Natural Product: NPC109376

Natural Product ID:  NPC109376
Common Name:   Argutin A
IUPAC Name:   [(1S,3R,5R,6aS,7R,8R,10R,10aS)-1,3-diacetyloxy-10-hydroxy-7,8-dimethyl-7-[(2E)-3-methylpenta-2,4-dienyl]-1,3,5,6,6a,8,9,10-octahydrobenzo[d][2]benzofuran-5-yl] (2Z,4E)-deca-2,4-dienoate
Synonyms:   Argutin A
Molecular Formula:   C34H48O8
Standard InCHIKey:  STQXAQGQWCMXAF-XMESWUDMSA-N
Standard InCHI:  InChI=1S/C34H48O8/c1-8-10-11-12-13-14-15-16-30(38)41-26-20-27-31(39-24(5)35)42-32(40-25(6)36)34(27)28(21-26)33(7,18-17-22(3)9-2)23(4)19-29(34)37/h9,13-17,20,23,26,28-29,31-32,37H,2,8,10-12,18-19,21H2,1,3-7H3/b14-13+,16-15-,22-17+/t23-,26+,28+,29-,31+,32-,33-,34-/m1/s1
Canonical SMILES:  CCCCC/C=C/C=CC(=O)O[C@H]1C=C2[C@@H](OC(=O)C)O[C@H]([C@]32[C@@H](C1)[C@](C)(C/C=C(/C=C)C)[C@@H](C[C@H]3O)C)OC(=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
NPO22840 Casearia arguta Species Salicaceae Eukaryota PMID[21067210]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT369 Cell Line ACHN Homo sapiens Ratio EC50 = 2.3 229223
NPT369 Cell Line ACHN Homo sapiens EC50 = 2400 nM 21376582
NPT369 Cell Line ACHN Homo sapiens EC50 = 5400 nM PubChem BioAssay data set

  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 NPC109376 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
0.9899 High Similarity NPC470024
0.9899 High Similarity NPC224660
0.9898 High Similarity NPC172867
0.9703 High Similarity NPC316708
0.9608 High Similarity NPC17791
0.9608 High Similarity NPC470026
0.9515 High Similarity NPC317460
0.9515 High Similarity NPC328074
0.9515 High Similarity NPC321272
0.9515 High Similarity NPC470025
0.95 High Similarity NPC218158
0.9423 High Similarity NPC470027
0.94 High Similarity NPC264867
0.94 High Similarity NPC201880
0.94 High Similarity NPC470321
0.94 High Similarity NPC81567
0.94 High Similarity NPC473207
0.93 High Similarity NPC475889
0.93 High Similarity NPC134270
0.93 High Similarity NPC7613
0.93 High Similarity NPC7644
0.93 High Similarity NPC127933
0.9216 High Similarity NPC184512
0.92 High Similarity NPC238397
0.92 High Similarity NPC471363
0.9126 High Similarity NPC311223
0.9118 High Similarity NPC252296
0.9082 High Similarity NPC171598
0.9038 High Similarity NPC316974
0.9038 High Similarity NPC40728
0.9029 High Similarity NPC125423
0.9029 High Similarity NPC88013
0.9 High Similarity NPC473545
0.9 High Similarity NPC472187
0.9 High Similarity NPC473204
0.899 High Similarity NPC98112
0.898 High Similarity NPC471372
0.898 High Similarity NPC471362
0.898 High Similarity NPC472189
0.8952 High Similarity NPC119550
0.8942 High Similarity NPC135015
0.8942 High Similarity NPC48548
0.8942 High Similarity NPC217921
0.8942 High Similarity NPC128795
0.89 High Similarity NPC472186
0.89 High Similarity NPC476800
0.89 High Similarity NPC318917
0.89 High Similarity NPC471366
0.88 High Similarity NPC472188
0.8738 High Similarity NPC120009
0.8713 High Similarity NPC474440
0.8667 High Similarity NPC475074
0.8627 High Similarity NPC477972
0.8627 High Similarity NPC20113
0.8627 High Similarity NPC477968
0.8627 High Similarity NPC161527
0.8627 High Similarity NPC219285
0.8627 High Similarity NPC477971
0.8627 High Similarity NPC228251
0.8571 High Similarity NPC82251
0.8558 High Similarity NPC45897
0.8529 High Similarity NPC473154
0.8505 High Similarity NPC206618
0.85 High Similarity NPC88507
0.8482 Intermediate Similarity NPC470914
0.8469 Intermediate Similarity NPC470819
0.8447 Intermediate Similarity NPC324841
0.8426 Intermediate Similarity NPC177047
0.8421 Intermediate Similarity NPC471082
0.8411 Intermediate Similarity NPC38948
0.8396 Intermediate Similarity NPC239961
0.8393 Intermediate Similarity NPC473828
0.8393 Intermediate Similarity NPC473617
0.8384 Intermediate Similarity NPC470817
0.8384 Intermediate Similarity NPC469403
0.8365 Intermediate Similarity NPC198992
0.8364 Intermediate Similarity NPC473159
0.8364 Intermediate Similarity NPC157441
0.8364 Intermediate Similarity NPC264153
0.8333 Intermediate Similarity NPC311166
0.8333 Intermediate Similarity NPC94905
0.8333 Intermediate Similarity NPC165632
0.8333 Intermediate Similarity NPC8954
0.8318 Intermediate Similarity NPC472390
0.8317 Intermediate Similarity NPC470255
0.8302 Intermediate Similarity NPC470768
0.8286 Intermediate Similarity NPC11956
0.8273 Intermediate Similarity NPC473125
0.8273 Intermediate Similarity NPC194951
0.8273 Intermediate Similarity NPC12046
0.8246 Intermediate Similarity NPC257610
0.8235 Intermediate Similarity NPC13924
0.8235 Intermediate Similarity NPC100892
0.8235 Intermediate Similarity NPC477969
0.8235 Intermediate Similarity NPC276110
0.8235 Intermediate Similarity NPC135224
0.8235 Intermediate Similarity NPC477970
0.8224 Intermediate Similarity NPC470763
0.8224 Intermediate Similarity NPC470767
0.8218 Intermediate Similarity NPC162615
0.8218 Intermediate Similarity NPC472812
0.8218 Intermediate Similarity NPC205034
0.8218 Intermediate Similarity NPC152778
0.8214 Intermediate Similarity NPC207637
0.8208 Intermediate Similarity NPC471888
0.8208 Intermediate Similarity NPC471365
0.8208 Intermediate Similarity NPC471886
0.8208 Intermediate Similarity NPC471364
0.8208 Intermediate Similarity NPC471450
0.8208 Intermediate Similarity NPC281378
0.8208 Intermediate Similarity NPC471885
0.8208 Intermediate Similarity NPC23584
0.8208 Intermediate Similarity NPC471887
0.8208 Intermediate Similarity NPC132395
0.8198 Intermediate Similarity NPC44298
0.8198 Intermediate Similarity NPC290608
0.8198 Intermediate Similarity NPC473128
0.8198 Intermediate Similarity NPC40133
0.8198 Intermediate Similarity NPC49413
0.819 Intermediate Similarity NPC477717
0.819 Intermediate Similarity NPC472554
0.819 Intermediate Similarity NPC280991
0.8182 Intermediate Similarity NPC263079
0.8174 Intermediate Similarity NPC476204
0.8174 Intermediate Similarity NPC170084
0.8173 Intermediate Similarity NPC278673
0.8167 Intermediate Similarity NPC230331
0.8155 Intermediate Similarity NPC16967
0.8142 Intermediate Similarity NPC23046
0.8142 Intermediate Similarity NPC203862
0.8137 Intermediate Similarity NPC298973
0.8137 Intermediate Similarity NPC104925
0.8137 Intermediate Similarity NPC105490
0.8137 Intermediate Similarity NPC469491
0.8137 Intermediate Similarity NPC189513
0.8125 Intermediate Similarity NPC475163
0.8119 Intermediate Similarity NPC472811
0.8113 Intermediate Similarity NPC472552
0.8113 Intermediate Similarity NPC470571
0.8113 Intermediate Similarity NPC31058
0.8113 Intermediate Similarity NPC37207
0.8113 Intermediate Similarity NPC121423
0.8113 Intermediate Similarity NPC471889
0.8113 Intermediate Similarity NPC469606
0.8113 Intermediate Similarity NPC472815
0.8113 Intermediate Similarity NPC475038
0.8113 Intermediate Similarity NPC475344
0.8113 Intermediate Similarity NPC109195
0.8113 Intermediate Similarity NPC201191
0.8113 Intermediate Similarity NPC273005
0.8113 Intermediate Similarity NPC150463
0.8113 Intermediate Similarity NPC476471
0.8108 Intermediate Similarity NPC231797
0.81 Intermediate Similarity NPC470734
0.81 Intermediate Similarity NPC261320
0.8095 Intermediate Similarity NPC477721
0.8095 Intermediate Similarity NPC477716
0.8087 Intermediate Similarity NPC135369
0.8087 Intermediate Similarity NPC48692
0.8077 Intermediate Similarity NPC125551
0.8077 Intermediate Similarity NPC91197
0.8077 Intermediate Similarity NPC96597
0.8077 Intermediate Similarity NPC309503
0.8077 Intermediate Similarity NPC155319
0.8077 Intermediate Similarity NPC239547
0.8073 Intermediate Similarity NPC475263
0.807 Intermediate Similarity NPC470515
0.8058 Intermediate Similarity NPC286612
0.8058 Intermediate Similarity NPC230347
0.8058 Intermediate Similarity NPC275310
0.8056 Intermediate Similarity NPC469607
0.8056 Intermediate Similarity NPC51719
0.8051 Intermediate Similarity NPC179261
0.8039 Intermediate Similarity NPC7349
0.8037 Intermediate Similarity NPC474124
0.8037 Intermediate Similarity NPC474575
0.8037 Intermediate Similarity NPC85742
0.8036 Intermediate Similarity NPC287075
0.8034 Intermediate Similarity NPC41129
0.802 Intermediate Similarity NPC471371
0.802 Intermediate Similarity NPC471370
0.802 Intermediate Similarity NPC310479
0.802 Intermediate Similarity NPC220216
0.802 Intermediate Similarity NPC78973
0.8019 Intermediate Similarity NPC11974
0.8018 Intermediate Similarity NPC208189
0.8018 Intermediate Similarity NPC65034
0.8017 Intermediate Similarity NPC233500
0.8 Intermediate Similarity NPC219656
0.8 Intermediate Similarity NPC216478
0.8 Intermediate Similarity NPC304260
0.8 Intermediate Similarity NPC29639
0.8 Intermediate Similarity NPC5883
0.8 Intermediate Similarity NPC470517
0.8 Intermediate Similarity NPC268326
0.8 Intermediate Similarity NPC470911
0.8 Intermediate Similarity NPC112457
0.8 Intermediate Similarity NPC44899
0.8 Intermediate Similarity NPC470915
0.8 Intermediate Similarity NPC475586

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC109376 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
0.8174 Intermediate Similarity NPD7503 Approved
0.7909 Intermediate Similarity NPD6686 Approved
0.7863 Intermediate Similarity NPD8033 Approved
0.7778 Intermediate Similarity NPD8294 Approved
0.7778 Intermediate Similarity NPD8377 Approved
0.7759 Intermediate Similarity NPD7327 Approved
0.7759 Intermediate Similarity NPD7328 Approved
0.7712 Intermediate Similarity NPD8380 Approved
0.7712 Intermediate Similarity NPD8335 Approved
0.7712 Intermediate Similarity NPD8378 Approved
0.7712 Intermediate Similarity NPD8379 Approved
0.7712 Intermediate Similarity NPD8296 Approved
0.7692 Intermediate Similarity NPD7516 Approved
0.7664 Intermediate Similarity NPD7638 Approved
0.7593 Intermediate Similarity NPD7639 Approved
0.7593 Intermediate Similarity NPD7640 Approved
0.75 Intermediate Similarity NPD7838 Discovery
0.75 Intermediate Similarity NPD4225 Approved
0.75 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7431 Intermediate Similarity NPD6648 Approved
0.7426 Intermediate Similarity NPD6400 Clinical (unspecified phase)
0.7417 Intermediate Similarity NPD8515 Approved
0.7417 Intermediate Similarity NPD8513 Phase 3
0.7417 Intermediate Similarity NPD8516 Approved
0.7417 Intermediate Similarity NPD8517 Approved
0.7364 Intermediate Similarity NPD5344 Discontinued
0.7317 Intermediate Similarity NPD7507 Approved
0.72 Intermediate Similarity NPD7736 Approved
0.7179 Intermediate Similarity NPD6882 Approved
0.7143 Intermediate Similarity NPD7319 Approved
0.7073 Intermediate Similarity NPD6370 Approved
0.7069 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7043 Intermediate Similarity NPD6412 Phase 2
0.7016 Intermediate Similarity NPD8328 Phase 3
0.6991 Remote Similarity NPD7632 Discontinued
0.6984 Remote Similarity NPD8293 Discontinued
0.6975 Remote Similarity NPD8133 Approved
0.696 Remote Similarity NPD7492 Approved
0.6944 Remote Similarity NPD7637 Suspended
0.6942 Remote Similarity NPD7115 Discovery
0.6923 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6911 Remote Similarity NPD6054 Approved
0.6905 Remote Similarity NPD6616 Approved
0.6891 Remote Similarity NPD8297 Approved
0.6881 Remote Similarity NPD5778 Approved
0.6881 Remote Similarity NPD5779 Approved
0.6864 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6857 Remote Similarity NPD1694 Approved
0.685 Remote Similarity NPD8074 Phase 3
0.685 Remote Similarity NPD7078 Approved
0.6838 Remote Similarity NPD6881 Approved
0.6838 Remote Similarity NPD6899 Approved
0.6818 Remote Similarity NPD7748 Approved
0.6807 Remote Similarity NPD6649 Approved
0.6807 Remote Similarity NPD6650 Approved
0.6807 Remote Similarity NPD8130 Phase 1
0.6803 Remote Similarity NPD6009 Approved
0.6803 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6786 Remote Similarity NPD7902 Approved
0.6762 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6752 Remote Similarity NPD5697 Approved
0.6723 Remote Similarity NPD7102 Approved
0.6723 Remote Similarity NPD7290 Approved
0.6723 Remote Similarity NPD6883 Approved
0.672 Remote Similarity NPD6015 Approved
0.672 Remote Similarity NPD6016 Approved
0.67 Remote Similarity NPD8264 Approved
0.6697 Remote Similarity NPD46 Approved
0.6697 Remote Similarity NPD6698 Approved
0.6667 Remote Similarity NPD6675 Approved
0.6667 Remote Similarity NPD5739 Approved
0.6667 Remote Similarity NPD5988 Approved
0.6667 Remote Similarity NPD6869 Approved
0.6667 Remote Similarity NPD6847 Approved
0.6667 Remote Similarity NPD6402 Approved
0.6667 Remote Similarity NPD8413 Clinical (unspecified phase)
0.6667 Remote Similarity NPD7128 Approved
0.6667 Remote Similarity NPD6695 Phase 3
0.6667 Remote Similarity NPD6617 Approved
0.664 Remote Similarity NPD6059 Approved
0.664 Remote Similarity NPD6319 Approved
0.6639 Remote Similarity NPD6013 Approved
0.6639 Remote Similarity NPD6014 Approved
0.6639 Remote Similarity NPD6012 Approved
0.6639 Remote Similarity NPD6373 Approved
0.6639 Remote Similarity NPD6372 Approved
0.6636 Remote Similarity NPD7515 Phase 2
0.6636 Remote Similarity NPD6411 Approved
0.6614 Remote Similarity NPD6067 Discontinued
0.6612 Remote Similarity NPD6053 Discontinued
0.661 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6577 Remote Similarity NPD6399 Phase 3
0.6574 Remote Similarity NPD7750 Discontinued
0.6571 Remote Similarity NPD4752 Clinical (unspecified phase)
0.6557 Remote Similarity NPD4632 Approved
0.6555 Remote Similarity NPD6011 Approved
0.6555 Remote Similarity NPD7320 Approved
0.6525 Remote Similarity NPD6008 Approved
0.6518 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6518 Remote Similarity NPD7900 Approved
0.6515 Remote Similarity NPD7260 Phase 2
0.6486 Remote Similarity NPD7983 Approved
0.6486 Remote Similarity NPD6079 Approved
0.6484 Remote Similarity NPD7830 Approved
0.6484 Remote Similarity NPD7829 Approved
0.6471 Remote Similarity NPD5701 Approved
0.6471 Remote Similarity NPD7899 Clinical (unspecified phase)
0.646 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6455 Remote Similarity NPD6051 Approved
0.6455 Remote Similarity NPD6101 Approved
0.6455 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6442 Remote Similarity NPD7645 Phase 2
0.6442 Remote Similarity NPD6929 Approved
0.6422 Remote Similarity NPD7524 Approved
0.641 Remote Similarity NPD5211 Phase 2
0.6404 Remote Similarity NPD7839 Suspended
0.6381 Remote Similarity NPD7514 Phase 3
0.6381 Remote Similarity NPD7525 Registered
0.6381 Remote Similarity NPD6930 Phase 2
0.6381 Remote Similarity NPD7332 Phase 2
0.6381 Remote Similarity NPD6931 Approved
0.6379 Remote Similarity NPD5285 Approved
0.6379 Remote Similarity NPD5286 Approved
0.6379 Remote Similarity NPD4696 Approved
0.6357 Remote Similarity NPD7604 Phase 2
0.6348 Remote Similarity NPD6083 Phase 2
0.6348 Remote Similarity NPD6084 Phase 2
0.6346 Remote Similarity NPD7145 Approved
0.633 Remote Similarity NPD3618 Phase 1
0.6328 Remote Similarity NPD5983 Phase 2
0.6321 Remote Similarity NPD6902 Approved
0.6311 Remote Similarity NPD6371 Approved
0.6306 Remote Similarity NPD5328 Approved
0.6303 Remote Similarity NPD5141 Approved
0.6299 Remote Similarity NPD7100 Approved
0.6299 Remote Similarity NPD7101 Approved
0.6281 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6277 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6273 Remote Similarity NPD4250 Approved
0.6273 Remote Similarity NPD4251 Approved
0.6271 Remote Similarity NPD5225 Approved
0.6271 Remote Similarity NPD4633 Approved
0.6271 Remote Similarity NPD5226 Approved
0.6271 Remote Similarity NPD5224 Approved
0.6261 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6261 Remote Similarity NPD5222 Approved
0.6261 Remote Similarity NPD5221 Approved
0.626 Remote Similarity NPD6336 Discontinued
0.626 Remote Similarity NPD6401 Clinical (unspecified phase)
0.625 Remote Similarity NPD5776 Phase 2
0.625 Remote Similarity NPD6932 Approved
0.625 Remote Similarity NPD6925 Approved
0.625 Remote Similarity NPD5785 Approved
0.6242 Remote Similarity NPD7799 Discontinued
0.6226 Remote Similarity NPD8259 Clinical (unspecified phase)
0.6224 Remote Similarity NPD7625 Phase 1
0.6222 Remote Similarity NPD6845 Suspended
0.622 Remote Similarity NPD6335 Approved
0.6218 Remote Similarity NPD5175 Approved
0.6218 Remote Similarity NPD5174 Approved
0.6214 Remote Similarity NPD6942 Approved
0.6214 Remote Similarity NPD8039 Approved
0.6214 Remote Similarity NPD7339 Approved
0.6207 Remote Similarity NPD5173 Approved
0.6207 Remote Similarity NPD4755 Approved
0.6195 Remote Similarity NPD5281 Approved
0.6195 Remote Similarity NPD8035 Phase 2
0.6195 Remote Similarity NPD8034 Phase 2
0.6195 Remote Similarity NPD5284 Approved
0.6195 Remote Similarity NPD7087 Discontinued
0.619 Remote Similarity NPD6274 Approved
0.619 Remote Similarity NPD6868 Approved
0.6186 Remote Similarity NPD5223 Approved
0.6182 Remote Similarity NPD6409 Approved
0.6182 Remote Similarity NPD5330 Approved
0.6182 Remote Similarity NPD6684 Approved
0.6182 Remote Similarity NPD7334 Approved
0.6182 Remote Similarity NPD4249 Approved
0.6182 Remote Similarity NPD7146 Approved
0.6182 Remote Similarity NPD7521 Approved
0.6179 Remote Similarity NPD4634 Approved
0.6174 Remote Similarity NPD5695 Phase 3
0.6165 Remote Similarity NPD6033 Approved
0.6154 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6148 Remote Similarity NPD4730 Approved
0.6148 Remote Similarity NPD4729 Approved
0.6147 Remote Similarity NPD4786 Approved
0.6142 Remote Similarity NPD6317 Approved
0.614 Remote Similarity NPD4202 Approved
0.6136 Remote Similarity NPD8451 Approved
0.6126 Remote Similarity NPD3573 Approved
0.6126 Remote Similarity NPD4751 Clinical (unspecified phase)
0.6117 Remote Similarity NPD6926 Approved
0.6117 Remote Similarity NPD6924 Approved
0.6111 Remote Similarity NPD5209 Approved
0.6111 Remote Similarity NPD3667 Approved
0.6102 Remote Similarity NPD4700 Approved
0.6094 Remote Similarity NPD7641 Discontinued
0.6094 Remote Similarity NPD6313 Approved
0.6094 Remote Similarity NPD6314 Approved

Structure

External Identifiers

PubChem CID   53322249
ChEMBL   CHEMBL1651112
ZINC  

Physicochemical Properties

Molecular Weight:  584.33
ALogP:  2.1987
MLogP:  4.32
XLogP:  8.293
# Rotatable Bonds:  22
Polar Surface Area:  108.36
# H-Bond Aceptor:  8
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  42

Download Data

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