Natural Product: NPC115021

Natural Product ID:  NPC115021
Common Name:   12(S)-Hydroxycleroda-3,13-Dien-16,15-Olide
IUPAC Name:   4-[(1S)-2-[(1S,2R,4aR,8aR)-1,2,4a,5-tetramethyl-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-1-hydroxyethyl]-2H-furan-5-one
Synonyms:  
Molecular Formula:   C20H30O3
Standard InCHIKey:  KWTXYVRTXYEKJE-GVJFSJSTSA-N
Standard InCHI:  InChI=1S/C20H30O3/c1-13-6-5-7-17-19(13,3)10-8-14(2)20(17,4)12-16(21)15-9-11-23-18(15)22/h6,9,14,16-17,21H,5,7-8,10-12H2,1-4H3/t14-,16+,17+,19+,20+/m1/s1
Canonical SMILES:  O=C1OCC=C1[C@H](C[C@@]1(C)[C@H](C)CC[C@@]2([C@@H]1CCC=C2C)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
NPO24855 Callicarpa americana Species Lamiaceae Eukaryota fruiting branches PMID[17279798]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT83 Cell Line MCF7 Homo sapiens ED50 = 2.8 ug/ml 22472691
NPT858 Cell Line LNCaP Homo sapiens ED50 = 3.3 ug/ml 16038541
NPT1034 Cell Line Lu1 Homo sapiens ED50 = 2.9 ug/ml 22342628

  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 NPC115021 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
0.9655 High Similarity NPC472814
0.9655 High Similarity NPC177037
0.9231 High Similarity NPC242848
0.9205 High Similarity NPC5509
0.9195 High Similarity NPC312561
0.914 High Similarity NPC474012
0.914 High Similarity NPC476299
0.913 High Similarity NPC475709
0.9101 High Similarity NPC51486
0.8989 High Similarity NPC174342
0.8966 High Similarity NPC86316
0.8966 High Similarity NPC106416
0.8925 High Similarity NPC53844
0.8901 High Similarity NPC139692
0.8889 High Similarity NPC232426
0.8889 High Similarity NPC281942
0.8817 High Similarity NPC234993
0.8817 High Similarity NPC17578
0.8817 High Similarity NPC240673
0.8817 High Similarity NPC134072
0.8804 High Similarity NPC474555
0.8804 High Similarity NPC53685
0.8791 High Similarity NPC141831
0.875 High Similarity NPC65661
0.875 High Similarity NPC189311
0.8736 High Similarity NPC311070
0.871 High Similarity NPC209355
0.8667 High Similarity NPC226863
0.8652 High Similarity NPC194417
0.8632 High Similarity NPC316598
0.8602 High Similarity NPC474554
0.8587 High Similarity NPC477783
0.8586 High Similarity NPC91034
0.8571 High Similarity NPC251528
0.8571 High Similarity NPC470734
0.8571 High Similarity NPC168131
0.8556 High Similarity NPC171722
0.8542 High Similarity NPC117685
0.8542 High Similarity NPC54705
0.8526 High Similarity NPC208094
0.8523 High Similarity NPC193198
0.8511 High Similarity NPC183012
0.8506 High Similarity NPC282293
0.85 High Similarity NPC220155
0.8478 Intermediate Similarity NPC477782
0.8478 Intermediate Similarity NPC8062
0.8469 Intermediate Similarity NPC476889
0.8454 Intermediate Similarity NPC469657
0.8454 Intermediate Similarity NPC244456
0.8454 Intermediate Similarity NPC471075
0.8444 Intermediate Similarity NPC474062
0.8438 Intermediate Similarity NPC23364
0.8427 Intermediate Similarity NPC30486
0.8421 Intermediate Similarity NPC476797
0.8421 Intermediate Similarity NPC202833
0.8409 Intermediate Similarity NPC200513
0.8404 Intermediate Similarity NPC470697
0.8391 Intermediate Similarity NPC271104
0.8387 Intermediate Similarity NPC233345
0.8387 Intermediate Similarity NPC303697
0.8387 Intermediate Similarity NPC186363
0.8384 Intermediate Similarity NPC146731
0.8384 Intermediate Similarity NPC296950
0.837 Intermediate Similarity NPC50488
0.837 Intermediate Similarity NPC474396
0.8367 Intermediate Similarity NPC476890
0.8367 Intermediate Similarity NPC40918
0.8351 Intermediate Similarity NPC174314
0.8351 Intermediate Similarity NPC201406
0.8333 Intermediate Similarity NPC42586
0.8333 Intermediate Similarity NPC474343
0.8333 Intermediate Similarity NPC473251
0.8333 Intermediate Similarity NPC29133
0.8333 Intermediate Similarity NPC253826
0.8333 Intermediate Similarity NPC52628
0.8316 Intermediate Similarity NPC295347
0.8315 Intermediate Similarity NPC42476
0.8315 Intermediate Similarity NPC22611
0.8315 Intermediate Similarity NPC472377
0.83 Intermediate Similarity NPC1679
0.8298 Intermediate Similarity NPC166346
0.8298 Intermediate Similarity NPC472303
0.8298 Intermediate Similarity NPC475657
0.8283 Intermediate Similarity NPC112009
0.8283 Intermediate Similarity NPC159533
0.828 Intermediate Similarity NPC182136
0.828 Intermediate Similarity NPC78973
0.8276 Intermediate Similarity NPC242767
0.8276 Intermediate Similarity NPC150646
0.8265 Intermediate Similarity NPC471412
0.8265 Intermediate Similarity NPC93744
0.8265 Intermediate Similarity NPC476888
0.8261 Intermediate Similarity NPC472809
0.8261 Intermediate Similarity NPC472810
0.8261 Intermediate Similarity NPC104560
0.8261 Intermediate Similarity NPC24816
0.8256 Intermediate Similarity NPC316500
0.8252 Intermediate Similarity NPC474315
0.8252 Intermediate Similarity NPC470961
0.8247 Intermediate Similarity NPC124512
0.8247 Intermediate Similarity NPC159763
0.8247 Intermediate Similarity NPC278386
0.8242 Intermediate Similarity NPC131813
0.8229 Intermediate Similarity NPC184065
0.8229 Intermediate Similarity NPC29952
0.8222 Intermediate Similarity NPC165064
0.8222 Intermediate Similarity NPC31086
0.8211 Intermediate Similarity NPC84893
0.8211 Intermediate Similarity NPC104925
0.8211 Intermediate Similarity NPC298973
0.8191 Intermediate Similarity NPC289479
0.8191 Intermediate Similarity NPC252433
0.8191 Intermediate Similarity NPC72845
0.8182 Intermediate Similarity NPC476081
0.8173 Intermediate Similarity NPC191620
0.8172 Intermediate Similarity NPC79027
0.8163 Intermediate Similarity NPC471413
0.8163 Intermediate Similarity NPC472644
0.8163 Intermediate Similarity NPC476767
0.8163 Intermediate Similarity NPC476274
0.8155 Intermediate Similarity NPC235014
0.8144 Intermediate Similarity NPC287668
0.8144 Intermediate Similarity NPC476253
0.8144 Intermediate Similarity NPC156546
0.8144 Intermediate Similarity NPC73911
0.8137 Intermediate Similarity NPC476765
0.8132 Intermediate Similarity NPC471795
0.8132 Intermediate Similarity NPC474853
0.8132 Intermediate Similarity NPC179006
0.8125 Intermediate Similarity NPC293052
0.8111 Intermediate Similarity NPC97913
0.8105 Intermediate Similarity NPC152778
0.8105 Intermediate Similarity NPC271652
0.8105 Intermediate Similarity NPC162615
0.8105 Intermediate Similarity NPC472871
0.8105 Intermediate Similarity NPC205034
0.81 Intermediate Similarity NPC329345
0.81 Intermediate Similarity NPC475526
0.81 Intermediate Similarity NPC180204
0.81 Intermediate Similarity NPC95899
0.81 Intermediate Similarity NPC120321
0.81 Intermediate Similarity NPC473283
0.81 Intermediate Similarity NPC72151
0.8095 Intermediate Similarity NPC122056
0.809 Intermediate Similarity NPC325031
0.809 Intermediate Similarity NPC40228
0.809 Intermediate Similarity NPC14203
0.809 Intermediate Similarity NPC229584
0.8085 Intermediate Similarity NPC15059
0.8085 Intermediate Similarity NPC477149
0.8085 Intermediate Similarity NPC477147
0.8085 Intermediate Similarity NPC472307
0.8085 Intermediate Similarity NPC158488
0.8085 Intermediate Similarity NPC310479
0.8085 Intermediate Similarity NPC220454
0.8085 Intermediate Similarity NPC469595
0.8085 Intermediate Similarity NPC280149
0.8085 Intermediate Similarity NPC221111
0.8085 Intermediate Similarity NPC212679
0.8081 Intermediate Similarity NPC472924
0.8081 Intermediate Similarity NPC282524
0.8081 Intermediate Similarity NPC303559
0.8081 Intermediate Similarity NPC224720
0.8081 Intermediate Similarity NPC472643
0.8081 Intermediate Similarity NPC476240
0.8081 Intermediate Similarity NPC476223
0.8077 Intermediate Similarity NPC324683
0.8068 Intermediate Similarity NPC308038
0.8065 Intermediate Similarity NPC472870
0.8065 Intermediate Similarity NPC472378
0.8065 Intermediate Similarity NPC277771
0.8065 Intermediate Similarity NPC249889
0.8065 Intermediate Similarity NPC472302
0.8065 Intermediate Similarity NPC215831
0.8065 Intermediate Similarity NPC193843
0.8065 Intermediate Similarity NPC72397
0.8061 Intermediate Similarity NPC222303
0.8061 Intermediate Similarity NPC216478
0.8061 Intermediate Similarity NPC478056
0.8061 Intermediate Similarity NPC98868
0.8061 Intermediate Similarity NPC108368
0.8061 Intermediate Similarity NPC57079
0.8058 Intermediate Similarity NPC137911
0.8058 Intermediate Similarity NPC228477
0.8046 Intermediate Similarity NPC97377
0.8043 Intermediate Similarity NPC261721
0.8043 Intermediate Similarity NPC82979
0.8043 Intermediate Similarity NPC220478
0.8043 Intermediate Similarity NPC473226
0.8043 Intermediate Similarity NPC329692
0.8043 Intermediate Similarity NPC471219
0.8043 Intermediate Similarity NPC198761
0.8043 Intermediate Similarity NPC322159
0.8041 Intermediate Similarity NPC456
0.8041 Intermediate Similarity NPC154526
0.8041 Intermediate Similarity NPC29152
0.8041 Intermediate Similarity NPC470801
0.8041 Intermediate Similarity NPC472362
0.8041 Intermediate Similarity NPC472363
0.8041 Intermediate Similarity NPC472941

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC115021 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
0.8409 Intermediate Similarity NPD4752 Clinical (unspecified phase)
0.8247 Intermediate Similarity NPD4225 Approved
0.7935 Intermediate Similarity NPD1694 Approved
0.787 Intermediate Similarity NPD7115 Discovery
0.78 Intermediate Similarity NPD7640 Approved
0.78 Intermediate Similarity NPD7639 Approved
0.7788 Intermediate Similarity NPD6686 Approved
0.7708 Intermediate Similarity NPD5785 Approved
0.77 Intermediate Similarity NPD7638 Approved
0.766 Intermediate Similarity NPD7334 Approved
0.766 Intermediate Similarity NPD6409 Approved
0.766 Intermediate Similarity NPD5330 Approved
0.766 Intermediate Similarity NPD7146 Approved
0.766 Intermediate Similarity NPD6684 Approved
0.766 Intermediate Similarity NPD7521 Approved
0.7634 Intermediate Similarity NPD3665 Phase 1
0.7634 Intermediate Similarity NPD3133 Approved
0.7634 Intermediate Similarity NPD3666 Approved
0.76 Intermediate Similarity NPD6083 Phase 2
0.76 Intermediate Similarity NPD6084 Phase 2
0.7576 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD5695 Phase 3
0.7551 Intermediate Similarity NPD5779 Approved
0.7551 Intermediate Similarity NPD5778 Approved
0.75 Intermediate Similarity NPD6903 Approved
0.75 Intermediate Similarity NPD7513 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD7748 Approved
0.7474 Intermediate Similarity NPD3618 Phase 1
0.7449 Intermediate Similarity NPD7515 Phase 2
0.7449 Intermediate Similarity NPD6411 Approved
0.7447 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7419 Intermediate Similarity NPD3667 Approved
0.7383 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7374 Intermediate Similarity NPD6399 Phase 3
0.7358 Intermediate Similarity NPD5697 Approved
0.7353 Intermediate Similarity NPD5696 Approved
0.732 Intermediate Similarity NPD6672 Approved
0.732 Intermediate Similarity NPD5737 Approved
0.7292 Intermediate Similarity NPD4623 Approved
0.7292 Intermediate Similarity NPD4519 Discontinued
0.7292 Intermediate Similarity NPD5279 Phase 3
0.729 Intermediate Similarity NPD6881 Approved
0.729 Intermediate Similarity NPD6899 Approved
0.7273 Intermediate Similarity NPD6079 Approved
0.7273 Intermediate Similarity NPD5693 Phase 1
0.7273 Intermediate Similarity NPD7637 Suspended
0.7264 Intermediate Similarity NPD7128 Approved
0.7264 Intermediate Similarity NPD6675 Approved
0.7264 Intermediate Similarity NPD6402 Approved
0.7264 Intermediate Similarity NPD5739 Approved
0.7263 Intermediate Similarity NPD4786 Approved
0.7255 Intermediate Similarity NPD7902 Approved
0.7245 Intermediate Similarity NPD5328 Approved
0.7245 Intermediate Similarity NPD6101 Approved
0.7245 Intermediate Similarity NPD4753 Phase 2
0.7245 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD6012 Approved
0.7222 Intermediate Similarity NPD6014 Approved
0.7222 Intermediate Similarity NPD6013 Approved
0.7196 Intermediate Similarity NPD5701 Approved
0.7188 Intermediate Similarity NPD5363 Approved
0.7156 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7156 Intermediate Similarity NPD6371 Approved
0.7156 Intermediate Similarity NPD7290 Approved
0.7156 Intermediate Similarity NPD6883 Approved
0.7156 Intermediate Similarity NPD7102 Approved
0.7143 Intermediate Similarity NPD5211 Phase 2
0.7143 Intermediate Similarity NPD7632 Discontinued
0.713 Intermediate Similarity NPD7320 Approved
0.713 Intermediate Similarity NPD6011 Approved
0.7113 Intermediate Similarity NPD3574 Clinical (unspecified phase)
0.7091 Intermediate Similarity NPD6650 Approved
0.7091 Intermediate Similarity NPD6847 Approved
0.7091 Intermediate Similarity NPD6869 Approved
0.7091 Intermediate Similarity NPD8130 Phase 1
0.7091 Intermediate Similarity NPD6649 Approved
0.7091 Intermediate Similarity NPD6617 Approved
0.7064 Intermediate Similarity NPD6372 Approved
0.7064 Intermediate Similarity NPD6373 Approved
0.7059 Intermediate Similarity NPD5210 Approved
0.7059 Intermediate Similarity NPD4629 Approved
0.7053 Intermediate Similarity NPD4221 Approved
0.7053 Intermediate Similarity NPD5209 Approved
0.7053 Intermediate Similarity NPD4223 Phase 3
0.7041 Intermediate Similarity NPD3573 Approved
0.7033 Intermediate Similarity NPD8039 Approved
0.703 Intermediate Similarity NPD4202 Approved
0.7027 Intermediate Similarity NPD6053 Discontinued
0.7027 Intermediate Similarity NPD8297 Approved
0.7027 Intermediate Similarity NPD6882 Approved
0.7021 Intermediate Similarity NPD4695 Discontinued
0.7009 Intermediate Similarity NPD5141 Approved
0.7 Intermediate Similarity NPD6698 Approved
0.7 Intermediate Similarity NPD46 Approved
0.699 Remote Similarity NPD5220 Clinical (unspecified phase)
0.699 Remote Similarity NPD5221 Approved
0.699 Remote Similarity NPD5222 Approved
0.6989 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6979 Remote Similarity NPD7154 Phase 3
0.697 Remote Similarity NPD5208 Approved
0.6961 Remote Similarity NPD7900 Approved
0.6961 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6952 Remote Similarity NPD6404 Discontinued
0.6952 Remote Similarity NPD4696 Approved
0.6952 Remote Similarity NPD5285 Approved
0.6952 Remote Similarity NPD5286 Approved
0.6939 Remote Similarity NPD5690 Phase 2
0.6931 Remote Similarity NPD5281 Approved
0.6931 Remote Similarity NPD5284 Approved
0.6923 Remote Similarity NPD4755 Approved
0.6923 Remote Similarity NPD5173 Approved
0.6907 Remote Similarity NPD4197 Approved
0.69 Remote Similarity NPD6051 Approved
0.69 Remote Similarity NPD6673 Approved
0.69 Remote Similarity NPD6080 Approved
0.69 Remote Similarity NPD6904 Approved
0.6897 Remote Similarity NPD6319 Approved
0.6881 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6881 Remote Similarity NPD6412 Phase 2
0.6875 Remote Similarity NPD4269 Approved
0.6875 Remote Similarity NPD4270 Approved
0.686 Remote Similarity NPD7319 Approved
0.6842 Remote Similarity NPD6274 Approved
0.6837 Remote Similarity NPD5329 Approved
0.6837 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6832 Remote Similarity NPD5207 Approved
0.6832 Remote Similarity NPD5692 Phase 3
0.6827 Remote Similarity NPD4697 Phase 3
0.6822 Remote Similarity NPD5225 Approved
0.6822 Remote Similarity NPD5224 Approved
0.6822 Remote Similarity NPD4633 Approved
0.6822 Remote Similarity NPD5226 Approved
0.6809 Remote Similarity NPD3617 Approved
0.6804 Remote Similarity NPD5362 Discontinued
0.6792 Remote Similarity NPD4700 Approved
0.6786 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6768 Remote Similarity NPD5786 Approved
0.6768 Remote Similarity NPD5280 Approved
0.6768 Remote Similarity NPD4690 Approved
0.6768 Remote Similarity NPD4694 Approved
0.6768 Remote Similarity NPD4689 Approved
0.6768 Remote Similarity NPD5205 Approved
0.6768 Remote Similarity NPD4138 Approved
0.6768 Remote Similarity NPD4693 Phase 3
0.6768 Remote Similarity NPD4688 Approved
0.6768 Remote Similarity NPD6098 Approved
0.6765 Remote Similarity NPD6050 Approved
0.6765 Remote Similarity NPD5694 Approved
0.6759 Remote Similarity NPD5174 Approved
0.6759 Remote Similarity NPD5175 Approved
0.675 Remote Similarity NPD7507 Approved
0.6735 Remote Similarity NPD3668 Phase 3
0.6733 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6731 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6729 Remote Similarity NPD5223 Approved
0.6727 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6696 Remote Similarity NPD4634 Approved
0.6696 Remote Similarity NPD6868 Approved
0.6667 Remote Similarity NPD7492 Approved
0.6667 Remote Similarity NPD7100 Approved
0.6667 Remote Similarity NPD4252 Approved
0.6667 Remote Similarity NPD1696 Phase 3
0.6667 Remote Similarity NPD7101 Approved
0.6667 Remote Similarity NPD4632 Approved
0.6667 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6638 Remote Similarity NPD6317 Approved
0.6635 Remote Similarity NPD5282 Discontinued
0.6635 Remote Similarity NPD6001 Approved
0.6633 Remote Similarity NPD4788 Approved
0.6612 Remote Similarity NPD6616 Approved
0.661 Remote Similarity NPD6054 Approved
0.6602 Remote Similarity NPD8035 Phase 2
0.6602 Remote Similarity NPD8034 Phase 2
0.6602 Remote Similarity NPD7983 Approved
0.6598 Remote Similarity NPD5369 Approved
0.6596 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6593 Remote Similarity NPD4691 Approved
0.6581 Remote Similarity NPD6314 Approved
0.6581 Remote Similarity NPD6335 Approved
0.6581 Remote Similarity NPD6313 Approved
0.6574 Remote Similarity NPD5344 Discontinued
0.6562 Remote Similarity NPD7645 Phase 2
0.6562 Remote Similarity NPD4195 Approved
0.6557 Remote Similarity NPD7078 Approved
0.6555 Remote Similarity NPD6015 Approved
0.6555 Remote Similarity NPD6016 Approved
0.6531 Remote Similarity NPD6435 Approved
0.6518 Remote Similarity NPD4729 Approved
0.6518 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6518 Remote Similarity NPD4730 Approved
0.6518 Remote Similarity NPD5128 Approved
0.6509 Remote Similarity NPD7839 Suspended
0.6509 Remote Similarity NPD7614 Phase 1
0.6505 Remote Similarity NPD7838 Discovery
0.6504 Remote Similarity NPD7736 Approved
0.65 Remote Similarity NPD6082 Clinical (unspecified phase)
0.65 Remote Similarity NPD5988 Approved
0.65 Remote Similarity NPD6370 Approved
0.6496 Remote Similarity NPD6009 Approved
0.6495 Remote Similarity NPD4820 Approved

Structure

External Identifiers

PubChem CID   16115036
ChEMBL   CHEMBL387361
ZINC  

Physicochemical Properties

Molecular Weight:  318.22
ALogP:  2.0347
MLogP:  3.33
XLogP:  6.091
# Rotatable Bonds:  8
Polar Surface Area:  46.53
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  23

Download Data

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Structure MOL file  
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Biological Activities  
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