Natural Product: NPC166554

Natural Product ID:  NPC166554
Common Name:   Bicycloalternarene C
IUPAC Name:   (2E,6E,10S)-10-hydroxy-10-[(2S,7R)-7-hydroxy-4-oxo-3,5,6,7-tetrahydro-2H-1-benzofuran-2-yl]-2,6-dimethylundeca-2,6-dienoic acid
Synonyms:  
Molecular Formula:   C21H30O6
Standard InCHIKey:  QETAPCLLJJFFKU-IBHBTLNGSA-N
Standard InCHI:  InChI=1S/C21H30O6/c1-13(6-4-8-14(2)20(24)25)7-5-11-21(3,26)18-12-15-16(22)9-10-17(23)19(15)27-18/h7-8,17-18,23,26H,4-6,9-12H2,1-3H3,(H,24,25)/b13-7+,14-8+/t17-,18+,21+/m1/s1
Canonical SMILES:  C/C(=CCC[C@@]([C@H]1OC2=C(C1)C(=O)CC[C@H]2O)(O)C)/CC/C=C(/C(=O)O)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
NPO32811 Alternaria sp. JJY-32 Species Pleosporaceae Eukaryota PMID[24128115]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified IC50 = 67000 nM 18280170

  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 NPC166554 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
0.9535 High Similarity NPC265856
0.9022 High Similarity NPC300584
0.871 High Similarity NPC20066
0.8652 High Similarity NPC472008
0.8539 High Similarity NPC472007
0.8427 Intermediate Similarity NPC472009
0.8409 Intermediate Similarity NPC243618
0.8409 Intermediate Similarity NPC70424
0.8333 Intermediate Similarity NPC179659
0.8172 Intermediate Similarity NPC146852
0.8163 Intermediate Similarity NPC70369
0.8161 Intermediate Similarity NPC162741
0.8161 Intermediate Similarity NPC91332
0.8111 Intermediate Similarity NPC21469
0.81 Intermediate Similarity NPC469852
0.8085 Intermediate Similarity NPC475912
0.8085 Intermediate Similarity NPC273579
0.8085 Intermediate Similarity NPC295204
0.8085 Intermediate Similarity NPC162205
0.8085 Intermediate Similarity NPC288240
0.8085 Intermediate Similarity NPC61275
0.8065 Intermediate Similarity NPC471399
0.8065 Intermediate Similarity NPC476004
0.8065 Intermediate Similarity NPC474761
0.8043 Intermediate Similarity NPC228415
0.8043 Intermediate Similarity NPC87189
0.8 Intermediate Similarity NPC9868
0.8 Intermediate Similarity NPC474035
0.8 Intermediate Similarity NPC477241
0.8 Intermediate Similarity NPC81386
0.7979 Intermediate Similarity NPC30515
0.7957 Intermediate Similarity NPC474032
0.7957 Intermediate Similarity NPC295312
0.7955 Intermediate Similarity NPC233377
0.7938 Intermediate Similarity NPC239895
0.7935 Intermediate Similarity NPC300779
0.7917 Intermediate Similarity NPC36954
0.7917 Intermediate Similarity NPC14961
0.7917 Intermediate Similarity NPC270013
0.7912 Intermediate Similarity NPC307126
0.7912 Intermediate Similarity NPC68303
0.7895 Intermediate Similarity NPC81419
0.7895 Intermediate Similarity NPC469645
0.7895 Intermediate Similarity NPC469692
0.7895 Intermediate Similarity NPC179746
0.7882 Intermediate Similarity NPC160540
0.7879 Intermediate Similarity NPC185141
0.7879 Intermediate Similarity NPC471401
0.7879 Intermediate Similarity NPC46998
0.7879 Intermediate Similarity NPC128733
0.7879 Intermediate Similarity NPC110443
0.7879 Intermediate Similarity NPC133907
0.7872 Intermediate Similarity NPC51004
0.7857 Intermediate Similarity NPC35717
0.7857 Intermediate Similarity NPC306908
0.7849 Intermediate Similarity NPC202672
0.7849 Intermediate Similarity NPC153805
0.7835 Intermediate Similarity NPC93271
0.7835 Intermediate Similarity NPC135576
0.7826 Intermediate Similarity NPC112685
0.7812 Intermediate Similarity NPC121825
0.781 Intermediate Similarity NPC66108
0.7802 Intermediate Similarity NPC72464
0.7802 Intermediate Similarity NPC31086
0.7789 Intermediate Similarity NPC184463
0.7789 Intermediate Similarity NPC12172
0.7789 Intermediate Similarity NPC475441
0.7789 Intermediate Similarity NPC208886
0.7789 Intermediate Similarity NPC473321
0.7778 Intermediate Similarity NPC474291
0.7778 Intermediate Similarity NPC474252
0.7766 Intermediate Similarity NPC307411
0.7766 Intermediate Similarity NPC307092
0.7753 Intermediate Similarity NPC470945
0.7753 Intermediate Similarity NPC103634
0.7753 Intermediate Similarity NPC470946
0.7753 Intermediate Similarity NPC470947
0.7742 Intermediate Similarity NPC471738
0.7727 Intermediate Similarity NPC108816
0.7727 Intermediate Similarity NPC93763
0.7717 Intermediate Similarity NPC137033
0.7717 Intermediate Similarity NPC28887
0.7717 Intermediate Similarity NPC182383
0.7717 Intermediate Similarity NPC77971
0.7708 Intermediate Similarity NPC476300
0.7708 Intermediate Similarity NPC11456
0.7708 Intermediate Similarity NPC212486
0.77 Intermediate Similarity NPC469851
0.7692 Intermediate Similarity NPC477784
0.7692 Intermediate Similarity NPC477786
0.7692 Intermediate Similarity NPC477785
0.7692 Intermediate Similarity NPC38154
0.7684 Intermediate Similarity NPC473619
0.7684 Intermediate Similarity NPC469464
0.7684 Intermediate Similarity NPC473448
0.7677 Intermediate Similarity NPC473326
0.767 Intermediate Similarity NPC469853
0.7667 Intermediate Similarity NPC325031
0.766 Intermediate Similarity NPC474471
0.766 Intermediate Similarity NPC473658
0.766 Intermediate Similarity NPC227379
0.7653 Intermediate Similarity NPC472733
0.7653 Intermediate Similarity NPC472734
0.7653 Intermediate Similarity NPC476315
0.7647 Intermediate Similarity NPC100487
0.7634 Intermediate Similarity NPC219498
0.7634 Intermediate Similarity NPC477010
0.7634 Intermediate Similarity NPC473687
0.7634 Intermediate Similarity NPC47937
0.7634 Intermediate Similarity NPC204686
0.7634 Intermediate Similarity NPC164393
0.7634 Intermediate Similarity NPC134807
0.7634 Intermediate Similarity NPC469483
0.7634 Intermediate Similarity NPC305475
0.7634 Intermediate Similarity NPC261721
0.7634 Intermediate Similarity NPC134885
0.7634 Intermediate Similarity NPC210218
0.7634 Intermediate Similarity NPC308412
0.7634 Intermediate Similarity NPC475461
0.7629 Intermediate Similarity NPC303942
0.7629 Intermediate Similarity NPC57405
0.7629 Intermediate Similarity NPC469632
0.7629 Intermediate Similarity NPC71589
0.7624 Intermediate Similarity NPC39996
0.7619 Intermediate Similarity NPC239097
0.7619 Intermediate Similarity NPC37116
0.7614 Intermediate Similarity NPC116177
0.7614 Intermediate Similarity NPC320630
0.7614 Intermediate Similarity NPC7563
0.7609 Intermediate Similarity NPC295799
0.7609 Intermediate Similarity NPC472957
0.7609 Intermediate Similarity NPC472958
0.7609 Intermediate Similarity NPC96259
0.7609 Intermediate Similarity NPC141193
0.7604 Intermediate Similarity NPC261607
0.7604 Intermediate Similarity NPC111114
0.7604 Intermediate Similarity NPC300312
0.76 Intermediate Similarity NPC288876
0.7582 Intermediate Similarity NPC475690
0.7582 Intermediate Similarity NPC173609
0.7579 Intermediate Similarity NPC477011
0.7579 Intermediate Similarity NPC280612
0.7579 Intermediate Similarity NPC51358
0.7579 Intermediate Similarity NPC212598
0.7579 Intermediate Similarity NPC268298
0.7579 Intermediate Similarity NPC83423
0.7576 Intermediate Similarity NPC472732
0.7576 Intermediate Similarity NPC40812
0.7576 Intermediate Similarity NPC474343
0.7576 Intermediate Similarity NPC472731
0.7553 Intermediate Similarity NPC312561
0.7553 Intermediate Similarity NPC160138
0.7553 Intermediate Similarity NPC248602
0.7553 Intermediate Similarity NPC23622
0.7553 Intermediate Similarity NPC72513
0.7553 Intermediate Similarity NPC237540
0.7551 Intermediate Similarity NPC91408
0.7551 Intermediate Similarity NPC272050
0.7551 Intermediate Similarity NPC472469
0.7549 Intermediate Similarity NPC472755
0.7549 Intermediate Similarity NPC475871
0.7549 Intermediate Similarity NPC475945
0.7528 Intermediate Similarity NPC128276
0.7528 Intermediate Similarity NPC192006
0.7528 Intermediate Similarity NPC267231
0.7528 Intermediate Similarity NPC231739
0.7527 Intermediate Similarity NPC100921
0.7527 Intermediate Similarity NPC107986
0.7527 Intermediate Similarity NPC1083
0.7527 Intermediate Similarity NPC261380
0.7527 Intermediate Similarity NPC82795
0.7527 Intermediate Similarity NPC473669
0.7527 Intermediate Similarity NPC231009
0.7527 Intermediate Similarity NPC283085
0.7527 Intermediate Similarity NPC125290
0.7527 Intermediate Similarity NPC11804
0.7527 Intermediate Similarity NPC103284
0.7527 Intermediate Similarity NPC223871
0.7527 Intermediate Similarity NPC255307
0.7527 Intermediate Similarity NPC165162
0.7527 Intermediate Similarity NPC473651
0.7527 Intermediate Similarity NPC477018
0.7527 Intermediate Similarity NPC110710
0.7527 Intermediate Similarity NPC473478
0.7527 Intermediate Similarity NPC132496
0.7527 Intermediate Similarity NPC286338
0.7527 Intermediate Similarity NPC66346
0.7525 Intermediate Similarity NPC9878
0.7525 Intermediate Similarity NPC474742
0.7525 Intermediate Similarity NPC476270
0.7524 Intermediate Similarity NPC471400
0.75 Intermediate Similarity NPC129419
0.75 Intermediate Similarity NPC472730
0.75 Intermediate Similarity NPC153776
0.75 Intermediate Similarity NPC40746
0.75 Intermediate Similarity NPC161045
0.75 Intermediate Similarity NPC278008
0.75 Intermediate Similarity NPC52609
0.75 Intermediate Similarity NPC11620
0.75 Intermediate Similarity NPC177680

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC166554 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
0.75 Intermediate Similarity NPD7154 Phase 3
0.7416 Intermediate Similarity NPD4756 Discovery
0.734 Intermediate Similarity NPD5363 Approved
0.732 Intermediate Similarity NPD46 Approved
0.732 Intermediate Similarity NPD6698 Approved
0.7312 Intermediate Similarity NPD6110 Phase 1
0.7263 Intermediate Similarity NPD5786 Approved
0.7245 Intermediate Similarity NPD7983 Approved
0.7143 Intermediate Similarity NPD5785 Approved
0.7059 Intermediate Similarity NPD7331 Phase 2
0.703 Intermediate Similarity NPD1698 Clinical (unspecified phase)
0.7021 Intermediate Similarity NPD4269 Approved
0.7021 Intermediate Similarity NPD4270 Approved
0.7 Intermediate Similarity NPD5779 Approved
0.7 Intermediate Similarity NPD5778 Approved
0.699 Remote Similarity NPD4225 Approved
0.6979 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6972 Remote Similarity NPD6371 Approved
0.6947 Remote Similarity NPD5362 Discontinued
0.6915 Remote Similarity NPD5369 Approved
0.6903 Remote Similarity NPD7115 Discovery
0.6842 Remote Similarity NPD6435 Approved
0.6827 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6809 Remote Similarity NPD4252 Approved
0.6774 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6701 Remote Similarity NPD6400 Clinical (unspecified phase)
0.67 Remote Similarity NPD6101 Approved
0.67 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6697 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6696 Remote Similarity NPD6053 Discontinued
0.6667 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6667 Remote Similarity NPD3704 Approved
0.6636 Remote Similarity NPD6686 Approved
0.6635 Remote Similarity NPD7839 Suspended
0.6634 Remote Similarity NPD7838 Discovery
0.6633 Remote Similarity NPD1694 Approved
0.6632 Remote Similarity NPD4822 Approved
0.6632 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6632 Remote Similarity NPD4820 Approved
0.6632 Remote Similarity NPD4819 Approved
0.6632 Remote Similarity NPD4821 Approved
0.6632 Remote Similarity NPD5368 Approved
0.6602 Remote Similarity NPD5282 Discontinued
0.6569 Remote Similarity NPD6411 Approved
0.6566 Remote Similarity NPD4249 Approved
0.6552 Remote Similarity NPD7341 Phase 2
0.6549 Remote Similarity NPD8297 Approved
0.6545 Remote Similarity NPD5697 Approved
0.6542 Remote Similarity NPD5344 Discontinued
0.6512 Remote Similarity NPD2664 Clinical (unspecified phase)
0.6505 Remote Similarity NPD6399 Phase 3
0.65 Remote Similarity NPD4251 Approved
0.65 Remote Similarity NPD4250 Approved
0.6495 Remote Similarity NPD4800 Clinical (unspecified phase)
0.6491 Remote Similarity NPD4632 Approved
0.6486 Remote Similarity NPD6899 Approved
0.6486 Remote Similarity NPD6011 Approved
0.6486 Remote Similarity NPD6881 Approved
0.6465 Remote Similarity NPD1696 Phase 3
0.646 Remote Similarity NPD6649 Approved
0.646 Remote Similarity NPD8413 Clinical (unspecified phase)
0.646 Remote Similarity NPD6650 Approved
0.6455 Remote Similarity NPD6675 Approved
0.6455 Remote Similarity NPD6402 Approved
0.6455 Remote Similarity NPD7128 Approved
0.6455 Remote Similarity NPD5739 Approved
0.6429 Remote Similarity NPD6012 Approved
0.6429 Remote Similarity NPD5332 Approved
0.6429 Remote Similarity NPD6014 Approved
0.6429 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6429 Remote Similarity NPD6013 Approved
0.6429 Remote Similarity NPD5331 Approved
0.6429 Remote Similarity NPD6372 Approved
0.6429 Remote Similarity NPD6373 Approved
0.6421 Remote Similarity NPD4268 Approved
0.6421 Remote Similarity NPD4271 Approved
0.6415 Remote Similarity NPD6084 Phase 2
0.6415 Remote Similarity NPD6083 Phase 2
0.6408 Remote Similarity NPD4810 Clinical (unspecified phase)
0.6396 Remote Similarity NPD5701 Approved
0.6392 Remote Similarity NPD4790 Discontinued
0.6387 Remote Similarity NPD8515 Approved
0.6387 Remote Similarity NPD8517 Approved
0.6387 Remote Similarity NPD8513 Phase 3
0.6387 Remote Similarity NPD8516 Approved
0.6381 Remote Similarity NPD5695 Phase 3
0.6373 Remote Similarity NPD5370 Suspended
0.6372 Remote Similarity NPD7290 Approved
0.6372 Remote Similarity NPD6883 Approved
0.6372 Remote Similarity NPD7102 Approved
0.6364 Remote Similarity NPD2685 Clinical (unspecified phase)
0.6355 Remote Similarity NPD5696 Approved
0.6339 Remote Similarity NPD7320 Approved
0.633 Remote Similarity NPD5211 Phase 2
0.6316 Remote Similarity NPD6617 Approved
0.6316 Remote Similarity NPD8130 Phase 1
0.6316 Remote Similarity NPD6847 Approved
0.6316 Remote Similarity NPD6869 Approved
0.6316 Remote Similarity NPD7116 Clinical (unspecified phase)
0.6303 Remote Similarity NPD6319 Approved
0.63 Remote Similarity NPD6082 Clinical (unspecified phase)
0.6292 Remote Similarity NPD6108 Clinical (unspecified phase)
0.6289 Remote Similarity NPD4695 Discontinued
0.6286 Remote Similarity NPD7748 Approved
0.6277 Remote Similarity NPD8039 Approved
0.6271 Remote Similarity NPD7641 Discontinued
0.6262 Remote Similarity NPD7902 Approved
0.6261 Remote Similarity NPD6882 Approved
0.625 Remote Similarity NPD6079 Approved
0.625 Remote Similarity NPD7515 Phase 2
0.625 Remote Similarity NPD3197 Phase 1
0.6238 Remote Similarity NPD6684 Approved
0.6238 Remote Similarity NPD7334 Approved
0.6238 Remote Similarity NPD7521 Approved
0.6238 Remote Similarity NPD3618 Phase 1
0.6238 Remote Similarity NPD6422 Discontinued
0.6238 Remote Similarity NPD7146 Approved
0.6238 Remote Similarity NPD6409 Approved
0.6238 Remote Similarity NPD5330 Approved
0.6228 Remote Similarity NPD2067 Discontinued
0.6228 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6222 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6216 Remote Similarity NPD5141 Approved
0.6214 Remote Similarity NPD5328 Approved
0.62 Remote Similarity NPD3665 Phase 1
0.62 Remote Similarity NPD3666 Approved
0.62 Remote Similarity NPD3133 Approved
0.6186 Remote Similarity NPD6009 Approved
0.6176 Remote Similarity NPD3573 Approved
0.6174 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6168 Remote Similarity NPD5221 Approved
0.6168 Remote Similarity NPD4697 Phase 3
0.6168 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6168 Remote Similarity NPD5222 Approved
0.6162 Remote Similarity NPD3667 Approved
0.6162 Remote Similarity NPD5209 Approved
0.6161 Remote Similarity NPD6008 Approved
0.6148 Remote Similarity NPD7642 Approved
0.6147 Remote Similarity NPD7639 Approved
0.6147 Remote Similarity NPD5286 Approved
0.6147 Remote Similarity NPD6648 Approved
0.6147 Remote Similarity NPD4696 Approved
0.6147 Remote Similarity NPD7640 Approved
0.6147 Remote Similarity NPD5285 Approved
0.6129 Remote Similarity NPD8074 Phase 3
0.6126 Remote Similarity NPD6647 Phase 2
0.6122 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6117 Remote Similarity NPD6672 Approved
0.6117 Remote Similarity NPD6903 Approved
0.6117 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6117 Remote Similarity NPD5737 Approved
0.6116 Remote Similarity NPD5983 Phase 2
0.6111 Remote Similarity NPD5173 Approved
0.6111 Remote Similarity NPD4755 Approved
0.6106 Remote Similarity NPD6412 Phase 2
0.6102 Remote Similarity NPD6274 Approved
0.6102 Remote Similarity NPD690 Clinical (unspecified phase)
0.6095 Remote Similarity NPD7637 Suspended
0.6095 Remote Similarity NPD5284 Approved
0.6095 Remote Similarity NPD5281 Approved
0.6091 Remote Similarity NPD5223 Approved
0.6078 Remote Similarity NPD4623 Approved
0.6078 Remote Similarity NPD4519 Discontinued
0.6078 Remote Similarity NPD5279 Phase 3
0.6075 Remote Similarity NPD5210 Approved
0.6075 Remote Similarity NPD4629 Approved
0.6066 Remote Similarity NPD8080 Discontinued
0.6063 Remote Similarity NPD7260 Phase 2
0.6058 Remote Similarity NPD1695 Approved
0.6058 Remote Similarity NPD4753 Phase 2
0.6055 Remote Similarity NPD7638 Approved
0.605 Remote Similarity NPD6317 Approved
0.6048 Remote Similarity NPD7507 Approved
0.604 Remote Similarity NPD4786 Approved
0.6036 Remote Similarity NPD5224 Approved
0.6036 Remote Similarity NPD5226 Approved
0.6036 Remote Similarity NPD4633 Approved
0.6036 Remote Similarity NPD5225 Approved
0.6033 Remote Similarity NPD7299 Clinical (unspecified phase)
0.6019 Remote Similarity NPD7524 Approved
0.6016 Remote Similarity NPD7604 Phase 2
0.6 Remote Similarity NPD6313 Approved
0.6 Remote Similarity NPD6314 Approved
0.6 Remote Similarity NPD6335 Approved
0.6 Remote Similarity NPD4700 Approved
0.5984 Remote Similarity NPD6291 Clinical (unspecified phase)
0.5982 Remote Similarity NPD5175 Approved
0.5982 Remote Similarity NPD5174 Approved
0.5981 Remote Similarity NPD7900 Approved
0.5981 Remote Similarity NPD7901 Clinical (unspecified phase)
0.5968 Remote Similarity NPD7492 Approved
0.5966 Remote Similarity NPD6868 Approved
0.5965 Remote Similarity NPD5954 Clinical (unspecified phase)
0.595 Remote Similarity NPD7100 Approved
0.595 Remote Similarity NPD7101 Approved
0.5948 Remote Similarity NPD4634 Approved
0.5943 Remote Similarity NPD5693 Phase 1
0.5926 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5922 Remote Similarity NPD3574 Clinical (unspecified phase)
0.592 Remote Similarity NPD6336 Discontinued

Structure

External Identifiers

PubChem CID   72704486
ChEMBL   CHEMBL2431881
ZINC  

Physicochemical Properties

Molecular Weight:  378.20
ALogP:  0.7677
MLogP:  3.11
XLogP:  1.827
# Rotatable Bonds:  14
Polar Surface Area:  104.06
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  27

Download Data

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