarity NPD6016 Approved
0.6211 Remote Similarity NPD4802 Phase 2
0.6211 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6211 Remote Similarity NPD4238 Approved
0.6204 Remote Similarity NPD1700 Approved
0.62 Remote Similarity NPD4249 Approved
0.6195 Remote Similarity NPD6883 Approved
0.6195 Remote Similarity NPD7290 Approved
0.6195 Remote Similarity NPD7102 Approved
0.6179 Remote Similarity NPD7736 Approved
0.6174 Remote Similarity NPD4632 Approved
0.6167 Remote Similarity NPD5988 Approved
0.6167 Remote Similarity NPD6370 Approved
0.6161 Remote Similarity NPD6011 Approved
0.614 Remote Similarity NPD6847 Approved
0.614 Remote Similarity NPD8413 Clinical (unspecified phase)
0.614 Remote Similarity NPD8130 Phase 1
0.614 Remote Similarity NPD6617 Approved
0.614 Remote Similarity NPD6869 Approved
0.6139 Remote Similarity NPD4250 Approved
0.6139 Remote Similarity NPD4251 Approved
0.6132 Remote Similarity NPD4697 Phase 3
0.6126 Remote Similarity NPD6008 Approved
0.6117 Remote Similarity NPD6698 Approved
0.6117 Remote Similarity NPD46 Approved
0.61 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6087 Remote Similarity NPD6882 Approved
0.6087 Remote Similarity NPD6053 Discontinued
0.6078 Remote Similarity NPD6672 Approved
0.6078 Remote Similarity NPD5737 Approved
0.6075 Remote Similarity NPD4755 Approved
0.6061 Remote Similarity NPD5331 Approved
0.6061 Remote Similarity NPD5332 Approved
0.6053 Remote Similarity NPD4634 Approved
0.6042 Remote Similarity NPD4268 Approved
0.6042 Remote Similarity NPD4271 Approved
0.602 Remote Similarity NPD4790 Discontinued
0.6019 Remote Similarity NPD4753 Phase 2
0.6 Remote Similarity NPD6401 Clinical (unspecified phase)
0.5981 Remote Similarity NPD7839 Suspended
0.5963 Remote Similarity NPD4700 Approved
0.5963 Remote Similarity NPD5286 Approved
0.5963 Remote Similarity NPD4696 Approved
0.5963 Remote Similarity NPD5285 Approved
0.596 Remote Similarity NPD3667 Approved
0.5955 Remote Similarity NPD9496 Clinical (unspecified phase)
0.595 Remote Similarity NPD8516 Approved
0.595 Remote Similarity NPD6291 Clinical (unspecified phase)
0.595 Remote Similarity NPD8515 Approved
0.595 Remote Similarity NPD8517 Approved
0.595 Remote Similarity NPD8513 Phase 3
0.5941 Remote Similarity NPD7520 Clinical (unspecified phase)
0.5934 Remote Similarity NPD229 Approved
0.5932 Remote Similarity NPD6274 Approved
0.593 Remote Similarity NPD3198 Approved
0.5922 Remote Similarity NPD6903 Approved
0.5905 Remote Similarity NPD7637 Suspended
0.5888 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5888 Remote Similarity NPD4629 Approved
0.5888 Remote Similarity NPD5210 Approved
0.5882 Remote Similarity NPD6409 Approved
0.5882 Remote Similarity NPD5279 Phase 3
0.5882 Remote Similarity NPD6009 Approved
0.5882 Remote Similarity NPD8295 Clinical (unspecified phase)
0.5882 Remote Similarity NPD7334 Approved
0.5882 Remote Similarity NPD7521 Approved
0.5882 Remote Similarity NPD5330 Approved
0.5882 Remote Similarity NPD7146 Approved
0.5882 Remote Similarity NPD6098 Approved
0.5882 Remote Similarity NPD6684 Approved
0.5865 Remote Similarity NPD6904 Approved
0.5865 Remote Similarity NPD5370 Suspended
0.5865 Remote Similarity NPD6673 Approved
0.5865 Remote Similarity NPD6080 Approved
0.5862 Remote Similarity NPD2204 Approved
0.5856 Remote Similarity NPD5226 Approved
0.5856 Remote Similarity NPD5211 Phase 2
0.5856 Remote Similarity NPD4633 Approved
0.5856 Remote Similarity NPD5224 Approved
0.5856 Remote Similarity NPD5225 Approved
0.5854 Remote Similarity NPD8328 Phase 3
0.5843 Remote Similarity NPD7909 Approved
0.5843 Remote Similarity NPD3197 Phase 1
0.5842 Remote Similarity NPD4786 Approved
0.5833 Remote Similarity NPD5222 Approved
0.5833 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5833 Remote Similarity NPD5221 Approved
0.582 Remote Similarity NPD8266 Approved
0.582 Remote Similarity NPD8269 Approved
0.582 Remote Similarity NPD5983 Phase 2
0.582 Remote Similarity NPD8268 Approved
0.582 Remote Similarity NPD8274 Clinical (unspecified phase)
0.582 Remote Similarity NPD6921 Approved
0.582 Remote Similarity NPD8267 Approved
0.581 Remote Similarity NPD5207 Approved
0.581 Remote Similarity NPD5692 Phase 3
0.5804 Remote Similarity NPD5175 Approved
0.5804 Remote Similarity NPD5174 Approved
0.5794 Remote Similarity NPD6033 Approved
0.5789 Remote Similarity NPD6412 Phase 2
0.5785 Remote Similarity NPD7100 Approved
0.5785 Remote Similarity NPD7101 Approved
0.578 Remote Similarity NPD7902 Approved
0.578 Remote Similarity NPD5173 Approved
0.5778 Remote Similarity NPD7341 Phase 2
0.5772 Remote Similarity NPD8080 Discontinued
0.5769 Remote Similarity NPD7513 Clinical (unspecified phase)
0.5766 Remote Similarity NPD5223 Approved
0.5755 Remote Similarity NPD5693 Phase 1
0.5755 Remote Similarity NPD5694 Approved
0.5755 Remote Similarity NPD6050 Approved
0.5755 Remote Similarity NPD5281 Approved
0.5755 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5755 Remote Similarity NPD5284 Approved
0.5752 Remote Similarity NPD5141 Approved
0.575 Remote Similarity NPD6317 Approved
0.5748 Remote Similarity NPD7319 Approved
0.5743 Remote Similarity NPD4788 Approved
0.5729 Remote Similarity NPD3702 Approved
0.5728 Remote Similarity NPD3618 Phase 1
0.5728 Remote Similarity NPD6422 Discontinued
0.5728 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5726 Remote Similarity NPD7604 Phase 2
0.5714 Remote Similarity NPD8074 Phase 3
0.5714 Remote Similarity NPD5328 Approved
0.5714 Remote Similarity NPD7331 Phase 2
0.5714 Remote Similarity NPD3728 Approved
0.5714 Remote Similarity NPD3730 Approved
0.5702 Remote Similarity NPD6335 Approved
0.5702 Remote Similarity NPD6314 Approved
0.5702 Remote Similarity NPD4767 Approved
0.5702 Remote Similarity NPD4768 Approved
0.5702 Remote Similarity NPD6313 Approved
0.5691 Remote Similarity NPD6909 Approved

Structure

External Identifiers

PubChem CID   10979139
ChEMBL   CHEMBL518009
ZINC  

Physicochemical Properties

Molecular Weight:  290.15
ALogP:  0.1793
MLogP:  2.89
XLogP:  1.926
# Rotatable Bonds:  4
Polar Surface Area:  63.6
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  21

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs