Natural Product: NPC111566

Natural Product ID:  NPC111566
Common Name:   Nagelamide D
IUPAC Name:   N-[3-[2-amino-4-[(1S)-1-(2-amino-1H-imidazol-5-yl)-3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)amino]propyl]-1H-imidazol-5-yl]propyl]-4,5-dibromo-1H-pyrrole-2-carboxamide
Synonyms:   Nagelamide D
Molecular Formula:   C22H24Br4N10O2
Standard InCHIKey:  MXRBWEXRDANRHZ-VIFPVBQESA-N
Standard InCHI:  InChI=1S/C22H24Br4N10O2/c23-10-6-13(32-17(10)25)19(37)29-4-1-2-12-16(36-22(28)34-12)9(15-8-31-21(27)35-15)3-5-30-20(38)14-7-11(24)18(26)33-14/h6-9,32-33H,1-5H2,(H,29,37)(H,30,38)(H3,27,31,35)(H3,28,34,36)/t9-/m0/s1
Canonical SMILES:  N=c1[nH]cc([nH]1)[C@@H](c1[nH]c(=N)[nH]c1CCCNC(=O)c1[nH]c(c(c1)Br)Br)CCNC(=O)c1[nH]c(c(c1)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
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 33.3 ug/ml 22079755
NPT729 Organism Micrococcus luteus Micrococcus luteus MIC = 4.17 ug/ml 19128055
NPT19 Organism Escherichia coli Escherichia coli 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 NPC111566 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
0.994 High Similarity NPC310633
0.976 High Similarity NPC63571
0.9649 High Similarity NPC19342
0.927 High Similarity NPC9635
0.9266 High Similarity NPC136957
0.9266 High Similarity NPC19696
0.9153 High Similarity NPC475286
0.9153 High Similarity NPC174281
0.9096 High Similarity NPC476526
0.9096 High Similarity NPC329765
0.9096 High Similarity NPC48117
0.8916 High Similarity NPC206148
0.8696 High Similarity NPC469716
0.8549 High Similarity NPC469717
0.8539 High Similarity NPC476527
0.8363 Intermediate Similarity NPC73687
0.8333 Intermediate Similarity NPC54214
0.8229 Intermediate Similarity NPC28096
0.8229 Intermediate Similarity NPC476421
0.8229 Intermediate Similarity NPC469976
0.8229 Intermediate Similarity NPC227489
0.8192 Intermediate Similarity NPC136441
0.8177 Intermediate Similarity NPC476525
0.8177 Intermediate Similarity NPC476524
0.815 Intermediate Similarity NPC476418
0.8125 Intermediate Similarity NPC226835
0.8011 Intermediate Similarity NPC472861
0.8011 Intermediate Similarity NPC184932
0.7877 Intermediate Similarity NPC80528
0.7833 Intermediate Similarity NPC97106
0.7826 Intermediate Similarity NPC469814
0.7811 Intermediate Similarity NPC260041
0.7735 Intermediate Similarity NPC37268
0.7684 Intermediate Similarity NPC476414
0.768 Intermediate Similarity NPC271927
0.7636 Intermediate Similarity NPC150592
0.7632 Intermediate Similarity NPC476413
0.7568 Intermediate Similarity NPC40530
0.7568 Intermediate Similarity NPC314281
0.747 Intermediate Similarity NPC20021
0.7459 Intermediate Similarity NPC474696
0.7416 Intermediate Similarity NPC27296
0.7403 Intermediate Similarity NPC2414
0.7396 Intermediate Similarity NPC210123
0.7368 Intermediate Similarity NPC46022
0.7368 Intermediate Similarity NPC112489
0.7303 Intermediate Similarity NPC474236
0.7253 Intermediate Similarity NPC306160
0.7213 Intermediate Similarity NPC474383
0.7211 Intermediate Similarity NPC270834
0.7175 Intermediate Similarity NPC66642
0.7143 Intermediate Similarity NPC474180
0.7143 Intermediate Similarity NPC188821
0.7107 Intermediate Similarity NPC46811
0.7085 Intermediate Similarity NPC474389
0.7049 Intermediate Similarity NPC473706
0.7019 Intermediate Similarity NPC470703
0.6971 Remote Similarity NPC470702
0.6971 Remote Similarity NPC473218
0.6959 Remote Similarity NPC476423
0.6906 Remote Similarity NPC472260
0.6881 Remote Similarity NPC477004
0.6839 Remote Similarity NPC16659
0.6823 Remote Similarity NPC240088
0.6823 Remote Similarity NPC473380
0.6788 Remote Similarity NPC265710
0.6755 Remote Similarity NPC233380
0.6738 Remote Similarity NPC253687
0.673 Remote Similarity NPC469715
0.6712 Remote Similarity NPC474357
0.6697 Remote Similarity NPC470323
0.6683 Remote Similarity NPC166209
0.6683 Remote Similarity NPC269203
0.6683 Remote Similarity NPC77241
0.6683 Remote Similarity NPC13456
0.6667 Remote Similarity NPC935
0.6667 Remote Similarity NPC267078
0.6634 Remote Similarity NPC268744
0.6634 Remote Similarity NPC475914
0.6634 Remote Similarity NPC220797
0.6634 Remote Similarity NPC153123
0.6634 Remote Similarity NPC201266
0.6634 Remote Similarity NPC474318
0.6616 Remote Similarity NPC133003
0.6591 Remote Similarity NPC291517
0.6591 Remote Similarity NPC23215
0.659 Remote Similarity NPC474195
0.6589 Remote Similarity NPC50562
0.6576 Remote Similarity NPC52110
0.6574 Remote Similarity NPC475736
0.6566 Remote Similarity NPC477003
0.6558 Remote Similarity NPC67658
0.6556 Remote Similarity NPC101130
0.6556 Remote Similarity NPC58268
0.6556 Remote Similarity NPC114033
0.6556 Remote Similarity NPC129412
0.6546 Remote Similarity NPC186068
0.6545 Remote Similarity NPC474196
0.6535 Remote Similarity NPC476460
0.6532 Remote Similarity NPC156003
0.6524 Remote Similarity NPC142688
0.6517 Remote Similarity NPC473666
0.6515 Remote Similarity NPC470205
0.6507 Remote Similarity NPC317701
0.6485 Remote Similarity NPC324091
0.6462 Remote Similarity NPC116555
0.6461 Remote Similarity NPC14448
0.6461 Remote Similarity NPC195704
0.6461 Remote Similarity NPC200397
0.6461 Remote Similarity NPC292434
0.6461 Remote Similarity NPC64661
0.6461 Remote Similarity NPC167200
0.6461 Remote Similarity NPC98156
0.6461 Remote Similarity NPC138596
0.644 Remote Similarity NPC247987
0.6432 Remote Similarity NPC117027
0.6418 Remote Similarity NPC141612
0.6418 Remote Similarity NPC135601
0.6418 Remote Similarity NPC17273
0.641 Remote Similarity NPC161861
0.6409 Remote Similarity NPC286529
0.6409 Remote Similarity NPC209281
0.6409 Remote Similarity NPC48171
0.6409 Remote Similarity NPC59839
0.6409 Remote Similarity NPC169308
0.6409 Remote Similarity NPC77582
0.6409 Remote Similarity NPC205604
0.6409 Remote Similarity NPC129753
0.6409 Remote Similarity NPC244087
0.6409 Remote Similarity NPC97230
0.6409 Remote Similarity NPC302717
0.6409 Remote Similarity NPC74928
0.6409 Remote Similarity NPC12831
0.6409 Remote Similarity NPC3698
0.64 Remote Similarity NPC21429
0.6398 Remote Similarity NPC473376
0.6394 Remote Similarity NPC237414
0.638 Remote Similarity NPC243633
0.638 Remote Similarity NPC175150
0.6376 Remote Similarity NPC267811
0.6368 Remote Similarity NPC308931
0.6368 Remote Similarity NPC99939
0.633 Remote Similarity NPC232798
0.6318 Remote Similarity NPC168209
0.631 Remote Similarity NPC471655
0.6308 Remote Similarity NPC471943
0.6305 Remote Similarity NPC473946
0.63 Remote Similarity NPC307191
0.6296 Remote Similarity NPC75135
0.6293 Remote Similarity NPC243716
0.6287 Remote Similarity NPC474258
0.6283 Remote Similarity NPC69843
0.6268 Remote Similarity NPC171317
0.6267 Remote Similarity NPC477413
0.625 Remote Similarity NPC477042
0.625 Remote Similarity NPC79356
0.625 Remote Similarity NPC102592
0.625 Remote Similarity NPC234403
0.6244 Remote Similarity NPC477611
0.6243 Remote Similarity NPC472288
0.6239 Remote Similarity NPC282247
0.6232 Remote Similarity NPC304203
0.6231 Remote Similarity NPC284775
0.6223 Remote Similarity NPC17487
0.6223 Remote Similarity NPC201831
0.6221 Remote Similarity NPC320968
0.6197 Remote Similarity NPC477107
0.6197 Remote Similarity NPC477108
0.6197 Remote Similarity NPC477109
0.619 Remote Similarity NPC109158
0.6186 Remote Similarity NPC274981
0.6181 Remote Similarity NPC151635
0.6169 Remote Similarity NPC88110
0.6169 Remote Similarity NPC79777
0.6169 Remote Similarity NPC91179
0.6164 Remote Similarity NPC54744
0.6158 Remote Similarity NPC110158
0.6154 Remote Similarity NPC326422
0.6146 Remote Similarity NPC17059
0.6126 Remote Similarity NPC33229
0.6126 Remote Similarity NPC298288
0.6122 Remote Similarity NPC109447
0.6119 Remote Similarity NPC471194
0.6119 Remote Similarity NPC471193
0.6117 Remote Similarity NPC213629
0.6114 Remote Similarity NPC474492
0.6106 Remote Similarity NPC304187
0.6106 Remote Similarity NPC477166
0.6106 Remote Similarity NPC477167
0.6106 Remote Similarity NPC473342
0.6098 Remote Similarity NPC94752
0.6096 Remote Similarity NPC204141
0.6095 Remote Similarity NPC77061
0.6078 Remote Similarity NPC228835
0.6078 Remote Similarity NPC108011
0.6073 Remote Similarity NPC72956
0.6071 Remote Similarity NPC272174
0.6071 Remote Similarity NPC17751
0.6071 Remote Similarity NPC280864
0.605 Remote Similarity NPC469529

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC111566 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
0.7526 Intermediate Similarity NPD7459 Phase 2
0.6818 Remote Similarity NPD5686 Approved
0.6818 Remote Similarity NPD5685 Approved
0.665 Remote Similarity NPD2289 Phase 3
0.665 Remote Similarity NPD2290 Phase 3
0.6619 Remote Similarity NPD2443 Approved
0.6619 Remote Similarity NPD2442 Approved
0.6588 Remote Similarity NPD7704 Clinical (unspecified phase)
0.6528 Remote Similarity NPD5643 Phase 2
0.6432 Remote Similarity NPD2408 Discontinued
0.6415 Remote Similarity NPD8493 Clinical (unspecified phase)
0.6415 Remote Similarity NPD1506 Discontinued
0.6393 Remote Similarity NPD5199 Approved
0.6393 Remote Similarity NPD5198 Approved
0.639 Remote Similarity NPD460 Discontinued
0.6368 Remote Similarity NPD2008 Discontinued
0.6355 Remote Similarity NPD1600 Suspended
0.6346 Remote Similarity NPD1982 Phase 1
0.6311 Remote Similarity NPD5274 Clinical (unspecified phase)
0.6305 Remote Similarity NPD2009 Clinical (unspecified phase)
0.6298 Remote Similarity NPD2880 Discontinued
0.6293 Remote Similarity NPD5592 Clinical (unspecified phase)
0.629 Remote Similarity NPD6579 Phase 2
0.6277 Remote Similarity NPD9343 Clinical (unspecified phase)
0.6267 Remote Similarity NPD2411 Approved
0.6256 Remote Similarity NPD6837 Clinical (unspecified phase)
0.6256 Remote Similarity NPD5820 Clinical (unspecified phase)
0.6244 Remote Similarity NPD6288 Clinical (unspecified phase)
0.6238 Remote Similarity NPD2405 Phase 3
0.6214 Remote Similarity NPD6180 Clinical (unspecified phase)
0.6193 Remote Similarity NPD7656 Approved
0.6193 Remote Similarity NPD7657 Approved
0.6161 Remote Similarity NPD5001 Clinical (unspecified phase)
0.6154 Remote Similarity NPD8256 Approved
0.6154 Remote Similarity NPD8258 Clinical (unspecified phase)
0.6154 Remote Similarity NPD8257 Approved
0.6143 Remote Similarity NPD5446 Phase 2
0.6143 Remote Similarity NPD1952 Discontinued
0.6136 Remote Similarity NPD7971 Clinical (unspecified phase)
0.6136 Remote Similarity NPD7970 Approved
0.6126 Remote Similarity NPD6470 Phase 3
0.6119 Remote Similarity NPD2590 Clinical (unspecified phase)
0.6111 Remote Similarity NPD6328 Clinical (unspecified phase)
0.6111 Remote Similarity NPD3347 Clinical (unspecified phase)
0.6108 Remote Similarity NPD3319 Phase 1
0.6108 Remote Similarity NPD3318 Approved
0.6108 Remote Similarity NPD3320 Approved
0.6103 Remote Similarity NPD5017 Discontinued
0.6103 Remote Similarity NPD7817 Phase 1
0.61 Remote Similarity NPD2367 Phase 2
0.6087 Remote Similarity NPD569 Clinical (unspecified phase)
0.6083 Remote Similarity NPD6459 Phase 2
0.6068 Remote Similarity NPD3246 Discontinued
0.6067 Remote Similarity NPD1031 Discontinued
0.6065 Remote Similarity NPD3967 Approved
0.6059 Remote Similarity NPD3178 Discontinued
0.6055 Remote Similarity NPD2819 Clinical (unspecified phase)
0.6048 Remote Similarity NPD5855 Phase 3
0.6048 Remote Similarity NPD5853 Phase 3
0.6038 Remote Similarity NPD465 Clinical (unspecified phase)
0.6037 Remote Similarity NPD3411 Phase 2
0.6037 Remote Similarity NPD3410 Approved
0.6034 Remote Similarity NPD6465 Phase 2
0.6029 Remote Similarity NPD7098 Clinical (unspecified phase)
0.6028 Remote Similarity NPD3890 Phase 2
0.6028 Remote Similarity NPD3891 Phase 2
0.6027 Remote Similarity NPD7809 Clinical (unspecified phase)
0.6019 Remote Similarity NPD4426 Clinical (unspecified phase)
0.6009 Remote Similarity NPD5854 Approved
0.6 Remote Similarity NPD4863 Approved
0.6 Remote Similarity NPD6210 Phase 3
0.5991 Remote Similarity NPD4559 Clinical (unspecified phase)
0.5991 Remote Similarity NPD7716 Approved
0.5991 Remote Similarity NPD6664 Approved
0.5991 Remote Similarity NPD7717 Approved
0.599 Remote Similarity NPD7865 Approved
0.5982 Remote Similarity NPD3968 Approved
0.5981 Remote Similarity NPD1658 Discontinued
0.598 Remote Similarity NPD1783 Clinical (unspecified phase)
0.5969 Remote Similarity NPD971 Clinical (unspecified phase)
0.5962 Remote Similarity NPD1250 Clinical (unspecified phase)
0.596 Remote Similarity NPD438 Approved
0.596 Remote Similarity NPD439 Approved
0.5957 Remote Similarity NPD3360 Clinical (unspecified phase)
0.5952 Remote Similarity NPD5973 Phase 2
0.5952 Remote Similarity NPD5974 Approved
0.5926 Remote Similarity NPD175 Clinical (unspecified phase)
0.5926 Remote Similarity NPD4134 Clinical (unspecified phase)
0.5926 Remote Similarity NPD6269 Clinical (unspecified phase)
0.5926 Remote Similarity NPD6268 Phase 1
0.5922 Remote Similarity NPD1096 Discontinued
0.5917 Remote Similarity NPD6271 Approved
0.5913 Remote Similarity NPD6164 Phase 2
0.5913 Remote Similarity NPD6165 Phase 2
0.5913 Remote Similarity NPD3486 Clinical (unspecified phase)
0.5911 Remote Similarity NPD4541 Clinical (unspecified phase)
0.5896 Remote Similarity NPD7618 Phase 3
0.5896 Remote Similarity NPD7619 Phase 3
0.5896 Remote Similarity NPD7406 Phase 2
0.5893 Remote Similarity NPD3353 Approved
0.5885 Remote Similarity NPD1284 Clinical (unspecified phase)
0.5882 Remote Similarity NPD3077 Approved
0.5882 Remote Similarity NPD3078 Approved
0.5882 Remote Similarity NPD3076 Approved
0.5882 Remote Similarity NPD3079 Approved
0.5879 Remote Similarity NPD2392 Clinical (unspecified phase)
0.5877 Remote Similarity NPD1896 Approved
0.5877 Remote Similarity NPD4922 Phase 2
0.5874 Remote Similarity NPD2363 Discontinued
0.5872 Remote Similarity NPD7209 Approved
0.5872 Remote Similarity NPD7208 Approved
0.5872 Remote Similarity NPD7207 Approved
0.587 Remote Similarity NPD272 Approved
0.587 Remote Similarity NPD5887 Clinical (unspecified phase)
0.5869 Remote Similarity NPD7027 Phase 3
0.5865 Remote Similarity NPD7026 Phase 2
0.586 Remote Similarity NPD7621 Clinical (unspecified phase)
0.5856 Remote Similarity NPD8013 Clinical (unspecified phase)
0.5855 Remote Similarity NPD8047 Clinical (unspecified phase)
0.5854 Remote Similarity NPD5473 Discontinued
0.5854 Remote Similarity NPD5962 Phase 2
0.5851 Remote Similarity NPD3834 Clinical (unspecified phase)
0.5848 Remote Similarity NPD4395 Phase 1
0.5845 Remote Similarity NPD3607 Clinical (unspecified phase)
0.5837 Remote Similarity NPD8317 Phase 2
0.5837 Remote Similarity NPD4988 Discontinued
0.5837 Remote Similarity NPD8316 Phase 2
0.5833 Remote Similarity NPD3041 Approved
0.5829 Remote Similarity NPD2892 Phase 1
0.5829 Remote Similarity NPD1568 Clinical (unspecified phase)
0.5821 Remote Similarity NPD1573 Approved
0.5821 Remote Similarity NPD1575 Approved
0.582 Remote Similarity NPD2007 Clinical (unspecified phase)
0.5818 Remote Similarity NPD8322 Phase 2
0.5814 Remote Similarity NPD2947 Clinical (unspecified phase)
0.5813 Remote Similarity NPD4736 Clinical (unspecified phase)
0.5813 Remote Similarity NPD4883 Approved
0.5799 Remote Similarity NPD8098 Approved
0.5799 Remote Similarity NPD5426 Phase 3
0.5799 Remote Similarity NPD4299 Phase 1
0.5799 Remote Similarity NPD3247 Clinical (unspecified phase)
0.5799 Remote Similarity NPD8169 Discontinued
0.5796 Remote Similarity NPD2787 Clinical (unspecified phase)
0.5795 Remote Similarity NPD1003 Phase 2
0.5794 Remote Similarity NPD1871 Approved
0.5792 Remote Similarity NPD6828 Phase 2
0.5792 Remote Similarity NPD6827 Clinical (unspecified phase)
0.5789 Remote Similarity NPD4940 Approved
0.5785 Remote Similarity NPD3915 Approved
0.5784 Remote Similarity NPD4075 Phase 2
0.578 Remote Similarity NPD2881 Approved
0.578 Remote Similarity NPD6802 Phase 3
0.578 Remote Similarity NPD2879 Approved
0.5778 Remote Similarity NPD2547 Discontinued
0.5777 Remote Similarity NPD3927 Phase 2
0.5775 Remote Similarity NPD3460 Discontinued
0.5773 Remote Similarity NPD5489 Phase 1
0.5773 Remote Similarity NPD5491 Phase 3
0.5771 Remote Similarity NPD1623 Approved
0.5766 Remote Similarity NPD5510 Approved
0.5762 Remote Similarity NPD3961 Discontinued
0.5761 Remote Similarity NPD4558 Phase 2
0.5759 Remote Similarity NPD8096 Phase 3
0.5759 Remote Similarity NPD8097 Phase 3
0.5759 Remote Similarity NPD3917 Approved
0.5759 Remote Similarity NPD3918 Approved
0.5759 Remote Similarity NPD3916 Clinical (unspecified phase)
0.5758 Remote Similarity NPD5986 Approved
0.5758 Remote Similarity NPD5987 Approved
0.5751 Remote Similarity NPD7887 Approved
0.5751 Remote Similarity NPD7888 Approved
0.5749 Remote Similarity NPD1895 Discontinued
0.5738 Remote Similarity NPD6986 Phase 1
0.5735 Remote Similarity NPD5016 Approved
0.5735 Remote Similarity NPD7175 Phase 1
0.5734 Remote Similarity NPD7903 Clinical (unspecified phase)
0.5734 Remote Similarity NPD7727 Phase 2
0.5729 Remote Similarity NPD6771 Discontinued
0.5728 Remote Similarity NPD2930 Clinical (unspecified phase)
0.5727 Remote Similarity NPD5000 Phase 2
0.5727 Remote Similarity NPD8115 Approved
0.5727 Remote Similarity NPD8114 Approved
0.5722 Remote Similarity NPD3835 Phase 3
0.5722 Remote Similarity NPD3833 Phase 3
0.5721 Remote Similarity NPD7232 Discontinued
0.5721 Remote Similarity NPD7401 Clinical (unspecified phase)
0.5721 Remote Similarity NPD1996 Discontinued
0.5721 Remote Similarity NPD7023 Clinical (unspecified phase)
0.5721 Remote Similarity NPD2478 Clinical (unspecified phase)
0.5721 Remote Similarity NPD4643 Clinical (unspecified phase)
0.5714 Remote Similarity NPD3913 Clinical (unspecified phase)
0.5714 Remote Similarity NPD6849 Phase 2
0.5714 Remote Similarity NPD9599 Approved
0.5714 Remote Similarity NPD2061 Approved
0.5714 Remote Similarity NPD6850 Phase 2
0.5714 Remote Similarity NPD2222 Discontinued
0.5714 Remote Similarity NPD6753 Phase 1
0.5714 Remote Similarity NPD6752 Phase 1
0.5707 Remote Similarity NPD803 Phase 1
0.5707 Remote Similarity NPD809 Discontinued

Structure

External Identifiers

PubChem CID   21777642
ChEMBL   CHEMBL1162470
ZINC  

Physicochemical Properties

Molecular Weight:  775.88
ALogP:  -1.3105
MLogP:  2.12
XLogP:  5.094
# Rotatable Bonds:  17
Polar Surface Area:  185.6
# H-Bond Aceptor:  12
# H-Bond Donor:  10
# Rings:  4
# Heavy Atoms:  38

Download Data

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Biological Activities  
Similar NPs/Drugs