Natural Product: NPC471118

Natural Product ID:  NPC471118
Common Name:   Fasciculol E
IUPAC Name:   [(2R,3R,5R,10S,12S,13R,14S,17R)-2,12-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-3-yl] 3-hydroxy-5-[(2-methoxy-2-oxoethyl)amino]-3-methyl-5-oxopentanoate
Synonyms:  
Molecular Formula:   C39H65NO11
Standard InCHIKey:  XCIUFBDNARZOSJ-QJMSLSFKSA-N
Standard InCHI:  InChI=1S/C39H65NO11/c1-34(2)27-12-11-24-25(16-29(44)39(8)23(14-15-38(24,39)7)22(21-41)10-13-28(43)35(3,4)48)37(27,6)17-26(42)33(34)51-31(46)19-36(5,49)18-30(45)40-20-32(47)50-9/h22-23,26-29,33,41-44,48-49H,10-21H2,1-9H3,(H,40,45)/t22-,23+,26+,27-,28+,29-,33-,36?,37+,38-,39-/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](O)[C@@H](C2(C)C)OC(=O)CC(CC(=NCC(=O)OC)O)(O)C)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
NPT147 Cell Line SK-MEL-2 Homo sapiens IC50 = 9060 nM 25863432
NPT148 Cell Line HCT-15 Homo sapiens IC50 > 30000 nM PubChem BioAssay data set
NPT81 Cell Line A549 Homo sapiens IC50 > 30000 nM 17845002
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 > 30000 nM DrugMatrix in vitro pharmacology data

  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 NPC471118 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 NPC471121
0.9907 High Similarity NPC471120
0.9907 High Similarity NPC471117
0.8624 High Similarity NPC55954
0.8624 High Similarity NPC218513
0.8532 High Similarity NPC471119
0.8532 High Similarity NPC296879
0.8174 Intermediate Similarity NPC90630
0.8174 Intermediate Similarity NPC475243
0.7969 Intermediate Similarity NPC477072
0.7931 Intermediate Similarity NPC475364
0.7876 Intermediate Similarity NPC473788
0.7876 Intermediate Similarity NPC475558
0.7778 Intermediate Similarity NPC204556
0.7627 Intermediate Similarity NPC477069
0.7627 Intermediate Similarity NPC477070
0.7537 Intermediate Similarity NPC265908
0.7521 Intermediate Similarity NPC475494
0.75 Intermediate Similarity NPC477073
0.7479 Intermediate Similarity NPC218853
0.7459 Intermediate Similarity NPC116024
0.7455 Intermediate Similarity NPC473269
0.7438 Intermediate Similarity NPC280782
0.7434 Intermediate Similarity NPC120708
0.7417 Intermediate Similarity NPC250956
0.7377 Intermediate Similarity NPC477074
0.7373 Intermediate Similarity NPC472655
0.7355 Intermediate Similarity NPC472003
0.735 Intermediate Similarity NPC474124
0.7328 Intermediate Similarity NPC289670
0.7297 Intermediate Similarity NPC136801
0.7295 Intermediate Similarity NPC233003
0.7293 Intermediate Similarity NPC76999
0.7288 Intermediate Similarity NPC473543
0.7288 Intermediate Similarity NPC475036
0.7288 Intermediate Similarity NPC471293
0.7273 Intermediate Similarity NPC129340
0.7265 Intermediate Similarity NPC476471
0.7265 Intermediate Similarity NPC475344
0.725 Intermediate Similarity NPC472218
0.725 Intermediate Similarity NPC472219
0.725 Intermediate Similarity NPC472217
0.725 Intermediate Similarity NPC258323
0.725 Intermediate Similarity NPC195708
0.7241 Intermediate Similarity NPC167974
0.7239 Intermediate Similarity NPC75318
0.7236 Intermediate Similarity NPC251309
0.7227 Intermediate Similarity NPC258130
0.7227 Intermediate Similarity NPC470587
0.7217 Intermediate Similarity NPC475032
0.7217 Intermediate Similarity NPC475033
0.7213 Intermediate Similarity NPC250481
0.7213 Intermediate Similarity NPC285410
0.7213 Intermediate Similarity NPC263827
0.7203 Intermediate Similarity NPC473523
0.7193 Intermediate Similarity NPC473648
0.7193 Intermediate Similarity NPC180557
0.7193 Intermediate Similarity NPC37787
0.7193 Intermediate Similarity NPC473415
0.7193 Intermediate Similarity NPC30677
0.7193 Intermediate Similarity NPC200702
0.7193 Intermediate Similarity NPC469329
0.719 Intermediate Similarity NPC173905
0.719 Intermediate Similarity NPC265655
0.719 Intermediate Similarity NPC284828
0.719 Intermediate Similarity NPC472216
0.719 Intermediate Similarity NPC5475
0.7185 Intermediate Similarity NPC145899
0.7179 Intermediate Similarity NPC475617
0.7179 Intermediate Similarity NPC476132
0.7179 Intermediate Similarity NPC155974
0.7168 Intermediate Similarity NPC27918
0.7167 Intermediate Similarity NPC59530
0.7165 Intermediate Similarity NPC251226
0.7155 Intermediate Similarity NPC470066
0.7155 Intermediate Similarity NPC300179
0.7155 Intermediate Similarity NPC119036
0.7155 Intermediate Similarity NPC470068
0.7155 Intermediate Similarity NPC102426
0.7155 Intermediate Similarity NPC470067
0.7154 Intermediate Similarity NPC234042
0.7154 Intermediate Similarity NPC152117
0.7153 Intermediate Similarity NPC180770
0.7153 Intermediate Similarity NPC302276
0.7143 Intermediate Similarity NPC139585
0.7143 Intermediate Similarity NPC9714
0.7143 Intermediate Similarity NPC475472
0.7143 Intermediate Similarity NPC289213
0.7143 Intermediate Similarity NPC65523
0.7143 Intermediate Similarity NPC96268
0.7131 Intermediate Similarity NPC5284
0.7131 Intermediate Similarity NPC101450
0.7122 Intermediate Similarity NPC475584
0.7122 Intermediate Similarity NPC475152
0.7122 Intermediate Similarity NPC475394
0.7119 Intermediate Similarity NPC470053
0.7109 Intermediate Similarity NPC4021
0.7109 Intermediate Similarity NPC129434
0.7109 Intermediate Similarity NPC159456
0.7107 Intermediate Similarity NPC273155
0.7105 Intermediate Similarity NPC474922
0.7105 Intermediate Similarity NPC240617
0.7101 Intermediate Similarity NPC82931
0.7101 Intermediate Similarity NPC172365
0.7101 Intermediate Similarity NPC210729
0.7097 Intermediate Similarity NPC194273
0.7097 Intermediate Similarity NPC472926
0.7097 Intermediate Similarity NPC320118
0.7094 Intermediate Similarity NPC476195
0.7094 Intermediate Similarity NPC208358
0.7094 Intermediate Similarity NPC230546
0.7094 Intermediate Similarity NPC473510
0.7094 Intermediate Similarity NPC316964
0.7091 Intermediate Similarity NPC270957
0.7091 Intermediate Similarity NPC119633
0.7091 Intermediate Similarity NPC321340
0.7091 Intermediate Similarity NPC171698
0.709 Intermediate Similarity NPC73829
0.709 Intermediate Similarity NPC119794
0.7087 Intermediate Similarity NPC230513
0.7087 Intermediate Similarity NPC472933
0.7087 Intermediate Similarity NPC232258
0.7087 Intermediate Similarity NPC42673
0.7083 Intermediate Similarity NPC323834
0.7083 Intermediate Similarity NPC60315
0.7083 Intermediate Similarity NPC477877
0.708 Intermediate Similarity NPC243680
0.708 Intermediate Similarity NPC200788
0.708 Intermediate Similarity NPC26888
0.7077 Intermediate Similarity NPC130229
0.7073 Intermediate Similarity NPC292196
0.7071 Intermediate Similarity NPC475892
0.7071 Intermediate Similarity NPC141669
0.7063 Intermediate Similarity NPC470171
0.7063 Intermediate Similarity NPC55296
0.7063 Intermediate Similarity NPC477252
0.7059 Intermediate Similarity NPC475623
0.7059 Intermediate Similarity NPC473694
0.7059 Intermediate Similarity NPC159442
0.7059 Intermediate Similarity NPC475334
0.7054 Intermediate Similarity NPC269642
0.7054 Intermediate Similarity NPC474889
0.705 Intermediate Similarity NPC162910
0.7049 Intermediate Similarity NPC118225
0.7043 Intermediate Similarity NPC279974
0.7043 Intermediate Similarity NPC48330
0.704 Intermediate Similarity NPC220293
0.704 Intermediate Similarity NPC243354
0.704 Intermediate Similarity NPC473882
0.7037 Intermediate Similarity NPC7988
0.7034 Intermediate Similarity NPC473514
0.7034 Intermediate Similarity NPC470054
0.7031 Intermediate Similarity NPC476849
0.7031 Intermediate Similarity NPC476961
0.7031 Intermediate Similarity NPC154491
0.7031 Intermediate Similarity NPC268530
0.7031 Intermediate Similarity NPC471406
0.7027 Intermediate Similarity NPC138756
0.7025 Intermediate Similarity NPC112780
0.7025 Intermediate Similarity NPC469318
0.7025 Intermediate Similarity NPC473173
0.7025 Intermediate Similarity NPC166993
0.7023 Intermediate Similarity NPC473635
0.7016 Intermediate Similarity NPC477253
0.7008 Intermediate Similarity NPC297179
0.7 Intermediate Similarity NPC474550
0.7 Intermediate Similarity NPC11895
0.7 Intermediate Similarity NPC31430
0.7 Intermediate Similarity NPC475585
0.7 Intermediate Similarity NPC103298
0.7 Intermediate Similarity NPC80809
0.7 Intermediate Similarity NPC473577
0.7 Intermediate Similarity NPC475331
0.7 Intermediate Similarity NPC181104
0.7 Intermediate Similarity NPC201144
0.7 Intermediate Similarity NPC288502
0.7 Intermediate Similarity NPC475335
0.7 Intermediate Similarity NPC121518
0.7 Intermediate Similarity NPC85593
0.6992 Remote Similarity NPC52241
0.6992 Remote Similarity NPC475317
0.6992 Remote Similarity NPC129689
0.6992 Remote Similarity NPC472214
0.6992 Remote Similarity NPC472215
0.6992 Remote Similarity NPC154856
0.6991 Remote Similarity NPC175628
0.6991 Remote Similarity NPC111585
0.6991 Remote Similarity NPC20388
0.6991 Remote Similarity NPC148414
0.6985 Remote Similarity NPC235772
0.6985 Remote Similarity NPC280941
0.6984 Remote Similarity NPC16081
0.6984 Remote Similarity NPC244127
0.6984 Remote Similarity NPC173686
0.6983 Remote Similarity NPC173272
0.6983 Remote Similarity NPC471822
0.6983 Remote Similarity NPC471777
0.6983 Remote Similarity NPC129569
0.6983 Remote Similarity NPC42042
0.6983 Remote Similarity NPC471903

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471118 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
0.6977 Remote Similarity NPD6909 Approved
0.6977 Remote Similarity NPD6908 Approved
0.6911 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6899 Remote Similarity NPD6319 Approved
0.6797 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6746 Remote Similarity NPD8297 Approved
0.6718 Remote Similarity NPD6921 Approved
0.6716 Remote Similarity NPD8074 Phase 3
0.6714 Remote Similarity NPD6333 Approved
0.6714 Remote Similarity NPD6334 Approved
0.6667 Remote Similarity NPD7115 Discovery
0.6667 Remote Similarity NPD8418 Phase 2
0.664 Remote Similarity NPD4061 Clinical (unspecified phase)
0.6617 Remote Similarity NPD7604 Phase 2
0.6593 Remote Similarity NPD8293 Discontinued
0.6583 Remote Similarity NPD7638 Approved
0.6567 Remote Similarity NPD7492 Approved
0.6562 Remote Similarity NPD4632 Approved
0.6544 Remote Similarity NPD7736 Approved
0.6532 Remote Similarity NPD5739 Approved
0.6532 Remote Similarity NPD7128 Approved
0.6532 Remote Similarity NPD6675 Approved
0.6532 Remote Similarity NPD6402 Approved
0.6529 Remote Similarity NPD7640 Approved
0.6529 Remote Similarity NPD7639 Approved
0.6519 Remote Similarity NPD6616 Approved
0.6515 Remote Similarity NPD6059 Approved
0.6515 Remote Similarity NPD6054 Approved
0.6508 Remote Similarity NPD6372 Approved
0.6508 Remote Similarity NPD6373 Approved
0.6496 Remote Similarity NPD7319 Approved
0.6471 Remote Similarity NPD7078 Approved
0.6457 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6441 Remote Similarity NPD6399 Phase 3
0.6434 Remote Similarity NPD8298 Phase 2
0.6429 Remote Similarity NPD6899 Approved
0.6429 Remote Similarity NPD7320 Approved
0.6429 Remote Similarity NPD6881 Approved
0.6429 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6423 Remote Similarity NPD7632 Discontinued
0.6418 Remote Similarity NPD6370 Approved
0.6412 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6406 Remote Similarity NPD6649 Approved
0.6406 Remote Similarity NPD8130 Phase 1
0.6406 Remote Similarity NPD6650 Approved
0.64 Remote Similarity NPD5357 Phase 1
0.6397 Remote Similarity NPD7507 Approved
0.637 Remote Similarity NPD8328 Phase 3
0.6357 Remote Similarity NPD8338 Approved
0.6357 Remote Similarity NPD6882 Approved
0.6356 Remote Similarity NPD6411 Approved
0.6349 Remote Similarity NPD5701 Approved
0.6349 Remote Similarity NPD5697 Approved
0.6343 Remote Similarity NPD8033 Approved
0.6343 Remote Similarity NPD6015 Approved
0.6343 Remote Similarity NPD6016 Approved
0.6328 Remote Similarity NPD6883 Approved
0.6328 Remote Similarity NPD7290 Approved
0.6328 Remote Similarity NPD7102 Approved
0.6328 Remote Similarity NPD6421 Discontinued
0.6328 Remote Similarity NPD4634 Approved
0.6316 Remote Similarity NPD7516 Approved
0.6311 Remote Similarity NPD4225 Approved
0.6308 Remote Similarity NPD8133 Approved
0.6304 Remote Similarity NPD8337 Approved
0.6304 Remote Similarity NPD8336 Approved
0.6296 Remote Similarity NPD5988 Approved
0.6288 Remote Similarity NPD6009 Approved
0.6286 Remote Similarity NPD7260 Phase 2
0.6279 Remote Similarity NPD6869 Approved
0.6279 Remote Similarity NPD6847 Approved
0.6279 Remote Similarity NPD6617 Approved
0.627 Remote Similarity NPD6008 Approved
0.6269 Remote Similarity NPD8377 Approved
0.6269 Remote Similarity NPD8294 Approved
0.626 Remote Similarity NPD6404 Discontinued
0.625 Remote Similarity NPD6012 Approved
0.625 Remote Similarity NPD6014 Approved
0.625 Remote Similarity NPD6013 Approved
0.6242 Remote Similarity NPD7625 Phase 1
0.6241 Remote Similarity NPD6845 Suspended
0.6241 Remote Similarity NPD7327 Approved
0.6241 Remote Similarity NPD7328 Approved
0.623 Remote Similarity NPD6084 Phase 2
0.623 Remote Similarity NPD6083 Phase 2
0.6222 Remote Similarity NPD5983 Phase 2
0.6222 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6222 Remote Similarity NPD8378 Approved
0.6222 Remote Similarity NPD8296 Approved
0.6222 Remote Similarity NPD8380 Approved
0.6222 Remote Similarity NPD8335 Approved
0.6222 Remote Similarity NPD8379 Approved
0.622 Remote Similarity NPD6412 Phase 2
0.622 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6218 Remote Similarity NPD8035 Phase 2
0.6218 Remote Similarity NPD8034 Phase 2
0.6218 Remote Similarity NPD7637 Suspended
0.6214 Remote Similarity NPD6914 Discontinued
0.621 Remote Similarity NPD4159 Approved
0.6198 Remote Similarity NPD5695 Phase 3
0.6186 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6186 Remote Similarity NPD5328 Approved
0.6186 Remote Similarity NPD6101 Approved
0.6176 Remote Similarity NPD8080 Discontinued
0.6174 Remote Similarity NPD4786 Approved
0.6172 Remote Similarity NPD8174 Phase 2
0.6172 Remote Similarity NPD6011 Approved
0.6167 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6167 Remote Similarity NPD5779 Approved
0.6167 Remote Similarity NPD5778 Approved
0.6159 Remote Similarity NPD6336 Discontinued
0.6154 Remote Similarity NPD1719 Phase 1
0.6154 Remote Similarity NPD7524 Approved
0.6154 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6142 Remote Similarity NPD6640 Phase 3
0.6121 Remote Similarity NPD7520 Clinical (unspecified phase)
0.6116 Remote Similarity NPD7748 Approved
0.6111 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6103 Remote Similarity NPD8513 Phase 3
0.6103 Remote Similarity NPD8515 Approved
0.6103 Remote Similarity NPD8516 Approved
0.6103 Remote Similarity NPD7503 Approved
0.6103 Remote Similarity NPD8517 Approved
0.6098 Remote Similarity NPD4755 Approved
0.6083 Remote Similarity NPD6079 Approved
0.6071 Remote Similarity NPD6118 Approved
0.6071 Remote Similarity NPD6697 Approved
0.6071 Remote Similarity NPD6033 Approved
0.6071 Remote Similarity NPD6114 Approved
0.6071 Remote Similarity NPD6115 Approved
0.6053 Remote Similarity NPD1448 Clinical (unspecified phase)
0.6047 Remote Similarity NPD6686 Approved
0.6042 Remote Similarity NPD8415 Approved
0.6032 Remote Similarity NPD3653 Clinical (unspecified phase)
0.6 Remote Similarity NPD5285 Approved
0.6 Remote Similarity NPD3168 Discontinued
0.6 Remote Similarity NPD4696 Approved
0.6 Remote Similarity NPD3667 Approved
0.6 Remote Similarity NPD5286 Approved
0.6 Remote Similarity NPD4700 Approved
0.5985 Remote Similarity NPD6053 Discontinued
0.5971 Remote Similarity NPD8299 Approved
0.5971 Remote Similarity NPD8340 Approved
0.5971 Remote Similarity NPD8342 Approved
0.5971 Remote Similarity NPD8341 Approved
0.597 Remote Similarity NPD6274 Approved
0.5968 Remote Similarity NPD7902 Approved
0.5966 Remote Similarity NPD4264 Clinical (unspecified phase)
0.5965 Remote Similarity NPD7525 Registered
0.5965 Remote Similarity NPD4748 Discontinued
0.5956 Remote Similarity NPD7101 Approved
0.5956 Remote Similarity NPD7100 Approved
0.595 Remote Similarity NPD7983 Approved
0.595 Remote Similarity NPD7515 Phase 2
0.5932 Remote Similarity NPD3618 Phase 1
0.5929 Remote Similarity NPD8451 Approved
0.592 Remote Similarity NPD5696 Approved
0.5906 Remote Similarity NPD5226 Approved
0.5906 Remote Similarity NPD5211 Phase 2
0.5906 Remote Similarity NPD4633 Approved
0.5906 Remote Similarity NPD5225 Approved
0.5906 Remote Similarity NPD5224 Approved
0.5903 Remote Similarity NPD8449 Approved
0.5902 Remote Similarity NPD4202 Approved
0.5899 Remote Similarity NPD7122 Discontinued
0.5893 Remote Similarity NPD6117 Approved
0.5891 Remote Similarity NPD4768 Approved
0.5891 Remote Similarity NPD4767 Approved
0.5887 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5887 Remote Similarity NPD8448 Approved
0.5887 Remote Similarity NPD5221 Approved
0.5887 Remote Similarity NPD4697 Phase 3
0.5887 Remote Similarity NPD5222 Approved
0.5882 Remote Similarity NPD6335 Approved
0.5878 Remote Similarity NPD8305 Approved
0.5878 Remote Similarity NPD8306 Approved
0.5874 Remote Similarity NPD8391 Approved
0.5874 Remote Similarity NPD8392 Approved
0.5874 Remote Similarity NPD8390 Approved
0.5868 Remote Similarity NPD6700 Approved
0.5868 Remote Similarity NPD6701 Clinical (unspecified phase)
0.5862 Remote Similarity NPD8450 Suspended
0.5859 Remote Similarity NPD5174 Approved
0.5859 Remote Similarity NPD5175 Approved
0.5854 Remote Similarity NPD5707 Approved
0.5852 Remote Similarity NPD6868 Approved
0.5841 Remote Similarity NPD6116 Phase 1
0.584 Remote Similarity NPD5173 Approved
0.5833 Remote Similarity NPD6420 Discontinued
0.5833 Remote Similarity NPD5737 Approved
0.5833 Remote Similarity NPD6672 Approved
0.5827 Remote Similarity NPD1700 Approved
0.5827 Remote Similarity NPD5344 Discontinued
0.5827 Remote Similarity NPD5223 Approved
0.5814 Remote Similarity NPD5141 Approved
0.5814 Remote Similarity NPD8170 Clinical (unspecified phase)
0.5812 Remote Similarity NPD6695 Phase 3
0.5809 Remote Similarity NPD6317 Approved
0.5806 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5804 Remote Similarity NPD6942 Approved

Structure

External Identifiers

PubChem CID   72715745
ChEMBL   CHEMBL2375635
ZINC  

Physicochemical Properties

Molecular Weight:  723.46
ALogP:  -0.4323
MLogP:  4.43
XLogP:  1.979
# Rotatable Bonds:  31
Polar Surface Area:  206.57
# H-Bond Aceptor:  12
# H-Bond Donor:  7
# Rings:  4
# Heavy Atoms:  51

Download Data

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