Natural Product: NPC237560

Natural Product ID:  NPC237560
Common Name:   Methyl (4R,4As)-4,8-Dihydroxy-6-Methyl-9-Oxo-4H-Xanthene-4A-Carboxylate
IUPAC Name:   methyl (4R,4aS)-4,8-dihydroxy-6-methyl-9-oxo-4H-xanthene-4a-carboxylate
Synonyms:  
Molecular Formula:   C16H14O6
Standard InCHIKey:  BVPTZDRKEDPTOX-WBMJQRKESA-N
Standard InCHI:  InChI=1S/C16H14O6/c1-8-6-10(17)13-11(7-8)22-16(15(20)21-2)9(14(13)19)4-3-5-12(16)18/h3-7,12,17-18H,1-2H3/t12-,16+/m1/s1
Canonical SMILES:  COC(=O)[C@@]12Oc3cc(C)cc(c3C(=O)C2=CC=C[C@H]1O)O
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
NPO4291 Laurencia brongniartii Species Rhodomelaceae Eukaryota UNPD*
NPO31059 Penicillium Genus Aspergillaceae Eukaryota PMID[9711252]
NPO31300.1 Emericella nidulans var. lata Varieties Aspergillaceae Eukaryota Chem. Pharm. Bull.,1994,42: 1720
NPO568 Peganum nigellastrum Species Nitrariaceae Eukaryota UNPD*

  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 = 140 nM 10509910
NPT111 Cell Line K562 Homo sapiens IC50 = 320 nM 10509910
NPT168 Cell Line P388 Mus musculus IC50 = 24 nM 10509910
NPT4451 Individual Protein DNA topoisomerase I Mus musculus IC50 = 172000 nM 10509910
NPT5376 Individual Protein DNA topoisomerase II Drosophila melanogaster IC50 = 2200 nM 10509910
NPT32 Organism Mus musculus Mus musculus Activity = 24 % 10509910

  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 NPC237560 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
0.9536 High Similarity NPC154341
0.9333 High Similarity NPC475717
0.9216 High Similarity NPC326910
0.92 High Similarity NPC228012
0.915 High Similarity NPC301233
0.9026 High Similarity NPC198236
0.902 High Similarity NPC39819
0.8961 High Similarity NPC275878
0.8961 High Similarity NPC321363
0.8961 High Similarity NPC253904
0.8947 High Similarity NPC191634
0.8874 High Similarity NPC469764
0.8839 High Similarity NPC281272
0.8816 High Similarity NPC469758
0.879 High Similarity NPC272550
0.879 High Similarity NPC472050
0.8784 High Similarity NPC287068
0.878 High Similarity NPC154986
0.8766 High Similarity NPC4423
0.8766 High Similarity NPC477941
0.8766 High Similarity NPC77325
0.8742 High Similarity NPC471744
0.8742 High Similarity NPC130955
0.8735 High Similarity NPC477682
0.8735 High Similarity NPC477683
0.8734 High Similarity NPC476930
0.8734 High Similarity NPC246466
0.8725 High Similarity NPC268691
0.8718 High Similarity NPC256141
0.871 High Similarity NPC267117
0.8701 High Similarity NPC218569
0.8688 High Similarity NPC112418
0.8671 High Similarity NPC313922
0.8662 High Similarity NPC203080
0.8654 High Similarity NPC471229
0.8654 High Similarity NPC207346
0.8654 High Similarity NPC295650
0.8654 High Similarity NPC475076
0.8654 High Similarity NPC46564
0.8645 High Similarity NPC70764
0.8645 High Similarity NPC277032
0.8636 High Similarity NPC122828
0.8636 High Similarity NPC44721
0.8636 High Similarity NPC21835
0.8636 High Similarity NPC176869
0.8636 High Similarity NPC40086
0.8636 High Similarity NPC146884
0.8636 High Similarity NPC3779
0.8636 High Similarity NPC211466
0.8636 High Similarity NPC476182
0.8634 High Similarity NPC471745
0.8627 High Similarity NPC316535
0.8616 High Similarity NPC52530
0.8616 High Similarity NPC472889
0.8614 High Similarity NPC232412
0.8614 High Similarity NPC86809
0.8614 High Similarity NPC98667
0.8608 High Similarity NPC208173
0.8608 High Similarity NPC175192
0.8608 High Similarity NPC170189
0.8599 High Similarity NPC226801
0.8599 High Similarity NPC243171
0.8599 High Similarity NPC35567
0.8599 High Similarity NPC478224
0.8599 High Similarity NPC171651
0.859 High Similarity NPC472891
0.859 High Similarity NPC116822
0.859 High Similarity NPC180351
0.8588 High Similarity NPC197972
0.8581 High Similarity NPC211811
0.8581 High Similarity NPC215711
0.8581 High Similarity NPC73411
0.8571 High Similarity NPC308992
0.8571 High Similarity NPC209278
0.8571 High Similarity NPC117985
0.8571 High Similarity NPC1940
0.8571 High Similarity NPC229190
0.8571 High Similarity NPC196114
0.8571 High Similarity NPC148011
0.8563 High Similarity NPC469345
0.8562 High Similarity NPC231475
0.8562 High Similarity NPC57072
0.8562 High Similarity NPC55738
0.8553 High Similarity NPC320825
0.8553 High Similarity NPC474638
0.8553 High Similarity NPC13858
0.8553 High Similarity NPC471500
0.8553 High Similarity NPC150023
0.8553 High Similarity NPC326037
0.8545 High Similarity NPC72696
0.8545 High Similarity NPC313717
0.8545 High Similarity NPC315306
0.8544 High Similarity NPC293286
0.8544 High Similarity NPC27532
0.8544 High Similarity NPC256346
0.8544 High Similarity NPC141212
0.8544 High Similarity NPC325028
0.8544 High Similarity NPC246328
0.8537 High Similarity NPC283041
0.8535 High Similarity NPC215921
0.8535 High Similarity NPC278476
0.8535 High Similarity NPC262039
0.8535 High Similarity NPC319910
0.8535 High Similarity NPC262038
0.8535 High Similarity NPC46882
0.8535 High Similarity NPC471676
0.8535 High Similarity NPC132990
0.8535 High Similarity NPC472420
0.8535 High Similarity NPC263384
0.8535 High Similarity NPC254412
0.8535 High Similarity NPC472422
0.8535 High Similarity NPC70016
0.8535 High Similarity NPC244577
0.8528 High Similarity NPC88243
0.8526 High Similarity NPC237440
0.8526 High Similarity NPC270160
0.8526 High Similarity NPC73236
0.8521 High Similarity NPC208069
0.8516 High Similarity NPC210320
0.8516 High Similarity NPC129650
0.8516 High Similarity NPC71055
0.8516 High Similarity NPC472918
0.8509 High Similarity NPC263449
0.8509 High Similarity NPC471976
0.8509 High Similarity NPC470183
0.8506 High Similarity NPC62290
0.8506 High Similarity NPC142731
0.8506 High Similarity NPC279417
0.8506 High Similarity NPC326506
0.8506 High Similarity NPC49130
0.8506 High Similarity NPC208176
0.8506 High Similarity NPC4152
0.8506 High Similarity NPC306607
0.85 High Similarity NPC471515
0.85 High Similarity NPC67876
0.85 High Similarity NPC471479
0.85 High Similarity NPC281137
0.85 High Similarity NPC282390
0.8497 Intermediate Similarity NPC476310
0.8497 Intermediate Similarity NPC476164
0.8494 Intermediate Similarity NPC472620
0.8491 Intermediate Similarity NPC478221
0.8491 Intermediate Similarity NPC472890
0.8491 Intermediate Similarity NPC69043
0.8491 Intermediate Similarity NPC304207
0.8491 Intermediate Similarity NPC217706
0.8491 Intermediate Similarity NPC99381
0.8491 Intermediate Similarity NPC48579
0.8491 Intermediate Similarity NPC478230
0.8491 Intermediate Similarity NPC473241
0.8491 Intermediate Similarity NPC259710
0.8491 Intermediate Similarity NPC207809
0.8491 Intermediate Similarity NPC317585
0.8487 Intermediate Similarity NPC145673
0.8485 Intermediate Similarity NPC472619
0.8481 Intermediate Similarity NPC75069
0.8481 Intermediate Similarity NPC9743
0.8481 Intermediate Similarity NPC240476
0.8481 Intermediate Similarity NPC36835
0.8481 Intermediate Similarity NPC184284
0.8481 Intermediate Similarity NPC138288
0.8481 Intermediate Similarity NPC61506
0.8481 Intermediate Similarity NPC210597
0.8481 Intermediate Similarity NPC115249
0.8481 Intermediate Similarity NPC217149
0.8481 Intermediate Similarity NPC260491
0.8481 Intermediate Similarity NPC216035
0.8481 Intermediate Similarity NPC246162
0.8481 Intermediate Similarity NPC76041
0.8476 Intermediate Similarity NPC178173
0.8476 Intermediate Similarity NPC20237
0.8471 Intermediate Similarity NPC470107
0.8471 Intermediate Similarity NPC105136
0.8457 Intermediate Similarity NPC173137
0.8457 Intermediate Similarity NPC476929
0.8457 Intermediate Similarity NPC3629
0.8447 Intermediate Similarity NPC22192
0.8447 Intermediate Similarity NPC152904
0.8447 Intermediate Similarity NPC125969
0.8447 Intermediate Similarity NPC477410
0.8447 Intermediate Similarity NPC470339
0.8442 Intermediate Similarity NPC103910
0.8442 Intermediate Similarity NPC105381
0.8442 Intermediate Similarity NPC10302
0.8442 Intermediate Similarity NPC59551
0.8438 Intermediate Similarity NPC20530
0.8438 Intermediate Similarity NPC250922
0.8438 Intermediate Similarity NPC78492
0.8438 Intermediate Similarity NPC215917
0.8438 Intermediate Similarity NPC164427
0.8438 Intermediate Similarity NPC10754
0.8438 Intermediate Similarity NPC201837
0.8438 Intermediate Similarity NPC208152
0.8434 Intermediate Similarity NPC241874
0.8428 Intermediate Similarity NPC469405
0.8428 Intermediate Similarity NPC7989
0.8428 Intermediate Similarity NPC100134
0.8428 Intermediate Similarity NPC137301
0.8428 Intermediate Similarity NPC155686
0.8428 Intermediate Similarity NPC299435

  Similar Clinical/Approved Drugs

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

●  The left chart: Distribution of similarity level between NPC237560 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
0.8734 High Similarity NPD7075 Discontinued
0.8726 High Similarity NPD5402 Approved
0.8662 High Similarity NPD7096 Clinical (unspecified phase)
0.8636 High Similarity NPD5403 Approved
0.8627 High Similarity NPD5401 Approved
0.8481 Intermediate Similarity NPD6801 Discontinued
0.8471 Intermediate Similarity NPD6599 Discontinued
0.8442 Intermediate Similarity NPD6799 Approved
0.8366 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.8365 Intermediate Similarity NPD1934 Approved
0.8344 Intermediate Similarity NPD1551 Phase 2
0.8323 Intermediate Similarity NPD3882 Suspended
0.8261 Intermediate Similarity NPD3817 Phase 2
0.8247 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.8235 Intermediate Similarity NPD1549 Phase 2
0.8225 Intermediate Similarity NPD6559 Discontinued
0.8199 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.8193 Intermediate Similarity NPD6166 Phase 2
0.8193 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.8176 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.817 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.817 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.816 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.8125 Intermediate Similarity NPD4380 Phase 2
0.8114 Intermediate Similarity NPD7879 Clinical (unspecified phase)
0.8098 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.8086 Intermediate Similarity NPD7819 Suspended
0.8059 Intermediate Similarity NPD6797 Phase 2
0.8047 Intermediate Similarity NPD7804 Clinical (unspecified phase)
0.8038 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.8013 Intermediate Similarity NPD3750 Approved
0.8012 Intermediate Similarity NPD7251 Discontinued
0.7988 Intermediate Similarity NPD3818 Discontinued
0.7988 Intermediate Similarity NPD3751 Discontinued
0.7987 Intermediate Similarity NPD1512 Approved
0.7975 Intermediate Similarity NPD2801 Approved
0.7965 Intermediate Similarity NPD7808 Phase 3
0.7963 Intermediate Similarity NPD7411 Suspended
0.7953 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.795 Intermediate Similarity NPD3226 Approved
0.7935 Intermediate Similarity NPD2346 Discontinued
0.7922 Intermediate Similarity NPD1510 Phase 2
0.7908 Intermediate Similarity NPD1607 Approved
0.7898 Intermediate Similarity NPD4628 Phase 3
0.7895 Intermediate Similarity NPD7074 Phase 3
0.7885 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7871 Intermediate Similarity NPD2796 Approved
0.7862 Intermediate Similarity NPD1511 Approved
0.7857 Intermediate Similarity NPD6232 Discontinued
0.7843 Intermediate Similarity NPD447 Suspended
0.7836 Intermediate Similarity NPD7054 Approved
0.7836 Intermediate Similarity NPD5844 Phase 1
0.7831 Intermediate Similarity NPD3749 Approved
0.7824 Intermediate Similarity NPD7473 Discontinued
0.7816 Intermediate Similarity NPD8312 Approved
0.7816 Intermediate Similarity NPD8313 Approved
0.7812 Intermediate Similarity NPD2533 Approved
0.7812 Intermediate Similarity NPD2532 Approved
0.7812 Intermediate Similarity NPD2534 Approved
0.7791 Intermediate Similarity NPD7472 Approved
0.7784 Intermediate Similarity NPD919 Approved
0.7778 Intermediate Similarity NPD1240 Approved
0.7771 Intermediate Similarity NPD7768 Phase 2
0.7763 Intermediate Similarity NPD411 Approved
0.7711 Intermediate Similarity NPD8443 Clinical (unspecified phase)
0.7703 Intermediate Similarity NPD9717 Approved
0.7702 Intermediate Similarity NPD7410 Clinical (unspecified phase)
0.7692 Intermediate Similarity NPD6959 Discontinued
0.7692 Intermediate Similarity NPD3748 Approved
0.7692 Intermediate Similarity NPD4308 Phase 3
0.7684 Intermediate Similarity NPD8434 Phase 2
0.7684 Intermediate Similarity NPD8150 Discontinued
0.7676 Intermediate Similarity NPD7435 Discontinued
0.7667 Intermediate Similarity NPD1203 Approved
0.7661 Intermediate Similarity NPD7852 Clinical (unspecified phase)
0.7647 Intermediate Similarity NPD2313 Discontinued
0.7643 Intermediate Similarity NPD6099 Approved
0.7643 Intermediate Similarity NPD2935 Discontinued
0.7643 Intermediate Similarity NPD6100 Approved
0.7633 Intermediate Similarity NPD5494 Approved
0.7622 Intermediate Similarity NPD5808 Clinical (unspecified phase)
0.7593 Intermediate Similarity NPD7004 Clinical (unspecified phase)
0.7545 Intermediate Similarity NPD1465 Phase 2
0.7544 Intermediate Similarity NPD3787 Discontinued
0.7533 Intermediate Similarity NPD4749 Approved
0.7532 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7532 Intermediate Similarity NPD6798 Discontinued
0.7517 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7516 Intermediate Similarity NPD6832 Phase 2
0.7514 Intermediate Similarity NPD6777 Approved
0.7514 Intermediate Similarity NPD6782 Approved
0.7514 Intermediate Similarity NPD6779 Approved
0.7514 Intermediate Similarity NPD6778 Approved
0.7514 Intermediate Similarity NPD6776 Approved
0.7514 Intermediate Similarity NPD6780 Approved
0.7514 Intermediate Similarity NPD6781 Approved
0.75 Intermediate Similarity NPD920 Approved
0.75 Intermediate Similarity NPD1933 Approved
0.75 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.75 Intermediate Similarity NPD230 Phase 1
0.75 Intermediate Similarity NPD2800 Approved
0.7485 Intermediate Similarity NPD1247 Approved
0.7468 Intermediate Similarity NPD2799 Discontinued
0.7468 Intermediate Similarity NPD7033 Discontinued
0.7457 Intermediate Similarity NPD7784 Clinical (unspecified phase)
0.7446 Intermediate Similarity NPD8090 Clinical (unspecified phase)
0.7443 Intermediate Similarity NPD5953 Discontinued
0.7436 Intermediate Similarity NPD1613 Approved
0.7436 Intermediate Similarity NPD4307 Phase 2
0.7436 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.7435 Intermediate Similarity NPD7875 Clinical (unspecified phase)
0.7435 Intermediate Similarity NPD7874 Approved
0.7419 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7407 Intermediate Similarity NPD6190 Approved
0.7399 Intermediate Similarity NPD3926 Phase 2
0.7391 Intermediate Similarity NPD1243 Approved
0.7389 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7389 Intermediate Similarity NPD5124 Phase 1
0.7389 Intermediate Similarity NPD6355 Discontinued
0.7378 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7362 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7358 Intermediate Similarity NPD1509 Clinical (unspecified phase)
0.7349 Intermediate Similarity NPD1653 Approved
0.7347 Intermediate Similarity NPD9493 Approved
0.7341 Intermediate Similarity NPD5710 Approved
0.7341 Intermediate Similarity NPD5711 Approved
0.7325 Intermediate Similarity NPD943 Approved
0.7308 Intermediate Similarity NPD8397 Clinical (unspecified phase)
0.7302 Intermediate Similarity NPD7697 Approved
0.7302 Intermediate Similarity NPD7696 Phase 3
0.7302 Intermediate Similarity NPD7698 Approved
0.7285 Intermediate Similarity NPD422 Phase 1
0.7284 Intermediate Similarity NPD1652 Phase 2
0.7273 Intermediate Similarity NPD1019 Discontinued
0.7267 Intermediate Similarity NPD2344 Approved
0.7267 Intermediate Similarity NPD5537 Clinical (unspecified phase)
0.7267 Intermediate Similarity NPD5762 Approved
0.7267 Intermediate Similarity NPD5763 Approved
0.7263 Intermediate Similarity NPD7871 Phase 2
0.7263 Intermediate Similarity NPD8319 Approved
0.7263 Intermediate Similarity NPD8320 Phase 1
0.7263 Intermediate Similarity NPD7870 Phase 2
0.7261 Intermediate Similarity NPD6233 Phase 2
0.7244 Intermediate Similarity NPD4625 Phase 3
0.7243 Intermediate Similarity NPD6534 Approved
0.7243 Intermediate Similarity NPD6535 Approved
0.724 Intermediate Similarity NPD7701 Phase 2
0.7238 Intermediate Similarity NPD8055 Clinical (unspecified phase)
0.7232 Intermediate Similarity NPD7286 Phase 2
0.7215 Intermediate Similarity NPD4060 Phase 1
0.7208 Intermediate Similarity NPD1470 Approved
0.7208 Intermediate Similarity NPD2797 Approved
0.7202 Intermediate Similarity NPD8151 Discontinued
0.72 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD3268 Approved
0.7195 Intermediate Similarity NPD2354 Approved
0.7186 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7179 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD6844 Discontinued
0.7176 Intermediate Similarity NPD37 Approved
0.7168 Intermediate Similarity NPD6234 Discontinued
0.7161 Intermediate Similarity NPD5647 Approved
0.7161 Intermediate Similarity NPD2798 Approved
0.716 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.7158 Intermediate Similarity NPD6823 Phase 2
0.7152 Intermediate Similarity NPD1778 Approved
0.7151 Intermediate Similarity NPD4965 Approved
0.7151 Intermediate Similarity NPD4967 Phase 2
0.7151 Intermediate Similarity NPD4966 Approved
0.7143 Intermediate Similarity NPD651 Clinical (unspecified phase)
0.7134 Intermediate Similarity NPD7095 Approved
0.7128 Intermediate Similarity NPD7700 Phase 2
0.7128 Intermediate Similarity NPD7801 Approved
0.7128 Intermediate Similarity NPD7699 Phase 2
0.7126 Intermediate Similarity NPD5049 Phase 3
0.7125 Intermediate Similarity NPD6651 Approved
0.7124 Intermediate Similarity NPD1608 Approved
0.7118 Intermediate Similarity NPD7615 Clinical (unspecified phase)
0.7117 Intermediate Similarity NPD2424 Discontinued
0.7115 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.7093 Intermediate Similarity NPD4288 Approved
0.7091 Intermediate Similarity NPD3887 Approved
0.7091 Intermediate Similarity NPD2309 Approved
0.7089 Intermediate Similarity NPD3764 Approved
0.7086 Intermediate Similarity NPD7199 Phase 2
0.7079 Intermediate Similarity NPD7228 Approved
0.707 Intermediate Similarity NPD4908 Phase 1
0.7066 Intermediate Similarity NPD4661 Approved
0.7066 Intermediate Similarity NPD4662 Approved
0.7065 Intermediate Similarity NPD8155 Clinical (unspecified phase)
0.7062 Intermediate Similarity NPD2403 Approved
0.7059 Intermediate Similarity NPD1610 Phase 2
0.7055 Intermediate Similarity NPD1471 Phase 3
0.7044 Intermediate Similarity NPD4062 Phase 3
0.7041 Intermediate Similarity NPD7783 Phase 2
0.7041 Intermediate Similarity NPD7782 Clinical (unspecified phase)
0.7032 Intermediate Similarity NPD3225 Approved
0.7025 Intermediate Similarity NPD3027 Phase 3

Structure

External Identifiers

PubChem CID   9926413
ChEMBL   CHEMBL91382
ZINC  

Physicochemical Properties

Molecular Weight:  302.08
ALogP:  -0.2806
MLogP:  2.56
XLogP:  0.675
# Rotatable Bonds:  6
Polar Surface Area:  93.06
# H-Bond Aceptor:  4
# H-Bond Donor:  2
# Rings:  3
# Heavy Atoms:  22

Download Data

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