Natural Product: NPC158699

Natural Product ID:  NPC158699
Common Name:   Napyradiomycin B3
IUPAC Name:   (3R,4aR,10aS)-10a-[[(1R,3S)-3-bromo-2,2-dimethyl-6-methylidenecyclohexyl]methyl]-3,4a-dichloro-6,8-dihydroxy-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione
Synonyms:  
Molecular Formula:   C25H29BrCl2O5
Standard InCHIKey:  PVEFIGXLPBGZAX-RVRKADHMSA-N
Standard InCHI:  InChI=1S/C25H29BrCl2O5/c1-12-6-7-17(26)22(2,3)15(12)10-25-20(31)14-8-13(29)9-16(30)19(14)21(32)24(25,28)11-18(27)23(4,5)33-25/h8-9,15,17-18,29-30H,1,6-7,10-11H2,2-5H3/t15-,17+,18-,24+,25+/m1/s1
Canonical SMILES:  Oc1cc(O)c2c(c1)C(=O)[C@]1([C@](C2=O)(Cl)C[C@H](C(O1)(C)C)Cl)C[C@@H]1C(=C)CC[C@@H](C1(C)C)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
NPO32325 Streptomyces cnq-329 Species Streptomycetaceae Bacteria StreptomeDB*
NPO20334 Streptomyces aculeolatus Species Streptomycetaceae Bacteria StreptomeDB*
NPO2873.1 Streptomyces antimycoticus nt17 Subspecies Streptomycetaceae Bacteria StreptomeDB*
NPO32026 Streptomyces cnh-070 Species Streptomycetaceae Bacteria StreptomeDB*
NPO32292 Streptomyces scsio 10428 Species Streptomycetaceae Bacteria StreptomeDB*

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT393 Cell Line HCT-116 Homo sapiens IC50 = 3000 nM 24328269

  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 NPC158699 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
0.939 High Similarity NPC311679
0.939 High Similarity NPC131078
0.9212 High Similarity NPC471685
0.9162 High Similarity NPC108948
0.9042 High Similarity NPC301846
0.8982 High Similarity NPC73544
0.8902 High Similarity NPC471686
0.8824 High Similarity NPC184518
0.8728 High Similarity NPC471684
0.8698 High Similarity NPC471687
0.7919 Intermediate Similarity NPC470564
0.7771 Intermediate Similarity NPC181560
0.7771 Intermediate Similarity NPC169452
0.7753 Intermediate Similarity NPC470563
0.7727 Intermediate Similarity NPC470559
0.7711 Intermediate Similarity NPC138099
0.7711 Intermediate Similarity NPC242994
0.7697 Intermediate Similarity NPC471905
0.7697 Intermediate Similarity NPC470561
0.7679 Intermediate Similarity NPC193555
0.7637 Intermediate Similarity NPC470565
0.7636 Intermediate Similarity NPC254847
0.7622 Intermediate Similarity NPC44437
0.7619 Intermediate Similarity NPC246638
0.7602 Intermediate Similarity NPC470570
0.7598 Intermediate Similarity NPC475106
0.759 Intermediate Similarity NPC53414
0.759 Intermediate Similarity NPC53206
0.7588 Intermediate Similarity NPC471906
0.7586 Intermediate Similarity NPC305965
0.7574 Intermediate Similarity NPC135524
0.7574 Intermediate Similarity NPC308572
0.7571 Intermediate Similarity NPC201127
0.7571 Intermediate Similarity NPC272196
0.7544 Intermediate Similarity NPC34482
0.7542 Intermediate Similarity NPC103816
0.7542 Intermediate Similarity NPC61382
0.7541 Intermediate Similarity NPC474004
0.7541 Intermediate Similarity NPC277865
0.7541 Intermediate Similarity NPC470562
0.753 Intermediate Similarity NPC191976
0.7515 Intermediate Similarity NPC305845
0.7515 Intermediate Similarity NPC166480
0.7515 Intermediate Similarity NPC282780
0.7515 Intermediate Similarity NPC204045
0.7514 Intermediate Similarity NPC316262
0.7514 Intermediate Similarity NPC94781
0.7514 Intermediate Similarity NPC314653
0.75 Intermediate Similarity NPC143438
0.75 Intermediate Similarity NPC470560
0.7486 Intermediate Similarity NPC54903
0.7486 Intermediate Similarity NPC472618
0.7486 Intermediate Similarity NPC286074
0.7485 Intermediate Similarity NPC193703
0.7485 Intermediate Similarity NPC19896
0.7485 Intermediate Similarity NPC21599
0.7485 Intermediate Similarity NPC48762
0.7473 Intermediate Similarity NPC125465
0.7473 Intermediate Similarity NPC17274
0.7473 Intermediate Similarity NPC85047
0.7473 Intermediate Similarity NPC120857
0.7472 Intermediate Similarity NPC197326
0.7472 Intermediate Similarity NPC474637
0.7471 Intermediate Similarity NPC120171
0.7457 Intermediate Similarity NPC37709
0.7457 Intermediate Similarity NPC190648
0.7457 Intermediate Similarity NPC126767
0.7457 Intermediate Similarity NPC289042
0.7457 Intermediate Similarity NPC245584
0.7457 Intermediate Similarity NPC118027
0.7457 Intermediate Similarity NPC312929
0.7457 Intermediate Similarity NPC56433
0.7456 Intermediate Similarity NPC156872
0.7455 Intermediate Similarity NPC267205
0.7443 Intermediate Similarity NPC154683
0.7443 Intermediate Similarity NPC40356
0.7442 Intermediate Similarity NPC470674
0.7442 Intermediate Similarity NPC470673
0.7442 Intermediate Similarity NPC117716
0.7442 Intermediate Similarity NPC12402
0.743 Intermediate Similarity NPC472617
0.7429 Intermediate Similarity NPC470568
0.7427 Intermediate Similarity NPC451542
0.7427 Intermediate Similarity NPC295712
0.7427 Intermediate Similarity NPC474203
0.7427 Intermediate Similarity NPC313047
0.7427 Intermediate Similarity NPC293545
0.7427 Intermediate Similarity NPC174905
0.7419 Intermediate Similarity NPC264922
0.7418 Intermediate Similarity NPC472049
0.7416 Intermediate Similarity NPC280497
0.7416 Intermediate Similarity NPC4547
0.7412 Intermediate Similarity NPC110810
0.7401 Intermediate Similarity NPC214632
0.7399 Intermediate Similarity NPC470676
0.7399 Intermediate Similarity NPC473135
0.7399 Intermediate Similarity NPC473132
0.7396 Intermediate Similarity NPC103337
0.7396 Intermediate Similarity NPC190457
0.7396 Intermediate Similarity NPC114620
0.7394 Intermediate Similarity NPC175738
0.7391 Intermediate Similarity NPC20734
0.7389 Intermediate Similarity NPC475107
0.7389 Intermediate Similarity NPC313368
0.7389 Intermediate Similarity NPC43490
0.7386 Intermediate Similarity NPC470569
0.7384 Intermediate Similarity NPC244691
0.7381 Intermediate Similarity NPC53001
0.7377 Intermediate Similarity NPC476056
0.7374 Intermediate Similarity NPC472404
0.7371 Intermediate Similarity NPC44378
0.7371 Intermediate Similarity NPC84142
0.7371 Intermediate Similarity NPC280753
0.7371 Intermediate Similarity NPC10027
0.7371 Intermediate Similarity NPC329933
0.7371 Intermediate Similarity NPC65775
0.7368 Intermediate Similarity NPC474961
0.7368 Intermediate Similarity NPC291078
0.7366 Intermediate Similarity NPC469393
0.7363 Intermediate Similarity NPC100849
0.7362 Intermediate Similarity NPC179898
0.736 Intermediate Similarity NPC226656
0.736 Intermediate Similarity NPC66508
0.736 Intermediate Similarity NPC314257
0.7356 Intermediate Similarity NPC34802
0.7356 Intermediate Similarity NPC5568
0.7354 Intermediate Similarity NPC151292
0.7353 Intermediate Similarity NPC203063
0.7351 Intermediate Similarity NPC193698
0.7351 Intermediate Similarity NPC313717
0.7351 Intermediate Similarity NPC315306
0.7348 Intermediate Similarity NPC476929
0.7348 Intermediate Similarity NPC472906
0.7345 Intermediate Similarity NPC470353
0.7345 Intermediate Similarity NPC268992
0.7345 Intermediate Similarity NPC180944
0.7345 Intermediate Similarity NPC51824
0.7345 Intermediate Similarity NPC113608
0.7345 Intermediate Similarity NPC470337
0.7345 Intermediate Similarity NPC470338
0.7345 Intermediate Similarity NPC470340
0.7341 Intermediate Similarity NPC474630
0.7341 Intermediate Similarity NPC28632
0.7337 Intermediate Similarity NPC476306
0.7337 Intermediate Similarity NPC193222
0.7337 Intermediate Similarity NPC470566
0.7337 Intermediate Similarity NPC87723
0.7337 Intermediate Similarity NPC13715
0.733 Intermediate Similarity NPC205766
0.733 Intermediate Similarity NPC147735
0.733 Intermediate Similarity NPC294646
0.733 Intermediate Similarity NPC290954
0.733 Intermediate Similarity NPC255641
0.733 Intermediate Similarity NPC164762
0.7326 Intermediate Similarity NPC100242
0.7326 Intermediate Similarity NPC271451
0.7318 Intermediate Similarity NPC470354
0.7318 Intermediate Similarity NPC470352
0.7317 Intermediate Similarity NPC92624
0.7317 Intermediate Similarity NPC303910
0.7314 Intermediate Similarity NPC142846
0.7312 Intermediate Similarity NPC118128
0.7312 Intermediate Similarity NPC474857
0.731 Intermediate Similarity NPC290550
0.7308 Intermediate Similarity NPC473022
0.7308 Intermediate Similarity NPC94796
0.7308 Intermediate Similarity NPC245122
0.7305 Intermediate Similarity NPC12070
0.7303 Intermediate Similarity NPC474824
0.7303 Intermediate Similarity NPC329844
0.7303 Intermediate Similarity NPC470408
0.7303 Intermediate Similarity NPC178964
0.7303 Intermediate Similarity NPC182921
0.7303 Intermediate Similarity NPC95842
0.7303 Intermediate Similarity NPC218870
0.7303 Intermediate Similarity NPC280530
0.7303 Intermediate Similarity NPC472211
0.7299 Intermediate Similarity NPC110882
0.7299 Intermediate Similarity NPC136878
0.7299 Intermediate Similarity NPC271944
0.7299 Intermediate Similarity NPC51513
0.7299 Intermediate Similarity NPC202112
0.7299 Intermediate Similarity NPC85393
0.7297 Intermediate Similarity NPC470567
0.7288 Intermediate Similarity NPC149526
0.7288 Intermediate Similarity NPC46882
0.7288 Intermediate Similarity NPC478148
0.7288 Intermediate Similarity NPC205918
0.7288 Intermediate Similarity NPC132990
0.7288 Intermediate Similarity NPC474417
0.7288 Intermediate Similarity NPC91809
0.7288 Intermediate Similarity NPC230848
0.7284 Intermediate Similarity NPC477454
0.7283 Intermediate Similarity NPC474061
0.7283 Intermediate Similarity NPC227841
0.7273 Intermediate Similarity NPC470422
0.7273 Intermediate Similarity NPC473978
0.7273 Intermediate Similarity NPC474310
0.7273 Intermediate Similarity NPC259942
0.7273 Intermediate Similarity NPC108129

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC158699 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
0.7636 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7390 Discontinued
0.7073 Intermediate Similarity NPD1470 Approved
0.6973 Remote Similarity NPD6959 Discontinued
0.6949 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6949 Remote Similarity NPD4378 Clinical (unspecified phase)
0.6923 Remote Similarity NPD7819 Suspended
0.6919 Remote Similarity NPD651 Clinical (unspecified phase)
0.6915 Remote Similarity NPD7473 Discontinued
0.6902 Remote Similarity NPD3749 Approved
0.6897 Remote Similarity NPD970 Clinical (unspecified phase)
0.6885 Remote Similarity NPD8443 Clinical (unspecified phase)
0.6885 Remote Similarity NPD8438 Clinical (unspecified phase)
0.6882 Remote Similarity NPD943 Approved
0.6879 Remote Similarity NPD6100 Approved
0.6879 Remote Similarity NPD5406 Approved
0.6879 Remote Similarity NPD5404 Approved
0.6879 Remote Similarity NPD5408 Approved
0.6879 Remote Similarity NPD6099 Approved
0.6879 Remote Similarity NPD5405 Approved
0.6845 Remote Similarity NPD6232 Discontinued
0.6829 Remote Similarity NPD1201 Approved
0.6811 Remote Similarity NPD7075 Discontinued
0.6768 Remote Similarity NPD7879 Clinical (unspecified phase)
0.676 Remote Similarity NPD2532 Approved
0.676 Remote Similarity NPD2534 Approved
0.676 Remote Similarity NPD2533 Approved
0.6758 Remote Similarity NPD4380 Phase 2
0.6758 Remote Similarity NPD6599 Discontinued
0.6757 Remote Similarity NPD3882 Suspended
0.6739 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6739 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6724 Remote Similarity NPD1510 Phase 2
0.6723 Remote Similarity NPD6398 Clinical (unspecified phase)
0.6721 Remote Similarity NPD7411 Suspended
0.6705 Remote Similarity NPD1607 Approved
0.6705 Remote Similarity NPD1549 Phase 2
0.6686 Remote Similarity NPD1240 Approved
0.6684 Remote Similarity NPD6784 Approved
0.6684 Remote Similarity NPD6168 Clinical (unspecified phase)
0.6684 Remote Similarity NPD2403 Approved
0.6684 Remote Similarity NPD6166 Phase 2
0.6684 Remote Similarity NPD6785 Approved
0.6684 Remote Similarity NPD6167 Clinical (unspecified phase)
0.6667 Remote Similarity NPD4287 Approved
0.6667 Remote Similarity NPD2800 Approved
0.665 Remote Similarity NPD8150 Discontinued
0.6648 Remote Similarity NPD1550 Clinical (unspecified phase)
0.6648 Remote Similarity NPD1552 Clinical (unspecified phase)
0.6648 Remote Similarity NPD3300 Phase 2
0.663 Remote Similarity NPD1512 Approved
0.6629 Remote Similarity NPD3299 Clinical (unspecified phase)
0.6629 Remote Similarity NPD3750 Approved
0.6612 Remote Similarity NPD3226 Approved
0.6597 Remote Similarity NPD7852 Clinical (unspecified phase)
0.6595 Remote Similarity NPD1934 Approved
0.6575 Remote Similarity NPD7422 Clinical (unspecified phase)
0.6561 Remote Similarity NPD5494 Approved
0.6559 Remote Similarity NPD2801 Approved
0.6535 Remote Similarity NPD6535 Approved
0.6535 Remote Similarity NPD6534 Approved
0.6519 Remote Similarity NPD6799 Approved
0.6519 Remote Similarity NPD1511 Approved
0.6514 Remote Similarity NPD6651 Approved
0.6506 Remote Similarity NPD3019 Approved
0.6505 Remote Similarity NPD6801 Discontinued
0.6497 Remote Similarity NPD2796 Approved
0.6495 Remote Similarity NPD5844 Phase 1
0.6495 Remote Similarity NPD7804 Clinical (unspecified phase)
0.649 Remote Similarity NPD8320 Phase 1
0.649 Remote Similarity NPD8319 Approved
0.6489 Remote Similarity NPD4868 Clinical (unspecified phase)
0.6489 Remote Similarity NPD7768 Phase 2
0.6474 Remote Similarity NPD3764 Approved
0.6463 Remote Similarity NPD405 Clinical (unspecified phase)
0.6456 Remote Similarity NPD6776 Approved
0.6456 Remote Similarity NPD6779 Approved
0.6456 Remote Similarity NPD6778 Approved
0.6456 Remote Similarity NPD6782 Approved
0.6456 Remote Similarity NPD6781 Approved
0.6456 Remote Similarity NPD6780 Approved
0.6456 Remote Similarity NPD6777 Approved
0.6455 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6453 Remote Similarity NPD4360 Phase 2
0.6453 Remote Similarity NPD4363 Phase 3
0.6443 Remote Similarity NPD3751 Discontinued
0.6442 Remote Similarity NPD7435 Discontinued
0.6439 Remote Similarity NPD7700 Phase 2
0.6439 Remote Similarity NPD7699 Phase 2
0.6436 Remote Similarity NPD4288 Approved
0.6436 Remote Similarity NPD3817 Phase 2
0.6429 Remote Similarity NPD6797 Phase 2
0.6407 Remote Similarity NPD2932 Approved
0.6406 Remote Similarity NPD5710 Approved
0.6406 Remote Similarity NPD5711 Approved
0.6396 Remote Similarity NPD7251 Discontinued
0.6383 Remote Similarity NPD1465 Phase 2
0.6369 Remote Similarity NPD2346 Discontinued
0.6364 Remote Similarity NPD7696 Phase 3
0.6364 Remote Similarity NPD7697 Approved
0.6364 Remote Similarity NPD4338 Clinical (unspecified phase)
0.6364 Remote Similarity NPD7808 Phase 3
0.6364 Remote Similarity NPD7698 Approved
0.6349 Remote Similarity NPD5402 Approved
0.6348 Remote Similarity NPD3748 Approved
0.6347 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6345 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6333 Remote Similarity NPD7870 Phase 2
0.6333 Remote Similarity NPD7871 Phase 2
0.6313 Remote Similarity NPD2935 Discontinued
0.6294 Remote Similarity NPD4878 Approved
0.6294 Remote Similarity NPD7074 Phase 3
0.6289 Remote Similarity NPD3926 Phase 2
0.6278 Remote Similarity NPD1471 Phase 3
0.6278 Remote Similarity NPD2344 Approved
0.6276 Remote Similarity NPD3818 Discontinued
0.6271 Remote Similarity NPD230 Phase 1
0.6269 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6264 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6264 Remote Similarity NPD8166 Discontinued
0.6264 Remote Similarity NPD7003 Approved
0.6263 Remote Similarity NPD2296 Approved
0.6262 Remote Similarity NPD4362 Clinical (unspecified phase)
0.6262 Remote Similarity NPD7875 Clinical (unspecified phase)
0.6262 Remote Similarity NPD7874 Approved
0.6262 Remote Similarity NPD4361 Phase 2
0.6257 Remote Similarity NPD2799 Discontinued
0.6244 Remote Similarity NPD7701 Phase 2
0.6244 Remote Similarity NPD6020 Phase 2
0.6244 Remote Similarity NPD7054 Approved
0.6238 Remote Similarity NPD8434 Phase 2
0.6237 Remote Similarity NPD5403 Approved
0.6237 Remote Similarity NPD3787 Discontinued
0.6233 Remote Similarity NPD7801 Approved
0.6231 Remote Similarity NPD6559 Discontinued
0.623 Remote Similarity NPD6190 Approved
0.6226 Remote Similarity NPD7211 Clinical (unspecified phase)
0.6216 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6215 Remote Similarity NPD8151 Discontinued
0.6212 Remote Similarity NPD7472 Approved
0.6209 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6196 Remote Similarity NPD7236 Approved
0.6185 Remote Similarity NPD1164 Approved
0.6181 Remote Similarity NPD5953 Discontinued
0.6176 Remote Similarity NPD3026 Approved
0.6176 Remote Similarity NPD4879 Approved
0.6176 Remote Similarity NPD3023 Approved
0.617 Remote Similarity NPD7458 Discontinued
0.617 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6169 Remote Similarity NPD8313 Approved
0.6169 Remote Similarity NPD8312 Approved
0.6158 Remote Similarity NPD6663 Approved
0.6154 Remote Similarity NPD3025 Approved
0.6154 Remote Similarity NPD3024 Approved
0.6143 Remote Similarity NPD4914 Approved
0.6141 Remote Similarity NPD2309 Approved
0.6141 Remote Similarity NPD2354 Approved
0.6136 Remote Similarity NPD4625 Phase 3
0.6133 Remote Similarity NPD1551 Phase 2
0.6129 Remote Similarity NPD5401 Approved
0.6126 Remote Similarity NPD5761 Phase 2
0.6126 Remote Similarity NPD5760 Phase 2
0.6124 Remote Similarity NPD4975 Approved
0.6124 Remote Similarity NPD4974 Approved
0.612 Remote Similarity NPD1243 Approved
0.6119 Remote Similarity NPD4419 Clinical (unspecified phase)
0.6114 Remote Similarity NPD5736 Approved
0.6105 Remote Similarity NPD9269 Phase 2
0.6103 Remote Similarity NPD1247 Approved
0.6102 Remote Similarity NPD4907 Clinical (unspecified phase)
0.6102 Remote Similarity NPD6410 Clinical (unspecified phase)
0.6098 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6096 Remote Similarity NPD6273 Approved
0.6095 Remote Similarity NPD5544 Approved
0.6087 Remote Similarity NPD6214 Clinical (unspecified phase)
0.6087 Remote Similarity NPD6212 Phase 3
0.6087 Remote Similarity NPD6213 Phase 3
0.6087 Remote Similarity NPD4628 Phase 3
0.6082 Remote Similarity NPD919 Approved
0.6082 Remote Similarity NPD6234 Discontinued
0.608 Remote Similarity NPD4908 Phase 1
0.6077 Remote Similarity NPD4915 Approved
0.6073 Remote Similarity NPD37 Approved
0.607 Remote Similarity NPD5027 Approved
0.607 Remote Similarity NPD5031 Approved
0.607 Remote Similarity NPD5029 Approved
0.6069 Remote Similarity NPD4749 Approved
0.6066 Remote Similarity NPD7501 Clinical (unspecified phase)
0.6062 Remote Similarity NPD4967 Phase 2
0.6062 Remote Similarity NPD4965 Approved
0.6062 Remote Similarity NPD4966 Approved
0.6059 Remote Similarity NPD9268 Approved
0.6057 Remote Similarity NPD2798 Approved
0.6041 Remote Similarity NPD7184 Clinical (unspecified phase)
0.604 Remote Similarity NPD5026 Approved
0.604 Remote Similarity NPD5028 Approved
0.604 Remote Similarity NPD4954 Approved
0.604 Remote Similarity NPD36 Approved
0.604 Remote Similarity NPD4955 Approved
0.604 Remote Similarity NPD5034 Approved

Structure

External Identifiers

PubChem CID   76321117
ChEMBL   CHEMBL3104844
ZINC  

Physicochemical Properties

Molecular Weight:  558.06
ALogP:  2.0862
MLogP:  3.33
XLogP:  3.764
# Rotatable Bonds:  11
Polar Surface Area:  83.83
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  4
# Heavy Atoms:  33

Download Data

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