Natural Product: NPC55954

Natural Product ID:  NPC55954
Common Name:   Fasciculic Acid F
IUPAC Name:   (3S)-5-[[(2R,3R,5R,10S,12S,13R,14S,17R)-3,12-dihydroxy-4,4,10,13,14-pentamethyl-17-[(2R,5R)-1,5,6-trihydroxy-6-methylheptan-2-yl]-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl]oxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
Synonyms:  
Molecular Formula:   C36H60O10
Standard InCHIKey:  FLXWNHMMKNTKDN-KKGPIOPUSA-N
Standard InCHI:  InChI=1S/C36H60O10/c1-31(2)25-11-10-22-23(34(25,6)16-24(30(31)43)46-29(42)18-33(5,45)17-28(40)41)15-27(39)36(8)21(13-14-35(22,36)7)20(19-37)9-12-26(38)32(3,4)44/h20-21,24-27,30,37-39,43-45H,9-19H2,1-8H3,(H,40,41)/t20-,21+,24+,25-,26+,27-,30-,33-,34+,35-,36-/m0/s1
Canonical SMILES:  OC[C@@H]([C@H]1CC[C@@]2([C@]1(C)[C@@H](O)CC1=C2CC[C@@H]2[C@]1(C)C[C@@H](OC(=O)C[C@](CC(=O)O)(O)C)[C@@H](C2(C)C)O)C)CC[C@H](C(O)(C)C)O
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
NPO33351 naematoloma fasciculare Species Strophariaceae Eukaryota PMID[23634786]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT148 Cell Line HCT-15 Homo sapiens IC50 = 27960 nM 26465675
NPT81 Cell Line A549 Homo sapiens IC50 = 25520 nM 26465675
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 = 25230 nM 26465675
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 = 16170 nM 9748370

  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 NPC55954 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 NPC218513
0.9895 High Similarity NPC296879
0.9895 High Similarity NPC471119
0.9406 High Similarity NPC90630
0.9406 High Similarity NPC475243
0.9118 High Similarity NPC475364
0.9091 High Similarity NPC475558
0.9091 High Similarity NPC473788
0.8624 High Similarity NPC471118
0.8624 High Similarity NPC471121
0.8571 High Similarity NPC477070
0.8571 High Similarity NPC477069
0.8532 High Similarity NPC471117
0.8532 High Similarity NPC471120
0.8519 High Similarity NPC116024
0.8462 Intermediate Similarity NPC475494
0.8454 Intermediate Similarity NPC473269
0.8411 Intermediate Similarity NPC477073
0.84 Intermediate Similarity NPC120708
0.8396 Intermediate Similarity NPC218853
0.8333 Intermediate Similarity NPC280782
0.8318 Intermediate Similarity NPC250956
0.8286 Intermediate Similarity NPC472655
0.8269 Intermediate Similarity NPC474124
0.8265 Intermediate Similarity NPC136801
0.8257 Intermediate Similarity NPC477074
0.8252 Intermediate Similarity NPC289670
0.8241 Intermediate Similarity NPC472003
0.819 Intermediate Similarity NPC475036
0.819 Intermediate Similarity NPC473543
0.819 Intermediate Similarity NPC471293
0.8173 Intermediate Similarity NPC475344
0.8173 Intermediate Similarity NPC476471
0.8165 Intermediate Similarity NPC233003
0.8155 Intermediate Similarity NPC167974
0.8148 Intermediate Similarity NPC129340
0.8137 Intermediate Similarity NPC475032
0.8137 Intermediate Similarity NPC475033
0.8131 Intermediate Similarity NPC472219
0.8131 Intermediate Similarity NPC472217
0.8131 Intermediate Similarity NPC258323
0.8131 Intermediate Similarity NPC472218
0.8131 Intermediate Similarity NPC195708
0.8119 Intermediate Similarity NPC37787
0.8119 Intermediate Similarity NPC473415
0.8119 Intermediate Similarity NPC180557
0.8119 Intermediate Similarity NPC469329
0.8119 Intermediate Similarity NPC473648
0.8119 Intermediate Similarity NPC30677
0.8119 Intermediate Similarity NPC200702
0.8113 Intermediate Similarity NPC470587
0.81 Intermediate Similarity NPC27918
0.8095 Intermediate Similarity NPC473523
0.8091 Intermediate Similarity NPC251309
0.8081 Intermediate Similarity NPC289213
0.8077 Intermediate Similarity NPC155974
0.8077 Intermediate Similarity NPC475617
0.8077 Intermediate Similarity NPC476132
0.8073 Intermediate Similarity NPC250481
0.8073 Intermediate Similarity NPC285410
0.8073 Intermediate Similarity NPC263827
0.8058 Intermediate Similarity NPC470068
0.8058 Intermediate Similarity NPC470066
0.8058 Intermediate Similarity NPC300179
0.8058 Intermediate Similarity NPC102426
0.8058 Intermediate Similarity NPC119036
0.8058 Intermediate Similarity NPC470067
0.8056 Intermediate Similarity NPC472216
0.8056 Intermediate Similarity NPC284828
0.8056 Intermediate Similarity NPC173905
0.8056 Intermediate Similarity NPC5475
0.8056 Intermediate Similarity NPC265655
0.8053 Intermediate Similarity NPC472933
0.8037 Intermediate Similarity NPC59530
0.802 Intermediate Similarity NPC240617
0.802 Intermediate Similarity NPC474922
0.8019 Intermediate Similarity NPC65523
0.8019 Intermediate Similarity NPC96268
0.8 Intermediate Similarity NPC26888
0.8 Intermediate Similarity NPC470053
0.8 Intermediate Similarity NPC234042
0.8 Intermediate Similarity NPC152117
0.8 Intermediate Similarity NPC7988
0.7982 Intermediate Similarity NPC251226
0.7982 Intermediate Similarity NPC5284
0.7982 Intermediate Similarity NPC101450
0.7982 Intermediate Similarity NPC129689
0.7981 Intermediate Similarity NPC230546
0.7981 Intermediate Similarity NPC473510
0.7981 Intermediate Similarity NPC476195
0.7981 Intermediate Similarity NPC208358
0.7981 Intermediate Similarity NPC316964
0.798 Intermediate Similarity NPC474889
0.7963 Intermediate Similarity NPC273155
0.7959 Intermediate Similarity NPC138756
0.7946 Intermediate Similarity NPC173686
0.7946 Intermediate Similarity NPC16081
0.7944 Intermediate Similarity NPC323834
0.7944 Intermediate Similarity NPC60315
0.7944 Intermediate Similarity NPC477877
0.7941 Intermediate Similarity NPC48330
0.7941 Intermediate Similarity NPC279974
0.7928 Intermediate Similarity NPC194273
0.7928 Intermediate Similarity NPC472926
0.7928 Intermediate Similarity NPC320118
0.7925 Intermediate Similarity NPC475623
0.7925 Intermediate Similarity NPC159442
0.7925 Intermediate Similarity NPC475334
0.7925 Intermediate Similarity NPC473694
0.7913 Intermediate Similarity NPC129434
0.7913 Intermediate Similarity NPC4021
0.7913 Intermediate Similarity NPC159456
0.7909 Intermediate Similarity NPC292196
0.7909 Intermediate Similarity NPC115303
0.7905 Intermediate Similarity NPC470054
0.7905 Intermediate Similarity NPC473514
0.79 Intermediate Similarity NPC175628
0.79 Intermediate Similarity NPC111585
0.79 Intermediate Similarity NPC148414
0.79 Intermediate Similarity NPC20388
0.7895 Intermediate Similarity NPC232258
0.7895 Intermediate Similarity NPC42673
0.7895 Intermediate Similarity NPC230513
0.789 Intermediate Similarity NPC118225
0.789 Intermediate Similarity NPC77947
0.789 Intermediate Similarity NPC286174
0.7879 Intermediate Similarity NPC242864
0.7876 Intermediate Similarity NPC477252
0.7876 Intermediate Similarity NPC472934
0.7876 Intermediate Similarity NPC472927
0.7876 Intermediate Similarity NPC55296
0.7876 Intermediate Similarity NPC470171
0.787 Intermediate Similarity NPC473173
0.787 Intermediate Similarity NPC112780
0.787 Intermediate Similarity NPC166993
0.787 Intermediate Similarity NPC469318
0.7864 Intermediate Similarity NPC42042
0.7864 Intermediate Similarity NPC7124
0.7864 Intermediate Similarity NPC471777
0.7864 Intermediate Similarity NPC471903
0.7864 Intermediate Similarity NPC173272
0.7864 Intermediate Similarity NPC471822
0.7864 Intermediate Similarity NPC129569
0.7863 Intermediate Similarity NPC130229
0.7857 Intermediate Similarity NPC268238
0.7857 Intermediate Similarity NPC220293
0.7857 Intermediate Similarity NPC243354
0.7857 Intermediate Similarity NPC473882
0.7857 Intermediate Similarity NPC143268
0.7857 Intermediate Similarity NPC473898
0.7857 Intermediate Similarity NPC323821
0.7857 Intermediate Similarity NPC45218
0.785 Intermediate Similarity NPC2436
0.785 Intermediate Similarity NPC216245
0.785 Intermediate Similarity NPC121518
0.785 Intermediate Similarity NPC181104
0.785 Intermediate Similarity NPC475585
0.785 Intermediate Similarity NPC473577
0.785 Intermediate Similarity NPC103298
0.785 Intermediate Similarity NPC85593
0.785 Intermediate Similarity NPC201144
0.785 Intermediate Similarity NPC474550
0.785 Intermediate Similarity NPC31430
0.785 Intermediate Similarity NPC288502
0.785 Intermediate Similarity NPC475331
0.785 Intermediate Similarity NPC135854
0.785 Intermediate Similarity NPC80809
0.785 Intermediate Similarity NPC470251
0.785 Intermediate Similarity NPC475335
0.7845 Intermediate Similarity NPC269642
0.7838 Intermediate Similarity NPC477253
0.783 Intermediate Similarity NPC473928
0.783 Intermediate Similarity NPC281702
0.783 Intermediate Similarity NPC469316
0.7826 Intermediate Similarity NPC268530
0.7826 Intermediate Similarity NPC476849
0.7826 Intermediate Similarity NPC471406
0.7826 Intermediate Similarity NPC476961
0.7826 Intermediate Similarity NPC154491
0.7822 Intermediate Similarity NPC219516
0.7822 Intermediate Similarity NPC189520
0.7822 Intermediate Similarity NPC473166
0.7818 Intermediate Similarity NPC52241
0.7818 Intermediate Similarity NPC475317
0.7818 Intermediate Similarity NPC472215
0.7818 Intermediate Similarity NPC154856
0.7818 Intermediate Similarity NPC472214
0.781 Intermediate Similarity NPC94906
0.781 Intermediate Similarity NPC188968
0.781 Intermediate Similarity NPC307954
0.7807 Intermediate Similarity NPC470776
0.7807 Intermediate Similarity NPC297179
0.7807 Intermediate Similarity NPC17772
0.7798 Intermediate Similarity NPC295389
0.7798 Intermediate Similarity NPC88701
0.7798 Intermediate Similarity NPC285576
0.7798 Intermediate Similarity NPC94942
0.7797 Intermediate Similarity NPC473635
0.7789 Intermediate Similarity NPC22403
0.7788 Intermediate Similarity NPC210337

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC55954 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
0.7727 Intermediate Similarity NPD8132 Clinical (unspecified phase)
0.7672 Intermediate Similarity NPD6319 Approved
0.7565 Intermediate Similarity NPD8295 Clinical (unspecified phase)
0.7522 Intermediate Similarity NPD8297 Approved
0.7414 Intermediate Similarity NPD7115 Discovery
0.7411 Intermediate Similarity NPD4061 Clinical (unspecified phase)
0.7383 Intermediate Similarity NPD7638 Approved
0.7315 Intermediate Similarity NPD7640 Approved
0.7315 Intermediate Similarity NPD7639 Approved
0.7304 Intermediate Similarity NPD4632 Approved
0.7297 Intermediate Similarity NPD5739 Approved
0.7297 Intermediate Similarity NPD6675 Approved
0.7297 Intermediate Similarity NPD6402 Approved
0.7297 Intermediate Similarity NPD7128 Approved
0.7295 Intermediate Similarity NPD8293 Discontinued
0.7273 Intermediate Similarity NPD7492 Approved
0.7257 Intermediate Similarity NPD6372 Approved
0.7257 Intermediate Similarity NPD6373 Approved
0.7238 Intermediate Similarity NPD6399 Phase 3
0.7236 Intermediate Similarity NPD7736 Approved
0.7227 Intermediate Similarity NPD6054 Approved
0.7227 Intermediate Similarity NPD6059 Approved
0.7213 Intermediate Similarity NPD6616 Approved
0.7193 Intermediate Similarity NPD5955 Clinical (unspecified phase)
0.7182 Intermediate Similarity NPD7632 Discontinued
0.7177 Intermediate Similarity NPD7319 Approved
0.7168 Intermediate Similarity NPD6899 Approved
0.7168 Intermediate Similarity NPD6881 Approved
0.7168 Intermediate Similarity NPD7320 Approved
0.7168 Intermediate Similarity NPD5345 Clinical (unspecified phase)
0.7154 Intermediate Similarity NPD7078 Approved
0.7143 Intermediate Similarity NPD6411 Approved
0.713 Intermediate Similarity NPD6649 Approved
0.713 Intermediate Similarity NPD8130 Phase 1
0.713 Intermediate Similarity NPD6650 Approved
0.7107 Intermediate Similarity NPD6370 Approved
0.708 Intermediate Similarity NPD5697 Approved
0.708 Intermediate Similarity NPD5701 Approved
0.7073 Intermediate Similarity NPD7507 Approved
0.7069 Intermediate Similarity NPD6882 Approved
0.7064 Intermediate Similarity NPD4225 Approved
0.7049 Intermediate Similarity NPD8328 Phase 3
0.7043 Intermediate Similarity NPD6883 Approved
0.7043 Intermediate Similarity NPD7290 Approved
0.7043 Intermediate Similarity NPD7102 Approved
0.7043 Intermediate Similarity NPD4634 Approved
0.7025 Intermediate Similarity NPD6016 Approved
0.7025 Intermediate Similarity NPD6015 Approved
0.7025 Intermediate Similarity NPD8033 Approved
0.7009 Intermediate Similarity NPD8133 Approved
0.7 Intermediate Similarity NPD7516 Approved
0.6991 Remote Similarity NPD6008 Approved
0.6983 Remote Similarity NPD6617 Approved
0.6983 Remote Similarity NPD6847 Approved
0.6983 Remote Similarity NPD6869 Approved
0.6981 Remote Similarity NPD7637 Suspended
0.6981 Remote Similarity NPD8035 Phase 2
0.6981 Remote Similarity NPD8034 Phase 2
0.6975 Remote Similarity NPD6009 Approved
0.6972 Remote Similarity NPD6084 Phase 2
0.6972 Remote Similarity NPD6083 Phase 2
0.6967 Remote Similarity NPD5988 Approved
0.6961 Remote Similarity NPD4786 Approved
0.6957 Remote Similarity NPD6013 Approved
0.6957 Remote Similarity NPD6012 Approved
0.6957 Remote Similarity NPD6014 Approved
0.6952 Remote Similarity NPD6101 Approved
0.6952 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6952 Remote Similarity NPD5328 Approved
0.6944 Remote Similarity NPD5695 Phase 3
0.6942 Remote Similarity NPD8294 Approved
0.6942 Remote Similarity NPD8377 Approved
0.693 Remote Similarity NPD6412 Phase 2
0.693 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7524 Approved
0.6917 Remote Similarity NPD7328 Approved
0.6917 Remote Similarity NPD7327 Approved
0.6916 Remote Similarity NPD5778 Approved
0.6916 Remote Similarity NPD5779 Approved
0.6911 Remote Similarity NPD7604 Phase 2
0.6893 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6885 Remote Similarity NPD8378 Approved
0.6885 Remote Similarity NPD8296 Approved
0.6885 Remote Similarity NPD8380 Approved
0.6885 Remote Similarity NPD8379 Approved
0.6885 Remote Similarity NPD5983 Phase 2
0.6885 Remote Similarity NPD8335 Approved
0.687 Remote Similarity NPD6011 Approved
0.6869 Remote Similarity NPD6115 Approved
0.6869 Remote Similarity NPD6697 Approved
0.6869 Remote Similarity NPD6118 Approved
0.6869 Remote Similarity NPD6114 Approved
0.6852 Remote Similarity NPD7748 Approved
0.6838 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6822 Remote Similarity NPD6079 Approved
0.6818 Remote Similarity NPD4755 Approved
0.68 Remote Similarity NPD6336 Discontinued
0.6765 Remote Similarity NPD3667 Approved
0.6757 Remote Similarity NPD5696 Approved
0.6748 Remote Similarity NPD8513 Phase 3
0.6748 Remote Similarity NPD7503 Approved
0.6748 Remote Similarity NPD8517 Approved
0.6748 Remote Similarity NPD8516 Approved
0.6748 Remote Similarity NPD8515 Approved
0.6733 Remote Similarity NPD4748 Discontinued
0.6733 Remote Similarity NPD7525 Registered
0.6724 Remote Similarity NPD6686 Approved
0.6696 Remote Similarity NPD5286 Approved
0.6696 Remote Similarity NPD5285 Approved
0.6696 Remote Similarity NPD4700 Approved
0.6696 Remote Similarity NPD4696 Approved
0.6693 Remote Similarity NPD6033 Approved
0.6667 Remote Similarity NPD6117 Approved
0.6667 Remote Similarity NPD7515 Phase 2
0.6667 Remote Similarity NPD7983 Approved
0.6667 Remote Similarity NPD7902 Approved
0.6667 Remote Similarity NPD3618 Phase 1
0.6639 Remote Similarity NPD6053 Discontinued
0.6613 Remote Similarity NPD6921 Approved
0.6612 Remote Similarity NPD6274 Approved
0.6606 Remote Similarity NPD4202 Approved
0.66 Remote Similarity NPD6116 Phase 1
0.6585 Remote Similarity NPD7100 Approved
0.6585 Remote Similarity NPD7101 Approved
0.6579 Remote Similarity NPD5226 Approved
0.6579 Remote Similarity NPD5225 Approved
0.6579 Remote Similarity NPD4633 Approved
0.6579 Remote Similarity NPD5224 Approved
0.6579 Remote Similarity NPD5211 Phase 2
0.6577 Remote Similarity NPD5220 Clinical (unspecified phase)
0.6577 Remote Similarity NPD5222 Approved
0.6577 Remote Similarity NPD4697 Phase 3
0.6577 Remote Similarity NPD5221 Approved
0.6566 Remote Similarity NPD7339 Approved
0.6566 Remote Similarity NPD6942 Approved
0.6552 Remote Similarity NPD4767 Approved
0.6552 Remote Similarity NPD4768 Approved
0.6542 Remote Similarity NPD5737 Approved
0.6542 Remote Similarity NPD6672 Approved
0.6538 Remote Similarity NPD6695 Phase 3
0.6522 Remote Similarity NPD5174 Approved
0.6522 Remote Similarity NPD5175 Approved
0.6518 Remote Similarity NPD5173 Approved
0.6509 Remote Similarity NPD7334 Approved
0.6509 Remote Similarity NPD6409 Approved
0.6509 Remote Similarity NPD7521 Approved
0.6509 Remote Similarity NPD5330 Approved
0.6509 Remote Similarity NPD7146 Approved
0.6509 Remote Similarity NPD6684 Approved
0.6509 Remote Similarity NPD3574 Clinical (unspecified phase)
0.6504 Remote Similarity NPD6335 Approved
0.6491 Remote Similarity NPD1700 Approved
0.6491 Remote Similarity NPD5223 Approved
0.6491 Remote Similarity NPD4159 Approved
0.6491 Remote Similarity NPD5344 Discontinued
0.6486 Remote Similarity NPD6356 Clinical (unspecified phase)
0.6484 Remote Similarity NPD8074 Phase 3
0.6481 Remote Similarity NPD4753 Phase 2
0.648 Remote Similarity NPD6909 Approved
0.648 Remote Similarity NPD6908 Approved
0.6476 Remote Similarity NPD7338 Clinical (unspecified phase)
0.6475 Remote Similarity NPD6868 Approved
0.6466 Remote Similarity NPD5141 Approved
0.6466 Remote Similarity NPD8170 Clinical (unspecified phase)
0.6465 Remote Similarity NPD6113 Clinical (unspecified phase)
0.6449 Remote Similarity NPD7750 Discontinued
0.6441 Remote Similarity NPD4729 Approved
0.6441 Remote Similarity NPD4730 Approved
0.6423 Remote Similarity NPD6317 Approved
0.6396 Remote Similarity NPD7901 Clinical (unspecified phase)
0.6396 Remote Similarity NPD7900 Approved
0.6392 Remote Similarity NPD4267 Clinical (unspecified phase)
0.6389 Remote Similarity NPD6903 Approved
0.6389 Remote Similarity NPD7513 Clinical (unspecified phase)
0.6379 Remote Similarity NPD4754 Approved
0.6371 Remote Similarity NPD6313 Approved
0.6371 Remote Similarity NPD6314 Approved
0.6364 Remote Similarity NPD5284 Approved
0.6364 Remote Similarity NPD5281 Approved
0.6364 Remote Similarity NPD6050 Approved
0.6356 Remote Similarity NPD7899 Clinical (unspecified phase)
0.6355 Remote Similarity NPD6098 Approved
0.6355 Remote Similarity NPD5279 Phase 3
0.6346 Remote Similarity NPD4139 Approved
0.6346 Remote Similarity NPD4692 Approved
0.6339 Remote Similarity NPD4629 Approved
0.6339 Remote Similarity NPD5210 Approved
0.6337 Remote Similarity NPD3701 Clinical (unspecified phase)
0.6337 Remote Similarity NPD6933 Approved
0.6333 Remote Similarity NPD5249 Phase 3
0.6333 Remote Similarity NPD6371 Approved
0.6333 Remote Similarity NPD5247 Approved
0.6333 Remote Similarity NPD5251 Approved
0.6333 Remote Similarity NPD5250 Approved
0.6333 Remote Similarity NPD5248 Approved
0.633 Remote Similarity NPD6904 Approved
0.633 Remote Similarity NPD6080 Approved
0.633 Remote Similarity NPD6051 Approved
0.633 Remote Similarity NPD6673 Approved
0.6321 Remote Similarity NPD3668 Phase 3

Structure

External Identifiers

PubChem CID   73350375
ChEMBL   CHEMBL2375637
ZINC  

Physicochemical Properties

Molecular Weight:  652.42
ALogP:  -0.3999
MLogP:  4.32
XLogP:  2.414
# Rotatable Bonds:  27
Polar Surface Area:  184.98
# H-Bond Aceptor:  10
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  46

Download Data

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Biological Activities  
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