Natural Product: NPC469869

Natural Product ID:  NPC469869
Common Name:   2-Epi-Lyngbyaloside
IUPAC Name:   (1R,2S,3S,5Z,7R,9R,12R,13S,15R)-9-[(1E,3E)-4-bromobuta-1,3-dienyl]-3,13-dihydroxy-2,7,12-trimethyl-15-[(2R,3R,4R,5S,6S)-3,4,5-trimethoxy-6-methyloxan-2-yl]oxy-10,17-dioxabicyclo[11.3.1]heptadec-5-en-11-one
Synonyms:   2-Epi-Lyngbyaloside
Molecular Formula:   C31H49BrO10
Standard InCHIKey:  RXKHKYLAQKUTIR-CZNUVGAJSA-N
Standard InCHI:  InChI=1S/C31H49BrO10/c1-18-11-10-13-24(33)19(2)25-16-23(41-30-28(38-7)27(37-6)26(36-5)21(4)39-30)17-31(35,42-25)20(3)29(34)40-22(15-18)12-8-9-14-32/h8-12,14,18-28,30,33,35H,13,15-17H2,1-7H3/b11-10-,12-8+,14-9+/t18-,19-,20-,21-,22-,23+,24-,25+,26-,27+,28+,30-,31-/m0/s1
Canonical SMILES:  Br/C=C/C=C/[C@H]1C[C@@H](C)/C=CC[C@H](O)[C@@H]([C@@H]2O[C@@]([C@H](C(=O)O1)C)(O)C[C@@H](C2)O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1OC)OC)OC)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
NPO30186 Lyngbya bouillonii Species Oscillatoriaceae Bacteria PMID[20704304]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT139 Cell Line HT-29 Homo sapiens IC50 = 38000 nM 15686905
NPT165 Cell Line HeLa Homo sapiens IC50 = 33000 nM 15686905

  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 NPC469869 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
0.9381 High Similarity NPC469871
0.9381 High Similarity NPC469870
0.8224 Intermediate Similarity NPC473807
0.8224 Intermediate Similarity NPC193765
0.8208 Intermediate Similarity NPC476740
0.8208 Intermediate Similarity NPC476738
0.819 Intermediate Similarity NPC473816
0.819 Intermediate Similarity NPC475367
0.819 Intermediate Similarity NPC309398
0.819 Intermediate Similarity NPC474581
0.8155 Intermediate Similarity NPC308567
0.8155 Intermediate Similarity NPC261377
0.8155 Intermediate Similarity NPC255592
0.8148 Intermediate Similarity NPC313668
0.8148 Intermediate Similarity NPC315836
0.8142 Intermediate Similarity NPC314268
0.8142 Intermediate Similarity NPC477515
0.8142 Intermediate Similarity NPC67917
0.8142 Intermediate Similarity NPC313802
0.81 Intermediate Similarity NPC472199
0.8058 Intermediate Similarity NPC472290
0.8053 Intermediate Similarity NPC13710
0.802 Intermediate Similarity NPC478037
0.802 Intermediate Similarity NPC478036
0.802 Intermediate Similarity NPC320089
0.8 Intermediate Similarity NPC313670
0.8 Intermediate Similarity NPC469812
0.8 Intermediate Similarity NPC473228
0.8 Intermediate Similarity NPC470829
0.8 Intermediate Similarity NPC183353
0.8 Intermediate Similarity NPC170880
0.7981 Intermediate Similarity NPC187761
0.7981 Intermediate Similarity NPC83895
0.7941 Intermediate Similarity NPC472198
0.7921 Intermediate Similarity NPC472197
0.7885 Intermediate Similarity NPC40812
0.7879 Intermediate Similarity NPC477959
0.7879 Intermediate Similarity NPC86005
0.7863 Intermediate Similarity NPC315783
0.783 Intermediate Similarity NPC154132
0.783 Intermediate Similarity NPC57586
0.783 Intermediate Similarity NPC2313
0.783 Intermediate Similarity NPC475655
0.783 Intermediate Similarity NPC471637
0.783 Intermediate Similarity NPC475157
0.7822 Intermediate Similarity NPC473311
0.7788 Intermediate Similarity NPC180722
0.7788 Intermediate Similarity NPC195645
0.7788 Intermediate Similarity NPC165332
0.7788 Intermediate Similarity NPC54731
0.7767 Intermediate Similarity NPC71589
0.7748 Intermediate Similarity NPC83005
0.7745 Intermediate Similarity NPC470379
0.7745 Intermediate Similarity NPC470373
0.7727 Intermediate Similarity NPC475960
0.7685 Intermediate Similarity NPC197736
0.767 Intermediate Similarity NPC238090
0.767 Intermediate Similarity NPC472195
0.767 Intermediate Similarity NPC472196
0.7667 Intermediate Similarity NPC314282
0.7653 Intermediate Similarity NPC156089
0.7653 Intermediate Similarity NPC473500
0.7653 Intermediate Similarity NPC470313
0.7653 Intermediate Similarity NPC38295
0.7624 Intermediate Similarity NPC473151
0.7619 Intermediate Similarity NPC306041
0.7619 Intermediate Similarity NPC143446
0.7596 Intermediate Similarity NPC294293
0.7596 Intermediate Similarity NPC5418
0.7596 Intermediate Similarity NPC159698
0.7593 Intermediate Similarity NPC473596
0.7593 Intermediate Similarity NPC313569
0.7586 Intermediate Similarity NPC475309
0.7573 Intermediate Similarity NPC9447
0.7547 Intermediate Similarity NPC266842
0.7545 Intermediate Similarity NPC315070
0.7544 Intermediate Similarity NPC75167
0.7544 Intermediate Similarity NPC311592
0.7525 Intermediate Similarity NPC316138
0.7525 Intermediate Similarity NPC313658
0.7524 Intermediate Similarity NPC170204
0.75 Intermediate Similarity NPC154127
0.75 Intermediate Similarity NPC313333
0.75 Intermediate Similarity NPC61201
0.75 Intermediate Similarity NPC313342
0.75 Intermediate Similarity NPC476611
0.75 Intermediate Similarity NPC314512
0.75 Intermediate Similarity NPC314451
0.7478 Intermediate Similarity NPC181145
0.7477 Intermediate Similarity NPC203627
0.7477 Intermediate Similarity NPC184512
0.7477 Intermediate Similarity NPC161855
0.7475 Intermediate Similarity NPC69469
0.7455 Intermediate Similarity NPC474917
0.7455 Intermediate Similarity NPC231271
0.7455 Intermediate Similarity NPC472748
0.7455 Intermediate Similarity NPC470519
0.7453 Intermediate Similarity NPC255410
0.7451 Intermediate Similarity NPC137368
0.7449 Intermediate Similarity NPC21693
0.7449 Intermediate Similarity NPC236649
0.7434 Intermediate Similarity NPC119550
0.7434 Intermediate Similarity NPC46407
0.7431 Intermediate Similarity NPC195510
0.7431 Intermediate Similarity NPC13171
0.7431 Intermediate Similarity NPC222062
0.7426 Intermediate Similarity NPC208473
0.7426 Intermediate Similarity NPC477993
0.7426 Intermediate Similarity NPC477994
0.7423 Intermediate Similarity NPC321728
0.7411 Intermediate Similarity NPC392
0.7411 Intermediate Similarity NPC177524
0.7411 Intermediate Similarity NPC219900
0.7387 Intermediate Similarity NPC252296
0.7387 Intermediate Similarity NPC472749
0.7387 Intermediate Similarity NPC478038
0.7387 Intermediate Similarity NPC472751
0.7383 Intermediate Similarity NPC476612
0.7383 Intermediate Similarity NPC278506
0.7383 Intermediate Similarity NPC120299
0.7383 Intermediate Similarity NPC476613
0.7379 Intermediate Similarity NPC118193
0.7379 Intermediate Similarity NPC256902
0.7373 Intermediate Similarity NPC122971
0.7368 Intermediate Similarity NPC126897
0.7368 Intermediate Similarity NPC297945
0.7364 Intermediate Similarity NPC472747
0.7364 Intermediate Similarity NPC267869
0.7364 Intermediate Similarity NPC472750
0.7364 Intermediate Similarity NPC118761
0.7364 Intermediate Similarity NPC284929
0.7364 Intermediate Similarity NPC234304
0.7364 Intermediate Similarity NPC197541
0.7358 Intermediate Similarity NPC36954
0.7358 Intermediate Similarity NPC300710
0.7358 Intermediate Similarity NPC469543
0.7353 Intermediate Similarity NPC74139
0.735 Intermediate Similarity NPC474483
0.7345 Intermediate Similarity NPC133625
0.7345 Intermediate Similarity NPC316974
0.7339 Intermediate Similarity NPC98859
0.7339 Intermediate Similarity NPC4637
0.7333 Intermediate Similarity NPC320552
0.7333 Intermediate Similarity NPC476300
0.7321 Intermediate Similarity NPC254538
0.7321 Intermediate Similarity NPC474285
0.732 Intermediate Similarity NPC127526
0.7315 Intermediate Similarity NPC472015
0.7315 Intermediate Similarity NPC198422
0.7315 Intermediate Similarity NPC40182
0.7315 Intermediate Similarity NPC475653
0.7311 Intermediate Similarity NPC48692
0.7308 Intermediate Similarity NPC327253
0.7308 Intermediate Similarity NPC202886
0.7308 Intermediate Similarity NPC6414
0.7308 Intermediate Similarity NPC316228
0.7308 Intermediate Similarity NPC303451
0.7304 Intermediate Similarity NPC174836
0.7297 Intermediate Similarity NPC264867
0.7297 Intermediate Similarity NPC201880
0.7297 Intermediate Similarity NPC473207
0.7297 Intermediate Similarity NPC81567
0.7297 Intermediate Similarity NPC470321
0.7297 Intermediate Similarity NPC239162
0.729 Intermediate Similarity NPC475525
0.729 Intermediate Similarity NPC473605
0.729 Intermediate Similarity NPC475241
0.729 Intermediate Similarity NPC173329
0.729 Intermediate Similarity NPC475375
0.729 Intermediate Similarity NPC475593
0.729 Intermediate Similarity NPC475164
0.729 Intermediate Similarity NPC473765
0.729 Intermediate Similarity NPC473291
0.729 Intermediate Similarity NPC476066
0.729 Intermediate Similarity NPC473859
0.729 Intermediate Similarity NPC288350
0.729 Intermediate Similarity NPC476315
0.729 Intermediate Similarity NPC475540
0.7288 Intermediate Similarity NPC473617
0.7288 Intermediate Similarity NPC473828
0.7288 Intermediate Similarity NPC109603
0.7288 Intermediate Similarity NPC93688
0.7273 Intermediate Similarity NPC201191
0.7273 Intermediate Similarity NPC314629
0.7273 Intermediate Similarity NPC472754
0.7265 Intermediate Similarity NPC277583
0.7264 Intermediate Similarity NPC256368
0.7257 Intermediate Similarity NPC48548
0.7257 Intermediate Similarity NPC128795
0.7257 Intermediate Similarity NPC311223
0.7257 Intermediate Similarity NPC217921
0.7257 Intermediate Similarity NPC135015
0.7255 Intermediate Similarity NPC164393
0.725 Intermediate Similarity NPC170084
0.725 Intermediate Similarity NPC476204
0.7248 Intermediate Similarity NPC244878
0.7248 Intermediate Similarity NPC324667
0.7248 Intermediate Similarity NPC255677
0.7248 Intermediate Similarity NPC475053
0.7248 Intermediate Similarity NPC306344

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469869 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
0.81 Intermediate Similarity NPD7983 Approved
0.8 Intermediate Similarity NPD8516 Approved
0.8 Intermediate Similarity NPD8515 Approved
0.8 Intermediate Similarity NPD8517 Approved
0.8 Intermediate Similarity NPD8513 Phase 3
0.7863 Intermediate Similarity NPD7830 Approved
0.7863 Intermediate Similarity NPD7829 Approved
0.781 Intermediate Similarity NPD8029 Clinical (unspecified phase)
0.7788 Intermediate Similarity NPD7839 Suspended
0.7731 Intermediate Similarity NPD8451 Approved
0.7692 Intermediate Similarity NPD8444 Approved
0.7667 Intermediate Similarity NPD8448 Approved
0.7647 Intermediate Similarity NPD46 Approved
0.7647 Intermediate Similarity NPD6698 Approved
0.75 Intermediate Similarity NPD8342 Approved
0.75 Intermediate Similarity NPD8341 Approved
0.75 Intermediate Similarity NPD8340 Approved
0.75 Intermediate Similarity NPD8299 Approved
0.75 Intermediate Similarity NPD5779 Approved
0.75 Intermediate Similarity NPD5778 Approved
0.748 Intermediate Similarity NPD8390 Approved
0.748 Intermediate Similarity NPD8392 Approved
0.748 Intermediate Similarity NPD8391 Approved
0.7411 Intermediate Similarity NPD6686 Approved
0.7377 Intermediate Similarity NPD8074 Phase 3
0.7368 Intermediate Similarity NPD8413 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD5764 Clinical (unspecified phase)
0.7212 Intermediate Similarity NPD6101 Approved
0.7143 Intermediate Similarity NPD7838 Discovery
0.7131 Intermediate Similarity NPD7642 Approved
0.7075 Intermediate Similarity NPD6411 Approved
0.7 Intermediate Similarity NPD7641 Discontinued
0.685 Remote Similarity NPD7319 Approved
0.6777 Remote Similarity NPD8137 Clinical (unspecified phase)
0.6777 Remote Similarity NPD8295 Clinical (unspecified phase)
0.6746 Remote Similarity NPD7507 Approved
0.672 Remote Similarity NPD8328 Phase 3
0.6617 Remote Similarity NPD7966 Clinical (unspecified phase)
0.6606 Remote Similarity NPD7637 Suspended
0.6604 Remote Similarity NPD5786 Approved
0.6581 Remote Similarity NPD7899 Clinical (unspecified phase)
0.656 Remote Similarity NPD8274 Clinical (unspecified phase)
0.6538 Remote Similarity NPD6435 Approved
0.6529 Remote Similarity NPD8133 Approved
0.6525 Remote Similarity NPD5345 Clinical (unspecified phase)
0.6508 Remote Similarity NPD8080 Discontinued
0.6484 Remote Similarity NPD8273 Phase 1
0.6479 Remote Similarity NPD8389 Clinical (unspecified phase)
0.6476 Remote Similarity NPD7154 Phase 3
0.6441 Remote Similarity NPD6412 Phase 2
0.6429 Remote Similarity NPD1698 Clinical (unspecified phase)
0.6429 Remote Similarity NPD7503 Approved
0.6417 Remote Similarity NPD6371 Approved
0.6389 Remote Similarity NPD4250 Approved
0.6389 Remote Similarity NPD4251 Approved
0.6381 Remote Similarity NPD4269 Approved
0.6381 Remote Similarity NPD4270 Approved
0.6371 Remote Similarity NPD7500 Approved
0.6364 Remote Similarity NPD5785 Approved
0.6355 Remote Similarity NPD1733 Clinical (unspecified phase)
0.6346 Remote Similarity NPD5790 Clinical (unspecified phase)
0.6346 Remote Similarity NPD5368 Approved
0.6343 Remote Similarity NPD8415 Approved
0.6333 Remote Similarity NPD8132 Clinical (unspecified phase)
0.6311 Remote Similarity NPD6053 Discontinued
0.6299 Remote Similarity NPD8269 Approved
0.6299 Remote Similarity NPD8268 Approved
0.6299 Remote Similarity NPD8266 Approved
0.6299 Remote Similarity NPD8267 Approved
0.6299 Remote Similarity NPD8033 Approved
0.6296 Remote Similarity NPD8387 Clinical (unspecified phase)
0.6296 Remote Similarity NPD4249 Approved
0.6289 Remote Similarity NPD4247 Clinical (unspecified phase)
0.6286 Remote Similarity NPD5369 Approved
0.6262 Remote Similarity NPD6400 Clinical (unspecified phase)
0.626 Remote Similarity NPD7736 Approved
0.625 Remote Similarity NPD6370 Approved
0.6239 Remote Similarity NPD8139 Approved
0.6239 Remote Similarity NPD8084 Approved
0.6239 Remote Similarity NPD8083 Approved
0.6239 Remote Similarity NPD8138 Approved
0.6239 Remote Similarity NPD8086 Approved
0.6239 Remote Similarity NPD8085 Approved
0.6239 Remote Similarity NPD8082 Approved
0.622 Remote Similarity NPD8294 Approved
0.622 Remote Similarity NPD8377 Approved
0.6207 Remote Similarity NPD6648 Approved
0.6204 Remote Similarity NPD5363 Approved
0.619 Remote Similarity NPD7327 Approved
0.619 Remote Similarity NPD4819 Approved
0.619 Remote Similarity NPD4822 Approved
0.619 Remote Similarity NPD7328 Approved
0.619 Remote Similarity NPD4820 Approved
0.619 Remote Similarity NPD4821 Approved
0.619 Remote Similarity NPD4252 Approved
0.6186 Remote Similarity NPD8276 Approved
0.6186 Remote Similarity NPD8275 Approved
0.6183 Remote Similarity NPD8293 Discontinued
0.6176 Remote Similarity NPD8039 Approved
0.6172 Remote Similarity NPD8296 Approved
0.6172 Remote Similarity NPD8379 Approved
0.6172 Remote Similarity NPD8380 Approved
0.6172 Remote Similarity NPD8335 Approved
0.6172 Remote Similarity NPD8378 Approved
0.6168 Remote Similarity NPD5362 Discontinued
0.6154 Remote Similarity NPD4271 Approved
0.6154 Remote Similarity NPD7492 Approved
0.6154 Remote Similarity NPD4268 Approved
0.6154 Remote Similarity NPD5344 Discontinued
0.6142 Remote Similarity NPD7516 Approved
0.6134 Remote Similarity NPD8081 Approved
0.6121 Remote Similarity NPD4225 Approved
0.6119 Remote Similarity NPD7260 Phase 2
0.6107 Remote Similarity NPD6616 Approved
0.6094 Remote Similarity NPD6054 Approved
0.6083 Remote Similarity NPD5048 Discontinued
0.6083 Remote Similarity NPD8393 Approved
0.6061 Remote Similarity NPD7078 Approved
0.6053 Remote Similarity NPD5282 Discontinued
0.6047 Remote Similarity NPD6921 Approved
0.6033 Remote Similarity NPD8140 Approved
0.6033 Remote Similarity NPD8307 Discontinued
0.6016 Remote Similarity NPD6421 Discontinued
0.6 Remote Similarity NPD5784 Clinical (unspecified phase)
0.6 Remote Similarity NPD6422 Discontinued
0.5984 Remote Similarity NPD7115 Discovery
0.5983 Remote Similarity NPD7638 Approved
0.5969 Remote Similarity NPD6319 Approved
0.5969 Remote Similarity NPD6059 Approved
0.5968 Remote Similarity NPD7116 Clinical (unspecified phase)
0.5957 Remote Similarity NPD8384 Approved
0.5943 Remote Similarity NPD7329 Approved
0.5935 Remote Similarity NPD8306 Approved
0.5935 Remote Similarity NPD8305 Approved
0.5932 Remote Similarity NPD7639 Approved
0.5932 Remote Similarity NPD7640 Approved
0.5923 Remote Similarity NPD6015 Approved
0.5923 Remote Similarity NPD6016 Approved
0.592 Remote Similarity NPD6882 Approved
0.5909 Remote Similarity NPD6082 Clinical (unspecified phase)
0.5896 Remote Similarity NPD8336 Approved
0.5896 Remote Similarity NPD8337 Approved
0.5887 Remote Similarity NPD8087 Discontinued
0.5878 Remote Similarity NPD5988 Approved
0.5877 Remote Similarity NPD4810 Clinical (unspecified phase)
0.5859 Remote Similarity NPD6009 Approved
0.5841 Remote Similarity NPD5370 Suspended
0.5833 Remote Similarity NPD7632 Discontinued
0.5825 Remote Similarity NPD3181 Approved
0.5806 Remote Similarity NPD4061 Clinical (unspecified phase)
0.58 Remote Similarity NPD896 Approved
0.58 Remote Similarity NPD897 Approved
0.58 Remote Similarity NPD898 Approved
0.5794 Remote Similarity NPD8297 Approved
0.5789 Remote Similarity NPD8522 Clinical (unspecified phase)
0.578 Remote Similarity NPD5209 Approved
0.576 Remote Similarity NPD5955 Clinical (unspecified phase)
0.5727 Remote Similarity NPD5332 Approved
0.5727 Remote Similarity NPD5331 Approved
0.5725 Remote Similarity NPD8338 Approved
0.5725 Remote Similarity NPD6845 Suspended
0.5703 Remote Similarity NPD6010 Discontinued
0.5702 Remote Similarity NPD8300 Approved
0.5702 Remote Similarity NPD8301 Approved
0.5702 Remote Similarity NPD1695 Approved
0.569 Remote Similarity NPD6399 Phase 3
0.5688 Remote Similarity NPD4790 Discontinued
0.5676 Remote Similarity NPD7338 Clinical (unspecified phase)
0.567 Remote Similarity NPD4246 Clinical (unspecified phase)
0.5664 Remote Similarity NPD7524 Approved
0.5657 Remote Similarity NPD3197 Phase 1
0.5636 Remote Similarity NPD4752 Clinical (unspecified phase)
0.5625 Remote Similarity NPD4632 Approved
0.5615 Remote Similarity NPD7505 Discontinued
0.561 Remote Similarity NPD8170 Clinical (unspecified phase)
0.5606 Remote Similarity NPD7299 Clinical (unspecified phase)
0.56 Remote Similarity NPD6899 Approved
0.56 Remote Similarity NPD6881 Approved

Structure

External Identifiers

PubChem CID   46939688
ChEMBL   CHEMBL1223735
ZINC  

Physicochemical Properties

Molecular Weight:  660.25
ALogP:  0.4496
MLogP:  3.66
XLogP:  3.435
# Rotatable Bonds:  17
Polar Surface Area:  122.14
# H-Bond Aceptor:  10
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  42

Download Data

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