Natural Product: NPC124549

Natural Product ID:  NPC124549
Common Name:   Veraguamide A
IUPAC Name:   (3S,6S,9S,12S,13R,16S,19S)-13-(5-bromopent-4-ynyl)-3-[(2S)-butan-2-yl]-7,12,17-trimethyl-6,9,16-tri(propan-2-yl)-4,14-dioxa-1,7,10,17-tetrazabicyclo[17.3.0]docosane-2,5,8,11,15,18-hexone
Synonyms:   Veraguamide A
Molecular Formula:   C37H59BrN4O8
Standard InCHIKey:  WWYBIFCBAWCPFI-AVCHBABLSA-N
Standard InCHI:  InChI=1S/C37H59BrN4O8/c1-12-24(8)31-35(46)42-20-16-17-26(42)33(44)40(10)29(22(4)5)36(47)49-27(18-14-13-15-19-38)25(9)32(43)39-28(21(2)3)34(45)41(11)30(23(6)7)37(48)50-31/h21-31H,12-14,16-18,20H2,1-11H3,(H,39,43)/t24-,25-,26-,27+,28-,29-,30-,31-/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@H](CC)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
NPO16362 Symploca hydnoides Species Microcoleaceae Bacteria PMID[21446699]
NPO5066 Oscillatoria margaritifera Species Oscillatoriaceae Bacteria PMID[21488639]
NPO12359 Rhodotorula toruloides Species Sporidiobolaceae Eukaryota UNPD*
NPO20342 Lichtheimia corymbifera Species Lichtheimiaceae Eukaryota UNPD*
NPO18009 Cicer flexuosum Species Fabaceae Eukaryota UNPD*
NPO16336 Magnolia tomentosa Species Magnoliaceae Eukaryota UNPD*
NPO25587 Pearsonia sessilifolia Species Fabaceae Eukaryota UNPD*
NPO29477 Hymenopellis radicata Species Physalacriaceae Eukaryota UNPD*
NPO28005 Panax japonicus Species Araliaceae Eukaryota UNPD*
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]
NPO1614 Silene baccifera Species Caryophyllaceae Eukaryota UNPD*
NPO15028 Lespedeza cuneata Species Fabaceae Eukaryota UNPD*
NPO16059 Lobelia polyphylla Species Campanulaceae Eukaryota UNPD*
NPO16825 Scabiosa columbaria Species Caprifoliaceae Eukaryota UNPD*
NPO27391 Ammopiptanthus mongolicus Species Fabaceae Eukaryota UNPD*
NPO2278 Serenoa serrulata Species Arecaceae Eukaryota UNPD*

  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 = 26000 nM 21446699
NPT165 Cell Line HeLa Homo sapiens IC50 = 21000 nM 21446699
NPT397 Cell Line NCI-H460 Homo sapiens LD50 = 141 nM 21488639

  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 NPC124549 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 NPC198344
0.9588 High Similarity NPC5864
0.9588 High Similarity NPC124554
0.9588 High Similarity NPC301148
0.9278 High Similarity NPC220234
0.9118 High Similarity NPC67009
0.8571 High Similarity NPC171734
0.8462 Intermediate Similarity NPC323720
0.81 Intermediate Similarity NPC62263
0.81 Intermediate Similarity NPC173763
0.81 Intermediate Similarity NPC471098
0.8 Intermediate Similarity NPC474576
0.79 Intermediate Similarity NPC474593
0.79 Intermediate Similarity NPC475801
0.7642 Intermediate Similarity NPC475440
0.7387 Intermediate Similarity NPC475637
0.7308 Intermediate Similarity NPC476019
0.7273 Intermediate Similarity NPC471097
0.7273 Intermediate Similarity NPC475149
0.7216 Intermediate Similarity NPC473741
0.7216 Intermediate Similarity NPC477145
0.713 Intermediate Similarity NPC134504
0.713 Intermediate Similarity NPC47076
0.7129 Intermediate Similarity NPC472351
0.7115 Intermediate Similarity NPC322966
0.71 Intermediate Similarity NPC246005
0.7091 Intermediate Similarity NPC475791
0.7091 Intermediate Similarity NPC13175
0.7075 Intermediate Similarity NPC315237
0.7 Intermediate Similarity NPC475758
0.6981 Remote Similarity NPC477538
0.6979 Remote Similarity NPC178919
0.6979 Remote Similarity NPC263281
0.6972 Remote Similarity NPC473597
0.6967 Remote Similarity NPC477238
0.6949 Remote Similarity NPC471202
0.6949 Remote Similarity NPC63191
0.6931 Remote Similarity NPC53858
0.6931 Remote Similarity NPC84128
0.6907 Remote Similarity NPC86064
0.6832 Remote Similarity NPC476302
0.6832 Remote Similarity NPC23984
0.6804 Remote Similarity NPC43219
0.6803 Remote Similarity NPC477237
0.678 Remote Similarity NPC476875
0.6739 Remote Similarity NPC329761
0.6739 Remote Similarity NPC225648
0.6733 Remote Similarity NPC476117
0.6733 Remote Similarity NPC476243
0.6733 Remote Similarity NPC476137
0.6733 Remote Similarity NPC476156
0.6667 Remote Similarity NPC478256
0.6638 Remote Similarity NPC241394
0.6634 Remote Similarity NPC31756
0.6612 Remote Similarity NPC472536
0.6612 Remote Similarity NPC103391
0.6571 Remote Similarity NPC227051
0.6562 Remote Similarity NPC29598
0.6562 Remote Similarity NPC212866
0.6552 Remote Similarity NPC128303
0.6538 Remote Similarity NPC235078
0.6525 Remote Similarity NPC129666
0.648 Remote Similarity NPC470652
0.6476 Remote Similarity NPC155670
0.6476 Remote Similarity NPC95478
0.6476 Remote Similarity NPC145748
0.6466 Remote Similarity NPC476877
0.6458 Remote Similarity NPC10716
0.6429 Remote Similarity NPC315188
0.6422 Remote Similarity NPC477729
0.6406 Remote Similarity NPC470654
0.6406 Remote Similarity NPC470650
0.6406 Remote Similarity NPC470653
0.6377 Remote Similarity NPC263493
0.6377 Remote Similarity NPC269398
0.6357 Remote Similarity NPC309525
0.6357 Remote Similarity NPC5620
0.6356 Remote Similarity NPC476876
0.6355 Remote Similarity NPC477539
0.6346 Remote Similarity NPC470783
0.6331 Remote Similarity NPC139326
0.633 Remote Similarity NPC275715
0.6311 Remote Similarity NPC315535
0.6311 Remote Similarity NPC478017
0.6311 Remote Similarity NPC315131
0.629 Remote Similarity NPC296043
0.6288 Remote Similarity NPC313657
0.6268 Remote Similarity NPC138775
0.625 Remote Similarity NPC207820
0.624 Remote Similarity NPC329216
0.6214 Remote Similarity NPC316242
0.6172 Remote Similarity NPC160688
0.6159 Remote Similarity NPC471264
0.6159 Remote Similarity NPC471265
0.6154 Remote Similarity NPC312315
0.6154 Remote Similarity NPC145113
0.6147 Remote Similarity NPC477728
0.6142 Remote Similarity NPC469899
0.6139 Remote Similarity NPC266888
0.6139 Remote Similarity NPC138435
0.6139 Remote Similarity NPC209156
0.6139 Remote Similarity NPC256312
0.6139 Remote Similarity NPC161774
0.6136 Remote Similarity NPC470651
0.6136 Remote Similarity NPC470655
0.6134 Remote Similarity NPC205176
0.6119 Remote Similarity NPC120335
0.6099 Remote Similarity NPC161069
0.6078 Remote Similarity NPC327272
0.6043 Remote Similarity NPC68865
0.604 Remote Similarity NPC141325
0.6038 Remote Similarity NPC475542
0.6019 Remote Similarity NPC476130
0.6019 Remote Similarity NPC476324
0.6017 Remote Similarity NPC188785
0.6014 Remote Similarity NPC209509
0.6 Remote Similarity NPC470884
0.6 Remote Similarity NPC178662
0.6 Remote Similarity NPC476133
0.6 Remote Similarity NPC98424
0.6 Remote Similarity NPC92784
0.6 Remote Similarity NPC240848
0.6 Remote Similarity NPC297145
0.6 Remote Similarity NPC197743
0.5986 Remote Similarity NPC162104
0.5954 Remote Similarity NPC50520
0.5944 Remote Similarity NPC476978
0.5941 Remote Similarity NPC196007
0.5941 Remote Similarity NPC214532
0.5941 Remote Similarity NPC76297
0.5926 Remote Similarity NPC477730
0.5905 Remote Similarity NPC233108
0.59 Remote Similarity NPC473985
0.59 Remote Similarity NPC474298
0.59 Remote Similarity NPC475808
0.59 Remote Similarity NPC28348
0.59 Remote Similarity NPC474299
0.589 Remote Similarity NPC471821
0.589 Remote Similarity NPC471820
0.5878 Remote Similarity NPC273185
0.585 Remote Similarity NPC2501
0.5845 Remote Similarity NPC239762
0.5845 Remote Similarity NPC163392
0.5826 Remote Similarity NPC38172
0.581 Remote Similarity NPC59867
0.5804 Remote Similarity NPC473495
0.5804 Remote Similarity NPC52533
0.5789 Remote Similarity NPC477518
0.5743 Remote Similarity NPC193280
0.5743 Remote Similarity NPC314273
0.5734 Remote Similarity NPC46098
0.5734 Remote Similarity NPC307357
0.5734 Remote Similarity NPC268841
0.5733 Remote Similarity NPC122590
0.5726 Remote Similarity NPC296143
0.5726 Remote Similarity NPC117829
0.5704 Remote Similarity NPC127741
0.5701 Remote Similarity NPC473984
0.5691 Remote Similarity NPC471844
0.5688 Remote Similarity NPC284456
0.5688 Remote Similarity NPC6902
0.5686 Remote Similarity NPC476285
0.5686 Remote Similarity NPC476291
0.5685 Remote Similarity NPC316008
0.5685 Remote Similarity NPC313867
0.5676 Remote Similarity NPC277918
0.5673 Remote Similarity NPC126186
0.5646 Remote Similarity NPC314358
0.5641 Remote Similarity NPC280066
0.5636 Remote Similarity NPC47135
0.5625 Remote Similarity NPC469597
0.5616 Remote Similarity NPC52748
0.5616 Remote Similarity NPC314388
0.5616 Remote Similarity NPC315283
0.5614 Remote Similarity NPC155230
0.5603 Remote Similarity NPC270005
0.5603 Remote Similarity NPC208537
0.56 Remote Similarity NPC15413

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC124549 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
0.699 Remote Similarity NPD3723 Clinical (unspecified phase)
0.6981 Remote Similarity NPD4780 Clinical (unspecified phase)
0.6827 Remote Similarity NPD7760 Phase 2
0.6827 Remote Similarity NPD7759 Phase 2
0.6757 Remote Similarity NPD3714 Approved
0.6757 Remote Similarity NPD3715 Approved
0.6757 Remote Similarity NPD3713 Approved
0.6667 Remote Similarity NPD7763 Phase 2
0.6667 Remote Similarity NPD4261 Phase 1
0.6667 Remote Similarity NPD7762 Phase 2
0.6607 Remote Similarity NPD8038 Phase 2
0.6577 Remote Similarity NPD7841 Clinical (unspecified phase)
0.6562 Remote Similarity NPD7840 Approved
0.6442 Remote Similarity NPD2683 Discontinued
0.6325 Remote Similarity NPD6122 Discontinued
0.6311 Remote Similarity NPD7917 Clinical (unspecified phase)
0.6311 Remote Similarity NPD7918 Clinical (unspecified phase)
0.6239 Remote Similarity NPD3177 Phase 3
0.6216 Remote Similarity NPD2682 Approved
0.6129 Remote Similarity NPD8298 Phase 2
0.6018 Remote Similarity NPD6699 Clinical (unspecified phase)
0.6 Remote Similarity NPD2696 Approved
0.6 Remote Similarity NPD2697 Approved
0.6 Remote Similarity NPD2695 Approved
0.6 Remote Similarity NPD2694 Approved
0.5983 Remote Similarity NPD4825 Clinical (unspecified phase)
0.5981 Remote Similarity NPD1125 Discovery
0.5952 Remote Similarity NPD7915 Approved
0.5952 Remote Similarity NPD7916 Approved
0.5948 Remote Similarity NPD1784 Approved
0.59 Remote Similarity NPD3724 Clinical (unspecified phase)
0.59 Remote Similarity NPD620 Approved
0.5798 Remote Similarity NPD5359 Clinical (unspecified phase)
0.5772 Remote Similarity NPD6937 Approved
0.5758 Remote Similarity NPD7652 Discontinued
0.5755 Remote Similarity NPD8143 Approved
0.5755 Remote Similarity NPD8144 Approved
0.5714 Remote Similarity NPD3176 Clinical (unspecified phase)
0.5688 Remote Similarity NPD1448 Clinical (unspecified phase)
0.5686 Remote Similarity NPD2220 Clinical (unspecified phase)
0.566 Remote Similarity NPD2689 Clinical (unspecified phase)
0.5657 Remote Similarity NPD4272 Discontinued
0.5636 Remote Similarity NPD7345 Approved
0.5635 Remote Similarity NPD4260 Discontinued
0.5625 Remote Similarity NPD5791 Phase 2

Structure

External Identifiers

PubChem CID   53355336
ChEMBL   CHEMBL1783105
ZINC  

Physicochemical Properties

Molecular Weight:  766.35
ALogP:  -1.0775
MLogP:  4.1
XLogP:  5.192
# Rotatable Bonds:  20
Polar Surface Area:  146.12
# H-Bond Aceptor:  12
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  50

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