Natural Product: NPC474873

Natural Product ID:  NPC474873
Common Name:   Latrunculin C
IUPAC Name:   (4R)-4-[1-hydroxy-2-[(2R,4R,7S,8Z,12Z)-4-hydroxy-7,12-dimethyl-14-oxo-1-oxacyclotetradeca-8,12-dien-2-yl]ethyl]-1,3-thiazolidin-2-one
Synonyms:   Latrunculin C
Molecular Formula:   C20H31NO5S
Standard InCHIKey:  JDROCHDFKUSVDQ-CNUXZQNMSA-N
Standard InCHI:  InChI=1S/C20H31NO5S/c1-13-5-3-4-6-14(2)9-19(24)26-16(10-15(22)8-7-13)11-18(23)17-12-27-20(25)21-17/h3,5,9,13,15-18,22-23H,4,6-8,10-12H2,1-2H3,(H,21,25)/b5-3-,14-9-/t13-,15-,16-,17+,18?/m1/s1
Canonical SMILES:  O[C@@H]1CC[C@H](C)/C=CCC/C(=CC(=O)O[C@H](C1)CC([C@@H]1CSC(=N1)O)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
NPO19376 Cacospongia mycofijiensis Species Thorectidae Eukaryota PMID[18942825]
NPO3492 Negombata magnifica Species Latrunculiidae Eukaryota PMID[18942825]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT400 Cell Line MDA-MB-435 Homo sapiens IC50 = 34300 nM 16933872
NPT400 Cell Line MDA-MB-435 Homo sapiens Ratio IC50 < 0.3 10.6019/CHEMBL1201861
NPT393 Cell Line HCT-116 Homo sapiens IC50 > 100000 nM 12141877

  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 NPC474873 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
0.9388 High Similarity NPC135216
0.9388 High Similarity NPC101106
0.93 High Similarity NPC474891
0.92 High Similarity NPC287572
0.92 High Similarity NPC471636
0.91 High Similarity NPC250187
0.9029 High Similarity NPC273215
0.9029 High Similarity NPC279383
0.9029 High Similarity NPC295444
0.9029 High Similarity NPC268327
0.902 High Similarity NPC127578
0.901 High Similarity NPC476034
0.901 High Similarity NPC474969
0.8762 High Similarity NPC475988
0.8426 Intermediate Similarity NPC477554
0.8349 Intermediate Similarity NPC477553
0.8273 Intermediate Similarity NPC477555
0.8148 Intermediate Similarity NPC474995
0.7838 Intermediate Similarity NPC474984
0.7241 Intermediate Similarity NPC201968
0.7232 Intermediate Similarity NPC329305
0.7217 Intermediate Similarity NPC50694
0.7018 Intermediate Similarity NPC122926
0.7018 Intermediate Similarity NPC113012
0.7 Intermediate Similarity NPC477557
0.6804 Remote Similarity NPC469880
0.6789 Remote Similarity NPC4834
0.6667 Remote Similarity NPC29501
0.6667 Remote Similarity NPC474985
0.6642 Remote Similarity NPC477556
0.6633 Remote Similarity NPC477202
0.66 Remote Similarity NPC139712
0.6566 Remote Similarity NPC477203
0.6486 Remote Similarity NPC476344
0.6481 Remote Similarity NPC319473
0.6471 Remote Similarity NPC315731
0.6471 Remote Similarity NPC184208
0.6471 Remote Similarity NPC8538
0.6455 Remote Similarity NPC150041
0.6436 Remote Similarity NPC226226
0.6436 Remote Similarity NPC55304
0.6435 Remote Similarity NPC477000
0.6435 Remote Similarity NPC14537
0.6435 Remote Similarity NPC477001
0.6429 Remote Similarity NPC234542
0.6396 Remote Similarity NPC475503
0.6396 Remote Similarity NPC175614
0.6389 Remote Similarity NPC473448
0.6379 Remote Similarity NPC473252
0.6372 Remote Similarity NPC473224
0.6355 Remote Similarity NPC193386
0.6354 Remote Similarity NPC101622
0.6346 Remote Similarity NPC474809
0.6339 Remote Similarity NPC475646
0.6337 Remote Similarity NPC474833
0.633 Remote Similarity NPC472264
0.6327 Remote Similarity NPC477085
0.6316 Remote Similarity NPC175531
0.6316 Remote Similarity NPC472266
0.6311 Remote Similarity NPC475944
0.6303 Remote Similarity NPC477997
0.6296 Remote Similarity NPC133450
0.6293 Remote Similarity NPC74035
0.6293 Remote Similarity NPC75523
0.6289 Remote Similarity NPC4299
0.6286 Remote Similarity NPC78673
0.6286 Remote Similarity NPC186155
0.6286 Remote Similarity NPC160517
0.6262 Remote Similarity NPC471796
0.6262 Remote Similarity NPC199382
0.6261 Remote Similarity NPC72401
0.6261 Remote Similarity NPC325339
0.6261 Remote Similarity NPC473289
0.6239 Remote Similarity NPC154601
0.6239 Remote Similarity NPC177668
0.6238 Remote Similarity NPC84360
0.6226 Remote Similarity NPC67081
0.6226 Remote Similarity NPC471494
0.6226 Remote Similarity NPC471223
0.6224 Remote Similarity NPC477087
0.6224 Remote Similarity NPC477086
0.6207 Remote Similarity NPC474563
0.62 Remote Similarity NPC329852
0.6198 Remote Similarity NPC469865
0.6195 Remote Similarity NPC52820
0.619 Remote Similarity NPC311070
0.6186 Remote Similarity NPC475004
0.6176 Remote Similarity NPC474816
0.6176 Remote Similarity NPC209135
0.6174 Remote Similarity NPC316250
0.6168 Remote Similarity NPC61527
0.6168 Remote Similarity NPC311163
0.6168 Remote Similarity NPC131813
0.6162 Remote Similarity NPC329914
0.6162 Remote Similarity NPC185186
0.6162 Remote Similarity NPC329890
0.6162 Remote Similarity NPC327383
0.6154 Remote Similarity NPC112868
0.6154 Remote Similarity NPC64168
0.6147 Remote Similarity NPC159369
0.6147 Remote Similarity NPC39290
0.6147 Remote Similarity NPC295312
0.614 Remote Similarity NPC132931
0.614 Remote Similarity NPC270813
0.6134 Remote Similarity NPC140251
0.6134 Remote Similarity NPC307903
0.6129 Remote Similarity NPC147707
0.6129 Remote Similarity NPC65045
0.6121 Remote Similarity NPC474244
0.6117 Remote Similarity NPC477088
0.6117 Remote Similarity NPC86971
0.6111 Remote Similarity NPC313658
0.6111 Remote Similarity NPC316138
0.6111 Remote Similarity NPC160138
0.6102 Remote Similarity NPC475918
0.6102 Remote Similarity NPC271269
0.6102 Remote Similarity NPC472433
0.61 Remote Similarity NPC477204
0.61 Remote Similarity NPC470686
0.6098 Remote Similarity NPC471645
0.6095 Remote Similarity NPC471298
0.6095 Remote Similarity NPC474312
0.6091 Remote Similarity NPC3952
0.6091 Remote Similarity NPC319021
0.6091 Remote Similarity NPC475855
0.6083 Remote Similarity NPC473578
0.6082 Remote Similarity NPC474823
0.6082 Remote Similarity NPC474812
0.608 Remote Similarity NPC201889
0.608 Remote Similarity NPC235625
0.608 Remote Similarity NPC106791
0.6078 Remote Similarity NPC262747
0.6078 Remote Similarity NPC315394
0.6075 Remote Similarity NPC471795
0.6071 Remote Similarity NPC256368
0.6068 Remote Similarity NPC173690
0.6068 Remote Similarity NPC6271
0.6068 Remote Similarity NPC80439
0.6068 Remote Similarity NPC279833
0.6061 Remote Similarity NPC316185
0.6058 Remote Similarity NPC311369
0.6055 Remote Similarity NPC472810
0.6055 Remote Similarity NPC34754
0.6055 Remote Similarity NPC472378
0.6055 Remote Similarity NPC472809
0.605 Remote Similarity NPC315531
0.605 Remote Similarity NPC271562
0.604 Remote Similarity NPC327041
0.604 Remote Similarity NPC285840
0.6038 Remote Similarity NPC231601
0.6038 Remote Similarity NPC472377
0.6038 Remote Similarity NPC253801
0.6038 Remote Similarity NPC471297
0.6038 Remote Similarity NPC116543
0.6036 Remote Similarity NPC114172
0.6036 Remote Similarity NPC476075
0.6036 Remote Similarity NPC471324
0.6036 Remote Similarity NPC206679
0.6036 Remote Similarity NPC476084
0.6036 Remote Similarity NPC158061
0.6034 Remote Similarity NPC313234
0.6031 Remote Similarity NPC329919
0.6031 Remote Similarity NPC477793
0.602 Remote Similarity NPC151481
0.6019 Remote Similarity NPC305475
0.6019 Remote Similarity NPC469483
0.6019 Remote Similarity NPC47220
0.6019 Remote Similarity NPC475461
0.6019 Remote Similarity NPC261721
0.6019 Remote Similarity NPC186332
0.6018 Remote Similarity NPC304886
0.6018 Remote Similarity NPC276110
0.6017 Remote Similarity NPC205176
0.6016 Remote Similarity NPC130124
0.6016 Remote Similarity NPC193471
0.6 Remote Similarity NPC470734
0.6 Remote Similarity NPC475150
0.6 Remote Similarity NPC70235
0.6 Remote Similarity NPC160222
0.6 Remote Similarity NPC325031
0.6 Remote Similarity NPC193753
0.5984 Remote Similarity NPC12270
0.5984 Remote Similarity NPC47857
0.5984 Remote Similarity NPC475608
0.5984 Remote Similarity NPC181510
0.5984 Remote Similarity NPC168758
0.5984 Remote Similarity NPC21713
0.5982 Remote Similarity NPC159092
0.5982 Remote Similarity NPC475838
0.5982 Remote Similarity NPC152778
0.5982 Remote Similarity NPC162615
0.5982 Remote Similarity NPC228451
0.5982 Remote Similarity NPC109406
0.5982 Remote Similarity NPC125674
0.5982 Remote Similarity NPC205034
0.5981 Remote Similarity NPC477199
0.5981 Remote Similarity NPC163093
0.5981 Remote Similarity NPC471301
0.5981 Remote Similarity NPC82297
0.598 Remote Similarity NPC188860

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC474873 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
0.9388 High Similarity NPD4211 Phase 1
0.717 Intermediate Similarity NPD4228 Discovery
0.6807 Remote Similarity NPD7505 Discontinued
0.6496 Remote Similarity NPD6413 Approved
0.6239 Remote Similarity NPD6095 Approved
0.6239 Remote Similarity NPD6094 Approved
0.6167 Remote Similarity NPD6420 Discontinued
0.6167 Remote Similarity NPD6421 Discontinued
0.6126 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6091 Remote Similarity NPD7838 Discovery
0.6 Remote Similarity NPD5370 Suspended
0.5986 Remote Similarity NPD7625 Phase 1
0.5984 Remote Similarity NPD1719 Phase 1
0.5946 Remote Similarity NPD46 Approved
0.5946 Remote Similarity NPD6698 Approved
0.5932 Remote Similarity NPD2258 Approved
0.5932 Remote Similarity NPD2259 Approved
0.5893 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5887 Remote Similarity NPD1376 Discontinued
0.5854 Remote Similarity NPD2204 Approved
0.5833 Remote Similarity NPD777 Phase 3
0.5833 Remote Similarity NPD6400 Clinical (unspecified phase)
0.5802 Remote Similarity NPD4480 Approved
0.5773 Remote Similarity NPD2685 Clinical (unspecified phase)
0.5758 Remote Similarity NPD3677 Clinical (unspecified phase)
0.5741 Remote Similarity NPD7154 Phase 3
0.5725 Remote Similarity NPD7829 Approved
0.5725 Remote Similarity NPD7642 Approved
0.5725 Remote Similarity NPD7830 Approved
0.5724 Remote Similarity NPD7274 Clinical (unspecified phase)
0.5703 Remote Similarity NPD1773 Discontinued
0.5703 Remote Similarity NPD7641 Discontinued
0.5702 Remote Similarity NPD2251 Approved
0.5702 Remote Similarity NPD2252 Approved
0.5692 Remote Similarity NPD4209 Clinical (unspecified phase)
0.569 Remote Similarity NPD7839 Suspended
0.5664 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5659 Remote Similarity NPD3159 Discontinued
0.5639 Remote Similarity NPD8273 Phase 1
0.5639 Remote Similarity NPD2148 Clinical (unspecified phase)
0.5636 Remote Similarity NPD6082 Clinical (unspecified phase)
0.563 Remote Similarity NPD5344 Discontinued
0.5625 Remote Similarity NPD7500 Approved
0.5607 Remote Similarity NPD5790 Clinical (unspecified phase)
0.56 Remote Similarity NPD7116 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   44589658
ChEMBL   CHEMBL485924
ZINC  

Physicochemical Properties

Molecular Weight:  397.19
ALogP:  0.8319
MLogP:  2.89
XLogP:  3.39
# Rotatable Bonds:  8
Polar Surface Area:  124.65
# H-Bond Aceptor:  6
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  27

Download Data

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Structure MOL file  
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