Natural Product: NPC476524

Natural Product ID:  NPC476524
Common Name:   Nakamuric Acid
IUPAC Name:   (1S,2S,3R,4R)-2-(2-amino-1H-imidazol-3-ium-5-yl)-3,4-bis[[(4-bromo-1H-pyrrole-2-carbonyl)amino]methyl]cyclobutane-1-carboxylic acid
Synonyms:   Nakamuric Acid
Molecular Formula:   C20H21Br2N7O4.C2HF3O2
Standard InCHIKey:  ILVGNSGRFLSMAS-XYAJGTTDSA-N
Standard InCHI:  InChI=1S/C20H21Br2N7O4.C2HF3O2/c21-8-1-12(24-3-8)17(30)26-5-10-11(6-27-18(31)13-2-9(22)4-25-13)16(19(32)33)15(10)14-7-28-20(23)29-14;3-2(4,5)1(6)7/h1-4,7,10-11,15-16,24-25H,5-6H2,(H,26,30)(H,27,31)(H,32,33)(H3,23,28,29);(H,6,7)/t10-,11-,15-,16+;/m1./s1
Canonical SMILES:  OC(=O)C(F)(F)F.N=c1[nH]cc([nH]1)[C@H]1[C@H](CNC(=O)c2[nH]cc(c2)Br)[C@H]([C@@H]1C(=O)O)CNC(=O)c1[nH]cc(c1)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
NPO11199 Agelas nakamurai Species Agelasidae Eukaryota at a depth of 14 m near the island of Ambon (Seram Seilale), Indonesia 1997-AUG PMID[10514317]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT2709 Organism Bacillus subtilis subsp. subtilis str. 168 Bacillus subtilis subsp. subtilis str. 168 IZ = 9 mm 10514317

  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 NPC476524 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
0.9679 High Similarity NPC476525
0.8989 High Similarity NPC329765
0.8989 High Similarity NPC476526
0.8989 High Similarity NPC48117
0.8743 High Similarity NPC475286
0.8743 High Similarity NPC174281
0.8653 High Similarity NPC19696
0.8653 High Similarity NPC136957
0.848 Intermediate Similarity NPC469717
0.8466 Intermediate Similarity NPC476527
0.8299 Intermediate Similarity NPC19342
0.8177 Intermediate Similarity NPC111566
0.8135 Intermediate Similarity NPC310633
0.8075 Intermediate Similarity NPC54214
0.799 Intermediate Similarity NPC63571
0.7921 Intermediate Similarity NPC9635
0.7807 Intermediate Similarity NPC206148
0.7709 Intermediate Similarity NPC66642
0.7696 Intermediate Similarity NPC469976
0.765 Intermediate Similarity NPC210123
0.7633 Intermediate Similarity NPC473376
0.7602 Intermediate Similarity NPC184932
0.7602 Intermediate Similarity NPC472861
0.7574 Intermediate Similarity NPC476414
0.7536 Intermediate Similarity NPC469716
0.7525 Intermediate Similarity NPC469814
0.7525 Intermediate Similarity NPC476413
0.7487 Intermediate Similarity NPC136441
0.7487 Intermediate Similarity NPC476423
0.7462 Intermediate Similarity NPC40530
0.7462 Intermediate Similarity NPC314281
0.7454 Intermediate Similarity NPC475736
0.7435 Intermediate Similarity NPC476418
0.7435 Intermediate Similarity NPC73687
0.7407 Intermediate Similarity NPC27296
0.7349 Intermediate Similarity NPC54744
0.7347 Intermediate Similarity NPC37268
0.7333 Intermediate Similarity NPC476421
0.7333 Intermediate Similarity NPC227489
0.7333 Intermediate Similarity NPC28096
0.7309 Intermediate Similarity NPC156003
0.7296 Intermediate Similarity NPC271927
0.726 Intermediate Similarity NPC474389
0.7259 Intermediate Similarity NPC97106
0.7245 Intermediate Similarity NPC226835
0.7233 Intermediate Similarity NPC188821
0.7233 Intermediate Similarity NPC474180
0.7227 Intermediate Similarity NPC474195
0.7216 Intermediate Similarity NPC474383
0.7214 Intermediate Similarity NPC270834
0.7208 Intermediate Similarity NPC80528
0.7189 Intermediate Similarity NPC470703
0.7175 Intermediate Similarity NPC474196
0.7143 Intermediate Similarity NPC293917
0.7143 Intermediate Similarity NPC473218
0.7143 Intermediate Similarity NPC470702
0.7112 Intermediate Similarity NPC201831
0.7112 Intermediate Similarity NPC17487
0.711 Intermediate Similarity NPC282247
0.7108 Intermediate Similarity NPC112489
0.7108 Intermediate Similarity NPC46022
0.7097 Intermediate Similarity NPC320968
0.7095 Intermediate Similarity NPC171317
0.7092 Intermediate Similarity NPC474696
0.7082 Intermediate Similarity NPC477109
0.7082 Intermediate Similarity NPC477107
0.7082 Intermediate Similarity NPC477108
0.7062 Intermediate Similarity NPC473706
0.7062 Intermediate Similarity NPC477004
0.7041 Intermediate Similarity NPC233380
0.7039 Intermediate Similarity NPC213629
0.7033 Intermediate Similarity NPC46811
0.703 Intermediate Similarity NPC16659
0.7015 Intermediate Similarity NPC240088
0.7015 Intermediate Similarity NPC473380
0.7014 Intermediate Similarity NPC131887
0.7 Intermediate Similarity NPC77061
0.699 Remote Similarity NPC17059
0.698 Remote Similarity NPC265710
0.6974 Remote Similarity NPC69843
0.6967 Remote Similarity NPC262898
0.6957 Remote Similarity NPC321708
0.6954 Remote Similarity NPC2414
0.6919 Remote Similarity NPC179701
0.6909 Remote Similarity NPC471194
0.6909 Remote Similarity NPC469715
0.6909 Remote Similarity NPC471193
0.6903 Remote Similarity NPC64216
0.689 Remote Similarity NPC476460
0.6883 Remote Similarity NPC474357
0.6875 Remote Similarity NPC471536
0.687 Remote Similarity NPC470323
0.6869 Remote Similarity NPC269203
0.6869 Remote Similarity NPC77241
0.6869 Remote Similarity NPC13456
0.6869 Remote Similarity NPC166209
0.6864 Remote Similarity NPC72956
0.6864 Remote Similarity NPC82370
0.6861 Remote Similarity NPC477114
0.6857 Remote Similarity NPC473342
0.6857 Remote Similarity NPC477167
0.6849 Remote Similarity NPC478158
0.6845 Remote Similarity NPC477003
0.6842 Remote Similarity NPC260041
0.684 Remote Similarity NPC935
0.684 Remote Similarity NPC267078
0.684 Remote Similarity NPC63031
0.6839 Remote Similarity NPC472260
0.6835 Remote Similarity NPC54420
0.6833 Remote Similarity NPC153980
0.6833 Remote Similarity NPC6865
0.6822 Remote Similarity NPC475914
0.6822 Remote Similarity NPC220797
0.6822 Remote Similarity NPC268744
0.6822 Remote Similarity NPC153123
0.6822 Remote Similarity NPC201266
0.6822 Remote Similarity NPC474318
0.6816 Remote Similarity NPC147983
0.6816 Remote Similarity NPC177996
0.6814 Remote Similarity NPC283219
0.6812 Remote Similarity NPC311282
0.6806 Remote Similarity NPC476073
0.6787 Remote Similarity NPC54981
0.6779 Remote Similarity NPC94752
0.6777 Remote Similarity NPC477166
0.6777 Remote Similarity NPC304187
0.6776 Remote Similarity NPC67288
0.6774 Remote Similarity NPC317701
0.6773 Remote Similarity NPC162860
0.6769 Remote Similarity NPC33229
0.6767 Remote Similarity NPC89987
0.6765 Remote Similarity NPC111275
0.6763 Remote Similarity NPC228835
0.6757 Remote Similarity NPC75634
0.6749 Remote Similarity NPC203468
0.6749 Remote Similarity NPC110500
0.6749 Remote Similarity NPC149155
0.6745 Remote Similarity NPC88315
0.6744 Remote Similarity NPC100321
0.6741 Remote Similarity NPC471192
0.6734 Remote Similarity NPC242872
0.6734 Remote Similarity NPC263117
0.6734 Remote Similarity NPC125181
0.6733 Remote Similarity NPC302647
0.6732 Remote Similarity NPC126709
0.6732 Remote Similarity NPC248041
0.6716 Remote Similarity NPC267885
0.6716 Remote Similarity NPC78020
0.6714 Remote Similarity NPC202812
0.6714 Remote Similarity NPC209917
0.6699 Remote Similarity NPC62749
0.6699 Remote Similarity NPC235684
0.6698 Remote Similarity NPC473640
0.6696 Remote Similarity NPC478157
0.6684 Remote Similarity NPC474236
0.6682 Remote Similarity NPC475506
0.6681 Remote Similarity NPC229893
0.6667 Remote Similarity NPC476491
0.6667 Remote Similarity NPC150592
0.6652 Remote Similarity NPC168209
0.6652 Remote Similarity NPC116555
0.6652 Remote Similarity NPC71238
0.6651 Remote Similarity NPC227582
0.6651 Remote Similarity NPC155143
0.6651 Remote Similarity NPC99939
0.6651 Remote Similarity NPC308931
0.665 Remote Similarity NPC306160
0.665 Remote Similarity NPC55772
0.665 Remote Similarity NPC162268
0.6638 Remote Similarity NPC243633
0.6638 Remote Similarity NPC175150
0.6637 Remote Similarity NPC267811
0.6637 Remote Similarity NPC472285
0.6634 Remote Similarity NPC476419
0.6622 Remote Similarity NPC107077
0.6622 Remote Similarity NPC223791
0.6608 Remote Similarity NPC281049
0.6607 Remote Similarity NPC207020
0.6606 Remote Similarity NPC52909
0.6606 Remote Similarity NPC94211
0.6606 Remote Similarity NPC475935
0.6602 Remote Similarity NPC145885
0.6602 Remote Similarity NPC14113
0.6602 Remote Similarity NPC84827
0.6599 Remote Similarity NPC74619
0.6598 Remote Similarity NPC477418
0.6598 Remote Similarity NPC477420
0.6593 Remote Similarity NPC36405
0.659 Remote Similarity NPC237414
0.6588 Remote Similarity NPC278434
0.6581 Remote Similarity NPC474877
0.6581 Remote Similarity NPC475969
0.6581 Remote Similarity NPC475859
0.6573 Remote Similarity NPC243716
0.657 Remote Similarity NPC11126
0.6564 Remote Similarity NPC238945
0.6561 Remote Similarity NPC82053
0.656 Remote Similarity NPC303820
0.656 Remote Similarity NPC23420
0.656 Remote Similarity NPC205254

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC476524 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
0.7427 Intermediate Similarity NPD7459 Phase 2
0.7235 Intermediate Similarity NPD7970 Approved
0.7235 Intermediate Similarity NPD7971 Clinical (unspecified phase)
0.723 Intermediate Similarity NPD8493 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD7621 Clinical (unspecified phase)
0.7083 Intermediate Similarity NPD276 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD2290 Phase 3
0.7081 Intermediate Similarity NPD2289 Phase 3
0.7079 Intermediate Similarity NPD3178 Discontinued
0.7018 Intermediate Similarity NPD8013 Clinical (unspecified phase)
0.6941 Remote Similarity NPD3915 Approved
0.6927 Remote Similarity NPD2091 Phase 2
0.6927 Remote Similarity NPD2096 Phase 2
0.6912 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6912 Remote Similarity NPD3411 Phase 2
0.6912 Remote Similarity NPD3410 Approved
0.6909 Remote Similarity NPD3918 Approved
0.6909 Remote Similarity NPD3916 Clinical (unspecified phase)
0.6909 Remote Similarity NPD3917 Approved
0.6895 Remote Similarity NPD7809 Clinical (unspecified phase)
0.6878 Remote Similarity NPD2094 Phase 2
0.6878 Remote Similarity NPD2095 Phase 2
0.6878 Remote Similarity NPD2092 Phase 2
0.6849 Remote Similarity NPD5510 Approved
0.6849 Remote Similarity NPD3968 Approved
0.6845 Remote Similarity NPD1096 Discontinued
0.6837 Remote Similarity NPD5017 Discontinued
0.682 Remote Similarity NPD5426 Phase 3
0.6818 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6816 Remote Similarity NPD3353 Approved
0.6773 Remote Similarity NPD7704 Clinical (unspecified phase)
0.6759 Remote Similarity NPD7903 Clinical (unspecified phase)
0.6749 Remote Similarity NPD482 Approved
0.6745 Remote Similarity NPD460 Discontinued
0.6739 Remote Similarity NPD6165 Phase 2
0.6739 Remote Similarity NPD6164 Phase 2
0.6727 Remote Similarity NPD2443 Approved
0.6727 Remote Similarity NPD2442 Approved
0.6716 Remote Similarity NPD749 Clinical (unspecified phase)
0.6715 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6712 Remote Similarity NPD3967 Approved
0.6712 Remote Similarity NPD2008 Discontinued
0.6697 Remote Similarity NPD1600 Suspended
0.6696 Remote Similarity NPD6210 Phase 3
0.6637 Remote Similarity NPD8406 Clinical (unspecified phase)
0.6637 Remote Similarity NPD7470 Discontinued
0.6636 Remote Similarity NPD4559 Clinical (unspecified phase)
0.6609 Remote Similarity NPD6173 Approved
0.6609 Remote Similarity NPD6753 Phase 1
0.6609 Remote Similarity NPD6752 Phase 1
0.6608 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6607 Remote Similarity NPD2411 Approved
0.6607 Remote Similarity NPD7594 Clinical (unspecified phase)
0.6604 Remote Similarity NPD5685 Approved
0.6604 Remote Similarity NPD5686 Approved
0.659 Remote Similarity NPD6999 Discontinued
0.659 Remote Similarity NPD7000 Clinical (unspecified phase)
0.6579 Remote Similarity NPD5199 Approved
0.6579 Remote Similarity NPD5198 Approved
0.6573 Remote Similarity NPD5592 Clinical (unspecified phase)
0.6573 Remote Similarity NPD6180 Clinical (unspecified phase)
0.6565 Remote Similarity NPD5001 Clinical (unspecified phase)
0.6552 Remote Similarity NPD7711 Discontinued
0.6547 Remote Similarity NPD2408 Discontinued
0.6532 Remote Similarity NPD1506 Discontinued
0.652 Remote Similarity NPD1573 Approved
0.652 Remote Similarity NPD1575 Approved
0.6516 Remote Similarity NPD5901 Discontinued
0.6514 Remote Similarity NPD2405 Phase 3
0.6505 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6498 Remote Similarity NPD2880 Discontinued
0.6496 Remote Similarity NPD7887 Approved
0.6496 Remote Similarity NPD7888 Approved
0.6491 Remote Similarity NPD8256 Approved
0.6491 Remote Similarity NPD8258 Clinical (unspecified phase)
0.6491 Remote Similarity NPD8257 Approved
0.6468 Remote Similarity NPD1982 Phase 1
0.6465 Remote Similarity NPD6665 Discontinued
0.6462 Remote Similarity NPD5820 Clinical (unspecified phase)
0.646 Remote Similarity NPD8096 Phase 3
0.646 Remote Similarity NPD8097 Phase 3
0.646 Remote Similarity NPD8458 Clinical (unspecified phase)
0.6456 Remote Similarity NPD750 Phase 2
0.6454 Remote Similarity NPD5461 Discontinued
0.6453 Remote Similarity NPD1568 Clinical (unspecified phase)
0.6452 Remote Similarity NPD7818 Clinical (unspecified phase)
0.6442 Remote Similarity NPD7865 Approved
0.6441 Remote Similarity NPD8169 Discontinued
0.6441 Remote Similarity NPD6288 Clinical (unspecified phase)
0.6441 Remote Similarity NPD8098 Approved
0.6432 Remote Similarity NPD8488 Clinical (unspecified phase)
0.6432 Remote Similarity NPD2009 Clinical (unspecified phase)
0.6429 Remote Similarity NPD7665 Phase 2
0.6429 Remote Similarity NPD7666 Phase 3
0.6425 Remote Similarity NPD3497 Clinical (unspecified phase)
0.6422 Remote Similarity NPD5611 Phase 2
0.6419 Remote Similarity NPD5643 Phase 2
0.6419 Remote Similarity NPD2787 Clinical (unspecified phase)
0.6417 Remote Similarity NPD3360 Clinical (unspecified phase)
0.6414 Remote Similarity NPD510 Phase 1
0.6404 Remote Similarity NPD6481 Clinical (unspecified phase)
0.6384 Remote Similarity NPD6328 Clinical (unspecified phase)
0.6383 Remote Similarity NPD8292 Phase 2
0.6381 Remote Similarity NPD6595 Phase 3
0.6376 Remote Similarity NPD6226 Phase 3
0.6368 Remote Similarity NPD8272 Phase 2
0.636 Remote Similarity NPD4341 Clinical (unspecified phase)
0.6359 Remote Similarity NPD4184 Clinical (unspecified phase)
0.6356 Remote Similarity NPD2510 Approved
0.6356 Remote Similarity NPD2509 Approved
0.6347 Remote Similarity NPD6664 Approved
0.6341 Remote Similarity NPD4558 Phase 2
0.634 Remote Similarity NPD5887 Clinical (unspecified phase)
0.6339 Remote Similarity NPD7001 Phase 3
0.6339 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6336 Remote Similarity NPD1996 Discontinued
0.6332 Remote Similarity NPD9343 Clinical (unspecified phase)
0.633 Remote Similarity NPD7619 Phase 3
0.633 Remote Similarity NPD7618 Phase 3
0.633 Remote Similarity NPD8641 Approved
0.6325 Remote Similarity NPD6850 Phase 2
0.6325 Remote Similarity NPD6849 Phase 2
0.6318 Remote Similarity NPD2947 Clinical (unspecified phase)
0.6314 Remote Similarity NPD7731 Approved
0.6314 Remote Similarity NPD7730 Approved
0.6311 Remote Similarity NPD2844 Phase 3
0.6311 Remote Similarity NPD8410 Clinical (unspecified phase)
0.6308 Remote Similarity NPD4426 Clinical (unspecified phase)
0.6306 Remote Similarity NPD7817 Phase 1
0.6305 Remote Similarity NPD3130 Discontinued
0.6298 Remote Similarity NPD1037 Clinical (unspecified phase)
0.6298 Remote Similarity NPD7271 Approved
0.6295 Remote Similarity NPD56 Approved
0.6295 Remote Similarity NPD8283 Approved
0.6295 Remote Similarity NPD3947 Discontinued
0.6295 Remote Similarity NPD3247 Clinical (unspecified phase)
0.6295 Remote Similarity NPD8282 Approved
0.6287 Remote Similarity NPD7781 Approved
0.6287 Remote Similarity NPD7780 Approved
0.6284 Remote Similarity NPD1173 Approved
0.6283 Remote Similarity NPD7232 Discontinued
0.6273 Remote Similarity NPD5446 Phase 2
0.627 Remote Similarity NPD7860 Clinical (unspecified phase)
0.6268 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6261 Remote Similarity NPD7824 Approved
0.6261 Remote Similarity NPD8112 Clinical (unspecified phase)
0.6261 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6255 Remote Similarity NPD7716 Approved
0.6255 Remote Similarity NPD7717 Approved
0.625 Remote Similarity NPD7789 Approved
0.625 Remote Similarity NPD7791 Approved
0.625 Remote Similarity NPD2180 Approved
0.625 Remote Similarity NPD2121 Clinical (unspecified phase)
0.625 Remote Similarity NPD6470 Phase 3
0.625 Remote Similarity NPD7953 Approved
0.625 Remote Similarity NPD7790 Approved
0.625 Remote Similarity NPD7950 Approved
0.625 Remote Similarity NPD7952 Approved
0.625 Remote Similarity NPD7951 Approved
0.625 Remote Similarity NPD3105 Discontinued
0.625 Remote Similarity NPD1623 Approved
0.6245 Remote Similarity NPD4852 Phase 2
0.6239 Remote Similarity NPD6838 Clinical (unspecified phase)
0.6228 Remote Similarity NPD7825 Clinical (unspecified phase)
0.6228 Remote Similarity NPD7465 Suspended
0.6226 Remote Similarity NPD3989 Phase 3
0.6224 Remote Similarity NPD6970 Phase 2
0.6217 Remote Similarity NPD7557 Clinical (unspecified phase)
0.6217 Remote Similarity NPD2823 Clinical (unspecified phase)
0.6217 Remote Similarity NPD8094 Discontinued
0.6211 Remote Similarity NPD4959 Approved
0.6211 Remote Similarity NPD6486 Approved
0.6211 Remote Similarity NPD6487 Approved
0.6211 Remote Similarity NPD6459 Phase 2
0.6211 Remote Similarity NPD4960 Approved
0.6207 Remote Similarity NPD2813 Phase 3
0.6207 Remote Similarity NPD8271 Discontinued
0.6207 Remote Similarity NPD8000 Clinical (unspecified phase)
0.6207 Remote Similarity NPD2812 Clinical (unspecified phase)
0.6204 Remote Similarity NPD3486 Clinical (unspecified phase)
0.6204 Remote Similarity NPD3914 Clinical (unspecified phase)
0.6199 Remote Similarity NPD1952 Discontinued
0.6197 Remote Similarity NPD3990 Phase 3
0.6197 Remote Similarity NPD3038 Discontinued
0.6195 Remote Similarity NPD8026 Phase 1
0.619 Remote Similarity NPD4883 Approved
0.619 Remote Similarity NPD2928 Phase 2
0.6189 Remote Similarity NPD2893 Phase 3
0.6188 Remote Similarity NPD484 Approved
0.6188 Remote Similarity NPD2061 Approved
0.6186 Remote Similarity NPD2814 Clinical (unspecified phase)
0.6186 Remote Similarity NPD4336 Clinical (unspecified phase)
0.6186 Remote Similarity NPD2803 Discontinued
0.6184 Remote Similarity NPD7941 Phase 3
0.6184 Remote Similarity NPD4174 Clinical (unspecified phase)
0.6183 Remote Similarity NPD7415 Suspended
0.6182 Remote Similarity NPD5855 Phase 3
0.6182 Remote Similarity NPD5853 Phase 3
0.618 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6172 Remote Similarity NPD3347 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   10628462;9987214
ChEMBL   CHEMBL474667
ZINC  

Physicochemical Properties

Molecular Weight:  581.00
ALogP:  -2.3101
MLogP:  2.23
XLogP:  1.626
# Rotatable Bonds:  13
Polar Surface Area:  174.99
# H-Bond Aceptor:  11
# H-Bond Donor:  8
# Rings:  4
# Heavy Atoms:  33

Download Data

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Biological Activities  
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