Natural Product: NPC309845

Natural Product ID:  NPC309845
Common Name:   4-Amino-6-Hydroxyquinoline-8-Carboxylic Acid
IUPAC Name:   4-amino-6-hydroxyquinoline-8-carboxylic acid
Synonyms:  
Molecular Formula:   C10H8N2O3
Standard InCHIKey:  XIIQRVUIEJEQQV-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H8N2O3/c11-8-1-2-12-9-6(8)3-5(13)4-7(9)10(14)15/h1-4,13H,(H2,11,12)(H,14,15)
Canonical SMILES:  Oc1cc(C(=O)O)c2c(c1)c(N)ccn2
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
NPO2192 Cortinarius subtortus Species Cortinariaceae Eukaryota fruiting bodies PMID[18447384]

  Biological Activity

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT1 Others Radical scavenging activity Activity = 12 % 18183025

  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 NPC309845 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
0.9355 High Similarity NPC90229
0.8483 Intermediate Similarity NPC477112
0.8426 Intermediate Similarity NPC213308
0.8269 Intermediate Similarity NPC74360
0.8265 Intermediate Similarity NPC146724
0.8244 Intermediate Similarity NPC219087
0.8241 Intermediate Similarity NPC315491
0.8241 Intermediate Similarity NPC45459
0.823 Intermediate Similarity NPC276657
0.8227 Intermediate Similarity NPC171787
0.819 Intermediate Similarity NPC178858
0.8182 Intermediate Similarity NPC156704
0.8177 Intermediate Similarity NPC193238
0.8095 Intermediate Similarity NPC303225
0.8086 Intermediate Similarity NPC469727
0.8081 Intermediate Similarity NPC276517
0.801 Intermediate Similarity NPC280714
0.8 Intermediate Similarity NPC88008
0.8 Intermediate Similarity NPC270918
0.7991 Intermediate Similarity NPC477549
0.799 Intermediate Similarity NPC237740
0.797 Intermediate Similarity NPC83111
0.7959 Intermediate Similarity NPC278434
0.7941 Intermediate Similarity NPC476098
0.7936 Intermediate Similarity NPC207686
0.7913 Intermediate Similarity NPC183777
0.7876 Intermediate Similarity NPC164340
0.7867 Intermediate Similarity NPC469928
0.7817 Intermediate Similarity NPC194040
0.7789 Intermediate Similarity NPC144381
0.7766 Intermediate Similarity NPC314002
0.7755 Intermediate Similarity NPC220765
0.7746 Intermediate Similarity NPC27041
0.7718 Intermediate Similarity NPC211813
0.7716 Intermediate Similarity NPC204717
0.7716 Intermediate Similarity NPC207851
0.7713 Intermediate Similarity NPC15801
0.7703 Intermediate Similarity NPC477111
0.7703 Intermediate Similarity NPC97902
0.77 Intermediate Similarity NPC477110
0.7696 Intermediate Similarity NPC474916
0.7692 Intermediate Similarity NPC477113
0.7682 Intermediate Similarity NPC74619
0.7678 Intermediate Similarity NPC294375
0.7656 Intermediate Similarity NPC53344
0.7653 Intermediate Similarity NPC118228
0.765 Intermediate Similarity NPC44354
0.7641 Intermediate Similarity NPC184964
0.7638 Intermediate Similarity NPC171171
0.7635 Intermediate Similarity NPC202812
0.7633 Intermediate Similarity NPC57398
0.7628 Intermediate Similarity NPC264285
0.7624 Intermediate Similarity NPC99666
0.7623 Intermediate Similarity NPC182222
0.7619 Intermediate Similarity NPC39679
0.7608 Intermediate Similarity NPC300156
0.7594 Intermediate Similarity NPC9894
0.7591 Intermediate Similarity NPC74575
0.7588 Intermediate Similarity NPC208522
0.7574 Intermediate Similarity NPC138370
0.7571 Intermediate Similarity NPC283117
0.7571 Intermediate Similarity NPC321428
0.7561 Intermediate Similarity NPC77555
0.7547 Intermediate Similarity NPC470020
0.7545 Intermediate Similarity NPC470018
0.7537 Intermediate Similarity NPC56170
0.7534 Intermediate Similarity NPC229893
0.7524 Intermediate Similarity NPC306376
0.7523 Intermediate Similarity NPC60621
0.7522 Intermediate Similarity NPC161801
0.7512 Intermediate Similarity NPC46580
0.75 Intermediate Similarity NPC45850
0.75 Intermediate Similarity NPC282103
0.75 Intermediate Similarity NPC325297
0.75 Intermediate Similarity NPC230403
0.7477 Intermediate Similarity NPC246381
0.7477 Intermediate Similarity NPC110182
0.7476 Intermediate Similarity NPC475070
0.7474 Intermediate Similarity NPC113812
0.7474 Intermediate Similarity NPC473764
0.7474 Intermediate Similarity NPC314940
0.7465 Intermediate Similarity NPC184408
0.7464 Intermediate Similarity NPC328596
0.7464 Intermediate Similarity NPC328318
0.7462 Intermediate Similarity NPC111275
0.7461 Intermediate Similarity NPC41717
0.7455 Intermediate Similarity NPC49547
0.7455 Intermediate Similarity NPC322482
0.7454 Intermediate Similarity NPC330009
0.7438 Intermediate Similarity NPC154339
0.7436 Intermediate Similarity NPC273532
0.743 Intermediate Similarity NPC87413
0.7429 Intermediate Similarity NPC134848
0.7426 Intermediate Similarity NPC206186
0.7424 Intermediate Similarity NPC295452
0.7424 Intermediate Similarity NPC171393
0.7415 Intermediate Similarity NPC329541
0.7411 Intermediate Similarity NPC260434
0.7409 Intermediate Similarity NPC16352
0.7397 Intermediate Similarity NPC472099
0.7389 Intermediate Similarity NPC183805
0.7385 Intermediate Similarity NPC96321
0.7383 Intermediate Similarity NPC5145
0.7379 Intermediate Similarity NPC326634
0.7376 Intermediate Similarity NPC122436
0.7376 Intermediate Similarity NPC51388
0.7373 Intermediate Similarity NPC3207
0.7371 Intermediate Similarity NPC210828
0.7371 Intermediate Similarity NPC86834
0.7361 Intermediate Similarity NPC317752
0.7358 Intermediate Similarity NPC317373
0.7358 Intermediate Similarity NPC45190
0.7354 Intermediate Similarity NPC478078
0.7349 Intermediate Similarity NPC82370
0.7347 Intermediate Similarity NPC252590
0.7346 Intermediate Similarity NPC200836
0.7346 Intermediate Similarity NPC53144
0.7344 Intermediate Similarity NPC322644
0.7333 Intermediate Similarity NPC471944
0.733 Intermediate Similarity NPC267343
0.7327 Intermediate Similarity NPC295158
0.7323 Intermediate Similarity NPC84347
0.7315 Intermediate Similarity NPC318299
0.7311 Intermediate Similarity NPC216369
0.7311 Intermediate Similarity NPC327592
0.7308 Intermediate Similarity NPC473814
0.7308 Intermediate Similarity NPC74153
0.7308 Intermediate Similarity NPC78767
0.7304 Intermediate Similarity NPC32771
0.7301 Intermediate Similarity NPC279189
0.7301 Intermediate Similarity NPC200553
0.7294 Intermediate Similarity NPC476161
0.7294 Intermediate Similarity NPC322064
0.7291 Intermediate Similarity NPC62749
0.729 Intermediate Similarity NPC266249
0.729 Intermediate Similarity NPC18348
0.7286 Intermediate Similarity NPC219848
0.7281 Intermediate Similarity NPC39500
0.7277 Intermediate Similarity NPC175602
0.7273 Intermediate Similarity NPC192315
0.7269 Intermediate Similarity NPC23294
0.7264 Intermediate Similarity NPC317572
0.7261 Intermediate Similarity NPC132385
0.726 Intermediate Similarity NPC251090
0.726 Intermediate Similarity NPC293151
0.7257 Intermediate Similarity NPC474701
0.7252 Intermediate Similarity NPC220851
0.725 Intermediate Similarity NPC256268
0.725 Intermediate Similarity NPC55772
0.725 Intermediate Similarity NPC88363
0.7246 Intermediate Similarity NPC307963
0.7246 Intermediate Similarity NPC473821
0.7245 Intermediate Similarity NPC78020
0.7243 Intermediate Similarity NPC4687
0.7241 Intermediate Similarity NPC142385
0.7238 Intermediate Similarity NPC476167
0.7237 Intermediate Similarity NPC253675
0.7235 Intermediate Similarity NPC118940
0.7235 Intermediate Similarity NPC472098
0.7232 Intermediate Similarity NPC24370
0.7232 Intermediate Similarity NPC319232
0.7231 Intermediate Similarity NPC471178
0.723 Intermediate Similarity NPC472259
0.7228 Intermediate Similarity NPC243058
0.7225 Intermediate Similarity NPC141454
0.7225 Intermediate Similarity NPC475720
0.7225 Intermediate Similarity NPC474192
0.7222 Intermediate Similarity NPC123839
0.7222 Intermediate Similarity NPC303951
0.722 Intermediate Similarity NPC221873
0.7219 Intermediate Similarity NPC167400
0.7217 Intermediate Similarity NPC41679
0.7212 Intermediate Similarity NPC93390
0.7206 Intermediate Similarity NPC315555
0.7205 Intermediate Similarity NPC162002
0.7202 Intermediate Similarity NPC250448
0.72 Intermediate Similarity NPC157931
0.72 Intermediate Similarity NPC96890
0.7195 Intermediate Similarity NPC269270
0.7192 Intermediate Similarity NPC203635
0.7191 Intermediate Similarity NPC270515
0.7191 Intermediate Similarity NPC63971
0.7191 Intermediate Similarity NPC91868
0.719 Intermediate Similarity NPC131887
0.7186 Intermediate Similarity NPC139763
0.7186 Intermediate Similarity NPC110500
0.7186 Intermediate Similarity NPC149155
0.7186 Intermediate Similarity NPC203468
0.7183 Intermediate Similarity NPC165599
0.7179 Intermediate Similarity NPC97367
0.7177 Intermediate Similarity NPC242209
0.7176 Intermediate Similarity NPC61038
0.7174 Intermediate Similarity NPC470022
0.7174 Intermediate Similarity NPC184225
0.7172 Intermediate Similarity NPC249614
0.7168 Intermediate Similarity NPC311906
0.7163 Intermediate Similarity NPC244741
0.7162 Intermediate Similarity NPC174760
0.7162 Intermediate Similarity NPC14686
0.7162 Intermediate Similarity NPC174489

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC309845 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
0.8241 Intermediate Similarity NPD484 Approved
0.7962 Intermediate Similarity NPD4429 Discontinued
0.7917 Intermediate Similarity NPD4845 Discontinued
0.7857 Intermediate Similarity NPD3794 Approved
0.7857 Intermediate Similarity NPD3795 Approved
0.7816 Intermediate Similarity NPD5901 Discontinued
0.7811 Intermediate Similarity NPD5975 Clinical (unspecified phase)
0.7763 Intermediate Similarity NPD5022 Discontinued
0.7738 Intermediate Similarity NPD5040 Clinical (unspecified phase)
0.7688 Intermediate Similarity NPD4948 Discontinued
0.7602 Intermediate Similarity NPD5801 Clinical (unspecified phase)
0.7594 Intermediate Similarity NPD5416 Discontinued
0.7574 Intermediate Similarity NPD2336 Approved
0.7512 Intermediate Similarity NPD2121 Clinical (unspecified phase)
0.7511 Intermediate Similarity NPD5483 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD5575 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD9695 Approved
0.7453 Intermediate Similarity NPD2509 Approved
0.7453 Intermediate Similarity NPD2510 Approved
0.7435 Intermediate Similarity NPD3959 Phase 2
0.7435 Intermediate Similarity NPD3962 Phase 2
0.743 Intermediate Similarity NPD5475 Discontinued
0.7427 Intermediate Similarity NPD2307 Discontinued
0.7415 Intermediate Similarity NPD8091 Phase 3
0.7407 Intermediate Similarity NPD5417 Clinical (unspecified phase)
0.7397 Intermediate Similarity NPD3280 Approved
0.7397 Intermediate Similarity NPD6242 Discontinued
0.7393 Intermediate Similarity NPD6987 Phase 1
0.7361 Intermediate Similarity NPD3243 Approved
0.7311 Intermediate Similarity NPD3947 Discontinued
0.7311 Intermediate Similarity NPD6323 Clinical (unspecified phase)
0.7308 Intermediate Similarity NPD3986 Discontinued
0.7302 Intermediate Similarity NPD648 Clinical (unspecified phase)
0.7299 Intermediate Similarity NPD3928 Approved
0.7299 Intermediate Similarity NPD3931 Approved
0.7294 Intermediate Similarity NPD3394 Approved
0.7294 Intermediate Similarity NPD3389 Approved
0.7294 Intermediate Similarity NPD3393 Approved
0.729 Intermediate Similarity NPD2916 Discontinued
0.7273 Intermediate Similarity NPD9690 Approved
0.7265 Intermediate Similarity NPD7586 Clinical (unspecified phase)
0.7254 Intermediate Similarity NPD112 Approved
0.7254 Intermediate Similarity NPD9705 Discontinued
0.7246 Intermediate Similarity NPD1173 Approved
0.7246 Intermediate Similarity NPD1038 Approved
0.7235 Intermediate Similarity NPD7069 Discontinued
0.7232 Intermediate Similarity NPD7603 Discontinued
0.7227 Intermediate Similarity NPD3354 Phase 2
0.7225 Intermediate Similarity NPD3960 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD750 Phase 2
0.7219 Intermediate Similarity NPD9074 Approved
0.7219 Intermediate Similarity NPD9075 Approved
0.7215 Intermediate Similarity NPD4926 Clinical (unspecified phase)
0.7205 Intermediate Similarity NPD3006 Discontinued
0.7195 Intermediate Similarity NPD7404 Approved
0.7186 Intermediate Similarity NPD482 Approved
0.7186 Intermediate Similarity NPD2921 Clinical (unspecified phase)
0.7169 Intermediate Similarity NPD7538 Clinical (unspecified phase)
0.7161 Intermediate Similarity NPD3809 Discontinued
0.7157 Intermediate Similarity NPD6344 Clinical (unspecified phase)
0.715 Intermediate Similarity NPD749 Clinical (unspecified phase)
0.7149 Intermediate Similarity NPD7395 Discontinued
0.7124 Intermediate Similarity NPD1483 Discontinued
0.7123 Intermediate Similarity NPD1740 Approved
0.7123 Intermediate Similarity NPD1739 Approved
0.7116 Intermediate Similarity NPD3932 Clinical (unspecified phase)
0.7109 Intermediate Similarity NPD4987 Clinical (unspecified phase)
0.7106 Intermediate Similarity NPD5488 Discontinued
0.7094 Intermediate Similarity NPD3178 Discontinued
0.7091 Intermediate Similarity NPD4897 Phase 2
0.7089 Intermediate Similarity NPD5482 Discontinued
0.7083 Intermediate Similarity NPD3930 Clinical (unspecified phase)
0.7082 Intermediate Similarity NPD6790 Phase 1
0.7081 Intermediate Similarity NPD1304 Clinical (unspecified phase)
0.7079 Intermediate Similarity NPD5398 Clinical (unspecified phase)
0.7078 Intermediate Similarity NPD6657 Clinical (unspecified phase)
0.7075 Intermediate Similarity NPD6999 Discontinued
0.7075 Intermediate Similarity NPD7000 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD944 Approved
0.707 Intermediate Similarity NPD4795 Phase 2
0.707 Intermediate Similarity NPD6138 Clinical (unspecified phase)
0.707 Intermediate Similarity NPD5426 Phase 3
0.7062 Intermediate Similarity NPD7948 Phase 1
0.7059 Intermediate Similarity NPD2092 Phase 2
0.7059 Intermediate Similarity NPD2095 Phase 2
0.7059 Intermediate Similarity NPD5728 Clinical (unspecified phase)
0.7059 Intermediate Similarity NPD2094 Phase 2
0.7059 Intermediate Similarity NPD6803 Clinical (unspecified phase)
0.7056 Intermediate Similarity NPD926 Approved
0.7056 Intermediate Similarity NPD5469 Phase 3
0.7056 Intermediate Similarity NPD925 Approved
0.7051 Intermediate Similarity NPD6376 Discontinued
0.7043 Intermediate Similarity NPD4373 Phase 2
0.7042 Intermediate Similarity NPD4396 Clinical (unspecified phase)
0.704 Intermediate Similarity NPD3258 Approved
0.7037 Intermediate Similarity NPD7010 Phase 3
0.7024 Intermediate Similarity NPD2096 Phase 2
0.7024 Intermediate Similarity NPD2091 Phase 2
0.702 Intermediate Similarity NPD424 Approved
0.702 Intermediate Similarity NPD425 Approved
0.7019 Intermediate Similarity NPD1213 Phase 3
0.7018 Intermediate Similarity NPD2761 Approved
0.7005 Intermediate Similarity NPD107 Approved
0.7 Intermediate Similarity NPD5151 Clinical (unspecified phase)
0.7 Intermediate Similarity NPD3330 Phase 1
0.7 Intermediate Similarity NPD485 Clinical (unspecified phase)
0.6996 Remote Similarity NPD6531 Approved
0.6996 Remote Similarity NPD2011 Clinical (unspecified phase)
0.6996 Remote Similarity NPD6530 Approved
0.6996 Remote Similarity NPD8405 Clinical (unspecified phase)
0.6991 Remote Similarity NPD3222 Phase 2
0.6991 Remote Similarity NPD4039 Approved
0.6991 Remote Similarity NPD4035 Approved
0.6991 Remote Similarity NPD4037 Approved
0.6991 Remote Similarity NPD4122 Approved
0.6991 Remote Similarity NPD4033 Approved
0.6991 Remote Similarity NPD32 Approved
0.6991 Remote Similarity NPD4038 Approved
0.6991 Remote Similarity NPD4034 Approved
0.6991 Remote Similarity NPD31 Approved
0.6991 Remote Similarity NPD4036 Approved
0.6987 Remote Similarity NPD4952 Phase 3
0.6982 Remote Similarity NPD7112 Discontinued
0.698 Remote Similarity NPD5100 Phase 3
0.6975 Remote Similarity NPD4558 Phase 2
0.6966 Remote Similarity NPD4561 Discontinued
0.6963 Remote Similarity NPD5497 Clinical (unspecified phase)
0.6963 Remote Similarity NPD8248 Clinical (unspecified phase)
0.6961 Remote Similarity NPD1291 Clinical (unspecified phase)
0.6961 Remote Similarity NPD9510 Approved
0.696 Remote Similarity NPD3925 Approved
0.696 Remote Similarity NPD7269 Clinical (unspecified phase)
0.6959 Remote Similarity NPD4862 Clinical (unspecified phase)
0.6955 Remote Similarity NPD6567 Clinical (unspecified phase)
0.6952 Remote Similarity NPD5505 Discontinued
0.6952 Remote Similarity NPD6665 Discontinued
0.6952 Remote Similarity NPD3404 Approved
0.695 Remote Similarity NPD1573 Approved
0.695 Remote Similarity NPD1575 Approved
0.6938 Remote Similarity NPD4081 Clinical (unspecified phase)
0.6937 Remote Similarity NPD3257 Approved
0.6933 Remote Similarity NPD6276 Discontinued
0.6931 Remote Similarity NPD5065 Approved
0.6927 Remote Similarity NPD1783 Clinical (unspecified phase)
0.6927 Remote Similarity NPD6838 Clinical (unspecified phase)
0.6923 Remote Similarity NPD8096 Phase 3
0.6923 Remote Similarity NPD8097 Phase 3
0.6919 Remote Similarity NPD802 Phase 2
0.6919 Remote Similarity NPD1631 Approved
0.6919 Remote Similarity NPD5088 Discontinued
0.6916 Remote Similarity NPD2175 Phase 3
0.6916 Remote Similarity NPD2176 Approved
0.6916 Remote Similarity NPD2803 Discontinued
0.6916 Remote Similarity NPD2177 Approved
0.6912 Remote Similarity NPD8304 Clinical (unspecified phase)
0.6909 Remote Similarity NPD7998 Clinical (unspecified phase)
0.6906 Remote Similarity NPD5612 Discontinued
0.6903 Remote Similarity NPD5506 Approved
0.6903 Remote Similarity NPD5507 Approved
0.69 Remote Similarity NPD6292 Clinical (unspecified phase)
0.6898 Remote Similarity NPD5721 Clinical (unspecified phase)
0.6897 Remote Similarity NPD6494 Phase 2
0.6897 Remote Similarity NPD4850 Phase 1
0.6895 Remote Similarity NPD7666 Phase 3
0.6895 Remote Similarity NPD7665 Phase 2
0.6893 Remote Similarity NPD5522 Clinical (unspecified phase)
0.6881 Remote Similarity NPD6732 Clinical (unspecified phase)
0.6881 Remote Similarity NPD7001 Phase 3
0.6878 Remote Similarity NPD3779 Clinical (unspecified phase)
0.6872 Remote Similarity NPD6160 Clinical (unspecified phase)
0.6872 Remote Similarity NPD5937 Approved
0.6869 Remote Similarity NPD1685 Approved
0.6869 Remote Similarity NPD1684 Approved
0.6866 Remote Similarity NPD5513 Phase 2
0.6861 Remote Similarity NPD5293 Phase 2
0.6853 Remote Similarity NPD604 Clinical (unspecified phase)
0.6844 Remote Similarity NPD5632 Approved
0.6842 Remote Similarity NPD6753 Phase 1
0.6842 Remote Similarity NPD6752 Phase 1
0.6838 Remote Similarity NPD5891 Approved
0.6837 Remote Similarity NPD6661 Clinical (unspecified phase)
0.6837 Remote Similarity NPD6137 Clinical (unspecified phase)
0.6829 Remote Similarity NPD1620 Clinical (unspecified phase)
0.6826 Remote Similarity NPD6164 Phase 2
0.6826 Remote Similarity NPD6165 Phase 2
0.6826 Remote Similarity NPD3259 Approved
0.6822 Remote Similarity NPD2952 Discontinued
0.6816 Remote Similarity NPD2781 Approved
0.6816 Remote Similarity NPD2844 Phase 3
0.6816 Remote Similarity NPD2615 Phase 3
0.6816 Remote Similarity NPD2616 Phase 3
0.6809 Remote Similarity NPD2896 Discontinued
0.6809 Remote Similarity NPD203 Clinical (unspecified phase)
0.6808 Remote Similarity NPD4418 Discontinued
0.6806 Remote Similarity NPD2305 Discontinued
0.6805 Remote Similarity NPD6525 Clinical (unspecified phase)
0.6803 Remote Similarity NPD6458 Discontinued
0.6802 Remote Similarity NPD4417 Approved
0.6802 Remote Similarity NPD7927 Clinical (unspecified phase)
0.68 Remote Similarity NPD3326 Clinical (unspecified phase)

Structure

External Identifiers

PubChem CID   24896705
ChEMBL   CHEMBL451011
ZINC  

Physicochemical Properties

Molecular Weight:  204.05
ALogP:  -1.45
MLogP:  2.01
XLogP:  0.061
# Rotatable Bonds:  4
Polar Surface Area:  96.44
# H-Bond Aceptor:  4
# H-Bond Donor:  3
# Rings:  2
# Heavy Atoms:  15

Download Data

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