Natural Product: NPC158551

Natural Product ID:  NPC158551
Common Name:   Limazepine C
IUPAC Name:   (6aS)-8-ethyl-4-hydroxy-3-methoxy-6a,7-dihydropyrrolo[2,1-c][1,4]benzodiazepin-11-one
Synonyms:   Limazepine C
Molecular Formula:   C15H16N2O3
Standard InCHIKey:  FLGURYUVNVBBFP-JTQLQIEISA-N
Standard InCHI:  InChI=1S/C15H16N2O3/c1-3-9-6-10-7-16-13-11(15(19)17(10)8-9)4-5-12(20-2)14(13)18/h4-5,7-8,10,18H,3,6H2,1-2H3/t10-/m0/s1
Canonical SMILES:  CCC1=CN2[C@@H](C1)C=Nc1c(C2=O)ccc(c1O)OC
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
NPO32521 micrococcus sp. Species Micrococcaceae Bacteria Indonesia PMID[19388705]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT19 Organism Escherichia coli Escherichia coli IZ = 10 mm 19161316
NPT16 Organism Staphylococcus aureus Staphylococcus aureus IZ = 18 mm 20196571

  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 NPC158551 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
0.9728 High Similarity NPC163829
0.8476 Intermediate Similarity NPC172222
0.8441 Intermediate Similarity NPC270301
0.8068 Intermediate Similarity NPC313327
0.7788 Intermediate Similarity NPC470481
0.7788 Intermediate Similarity NPC470482
0.772 Intermediate Similarity NPC98416
0.768 Intermediate Similarity NPC28368
0.7464 Intermediate Similarity NPC16249
0.7437 Intermediate Similarity NPC87391
0.7383 Intermediate Similarity NPC2905
0.7361 Intermediate Similarity NPC182853
0.7339 Intermediate Similarity NPC76478
0.733 Intermediate Similarity NPC135006
0.7323 Intermediate Similarity NPC197335
0.7286 Intermediate Similarity NPC314659
0.7282 Intermediate Similarity NPC161804
0.726 Intermediate Similarity NPC7560
0.7256 Intermediate Similarity NPC114468
0.7222 Intermediate Similarity NPC148391
0.7202 Intermediate Similarity NPC134702
0.7189 Intermediate Similarity NPC471531
0.7182 Intermediate Similarity NPC118189
0.7163 Intermediate Similarity NPC295479
0.7163 Intermediate Similarity NPC220241
0.7158 Intermediate Similarity NPC470708
0.7156 Intermediate Similarity NPC473460
0.7128 Intermediate Similarity NPC469540
0.7128 Intermediate Similarity NPC469539
0.7123 Intermediate Similarity NPC473422
0.7122 Intermediate Similarity NPC92803
0.7115 Intermediate Similarity NPC316282
0.7103 Intermediate Similarity NPC100573
0.7103 Intermediate Similarity NPC207873
0.7098 Intermediate Similarity NPC470480
0.7078 Intermediate Similarity NPC126556
0.7056 Intermediate Similarity NPC212123
0.7054 Intermediate Similarity NPC285254
0.7024 Intermediate Similarity NPC18890
0.7019 Intermediate Similarity NPC198401
0.701 Intermediate Similarity NPC262725
0.7005 Intermediate Similarity NPC204970
0.7 Intermediate Similarity NPC71124
0.6996 Remote Similarity NPC250960
0.6996 Remote Similarity NPC71539
0.6991 Remote Similarity NPC471561
0.699 Remote Similarity NPC174629
0.6971 Remote Similarity NPC254957
0.6963 Remote Similarity NPC14339
0.6963 Remote Similarity NPC268077
0.6963 Remote Similarity NPC119669
0.6947 Remote Similarity NPC13249
0.694 Remote Similarity NPC41501
0.6939 Remote Similarity NPC299582
0.6935 Remote Similarity NPC138438
0.6935 Remote Similarity NPC908
0.6931 Remote Similarity NPC39822
0.6931 Remote Similarity NPC5167
0.6927 Remote Similarity NPC471532
0.6903 Remote Similarity NPC266994
0.6895 Remote Similarity NPC119722
0.6887 Remote Similarity NPC5374
0.6881 Remote Similarity NPC287152
0.6864 Remote Similarity NPC268223
0.6858 Remote Similarity NPC122886
0.6844 Remote Similarity NPC148124
0.6842 Remote Similarity NPC74216
0.6842 Remote Similarity NPC246381
0.684 Remote Similarity NPC17677
0.6837 Remote Similarity NPC207971
0.6832 Remote Similarity NPC9475
0.6818 Remote Similarity NPC305542
0.6816 Remote Similarity NPC195120
0.6816 Remote Similarity NPC87560
0.6806 Remote Similarity NPC153644
0.6804 Remote Similarity NPC269449
0.68 Remote Similarity NPC99724
0.6796 Remote Similarity NPC138083
0.6792 Remote Similarity NPC24228
0.6789 Remote Similarity NPC90185
0.6787 Remote Similarity NPC30749
0.6781 Remote Similarity NPC314702
0.6766 Remote Similarity NPC73280
0.6765 Remote Similarity NPC85613
0.6765 Remote Similarity NPC32064
0.6759 Remote Similarity NPC41216
0.6748 Remote Similarity NPC132385
0.6742 Remote Similarity NPC10732
0.6741 Remote Similarity NPC173080
0.6736 Remote Similarity NPC270515
0.6727 Remote Similarity NPC474366
0.6725 Remote Similarity NPC248903
0.6714 Remote Similarity NPC28510
0.67 Remote Similarity NPC35345
0.6683 Remote Similarity NPC276120
0.6682 Remote Similarity NPC206109
0.6682 Remote Similarity NPC114039
0.6681 Remote Similarity NPC26928
0.6681 Remote Similarity NPC157983
0.6681 Remote Similarity NPC118154
0.6667 Remote Similarity NPC116178
0.6667 Remote Similarity NPC471489
0.6667 Remote Similarity NPC291173
0.6667 Remote Similarity NPC174122
0.6667 Remote Similarity NPC64140
0.6667 Remote Similarity NPC170333
0.6667 Remote Similarity NPC470821
0.6652 Remote Similarity NPC128476
0.6638 Remote Similarity NPC19175
0.6637 Remote Similarity NPC217903
0.6636 Remote Similarity NPC272706
0.6635 Remote Similarity NPC1820
0.6634 Remote Similarity NPC20395
0.662 Remote Similarity NPC127178
0.6619 Remote Similarity NPC162694
0.6619 Remote Similarity NPC234069
0.6618 Remote Similarity NPC8467
0.6605 Remote Similarity NPC112937
0.6602 Remote Similarity NPC222524
0.66 Remote Similarity NPC153631
0.6597 Remote Similarity NPC477395
0.6596 Remote Similarity NPC231572
0.6591 Remote Similarity NPC198160
0.6578 Remote Similarity NPC122553
0.6576 Remote Similarity NPC308885
0.6576 Remote Similarity NPC255550
0.6575 Remote Similarity NPC210256
0.6575 Remote Similarity NPC475147
0.6573 Remote Similarity NPC203972
0.6569 Remote Similarity NPC160100
0.6569 Remote Similarity NPC164608
0.6566 Remote Similarity NPC301163
0.6562 Remote Similarity NPC321166
0.6555 Remote Similarity NPC473007
0.6547 Remote Similarity NPC218303
0.6541 Remote Similarity NPC93882
0.6541 Remote Similarity NPC130595
0.654 Remote Similarity NPC477186
0.6535 Remote Similarity NPC10653
0.6535 Remote Similarity NPC318525
0.6533 Remote Similarity NPC93653
0.6533 Remote Similarity NPC298449
0.6533 Remote Similarity NPC176113
0.6531 Remote Similarity NPC185172
0.6528 Remote Similarity NPC100863
0.6524 Remote Similarity NPC116007
0.6518 Remote Similarity NPC159815
0.6516 Remote Similarity NPC308943
0.6509 Remote Similarity NPC29531
0.6505 Remote Similarity NPC285078
0.6505 Remote Similarity NPC6854
0.6505 Remote Similarity NPC313737
0.6502 Remote Similarity NPC134637
0.65 Remote Similarity NPC257763
0.6497 Remote Similarity NPC133011
0.6497 Remote Similarity NPC82285
0.6495 Remote Similarity NPC94499
0.6484 Remote Similarity NPC474077
0.6483 Remote Similarity NPC253675
0.6471 Remote Similarity NPC218530
0.6463 Remote Similarity NPC303374
0.6462 Remote Similarity NPC124626
0.6462 Remote Similarity NPC169387
0.6462 Remote Similarity NPC241392
0.6462 Remote Similarity NPC477259
0.646 Remote Similarity NPC146976
0.6457 Remote Similarity NPC475133
0.6456 Remote Similarity NPC67978
0.6456 Remote Similarity NPC303581
0.645 Remote Similarity NPC235628
0.6449 Remote Similarity NPC473004
0.6447 Remote Similarity NPC82056
0.6445 Remote Similarity NPC150308
0.6444 Remote Similarity NPC316981
0.6443 Remote Similarity NPC315829
0.6442 Remote Similarity NPC283810
0.6441 Remote Similarity NPC478075
0.6435 Remote Similarity NPC329830
0.6432 Remote Similarity NPC473008
0.6432 Remote Similarity NPC470001
0.6432 Remote Similarity NPC470002
0.6429 Remote Similarity NPC470088
0.6425 Remote Similarity NPC256935
0.6422 Remote Similarity NPC207239
0.6419 Remote Similarity NPC470485
0.6417 Remote Similarity NPC266425
0.6416 Remote Similarity NPC236668
0.6413 Remote Similarity NPC329567
0.6413 Remote Similarity NPC205926
0.6413 Remote Similarity NPC330683
0.6411 Remote Similarity NPC73555
0.641 Remote Similarity NPC321505
0.641 Remote Similarity NPC179825
0.641 Remote Similarity NPC191376
0.6409 Remote Similarity NPC15987
0.6404 Remote Similarity NPC476569
0.6402 Remote Similarity NPC43218
0.6396 Remote Similarity NPC478189
0.6396 Remote Similarity NPC477161
0.6394 Remote Similarity NPC308267

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC158551 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
0.8058 Intermediate Similarity NPD7559 Phase 2
0.7802 Intermediate Similarity NPD824 Approved
0.7327 Intermediate Similarity NPD6377 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD956 Clinical (unspecified phase)
0.7248 Intermediate Similarity NPD2899 Discontinued
0.7216 Intermediate Similarity NPD2821 Approved
0.7189 Intermediate Similarity NPD5025 Approved
0.7083 Intermediate Similarity NPD683 Approved
0.7039 Intermediate Similarity NPD5525 Clinical (unspecified phase)
0.7037 Intermediate Similarity NPD4997 Clinical (unspecified phase)
0.7028 Intermediate Similarity NPD6795 Clinical (unspecified phase)
0.7024 Intermediate Similarity NPD6608 Clinical (unspecified phase)
0.7016 Intermediate Similarity NPD1337 Clinical (unspecified phase)
0.6934 Remote Similarity NPD7255 Clinical (unspecified phase)
0.692 Remote Similarity NPD4049 Phase 2
0.6919 Remote Similarity NPD5071 Phase 2
0.6895 Remote Similarity NPD7225 Discontinued
0.6888 Remote Similarity NPD8091 Phase 3
0.6881 Remote Similarity NPD5645 Phase 3
0.6869 Remote Similarity NPD7071 Clinical (unspecified phase)
0.6859 Remote Similarity NPD1670 Discontinued
0.6812 Remote Similarity NPD4515 Suspended
0.681 Remote Similarity NPD3631 Phase 3
0.6806 Remote Similarity NPD5102 Clinical (unspecified phase)
0.6759 Remote Similarity NPD3802 Phase 3
0.6753 Remote Similarity NPD2592 Discontinued
0.675 Remote Similarity NPD5183 Approved
0.675 Remote Similarity NPD5186 Approved
0.675 Remote Similarity NPD1293 Approved
0.6731 Remote Similarity NPD4084 Clinical (unspecified phase)
0.67 Remote Similarity NPD2822 Clinical (unspecified phase)
0.6699 Remote Similarity NPD7132 Clinical (unspecified phase)
0.6699 Remote Similarity NPD7291 Discontinued
0.6698 Remote Similarity NPD3473 Clinical (unspecified phase)
0.6681 Remote Similarity NPD7858 Clinical (unspecified phase)
0.6667 Remote Similarity NPD743 Approved
0.6667 Remote Similarity NPD7263 Phase 2
0.6651 Remote Similarity NPD4539 Phase 1
0.6638 Remote Similarity NPD3442 Approved
0.6638 Remote Similarity NPD3441 Approved
0.6621 Remote Similarity NPD7607 Clinical (unspecified phase)
0.662 Remote Similarity NPD4413 Clinical (unspecified phase)
0.6606 Remote Similarity NPD3592 Approved
0.6606 Remote Similarity NPD3591 Approved
0.6581 Remote Similarity NPD6625 Approved
0.6578 Remote Similarity NPD8149 Discontinued
0.6576 Remote Similarity NPD3145 Approved
0.6576 Remote Similarity NPD3144 Approved
0.6569 Remote Similarity NPD5966 Clinical (unspecified phase)
0.6541 Remote Similarity NPD2674 Phase 3
0.6526 Remote Similarity NPD3633 Approved
0.6526 Remote Similarity NPD3634 Approved
0.652 Remote Similarity NPD1220 Phase 1
0.6513 Remote Similarity NPD6662 Clinical (unspecified phase)
0.6509 Remote Similarity NPD2843 Phase 2
0.6509 Remote Similarity NPD2845 Phase 2
0.6507 Remote Similarity NPD7280 Phase 3
0.6507 Remote Similarity NPD7281 Phase 3
0.6505 Remote Similarity NPD1221 Approved
0.6502 Remote Similarity NPD5914 Approved
0.6502 Remote Similarity NPD5860 Discontinued
0.65 Remote Similarity NPD4465 Phase 2
0.65 Remote Similarity NPD4467 Phase 2
0.65 Remote Similarity NPD4456 Clinical (unspecified phase)
0.649 Remote Similarity NPD4926 Clinical (unspecified phase)
0.649 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6486 Remote Similarity NPD4082 Approved
0.6484 Remote Similarity NPD3106 Clinical (unspecified phase)
0.6473 Remote Similarity NPD4493 Discontinued
0.6473 Remote Similarity NPD4206 Approved
0.6471 Remote Similarity NPD4083 Discontinued
0.6453 Remote Similarity NPD2680 Approved
0.6453 Remote Similarity NPD6199 Discontinued
0.6453 Remote Similarity NPD2681 Approved
0.645 Remote Similarity NPD5978 Approved
0.645 Remote Similarity NPD5977 Approved
0.6445 Remote Similarity NPD3153 Approved
0.6445 Remote Similarity NPD3154 Approved
0.6442 Remote Similarity NPD6297 Approved
0.6441 Remote Similarity NPD4596 Phase 1
0.6429 Remote Similarity NPD3893 Discontinued
0.6425 Remote Similarity NPD3793 Phase 3
0.6414 Remote Similarity NPD5617 Suspended
0.6413 Remote Similarity NPD2907 Approved
0.6413 Remote Similarity NPD3472 Approved
0.6413 Remote Similarity NPD4022 Approved
0.6413 Remote Similarity NPD2906 Approved
0.6408 Remote Similarity NPD5602 Clinical (unspecified phase)
0.6406 Remote Similarity NPD4979 Clinical (unspecified phase)
0.6398 Remote Similarity NPD6618 Phase 2
0.6396 Remote Similarity NPD7174 Clinical (unspecified phase)
0.6394 Remote Similarity NPD2325 Approved
0.6385 Remote Similarity NPD3349 Phase 2
0.6382 Remote Similarity NPD6385 Approved
0.6382 Remote Similarity NPD7109 Clinical (unspecified phase)
0.6382 Remote Similarity NPD7110 Phase 1
0.6382 Remote Similarity NPD6386 Approved
0.6377 Remote Similarity NPD5603 Clinical (unspecified phase)
0.6373 Remote Similarity NPD2247 Approved
0.6373 Remote Similarity NPD2249 Approved
0.6372 Remote Similarity NPD5937 Approved
0.6372 Remote Similarity NPD4492 Approved
0.6372 Remote Similarity NPD4494 Approved
0.6372 Remote Similarity NPD3888 Discontinued
0.6371 Remote Similarity NPD4373 Phase 2
0.6359 Remote Similarity NPD2898 Approved
0.6356 Remote Similarity NPD3372 Discontinued
0.6351 Remote Similarity NPD7546 Discontinued
0.6351 Remote Similarity NPD3298 Approved
0.6347 Remote Similarity NPD6874 Approved
0.6347 Remote Similarity NPD7810 Phase 3
0.6347 Remote Similarity NPD7811 Phase 3
0.6346 Remote Similarity NPD5312 Approved
0.6346 Remote Similarity NPD5313 Approved
0.6345 Remote Similarity NPD3639 Approved
0.6345 Remote Similarity NPD3640 Phase 3
0.6345 Remote Similarity NPD3641 Approved
0.6344 Remote Similarity NPD4455 Discontinued
0.6343 Remote Similarity NPD4466 Phase 1
0.6332 Remote Similarity NPD3684 Discontinued
0.6332 Remote Similarity NPD6875 Approved
0.6332 Remote Similarity NPD6876 Approved
0.6332 Remote Similarity NPD3949 Clinical (unspecified phase)
0.633 Remote Similarity NPD5515 Phase 2
0.6325 Remote Similarity NPD5640 Discontinued
0.6324 Remote Similarity NPD9494 Approved
0.6322 Remote Similarity NPD6716 Phase 1
0.6321 Remote Similarity NPD6851 Approved
0.6321 Remote Similarity NPD6853 Approved
0.632 Remote Similarity NPD3437 Discontinued
0.6313 Remote Similarity NPD950 Clinical (unspecified phase)
0.6308 Remote Similarity NPD4157 Discontinued
0.6308 Remote Similarity NPD1898 Discontinued
0.6308 Remote Similarity NPD2792 Approved
0.6305 Remote Similarity NPD6533 Clinical (unspecified phase)
0.6305 Remote Similarity NPD1309 Phase 2
0.6305 Remote Similarity NPD1307 Phase 2
0.63 Remote Similarity NPD2672 Discontinued
0.6294 Remote Similarity NPD9509 Clinical (unspecified phase)
0.6288 Remote Similarity NPD5561 Approved
0.6288 Remote Similarity NPD5562 Approved
0.628 Remote Similarity NPD6894 Phase 1
0.6279 Remote Similarity NPD5896 Clinical (unspecified phase)
0.6277 Remote Similarity NPD5519 Discontinued
0.6277 Remote Similarity NPD5496 Approved
0.6276 Remote Similarity NPD4357 Discontinued
0.6274 Remote Similarity NPD3534 Clinical (unspecified phase)
0.6274 Remote Similarity NPD5917 Clinical (unspecified phase)
0.6269 Remote Similarity NPD3655 Clinical (unspecified phase)
0.6268 Remote Similarity NPD3965 Phase 1
0.6267 Remote Similarity NPD6046 Clinical (unspecified phase)
0.6266 Remote Similarity NPD6997 Phase 2
0.6263 Remote Similarity NPD711 Discontinued
0.6262 Remote Similarity NPD4606 Clinical (unspecified phase)
0.6261 Remote Similarity NPD7316 Discontinued
0.6261 Remote Similarity NPD3940 Clinical (unspecified phase)
0.6256 Remote Similarity NPD4605 Approved
0.6256 Remote Similarity NPD1945 Phase 1
0.6256 Remote Similarity NPD4604 Approved
0.6255 Remote Similarity NPD7186 Phase 3
0.625 Remote Similarity NPD5641 Discontinued
0.625 Remote Similarity NPD5433 Clinical (unspecified phase)
0.6245 Remote Similarity NPD5022 Discontinued
0.6245 Remote Similarity NPD4952 Phase 3
0.6244 Remote Similarity NPD7201 Clinical (unspecified phase)
0.624 Remote Similarity NPD7560 Approved
0.624 Remote Similarity NPD7886 Phase 2
0.624 Remote Similarity NPD7885 Phase 2
0.624 Remote Similarity NPD7025 Clinical (unspecified phase)
0.6239 Remote Similarity NPD3912 Discontinued
0.6239 Remote Similarity NPD7278 Phase 2
0.6239 Remote Similarity NPD7279 Phase 2
0.6224 Remote Similarity NPD7048 Phase 3
0.6222 Remote Similarity NPD6296 Discontinued
0.6218 Remote Similarity NPD1505 Phase 2
0.6218 Remote Similarity NPD6962 Phase 2
0.6217 Remote Similarity NPD6744 Clinical (unspecified phase)
0.6214 Remote Similarity NPD6790 Phase 1
0.621 Remote Similarity NPD7667 Clinical (unspecified phase)
0.6209 Remote Similarity NPD6654 Clinical (unspecified phase)
0.6207 Remote Similarity NPD5967 Approved
0.6207 Remote Similarity NPD6063 Approved
0.6203 Remote Similarity NPD7710 Clinical (unspecified phase)
0.6194 Remote Similarity NPD7013 Phase 3
0.6194 Remote Similarity NPD7012 Phase 3
0.6192 Remote Similarity NPD7031 Phase 1
0.6189 Remote Similarity NPD1483 Discontinued
0.6184 Remote Similarity NPD4166 Phase 2
0.6183 Remote Similarity NPD3006 Discontinued
0.6182 Remote Similarity NPD5564 Approved
0.618 Remote Similarity NPD3783 Clinical (unspecified phase)
0.6175 Remote Similarity NPD6656 Clinical (unspecified phase)
0.6175 Remote Similarity NPD5871 Discontinued
0.6171 Remote Similarity NPD5457 Discontinued
0.6171 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6167 Remote Similarity NPD7922 Phase 1
0.6167 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6164 Remote Similarity NPD4429 Discontinued
0.6161 Remote Similarity NPD7064 Clinical (unspecified phase)
0.6161 Remote Similarity NPD7597 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   42639506
ChEMBL   CHEMBL555727
ZINC  

Physicochemical Properties

Molecular Weight:  272.12
ALogP:  -1.2177
MLogP:  2.56
XLogP:  1.071
# Rotatable Bonds:  5
Polar Surface Area:  62.13
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  20

Download Data

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