Natural Product: NPC469716

Natural Product ID:  NPC469716
Common Name:   Nagelamide H
IUPAC Name:   2-[[2-amino-5-[2-amino-4-[(E)-3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)amino]prop-1-enyl]-1H-imidazol-5-yl]-5-[(E)-3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)amino]prop-1-enyl]imidazol-4-yl]amino]ethanesulfonic acid
Synonyms:   Nagelamide H
Molecular Formula:   C24H25Br4N11O5S
Standard InCHIKey:  YKINYXUSZLKEHU-ZPUQHVIOSA-N
Standard InCHI:  InChI=1S/C24H25Br4N11O5S/c25-11-9-14(34-17(11)27)19(40)31-5-1-3-13-16(37-22(29)36-13)24(21(38-23(30)39-24)33-7-8-45(42,43)44)4-2-6-32-20(41)15-10-12(26)18(28)35-15/h1-4,9-10,34-35H,5-8H2,(H,31,40)(H,32,41)(H3,29,36,37)(H,42,43,44)(H3,30,33,38,39)/b3-1+,4-2+
Canonical SMILES:  N=c1[nH]c(c([nH]1)C1(/C=C/CNC(=O)c2cc(c([nH]2)Br)Br)NC(=N)NC1=NCCS(=O)(=O)O)/C=C/CNC(=O)c1cc(c([nH]1)Br)Br
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
NPO32675 agelas sp. Species Agelasidae Eukaryota PMID[15332839]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT19 Organism Escherichia coli Escherichia coli MIC > 33.3 ug/ml 12880316
NPT2 Others Unspecified IC50 = 46000 nM 12880316
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 16.7 ug/ml 18183025
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 33.3 ug/ml 25139568

  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 NPC469716 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
0.8798 High Similarity NPC63571
0.875 High Similarity NPC310633
0.8696 High Similarity NPC111566
0.8421 Intermediate Similarity NPC19342
0.8325 Intermediate Similarity NPC476414
0.8308 Intermediate Similarity NPC9635
0.8272 Intermediate Similarity NPC476413
0.8222 Intermediate Similarity NPC206148
0.8112 Intermediate Similarity NPC19696
0.8112 Intermediate Similarity NPC136957
0.801 Intermediate Similarity NPC475286
0.801 Intermediate Similarity NPC174281
0.7959 Intermediate Similarity NPC48117
0.7959 Intermediate Similarity NPC476526
0.7959 Intermediate Similarity NPC329765
0.7923 Intermediate Similarity NPC306160
0.7807 Intermediate Similarity NPC227489
0.7807 Intermediate Similarity NPC476421
0.7807 Intermediate Similarity NPC28096
0.7778 Intermediate Similarity NPC136441
0.773 Intermediate Similarity NPC476418
0.7713 Intermediate Similarity NPC54214
0.7713 Intermediate Similarity NPC226835
0.763 Intermediate Similarity NPC469717
0.7579 Intermediate Similarity NPC80528
0.7551 Intermediate Similarity NPC476527
0.754 Intermediate Similarity NPC73687
0.7539 Intermediate Similarity NPC97106
0.7538 Intermediate Similarity NPC469814
0.7536 Intermediate Similarity NPC476524
0.7452 Intermediate Similarity NPC476525
0.7436 Intermediate Similarity NPC472861
0.7436 Intermediate Similarity NPC184932
0.7344 Intermediate Similarity NPC469976
0.7268 Intermediate Similarity NPC37268
0.7213 Intermediate Similarity NPC260041
0.7143 Intermediate Similarity NPC210123
0.7128 Intermediate Similarity NPC271927
0.7121 Intermediate Similarity NPC314281
0.7121 Intermediate Similarity NPC40530
0.7114 Intermediate Similarity NPC112489
0.7114 Intermediate Similarity NPC46022
0.705 Intermediate Similarity NPC270834
0.7039 Intermediate Similarity NPC150592
0.6983 Remote Similarity NPC20021
0.6963 Remote Similarity NPC27296
0.6957 Remote Similarity NPC46811
0.6923 Remote Similarity NPC474696
0.6894 Remote Similarity NPC66642
0.6859 Remote Similarity NPC474236
0.6786 Remote Similarity NPC2414
0.6786 Remote Similarity NPC474383
0.6652 Remote Similarity NPC470703
0.6606 Remote Similarity NPC473218
0.6606 Remote Similarity NPC470702
0.6588 Remote Similarity NPC474180
0.6588 Remote Similarity NPC188821
0.657 Remote Similarity NPC476423
0.6548 Remote Similarity NPC473706
0.6542 Remote Similarity NPC474389
0.6524 Remote Similarity NPC474357
0.6509 Remote Similarity NPC470323
0.6481 Remote Similarity NPC935
0.6481 Remote Similarity NPC267078
0.6457 Remote Similarity NPC469715
0.6377 Remote Similarity NPC16659
0.6359 Remote Similarity NPC477004
0.6329 Remote Similarity NPC265710
0.6327 Remote Similarity NPC472260
0.628 Remote Similarity NPC473380
0.628 Remote Similarity NPC240088
0.627 Remote Similarity NPC125181
0.627 Remote Similarity NPC263117
0.627 Remote Similarity NPC242872
0.6269 Remote Similarity NPC253687
0.6213 Remote Similarity NPC156003
0.6207 Remote Similarity NPC233380
0.6201 Remote Similarity NPC267811
0.6193 Remote Similarity NPC52110
0.6184 Remote Similarity NPC50562
0.6182 Remote Similarity NPC269203
0.6182 Remote Similarity NPC166209
0.6182 Remote Similarity NPC77241
0.6182 Remote Similarity NPC13456
0.6179 Remote Similarity NPC133003
0.6174 Remote Similarity NPC475736
0.6157 Remote Similarity NPC67658
0.6136 Remote Similarity NPC475914
0.6136 Remote Similarity NPC268744
0.6136 Remote Similarity NPC153123
0.6136 Remote Similarity NPC474318
0.6136 Remote Similarity NPC201266
0.6136 Remote Similarity NPC220797
0.6132 Remote Similarity NPC21429
0.6121 Remote Similarity NPC474195
0.6118 Remote Similarity NPC69843
0.6105 Remote Similarity NPC291517
0.6105 Remote Similarity NPC23215
0.61 Remote Similarity NPC321939
0.6096 Remote Similarity NPC477413
0.6085 Remote Similarity NPC474196
0.6085 Remote Similarity NPC470205
0.6073 Remote Similarity NPC292434
0.6073 Remote Similarity NPC14448
0.6073 Remote Similarity NPC195704
0.6073 Remote Similarity NPC98156
0.6073 Remote Similarity NPC64661
0.6073 Remote Similarity NPC138596
0.6073 Remote Similarity NPC167200
0.6073 Remote Similarity NPC200397
0.607 Remote Similarity NPC142688
0.6065 Remote Similarity NPC324091
0.6062 Remote Similarity NPC116555
0.6056 Remote Similarity NPC477003
0.6037 Remote Similarity NPC476460
0.6031 Remote Similarity NPC209281
0.6031 Remote Similarity NPC129753
0.6031 Remote Similarity NPC97230
0.6031 Remote Similarity NPC205604
0.6031 Remote Similarity NPC286529
0.6031 Remote Similarity NPC302717
0.6031 Remote Similarity NPC244087
0.6031 Remote Similarity NPC74928
0.6031 Remote Similarity NPC169308
0.6031 Remote Similarity NPC12831
0.6031 Remote Similarity NPC3698
0.6031 Remote Similarity NPC77582
0.6031 Remote Similarity NPC59839
0.6031 Remote Similarity NPC48171
0.6029 Remote Similarity NPC186068
0.6027 Remote Similarity NPC317701
0.6018 Remote Similarity NPC171317
0.6 Remote Similarity NPC247987
0.6 Remote Similarity NPC473376
0.6 Remote Similarity NPC58268
0.6 Remote Similarity NPC129412
0.6 Remote Similarity NPC135601
0.6 Remote Similarity NPC141612
0.6 Remote Similarity NPC101130
0.6 Remote Similarity NPC201831
0.6 Remote Similarity NPC17273
0.6 Remote Similarity NPC17487
0.6 Remote Similarity NPC114033
0.5982 Remote Similarity NPC304203
0.5981 Remote Similarity NPC161861
0.5976 Remote Similarity NPC477107
0.5976 Remote Similarity NPC477109
0.5976 Remote Similarity NPC477108
0.5975 Remote Similarity NPC476817
0.5963 Remote Similarity NPC243716
0.5948 Remote Similarity NPC470731
0.5948 Remote Similarity NPC470732
0.5945 Remote Similarity NPC473666
0.5932 Remote Similarity NPC175150
0.5932 Remote Similarity NPC243633
0.5931 Remote Similarity NPC282247
0.5921 Remote Similarity NPC71238
0.5915 Remote Similarity NPC88110
0.5899 Remote Similarity NPC473946
0.5887 Remote Similarity NPC471193
0.5887 Remote Similarity NPC471194
0.5885 Remote Similarity NPC471943
0.588 Remote Similarity NPC99939
0.588 Remote Similarity NPC308931
0.588 Remote Similarity NPC474258
0.5876 Remote Similarity NPC472288
0.5872 Remote Similarity NPC168209
0.5862 Remote Similarity NPC75135
0.586 Remote Similarity NPC117027
0.5856 Remote Similarity NPC79356
0.5856 Remote Similarity NPC102592
0.5848 Remote Similarity NPC237414
0.5847 Remote Similarity NPC272174
0.5844 Remote Similarity NPC72956
0.5844 Remote Similarity NPC320968
0.5844 Remote Similarity NPC54981
0.5842 Remote Similarity NPC109158
0.5841 Remote Similarity NPC91179
0.5837 Remote Similarity NPC225622
0.5837 Remote Similarity NPC221726
0.5837 Remote Similarity NPC477414
0.5833 Remote Similarity NPC471191
0.5819 Remote Similarity NPC6865
0.5819 Remote Similarity NPC31385
0.5819 Remote Similarity NPC153980
0.5819 Remote Similarity NPC75726
0.5819 Remote Similarity NPC110602
0.5816 Remote Similarity NPC19170
0.5814 Remote Similarity NPC307191
0.5813 Remote Similarity NPC232798
0.5798 Remote Similarity NPC327095
0.5798 Remote Similarity NPC312942
0.5798 Remote Similarity NPC31097
0.5795 Remote Similarity NPC77101
0.5794 Remote Similarity NPC54744
0.5789 Remote Similarity NPC88115
0.5785 Remote Similarity NPC77061
0.5784 Remote Similarity NPC33229
0.5775 Remote Similarity NPC151635
0.5774 Remote Similarity NPC40455

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469716 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
0.7268 Intermediate Similarity NPD7459 Phase 2
0.6667 Remote Similarity NPD5274 Clinical (unspecified phase)
0.6524 Remote Similarity NPD5686 Approved
0.6524 Remote Similarity NPD5685 Approved
0.6512 Remote Similarity NPD2405 Phase 3
0.6504 Remote Similarity NPD5198 Approved
0.6504 Remote Similarity NPD5199 Approved
0.6396 Remote Similarity NPD7704 Clinical (unspecified phase)
0.6372 Remote Similarity NPD2289 Phase 3
0.6372 Remote Similarity NPD2290 Phase 3
0.6278 Remote Similarity NPD2443 Approved
0.6278 Remote Similarity NPD2442 Approved
0.6201 Remote Similarity NPD5643 Phase 2
0.6184 Remote Similarity NPD7971 Clinical (unspecified phase)
0.6184 Remote Similarity NPD7970 Approved
0.6164 Remote Similarity NPD465 Clinical (unspecified phase)
0.6154 Remote Similarity NPD3890 Phase 2
0.6154 Remote Similarity NPD3891 Phase 2
0.6106 Remote Similarity NPD2408 Discontinued
0.6089 Remote Similarity NPD1506 Discontinued
0.6068 Remote Similarity NPD5001 Clinical (unspecified phase)
0.6061 Remote Similarity NPD8258 Clinical (unspecified phase)
0.6061 Remote Similarity NPD8256 Approved
0.6061 Remote Similarity NPD8257 Approved
0.6055 Remote Similarity NPD460 Discontinued
0.6052 Remote Similarity NPD6579 Phase 2
0.6035 Remote Similarity NPD1600 Suspended
0.6018 Remote Similarity NPD8493 Clinical (unspecified phase)
0.6018 Remote Similarity NPD6328 Clinical (unspecified phase)
0.6018 Remote Similarity NPD1982 Phase 1
0.5982 Remote Similarity NPD4134 Clinical (unspecified phase)
0.5973 Remote Similarity NPD2008 Discontinued
0.5963 Remote Similarity NPD5592 Clinical (unspecified phase)
0.5958 Remote Similarity NPD5935 Discontinued
0.5957 Remote Similarity NPD7656 Approved
0.5957 Remote Similarity NPD7657 Approved
0.5955 Remote Similarity NPD953 Approved
0.5938 Remote Similarity NPD7817 Phase 1
0.5938 Remote Similarity NPD6837 Clinical (unspecified phase)
0.5901 Remote Similarity NPD2880 Discontinued
0.5899 Remote Similarity NPD2009 Clinical (unspecified phase)
0.589 Remote Similarity NPD2892 Phase 1
0.5877 Remote Similarity NPD3410 Approved
0.5877 Remote Similarity NPD3411 Phase 2
0.5871 Remote Similarity NPD971 Clinical (unspecified phase)
0.5868 Remote Similarity NPD6263 Clinical (unspecified phase)
0.586 Remote Similarity NPD1745 Approved
0.5856 Remote Similarity NPD7027 Phase 3
0.5852 Remote Similarity NPD2026 Approved
0.5849 Remote Similarity NPD2367 Phase 2
0.5842 Remote Similarity NPD9343 Clinical (unspecified phase)
0.584 Remote Similarity NPD7717 Approved
0.584 Remote Similarity NPD7716 Approved
0.5833 Remote Similarity NPD3967 Approved
0.5833 Remote Similarity NPD4559 Clinical (unspecified phase)
0.583 Remote Similarity NPD6470 Phase 3
0.5826 Remote Similarity NPD2819 Clinical (unspecified phase)
0.5826 Remote Similarity NPD3968 Approved
0.582 Remote Similarity NPD6465 Phase 2
0.5819 Remote Similarity NPD2411 Approved
0.5818 Remote Similarity NPD3517 Clinical (unspecified phase)
0.5804 Remote Similarity NPD4364 Phase 1
0.5799 Remote Similarity NPD1250 Clinical (unspecified phase)
0.5789 Remote Similarity NPD6288 Clinical (unspecified phase)
0.5789 Remote Similarity NPD8169 Discontinued
0.5781 Remote Similarity NPD6210 Phase 3
0.578 Remote Similarity NPD5820 Clinical (unspecified phase)
0.5776 Remote Similarity NPD4863 Approved
0.5761 Remote Similarity NPD8317 Phase 2
0.5761 Remote Similarity NPD8316 Phase 2
0.5759 Remote Similarity NPD1952 Discontinued
0.5759 Remote Similarity NPD5446 Phase 2
0.5753 Remote Similarity NPD3246 Discontinued
0.5747 Remote Similarity NPD6180 Clinical (unspecified phase)
0.5745 Remote Similarity NPD3353 Approved
0.5743 Remote Similarity NPD499 Phase 3
0.5743 Remote Similarity NPD3914 Clinical (unspecified phase)
0.5742 Remote Similarity NPD8484 Phase 2
0.574 Remote Similarity NPD5853 Phase 3
0.574 Remote Similarity NPD5855 Phase 3
0.5739 Remote Similarity NPD8322 Phase 2
0.5733 Remote Similarity NPD7809 Clinical (unspecified phase)
0.5727 Remote Similarity NPD5017 Discontinued
0.5727 Remote Similarity NPD5333 Clinical (unspecified phase)
0.5726 Remote Similarity NPD5887 Clinical (unspecified phase)
0.5721 Remote Similarity NPD2590 Clinical (unspecified phase)
0.572 Remote Similarity NPD2787 Clinical (unspecified phase)
0.572 Remote Similarity NPD5985 Phase 2
0.5714 Remote Similarity NPD4643 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3319 Phase 1
0.5714 Remote Similarity NPD3318 Approved
0.5714 Remote Similarity NPD3320 Approved
0.5708 Remote Similarity NPD3347 Clinical (unspecified phase)
0.5708 Remote Similarity NPD5854 Approved
0.5696 Remote Similarity NPD6271 Approved
0.5696 Remote Similarity NPD4541 Clinical (unspecified phase)
0.5685 Remote Similarity NPD5986 Approved
0.5685 Remote Similarity NPD5987 Approved
0.5685 Remote Similarity NPD3360 Clinical (unspecified phase)
0.5676 Remote Similarity NPD1658 Discontinued
0.5674 Remote Similarity NPD5840 Discontinued
0.5668 Remote Similarity NPD1783 Clinical (unspecified phase)
0.5657 Remote Similarity NPD569 Clinical (unspecified phase)
0.5652 Remote Similarity NPD8098 Approved
0.565 Remote Similarity NPD5974 Approved
0.565 Remote Similarity NPD1896 Approved
0.565 Remote Similarity NPD5973 Phase 2
0.5647 Remote Similarity NPD6459 Phase 2
0.5642 Remote Similarity NPD3512 Clinical (unspecified phase)
0.5641 Remote Similarity NPD3915 Approved
0.564 Remote Similarity NPD438 Approved
0.564 Remote Similarity NPD2392 Clinical (unspecified phase)
0.564 Remote Similarity NPD439 Approved
0.564 Remote Similarity NPD2642 Approved
0.564 Remote Similarity NPD2639 Approved
0.5639 Remote Similarity NPD6264 Discontinued
0.5638 Remote Similarity NPD6165 Phase 2
0.5638 Remote Similarity NPD6164 Phase 2
0.5628 Remote Similarity NPD5906 Clinical (unspecified phase)
0.5625 Remote Similarity NPD1031 Discontinued
0.5622 Remote Similarity NPD5962 Phase 2
0.5619 Remote Similarity NPD6664 Approved
0.5617 Remote Similarity NPD8096 Phase 3
0.5617 Remote Similarity NPD8097 Phase 3
0.5617 Remote Similarity NPD3917 Approved
0.5617 Remote Similarity NPD3916 Clinical (unspecified phase)
0.5617 Remote Similarity NPD8458 Clinical (unspecified phase)
0.5617 Remote Similarity NPD3918 Approved
0.5616 Remote Similarity NPD1096 Discontinued
0.5615 Remote Similarity NPD5415 Approved
0.5614 Remote Similarity NPD4961 Approved
0.5613 Remote Similarity NPD2185 Clinical (unspecified phase)
0.5602 Remote Similarity NPD3041 Approved
0.5602 Remote Similarity NPD7065 Clinical (unspecified phase)
0.5602 Remote Similarity NPD7865 Approved
0.56 Remote Similarity NPD7618 Phase 3
0.56 Remote Similarity NPD7619 Phase 3
0.56 Remote Similarity NPD7406 Phase 2

Structure

External Identifiers

PubChem CID   11263058
ChEMBL   CHEMBL1162474
ZINC  

Physicochemical Properties

Molecular Weight:  894.85
ALogP:  -0.2411
MLogP:  1.79
XLogP:  3.684
# Rotatable Bonds:  19
Polar Surface Area:  260.71
# H-Bond Aceptor:  16
# H-Bond Donor:  11
# Rings:  4
# Heavy Atoms:  45

Download Data

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