Natural Product: NPC218853

Natural Product ID:  NPC218853
Common Name:   Polystanin A
IUPAC Name:   methyl (3S)-3-[(3S,3aS,5aR,6S,7S,9R,9aR)-3-[(3S,5R,6S)-5,6-dihydroxy-6-(2-hydroxypropan-2-yl)oxan-3-yl]-9-hydroxy-3a,6,9a-trimethyl-7-prop-1-en-2-yl-2,3,4,5,5a,7,8,9-octahydrocyclopenta[a]naphthalen-6-yl]-3-acetyloxypropanoate
Synonyms:  
Molecular Formula:   C33H52O9
Standard InCHIKey:  DVQXYBYHXZHGRQ-KAYXFQKTSA-N
Standard InCHI:  InChI=1S/C33H52O9/c1-18(2)22-15-25(35)32(8)23-11-10-21(20-14-26(36)33(39,41-17-20)29(4,5)38)30(23,6)13-12-24(32)31(22,7)27(42-19(3)34)16-28(37)40-9/h11,20-22,24-27,35-36,38-39H,1,10,12-17H2,2-9H3/t20-,21+,22+,24-,25-,26-,27+,30+,31+,32+,33+/m1/s1
Canonical SMILES:  COC(=O)C[C@@H]([C@@]1(C)[C@@H](C[C@H]([C@@]2([C@@H]1CC[C@@]1(C2=CC[C@H]1[C@H]1CO[C@]([C@@H](C1)O)(O)C(O)(C)C)C)C)O)C(=C)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
NPO3063 Aphanamixis grandifolia Species Meliaceae Eukaryota Fruits PMID[23772699]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT65 Cell Line HepG2 Homo sapiens IC50 = 3620 nM 21146414
NPT181 Cell Line Bel-7402 Homo sapiens IC50 = 1530 nM 21146414
NPT659 Cell Line SMMC-7721 Homo sapiens IC50 = 670 nM DailyMed
NPT116 Cell Line HL-60 Homo sapiens IC50 = 1800 nM 25800514

  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 NPC218853 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
0.9706 High Similarity NPC250956
0.902 High Similarity NPC470053
0.8952 High Similarity NPC258323
0.8942 High Similarity NPC472655
0.8922 High Similarity NPC470054
0.8879 High Similarity NPC250481
0.8879 High Similarity NPC285410
0.8879 High Similarity NPC263827
0.8807 High Similarity NPC473882
0.8807 High Similarity NPC116024
0.8785 High Similarity NPC52241
0.8785 High Similarity NPC101450
0.8785 High Similarity NPC475317
0.8785 High Similarity NPC154856
0.8785 High Similarity NPC129340
0.8774 High Similarity NPC295389
0.8739 High Similarity NPC239293
0.8725 High Similarity NPC470068
0.8716 High Similarity NPC251309
0.8716 High Similarity NPC255017
0.8704 High Similarity NPC272242
0.8704 High Similarity NPC31839
0.8692 High Similarity NPC477069
0.8692 High Similarity NPC477070
0.8692 High Similarity NPC265655
0.8679 High Similarity NPC293512
0.8641 High Similarity NPC167974
0.8636 High Similarity NPC472274
0.8624 High Similarity NPC46388
0.8624 High Similarity NPC210420
0.8624 High Similarity NPC233003
0.8624 High Similarity NPC130427
0.8624 High Similarity NPC48249
0.8624 High Similarity NPC37739
0.8624 High Similarity NPC80843
0.8624 High Similarity NPC474265
0.8624 High Similarity NPC1046
0.8611 High Similarity NPC475563
0.8611 High Similarity NPC242611
0.8611 High Similarity NPC475134
0.8611 High Similarity NPC274507
0.8598 High Similarity NPC195708
0.8598 High Similarity NPC472218
0.8598 High Similarity NPC472217
0.8598 High Similarity NPC472219
0.8585 High Similarity NPC473199
0.8584 High Similarity NPC471406
0.8571 High Similarity NPC297179
0.8559 High Similarity NPC244127
0.8545 High Similarity NPC238935
0.8545 High Similarity NPC271138
0.8545 High Similarity NPC138334
0.8545 High Similarity NPC47063
0.8545 High Similarity NPC102619
0.8545 High Similarity NPC204458
0.8545 High Similarity NPC189884
0.8545 High Similarity NPC269315
0.8545 High Similarity NPC475208
0.8544 High Similarity NPC470066
0.8544 High Similarity NPC119036
0.8544 High Similarity NPC470067
0.8532 High Similarity NPC473481
0.8532 High Similarity NPC297208
0.8532 High Similarity NPC235841
0.8532 High Similarity NPC473921
0.8532 High Similarity NPC292196
0.8532 High Similarity NPC30397
0.8532 High Similarity NPC108748
0.8532 High Similarity NPC211798
0.8532 High Similarity NPC191763
0.8532 High Similarity NPC475668
0.8532 High Similarity NPC477073
0.8532 High Similarity NPC475480
0.8532 High Similarity NPC11035
0.8519 High Similarity NPC137917
0.8519 High Similarity NPC167383
0.8519 High Similarity NPC57362
0.8519 High Similarity NPC284828
0.8519 High Similarity NPC173905
0.8519 High Similarity NPC5475
0.8519 High Similarity NPC237503
0.8519 High Similarity NPC204407
0.8519 High Similarity NPC118225
0.8519 High Similarity NPC472216
0.8519 High Similarity NPC306746
0.8496 Intermediate Similarity NPC477071
0.8491 Intermediate Similarity NPC470061
0.8491 Intermediate Similarity NPC470058
0.8491 Intermediate Similarity NPC470059
0.8491 Intermediate Similarity NPC470043
0.8491 Intermediate Similarity NPC470064
0.8491 Intermediate Similarity NPC470057
0.8491 Intermediate Similarity NPC470060
0.8491 Intermediate Similarity NPC475036
0.8491 Intermediate Similarity NPC470062
0.8476 Intermediate Similarity NPC473788
0.8476 Intermediate Similarity NPC475558
0.8468 Intermediate Similarity NPC220293
0.8468 Intermediate Similarity NPC164389
0.8468 Intermediate Similarity NPC474557
0.8468 Intermediate Similarity NPC243354
0.8468 Intermediate Similarity NPC475486
0.8455 Intermediate Similarity NPC234042
0.8455 Intermediate Similarity NPC152117
0.8455 Intermediate Similarity NPC128925
0.8455 Intermediate Similarity NPC470543
0.8455 Intermediate Similarity NPC256798
0.8455 Intermediate Similarity NPC243572
0.8455 Intermediate Similarity NPC470063
0.8455 Intermediate Similarity NPC100383
0.8455 Intermediate Similarity NPC116794
0.844 Intermediate Similarity NPC56713
0.844 Intermediate Similarity NPC470065
0.844 Intermediate Similarity NPC476887
0.844 Intermediate Similarity NPC279554
0.844 Intermediate Similarity NPC75747
0.844 Intermediate Similarity NPC476882
0.844 Intermediate Similarity NPC108709
0.844 Intermediate Similarity NPC476881
0.844 Intermediate Similarity NPC127056
0.844 Intermediate Similarity NPC474589
0.844 Intermediate Similarity NPC476884
0.844 Intermediate Similarity NPC199457
0.844 Intermediate Similarity NPC476880
0.844 Intermediate Similarity NPC164194
0.844 Intermediate Similarity NPC475243
0.844 Intermediate Similarity NPC102914
0.844 Intermediate Similarity NPC78046
0.844 Intermediate Similarity NPC59804
0.844 Intermediate Similarity NPC476886
0.844 Intermediate Similarity NPC476883
0.844 Intermediate Similarity NPC269095
0.844 Intermediate Similarity NPC7870
0.844 Intermediate Similarity NPC220984
0.844 Intermediate Similarity NPC68419
0.844 Intermediate Similarity NPC29069
0.844 Intermediate Similarity NPC110139
0.844 Intermediate Similarity NPC90630
0.844 Intermediate Similarity NPC174679
0.844 Intermediate Similarity NPC476885
0.844 Intermediate Similarity NPC90856
0.844 Intermediate Similarity NPC270667
0.844 Intermediate Similarity NPC136877
0.844 Intermediate Similarity NPC474567
0.844 Intermediate Similarity NPC475296
0.8435 Intermediate Similarity NPC156789
0.8431 Intermediate Similarity NPC30677
0.8431 Intermediate Similarity NPC279974
0.8431 Intermediate Similarity NPC180557
0.8431 Intermediate Similarity NPC469329
0.8431 Intermediate Similarity NPC473415
0.8431 Intermediate Similarity NPC37787
0.8426 Intermediate Similarity NPC469845
0.8426 Intermediate Similarity NPC472988
0.8426 Intermediate Similarity NPC28198
0.8426 Intermediate Similarity NPC284807
0.8426 Intermediate Similarity NPC177246
0.8426 Intermediate Similarity NPC476123
0.8426 Intermediate Similarity NPC224414
0.8426 Intermediate Similarity NPC88744
0.8426 Intermediate Similarity NPC38217
0.8421 Intermediate Similarity NPC142151
0.8421 Intermediate Similarity NPC473645
0.8421 Intermediate Similarity NPC153673
0.8421 Intermediate Similarity NPC144644
0.8421 Intermediate Similarity NPC37860
0.8421 Intermediate Similarity NPC110385
0.8421 Intermediate Similarity NPC267694
0.8411 Intermediate Similarity NPC475494
0.8411 Intermediate Similarity NPC477877
0.8411 Intermediate Similarity NPC470587
0.8407 Intermediate Similarity NPC232237
0.8407 Intermediate Similarity NPC86020
0.8407 Intermediate Similarity NPC188667
0.8407 Intermediate Similarity NPC204552
0.8407 Intermediate Similarity NPC105800
0.8407 Intermediate Similarity NPC475632
0.8396 Intermediate Similarity NPC218513
0.8396 Intermediate Similarity NPC55954
0.8393 Intermediate Similarity NPC26626
0.8393 Intermediate Similarity NPC279638
0.8393 Intermediate Similarity NPC51465
0.8393 Intermediate Similarity NPC470628
0.8393 Intermediate Similarity NPC259306
0.8393 Intermediate Similarity NPC235539
0.8393 Intermediate Similarity NPC134869
0.8393 Intermediate Similarity NPC75287
0.8393 Intermediate Similarity NPC58448
0.8393 Intermediate Similarity NPC37134
0.8393 Intermediate Similarity NPC288205
0.8393 Intermediate Similarity NPC305267
0.8393 Intermediate Similarity NPC476992
0.8393 Intermediate Similarity NPC160415
0.8393 Intermediate Similarity NPC291903
0.8393 Intermediate Similarity NPC474046
0.8393 Intermediate Similarity NPC152199
0.8378 Intermediate Similarity NPC146563
0.8378 Intermediate Similarity NPC194273
0.8378 Intermediate Similarity NPC124296
0.8378 Intermediate Similarity NPC260665

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC218853 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
0.8018 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.8017 Intermediate Similarity NPD7319 Approved
0.8 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7949 Intermediate Similarity NPD6319 Approved
0.7928 Intermediate Similarity NPD6686 Approved
0.7917 Intermediate Similarity NPD7507 Approved
0.7899 Intermediate Similarity NPD8328 Phase 3
0.7895 Intermediate Similarity NPD8133 Approved
0.7851 Intermediate Similarity NPD8293 Discontinued
0.7838 Intermediate Similarity NPD6412 Phase 2
0.7833 Intermediate Similarity NPD7492 Approved
0.7807 Intermediate Similarity NPD8297 Approved
0.7797 Intermediate Similarity NPD6054 Approved
0.7797 Intermediate Similarity NPD6059 Approved
0.7787 Intermediate Similarity NPD7736 Approved
0.7769 Intermediate Similarity NPD6616 Approved
0.7731 Intermediate Similarity NPD8033 Approved
0.7714 Intermediate Similarity NPD6399 Phase 3
0.7705 Intermediate Similarity NPD7078 Approved
0.7692 Intermediate Similarity NPD7115 Discovery
0.7667 Intermediate Similarity NPD6370 Approved
0.7652 Intermediate Similarity NPD6882 Approved
0.7647 Intermediate Similarity NPD8377 Approved
0.7647 Intermediate Similarity NPD8294 Approved
0.7627 Intermediate Similarity NPD7327 Approved
0.7627 Intermediate Similarity NPD7328 Approved
0.7611 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7589 Intermediate Similarity NPD6402 Approved
0.7589 Intermediate Similarity NPD5739 Approved
0.7589 Intermediate Similarity NPD6675 Approved
0.7589 Intermediate Similarity NPD7128 Approved
0.7586 Intermediate Similarity NPD4632 Approved
0.7583 Intermediate Similarity NPD6015 Approved
0.7583 Intermediate Similarity NPD8335 Approved
0.7583 Intermediate Similarity NPD6016 Approved
0.7583 Intermediate Similarity NPD8378 Approved
0.7583 Intermediate Similarity NPD8380 Approved
0.7583 Intermediate Similarity NPD8296 Approved
0.7583 Intermediate Similarity NPD8379 Approved
0.7563 Intermediate Similarity NPD7516 Approved
0.7544 Intermediate Similarity NPD6372 Approved
0.7544 Intermediate Similarity NPD6373 Approved
0.7542 Intermediate Similarity NPD6009 Approved
0.7523 Intermediate Similarity NPD7638 Approved
0.7521 Intermediate Similarity NPD5988 Approved
0.7456 Intermediate Similarity NPD7320 Approved
0.7456 Intermediate Similarity NPD6899 Approved
0.7456 Intermediate Similarity NPD6881 Approved
0.7455 Intermediate Similarity NPD7640 Approved
0.7455 Intermediate Similarity NPD7639 Approved
0.7453 Intermediate Similarity NPD8035 Phase 2
0.7453 Intermediate Similarity NPD8034 Phase 2
0.7438 Intermediate Similarity NPD8513 Phase 3
0.7438 Intermediate Similarity NPD8516 Approved
0.7438 Intermediate Similarity NPD8517 Approved
0.7438 Intermediate Similarity NPD8515 Approved
0.7414 Intermediate Similarity NPD8130 Phase 1
0.7414 Intermediate Similarity NPD6650 Approved
0.7414 Intermediate Similarity NPD6649 Approved
0.7391 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD5701 Approved
0.7368 Intermediate Similarity NPD5697 Approved
0.7364 Intermediate Similarity NPD4225 Approved
0.7328 Intermediate Similarity NPD7102 Approved
0.7328 Intermediate Similarity NPD4634 Approved
0.7328 Intermediate Similarity NPD7290 Approved
0.7328 Intermediate Similarity NPD6883 Approved
0.7315 Intermediate Similarity NPD7748 Approved
0.7295 Intermediate Similarity NPD7503 Approved
0.729 Intermediate Similarity NPD6411 Approved
0.7282 Intermediate Similarity NPD4786 Approved
0.7281 Intermediate Similarity NPD6008 Approved
0.7273 Intermediate Similarity NPD6084 Phase 2
0.7273 Intermediate Similarity NPD7902 Approved
0.7273 Intermediate Similarity NPD6083 Phase 2
0.7265 Intermediate Similarity NPD6869 Approved
0.7265 Intermediate Similarity NPD6847 Approved
0.7265 Intermediate Similarity NPD6617 Approved
0.7241 Intermediate Similarity NPD6014 Approved
0.7241 Intermediate Similarity NPD6013 Approved
0.7241 Intermediate Similarity NPD6012 Approved
0.7222 Intermediate Similarity NPD6033 Approved
0.7212 Intermediate Similarity NPD7520 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7177 Intermediate Similarity NPD7604 Phase 2
0.7155 Intermediate Similarity NPD6011 Approved
0.7154 Intermediate Similarity NPD5983 Phase 2
0.7143 Intermediate Similarity NPD8074 Phase 3
0.713 Intermediate Similarity NPD7515 Phase 2
0.713 Intermediate Similarity NPD7983 Approved
0.713 Intermediate Similarity NPD7637 Suspended
0.7119 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7119 Intermediate Similarity NPD6401 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD4755 Approved
0.7103 Intermediate Similarity NPD6101 Approved
0.7103 Intermediate Similarity NPD5328 Approved
0.7103 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7087 Intermediate Similarity NPD3667 Approved
0.7069 Intermediate Similarity NPD7899 Clinical (unspecified phase)
0.7064 Intermediate Similarity NPD4202 Approved
0.7063 Intermediate Similarity NPD6336 Discontinued
0.7059 Intermediate Similarity NPD7525 Registered
0.7037 Intermediate Similarity NPD46 Approved
0.7037 Intermediate Similarity NPD6698 Approved
0.7034 Intermediate Similarity NPD6371 Approved
0.7016 Intermediate Similarity NPD6921 Approved
0.7 Intermediate Similarity NPD7901 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7900 Approved
0.6991 Remote Similarity NPD5286 Approved
0.6991 Remote Similarity NPD4700 Approved
0.6991 Remote Similarity NPD4696 Approved
0.6991 Remote Similarity NPD5285 Approved
0.6981 Remote Similarity NPD3618 Phase 1
0.6972 Remote Similarity NPD6079 Approved
0.6937 Remote Similarity NPD5695 Phase 3
0.6923 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6916 Remote Similarity NPD7524 Approved
0.6909 Remote Similarity NPD5779 Approved
0.6909 Remote Similarity NPD5778 Approved
0.6905 Remote Similarity NPD6067 Discontinued
0.6903 Remote Similarity NPD5696 Approved
0.6897 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6885 Remote Similarity NPD6274 Approved
0.687 Remote Similarity NPD5225 Approved
0.687 Remote Similarity NPD4633 Approved
0.687 Remote Similarity NPD7632 Discontinued
0.687 Remote Similarity NPD5226 Approved
0.687 Remote Similarity NPD5224 Approved
0.687 Remote Similarity NPD5211 Phase 2
0.6863 Remote Similarity NPD6115 Approved
0.6863 Remote Similarity NPD6697 Approved
0.6863 Remote Similarity NPD6118 Approved
0.6863 Remote Similarity NPD6114 Approved
0.6855 Remote Similarity NPD7101 Approved
0.6855 Remote Similarity NPD7100 Approved
0.6852 Remote Similarity NPD6672 Approved
0.6852 Remote Similarity NPD5737 Approved
0.6847 Remote Similarity NPD5282 Discontinued
0.6838 Remote Similarity NPD4768 Approved
0.6838 Remote Similarity NPD4767 Approved
0.6822 Remote Similarity NPD7334 Approved
0.6822 Remote Similarity NPD7146 Approved
0.6822 Remote Similarity NPD6409 Approved
0.6822 Remote Similarity NPD6684 Approved
0.6822 Remote Similarity NPD7521 Approved
0.6822 Remote Similarity NPD5330 Approved
0.681 Remote Similarity NPD5174 Approved
0.681 Remote Similarity NPD5175 Approved
0.6792 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6789 Remote Similarity NPD4753 Phase 2
0.6786 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6783 Remote Similarity NPD5223 Approved
0.6777 Remote Similarity NPD6053 Discontinued
0.6774 Remote Similarity NPD6335 Approved
0.6765 Remote Similarity NPD6116 Phase 1
0.6752 Remote Similarity NPD5141 Approved
0.6746 Remote Similarity NPD6908 Approved
0.6746 Remote Similarity NPD6909 Approved
0.6726 Remote Similarity NPD7839 Suspended
0.6726 Remote Similarity NPD5221 Approved
0.6726 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6726 Remote Similarity NPD5222 Approved
0.6726 Remote Similarity NPD4697 Phase 3
0.6723 Remote Similarity NPD4729 Approved
0.6723 Remote Similarity NPD4730 Approved
0.6718 Remote Similarity NPD5956 Approved
0.6698 Remote Similarity NPD6695 Phase 3
0.6697 Remote Similarity NPD6903 Approved
0.6697 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6694 Remote Similarity NPD6317 Approved
0.6667 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4754 Approved
0.6667 Remote Similarity NPD5173 Approved
0.6667 Remote Similarity NPD6117 Approved
0.6667 Remote Similarity NPD6098 Approved
0.664 Remote Similarity NPD6313 Approved
0.664 Remote Similarity NPD6314 Approved
0.6638 Remote Similarity NPD5344 Discontinued
0.6636 Remote Similarity NPD3665 Phase 1
0.6636 Remote Similarity NPD6080 Approved
0.6636 Remote Similarity NPD6904 Approved
0.6636 Remote Similarity NPD3666 Approved
0.6636 Remote Similarity NPD3668 Phase 3
0.6636 Remote Similarity NPD6673 Approved
0.6636 Remote Similarity NPD3133 Approved
0.6613 Remote Similarity NPD6868 Approved
0.6612 Remote Similarity NPD5249 Phase 3
0.6612 Remote Similarity NPD5247 Approved
0.6612 Remote Similarity NPD5251 Approved
0.6612 Remote Similarity NPD5250 Approved
0.6612 Remote Similarity NPD5248 Approved
0.6609 Remote Similarity NPD8029 Clinical (unspecified phase)
0.6606 Remote Similarity NPD7750 Discontinued
0.6606 Remote Similarity NPD3573 Approved
0.6583 Remote Similarity NPD5128 Approved
0.6569 Remote Similarity NPD7339 Approved
0.6569 Remote Similarity NPD6942 Approved
0.6565 Remote Similarity NPD8337 Approved
0.6565 Remote Similarity NPD8336 Approved
0.656 Remote Similarity NPD8137 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   71531902
ChEMBL   CHEMBL2392319
ZINC  

Physicochemical Properties

Molecular Weight:  592.36
ALogP:  0.9761
MLogP:  4.1
XLogP:  4.137
# Rotatable Bonds:  21
Polar Surface Area:  142.75
# H-Bond Aceptor:  9
# H-Bond Donor:  4
# Rings:  4
# Heavy Atoms:  42

Download Data

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General Info & Identifiers & Properties  
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Biological Activities  
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