Natural Product: NPC239895

Natural Product ID:  NPC239895
Common Name:   Petiolin C
IUPAC Name:  
Synonyms:   Petiolin C
Molecular Formula:   C22H32O5
Standard InCHIKey:  IHVZSYWNXZSPFS-YDGRNHKGSA-N
Standard InCHI:  InChI=1S/C22H32O5/c1-12(2)9-8-10-22(7,26)15-11-14-18(27-15)16(17(23)13(3)4)20(25)21(5,6)19(14)24/h9,13,15,23,26H,8,10-11H2,1-7H3/b17-16-/t15-,22+/m0/s1
Canonical SMILES:  CC(=CCC[C@]([C@@H]1CC2=C(O1)/C(=C(C(C)C)/O)/C(=O)C(C2=O)(C)C)(O)C)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
NPO12794.1 Hypericum pseudopetiolatum Under-species NA NA PMID[18430575]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT91 Cell Line KB Homo sapiens IC50 = 4.9 ug/ml 22582991
NPT330 Organism Trichophyton mentagrophytes Trichophyton mentagrophytes MIC = 33.3 ug/ml 22582991
NPT137 Cell Line L1210 Mus musculus IC50 = 3.3 ug/ml 19835393

  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 NPC239895 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 NPC477241
0.9043 High Similarity NPC93271
0.9043 High Similarity NPC135576
0.8842 High Similarity NPC472734
0.8842 High Similarity NPC472733
0.875 High Similarity NPC472731
0.875 High Similarity NPC472732
0.866 High Similarity NPC472730
0.866 High Similarity NPC472729
0.866 High Similarity NPC177680
0.866 High Similarity NPC153776
0.8632 High Similarity NPC469819
0.8632 High Similarity NPC114162
0.8571 High Similarity NPC472728
0.8571 High Similarity NPC472727
0.8367 Intermediate Similarity NPC27105
0.8283 Intermediate Similarity NPC471330
0.8283 Intermediate Similarity NPC203388
0.8283 Intermediate Similarity NPC35717
0.8283 Intermediate Similarity NPC472687
0.8283 Intermediate Similarity NPC99657
0.8283 Intermediate Similarity NPC471331
0.8191 Intermediate Similarity NPC476079
0.8191 Intermediate Similarity NPC113370
0.8191 Intermediate Similarity NPC103743
0.8155 Intermediate Similarity NPC478052
0.8105 Intermediate Similarity NPC143025
0.7981 Intermediate Similarity NPC471332
0.7981 Intermediate Similarity NPC471333
0.7979 Intermediate Similarity NPC307112
0.7938 Intermediate Similarity NPC166554
0.79 Intermediate Similarity NPC21681
0.79 Intermediate Similarity NPC472675
0.7843 Intermediate Similarity NPC54705
0.7822 Intermediate Similarity NPC53844
0.7812 Intermediate Similarity NPC23622
0.781 Intermediate Similarity NPC469852
0.7778 Intermediate Similarity NPC61275
0.7778 Intermediate Similarity NPC324683
0.7767 Intermediate Similarity NPC472753
0.7766 Intermediate Similarity NPC475083
0.7757 Intermediate Similarity NPC38154
0.7755 Intermediate Similarity NPC253177
0.7755 Intermediate Similarity NPC280592
0.7755 Intermediate Similarity NPC213636
0.7755 Intermediate Similarity NPC51653
0.7745 Intermediate Similarity NPC306908
0.7742 Intermediate Similarity NPC275766
0.7736 Intermediate Similarity NPC473169
0.7732 Intermediate Similarity NPC472008
0.7692 Intermediate Similarity NPC70369
0.7692 Intermediate Similarity NPC472754
0.7677 Intermediate Similarity NPC296114
0.7677 Intermediate Similarity NPC471329
0.7677 Intermediate Similarity NPC475441
0.7677 Intermediate Similarity NPC146852
0.7664 Intermediate Similarity NPC473482
0.7664 Intermediate Similarity NPC475418
0.7664 Intermediate Similarity NPC318363
0.7653 Intermediate Similarity NPC295448
0.7629 Intermediate Similarity NPC472007
0.7629 Intermediate Similarity NPC38885
0.7624 Intermediate Similarity NPC209355
0.7624 Intermediate Similarity NPC295347
0.7619 Intermediate Similarity NPC473624
0.7619 Intermediate Similarity NPC472755
0.7604 Intermediate Similarity NPC307126
0.7604 Intermediate Similarity NPC68303
0.76 Intermediate Similarity NPC248193
0.7596 Intermediate Similarity NPC469851
0.7593 Intermediate Similarity NPC475065
0.7593 Intermediate Similarity NPC228477
0.7593 Intermediate Similarity NPC137911
0.7589 Intermediate Similarity NPC476190
0.7576 Intermediate Similarity NPC469464
0.7576 Intermediate Similarity NPC265856
0.7576 Intermediate Similarity NPC316228
0.7576 Intermediate Similarity NPC51004
0.7573 Intermediate Similarity NPC278008
0.757 Intermediate Similarity NPC330011
0.757 Intermediate Similarity NPC329048
0.757 Intermediate Similarity NPC469853
0.7551 Intermediate Similarity NPC87189
0.7551 Intermediate Similarity NPC228415
0.7547 Intermediate Similarity NPC472756
0.7545 Intermediate Similarity NPC66108
0.7526 Intermediate Similarity NPC472009
0.7526 Intermediate Similarity NPC469483
0.7525 Intermediate Similarity NPC53685
0.7525 Intermediate Similarity NPC65829
0.7524 Intermediate Similarity NPC183571
0.7524 Intermediate Similarity NPC80781
0.7523 Intermediate Similarity NPC99760
0.7523 Intermediate Similarity NPC473627
0.7523 Intermediate Similarity NPC37116
0.75 Intermediate Similarity NPC166110
0.75 Intermediate Similarity NPC45579
0.75 Intermediate Similarity NPC475972
0.75 Intermediate Similarity NPC472705
0.75 Intermediate Similarity NPC30515
0.75 Intermediate Similarity NPC9868
0.7477 Intermediate Similarity NPC85529
0.7477 Intermediate Similarity NPC253223
0.7477 Intermediate Similarity NPC469454
0.7477 Intermediate Similarity NPC477125
0.7477 Intermediate Similarity NPC32006
0.7477 Intermediate Similarity NPC469496
0.7477 Intermediate Similarity NPC469463
0.7477 Intermediate Similarity NPC471204
0.7476 Intermediate Similarity NPC208094
0.7476 Intermediate Similarity NPC474977
0.7475 Intermediate Similarity NPC307411
0.7475 Intermediate Similarity NPC472676
0.7475 Intermediate Similarity NPC472688
0.7455 Intermediate Similarity NPC179798
0.7455 Intermediate Similarity NPC304180
0.7453 Intermediate Similarity NPC475321
0.7453 Intermediate Similarity NPC69171
0.7453 Intermediate Similarity NPC472747
0.7453 Intermediate Similarity NPC472750
0.7453 Intermediate Similarity NPC474165
0.7449 Intermediate Similarity NPC312561
0.7447 Intermediate Similarity NPC472948
0.7447 Intermediate Similarity NPC91332
0.7447 Intermediate Similarity NPC162741
0.7431 Intermediate Similarity NPC47951
0.7429 Intermediate Similarity NPC133907
0.7429 Intermediate Similarity NPC303559
0.7429 Intermediate Similarity NPC474742
0.7429 Intermediate Similarity NPC472637
0.7429 Intermediate Similarity NPC473174
0.7429 Intermediate Similarity NPC471401
0.7429 Intermediate Similarity NPC244456
0.7429 Intermediate Similarity NPC185141
0.7429 Intermediate Similarity NPC128733
0.7429 Intermediate Similarity NPC469657
0.7429 Intermediate Similarity NPC9878
0.7429 Intermediate Similarity NPC110443
0.7429 Intermediate Similarity NPC46998
0.7426 Intermediate Similarity NPC469692
0.7426 Intermediate Similarity NPC282644
0.7426 Intermediate Similarity NPC29798
0.7426 Intermediate Similarity NPC476300
0.7426 Intermediate Similarity NPC469645
0.7423 Intermediate Similarity NPC11804
0.7407 Intermediate Similarity NPC473911
0.7404 Intermediate Similarity NPC300584
0.7404 Intermediate Similarity NPC222303
0.74 Intermediate Similarity NPC476004
0.74 Intermediate Similarity NPC474761
0.74 Intermediate Similarity NPC51486
0.74 Intermediate Similarity NPC113393
0.74 Intermediate Similarity NPC281942
0.74 Intermediate Similarity NPC232426
0.7396 Intermediate Similarity NPC193198
0.7391 Intermediate Similarity NPC478051
0.7387 Intermediate Similarity NPC269530
0.7387 Intermediate Similarity NPC476801
0.7383 Intermediate Similarity NPC309190
0.7383 Intermediate Similarity NPC13385
0.7383 Intermediate Similarity NPC203659
0.7383 Intermediate Similarity NPC472748
0.7383 Intermediate Similarity NPC146731
0.7374 Intermediate Similarity NPC58532
0.7374 Intermediate Similarity NPC473658
0.7374 Intermediate Similarity NPC53454
0.7374 Intermediate Similarity NPC472677
0.7374 Intermediate Similarity NPC476708
0.7364 Intermediate Similarity NPC29133
0.7364 Intermediate Similarity NPC478211
0.7358 Intermediate Similarity NPC473163
0.7358 Intermediate Similarity NPC149371
0.7353 Intermediate Similarity NPC476415
0.7353 Intermediate Similarity NPC121825
0.7353 Intermediate Similarity NPC473162
0.7353 Intermediate Similarity NPC473172
0.7353 Intermediate Similarity NPC472976
0.7353 Intermediate Similarity NPC472977
0.7347 Intermediate Similarity NPC261721
0.7347 Intermediate Similarity NPC220478
0.7347 Intermediate Similarity NPC164393
0.7339 Intermediate Similarity NPC151393
0.7339 Intermediate Similarity NPC473807
0.7333 Intermediate Similarity NPC117685
0.7328 Intermediate Similarity NPC472000
0.7328 Intermediate Similarity NPC471999
0.7327 Intermediate Similarity NPC141831
0.7327 Intermediate Similarity NPC300312
0.7327 Intermediate Similarity NPC476705
0.7327 Intermediate Similarity NPC111114
0.7327 Intermediate Similarity NPC303697
0.7327 Intermediate Similarity NPC261607
0.7327 Intermediate Similarity NPC230623
0.7327 Intermediate Similarity NPC184463
0.7327 Intermediate Similarity NPC472975
0.7321 Intermediate Similarity NPC478212
0.7321 Intermediate Similarity NPC321496
0.7321 Intermediate Similarity NPC56448
0.732 Intermediate Similarity NPC243618
0.732 Intermediate Similarity NPC31086

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC239895 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
0.7184 Intermediate Similarity NPD5282 Discontinued
0.713 Intermediate Similarity NPD7115 Discovery
0.7115 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7113 Intermediate Similarity NPD4800 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD4225 Approved
0.7059 Intermediate Similarity NPD5785 Approved
0.7054 Intermediate Similarity NPD6371 Approved
0.699 Remote Similarity NPD7983 Approved
0.699 Remote Similarity NPD6411 Approved
0.6923 Remote Similarity NPD5779 Approved
0.6923 Remote Similarity NPD5778 Approved
0.6893 Remote Similarity NPD6698 Approved
0.6893 Remote Similarity NPD46 Approved
0.6796 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6796 Remote Similarity NPD6101 Approved
0.6786 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6778 Remote Similarity NPD7331 Phase 2
0.6768 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6726 Remote Similarity NPD6686 Approved
0.67 Remote Similarity NPD6110 Phase 1
0.6667 Remote Similarity NPD5279 Phase 3
0.6667 Remote Similarity NPD7341 Phase 2
0.6667 Remote Similarity NPD5786 Approved
0.6638 Remote Similarity NPD6053 Discontinued
0.6635 Remote Similarity NPD5328 Approved
0.6604 Remote Similarity NPD6399 Phase 3
0.66 Remote Similarity NPD5209 Approved
0.6571 Remote Similarity NPD7838 Discovery
0.6569 Remote Similarity NPD5363 Approved
0.6569 Remote Similarity NPD1694 Approved
0.6566 Remote Similarity NPD4695 Discontinued
0.6562 Remote Similarity NPD8039 Approved
0.6535 Remote Similarity NPD7260 Phase 2
0.6535 Remote Similarity NPD7154 Phase 3
0.6509 Remote Similarity NPD6079 Approved
0.6505 Remote Similarity NPD3618 Phase 1
0.6505 Remote Similarity NPD3574 Clinical (unspecified phase)
0.65 Remote Similarity NPD5369 Approved
0.6475 Remote Similarity NPD8513 Phase 3
0.6475 Remote Similarity NPD8516 Approved
0.6475 Remote Similarity NPD8517 Approved
0.6475 Remote Similarity NPD8515 Approved
0.6471 Remote Similarity NPD4786 Approved
0.6471 Remote Similarity NPD3133 Approved
0.6471 Remote Similarity NPD3665 Phase 1
0.6471 Remote Similarity NPD3666 Approved
0.6455 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6436 Remote Similarity NPD4270 Approved
0.6436 Remote Similarity NPD4269 Approved
0.6436 Remote Similarity NPD3667 Approved
0.6429 Remote Similarity NPD4756 Discovery
0.6422 Remote Similarity NPD7839 Suspended
0.6422 Remote Similarity NPD4697 Phase 3
0.6408 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6408 Remote Similarity NPD1696 Phase 3
0.6404 Remote Similarity NPD6402 Approved
0.6404 Remote Similarity NPD7128 Approved
0.6404 Remote Similarity NPD5739 Approved
0.6404 Remote Similarity NPD6675 Approved
0.64 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6389 Remote Similarity NPD7748 Approved
0.6379 Remote Similarity NPD6373 Approved
0.6379 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6379 Remote Similarity NPD6372 Approved
0.6378 Remote Similarity NPD7319 Approved
0.6364 Remote Similarity NPD4755 Approved
0.6364 Remote Similarity NPD6084 Phase 2
0.6364 Remote Similarity NPD6083 Phase 2
0.6364 Remote Similarity NPD7902 Approved
0.6356 Remote Similarity NPD8297 Approved
0.6355 Remote Similarity NPD5281 Approved
0.6355 Remote Similarity NPD5284 Approved
0.6348 Remote Similarity NPD6412 Phase 2
0.6346 Remote Similarity NPD4519 Discontinued
0.6346 Remote Similarity NPD7334 Approved
0.6346 Remote Similarity NPD4623 Approved
0.6346 Remote Similarity NPD7146 Approved
0.6346 Remote Similarity NPD5330 Approved
0.6346 Remote Similarity NPD6409 Approved
0.6346 Remote Similarity NPD4694 Approved
0.6346 Remote Similarity NPD6684 Approved
0.6346 Remote Similarity NPD7521 Approved
0.6346 Remote Similarity NPD5280 Approved
0.633 Remote Similarity NPD5695 Phase 3
0.6325 Remote Similarity NPD4634 Approved
0.6325 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6321 Remote Similarity NPD7285 Clinical (unspecified phase)
0.6321 Remote Similarity NPD4753 Phase 2
0.6311 Remote Similarity NPD6400 Clinical (unspecified phase)
0.6306 Remote Similarity NPD7638 Approved
0.6306 Remote Similarity NPD5696 Approved
0.6293 Remote Similarity NPD7320 Approved
0.6293 Remote Similarity NPD6899 Approved
0.6293 Remote Similarity NPD6881 Approved
0.6293 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6286 Remote Similarity NPD7524 Approved
0.6283 Remote Similarity NPD5211 Phase 2
0.6275 Remote Similarity NPD4223 Phase 3
0.6275 Remote Similarity NPD4221 Approved
0.6273 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6273 Remote Similarity NPD5221 Approved
0.6273 Remote Similarity NPD5222 Approved
0.6271 Remote Similarity NPD6650 Approved
0.6271 Remote Similarity NPD6649 Approved
0.6271 Remote Similarity NPD7116 Clinical (unspecified phase)
0.627 Remote Similarity NPD7507 Approved
0.626 Remote Similarity NPD6054 Approved
0.626 Remote Similarity NPD6059 Approved
0.626 Remote Similarity NPD6319 Approved
0.625 Remote Similarity NPD5286 Approved
0.625 Remote Similarity NPD5285 Approved
0.625 Remote Similarity NPD5329 Approved
0.625 Remote Similarity NPD7640 Approved
0.625 Remote Similarity NPD4696 Approved
0.625 Remote Similarity NPD4700 Approved
0.625 Remote Similarity NPD7639 Approved
0.6238 Remote Similarity NPD4252 Approved
0.6231 Remote Similarity NPD6845 Suspended
0.6226 Remote Similarity NPD4518 Approved
0.6226 Remote Similarity NPD5737 Approved
0.6226 Remote Similarity NPD6672 Approved
0.6226 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6226 Remote Similarity NPD6903 Approved
0.622 Remote Similarity NPD8074 Phase 3
0.6216 Remote Similarity NPD5173 Approved
0.6207 Remote Similarity NPD5697 Approved
0.6207 Remote Similarity NPD5701 Approved
0.6204 Remote Similarity NPD7515 Phase 2
0.6204 Remote Similarity NPD7637 Suspended
0.6204 Remote Similarity NPD5693 Phase 1
0.6204 Remote Similarity NPD6050 Approved
0.62 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6195 Remote Similarity NPD5223 Approved
0.6186 Remote Similarity NPD7290 Approved
0.6186 Remote Similarity NPD7102 Approved
0.6186 Remote Similarity NPD6883 Approved
0.6182 Remote Similarity NPD4629 Approved
0.6182 Remote Similarity NPD5210 Approved
0.6174 Remote Similarity NPD5141 Approved
0.6167 Remote Similarity NPD4632 Approved
0.6162 Remote Similarity NPD6933 Approved
0.616 Remote Similarity NPD6370 Approved
0.6154 Remote Similarity NPD4197 Approved
0.6154 Remote Similarity NPD3668 Phase 3
0.6154 Remote Similarity NPD6011 Approved
0.6148 Remote Similarity NPD7500 Approved
0.6147 Remote Similarity NPD4202 Approved
0.614 Remote Similarity NPD5225 Approved
0.614 Remote Similarity NPD4633 Approved
0.614 Remote Similarity NPD5224 Approved
0.614 Remote Similarity NPD5226 Approved
0.6134 Remote Similarity NPD6617 Approved
0.6134 Remote Similarity NPD8130 Phase 1
0.6134 Remote Similarity NPD6869 Approved
0.6134 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6134 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6134 Remote Similarity NPD6847 Approved
0.6129 Remote Similarity NPD7299 Clinical (unspecified phase)
0.6121 Remote Similarity NPD6008 Approved
0.6117 Remote Similarity NPD6435 Approved
0.6111 Remote Similarity NPD5692 Phase 3
0.6111 Remote Similarity NPD8328 Phase 3
0.6111 Remote Similarity NPD4096 Approved
0.6111 Remote Similarity NPD5207 Approved
0.6102 Remote Similarity NPD6012 Approved
0.6102 Remote Similarity NPD6013 Approved
0.6102 Remote Similarity NPD6014 Approved
0.6091 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6091 Remote Similarity NPD7900 Approved
0.6087 Remote Similarity NPD5175 Approved
0.6087 Remote Similarity NPD4754 Approved
0.6087 Remote Similarity NPD5174 Approved
0.6083 Remote Similarity NPD6882 Approved
0.608 Remote Similarity NPD6016 Approved
0.608 Remote Similarity NPD8444 Approved
0.608 Remote Similarity NPD7503 Approved
0.608 Remote Similarity NPD6015 Approved
0.6068 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6064 Remote Similarity NPD3704 Approved
0.6063 Remote Similarity NPD7492 Approved
0.6058 Remote Similarity NPD5362 Discontinued
0.6058 Remote Similarity NPD6695 Phase 3
0.6055 Remote Similarity NPD5694 Approved
0.605 Remote Similarity NPD2067 Discontinued
0.604 Remote Similarity NPD3617 Approved
0.6038 Remote Similarity NPD4689 Approved
0.6038 Remote Similarity NPD4693 Phase 3
0.6038 Remote Similarity NPD5690 Phase 2
0.6038 Remote Similarity NPD5205 Approved
0.6038 Remote Similarity NPD4690 Approved
0.6038 Remote Similarity NPD4688 Approved
0.6038 Remote Similarity NPD4138 Approved
0.6036 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6032 Remote Similarity NPD5988 Approved
0.6019 Remote Similarity NPD6904 Approved
0.6019 Remote Similarity NPD6673 Approved
0.6019 Remote Similarity NPD6080 Approved
0.6016 Remote Similarity NPD8451 Approved
0.6016 Remote Similarity NPD6616 Approved
0.6 Remote Similarity NPD7338 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID  
ChEMBL   CHEMBL498771
ZINC  

Physicochemical Properties

Molecular Weight:  376.22
ALogP:  2.1136
MLogP:  3.33
XLogP:  3.582
# Rotatable Bonds:  14
Polar Surface Area:  83.83
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  27

Download Data

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