Natural Product: NPC198344

Natural Product ID:  NPC198344
Common Name:   Veraguamide B
IUPAC Name:   (3S,6S,9S,12S,13R,16S,19S)-13-(5-bromopent-4-ynyl)-7,12,17-trimethyl-3,6,9,16-tetra(propan-2-yl)-4,14-dioxa-1,7,10,17-tetrazabicyclo[17.3.0]docosane-2,5,8,11,15,18-hexone
Synonyms:   Veraguamide B
Molecular Formula:   C36H57BrN4O8
Standard InCHIKey:  UQYHDSHIIDYSSP-PYYGQVSISA-N
Standard InCHI:  InChI=1S/C36H57BrN4O8/c1-20(2)27-33(44)40(11)29(22(5)6)36(47)49-30(23(7)8)34(45)41-19-15-16-25(41)32(43)39(10)28(21(3)4)35(46)48-26(17-13-12-14-18-37)24(9)31(42)38-27/h20-30H,12-13,15-17,19H2,1-11H3,(H,38,42)/t24-,25-,26+,27-,28-,29-,30-/m0/s1
Canonical SMILES:  BrC#CCCC[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](OC(=O)[C@@H](N(C(=O)[C@@H](N=C([C@H]1C)O)C(C)C)C)C(C)C)C(C)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
NPO5066 Oscillatoria margaritifera Species Oscillatoriaceae Bacteria Isla Canales de Afuera on the Pacific coast of Panama (7°41.617'N, 81°38.379'E) PMID[21488639]
NPO16362 Symploca hydnoides Species Microcoleaceae Bacteria PMID[21446699]
NPO5066 Oscillatoria margaritifera Species Oscillatoriaceae Bacteria PMID[21488639]

  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 = 30000 nM 21446699
NPT165 Cell Line HeLa Homo sapiens IC50 = 17000 nM 21446699

  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 NPC198344 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
0.9896 High Similarity NPC124549
0.9485 High Similarity NPC124554
0.9485 High Similarity NPC301148
0.9485 High Similarity NPC5864
0.9175 High Similarity NPC220234
0.902 High Similarity NPC67009
0.8476 Intermediate Similarity NPC171734
0.8365 Intermediate Similarity NPC323720
0.8081 Intermediate Similarity NPC474576
0.8 Intermediate Similarity NPC62263
0.8 Intermediate Similarity NPC173763
0.8 Intermediate Similarity NPC471098
0.798 Intermediate Similarity NPC475801
0.798 Intermediate Similarity NPC474593
0.7714 Intermediate Similarity NPC475440
0.7297 Intermediate Similarity NPC475637
0.7212 Intermediate Similarity NPC476019
0.7182 Intermediate Similarity NPC471097
0.7182 Intermediate Similarity NPC475149
0.7172 Intermediate Similarity NPC246005
0.7156 Intermediate Similarity NPC475791
0.7156 Intermediate Similarity NPC13175
0.7113 Intermediate Similarity NPC473741
0.7113 Intermediate Similarity NPC477145
0.7064 Intermediate Similarity NPC475758
0.7053 Intermediate Similarity NPC263281
0.7048 Intermediate Similarity NPC477538
0.7037 Intermediate Similarity NPC134504
0.7037 Intermediate Similarity NPC47076
0.703 Intermediate Similarity NPC472351
0.7019 Intermediate Similarity NPC322966
0.6981 Remote Similarity NPC315237
0.69 Remote Similarity NPC23984
0.6885 Remote Similarity NPC477238
0.6881 Remote Similarity NPC473597
0.6875 Remote Similarity NPC178919
0.6864 Remote Similarity NPC471202
0.6864 Remote Similarity NPC63191
0.6838 Remote Similarity NPC476875
0.6832 Remote Similarity NPC53858
0.6832 Remote Similarity NPC84128
0.6804 Remote Similarity NPC86064
0.6733 Remote Similarity NPC476302
0.6721 Remote Similarity NPC477237
0.6701 Remote Similarity NPC43219
0.67 Remote Similarity NPC31756
0.6667 Remote Similarity NPC329761
0.6667 Remote Similarity NPC225648
0.6635 Remote Similarity NPC227051
0.6634 Remote Similarity NPC476117
0.6634 Remote Similarity NPC476137
0.6634 Remote Similarity NPC476243
0.6634 Remote Similarity NPC476156
0.6632 Remote Similarity NPC212866
0.6632 Remote Similarity NPC29598
0.6609 Remote Similarity NPC128303
0.6602 Remote Similarity NPC235078
0.6562 Remote Similarity NPC478256
0.6552 Remote Similarity NPC241394
0.6538 Remote Similarity NPC145748
0.6538 Remote Similarity NPC155670
0.6538 Remote Similarity NPC95478
0.6529 Remote Similarity NPC103391
0.6529 Remote Similarity NPC472536
0.6526 Remote Similarity NPC10716
0.6522 Remote Similarity NPC476877
0.6454 Remote Similarity NPC129666
0.6415 Remote Similarity NPC477539
0.641 Remote Similarity NPC476876
0.6408 Remote Similarity NPC470783
0.64 Remote Similarity NPC470652
0.6389 Remote Similarity NPC275715
0.6373 Remote Similarity NPC315535
0.6373 Remote Similarity NPC478017
0.6373 Remote Similarity NPC315131
0.6349 Remote Similarity NPC315188
0.633 Remote Similarity NPC477729
0.6328 Remote Similarity NPC470650
0.6328 Remote Similarity NPC470653
0.6328 Remote Similarity NPC470654
0.6304 Remote Similarity NPC263493
0.6304 Remote Similarity NPC269398
0.6286 Remote Similarity NPC5620
0.6279 Remote Similarity NPC309525
0.6275 Remote Similarity NPC316242
0.6259 Remote Similarity NPC139326
0.6214 Remote Similarity NPC312315
0.6212 Remote Similarity NPC313657
0.621 Remote Similarity NPC296043
0.62 Remote Similarity NPC266888
0.62 Remote Similarity NPC256312
0.62 Remote Similarity NPC161774
0.6197 Remote Similarity NPC138775
0.6167 Remote Similarity NPC207820
0.616 Remote Similarity NPC329216
0.6139 Remote Similarity NPC327272
0.6095 Remote Similarity NPC475542
0.6094 Remote Similarity NPC160688
0.6087 Remote Similarity NPC471264
0.6087 Remote Similarity NPC471265
0.6084 Remote Similarity NPC145113
0.6068 Remote Similarity NPC188785
0.6063 Remote Similarity NPC469899
0.6061 Remote Similarity NPC470651
0.6061 Remote Similarity NPC470655
0.6055 Remote Similarity NPC477728
0.605 Remote Similarity NPC205176
0.6045 Remote Similarity NPC120335
0.604 Remote Similarity NPC209156
0.604 Remote Similarity NPC138435
0.6028 Remote Similarity NPC161069
0.6 Remote Similarity NPC76297
0.6 Remote Similarity NPC196007
0.6 Remote Similarity NPC214532
0.5971 Remote Similarity NPC68865
0.596 Remote Similarity NPC28348
0.596 Remote Similarity NPC474298
0.596 Remote Similarity NPC473985
0.596 Remote Similarity NPC475808
0.596 Remote Similarity NPC474299
0.5944 Remote Similarity NPC209509
0.5941 Remote Similarity NPC141325
0.5933 Remote Similarity NPC297145
0.5933 Remote Similarity NPC197743
0.5931 Remote Similarity NPC240848
0.5929 Remote Similarity NPC476133
0.5929 Remote Similarity NPC98424
0.5929 Remote Similarity NPC92784
0.5929 Remote Similarity NPC178662
0.5929 Remote Similarity NPC470884
0.5923 Remote Similarity NPC273185
0.5922 Remote Similarity NPC476130
0.5922 Remote Similarity NPC476324
0.5918 Remote Similarity NPC162104
0.5878 Remote Similarity NPC50520
0.5877 Remote Similarity NPC38172
0.5874 Remote Similarity NPC476978
0.5865 Remote Similarity NPC59867
0.5833 Remote Similarity NPC477730
0.5822 Remote Similarity NPC471821
0.5822 Remote Similarity NPC471820
0.581 Remote Similarity NPC233108
0.58 Remote Similarity NPC314273
0.58 Remote Similarity NPC193280
0.5782 Remote Similarity NPC2501
0.5776 Remote Similarity NPC117829
0.5775 Remote Similarity NPC239762
0.5775 Remote Similarity NPC163392
0.5755 Remote Similarity NPC473984
0.5743 Remote Similarity NPC476285
0.5741 Remote Similarity NPC284456
0.5741 Remote Similarity NPC6902
0.5728 Remote Similarity NPC126186
0.5714 Remote Similarity NPC477518
0.5714 Remote Similarity NPC473495
0.5714 Remote Similarity NPC52533
0.5667 Remote Similarity NPC122590
0.5664 Remote Similarity NPC268841
0.5664 Remote Similarity NPC46098
0.5664 Remote Similarity NPC307357
0.5664 Remote Similarity NPC155230
0.5652 Remote Similarity NPC270005
0.5652 Remote Similarity NPC208537
0.5645 Remote Similarity NPC296143
0.5644 Remote Similarity NPC322274
0.5641 Remote Similarity NPC469739
0.5634 Remote Similarity NPC127741
0.5631 Remote Similarity NPC477643
0.5631 Remote Similarity NPC320865
0.5631 Remote Similarity NPC474403
0.5631 Remote Similarity NPC477641
0.5619 Remote Similarity NPC470782
0.5616 Remote Similarity NPC316008
0.5616 Remote Similarity NPC313867
0.561 Remote Similarity NPC471844
0.5603 Remote Similarity NPC301010

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC198344 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
0.7048 Intermediate Similarity NPD4780 Clinical (unspecified phase)
0.6893 Remote Similarity NPD7759 Phase 2
0.6893 Remote Similarity NPD7760 Phase 2
0.6893 Remote Similarity NPD3723 Clinical (unspecified phase)
0.6733 Remote Similarity NPD7763 Phase 2
0.6733 Remote Similarity NPD7762 Phase 2
0.6729 Remote Similarity NPD4261 Phase 1
0.6667 Remote Similarity NPD3715 Approved
0.6667 Remote Similarity NPD3714 Approved
0.6667 Remote Similarity NPD3713 Approved
0.6636 Remote Similarity NPD7841 Clinical (unspecified phase)
0.6632 Remote Similarity NPD7840 Approved
0.6518 Remote Similarity NPD8038 Phase 2
0.6505 Remote Similarity NPD2683 Discontinued
0.6373 Remote Similarity NPD7917 Clinical (unspecified phase)
0.6373 Remote Similarity NPD7918 Clinical (unspecified phase)
0.6296 Remote Similarity NPD3177 Phase 3
0.6239 Remote Similarity NPD6122 Discontinued
0.6126 Remote Similarity NPD2682 Approved
0.6048 Remote Similarity NPD8298 Phase 2
0.6038 Remote Similarity NPD1125 Discovery
0.5929 Remote Similarity NPD6699 Clinical (unspecified phase)
0.59 Remote Similarity NPD2694 Approved
0.59 Remote Similarity NPD2696 Approved
0.59 Remote Similarity NPD2695 Approved
0.59 Remote Similarity NPD2697 Approved
0.5897 Remote Similarity NPD4825 Clinical (unspecified phase)
0.5873 Remote Similarity NPD7916 Approved
0.5873 Remote Similarity NPD7915 Approved
0.5862 Remote Similarity NPD1784 Approved
0.58 Remote Similarity NPD3724 Clinical (unspecified phase)
0.58 Remote Similarity NPD620 Approved
0.5743 Remote Similarity NPD2220 Clinical (unspecified phase)
0.5714 Remote Similarity NPD2689 Clinical (unspecified phase)
0.5714 Remote Similarity NPD5359 Clinical (unspecified phase)
0.5691 Remote Similarity NPD6937 Approved
0.5682 Remote Similarity NPD7652 Discontinued
0.5676 Remote Similarity NPD5791 Phase 2
0.566 Remote Similarity NPD8143 Approved
0.566 Remote Similarity NPD8144 Approved
0.5631 Remote Similarity NPD2256 Clinical (unspecified phase)
0.5625 Remote Similarity NPD3176 Clinical (unspecified phase)
0.5619 Remote Similarity NPD1453 Phase 1
0.5607 Remote Similarity NPD4815 Discontinued

Structure

External Identifiers

PubChem CID   53355337
ChEMBL   CHEMBL1783106
ZINC  

Physicochemical Properties

Molecular Weight:  752.34
ALogP:  -0.4013
MLogP:  3.99
XLogP:  4.623
# Rotatable Bonds:  19
Polar Surface Area:  146.12
# H-Bond Aceptor:  12
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  49

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