Natural Product: NPC471120

Natural Product ID:  NPC471120
Common Name:   Fasciculol D
IUPAC Name:   [(2R,3R,5R,10S,12S,13R,14S,17R)-17-[(2R,5R)-5,6-dihydroxy-6-methylheptan-2-yl]-3,12-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,7,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl] 3-hydroxy-5-[(2-methoxy-2-oxoethyl)amino]-3-methyl-5-oxopentanoate
Synonyms:  
Molecular Formula:   C39H65NO10
Standard InCHIKey:  UFHYUEPVXXEOIS-NPIAJXLBSA-N
Standard InCHI:  InChI=1S/C39H65NO10/c1-22(11-14-28(41)35(4,5)47)23-15-16-38(8)24-12-13-27-34(2,3)33(46)26(18-37(27,7)25(24)17-29(42)39(23,38)9)50-31(44)20-36(6,48)19-30(43)40-21-32(45)49-10/h22-23,26-29,33,41-42,46-48H,11-21H2,1-10H3,(H,40,43)/t22-,23-,26-,27+,28-,29+,33+,36?,37-,38+,39+/m1/s1
Canonical SMILES:  COC(=O)CN=C(CC(CC(=O)O[C@@H]1C[C@]2(C)C3=C(CC[C@H]2C([C@H]1O)(C)C)[C@]1([C@@]([C@H](C3)O)(C)[C@H](CC1)[C@@H](CC[C@H](C(O)(C)C)O)C)C)(O)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 = 9160 nM 9748370
NPT146 Cell Line SK-OV-3 Homo sapiens IC50 > 30000 nM 19273669
NPT148 Cell Line HCT-15 Homo sapiens IC50 > 30000 nM 24215398
NPT81 Cell Line A549 Homo sapiens IC50 > 30000 nM 15711537

  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 NPC471120 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 NPC471117
0.9907 High Similarity NPC471118
0.9907 High Similarity NPC471121
0.8611 High Similarity NPC471119
0.8611 High Similarity NPC296879
0.8532 High Similarity NPC218513
0.8532 High Similarity NPC55954
0.8087 Intermediate Similarity NPC90630
0.8087 Intermediate Similarity NPC475243
0.7946 Intermediate Similarity NPC475558
0.7946 Intermediate Similarity NPC473788
0.7891 Intermediate Similarity NPC477072
0.7845 Intermediate Similarity NPC475364
0.7698 Intermediate Similarity NPC204556
0.7586 Intermediate Similarity NPC475494
0.7542 Intermediate Similarity NPC477070
0.7542 Intermediate Similarity NPC477069
0.7523 Intermediate Similarity NPC473269
0.7521 Intermediate Similarity NPC116024
0.75 Intermediate Similarity NPC120708
0.7463 Intermediate Similarity NPC265908
0.7417 Intermediate Similarity NPC477073
0.7395 Intermediate Similarity NPC218853
0.7355 Intermediate Similarity NPC280782
0.7333 Intermediate Similarity NPC250956
0.7311 Intermediate Similarity NPC195708
0.7295 Intermediate Similarity NPC477074
0.7288 Intermediate Similarity NPC258130
0.7288 Intermediate Similarity NPC472655
0.7273 Intermediate Similarity NPC472003
0.7265 Intermediate Similarity NPC474124
0.7257 Intermediate Similarity NPC37787
0.7257 Intermediate Similarity NPC30677
0.7257 Intermediate Similarity NPC469329
0.7257 Intermediate Similarity NPC473415
0.7257 Intermediate Similarity NPC473648
0.7257 Intermediate Similarity NPC180557
0.725 Intermediate Similarity NPC265655
0.7241 Intermediate Similarity NPC289670
0.7232 Intermediate Similarity NPC27918
0.7218 Intermediate Similarity NPC76999
0.7213 Intermediate Similarity NPC233003
0.7207 Intermediate Similarity NPC136801
0.7203 Intermediate Similarity NPC473543
0.7203 Intermediate Similarity NPC471293
0.7203 Intermediate Similarity NPC475036
0.719 Intermediate Similarity NPC129340
0.7179 Intermediate Similarity NPC475344
0.7179 Intermediate Similarity NPC476471
0.7168 Intermediate Similarity NPC240617
0.7167 Intermediate Similarity NPC258323
0.7167 Intermediate Similarity NPC472217
0.7167 Intermediate Similarity NPC472219
0.7167 Intermediate Similarity NPC472218
0.7164 Intermediate Similarity NPC75318
0.7155 Intermediate Similarity NPC473510
0.7155 Intermediate Similarity NPC316964
0.7155 Intermediate Similarity NPC230546
0.7155 Intermediate Similarity NPC167974
0.7154 Intermediate Similarity NPC251309
0.7143 Intermediate Similarity NPC470587
0.7143 Intermediate Similarity NPC26888
0.7131 Intermediate Similarity NPC263827
0.7131 Intermediate Similarity NPC250481
0.7131 Intermediate Similarity NPC285410
0.7131 Intermediate Similarity NPC292196
0.713 Intermediate Similarity NPC475032
0.713 Intermediate Similarity NPC475033
0.7119 Intermediate Similarity NPC473523
0.7117 Intermediate Similarity NPC474889
0.7111 Intermediate Similarity NPC145899
0.7107 Intermediate Similarity NPC173905
0.7107 Intermediate Similarity NPC472216
0.7107 Intermediate Similarity NPC284828
0.7107 Intermediate Similarity NPC5475
0.7105 Intermediate Similarity NPC200702
0.7097 Intermediate Similarity NPC220293
0.7094 Intermediate Similarity NPC475617
0.7094 Intermediate Similarity NPC476132
0.7094 Intermediate Similarity NPC155974
0.7094 Intermediate Similarity NPC473514
0.7091 Intermediate Similarity NPC138756
0.7087 Intermediate Similarity NPC251226
0.7083 Intermediate Similarity NPC59530
0.708 Intermediate Similarity NPC302276
0.708 Intermediate Similarity NPC180770
0.7073 Intermediate Similarity NPC152117
0.7073 Intermediate Similarity NPC234042
0.7069 Intermediate Similarity NPC470068
0.7069 Intermediate Similarity NPC470067
0.7069 Intermediate Similarity NPC300179
0.7069 Intermediate Similarity NPC102426
0.7069 Intermediate Similarity NPC119036
0.7069 Intermediate Similarity NPC470066
0.7068 Intermediate Similarity NPC139585
0.7068 Intermediate Similarity NPC475472
0.7063 Intermediate Similarity NPC9714
0.7059 Intermediate Similarity NPC96268
0.7059 Intermediate Similarity NPC65523
0.7054 Intermediate Similarity NPC289213
0.7054 Intermediate Similarity NPC148414
0.7054 Intermediate Similarity NPC20388
0.7054 Intermediate Similarity NPC111585
0.7054 Intermediate Similarity NPC175628
0.705 Intermediate Similarity NPC475394
0.705 Intermediate Similarity NPC475152
0.705 Intermediate Similarity NPC475584
0.7049 Intermediate Similarity NPC101450
0.7049 Intermediate Similarity NPC5284
0.7043 Intermediate Similarity NPC471822
0.7043 Intermediate Similarity NPC471777
0.7034 Intermediate Similarity NPC473928
0.7034 Intermediate Similarity NPC469316
0.7034 Intermediate Similarity NPC470053
0.7031 Intermediate Similarity NPC129434
0.7031 Intermediate Similarity NPC159456
0.7031 Intermediate Similarity NPC4021
0.7029 Intermediate Similarity NPC210729
0.7029 Intermediate Similarity NPC82931
0.7029 Intermediate Similarity NPC172365
0.7027 Intermediate Similarity NPC242864
0.7025 Intermediate Similarity NPC273155
0.7018 Intermediate Similarity NPC474922
0.7016 Intermediate Similarity NPC320118
0.7016 Intermediate Similarity NPC194273
0.7016 Intermediate Similarity NPC472926
0.7015 Intermediate Similarity NPC119794
0.7015 Intermediate Similarity NPC73829
0.7009 Intermediate Similarity NPC476195
0.7009 Intermediate Similarity NPC208358
0.7008 Intermediate Similarity NPC472933
0.7008 Intermediate Similarity NPC232258
0.7008 Intermediate Similarity NPC42673
0.7008 Intermediate Similarity NPC230513
0.7007 Intermediate Similarity NPC200788
0.7007 Intermediate Similarity NPC243680
0.7 Intermediate Similarity NPC475892
0.7 Intermediate Similarity NPC119633
0.7 Intermediate Similarity NPC60315
0.7 Intermediate Similarity NPC130229
0.7 Intermediate Similarity NPC171698
0.7 Intermediate Similarity NPC323834
0.7 Intermediate Similarity NPC141669
0.7 Intermediate Similarity NPC270957
0.7 Intermediate Similarity NPC321340
0.7 Intermediate Similarity NPC477877
0.6991 Remote Similarity NPC189520
0.6991 Remote Similarity NPC473166
0.6984 Remote Similarity NPC477252
0.6984 Remote Similarity NPC472934
0.6984 Remote Similarity NPC470171
0.6984 Remote Similarity NPC55296
0.6983 Remote Similarity NPC210337
0.6978 Remote Similarity NPC162910
0.6977 Remote Similarity NPC269642
0.6975 Remote Similarity NPC473694
0.6975 Remote Similarity NPC159442
0.6975 Remote Similarity NPC475334
0.6975 Remote Similarity NPC475623
0.6972 Remote Similarity NPC175419
0.6967 Remote Similarity NPC118225
0.6967 Remote Similarity NPC41405
0.696 Remote Similarity NPC473882
0.696 Remote Similarity NPC470540
0.696 Remote Similarity NPC243354
0.696 Remote Similarity NPC284915
0.6957 Remote Similarity NPC69548
0.6957 Remote Similarity NPC48330
0.6957 Remote Similarity NPC184848
0.6957 Remote Similarity NPC279974
0.6957 Remote Similarity NPC470016
0.6957 Remote Similarity NPC317586
0.6953 Remote Similarity NPC476961
0.6953 Remote Similarity NPC154491
0.6953 Remote Similarity NPC471406
0.6953 Remote Similarity NPC476849
0.6953 Remote Similarity NPC268530
0.6949 Remote Similarity NPC470054
0.6949 Remote Similarity NPC469327
0.6947 Remote Similarity NPC473635
0.6944 Remote Similarity NPC7988
0.6942 Remote Similarity NPC9457
0.6942 Remote Similarity NPC166993
0.6942 Remote Similarity NPC112780
0.6942 Remote Similarity NPC471783
0.6942 Remote Similarity NPC469318
0.6942 Remote Similarity NPC473173
0.6935 Remote Similarity NPC477253
0.6929 Remote Similarity NPC297179
0.6929 Remote Similarity NPC470276
0.6923 Remote Similarity NPC11895
0.6917 Remote Similarity NPC80809
0.6917 Remote Similarity NPC223741
0.6917 Remote Similarity NPC103298
0.6917 Remote Similarity NPC85593
0.6917 Remote Similarity NPC475331
0.6917 Remote Similarity NPC475585
0.6917 Remote Similarity NPC288502
0.6917 Remote Similarity NPC475335
0.6917 Remote Similarity NPC473577

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC471120 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
0.7031 Intermediate Similarity NPD6909 Approved
0.7031 Intermediate Similarity NPD6908 Approved
0.6829 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6822 Remote Similarity NPD6319 Approved
0.68 Remote Similarity NPD8297 Approved
0.6719 Remote Similarity NPD7115 Discovery
0.6719 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6643 Remote Similarity NPD6333 Approved
0.6643 Remote Similarity NPD6334 Approved
0.6642 Remote Similarity NPD8074 Phase 3
0.6641 Remote Similarity NPD6921 Approved
0.6585 Remote Similarity NPD6675 Approved
0.6585 Remote Similarity NPD7128 Approved
0.6585 Remote Similarity NPD6402 Approved
0.6585 Remote Similarity NPD5739 Approved
0.6583 Remote Similarity NPD8418 Phase 2
0.656 Remote Similarity NPD6372 Approved
0.656 Remote Similarity NPD4061 Clinical (unspecified phase)
0.656 Remote Similarity NPD6373 Approved
0.6541 Remote Similarity NPD7604 Phase 2
0.6519 Remote Similarity NPD8293 Discontinued
0.65 Remote Similarity NPD7638 Approved
0.6496 Remote Similarity NPD6399 Phase 3
0.6493 Remote Similarity NPD7492 Approved
0.6484 Remote Similarity NPD8298 Phase 2
0.6484 Remote Similarity NPD4632 Approved
0.648 Remote Similarity NPD6881 Approved
0.648 Remote Similarity NPD7320 Approved
0.648 Remote Similarity NPD6899 Approved
0.6471 Remote Similarity NPD7736 Approved
0.6457 Remote Similarity NPD6649 Approved
0.6457 Remote Similarity NPD6650 Approved
0.6457 Remote Similarity NPD8130 Phase 1
0.6446 Remote Similarity NPD7640 Approved
0.6446 Remote Similarity NPD7639 Approved
0.6444 Remote Similarity NPD6616 Approved
0.6439 Remote Similarity NPD6059 Approved
0.6439 Remote Similarity NPD6054 Approved
0.6423 Remote Similarity NPD7319 Approved
0.641 Remote Similarity NPD6411 Approved
0.6406 Remote Similarity NPD6882 Approved
0.64 Remote Similarity NPD5701 Approved
0.64 Remote Similarity NPD5697 Approved
0.6397 Remote Similarity NPD7078 Approved
0.6378 Remote Similarity NPD5955 Clinical (unspecified phase)
0.6378 Remote Similarity NPD7102 Approved
0.6378 Remote Similarity NPD7290 Approved
0.6378 Remote Similarity NPD6883 Approved
0.6364 Remote Similarity NPD4225 Approved
0.6349 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6343 Remote Similarity NPD6370 Approved
0.6341 Remote Similarity NPD7632 Discontinued
0.6336 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6328 Remote Similarity NPD6869 Approved
0.6328 Remote Similarity NPD6617 Approved
0.6328 Remote Similarity NPD6847 Approved
0.6324 Remote Similarity NPD7507 Approved
0.632 Remote Similarity NPD5357 Phase 1
0.6311 Remote Similarity NPD6404 Discontinued
0.6299 Remote Similarity NPD6013 Approved
0.6299 Remote Similarity NPD6014 Approved
0.6299 Remote Similarity NPD6012 Approved
0.6296 Remote Similarity NPD8328 Phase 3
0.6286 Remote Similarity NPD8338 Approved
0.6281 Remote Similarity NPD6084 Phase 2
0.6281 Remote Similarity NPD6083 Phase 2
0.6271 Remote Similarity NPD8034 Phase 2
0.6271 Remote Similarity NPD8035 Phase 2
0.6269 Remote Similarity NPD6016 Approved
0.6269 Remote Similarity NPD8033 Approved
0.6269 Remote Similarity NPD6015 Approved
0.626 Remote Similarity NPD4159 Approved
0.625 Remote Similarity NPD4634 Approved
0.625 Remote Similarity NPD5695 Phase 3
0.625 Remote Similarity NPD6421 Discontinued
0.6241 Remote Similarity NPD7516 Approved
0.6239 Remote Similarity NPD5764 Clinical (unspecified phase)
0.6239 Remote Similarity NPD6101 Approved
0.6239 Remote Similarity NPD5328 Approved
0.6232 Remote Similarity NPD8337 Approved
0.6232 Remote Similarity NPD8336 Approved
0.6231 Remote Similarity NPD8133 Approved
0.6228 Remote Similarity NPD4786 Approved
0.6222 Remote Similarity NPD5988 Approved
0.622 Remote Similarity NPD6011 Approved
0.6218 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6214 Remote Similarity NPD7260 Phase 2
0.6212 Remote Similarity NPD6009 Approved
0.6202 Remote Similarity NPD6401 Clinical (unspecified phase)
0.6194 Remote Similarity NPD8377 Approved
0.6194 Remote Similarity NPD8294 Approved
0.619 Remote Similarity NPD6008 Approved
0.6174 Remote Similarity NPD7625 Phase 1
0.6174 Remote Similarity NPD7520 Clinical (unspecified phase)
0.617 Remote Similarity NPD6845 Suspended
0.6167 Remote Similarity NPD7748 Approved
0.6165 Remote Similarity NPD7328 Approved
0.6165 Remote Similarity NPD7327 Approved
0.6148 Remote Similarity NPD5983 Phase 2
0.6148 Remote Similarity NPD8296 Approved
0.6148 Remote Similarity NPD8380 Approved
0.6148 Remote Similarity NPD8335 Approved
0.6148 Remote Similarity NPD8379 Approved
0.6148 Remote Similarity NPD4755 Approved
0.6148 Remote Similarity NPD8378 Approved
0.6148 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6143 Remote Similarity NPD6914 Discontinued
0.6142 Remote Similarity NPD6412 Phase 2
0.6142 Remote Similarity NPD5954 Clinical (unspecified phase)
0.6134 Remote Similarity NPD7637 Suspended
0.6134 Remote Similarity NPD6079 Approved
0.6106 Remote Similarity NPD1448 Clinical (unspecified phase)
0.6103 Remote Similarity NPD8080 Discontinued
0.6094 Remote Similarity NPD8174 Phase 2
0.6087 Remote Similarity NPD6336 Discontinued
0.6083 Remote Similarity NPD5778 Approved
0.6083 Remote Similarity NPD5779 Approved
0.6077 Remote Similarity NPD1719 Phase 1
0.6068 Remote Similarity NPD7524 Approved
0.6063 Remote Similarity NPD6640 Phase 3
0.6053 Remote Similarity NPD3667 Approved
0.6048 Remote Similarity NPD5286 Approved
0.6048 Remote Similarity NPD4700 Approved
0.6048 Remote Similarity NPD4696 Approved
0.6048 Remote Similarity NPD5285 Approved
0.6042 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6029 Remote Similarity NPD8517 Approved
0.6029 Remote Similarity NPD7503 Approved
0.6029 Remote Similarity NPD8515 Approved
0.6029 Remote Similarity NPD8513 Phase 3
0.6029 Remote Similarity NPD8516 Approved
0.6018 Remote Similarity NPD7525 Registered
0.6018 Remote Similarity NPD4748 Discontinued
0.6017 Remote Similarity NPD4264 Clinical (unspecified phase)
0.6016 Remote Similarity NPD7902 Approved
0.6015 Remote Similarity NPD6274 Approved
0.6 Remote Similarity NPD7100 Approved
0.6 Remote Similarity NPD7101 Approved
0.6 Remote Similarity NPD6033 Approved
0.6 Remote Similarity NPD7515 Phase 2
0.5983 Remote Similarity NPD3618 Phase 1
0.5982 Remote Similarity NPD6118 Approved
0.5982 Remote Similarity NPD6697 Approved
0.5982 Remote Similarity NPD6114 Approved
0.5982 Remote Similarity NPD6115 Approved
0.5972 Remote Similarity NPD8415 Approved
0.5969 Remote Similarity NPD6686 Approved
0.5968 Remote Similarity NPD5696 Approved
0.5952 Remote Similarity NPD5211 Phase 2
0.5952 Remote Similarity NPD5225 Approved
0.5952 Remote Similarity NPD5224 Approved
0.5952 Remote Similarity NPD3653 Clinical (unspecified phase)
0.5952 Remote Similarity NPD5226 Approved
0.5952 Remote Similarity NPD4633 Approved
0.595 Remote Similarity NPD4202 Approved
0.5946 Remote Similarity NPD6117 Approved
0.5942 Remote Similarity NPD7122 Discontinued
0.5938 Remote Similarity NPD4767 Approved
0.5938 Remote Similarity NPD4768 Approved
0.5935 Remote Similarity NPD4697 Phase 3
0.5935 Remote Similarity NPD5220 Clinical (unspecified phase)
0.5935 Remote Similarity NPD5222 Approved
0.5935 Remote Similarity NPD5221 Approved
0.5926 Remote Similarity NPD6335 Approved
0.5917 Remote Similarity NPD3168 Discontinued
0.5909 Remote Similarity NPD6053 Discontinued
0.5906 Remote Similarity NPD5174 Approved
0.5906 Remote Similarity NPD5175 Approved
0.5902 Remote Similarity NPD5707 Approved
0.5899 Remote Similarity NPD8342 Approved
0.5899 Remote Similarity NPD8299 Approved
0.5899 Remote Similarity NPD8340 Approved
0.5899 Remote Similarity NPD8341 Approved
0.5896 Remote Similarity NPD6868 Approved
0.5893 Remote Similarity NPD6116 Phase 1
0.5887 Remote Similarity NPD5173 Approved
0.5882 Remote Similarity NPD5737 Approved
0.5882 Remote Similarity NPD6672 Approved
0.5878 Remote Similarity NPD6420 Discontinued
0.5873 Remote Similarity NPD5223 Approved
0.5868 Remote Similarity NPD7983 Approved
0.5859 Remote Similarity NPD5141 Approved
0.5857 Remote Similarity NPD8451 Approved
0.5856 Remote Similarity NPD7339 Approved
0.5856 Remote Similarity NPD6942 Approved
0.5854 Remote Similarity NPD6356 Clinical (unspecified phase)
0.5852 Remote Similarity NPD6317 Approved
0.5847 Remote Similarity NPD7334 Approved
0.5847 Remote Similarity NPD7146 Approved
0.5847 Remote Similarity NPD6684 Approved
0.5847 Remote Similarity NPD5330 Approved
0.5847 Remote Similarity NPD7521 Approved
0.5847 Remote Similarity NPD6409 Approved
0.5847 Remote Similarity NPD3574 Clinical (unspecified phase)
0.5846 Remote Similarity NPD4729 Approved
0.5846 Remote Similarity NPD4730 Approved
0.5833 Remote Similarity NPD4753 Phase 2
0.5833 Remote Similarity NPD8449 Approved
0.5816 Remote Similarity NPD8448 Approved
0.5809 Remote Similarity NPD6313 Approved

Structure

External Identifiers

PubChem CID   14506477
ChEMBL   CHEMBL2375638
ZINC  

Physicochemical Properties

Molecular Weight:  707.46
ALogP:  0.4559
MLogP:  4.54
XLogP:  3.533
# Rotatable Bonds:  30
Polar Surface Area:  186.34
# H-Bond Aceptor:  11
# H-Bond Donor:  6
# Rings:  4
# Heavy Atoms:  50

Download Data

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