Natural Product: NPC469385

Natural Product ID:  NPC469385
Common Name:   Ustusorane A
IUPAC Name:   7-(hydroxymethyl)-6-(2-hydroxypropyl)-2-propan-2-ylidene-1-benzofuran-3-one
Synonyms:  
Molecular Formula:   C15H18O4
Standard InCHIKey:  FYUKKVDWTSHXKN-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H18O4/c1-8(2)14-13(18)11-5-4-10(6-9(3)17)12(7-16)15(11)19-14/h4-5,9,16-17H,6-7H2,1-3H3
Canonical SMILES:  OCc1c(ccc2c1OC(=C(C)C)C2=O)CC(O)C
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
NPO27058 Aspergillus ustus Species Aspergillaceae Eukaryota PMID[19769341]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT116 Cell Line HL-60 Homo sapiens IC50 = 130 nM 16038548
NPT81 Cell Line A549 Homo sapiens IC50 > 100000 nM 19928902
NPT116 Cell Line HL-60 Homo sapiens IC50 > 100000 nM 20627740

  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 NPC469385 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
0.9645 High Similarity NPC469425
0.9514 High Similarity NPC175617
0.9448 High Similarity NPC471349
0.9448 High Similarity NPC471347
0.9065 High Similarity NPC217914
0.9041 High Similarity NPC219560
0.9034 High Similarity NPC471346
0.898 High Similarity NPC228906
0.898 High Similarity NPC471348
0.898 High Similarity NPC469416
0.8881 High Similarity NPC477537
0.8824 High Similarity NPC313368
0.875 High Similarity NPC477535
0.8741 High Similarity NPC98395
0.8707 High Similarity NPC474630
0.8681 High Similarity NPC477408
0.8639 High Similarity NPC477409
0.8621 High Similarity NPC37206
0.8599 High Similarity NPC316262
0.8599 High Similarity NPC314653
0.8591 High Similarity NPC71055
0.8571 High Similarity NPC104380
0.8571 High Similarity NPC217602
0.8571 High Similarity NPC473282
0.8552 High Similarity NPC268691
0.8542 High Similarity NPC477534
0.8526 High Similarity NPC472780
0.8526 High Similarity NPC472783
0.8526 High Similarity NPC269117
0.8523 High Similarity NPC470357
0.8503 High Similarity NPC171870
0.85 High Similarity NPC313717
0.85 High Similarity NPC315306
0.8497 Intermediate Similarity NPC193200
0.8493 Intermediate Similarity NPC137009
0.8487 Intermediate Similarity NPC72958
0.8487 Intermediate Similarity NPC232645
0.8477 Intermediate Similarity NPC226578
0.8467 Intermediate Similarity NPC8817
0.8467 Intermediate Similarity NPC137296
0.8462 Intermediate Similarity NPC472782
0.8462 Intermediate Similarity NPC472781
0.8456 Intermediate Similarity NPC28632
0.8452 Intermediate Similarity NPC212967
0.8452 Intermediate Similarity NPC164110
0.8452 Intermediate Similarity NPC246647
0.8452 Intermediate Similarity NPC294300
0.8452 Intermediate Similarity NPC96342
0.8452 Intermediate Similarity NPC476404
0.8452 Intermediate Similarity NPC317900
0.8435 Intermediate Similarity NPC283292
0.8431 Intermediate Similarity NPC275878
0.8431 Intermediate Similarity NPC40356
0.8431 Intermediate Similarity NPC87708
0.8431 Intermediate Similarity NPC154683
0.8431 Intermediate Similarity NPC271681
0.8421 Intermediate Similarity NPC202595
0.8411 Intermediate Similarity NPC5537
0.8411 Intermediate Similarity NPC73411
0.8411 Intermediate Similarity NPC215711
0.84 Intermediate Similarity NPC300540
0.8392 Intermediate Similarity NPC477536
0.8389 Intermediate Similarity NPC471451
0.8389 Intermediate Similarity NPC475813
0.8387 Intermediate Similarity NPC180924
0.838 Intermediate Similarity NPC324488
0.8378 Intermediate Similarity NPC329493
0.8378 Intermediate Similarity NPC96692
0.8377 Intermediate Similarity NPC290927
0.8377 Intermediate Similarity NPC135522
0.8377 Intermediate Similarity NPC210942
0.8377 Intermediate Similarity NPC169990
0.8377 Intermediate Similarity NPC301233
0.8377 Intermediate Similarity NPC84721
0.8369 Intermediate Similarity NPC939
0.8366 Intermediate Similarity NPC478148
0.8366 Intermediate Similarity NPC149526
0.8366 Intermediate Similarity NPC470569
0.8366 Intermediate Similarity NPC258249
0.8366 Intermediate Similarity NPC471613
0.8366 Intermediate Similarity NPC474417
0.8365 Intermediate Similarity NPC472784
0.8355 Intermediate Similarity NPC97028
0.8355 Intermediate Similarity NPC158338
0.8355 Intermediate Similarity NPC97029
0.8355 Intermediate Similarity NPC100985
0.8355 Intermediate Similarity NPC288036
0.8355 Intermediate Similarity NPC65589
0.8345 Intermediate Similarity NPC232996
0.8344 Intermediate Similarity NPC210320
0.8344 Intermediate Similarity NPC22005
0.8344 Intermediate Similarity NPC470810
0.8344 Intermediate Similarity NPC7943
0.8344 Intermediate Similarity NPC284495
0.8344 Intermediate Similarity NPC123202
0.8333 Intermediate Similarity NPC281137
0.8333 Intermediate Similarity NPC282390
0.8333 Intermediate Similarity NPC247743
0.8333 Intermediate Similarity NPC75694
0.8323 Intermediate Similarity NPC148938
0.8322 Intermediate Similarity NPC84266
0.8322 Intermediate Similarity NPC309430
0.8322 Intermediate Similarity NPC470160
0.8322 Intermediate Similarity NPC162476
0.8322 Intermediate Similarity NPC130206
0.8313 Intermediate Similarity NPC191012
0.8312 Intermediate Similarity NPC253904
0.8312 Intermediate Similarity NPC473967
0.8312 Intermediate Similarity NPC321363
0.8312 Intermediate Similarity NPC273483
0.8311 Intermediate Similarity NPC149533
0.8302 Intermediate Similarity NPC100849
0.8301 Intermediate Similarity NPC61258
0.8301 Intermediate Similarity NPC290954
0.8301 Intermediate Similarity NPC158866
0.8301 Intermediate Similarity NPC470568
0.8301 Intermediate Similarity NPC255641
0.8299 Intermediate Similarity NPC1268
0.8291 Intermediate Similarity NPC117985
0.8291 Intermediate Similarity NPC24761
0.8289 Intermediate Similarity NPC27221
0.8289 Intermediate Similarity NPC7025
0.8289 Intermediate Similarity NPC256672
0.8289 Intermediate Similarity NPC168085
0.8289 Intermediate Similarity NPC37139
0.828 Intermediate Similarity NPC186113
0.8278 Intermediate Similarity NPC469758
0.8278 Intermediate Similarity NPC130176
0.8278 Intermediate Similarity NPC99454
0.8276 Intermediate Similarity NPC142027
0.8276 Intermediate Similarity NPC27407
0.8276 Intermediate Similarity NPC164136
0.8267 Intermediate Similarity NPC245482
0.8267 Intermediate Similarity NPC105381
0.8267 Intermediate Similarity NPC274085
0.8267 Intermediate Similarity NPC10302
0.8267 Intermediate Similarity NPC89664
0.8267 Intermediate Similarity NPC301751
0.8264 Intermediate Similarity NPC254603
0.8261 Intermediate Similarity NPC150131
0.8258 Intermediate Similarity NPC189130
0.8258 Intermediate Similarity NPC329844
0.8258 Intermediate Similarity NPC235333
0.8255 Intermediate Similarity NPC182255
0.8255 Intermediate Similarity NPC474385
0.8255 Intermediate Similarity NPC94076
0.8252 Intermediate Similarity NPC205360
0.8247 Intermediate Similarity NPC230848
0.8247 Intermediate Similarity NPC472423
0.8247 Intermediate Similarity NPC474772
0.8247 Intermediate Similarity NPC474744
0.8247 Intermediate Similarity NPC39819
0.8243 Intermediate Similarity NPC139554
0.8243 Intermediate Similarity NPC165172
0.8239 Intermediate Similarity NPC216752
0.8239 Intermediate Similarity NPC475106
0.8235 Intermediate Similarity NPC269420
0.8235 Intermediate Similarity NPC65775
0.8235 Intermediate Similarity NPC198927
0.8235 Intermediate Similarity NPC10027
0.8235 Intermediate Similarity NPC233267
0.8235 Intermediate Similarity NPC317492
0.8235 Intermediate Similarity NPC70764
0.8235 Intermediate Similarity NPC39929
0.8235 Intermediate Similarity NPC296030
0.8235 Intermediate Similarity NPC470461
0.8235 Intermediate Similarity NPC291049
0.8228 Intermediate Similarity NPC472961
0.8228 Intermediate Similarity NPC472962
0.8228 Intermediate Similarity NPC472618
0.8227 Intermediate Similarity NPC469386
0.8224 Intermediate Similarity NPC252208
0.8224 Intermediate Similarity NPC202494
0.8224 Intermediate Similarity NPC14098
0.8224 Intermediate Similarity NPC66991
0.8224 Intermediate Similarity NPC478163
0.8224 Intermediate Similarity NPC472036
0.8224 Intermediate Similarity NPC259632
0.8219 Intermediate Similarity NPC84699
0.8219 Intermediate Similarity NPC141934
0.8217 Intermediate Similarity NPC201127
0.8212 Intermediate Similarity NPC478019
0.8212 Intermediate Similarity NPC472034
0.8212 Intermediate Similarity NPC470857
0.8212 Intermediate Similarity NPC297788
0.8212 Intermediate Similarity NPC87486
0.8212 Intermediate Similarity NPC469764
0.8212 Intermediate Similarity NPC124780
0.821 Intermediate Similarity NPC473096
0.821 Intermediate Similarity NPC473095
0.8205 Intermediate Similarity NPC478159
0.8205 Intermediate Similarity NPC326910
0.8205 Intermediate Similarity NPC213936
0.8205 Intermediate Similarity NPC478161
0.8205 Intermediate Similarity NPC237560
0.8205 Intermediate Similarity NPC99381
0.8205 Intermediate Similarity NPC297531
0.82 Intermediate Similarity NPC469885
0.82 Intermediate Similarity NPC1534
0.82 Intermediate Similarity NPC469542

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC469385 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
0.8333 Intermediate Similarity NPD2532 Approved
0.8333 Intermediate Similarity NPD2533 Approved
0.8333 Intermediate Similarity NPD2534 Approved
0.8141 Intermediate Similarity NPD7819 Suspended
0.8117 Intermediate Similarity NPD3226 Approved
0.8108 Intermediate Similarity NPD2346 Discontinued
0.8092 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8056 Intermediate Similarity NPD1699 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD3882 Suspended
0.8025 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7987 Intermediate Similarity NPD7075 Discontinued
0.7962 Intermediate Similarity NPD6801 Discontinued
0.795 Intermediate Similarity NPD6959 Discontinued
0.7949 Intermediate Similarity NPD6599 Discontinued
0.7933 Intermediate Similarity NPD1549 Phase 2
0.7911 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7885 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7867 Intermediate Similarity NPD1471 Phase 3
0.7867 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7867 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7838 Intermediate Similarity NPD1607 Approved
0.7815 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7808 Intermediate Similarity NPD411 Approved
0.78 Intermediate Similarity NPD1551 Phase 2
0.78 Intermediate Similarity NPD2796 Approved
0.7792 Intermediate Similarity NPD6799 Approved
0.7763 Intermediate Similarity NPD2800 Approved
0.7756 Intermediate Similarity NPD5403 Approved
0.775 Intermediate Similarity NPD5402 Approved
0.775 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7746 Intermediate Similarity NPD9717 Approved
0.7742 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7738 Intermediate Similarity NPD6559 Discontinued
0.7733 Intermediate Similarity NPD1510 Phase 2
0.7722 Intermediate Similarity NPD4380 Phase 2
0.7716 Intermediate Similarity NPD919 Approved
0.7712 Intermediate Similarity NPD4628 Phase 3
0.7703 Intermediate Similarity NPD1240 Approved
0.7682 Intermediate Similarity NPD2935 Discontinued
0.7673 Intermediate Similarity NPD7411 Suspended
0.7669 Intermediate Similarity NPD5494 Approved
0.7665 Intermediate Similarity NPD5844 Phase 1
0.7647 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7644 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD6005 Phase 3
0.7632 Intermediate Similarity NPD6004 Phase 3
0.7632 Intermediate Similarity NPD6003 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD6006 Clinical (unspecified phase)
0.7632 Intermediate Similarity NPD6002 Phase 3
0.7628 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7628 Intermediate Similarity NPD5401 Approved
0.7625 Intermediate Similarity NPD1934 Approved
0.7622 Intermediate Similarity NPD1247 Approved
0.7616 Intermediate Similarity NPD2799 Discontinued
0.759 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.759 Intermediate Similarity NPD6166 Phase 2
0.759 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.758 Intermediate Similarity NPD1512 Approved
0.7576 Intermediate Similarity NPD5710 Approved
0.7576 Intermediate Similarity NPD5711 Approved
0.7568 Intermediate Similarity NPD2313 Discontinued
0.756 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.7552 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7544 Intermediate Similarity NPD8312 Approved
0.7544 Intermediate Similarity NPD8313 Approved
0.7533 Intermediate Similarity NPD447 Suspended
0.7532 Intermediate Similarity NPD920 Approved
0.7532 Intermediate Similarity NPD1243 Approved
0.7531 Intermediate Similarity NPD3817 Phase 2
0.7516 Intermediate Similarity NPD2344 Approved
0.75 Intermediate Similarity NPD3818 Discontinued
0.75 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD7768 Phase 2
0.7484 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.7484 Intermediate Similarity NPD3750 Approved
0.747 Intermediate Similarity NPD6232 Discontinued
0.7466 Intermediate Similarity NPD1470 Approved
0.7466 Intermediate Similarity NPD1203 Approved
0.7452 Intermediate Similarity NPD1511 Approved
0.7451 Intermediate Similarity NPD6099 Approved
0.7451 Intermediate Similarity NPD6100 Approved
0.744 Intermediate Similarity NPD7473 Discontinued
0.7439 Intermediate Similarity NPD3749 Approved
0.7439 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7432 Intermediate Similarity NPD6832 Phase 2
0.7431 Intermediate Similarity NPD1201 Approved
0.7413 Intermediate Similarity NPD1778 Approved
0.7405 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7403 Intermediate Similarity NPD5762 Approved
0.7403 Intermediate Similarity NPD5763 Approved
0.7403 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7386 Intermediate Similarity NPD7033 Discontinued
0.7381 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD6797 Phase 2
0.7362 Intermediate Similarity NPD2801 Approved
0.7362 Intermediate Similarity NPD5760 Phase 2
0.7362 Intermediate Similarity NPD5761 Phase 2
0.7358 Intermediate Similarity NPD6273 Approved
0.7338 Intermediate Similarity NPD5405 Approved
0.7338 Intermediate Similarity NPD5406 Approved
0.7338 Intermediate Similarity NPD5408 Approved
0.7338 Intermediate Similarity NPD5404 Approved
0.7326 Intermediate Similarity NPD7251 Discontinued
0.7325 Intermediate Similarity NPD2309 Approved
0.7321 Intermediate Similarity NPD3926 Phase 2
0.7314 Intermediate Similarity NPD8434 Phase 2
0.7314 Intermediate Similarity NPD8150 Discontinued
0.7303 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7297 Intermediate Similarity NPD1019 Discontinued
0.7297 Intermediate Similarity NPD2798 Approved
0.7294 Intermediate Similarity NPD3751 Discontinued
0.7294 Intermediate Similarity NPD7177 Discontinued
0.7292 Intermediate Similarity NPD4626 Approved
0.7283 Intermediate Similarity NPD4419 Clinical (unspecified phase)
0.7283 Intermediate Similarity NPD7808 Phase 3
0.7279 Intermediate Similarity NPD6696 Suspended
0.7273 Intermediate Similarity NPD3748 Approved
0.7273 Intermediate Similarity NPD4308 Phase 3
0.7267 Intermediate Similarity NPD4625 Phase 3
0.726 Intermediate Similarity NPD1608 Approved
0.7255 Intermediate Similarity NPD6651 Approved
0.7254 Intermediate Similarity NPD9493 Approved
0.7253 Intermediate Similarity NPD6777 Approved
0.7253 Intermediate Similarity NPD6780 Approved
0.7253 Intermediate Similarity NPD6781 Approved
0.7253 Intermediate Similarity NPD6776 Approved
0.7253 Intermediate Similarity NPD6778 Approved
0.7253 Intermediate Similarity NPD6779 Approved
0.7253 Intermediate Similarity NPD6782 Approved
0.7237 Intermediate Similarity NPD4060 Phase 1
0.7228 Intermediate Similarity NPD7435 Discontinued
0.7222 Intermediate Similarity NPD1651 Approved
0.7222 Intermediate Similarity NPD5691 Approved
0.7219 Intermediate Similarity NPD3268 Approved
0.7209 Intermediate Similarity NPD7074 Phase 3
0.7193 Intermediate Similarity NPD7893 Clinical (unspecified phase)
0.719 Intermediate Similarity NPD6355 Discontinued
0.7186 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7184 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7162 Intermediate Similarity NPD1283 Approved
0.7161 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.716 Intermediate Similarity NPD3787 Discontinued
0.7152 Intermediate Similarity NPD7003 Approved
0.7151 Intermediate Similarity NPD7054 Approved
0.7135 Intermediate Similarity NPD7696 Phase 3
0.7135 Intermediate Similarity NPD7698 Approved
0.7135 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7135 Intermediate Similarity NPD7697 Approved
0.7133 Intermediate Similarity NPD405 Clinical (unspecified phase)
0.7125 Intermediate Similarity NPD7390 Discontinued
0.7114 Intermediate Similarity NPD2797 Approved
0.711 Intermediate Similarity NPD7472 Approved
0.7105 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7105 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7097 Intermediate Similarity NPD7870 Phase 2
0.7097 Intermediate Similarity NPD7871 Phase 2
0.7093 Intermediate Similarity NPD2163 Approved
0.7091 Intermediate Similarity NPD6844 Discontinued
0.7089 Intermediate Similarity NPD5698 Clinical (unspecified phase)
0.7076 Intermediate Similarity NPD4575 Clinical (unspecified phase)
0.7072 Intermediate Similarity NPD6534 Approved
0.7072 Intermediate Similarity NPD6535 Approved
0.7069 Intermediate Similarity NPD5953 Discontinued
0.7067 Intermediate Similarity NPD6917 Clinical (unspecified phase)
0.7066 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7055 Intermediate Similarity NPD17 Approved
0.7042 Intermediate Similarity NPD1241 Discontinued
0.7034 Intermediate Similarity NPD9545 Approved
0.7027 Intermediate Similarity NPD3972 Approved
0.7025 Intermediate Similarity NPD2424 Discontinued
0.7018 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7013 Intermediate Similarity NPD4307 Phase 2
0.7012 Intermediate Similarity NPD7458 Discontinued
0.7012 Intermediate Similarity NPD2651 Approved
0.7012 Intermediate Similarity NPD2649 Approved
0.7011 Intermediate Similarity NPD1729 Discontinued
0.7006 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD7874 Approved
0.7 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.6993 Remote Similarity NPD6798 Discontinued
0.6993 Remote Similarity NPD3764 Approved
0.6988 Remote Similarity NPD37 Approved
0.6984 Remote Similarity NPD7701 Phase 2
0.6981 Remote Similarity NPD2654 Approved
0.698 Remote Similarity NPD4749 Approved
0.6975 Remote Similarity NPD4662 Approved
0.6975 Remote Similarity NPD4661 Approved
0.6971 Remote Similarity NPD7993 Clinical (unspecified phase)
0.6968 Remote Similarity NPD5124 Phase 1
0.6968 Remote Similarity NPD5123 Clinical (unspecified phase)
0.6964 Remote Similarity NPD4965 Approved
0.6964 Remote Similarity NPD4967 Phase 2
0.6964 Remote Similarity NPD4966 Approved
0.6959 Remote Similarity NPD7229 Phase 3
0.6959 Remote Similarity NPD1281 Approved
0.6957 Remote Similarity NPD7699 Phase 2
0.6957 Remote Similarity NPD7700 Phase 2
0.6954 Remote Similarity NPD5647 Approved

Structure

External Identifiers

PubChem CID   44557644
ChEMBL   CHEMBL1077457
ZINC  

Physicochemical Properties

Molecular Weight:  262.12
ALogP:  -0.1542
MLogP:  2.67
XLogP:  1.516
# Rotatable Bonds:  8
Polar Surface Area:  66.76
# H-Bond Aceptor:  3
# H-Bond Donor:  2
# Rings:  2
# Heavy Atoms:  19

Download Data

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Structure MOL file  
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Biological Activities  
Similar NPs/Drugs