Natural Product: NPC197335

Natural Product ID:  NPC197335
Common Name:   Usabamycin B
IUPAC Name:   (6aS,8E)-8-ethylidene-4-methoxy-6,6a,7,9-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-11-one
Synonyms:   Usabamycin B
Molecular Formula:   C15H18N2O2
Standard InCHIKey:  YZASJELCRXLHII-LFJXOHPOSA-N
Standard InCHI:  InChI=1S/C15H18N2O2/c1-3-10-7-11-8-16-14-12(15(18)17(11)9-10)5-4-6-13(14)19-2/h3-6,11,16H,7-9H2,1-2H3/b10-3+/t11-/m0/s1
Canonical SMILES:  C/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
NPO32984 streptomyces sp. 11a057 Species Streptomycetaceae Bacteria PMID[24613164]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT15 Cell Line Jurkat Homo sapiens IC50 = 6260 nM 23398362
NPT116 Cell Line HL-60 Homo sapiens IC50 = 13500 nM 12134945
NPT291 Individual Protein Serotonin 2b (5-HT2b) receptor Homo sapiens IC50 = 8450 nM 9090874
NPT111 Cell Line K562 Homo sapiens IC50 = 10100 nM 15730253
NPT291 Individual Protein Serotonin 2b (5-HT2b) receptor Homo sapiens Ki = 5380 nM 16005626
NPT165 Cell Line HeLa Homo sapiens IC50 = 103500 nM DrugMatrix in vivo data: Hematology
NPT65 Cell Line HepG2 Homo sapiens IC50 = 10600 nM 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 NPC197335 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 NPC314659
0.9521 High Similarity NPC87391
0.8613 High Similarity NPC270301
0.8284 Intermediate Similarity NPC257763
0.8197 Intermediate Similarity NPC198401
0.8011 Intermediate Similarity NPC316282
0.7746 Intermediate Similarity NPC301163
0.7692 Intermediate Similarity NPC472163
0.76 Intermediate Similarity NPC93653
0.7592 Intermediate Similarity NPC112937
0.7546 Intermediate Similarity NPC316104
0.7546 Intermediate Similarity NPC162417
0.7538 Intermediate Similarity NPC163829
0.7536 Intermediate Similarity NPC314702
0.7462 Intermediate Similarity NPC478075
0.7404 Intermediate Similarity NPC257851
0.7363 Intermediate Similarity NPC73280
0.7323 Intermediate Similarity NPC158551
0.7231 Intermediate Similarity NPC100863
0.7225 Intermediate Similarity NPC122886
0.7166 Intermediate Similarity NPC283810
0.7166 Intermediate Similarity NPC85613
0.7166 Intermediate Similarity NPC5167
0.7158 Intermediate Similarity NPC262725
0.7135 Intermediate Similarity NPC470708
0.712 Intermediate Similarity NPC471648
0.7098 Intermediate Similarity NPC92803
0.7083 Intermediate Similarity NPC173295
0.7077 Intermediate Similarity NPC243626
0.7077 Intermediate Similarity NPC230313
0.7065 Intermediate Similarity NPC246140
0.7065 Intermediate Similarity NPC195787
0.7049 Intermediate Similarity NPC471652
0.7047 Intermediate Similarity NPC45389
0.7045 Intermediate Similarity NPC241392
0.7037 Intermediate Similarity NPC28368
0.7037 Intermediate Similarity NPC116096
0.7024 Intermediate Similarity NPC266425
0.7016 Intermediate Similarity NPC473007
0.6995 Remote Similarity NPC329567
0.6995 Remote Similarity NPC330683
0.6995 Remote Similarity NPC299582
0.6995 Remote Similarity NPC18890
0.698 Remote Similarity NPC477161
0.697 Remote Similarity NPC71124
0.6942 Remote Similarity NPC470482
0.6942 Remote Similarity NPC470481
0.6939 Remote Similarity NPC254957
0.6923 Remote Similarity NPC22476
0.6916 Remote Similarity NPC157931
0.6905 Remote Similarity NPC288987
0.6895 Remote Similarity NPC70092
0.6884 Remote Similarity NPC218733
0.6884 Remote Similarity NPC132874
0.6884 Remote Similarity NPC138615
0.6884 Remote Similarity NPC265642
0.6881 Remote Similarity NPC41216
0.6872 Remote Similarity NPC473008
0.685 Remote Similarity NPC5374
0.6847 Remote Similarity NPC268077
0.6842 Remote Similarity NPC287152
0.6829 Remote Similarity NPC285192
0.6825 Remote Similarity NPC8467
0.681 Remote Similarity NPC313327
0.6802 Remote Similarity NPC473004
0.6798 Remote Similarity NPC207971
0.6796 Remote Similarity NPC477160
0.6792 Remote Similarity NPC323969
0.6786 Remote Similarity NPC5630
0.6782 Remote Similarity NPC471164
0.678 Remote Similarity NPC16249
0.678 Remote Similarity NPC146370
0.6777 Remote Similarity NPC77777
0.6769 Remote Similarity NPC21425
0.6765 Remote Similarity NPC475147
0.6759 Remote Similarity NPC478078
0.6758 Remote Similarity NPC172222
0.6733 Remote Similarity NPC138830
0.673 Remote Similarity NPC126556
0.6719 Remote Similarity NPC166169
0.6705 Remote Similarity NPC43218
0.6701 Remote Similarity NPC302235
0.6699 Remote Similarity NPC212123
0.6698 Remote Similarity NPC248601
0.6686 Remote Similarity NPC43477
0.6683 Remote Similarity NPC471304
0.6667 Remote Similarity NPC41488
0.6667 Remote Similarity NPC1464
0.6667 Remote Similarity NPC471649
0.6651 Remote Similarity NPC187501
0.6651 Remote Similarity NPC471197
0.6651 Remote Similarity NPC471762
0.6649 Remote Similarity NPC33507
0.6648 Remote Similarity NPC119669
0.6635 Remote Similarity NPC475133
0.663 Remote Similarity NPC314223
0.6628 Remote Similarity NPC253476
0.6622 Remote Similarity NPC154922
0.662 Remote Similarity NPC471198
0.662 Remote Similarity NPC195120
0.662 Remote Similarity NPC87560
0.6618 Remote Similarity NPC469732
0.6616 Remote Similarity NPC474059
0.6616 Remote Similarity NPC174629
0.6607 Remote Similarity NPC250476
0.6606 Remote Similarity NPC329631
0.6603 Remote Similarity NPC474366
0.66 Remote Similarity NPC470485
0.659 Remote Similarity NPC115588
0.6589 Remote Similarity NPC475609
0.6588 Remote Similarity NPC30749
0.6588 Remote Similarity NPC268223
0.6588 Remote Similarity NPC39500
0.6587 Remote Similarity NPC207873
0.6587 Remote Similarity NPC100573
0.6584 Remote Similarity NPC161804
0.6583 Remote Similarity NPC1820
0.6578 Remote Similarity NPC148889
0.6578 Remote Similarity NPC189116
0.6577 Remote Similarity NPC39370
0.6575 Remote Similarity NPC66777
0.6575 Remote Similarity NPC194740
0.6575 Remote Similarity NPC311906
0.6575 Remote Similarity NPC144691
0.6571 Remote Similarity NPC319645
0.6561 Remote Similarity NPC196718
0.6561 Remote Similarity NPC139373
0.6561 Remote Similarity NPC471651
0.6561 Remote Similarity NPC473186
0.6561 Remote Similarity NPC102593
0.6546 Remote Similarity NPC98416
0.6545 Remote Similarity NPC223242
0.6542 Remote Similarity NPC96321
0.654 Remote Similarity NPC119722
0.6538 Remote Similarity NPC469540
0.6538 Remote Similarity NPC469539
0.6522 Remote Similarity NPC473422
0.6522 Remote Similarity NPC87714
0.6519 Remote Similarity NPC324081
0.6519 Remote Similarity NPC242000
0.6517 Remote Similarity NPC308197
0.6514 Remote Similarity NPC122553
0.6512 Remote Similarity NPC222046
0.6508 Remote Similarity NPC279527
0.6508 Remote Similarity NPC214960
0.65 Remote Similarity NPC471647
0.65 Remote Similarity NPC470483
0.65 Remote Similarity NPC9373
0.65 Remote Similarity NPC471646
0.65 Remote Similarity NPC203628
0.6497 Remote Similarity NPC322621
0.6495 Remote Similarity NPC195636
0.6488 Remote Similarity NPC67904
0.6488 Remote Similarity NPC226794
0.6486 Remote Similarity NPC49547
0.6481 Remote Similarity NPC157983
0.6481 Remote Similarity NPC472099
0.6481 Remote Similarity NPC118154
0.6481 Remote Similarity NPC225279
0.6479 Remote Similarity NPC314817
0.6479 Remote Similarity NPC66191
0.6479 Remote Similarity NPC316297
0.6479 Remote Similarity NPC148391
0.6479 Remote Similarity NPC2905
0.6476 Remote Similarity NPC113455
0.6473 Remote Similarity NPC473460
0.6468 Remote Similarity NPC204970
0.6465 Remote Similarity NPC303658
0.6465 Remote Similarity NPC184408
0.6462 Remote Similarity NPC305542
0.6459 Remote Similarity NPC321428
0.6455 Remote Similarity NPC70172
0.6453 Remote Similarity NPC231382
0.6452 Remote Similarity NPC76478
0.645 Remote Similarity NPC473569
0.6445 Remote Similarity NPC269449
0.6442 Remote Similarity NPC470484
0.6436 Remote Similarity NPC230942
0.6436 Remote Similarity NPC315498
0.6435 Remote Similarity NPC208084
0.6433 Remote Similarity NPC122235
0.6432 Remote Similarity NPC114468
0.6429 Remote Similarity NPC254698
0.6422 Remote Similarity NPC470021
0.6422 Remote Similarity NPC144452
0.6421 Remote Similarity NPC182131
0.6416 Remote Similarity NPC301501
0.6415 Remote Similarity NPC218303
0.6411 Remote Similarity NPC225400
0.6406 Remote Similarity NPC476069
0.6402 Remote Similarity NPC50562
0.6402 Remote Similarity NPC176113
0.6402 Remote Similarity NPC135006
0.6396 Remote Similarity NPC99723
0.6393 Remote Similarity NPC214239
0.6391 Remote Similarity NPC120239
0.6389 Remote Similarity NPC131885
0.6389 Remote Similarity NPC134702
0.6389 Remote Similarity NPC182853
0.6385 Remote Similarity NPC10732

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC197335 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
0.7966 Intermediate Similarity NPD5603 Clinical (unspecified phase)
0.7869 Intermediate Similarity NPD4515 Suspended
0.7688 Intermediate Similarity NPD5896 Clinical (unspecified phase)
0.764 Intermediate Similarity NPD5183 Approved
0.764 Intermediate Similarity NPD5186 Approved
0.7541 Intermediate Similarity NPD6654 Clinical (unspecified phase)
0.7538 Intermediate Similarity NPD4492 Approved
0.7538 Intermediate Similarity NPD4494 Approved
0.7486 Intermediate Similarity NPD2681 Approved
0.7486 Intermediate Similarity NPD2680 Approved
0.745 Intermediate Similarity NPD3888 Discontinued
0.7443 Intermediate Similarity NPD5294 Clinical (unspecified phase)
0.7436 Intermediate Similarity NPD7071 Clinical (unspecified phase)
0.7424 Intermediate Similarity NPD4082 Approved
0.7424 Intermediate Similarity NPD4022 Approved
0.7424 Intermediate Similarity NPD3472 Approved
0.7409 Intermediate Similarity NPD5071 Phase 2
0.7385 Intermediate Similarity NPD6238 Discontinued
0.735 Intermediate Similarity NPD3372 Discontinued
0.735 Intermediate Similarity NPD3893 Discontinued
0.7347 Intermediate Similarity NPD6795 Clinical (unspecified phase)
0.7327 Intermediate Similarity NPD4455 Discontinued
0.7313 Intermediate Similarity NPD4493 Discontinued
0.7304 Intermediate Similarity NPD3940 Clinical (unspecified phase)
0.7288 Intermediate Similarity NPD1769 Discontinued
0.7287 Intermediate Similarity NPD6021 Clinical (unspecified phase)
0.7282 Intermediate Similarity NPD7858 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD4465 Phase 2
0.7273 Intermediate Similarity NPD4467 Phase 2
0.7232 Intermediate Similarity NPD4205 Phase 3
0.72 Intermediate Similarity NPD4596 Phase 1
0.7198 Intermediate Similarity NPD5433 Clinical (unspecified phase)
0.7198 Intermediate Similarity NPD2249 Approved
0.7198 Intermediate Similarity NPD2247 Approved
0.7186 Intermediate Similarity NPD4456 Clinical (unspecified phase)
0.7166 Intermediate Similarity NPD6293 Clinical (unspecified phase)
0.7101 Intermediate Similarity NPD743 Approved
0.71 Intermediate Similarity NPD5102 Clinical (unspecified phase)
0.7094 Intermediate Similarity NPD5860 Discontinued
0.705 Intermediate Similarity NPD6478 Clinical (unspecified phase)
0.7035 Intermediate Similarity NPD6321 Discontinued
0.7033 Intermediate Similarity NPD3783 Clinical (unspecified phase)
0.7031 Intermediate Similarity NPD4084 Clinical (unspecified phase)
0.703 Intermediate Similarity NPD5143 Clinical (unspecified phase)
0.7017 Intermediate Similarity NPD1012 Discontinued
0.7011 Intermediate Similarity NPD7126 Discontinued
0.7006 Intermediate Similarity NPD1670 Discontinued
0.7005 Intermediate Similarity NPD5515 Phase 2
0.6995 Remote Similarity NPD2907 Approved
0.6995 Remote Similarity NPD2906 Approved
0.6974 Remote Similarity NPD3479 Discontinued
0.6961 Remote Similarity NPD2842 Clinical (unspecified phase)
0.6952 Remote Similarity NPD6720 Clinical (unspecified phase)
0.6938 Remote Similarity NPD4429 Discontinued
0.6932 Remote Similarity NPD1802 Approved
0.6932 Remote Similarity NPD1801 Approved
0.6931 Remote Similarity NPD795 Clinical (unspecified phase)
0.693 Remote Similarity NPD6199 Discontinued
0.6915 Remote Similarity NPD6645 Clinical (unspecified phase)
0.6907 Remote Similarity NPD6608 Clinical (unspecified phase)
0.6882 Remote Similarity NPD5847 Phase 1
0.6872 Remote Similarity NPD3437 Discontinued
0.686 Remote Similarity NPD7225 Discontinued
0.6853 Remote Similarity NPD4539 Phase 1
0.6851 Remote Similarity NPD4201 Clinical (unspecified phase)
0.6848 Remote Similarity NPD6533 Clinical (unspecified phase)
0.6839 Remote Similarity NPD6618 Phase 2
0.6833 Remote Similarity NPD824 Approved
0.6821 Remote Similarity NPD5188 Clinical (unspecified phase)
0.6812 Remote Similarity NPD1945 Phase 1
0.6798 Remote Similarity NPD7597 Clinical (unspecified phase)
0.6794 Remote Similarity NPD7559 Phase 2
0.678 Remote Similarity NPD5514 Discontinued
0.6776 Remote Similarity NPD3912 Discontinued
0.6773 Remote Similarity NPD3006 Discontinued
0.6772 Remote Similarity NPD7449 Clinical (unspecified phase)
0.6765 Remote Similarity NPD6644 Discontinued
0.6762 Remote Similarity NPD8149 Discontinued
0.6758 Remote Similarity NPD2672 Discontinued
0.6757 Remote Similarity NPD1309 Phase 2
0.6757 Remote Similarity NPD1307 Phase 2
0.6751 Remote Similarity NPD5994 Discontinued
0.6746 Remote Similarity NPD3945 Discontinued
0.6737 Remote Similarity NPD1544 Phase 1
0.6732 Remote Similarity NPD4130 Phase 3
0.6731 Remote Similarity NPD6567 Clinical (unspecified phase)
0.672 Remote Similarity NPD2248 Approved
0.672 Remote Similarity NPD2246 Approved
0.6714 Remote Similarity NPD5293 Phase 2
0.6704 Remote Similarity NPD5942 Approved
0.6704 Remote Similarity NPD5941 Approved
0.6703 Remote Similarity NPD1337 Clinical (unspecified phase)
0.6702 Remote Similarity NPD5334 Clinical (unspecified phase)
0.6702 Remote Similarity NPD4503 Phase 2
0.6701 Remote Similarity NPD5112 Approved
0.6701 Remote Similarity NPD5114 Approved
0.6701 Remote Similarity NPD5113 Approved
0.67 Remote Similarity NPD3964 Approved
0.6685 Remote Similarity NPD160 Clinical (unspecified phase)
0.6685 Remote Similarity NPD814 Clinical (unspecified phase)
0.6684 Remote Similarity NPD5192 Clinical (unspecified phase)
0.6682 Remote Similarity NPD5025 Approved
0.6667 Remote Similarity NPD2949 Approved
0.6667 Remote Similarity NPD2950 Approved
0.6667 Remote Similarity NPD7668 Phase 2
0.6667 Remote Similarity NPD4958 Clinical (unspecified phase)
0.6652 Remote Similarity NPD2951 Discontinued
0.665 Remote Similarity NPD7255 Clinical (unspecified phase)
0.665 Remote Similarity NPD5457 Discontinued
0.6649 Remote Similarity NPD6457 Approved
0.6649 Remote Similarity NPD4020 Clinical (unspecified phase)
0.6634 Remote Similarity NPD3802 Phase 3
0.6633 Remote Similarity NPD3153 Approved
0.6633 Remote Similarity NPD3154 Approved
0.6632 Remote Similarity NPD6297 Approved
0.6632 Remote Similarity NPD5078 Clinical (unspecified phase)
0.6622 Remote Similarity NPD7853 Phase 2
0.6621 Remote Similarity NPD5022 Discontinued
0.6618 Remote Similarity NPD7566 Clinical (unspecified phase)
0.6616 Remote Similarity NPD5910 Clinical (unspecified phase)
0.6614 Remote Similarity NPD4166 Phase 2
0.6612 Remote Similarity NPD3684 Discontinued
0.6606 Remote Similarity NPD6741 Clinical (unspecified phase)
0.6596 Remote Similarity NPD1559 Discontinued
0.6592 Remote Similarity NPD1305 Clinical (unspecified phase)
0.6592 Remote Similarity NPD8157 Clinical (unspecified phase)
0.6592 Remote Similarity NPD6884 Clinical (unspecified phase)
0.6587 Remote Similarity NPD1420 Approved
0.6587 Remote Similarity NPD4859 Phase 1
0.6587 Remote Similarity NPD1421 Approved
0.6582 Remote Similarity NPD6853 Approved
0.6582 Remote Similarity NPD6851 Approved
0.6571 Remote Similarity NPD1109 Approved
0.6571 Remote Similarity NPD1110 Approved
0.657 Remote Similarity NPD2245 Discovery
0.6569 Remote Similarity NPD6519 Phase 2
0.6567 Remote Similarity NPD7669 Phase 3
0.6564 Remote Similarity NPD3253 Clinical (unspecified phase)
0.6545 Remote Similarity NPD3451 Clinical (unspecified phase)
0.6545 Remote Similarity NPD5997 Discontinued
0.6545 Remote Similarity NPD4981 Phase 2
0.6544 Remote Similarity NPD7547 Clinical (unspecified phase)
0.6538 Remote Similarity NPD7043 Discontinued
0.6537 Remote Similarity NPD3416 Discontinued
0.6533 Remote Similarity NPD4258 Approved
0.6533 Remote Similarity NPD4259 Approved
0.6531 Remote Similarity NPD6146 Clinical (unspecified phase)
0.653 Remote Similarity NPD3899 Clinical (unspecified phase)
0.6524 Remote Similarity NPD4997 Clinical (unspecified phase)
0.652 Remote Similarity NPD1880 Phase 3
0.652 Remote Similarity NPD6874 Approved
0.6517 Remote Similarity NPD3631 Phase 3
0.6517 Remote Similarity NPD1059 Phase 2
0.6517 Remote Similarity NPD5024 Approved
0.6507 Remote Similarity NPD7467 Discontinued
0.6507 Remote Similarity NPD2514 Approved
0.6507 Remote Similarity NPD5950 Discontinued
0.6505 Remote Similarity NPD6060 Clinical (unspecified phase)
0.6505 Remote Similarity NPD4393 Approved
0.6505 Remote Similarity NPD956 Clinical (unspecified phase)
0.6505 Remote Similarity NPD33 Approved
0.65 Remote Similarity NPD5525 Clinical (unspecified phase)
0.65 Remote Similarity NPD2120 Phase 2
0.65 Remote Similarity NPD5042 Phase 1
0.6498 Remote Similarity NPD8311 Discontinued
0.6498 Remote Similarity NPD6824 Clinical (unspecified phase)
0.6495 Remote Similarity NPD5900 Clinical (unspecified phase)
0.6492 Remote Similarity NPD5680 Clinical (unspecified phase)
0.6484 Remote Similarity NPD2737 Clinical (unspecified phase)
0.6484 Remote Similarity NPD7186 Phase 3
0.6482 Remote Similarity NPD5620 Clinical (unspecified phase)
0.6481 Remote Similarity NPD6242 Discontinued
0.648 Remote Similarity NPD7190 Clinical (unspecified phase)
0.6479 Remote Similarity NPD4679 Discontinued
0.6477 Remote Similarity NPD2822 Clinical (unspecified phase)
0.6474 Remote Similarity NPD2821 Approved
0.6474 Remote Similarity NPD6379 Discontinued
0.6473 Remote Similarity NPD7064 Clinical (unspecified phase)
0.6471 Remote Similarity NPD5196 Approved
0.6471 Remote Similarity NPD5197 Approved
0.6471 Remote Similarity NPD5194 Approved
0.6465 Remote Similarity NPD5632 Approved
0.6461 Remote Similarity NPD6768 Approved
0.6459 Remote Similarity NPD2434 Approved
0.6458 Remote Similarity NPD5858 Discontinued
0.6455 Remote Similarity NPD7994 Phase 2
0.6444 Remote Similarity NPD4368 Phase 2
0.6443 Remote Similarity NPD3793 Phase 3
0.6443 Remote Similarity NPD5521 Clinical (unspecified phase)
0.6443 Remote Similarity NPD5600 Discontinued
0.6436 Remote Similarity NPD1742 Approved
0.6436 Remote Similarity NPD1743 Approved
0.6436 Remote Similarity NPD19 Approved
0.6435 Remote Similarity NPD2899 Discontinued
0.6429 Remote Similarity NPD4154 Approved
0.6429 Remote Similarity NPD7528 Approved
0.6429 Remote Similarity NPD6593 Clinical (unspecified phase)
0.6425 Remote Similarity NPD5938 Phase 3
0.6422 Remote Similarity NPD7238 Clinical (unspecified phase)
0.6419 Remote Similarity NPD6719 Approved

Structure

External Identifiers

PubChem CID   54764241
ChEMBL   CHEMBL1922538
ZINC  

Physicochemical Properties

Molecular Weight:  258.14
ALogP:  -0.3601
MLogP:  2.67
XLogP:  1.318
# Rotatable Bonds:  3
Polar Surface Area:  41.57
# H-Bond Aceptor:  3
# H-Bond Donor:  1
# Rings:  3
# Heavy Atoms:  19

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Biological Activities  
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