Natural Product: NPC314659

Natural Product ID:  NPC314659
Common Name:   Usabamycin A
IUPAC Name:   (6aS,8E)-4-methoxy-8-propylidene-6,6a,7,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one
Synonyms:   Usabamycin A
Molecular Formula:   C16H20N2O2
Standard InCHIKey:  VRTIPIUNHQTBEU-JVOXIWMLSA-N
Standard InCHI:  InChI=1S/C16H20N2O2/c1-3-5-11-8-12-9-17-15-13(16(19)18(12)10-11)6-4-7-14(15)20-2/h4-7,12,17H,3,8-10H2,1-2H3/b11-5+/t12-/m0/s1
Canonical SMILES:  CC/C=C/1C[C@@H]2N(C1)C(=O)c1c(NC2)c(OC)ccc1
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
NPO31830 Streptomyces nps853 Species Streptomycetaceae Bacteria StreptomeDB*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT165 Cell Line HeLa Homo sapiens IC50 = 106600 nM 22001031
NPT291 Individual Protein Serotonin 2b (5-HT2b) receptor Homo sapiens IC50 = 12400 nM 22001031
NPT291 Individual Protein Serotonin 2b (5-HT2b) receptor Homo sapiens Ki = 7890 nM 22001031

  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 NPC314659 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
0.9938 High Similarity NPC197335
0.9464 High Similarity NPC87391
0.8563 High Similarity NPC270301
0.8251 Intermediate Similarity NPC198401
0.8235 Intermediate Similarity NPC257763
0.8065 Intermediate Similarity NPC316282
0.7803 Intermediate Similarity NPC301163
0.7747 Intermediate Similarity NPC472163
0.7657 Intermediate Similarity NPC93653
0.7583 Intermediate Similarity NPC314702
0.7552 Intermediate Similarity NPC112937
0.7513 Intermediate Similarity NPC478075
0.75 Intermediate Similarity NPC316104
0.75 Intermediate Similarity NPC162417
0.75 Intermediate Similarity NPC163829
0.7452 Intermediate Similarity NPC257851
0.7418 Intermediate Similarity NPC73280
0.7286 Intermediate Similarity NPC158551
0.7282 Intermediate Similarity NPC100863
0.7273 Intermediate Similarity NPC122886
0.7219 Intermediate Similarity NPC5167
0.7219 Intermediate Similarity NPC85613
0.7219 Intermediate Similarity NPC283810
0.7211 Intermediate Similarity NPC262725
0.7174 Intermediate Similarity NPC471648
0.715 Intermediate Similarity NPC92803
0.7128 Intermediate Similarity NPC230313
0.7128 Intermediate Similarity NPC243626
0.7114 Intermediate Similarity NPC246140
0.7114 Intermediate Similarity NPC195787
0.7104 Intermediate Similarity NPC471652
0.7095 Intermediate Similarity NPC470708
0.709 Intermediate Similarity NPC28368
0.709 Intermediate Similarity NPC116096
0.7083 Intermediate Similarity NPC266425
0.7068 Intermediate Similarity NPC473007
0.7049 Intermediate Similarity NPC299582
0.7047 Intermediate Similarity NPC18890
0.7044 Intermediate Similarity NPC329567
0.7044 Intermediate Similarity NPC330683
0.7041 Intermediate Similarity NPC173295
0.703 Intermediate Similarity NPC477161
0.702 Intermediate Similarity NPC71124
0.701 Intermediate Similarity NPC45389
0.7006 Intermediate Similarity NPC241392
0.699 Remote Similarity NPC470482
0.699 Remote Similarity NPC470481
0.6974 Remote Similarity NPC22476
0.6963 Remote Similarity NPC157931
0.6947 Remote Similarity NPC70092
0.6935 Remote Similarity NPC265642
0.6935 Remote Similarity NPC132874
0.6935 Remote Similarity NPC138615
0.6935 Remote Similarity NPC218733
0.6931 Remote Similarity NPC41216
0.6923 Remote Similarity NPC473008
0.6904 Remote Similarity NPC254957
0.69 Remote Similarity NPC5374
0.6897 Remote Similarity NPC268077
0.6878 Remote Similarity NPC285192
0.6872 Remote Similarity NPC288987
0.6857 Remote Similarity NPC313327
0.6853 Remote Similarity NPC473004
0.6847 Remote Similarity NPC207971
0.6845 Remote Similarity NPC477160
0.684 Remote Similarity NPC323969
0.6837 Remote Similarity NPC5630
0.6829 Remote Similarity NPC16249
0.6825 Remote Similarity NPC77777
0.6821 Remote Similarity NPC21425
0.6814 Remote Similarity NPC475147
0.6806 Remote Similarity NPC287152
0.6806 Remote Similarity NPC478078
0.6789 Remote Similarity NPC8467
0.6782 Remote Similarity NPC138830
0.6777 Remote Similarity NPC126556
0.6748 Remote Similarity NPC212123
0.6745 Remote Similarity NPC248601
0.6743 Remote Similarity NPC471164
0.6742 Remote Similarity NPC146370
0.6731 Remote Similarity NPC471304
0.6727 Remote Similarity NPC172222
0.6721 Remote Similarity NPC471649
0.6716 Remote Similarity NPC1464
0.6702 Remote Similarity NPC33507
0.6698 Remote Similarity NPC471197
0.6697 Remote Similarity NPC471762
0.6684 Remote Similarity NPC166169
0.6683 Remote Similarity NPC475133
0.6667 Remote Similarity NPC302235
0.6667 Remote Similarity NPC174629
0.6667 Remote Similarity NPC471198
0.6667 Remote Similarity NPC474059
0.6667 Remote Similarity NPC87560
0.6667 Remote Similarity NPC154922
0.6667 Remote Similarity NPC469732
0.6667 Remote Similarity NPC43218
0.6667 Remote Similarity NPC195120
0.6652 Remote Similarity NPC329631
0.6651 Remote Similarity NPC474366
0.665 Remote Similarity NPC470485
0.6648 Remote Similarity NPC43477
0.6636 Remote Similarity NPC475609
0.6636 Remote Similarity NPC115588
0.6635 Remote Similarity NPC100573
0.6635 Remote Similarity NPC268223
0.6635 Remote Similarity NPC207873
0.6635 Remote Similarity NPC30749
0.6634 Remote Similarity NPC41488
0.6634 Remote Similarity NPC161804
0.6633 Remote Similarity NPC1820
0.6631 Remote Similarity NPC189116
0.663 Remote Similarity NPC144691
0.6622 Remote Similarity NPC148889
0.6622 Remote Similarity NPC39370
0.6621 Remote Similarity NPC194740
0.6621 Remote Similarity NPC66777
0.6621 Remote Similarity NPC311906
0.6619 Remote Similarity NPC187501
0.6614 Remote Similarity NPC471651
0.6612 Remote Similarity NPC119669
0.6606 Remote Similarity NPC139373
0.6606 Remote Similarity NPC473186
0.6606 Remote Similarity NPC196718
0.6593 Remote Similarity NPC314223
0.6591 Remote Similarity NPC223242
0.659 Remote Similarity NPC253476
0.6589 Remote Similarity NPC96321
0.6588 Remote Similarity NPC119722
0.6575 Remote Similarity NPC242000
0.6575 Remote Similarity NPC324081
0.6573 Remote Similarity NPC308197
0.657 Remote Similarity NPC87714
0.657 Remote Similarity NPC473422
0.6568 Remote Similarity NPC250476
0.6561 Remote Similarity NPC279527
0.6561 Remote Similarity NPC214960
0.6558 Remote Similarity NPC222046
0.6557 Remote Similarity NPC39500
0.6556 Remote Similarity NPC471647
0.6556 Remote Similarity NPC9373
0.6556 Remote Similarity NPC471646
0.655 Remote Similarity NPC470483
0.655 Remote Similarity NPC203628
0.6548 Remote Similarity NPC322621
0.6542 Remote Similarity NPC195636
0.6537 Remote Similarity NPC67904
0.6534 Remote Similarity NPC319645
0.6532 Remote Similarity NPC102593
0.6532 Remote Similarity NPC49547
0.6528 Remote Similarity NPC225279
0.6528 Remote Similarity NPC157983
0.6528 Remote Similarity NPC118154
0.6528 Remote Similarity NPC472099
0.6526 Remote Similarity NPC66191
0.6526 Remote Similarity NPC148391
0.6526 Remote Similarity NPC316297
0.6526 Remote Similarity NPC314817
0.6522 Remote Similarity NPC473460
0.652 Remote Similarity NPC113455
0.6517 Remote Similarity NPC204970
0.6513 Remote Similarity NPC98416
0.6512 Remote Similarity NPC303658
0.6509 Remote Similarity NPC305542
0.6503 Remote Similarity NPC469540
0.6503 Remote Similarity NPC469539
0.65 Remote Similarity NPC473569
0.6498 Remote Similarity NPC76478
0.6493 Remote Similarity NPC269449
0.6491 Remote Similarity NPC122235
0.649 Remote Similarity NPC470484
0.6479 Remote Similarity NPC114468
0.6477 Remote Similarity NPC122553
0.6471 Remote Similarity NPC470021
0.6468 Remote Similarity NPC144452
0.6462 Remote Similarity NPC218303
0.646 Remote Similarity NPC301501
0.6459 Remote Similarity NPC225400
0.6452 Remote Similarity NPC476069
0.645 Remote Similarity NPC226794
0.6449 Remote Similarity NPC50562
0.6449 Remote Similarity NPC176113
0.6449 Remote Similarity NPC2905
0.6448 Remote Similarity NPC214239
0.6447 Remote Similarity NPC99723
0.6441 Remote Similarity NPC471316
0.6435 Remote Similarity NPC134702
0.6435 Remote Similarity NPC182853
0.6435 Remote Similarity NPC120239
0.6435 Remote Similarity NPC184408
0.6432 Remote Similarity NPC10732
0.6432 Remote Similarity NPC116007
0.6429 Remote Similarity NPC308943
0.6429 Remote Similarity NPC321428
0.6429 Remote Similarity NPC470786
0.6429 Remote Similarity NPC472538
0.6429 Remote Similarity NPC222561
0.6429 Remote Similarity NPC471155
0.6425 Remote Similarity NPC177261
0.6422 Remote Similarity NPC472540

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC314659 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
0.8023 Intermediate Similarity NPD5603 Clinical (unspecified phase)
0.7923 Intermediate Similarity NPD4515 Suspended
0.7742 Intermediate Similarity NPD5896 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD5183 Approved
0.7697 Intermediate Similarity NPD5186 Approved
0.7596 Intermediate Similarity NPD6654 Clinical (unspecified phase)
0.7588 Intermediate Similarity NPD4492 Approved
0.7588 Intermediate Similarity NPD4494 Approved
0.7542 Intermediate Similarity NPD2681 Approved
0.7542 Intermediate Similarity NPD2680 Approved
0.75 Intermediate Similarity NPD5294 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD3888 Discontinued
0.7487 Intermediate Similarity NPD7071 Clinical (unspecified phase)
0.7475 Intermediate Similarity NPD4022 Approved
0.7475 Intermediate Similarity NPD3472 Approved
0.7475 Intermediate Similarity NPD4082 Approved
0.7461 Intermediate Similarity NPD5071 Phase 2
0.7436 Intermediate Similarity NPD6238 Discontinued
0.74 Intermediate Similarity NPD3372 Discontinued
0.74 Intermediate Similarity NPD3893 Discontinued
0.7398 Intermediate Similarity NPD6795 Clinical (unspecified phase)
0.7376 Intermediate Similarity NPD4455 Discontinued
0.7363 Intermediate Similarity NPD4493 Discontinued
0.7353 Intermediate Similarity NPD3940 Clinical (unspecified phase)
0.734 Intermediate Similarity NPD6021 Clinical (unspecified phase)
0.733 Intermediate Similarity NPD7858 Clinical (unspecified phase)
0.7323 Intermediate Similarity NPD4465 Phase 2
0.7323 Intermediate Similarity NPD4467 Phase 2
0.7288 Intermediate Similarity NPD4205 Phase 3
0.7253 Intermediate Similarity NPD2249 Approved
0.7253 Intermediate Similarity NPD2247 Approved
0.725 Intermediate Similarity NPD4596 Phase 1
0.7247 Intermediate Similarity NPD1769 Discontinued
0.7246 Intermediate Similarity NPD5433 Clinical (unspecified phase)
0.7236 Intermediate Similarity NPD4456 Clinical (unspecified phase)
0.7219 Intermediate Similarity NPD6293 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD5102 Clinical (unspecified phase)
0.7143 Intermediate Similarity NPD5860 Discontinued
0.71 Intermediate Similarity NPD6478 Clinical (unspecified phase)
0.7085 Intermediate Similarity NPD6321 Discontinued
0.7083 Intermediate Similarity NPD4084 Clinical (unspecified phase)
0.7081 Intermediate Similarity NPD3783 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD5143 Clinical (unspecified phase)
0.7065 Intermediate Similarity NPD7126 Discontinued
0.7059 Intermediate Similarity NPD743 Approved
0.7056 Intermediate Similarity NPD5515 Phase 2
0.7044 Intermediate Similarity NPD2906 Approved
0.7044 Intermediate Similarity NPD2907 Approved
0.7026 Intermediate Similarity NPD3479 Discontinued
0.7017 Intermediate Similarity NPD2842 Clinical (unspecified phase)
0.7005 Intermediate Similarity NPD6720 Clinical (unspecified phase)
0.6986 Remote Similarity NPD4429 Discontinued
0.6978 Remote Similarity NPD1012 Discontinued
0.6977 Remote Similarity NPD6199 Discontinued
0.6968 Remote Similarity NPD6645 Clinical (unspecified phase)
0.6966 Remote Similarity NPD1670 Discontinued
0.6959 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6935 Remote Similarity NPD5847 Phase 1
0.6919 Remote Similarity NPD3437 Discontinued
0.6908 Remote Similarity NPD7225 Discontinued
0.6906 Remote Similarity NPD4201 Clinical (unspecified phase)
0.6904 Remote Similarity NPD4539 Phase 1
0.6902 Remote Similarity NPD6533 Clinical (unspecified phase)
0.6895 Remote Similarity NPD795 Clinical (unspecified phase)
0.6893 Remote Similarity NPD1802 Approved
0.6893 Remote Similarity NPD1801 Approved
0.6891 Remote Similarity NPD6618 Phase 2
0.6872 Remote Similarity NPD5188 Clinical (unspecified phase)
0.686 Remote Similarity NPD1945 Phase 1
0.6847 Remote Similarity NPD7597 Clinical (unspecified phase)
0.6842 Remote Similarity NPD7559 Phase 2
0.6829 Remote Similarity NPD5514 Discontinued
0.6825 Remote Similarity NPD7449 Clinical (unspecified phase)
0.6822 Remote Similarity NPD3912 Discontinued
0.6818 Remote Similarity NPD3006 Discontinued
0.6814 Remote Similarity NPD6644 Discontinued
0.6813 Remote Similarity NPD2672 Discontinued
0.681 Remote Similarity NPD8149 Discontinued
0.6802 Remote Similarity NPD5994 Discontinued
0.6796 Remote Similarity NPD824 Approved
0.6794 Remote Similarity NPD3945 Discontinued
0.678 Remote Similarity NPD4130 Phase 3
0.6779 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6772 Remote Similarity NPD2248 Approved
0.6772 Remote Similarity NPD2246 Approved
0.6762 Remote Similarity NPD5293 Phase 2
0.676 Remote Similarity NPD5942 Approved
0.676 Remote Similarity NPD5941 Approved
0.6754 Remote Similarity NPD5334 Clinical (unspecified phase)
0.6754 Remote Similarity NPD4503 Phase 2
0.6751 Remote Similarity NPD5114 Approved
0.6751 Remote Similarity NPD5112 Approved
0.6751 Remote Similarity NPD5113 Approved
0.675 Remote Similarity NPD3964 Approved
0.6736 Remote Similarity NPD5192 Clinical (unspecified phase)
0.673 Remote Similarity NPD5025 Approved
0.6725 Remote Similarity NPD2949 Approved
0.6725 Remote Similarity NPD2950 Approved
0.672 Remote Similarity NPD1307 Phase 2
0.672 Remote Similarity NPD1309 Phase 2
0.6717 Remote Similarity NPD7668 Phase 2
0.6712 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6702 Remote Similarity NPD6457 Approved
0.6702 Remote Similarity NPD1544 Phase 1
0.6702 Remote Similarity NPD4020 Clinical (unspecified phase)
0.67 Remote Similarity NPD5457 Discontinued
0.67 Remote Similarity NPD7255 Clinical (unspecified phase)
0.6697 Remote Similarity NPD2951 Discontinued
0.6684 Remote Similarity NPD6297 Approved
0.6684 Remote Similarity NPD5078 Clinical (unspecified phase)
0.6684 Remote Similarity NPD3153 Approved
0.6684 Remote Similarity NPD3154 Approved
0.6683 Remote Similarity NPD3802 Phase 3
0.6667 Remote Similarity NPD3684 Discontinued
0.6667 Remote Similarity NPD7853 Phase 2
0.6667 Remote Similarity NPD1337 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4166 Phase 2
0.6667 Remote Similarity NPD5022 Discontinued
0.6667 Remote Similarity NPD7566 Clinical (unspecified phase)
0.6667 Remote Similarity NPD5910 Clinical (unspecified phase)
0.6652 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6648 Remote Similarity NPD814 Clinical (unspecified phase)
0.6648 Remote Similarity NPD160 Clinical (unspecified phase)
0.6648 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6637 Remote Similarity NPD8157 Clinical (unspecified phase)
0.6635 Remote Similarity NPD4859 Phase 1
0.6633 Remote Similarity NPD6853 Approved
0.6633 Remote Similarity NPD6851 Approved
0.6628 Remote Similarity NPD2245 Discovery
0.6618 Remote Similarity NPD6519 Phase 2
0.6617 Remote Similarity NPD7669 Phase 3
0.6615 Remote Similarity NPD3253 Clinical (unspecified phase)
0.6597 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6597 Remote Similarity NPD5997 Discontinued
0.6591 Remote Similarity NPD4981 Phase 2
0.659 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6587 Remote Similarity NPD7043 Discontinued
0.6585 Remote Similarity NPD3416 Discontinued
0.6583 Remote Similarity NPD4258 Approved
0.6583 Remote Similarity NPD4259 Approved
0.6582 Remote Similarity NPD6146 Clinical (unspecified phase)
0.6575 Remote Similarity NPD3899 Clinical (unspecified phase)
0.6573 Remote Similarity NPD5024 Approved
0.6571 Remote Similarity NPD4997 Clinical (unspecified phase)
0.6569 Remote Similarity NPD6874 Approved
0.6569 Remote Similarity NPD1880 Phase 3
0.6567 Remote Similarity NPD3631 Phase 3
0.6561 Remote Similarity NPD1559 Discontinued
0.6559 Remote Similarity NPD33 Approved
0.6559 Remote Similarity NPD4393 Approved
0.6559 Remote Similarity NPD6060 Clinical (unspecified phase)
0.6556 Remote Similarity NPD1305 Clinical (unspecified phase)
0.6556 Remote Similarity NPD2120 Phase 2
0.6555 Remote Similarity NPD7467 Discontinued
0.6555 Remote Similarity NPD5950 Discontinued
0.6555 Remote Similarity NPD2514 Approved
0.655 Remote Similarity NPD5042 Phase 1
0.655 Remote Similarity NPD5525 Clinical (unspecified phase)
0.6548 Remote Similarity NPD1421 Approved
0.6548 Remote Similarity NPD1420 Approved
0.6546 Remote Similarity NPD5900 Clinical (unspecified phase)
0.6545 Remote Similarity NPD5680 Clinical (unspecified phase)
0.6544 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6544 Remote Similarity NPD8311 Discontinued
0.6538 Remote Similarity NPD2737 Clinical (unspecified phase)
0.6534 Remote Similarity NPD1110 Approved
0.6534 Remote Similarity NPD1109 Approved
0.6533 Remote Similarity NPD5620 Clinical (unspecified phase)
0.6531 Remote Similarity NPD7190 Clinical (unspecified phase)
0.653 Remote Similarity NPD7186 Phase 3
0.6528 Remote Similarity NPD6242 Discontinued
0.6528 Remote Similarity NPD2822 Clinical (unspecified phase)
0.6526 Remote Similarity NPD2821 Approved
0.6526 Remote Similarity NPD4679 Discontinued
0.6526 Remote Similarity NPD6379 Discontinued
0.6522 Remote Similarity NPD7064 Clinical (unspecified phase)
0.652 Remote Similarity NPD5197 Approved
0.652 Remote Similarity NPD5196 Approved
0.652 Remote Similarity NPD5194 Approved
0.6517 Remote Similarity NPD6768 Approved
0.6512 Remote Similarity NPD5632 Approved
0.651 Remote Similarity NPD5858 Discontinued
0.6507 Remote Similarity NPD2434 Approved
0.65 Remote Similarity NPD7994 Phase 2
0.6495 Remote Similarity NPD5521 Clinical (unspecified phase)
0.6495 Remote Similarity NPD5600 Discontinued
0.6495 Remote Similarity NPD3793 Phase 3
0.6489 Remote Similarity NPD4368 Phase 2
0.6485 Remote Similarity NPD1059 Phase 2
0.6484 Remote Similarity NPD7528 Approved
0.6481 Remote Similarity NPD2899 Discontinued
0.6477 Remote Similarity NPD5938 Phase 3
0.6476 Remote Similarity NPD6593 Clinical (unspecified phase)
0.6476 Remote Similarity NPD4154 Approved
0.6473 Remote Similarity NPD956 Clinical (unspecified phase)
0.6471 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6468 Remote Similarity NPD3808 Clinical (unspecified phase)
0.6465 Remote Similarity NPD6719 Approved
0.6458 Remote Similarity NPD4083 Discontinued
0.6456 Remote Similarity NPD4491 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   54764239
ChEMBL   CHEMBL1922537
ZINC  

Physicochemical Properties

Molecular Weight:  272.15
ALogP:  -1.0363
MLogP:  2.78
XLogP:  1.782
# Rotatable Bonds:  4
Polar Surface Area:  41.57
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  20

Download Data

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Structure MOL file  
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Biological Activities  
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