Natural Product: NPC205176

Natural Product ID:  NPC205176
Common Name:   Antillatoxin
IUPAC Name:   (6S,9S,14R,15R)-7,9,14-trimethyl-13-methylidene-6-propan-2-yl-15-[(2E,4E)-4,6,6-trimethylhepta-2,4-dien-2-yl]-1-oxa-4,7,10-triazacyclopentadecane-2,5,8,11-tetrone
Synonyms:   (4R,5R)-Antillatoxin; Antillatoxin
Molecular Formula:   C28H45N3O5
Standard InCHIKey:  WNMROEVYEZDXEL-OITYILOZSA-N
Standard InCHI:  InChI=1S/C28H45N3O5/c1-16(2)24-26(34)29-15-23(33)36-25(19(5)12-17(3)14-28(8,9)10)20(6)18(4)13-22(32)30-21(7)27(35)31(24)11/h12,14,16,20-21,24-25H,4,13,15H2,1-3,5-11H3,(H,29,34)(H,30,32)/b17-14+,19-12+/t20-,21+,24+,25+/m1/s1
Canonical SMILES:  O=C1CN=C(O)[C@H](C(C)C)N(C)C(=O)[C@@H](N=C(CC(=C)[C@H]([C@@H](O1)/C(=C/C(=C/C(C)(C)C)/C)/C)C)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
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria Caribbean PMID[8699186]
NPO26389 Lyngbya majuscula Species Oscillatoriaceae Bacteria PMID[11473443]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2 Others Unspecified EC50 = 180 nM 18157122
NPT1042 Organism Carassius auratus Carassius auratus LC50 = 100 nM 18157122
NPT1042 Organism Carassius auratus Carassius auratus LC50 = 0.05 ug/ml 19391605
NPT1042 Organism Carassius auratus Carassius auratus Activity = 0.1 nM 18625771
NPT1042 Organism Carassius auratus Carassius auratus LD50 = 0.05 ug/ml 8759172

  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 NPC205176 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
0.7805 Intermediate Similarity NPC246079
0.7788 Intermediate Similarity NPC103391
0.7788 Intermediate Similarity NPC472536
0.7105 Intermediate Similarity NPC171734
0.7069 Intermediate Similarity NPC476875
0.7049 Intermediate Similarity NPC273185
0.7008 Intermediate Similarity NPC120335
0.6964 Remote Similarity NPC474244
0.6881 Remote Similarity NPC469739
0.6847 Remote Similarity NPC475758
0.6814 Remote Similarity NPC475149
0.6814 Remote Similarity NPC471097
0.6786 Remote Similarity NPC13175
0.6786 Remote Similarity NPC475791
0.6757 Remote Similarity NPC52820
0.6754 Remote Similarity NPC476877
0.6726 Remote Similarity NPC188785
0.6699 Remote Similarity NPC474312
0.6695 Remote Similarity NPC251122
0.6667 Remote Similarity NPC474099
0.6641 Remote Similarity NPC329919
0.6641 Remote Similarity NPC477793
0.6639 Remote Similarity NPC29501
0.6638 Remote Similarity NPC476876
0.656 Remote Similarity NPC315188
0.6552 Remote Similarity NPC469604
0.6531 Remote Similarity NPC477086
0.6531 Remote Similarity NPC477087
0.6519 Remote Similarity NPC127741
0.65 Remote Similarity NPC135121
0.6491 Remote Similarity NPC233932
0.6484 Remote Similarity NPC309525
0.6475 Remote Similarity NPC471645
0.6475 Remote Similarity NPC266741
0.6475 Remote Similarity NPC477217
0.6475 Remote Similarity NPC201244
0.6475 Remote Similarity NPC474984
0.6466 Remote Similarity NPC55336
0.6466 Remote Similarity NPC199831
0.6466 Remote Similarity NPC474828
0.6466 Remote Similarity NPC474827
0.6466 Remote Similarity NPC68001
0.6465 Remote Similarity NPC477085
0.6452 Remote Similarity NPC9714
0.6442 Remote Similarity NPC184473
0.6441 Remote Similarity NPC315426
0.6429 Remote Similarity NPC81026
0.641 Remote Similarity NPC74035
0.6404 Remote Similarity NPC220234
0.6397 Remote Similarity NPC471265
0.6397 Remote Similarity NPC471264
0.6397 Remote Similarity NPC68865
0.6393 Remote Similarity NPC273814
0.6378 Remote Similarity NPC476183
0.6372 Remote Similarity NPC175614
0.6364 Remote Similarity NPC475608
0.6364 Remote Similarity NPC21713
0.6331 Remote Similarity NPC161069
0.6328 Remote Similarity NPC476184
0.6328 Remote Similarity NPC476281
0.6316 Remote Similarity NPC4834
0.6311 Remote Similarity NPC478024
0.6311 Remote Similarity NPC474995
0.6304 Remote Similarity NPC163392
0.6304 Remote Similarity NPC239762
0.6303 Remote Similarity NPC271562
0.6299 Remote Similarity NPC242692
0.6286 Remote Similarity NPC6902
0.6283 Remote Similarity NPC189764
0.6281 Remote Similarity NPC469603
0.6268 Remote Similarity NPC145113
0.626 Remote Similarity NPC193471
0.626 Remote Similarity NPC130124
0.6259 Remote Similarity NPC168113
0.6259 Remote Similarity NPC269398
0.6259 Remote Similarity NPC469427
0.6259 Remote Similarity NPC469426
0.6259 Remote Similarity NPC263493
0.625 Remote Similarity NPC207820
0.625 Remote Similarity NPC472458
0.625 Remote Similarity NPC38172
0.6241 Remote Similarity NPC5620
0.6239 Remote Similarity NPC5864
0.6239 Remote Similarity NPC124554
0.6239 Remote Similarity NPC301148
0.6233 Remote Similarity NPC470902
0.6231 Remote Similarity NPC476278
0.623 Remote Similarity NPC316984
0.623 Remote Similarity NPC30911
0.6228 Remote Similarity NPC475503
0.6218 Remote Similarity NPC475918
0.6214 Remote Similarity NPC197682
0.6214 Remote Similarity NPC139326
0.6214 Remote Similarity NPC84360
0.6214 Remote Similarity NPC176226
0.6207 Remote Similarity NPC474985
0.6198 Remote Similarity NPC329305
0.6183 Remote Similarity NPC476260
0.6183 Remote Similarity NPC476241
0.6172 Remote Similarity NPC23963
0.617 Remote Similarity NPC476978
0.6164 Remote Similarity NPC473341
0.6162 Remote Similarity NPC45060
0.6162 Remote Similarity NPC280065
0.6162 Remote Similarity NPC101622
0.6161 Remote Similarity NPC471098
0.6161 Remote Similarity NPC173763
0.6161 Remote Similarity NPC62263
0.6154 Remote Similarity NPC252878
0.6154 Remote Similarity NPC225648
0.6154 Remote Similarity NPC329761
0.6154 Remote Similarity NPC138775
0.6148 Remote Similarity NPC120420
0.614 Remote Similarity NPC205546
0.614 Remote Similarity NPC233273
0.614 Remote Similarity NPC150041
0.614 Remote Similarity NPC50902
0.6139 Remote Similarity NPC43219
0.6138 Remote Similarity NPC475168
0.6138 Remote Similarity NPC7817
0.6136 Remote Similarity NPC476125
0.6136 Remote Similarity NPC476179
0.6134 Remote Similarity NPC64168
0.6134 Remote Similarity NPC124549
0.6132 Remote Similarity NPC8538
0.6132 Remote Similarity NPC184208
0.6132 Remote Similarity NPC284456
0.6127 Remote Similarity NPC316008
0.6127 Remote Similarity NPC313867
0.6127 Remote Similarity NPC209509
0.6126 Remote Similarity NPC474593
0.6126 Remote Similarity NPC475801
0.6126 Remote Similarity NPC81195
0.6122 Remote Similarity NPC39431
0.6116 Remote Similarity NPC67009
0.6116 Remote Similarity NPC287572
0.6116 Remote Similarity NPC471636
0.6115 Remote Similarity NPC92784
0.6115 Remote Similarity NPC476133
0.6115 Remote Similarity NPC470884
0.6115 Remote Similarity NPC178662
0.6115 Remote Similarity NPC98424
0.6111 Remote Similarity NPC65045
0.6111 Remote Similarity NPC475642
0.6107 Remote Similarity NPC46427
0.6103 Remote Similarity NPC99864
0.6102 Remote Similarity NPC473289
0.61 Remote Similarity NPC4299
0.6098 Remote Similarity NPC168758
0.6098 Remote Similarity NPC181510
0.6098 Remote Similarity NPC47857
0.6095 Remote Similarity NPC477088
0.6091 Remote Similarity NPC199382
0.6087 Remote Similarity NPC197294
0.6087 Remote Similarity NPC8098
0.6087 Remote Similarity NPC45313
0.6087 Remote Similarity NPC183449
0.6084 Remote Similarity NPC314358
0.6083 Remote Similarity NPC154601
0.6083 Remote Similarity NPC271269
0.6078 Remote Similarity NPC86064
0.6077 Remote Similarity NPC202521
0.6071 Remote Similarity NPC476259
0.6071 Remote Similarity NPC307357
0.6071 Remote Similarity NPC47230
0.6071 Remote Similarity NPC46098
0.6071 Remote Similarity NPC474576
0.6071 Remote Similarity NPC17143
0.6071 Remote Similarity NPC268841
0.6069 Remote Similarity NPC129666
0.6068 Remote Similarity NPC26597
0.6066 Remote Similarity NPC474891
0.6063 Remote Similarity NPC201889
0.6063 Remote Similarity NPC235625
0.6063 Remote Similarity NPC106791
0.6063 Remote Similarity NPC284656
0.6063 Remote Similarity NPC470544
0.6061 Remote Similarity NPC314282
0.6061 Remote Similarity NPC204556
0.6061 Remote Similarity NPC473249
0.6056 Remote Similarity NPC315283
0.6056 Remote Similarity NPC314388
0.605 Remote Similarity NPC279833
0.605 Remote Similarity NPC80439
0.605 Remote Similarity NPC198344
0.605 Remote Similarity NPC173690
0.605 Remote Similarity NPC6271
0.6048 Remote Similarity NPC469968
0.6048 Remote Similarity NPC80834
0.6045 Remote Similarity NPC319766
0.604 Remote Similarity NPC477084
0.6036 Remote Similarity NPC155230
0.6034 Remote Similarity NPC476344
0.6034 Remote Similarity NPC475646
0.6032 Remote Similarity NPC477554
0.6031 Remote Similarity NPC160493
0.6018 Remote Similarity NPC319473
0.6017 Remote Similarity NPC474873
0.6017 Remote Similarity NPC313234
0.6016 Remote Similarity NPC470545

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC205176 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
0.6746 Remote Similarity NPD8273 Phase 1
0.6695 Remote Similarity NPD6421 Discontinued
0.6471 Remote Similarity NPD6413 Approved
0.623 Remote Similarity NPD2204 Approved
0.6228 Remote Similarity NPD4228 Discovery
0.6216 Remote Similarity NPD6095 Approved
0.6216 Remote Similarity NPD6094 Approved
0.6176 Remote Similarity NPD8387 Clinical (unspecified phase)
0.617 Remote Similarity NPD6681 Discovery
0.6148 Remote Similarity NPD6919 Clinical (unspecified phase)
0.6107 Remote Similarity NPD8451 Approved
0.6106 Remote Similarity NPD5781 Clinical (unspecified phase)
0.6103 Remote Similarity NPD8415 Approved
0.6063 Remote Similarity NPD5292 Approved
0.6063 Remote Similarity NPD5291 Approved
0.6061 Remote Similarity NPD7747 Phase 1
0.6061 Remote Similarity NPD7746 Phase 1
0.6061 Remote Similarity NPD8448 Approved
0.6045 Remote Similarity NPD8391 Approved
0.6045 Remote Similarity NPD8392 Approved
0.6045 Remote Similarity NPD8390 Approved
0.5985 Remote Similarity NPD2584 Suspended
0.595 Remote Similarity NPD4211 Phase 1
0.5938 Remote Similarity NPD7641 Discontinued
0.5929 Remote Similarity NPD7838 Discovery
0.5929 Remote Similarity NPD8173 Phase 2
0.5929 Remote Similarity NPD8172 Phase 2
0.5923 Remote Similarity NPD7739 Clinical (unspecified phase)
0.5917 Remote Similarity NPD2258 Approved
0.5917 Remote Similarity NPD2259 Approved
0.5909 Remote Similarity NPD3723 Clinical (unspecified phase)
0.5909 Remote Similarity NPD8299 Approved
0.5909 Remote Similarity NPD8341 Approved
0.5909 Remote Similarity NPD8340 Approved
0.5909 Remote Similarity NPD8342 Approved
0.5903 Remote Similarity NPD6860 Clinical (unspecified phase)
0.5878 Remote Similarity NPD7624 Clinical (unspecified phase)
0.5878 Remote Similarity NPD7623 Phase 3
0.5873 Remote Similarity NPD1376 Discontinued
0.5865 Remote Similarity NPD1452 Discontinued
0.5859 Remote Similarity NPD7505 Discontinued
0.5859 Remote Similarity NPD7500 Approved
0.5845 Remote Similarity NPD8384 Approved
0.5822 Remote Similarity NPD8323 Discontinued
0.582 Remote Similarity NPD6640 Phase 3
0.582 Remote Similarity NPD7333 Discontinued
0.582 Remote Similarity NPD5357 Phase 1
0.5814 Remote Similarity NPD2099 Approved
0.5789 Remote Similarity NPD8522 Clinical (unspecified phase)
0.5778 Remote Similarity NPD3125 Approved
0.5772 Remote Similarity NPD2147 Approved
0.5745 Remote Similarity NPD7113 Clinical (unspecified phase)
0.5743 Remote Similarity NPD3724 Clinical (unspecified phase)
0.5735 Remote Similarity NPD2585 Clinical (unspecified phase)
0.5734 Remote Similarity NPD3480 Approved
0.5724 Remote Similarity NPD6119 Clinical (unspecified phase)
0.5724 Remote Similarity NPD2891 Approved
0.5714 Remote Similarity NPD7642 Approved
0.5714 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5703 Remote Similarity NPD2100 Approved
0.5693 Remote Similarity NPD3608 Clinical (unspecified phase)
0.5683 Remote Similarity NPD2049 Clinical (unspecified phase)
0.5683 Remote Similarity NPD2043 Approved
0.5683 Remote Similarity NPD21 Approved
0.5683 Remote Similarity NPD2046 Approved
0.5683 Remote Similarity NPD2044 Approved
0.5683 Remote Similarity NPD2047 Approved
0.5683 Remote Similarity NPD2050 Clinical (unspecified phase)
0.5683 Remote Similarity NPD2051 Approved
0.5683 Remote Similarity NPD2048 Approved
0.5683 Remote Similarity NPD2045 Approved
0.5678 Remote Similarity NPD7839 Suspended
0.5674 Remote Similarity NPD8416 Discontinued
0.5669 Remote Similarity NPD2090 Approved
0.5652 Remote Similarity NPD46 Approved
0.5652 Remote Similarity NPD4175 Approved
0.5652 Remote Similarity NPD6698 Approved
0.5652 Remote Similarity NPD4177 Approved
0.5635 Remote Similarity NPD6420 Discontinued
0.5629 Remote Similarity NPD7131 Phase 3
0.5615 Remote Similarity NPD961 Discontinued
0.5606 Remote Similarity NPD7299 Clinical (unspecified phase)
0.5603 Remote Similarity NPD7983 Approved

Structure

External Identifiers

PubChem CID   10051827
ChEMBL   CHEMBL464946
ZINC  

Physicochemical Properties

Molecular Weight:  503.34
ALogP:  3.3357
MLogP:  3.66
XLogP:  3.826
# Rotatable Bonds:  16
Polar Surface Area:  111.79
# H-Bond Aceptor:  8
# H-Bond Donor:  2
# Rings:  1
# Heavy Atoms:  36

Download Data

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