Natural Product: NPC52198

Natural Product ID:  NPC52198
Common Name:   Plenolin
IUPAC Name:   (1S,3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-1,5,8a-trimethyl-3a,4,5,5a,9,9a-hexahydro-1H-azuleno[6,7-b]furan-2,8-dione
Synonyms:   11,13-Dihyrdrohelenalin; 11Alpha,13-Dihydrohelenalin
Molecular Formula:   C15H20O4
Standard InCHIKey:  ICKWITMQEROMDG-ZIXXKTFOSA-N
Standard InCHI:  InChI=1S/C15H20O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7-10,12-13,17H,6H2,1-3H3/t7-,8+,9+,10-,12-,13+,15+/m1/s1
Canonical SMILES:  C[C@@H]1C(=O)O[C@H]2[C@@H]1[C@H](O)[C@]1(C)C(=O)C=C[C@H]1[C@@H](C2)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
NPO27384 Eclipta latifolia Species Cerambycidae Eukaryota UNPD*
NPO29642 Centipedae herba NA NA NA TCMSP*
NPO27548 Heterodera glycines Species Heteroderidae Eukaryota UNPD*
NPO10747 Streptomyces sp. sn-593 Species Streptomycetaceae Bacteria UNPD*
NPO10811 Baileya pleniradiata Species Asteraceae Eukaryota TCM_Taiwan*
NPO26233 Helenium autumnale Species Asteraceae Eukaryota TCM_Taiwan*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT983 Protein Complex Nuclear factor NF-kappa-B complex Homo sapiens IC100 = 0.2 nM 15537359
NPT721 Individual Protein Nuclear factor NF-kappa-B p65 subunit Homo sapiens IC100 = 0.2 nM 16570920
NPT2 Others Unspecified IC50 = 128000 nM 9090867
NPT2 Others Unspecified IC50 = 6500 nM 9090867
NPT65 Cell Line HepG2 Homo sapiens ED50 = 0.8 ug/ml 20187635
NPT2 Others Unspecified ED50 = 0.81 ug/ml 671468
NPT1490 Cell Line Ehrlich Mus musculus TGI = 100 % 845864
NPT2 Others Unspecified ED50 = 0.814 ug/ml 845864

  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 NPC52198 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 NPC117405
0.9432 High Similarity NPC48803
0.9432 High Similarity NPC90121
0.9432 High Similarity NPC275960
0.9432 High Similarity NPC193645
0.9405 High Similarity NPC70555
0.9405 High Similarity NPC70422
0.9405 High Similarity NPC104961
0.9326 High Similarity NPC185553
0.9318 High Similarity NPC289004
0.9222 High Similarity NPC169205
0.9121 High Similarity NPC141191
0.8977 High Similarity NPC253144
0.8876 High Similarity NPC284185
0.8876 High Similarity NPC74103
0.8876 High Similarity NPC150978
0.8876 High Similarity NPC123177
0.8876 High Similarity NPC70595
0.883 High Similarity NPC225353
0.8737 High Similarity NPC110989
0.8681 High Similarity NPC167219
0.8646 High Similarity NPC203659
0.8506 High Similarity NPC165287
0.8462 Intermediate Similarity NPC300312
0.8462 Intermediate Similarity NPC111114
0.8462 Intermediate Similarity NPC261607
0.8444 Intermediate Similarity NPC168679
0.8444 Intermediate Similarity NPC12872
0.8409 Intermediate Similarity NPC161957
0.8409 Intermediate Similarity NPC21471
0.8409 Intermediate Similarity NPC33570
0.8316 Intermediate Similarity NPC54843
0.8222 Intermediate Similarity NPC237540
0.8202 Intermediate Similarity NPC125290
0.8182 Intermediate Similarity NPC39588
0.8152 Intermediate Similarity NPC129419
0.8144 Intermediate Similarity NPC171759
0.8144 Intermediate Similarity NPC477950
0.8061 Intermediate Similarity NPC474747
0.8046 Intermediate Similarity NPC51507
0.8043 Intermediate Similarity NPC268298
0.8 Intermediate Similarity NPC304886
0.798 Intermediate Similarity NPC475871
0.798 Intermediate Similarity NPC475945
0.7979 Intermediate Similarity NPC135776
0.7978 Intermediate Similarity NPC215294
0.7955 Intermediate Similarity NPC39411
0.7955 Intermediate Similarity NPC255580
0.7955 Intermediate Similarity NPC470241
0.7917 Intermediate Similarity NPC91771
0.7917 Intermediate Similarity NPC126156
0.7917 Intermediate Similarity NPC142529
0.7912 Intermediate Similarity NPC238593
0.7912 Intermediate Similarity NPC309757
0.7912 Intermediate Similarity NPC236692
0.7882 Intermediate Similarity NPC179922
0.7872 Intermediate Similarity NPC131209
0.7841 Intermediate Similarity NPC223904
0.7835 Intermediate Similarity NPC108475
0.7835 Intermediate Similarity NPC170143
0.7835 Intermediate Similarity NPC213947
0.7826 Intermediate Similarity NPC201658
0.7802 Intermediate Similarity NPC165162
0.7789 Intermediate Similarity NPC200237
0.7789 Intermediate Similarity NPC153590
0.7778 Intermediate Similarity NPC474742
0.7766 Intermediate Similarity NPC71533
0.7766 Intermediate Similarity NPC106510
0.7765 Intermediate Similarity NPC472966
0.7732 Intermediate Similarity NPC184065
0.7727 Intermediate Similarity NPC113363
0.7723 Intermediate Similarity NPC474741
0.7723 Intermediate Similarity NPC100487
0.7723 Intermediate Similarity NPC309190
0.7717 Intermediate Similarity NPC107787
0.7708 Intermediate Similarity NPC477131
0.7708 Intermediate Similarity NPC469632
0.7708 Intermediate Similarity NPC473331
0.7701 Intermediate Similarity NPC195785
0.7701 Intermediate Similarity NPC15975
0.7692 Intermediate Similarity NPC115786
0.7692 Intermediate Similarity NPC472958
0.7692 Intermediate Similarity NPC472957
0.7684 Intermediate Similarity NPC133698
0.7667 Intermediate Similarity NPC89555
0.766 Intermediate Similarity NPC32922
0.7653 Intermediate Similarity NPC477949
0.7647 Intermediate Similarity NPC472956
0.7647 Intermediate Similarity NPC291643
0.7642 Intermediate Similarity NPC209058
0.764 Intermediate Similarity NPC74673
0.764 Intermediate Similarity NPC69271
0.7624 Intermediate Similarity NPC475873
0.7614 Intermediate Similarity NPC218817
0.7614 Intermediate Similarity NPC192006
0.7614 Intermediate Similarity NPC11796
0.7609 Intermediate Similarity NPC78089
0.7609 Intermediate Similarity NPC28887
0.7604 Intermediate Similarity NPC473234
0.7604 Intermediate Similarity NPC473273
0.7604 Intermediate Similarity NPC475302
0.7604 Intermediate Similarity NPC60386
0.7604 Intermediate Similarity NPC473263
0.7604 Intermediate Similarity NPC308656
0.76 Intermediate Similarity NPC133907
0.76 Intermediate Similarity NPC128733
0.76 Intermediate Similarity NPC185141
0.76 Intermediate Similarity NPC110443
0.76 Intermediate Similarity NPC46998
0.76 Intermediate Similarity NPC472753
0.7586 Intermediate Similarity NPC472967
0.7586 Intermediate Similarity NPC472959
0.7586 Intermediate Similarity NPC266159
0.7582 Intermediate Similarity NPC1761
0.7582 Intermediate Similarity NPC52609
0.7582 Intermediate Similarity NPC54468
0.7579 Intermediate Similarity NPC145666
0.7579 Intermediate Similarity NPC62815
0.7579 Intermediate Similarity NPC77337
0.7579 Intermediate Similarity NPC469368
0.7556 Intermediate Similarity NPC10276
0.7556 Intermediate Similarity NPC35089
0.7553 Intermediate Similarity NPC476706
0.7553 Intermediate Similarity NPC476707
0.7553 Intermediate Similarity NPC476805
0.7551 Intermediate Similarity NPC18019
0.7551 Intermediate Similarity NPC24956
0.7528 Intermediate Similarity NPC470244
0.7528 Intermediate Similarity NPC164308
0.7528 Intermediate Similarity NPC470239
0.7527 Intermediate Similarity NPC150755
0.7527 Intermediate Similarity NPC305475
0.7527 Intermediate Similarity NPC475461
0.7526 Intermediate Similarity NPC323008
0.7526 Intermediate Similarity NPC262133
0.7526 Intermediate Similarity NPC470013
0.7526 Intermediate Similarity NPC470010
0.7526 Intermediate Similarity NPC198853
0.7525 Intermediate Similarity NPC472754
0.75 Intermediate Similarity NPC306856
0.75 Intermediate Similarity NPC191339
0.75 Intermediate Similarity NPC475960
0.75 Intermediate Similarity NPC114979
0.75 Intermediate Similarity NPC286341
0.75 Intermediate Similarity NPC191476
0.75 Intermediate Similarity NPC141193
0.75 Intermediate Similarity NPC96259
0.75 Intermediate Similarity NPC252433
0.7476 Intermediate Similarity NPC243998
0.7475 Intermediate Similarity NPC311904
0.7475 Intermediate Similarity NPC70145
0.7475 Intermediate Similarity NPC91695
0.7475 Intermediate Similarity NPC87090
0.7475 Intermediate Similarity NPC474343
0.7474 Intermediate Similarity NPC295312
0.7474 Intermediate Similarity NPC155935
0.7451 Intermediate Similarity NPC472755
0.7447 Intermediate Similarity NPC118601
0.7447 Intermediate Similarity NPC72513
0.7444 Intermediate Similarity NPC276356
0.7444 Intermediate Similarity NPC293418
0.7444 Intermediate Similarity NPC73052
0.7444 Intermediate Similarity NPC290508
0.7444 Intermediate Similarity NPC302426
0.7444 Intermediate Similarity NPC6823
0.7429 Intermediate Similarity NPC47951
0.7426 Intermediate Similarity NPC244456
0.7426 Intermediate Similarity NPC47880
0.7426 Intermediate Similarity NPC476223
0.7426 Intermediate Similarity NPC476240
0.7426 Intermediate Similarity NPC469657
0.7426 Intermediate Similarity NPC224720
0.7426 Intermediate Similarity NPC477356
0.7423 Intermediate Similarity NPC469692
0.7423 Intermediate Similarity NPC469645
0.7423 Intermediate Similarity NPC109414
0.7419 Intermediate Similarity NPC476628
0.7419 Intermediate Similarity NPC475206
0.7419 Intermediate Similarity NPC261380
0.7419 Intermediate Similarity NPC255307
0.7419 Intermediate Similarity NPC470755
0.74 Intermediate Similarity NPC477355
0.7396 Intermediate Similarity NPC19087
0.7396 Intermediate Similarity NPC51486
0.7396 Intermediate Similarity NPC35809
0.7396 Intermediate Similarity NPC473455
0.7396 Intermediate Similarity NPC54065
0.7396 Intermediate Similarity NPC297474
0.7386 Intermediate Similarity NPC266119
0.7383 Intermediate Similarity NPC76550
0.7383 Intermediate Similarity NPC138757
0.7383 Intermediate Similarity NPC123855
0.7381 Intermediate Similarity NPC476614
0.7379 Intermediate Similarity NPC255309
0.7379 Intermediate Similarity NPC472756
0.7374 Intermediate Similarity NPC476009
0.7368 Intermediate Similarity NPC150063
0.7368 Intermediate Similarity NPC469653
0.7368 Intermediate Similarity NPC471047
0.7368 Intermediate Similarity NPC91248

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC52198 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
0.9432 High Similarity NPD1698 Clinical (unspecified phase)
0.7708 Intermediate Similarity NPD5282 Discontinued
0.7667 Intermediate Similarity NPD6435 Approved
0.7579 Intermediate Similarity NPD5785 Approved
0.7444 Intermediate Similarity NPD5368 Approved
0.7419 Intermediate Similarity NPD5363 Approved
0.7363 Intermediate Similarity NPD5369 Approved
0.7358 Intermediate Similarity NPD6371 Approved
0.734 Intermediate Similarity NPD5786 Approved
0.732 Intermediate Similarity NPD6411 Approved
0.7238 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD1695 Approved
0.7113 Intermediate Similarity NPD6101 Approved
0.7097 Intermediate Similarity NPD4269 Approved
0.7097 Intermediate Similarity NPD4270 Approved
0.7075 Intermediate Similarity NPD5697 Approved
0.7053 Intermediate Similarity NPD1694 Approved
0.7033 Intermediate Similarity NPD5784 Clinical (unspecified phase)
0.7009 Intermediate Similarity NPD6881 Approved
0.7009 Intermediate Similarity NPD6899 Approved
0.6972 Remote Similarity NPD6649 Approved
0.6972 Remote Similarity NPD6650 Approved
0.6944 Remote Similarity NPD6012 Approved
0.6944 Remote Similarity NPD6013 Approved
0.6944 Remote Similarity NPD6014 Approved
0.6915 Remote Similarity NPD5209 Approved
0.69 Remote Similarity NPD5779 Approved
0.69 Remote Similarity NPD5778 Approved
0.6893 Remote Similarity NPD4225 Approved
0.6882 Remote Similarity NPD4252 Approved
0.6881 Remote Similarity NPD7102 Approved
0.6881 Remote Similarity NPD6883 Approved
0.6881 Remote Similarity NPD7290 Approved
0.6852 Remote Similarity NPD6011 Approved
0.6852 Remote Similarity NPD7320 Approved
0.6842 Remote Similarity NPD7154 Phase 3
0.6842 Remote Similarity NPD5362 Discontinued
0.6822 Remote Similarity NPD6675 Approved
0.6822 Remote Similarity NPD7128 Approved
0.6822 Remote Similarity NPD5739 Approved
0.6822 Remote Similarity NPD6402 Approved
0.6818 Remote Similarity NPD8130 Phase 1
0.6818 Remote Similarity NPD6617 Approved
0.6818 Remote Similarity NPD6869 Approved
0.6818 Remote Similarity NPD6847 Approved
0.68 Remote Similarity NPD7983 Approved
0.6789 Remote Similarity NPD6373 Approved
0.6789 Remote Similarity NPD6372 Approved
0.6759 Remote Similarity NPD5701 Approved
0.6757 Remote Similarity NPD8297 Approved
0.6757 Remote Similarity NPD6882 Approved
0.6733 Remote Similarity NPD6399 Phase 3
0.6702 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6695 Remote Similarity NPD7492 Approved
0.6667 Remote Similarity NPD5286 Approved
0.6667 Remote Similarity NPD4696 Approved
0.6667 Remote Similarity NPD5285 Approved
0.6639 Remote Similarity NPD6616 Approved
0.6638 Remote Similarity NPD6319 Approved
0.6638 Remote Similarity NPD6054 Approved
0.6635 Remote Similarity NPD7902 Approved
0.6635 Remote Similarity NPD6084 Phase 2
0.6635 Remote Similarity NPD6083 Phase 2
0.6634 Remote Similarity NPD6079 Approved
0.6633 Remote Similarity NPD4249 Approved
0.6602 Remote Similarity NPD5695 Phase 3
0.6583 Remote Similarity NPD7078 Approved
0.6581 Remote Similarity NPD6291 Clinical (unspecified phase)
0.6581 Remote Similarity NPD6016 Approved
0.6581 Remote Similarity NPD6015 Approved
0.6571 Remote Similarity NPD5696 Approved
0.6566 Remote Similarity NPD4251 Approved
0.6566 Remote Similarity NPD4250 Approved
0.6562 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6542 Remote Similarity NPD4633 Approved
0.6542 Remote Similarity NPD5226 Approved
0.6542 Remote Similarity NPD5224 Approved
0.6542 Remote Similarity NPD5225 Approved
0.6542 Remote Similarity NPD5211 Phase 2
0.6538 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6538 Remote Similarity NPD5221 Approved
0.6538 Remote Similarity NPD5222 Approved
0.6531 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6529 Remote Similarity NPD7736 Approved
0.6526 Remote Similarity NPD4822 Approved
0.6526 Remote Similarity NPD4819 Approved
0.6526 Remote Similarity NPD4821 Approved
0.6526 Remote Similarity NPD4820 Approved
0.6525 Remote Similarity NPD6370 Approved
0.6525 Remote Similarity NPD5988 Approved
0.6522 Remote Similarity NPD7115 Discovery
0.6514 Remote Similarity NPD6008 Approved
0.6505 Remote Similarity NPD7748 Approved
0.65 Remote Similarity NPD6903 Approved
0.6489 Remote Similarity NPD4268 Approved
0.6489 Remote Similarity NPD4271 Approved
0.6481 Remote Similarity NPD5175 Approved
0.6481 Remote Similarity NPD5174 Approved
0.6476 Remote Similarity NPD5173 Approved
0.6476 Remote Similarity NPD4755 Approved
0.6471 Remote Similarity NPD5281 Approved
0.6471 Remote Similarity NPD7515 Phase 2
0.6471 Remote Similarity NPD5284 Approved
0.6465 Remote Similarity NPD7146 Approved
0.6465 Remote Similarity NPD6684 Approved
0.6465 Remote Similarity NPD5330 Approved
0.6465 Remote Similarity NPD7521 Approved
0.6465 Remote Similarity NPD3618 Phase 1
0.6465 Remote Similarity NPD7334 Approved
0.6465 Remote Similarity NPD6409 Approved
0.6449 Remote Similarity NPD5223 Approved
0.6442 Remote Similarity NPD4629 Approved
0.6442 Remote Similarity NPD5210 Approved
0.6436 Remote Similarity NPD5328 Approved
0.6435 Remote Similarity NPD6274 Approved
0.6429 Remote Similarity NPD3665 Phase 1
0.6429 Remote Similarity NPD4634 Approved
0.6429 Remote Similarity NPD3666 Approved
0.6429 Remote Similarity NPD3133 Approved
0.6422 Remote Similarity NPD5141 Approved
0.641 Remote Similarity NPD7101 Approved
0.641 Remote Similarity NPD7100 Approved
0.6404 Remote Similarity NPD4632 Approved
0.64 Remote Similarity NPD3573 Approved
0.6396 Remote Similarity NPD6686 Approved
0.6381 Remote Similarity NPD4697 Phase 3
0.6381 Remote Similarity NPD7839 Suspended
0.6379 Remote Similarity NPD6317 Approved
0.6373 Remote Similarity NPD6698 Approved
0.6373 Remote Similarity NPD5207 Approved
0.6373 Remote Similarity NPD46 Approved
0.6372 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6364 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6356 Remote Similarity NPD6059 Approved
0.6355 Remote Similarity NPD4700 Approved
0.6346 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6346 Remote Similarity NPD7900 Approved
0.6337 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6337 Remote Similarity NPD5737 Approved
0.6337 Remote Similarity NPD6672 Approved
0.6325 Remote Similarity NPD6313 Approved
0.6325 Remote Similarity NPD6314 Approved
0.6325 Remote Similarity NPD6335 Approved
0.6316 Remote Similarity NPD6053 Discontinued
0.6311 Remote Similarity NPD7637 Suspended
0.6311 Remote Similarity NPD8293 Discontinued
0.63 Remote Similarity NPD5279 Phase 3
0.63 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6293 Remote Similarity NPD6868 Approved
0.6286 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6275 Remote Similarity NPD5370 Suspended
0.6275 Remote Similarity NPD4753 Phase 2
0.625 Remote Similarity NPD5345 Clinical (unspecified phase)
0.625 Remote Similarity NPD4730 Approved
0.625 Remote Similarity NPD4729 Approved
0.6239 Remote Similarity NPD6009 Approved
0.6224 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6224 Remote Similarity NPD3667 Approved
0.6222 Remote Similarity NPD229 Approved
0.6214 Remote Similarity NPD7838 Discovery
0.6198 Remote Similarity NPD8328 Phase 3
0.6186 Remote Similarity NPD4695 Discontinued
0.618 Remote Similarity NPD7331 Phase 2
0.6167 Remote Similarity NPD5983 Phase 2
0.6162 Remote Similarity NPD5331 Approved
0.6162 Remote Similarity NPD5332 Approved
0.6161 Remote Similarity NPD6412 Phase 2
0.6154 Remote Similarity NPD4810 Clinical (unspecified phase)
0.614 Remote Similarity NPD5251 Approved
0.614 Remote Similarity NPD5247 Approved
0.614 Remote Similarity NPD5248 Approved
0.614 Remote Similarity NPD5249 Phase 3
0.614 Remote Similarity NPD5250 Approved
0.6122 Remote Similarity NPD4790 Discontinued
0.6111 Remote Similarity NPD7638 Approved
0.6106 Remote Similarity NPD5128 Approved
0.61 Remote Similarity NPD4786 Approved
0.6095 Remote Similarity NPD4202 Approved
0.6087 Remote Similarity NPD5217 Approved
0.6087 Remote Similarity NPD5216 Approved
0.6087 Remote Similarity NPD5215 Approved
0.6071 Remote Similarity NPD4767 Approved
0.6071 Remote Similarity NPD4768 Approved
0.6067 Remote Similarity NPD7341 Phase 2
0.6066 Remote Similarity NPD7604 Phase 2
0.6055 Remote Similarity NPD7640 Approved
0.6055 Remote Similarity NPD7639 Approved
0.6038 Remote Similarity NPD6001 Approved
0.6036 Remote Similarity NPD4754 Approved
0.6033 Remote Similarity NPD6909 Approved
0.6033 Remote Similarity NPD6908 Approved
0.6 Remote Similarity NPD5135 Approved
0.6 Remote Similarity NPD5169 Approved
0.6 Remote Similarity NPD5134 Clinical (unspecified phase)
0.6 Remote Similarity NPD5694 Approved
0.6 Remote Similarity NPD8034 Phase 2
0.6 Remote Similarity NPD8035 Phase 2
0.598 Remote Similarity NPD5690 Phase 2
0.598 Remote Similarity NPD4519 Discontinued

Structure

External Identifiers

PubChem CID   442294
ChEMBL   CHEMBL188283
ZINC  

Physicochemical Properties

Molecular Weight:  264.14
ALogP:  -0.0359
MLogP:  2.67
XLogP:  0.733
# Rotatable Bonds:  4
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  
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Biological Activities  
Similar NPs/Drugs