Natural Product: NPC474383

Natural Product ID:  NPC474383
Common Name:   Longamide B
IUPAC Name:   2-[(4S)-6,7-dibromo-1-oxo-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-4-yl]acetic acid
Synonyms:  
Molecular Formula:   C9H8Br2N2O3
Standard InCHIKey:  DRDCMECERMJRNR-BYPYZUCNSA-N
Standard InCHI:  InChI=1S/C9H8Br2N2O3/c10-5-2-6-9(16)12-3-4(1-7(14)15)13(6)8(5)11/h2,4H,1,3H2,(H,12,16)(H,14,15)/t4-/m0/s1
Canonical SMILES:  OC(=O)C[C@H]1CNC(=O)c2n1c(Br)c(c2)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
NPO27799 Agelas dispar Species Agelasidae Eukaryota PMID[9461661]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT16 Organism Staphylococcus aureus Staphylococcus aureus MIC = 55 ug/ml PubChem BioAssay data set
NPT79 Organism Bacillus subtilis Bacillus subtilis MIC = 45 ug/ml PubChem BioAssay data set

  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 NPC474383 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
0.9536 High Similarity NPC27296
0.8903 High Similarity NPC474236
0.8571 High Similarity NPC476418
0.8363 Intermediate Similarity NPC476423
0.8344 Intermediate Similarity NPC306160
0.8333 Intermediate Similarity NPC473706
0.8314 Intermediate Similarity NPC112489
0.8314 Intermediate Similarity NPC46022
0.8274 Intermediate Similarity NPC136441
0.8217 Intermediate Similarity NPC260041
0.8214 Intermediate Similarity NPC97106
0.8204 Intermediate Similarity NPC227489
0.8204 Intermediate Similarity NPC28096
0.8204 Intermediate Similarity NPC476421
0.8095 Intermediate Similarity NPC226835
0.8092 Intermediate Similarity NPC469814
0.8039 Intermediate Similarity NPC150592
0.7989 Intermediate Similarity NPC46811
0.7857 Intermediate Similarity NPC20021
0.7836 Intermediate Similarity NPC80528
0.7798 Intermediate Similarity NPC206148
0.7751 Intermediate Similarity NPC2414
0.7744 Intermediate Similarity NPC109158
0.768 Intermediate Similarity NPC476413
0.7637 Intermediate Similarity NPC476414
0.7576 Intermediate Similarity NPC52110
0.7486 Intermediate Similarity NPC37268
0.7471 Intermediate Similarity NPC54214
0.7337 Intermediate Similarity NPC298288
0.7278 Intermediate Similarity NPC184932
0.7278 Intermediate Similarity NPC472861
0.7273 Intermediate Similarity NPC77061
0.7219 Intermediate Similarity NPC472260
0.7216 Intermediate Similarity NPC476524
0.7213 Intermediate Similarity NPC111566
0.7213 Intermediate Similarity NPC63571
0.7193 Intermediate Similarity NPC142688
0.7184 Intermediate Similarity NPC73687
0.7174 Intermediate Similarity NPC310633
0.7151 Intermediate Similarity NPC476419
0.7102 Intermediate Similarity NPC474696
0.7083 Intermediate Similarity NPC9635
0.7074 Intermediate Similarity NPC19342
0.7045 Intermediate Similarity NPC233380
0.7012 Intermediate Similarity NPC472288
0.6979 Remote Similarity NPC19696
0.6979 Remote Similarity NPC136957
0.6954 Remote Similarity NPC476525
0.6944 Remote Similarity NPC271927
0.694 Remote Similarity NPC314281
0.694 Remote Similarity NPC40530
0.6936 Remote Similarity NPC33229
0.6889 Remote Similarity NPC469976
0.6878 Remote Similarity NPC210123
0.6875 Remote Similarity NPC475286
0.6875 Remote Similarity NPC174281
0.6865 Remote Similarity NPC270834
0.6823 Remote Similarity NPC476526
0.6823 Remote Similarity NPC48117
0.6823 Remote Similarity NPC329765
0.68 Remote Similarity NPC74357
0.6788 Remote Similarity NPC23215
0.6788 Remote Similarity NPC291517
0.6786 Remote Similarity NPC469716
0.6732 Remote Similarity NPC469717
0.6718 Remote Similarity NPC477004
0.6702 Remote Similarity NPC311282
0.6702 Remote Similarity NPC133003
0.6687 Remote Similarity NPC71236
0.6667 Remote Similarity NPC50562
0.665 Remote Similarity NPC471944
0.6634 Remote Similarity NPC67658
0.659 Remote Similarity NPC302159
0.6573 Remote Similarity NPC213914
0.6569 Remote Similarity NPC469715
0.6564 Remote Similarity NPC179701
0.6554 Remote Similarity NPC209362
0.6554 Remote Similarity NPC75135
0.6552 Remote Similarity NPC105811
0.6541 Remote Similarity NPC186068
0.6532 Remote Similarity NPC467188
0.6531 Remote Similarity NPC262898
0.6519 Remote Similarity NPC274981
0.6508 Remote Similarity NPC470205
0.6497 Remote Similarity NPC251391
0.648 Remote Similarity NPC79356
0.648 Remote Similarity NPC102592
0.6477 Remote Similarity NPC473878
0.6477 Remote Similarity NPC324091
0.6471 Remote Similarity NPC15573
0.6471 Remote Similarity NPC183662
0.6471 Remote Similarity NPC217372
0.645 Remote Similarity NPC64661
0.645 Remote Similarity NPC195704
0.645 Remote Similarity NPC98156
0.645 Remote Similarity NPC200397
0.645 Remote Similarity NPC292434
0.645 Remote Similarity NPC167200
0.645 Remote Similarity NPC14448
0.645 Remote Similarity NPC138596
0.6445 Remote Similarity NPC175150
0.6445 Remote Similarity NPC243633
0.6444 Remote Similarity NPC474492
0.6443 Remote Similarity NPC243716
0.6436 Remote Similarity NPC219336
0.6433 Remote Similarity NPC85443
0.6424 Remote Similarity NPC313823
0.642 Remote Similarity NPC123906
0.6409 Remote Similarity NPC470680
0.6409 Remote Similarity NPC100104
0.6404 Remote Similarity NPC312860
0.6398 Remote Similarity NPC288074
0.6395 Remote Similarity NPC169308
0.6395 Remote Similarity NPC74928
0.6395 Remote Similarity NPC59839
0.6395 Remote Similarity NPC209281
0.6395 Remote Similarity NPC97230
0.6395 Remote Similarity NPC3698
0.6395 Remote Similarity NPC129753
0.6395 Remote Similarity NPC244087
0.6395 Remote Similarity NPC77582
0.6395 Remote Similarity NPC286529
0.6395 Remote Similarity NPC48171
0.6395 Remote Similarity NPC12831
0.6395 Remote Similarity NPC302717
0.6395 Remote Similarity NPC205604
0.6387 Remote Similarity NPC477003
0.6382 Remote Similarity NPC237414
0.6381 Remote Similarity NPC168209
0.6364 Remote Similarity NPC100726
0.6355 Remote Similarity NPC82053
0.6354 Remote Similarity NPC474258
0.6349 Remote Similarity NPC11126
0.6348 Remote Similarity NPC70406
0.6348 Remote Similarity NPC217021
0.6348 Remote Similarity NPC470679
0.6344 Remote Similarity NPC302647
0.633 Remote Similarity NPC151635
0.6328 Remote Similarity NPC13432
0.6321 Remote Similarity NPC476527
0.6316 Remote Similarity NPC114310
0.6316 Remote Similarity NPC182940
0.631 Remote Similarity NPC161861
0.6302 Remote Similarity NPC228835
0.6302 Remote Similarity NPC110158
0.63 Remote Similarity NPC293917
0.6294 Remote Similarity NPC269886
0.6294 Remote Similarity NPC81802
0.6294 Remote Similarity NPC472210
0.6294 Remote Similarity NPC247735
0.6294 Remote Similarity NPC472295
0.6292 Remote Similarity NPC471655
0.6289 Remote Similarity NPC473946
0.6289 Remote Similarity NPC278434
0.6278 Remote Similarity NPC229055
0.6278 Remote Similarity NPC263455
0.6277 Remote Similarity NPC469529
0.627 Remote Similarity NPC41717
0.627 Remote Similarity NPC109447
0.6269 Remote Similarity NPC13456
0.6269 Remote Similarity NPC166209
0.6269 Remote Similarity NPC77241
0.6269 Remote Similarity NPC269203
0.6264 Remote Similarity NPC101130
0.6264 Remote Similarity NPC58268
0.6264 Remote Similarity NPC114033
0.6264 Remote Similarity NPC129412
0.6263 Remote Similarity NPC202812
0.6257 Remote Similarity NPC273532
0.625 Remote Similarity NPC470440
0.625 Remote Similarity NPC474389
0.625 Remote Similarity NPC159125
0.625 Remote Similarity NPC167400
0.6244 Remote Similarity NPC270918
0.6237 Remote Similarity NPC94752
0.6231 Remote Similarity NPC292361
0.623 Remote Similarity NPC91179
0.6225 Remote Similarity NPC88115
0.6221 Remote Similarity NPC65408
0.6219 Remote Similarity NPC268744
0.6219 Remote Similarity NPC474767
0.6219 Remote Similarity NPC201266
0.6219 Remote Similarity NPC475914
0.6219 Remote Similarity NPC220797
0.6219 Remote Similarity NPC474318
0.6219 Remote Similarity NPC153123
0.6218 Remote Similarity NPC21429
0.6212 Remote Similarity NPC474180
0.6212 Remote Similarity NPC188821
0.6212 Remote Similarity NPC88315
0.6207 Remote Similarity NPC106757
0.6205 Remote Similarity NPC17059
0.6201 Remote Similarity NPC313889
0.6193 Remote Similarity NPC476460
0.6193 Remote Similarity NPC159630
0.6193 Remote Similarity NPC230085
0.619 Remote Similarity NPC203468
0.619 Remote Similarity NPC149155
0.619 Remote Similarity NPC110500
0.6183 Remote Similarity NPC114637

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC474383 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
0.7459 Intermediate Similarity NPD2289 Phase 3
0.7459 Intermediate Similarity NPD2290 Phase 3
0.7018 Intermediate Similarity NPD9343 Clinical (unspecified phase)
0.6928 Remote Similarity NPD569 Clinical (unspecified phase)
0.6927 Remote Similarity NPD1575 Approved
0.6927 Remote Similarity NPD1573 Approved
0.6919 Remote Similarity NPD510 Phase 1
0.6902 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6798 Remote Similarity NPD1631 Approved
0.6753 Remote Similarity NPD7459 Phase 2
0.6738 Remote Similarity NPD1096 Discontinued
0.6629 Remote Similarity NPD1630 Approved
0.6575 Remote Similarity NPD1568 Clinical (unspecified phase)
0.6562 Remote Similarity NPD5686 Approved
0.6562 Remote Similarity NPD5685 Approved
0.6528 Remote Similarity NPD5592 Clinical (unspecified phase)
0.6497 Remote Similarity NPD180 Clinical (unspecified phase)
0.6488 Remote Similarity NPD272 Approved
0.6455 Remote Similarity NPD3178 Discontinued
0.6452 Remote Similarity NPD4736 Clinical (unspecified phase)
0.6436 Remote Similarity NPD1587 Approved
0.6436 Remote Similarity NPD4559 Clinical (unspecified phase)
0.6424 Remote Similarity NPD1031 Discontinued
0.6411 Remote Similarity NPD6578 Clinical (unspecified phase)
0.6406 Remote Similarity NPD5809 Phase 3
0.6402 Remote Similarity NPD1618 Phase 2
0.64 Remote Similarity NPD5017 Discontinued
0.6395 Remote Similarity NPD9599 Approved
0.6364 Remote Similarity NPD5322 Clinical (unspecified phase)
0.6343 Remote Similarity NPD175 Clinical (unspecified phase)
0.6341 Remote Similarity NPD3968 Approved
0.6338 Remote Similarity NPD6173 Approved
0.6333 Remote Similarity NPD276 Clinical (unspecified phase)
0.6324 Remote Similarity NPD3411 Phase 2
0.6324 Remote Similarity NPD3410 Approved
0.6321 Remote Similarity NPD5820 Clinical (unspecified phase)
0.6318 Remote Similarity NPD7903 Clinical (unspecified phase)
0.6318 Remote Similarity NPD7727 Phase 2
0.6318 Remote Similarity NPD7817 Phase 1
0.631 Remote Similarity NPD750 Phase 2
0.63 Remote Similarity NPD7621 Clinical (unspecified phase)
0.6278 Remote Similarity NPD2061 Approved
0.6277 Remote Similarity NPD1586 Approved
0.6274 Remote Similarity NPD6210 Phase 3
0.6269 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6264 Remote Similarity NPD5020 Approved
0.6263 Remote Similarity NPD3078 Approved
0.6263 Remote Similarity NPD3077 Approved
0.6263 Remote Similarity NPD3079 Approved
0.6263 Remote Similarity NPD2590 Clinical (unspecified phase)
0.6263 Remote Similarity NPD3076 Approved
0.625 Remote Similarity NPD9075 Approved
0.625 Remote Similarity NPD9074 Approved
0.6244 Remote Similarity NPD6665 Discontinued
0.6226 Remote Similarity NPD6369 Clinical (unspecified phase)
0.6225 Remote Similarity NPD8115 Approved
0.6225 Remote Similarity NPD8114 Approved
0.6225 Remote Similarity NPD6288 Clinical (unspecified phase)
0.6221 Remote Similarity NPD201 Phase 2
0.6221 Remote Similarity NPD200 Phase 2
0.6219 Remote Similarity NPD6249 Phase 2
0.6219 Remote Similarity NPD6248 Phase 2
0.6215 Remote Similarity NPD5001 Clinical (unspecified phase)
0.6196 Remote Similarity NPD9598 Discontinued
0.6195 Remote Similarity NPD3967 Approved
0.619 Remote Similarity NPD482 Approved
0.6184 Remote Similarity NPD4520 Approved
0.6181 Remote Similarity NPD7619 Phase 3
0.6181 Remote Similarity NPD7618 Phase 3
0.6162 Remote Similarity NPD5505 Discontinued
0.6162 Remote Similarity NPD7098 Clinical (unspecified phase)
0.6161 Remote Similarity NPD3353 Approved
0.6158 Remote Similarity NPD5333 Clinical (unspecified phase)
0.6154 Remote Similarity NPD7998 Clinical (unspecified phase)
0.615 Remote Similarity NPD1292 Clinical (unspecified phase)
0.6146 Remote Similarity NPD1643 Phase 3
0.6139 Remote Similarity NPD7308 Discontinued
0.6134 Remote Similarity NPD2091 Phase 2
0.6134 Remote Similarity NPD2096 Phase 2
0.6131 Remote Similarity NPD460 Discontinued
0.6121 Remote Similarity NPD1996 Discontinued
0.6114 Remote Similarity NPD107 Approved
0.6111 Remote Similarity NPD7913 Clinical (unspecified phase)
0.6111 Remote Similarity NPD7717 Approved
0.6111 Remote Similarity NPD7716 Approved
0.6106 Remote Similarity NPD5510 Approved
0.6105 Remote Similarity NPD4883 Approved
0.6103 Remote Similarity NPD4336 Clinical (unspecified phase)
0.6096 Remote Similarity NPD4174 Clinical (unspecified phase)
0.6092 Remote Similarity NPD2323 Clinical (unspecified phase)
0.6092 Remote Similarity NPD203 Clinical (unspecified phase)
0.6091 Remote Similarity NPD4334 Discontinued
0.6091 Remote Similarity NPD1284 Clinical (unspecified phase)
0.6089 Remote Similarity NPD4987 Clinical (unspecified phase)
0.6082 Remote Similarity NPD2094 Phase 2
0.6082 Remote Similarity NPD5728 Clinical (unspecified phase)
0.6082 Remote Similarity NPD2095 Phase 2
0.6082 Remote Similarity NPD9100 Approved
0.6082 Remote Similarity NPD2092 Phase 2
0.6077 Remote Similarity NPD5965 Clinical (unspecified phase)
0.6073 Remote Similarity NPD4385 Clinical (unspecified phase)
0.6073 Remote Similarity NPD749 Clinical (unspecified phase)
0.6071 Remote Similarity NPD3360 Clinical (unspecified phase)
0.6062 Remote Similarity NPD3927 Phase 2
0.6053 Remote Similarity NPD1037 Clinical (unspecified phase)
0.6053 Remote Similarity NPD4524 Discontinued
0.6048 Remote Similarity NPD7070 Clinical (unspecified phase)
0.6043 Remote Similarity NPD2915 Discontinued
0.6041 Remote Similarity NPD4948 Discontinued
0.6037 Remote Similarity NPD4811 Discontinued
0.6029 Remote Similarity NPD7704 Clinical (unspecified phase)
0.6019 Remote Similarity NPD2121 Clinical (unspecified phase)
0.601 Remote Similarity NPD7204 Clinical (unspecified phase)
0.6 Remote Similarity NPD4962 Approved
0.6 Remote Similarity NPD979 Approved
0.6 Remote Similarity NPD4315 Phase 2
0.6 Remote Similarity NPD3288 Approved
0.6 Remote Similarity NPD3319 Phase 1
0.6 Remote Similarity NPD3318 Approved
0.6 Remote Similarity NPD4963 Approved
0.6 Remote Similarity NPD9076 Clinical (unspecified phase)
0.6 Remote Similarity NPD3320 Approved
0.599 Remote Similarity NPD3947 Discontinued
0.599 Remote Similarity NPD4426 Clinical (unspecified phase)
0.5981 Remote Similarity NPD2510 Approved
0.5981 Remote Similarity NPD2509 Approved
0.598 Remote Similarity NPD3800 Clinical (unspecified phase)
0.5979 Remote Similarity NPD3989 Phase 3
0.5979 Remote Similarity NPD1291 Clinical (unspecified phase)
0.597 Remote Similarity NPD2004 Clinical (unspecified phase)
0.5969 Remote Similarity NPD7482 Phase 2
0.5969 Remote Similarity NPD7483 Phase 2
0.5969 Remote Similarity NPD7564 Discontinued
0.5964 Remote Similarity NPD5787 Discontinued
0.5962 Remote Similarity NPD7289 Clinical (unspecified phase)
0.5961 Remote Similarity NPD1952 Discontinued
0.5956 Remote Similarity NPD2603 Clinical (unspecified phase)
0.5955 Remote Similarity NPD9576 Discontinued
0.5953 Remote Similarity NPD1623 Approved
0.5951 Remote Similarity NPD4961 Approved
0.5951 Remote Similarity NPD9396 Approved
0.5951 Remote Similarity NPD9392 Approved
0.595 Remote Similarity NPD6180 Clinical (unspecified phase)
0.595 Remote Similarity NPD1658 Discontinued
0.595 Remote Similarity NPD3785 Clinical (unspecified phase)
0.5949 Remote Similarity NPD3990 Phase 3
0.5949 Remote Similarity NPD4011 Clinical (unspecified phase)
0.5946 Remote Similarity NPD4326 Phase 2
0.5942 Remote Similarity NPD5487 Phase 1
0.5936 Remote Similarity NPD6771 Discontinued
0.5935 Remote Similarity NPD3393 Approved
0.5935 Remote Similarity NPD3389 Approved
0.5935 Remote Similarity NPD3394 Approved
0.5933 Remote Similarity NPD6838 Clinical (unspecified phase)
0.5931 Remote Similarity NPD772 Phase 3
0.5931 Remote Similarity NPD2947 Clinical (unspecified phase)
0.5928 Remote Similarity NPD7887 Approved
0.5928 Remote Similarity NPD7888 Approved
0.5926 Remote Similarity NPD4643 Clinical (unspecified phase)
0.5924 Remote Similarity NPD5257 Clinical (unspecified phase)
0.592 Remote Similarity NPD4376 Phase 3
0.5918 Remote Similarity NPD5092 Clinical (unspecified phase)
0.5918 Remote Similarity NPD7401 Clinical (unspecified phase)
0.5916 Remote Similarity NPD5727 Clinical (unspecified phase)
0.5913 Remote Similarity NPD8169 Discontinued
0.5912 Remote Similarity NPD9271 Approved
0.5911 Remote Similarity NPD6226 Phase 3
0.5911 Remote Similarity NPD4848 Phase 1
0.5907 Remote Similarity NPD2367 Phase 2
0.5907 Remote Similarity NPD1591 Approved
0.5905 Remote Similarity NPD2442 Approved
0.5905 Remote Similarity NPD7232 Discontinued
0.5905 Remote Similarity NPD4960 Approved
0.5905 Remote Similarity NPD4959 Approved
0.5905 Remote Similarity NPD2443 Approved
0.5905 Remote Similarity NPD6376 Discontinued
0.5904 Remote Similarity NPD3583 Phase 2
0.5902 Remote Similarity NPD7049 Clinical (unspecified phase)
0.5899 Remote Similarity NPD4805 Approved
0.5897 Remote Similarity NPD2479 Phase 3
0.5897 Remote Similarity NPD5473 Discontinued
0.5897 Remote Similarity NPD2481 Approved
0.5897 Remote Similarity NPD7014 Clinical (unspecified phase)
0.5892 Remote Similarity NPD951 Approved
0.5891 Remote Similarity NPD1173 Approved
0.5891 Remote Similarity NPD5274 Clinical (unspecified phase)
0.5888 Remote Similarity NPD7971 Clinical (unspecified phase)
0.5888 Remote Similarity NPD721 Approved
0.5888 Remote Similarity NPD7970 Approved
0.5882 Remote Similarity NPD1174 Phase 2
0.5882 Remote Similarity NPD1781 Discontinued
0.5877 Remote Similarity NPD3856 Clinical (unspecified phase)
0.5867 Remote Similarity NPD4399 Phase 2
0.5866 Remote Similarity NPD4637 Clinical (unspecified phase)
0.5866 Remote Similarity NPD3717 Discontinued
0.5865 Remote Similarity NPD6176 Phase 1
0.5862 Remote Similarity NPD4602 Approved
0.586 Remote Similarity NPD820 Phase 3
0.5857 Remote Similarity NPD1506 Discontinued
0.5857 Remote Similarity NPD6328 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   11602770
ChEMBL   CHEMBL465779
ZINC  

Physicochemical Properties

Molecular Weight:  349.89
ALogP:  0.7686
MLogP:  1.68
XLogP:  1.096
# Rotatable Bonds:  5
Polar Surface Area:  71.33
# H-Bond Aceptor:  5
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  16

Download Data

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General Info & Identifiers & Properties  
Structure MOL file  
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Biological Activities  
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