NPASS drugs

Drug Information

Drug ID:	NPD471
Drug Name:	Chloramphenicol
Molecular Formula:	C11H12Cl2N2O5
Canonical SMILES:	OC[C@H]([C@@H](c1ccc(cc1)N(=O)=O)O)N=C(C(Cl)Cl)O
Standard InCHI:	InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
Standard InCHIKey:	WIIZWVCIJKGZOK-RKDXNWHRSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD471

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
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	136
0.1-0.2	1281
0.2-0.3	8391
0.3-0.4	10057
0.4-0.5	9266
0.5-0.6	1646
0.6-0.7	110
0.7-0.8	2
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similar Natural Products

High Similarity Level: Tc>=0.85; Intermediate Similarity Level: 0.7 <= Tc < 0.85; Remote Similarity Level: 0.65 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC159589
Intermediate Similarity	0.7153	NPC197680
Intermediate Similarity	0.7153	NPC259098
Remote Similarity	0.6944	NPC325013
Remote Similarity	0.6897	NPC314278
Remote Similarity	0.6712	NPC205946
Remote Similarity	0.6688	NPC470824
Remote Similarity	0.6644	NPC226662
Remote Similarity	0.6643	NPC205652
Remote Similarity	0.6643	NPC470550
Remote Similarity	0.6618	NPC37584
Remote Similarity	0.6593	NPC211551
Remote Similarity	0.6589	NPC476483
Remote Similarity	0.6577	NPC101372
Remote Similarity	0.6567	NPC178681
Remote Similarity	0.6549	NPC147957
Remote Similarity	0.6541	NPC214200
Remote Similarity	0.6541	NPC228400
Remote Similarity	0.6515	NPC290515
Remote Similarity	0.6515	NPC303611
Remote Similarity	0.6515	NPC164514
Remote Similarity	0.6515	NPC226096
Remote Similarity	0.6515	NPC108606
Remote Similarity	0.6454	NPC474544
Remote Similarity	0.6454	NPC1986
Remote Similarity	0.6452	NPC287358
Remote Similarity	0.6447	NPC313466
Remote Similarity	0.6412	NPC215351
Remote Similarity	0.6412	NPC20142
Remote Similarity	0.6397	NPC226778
Remote Similarity	0.6397	NPC224610
Remote Similarity	0.6397	NPC304761
Remote Similarity	0.6397	NPC147000
Remote Similarity	0.6397	NPC150254
Remote Similarity	0.6397	NPC113326
Remote Similarity	0.6397	NPC194390
Remote Similarity	0.6397	NPC88267
Remote Similarity	0.6385	NPC265521
Remote Similarity	0.6377	NPC44836
Remote Similarity	0.6357	NPC9336
Remote Similarity	0.6346	NPC166667
Remote Similarity	0.6329	NPC314113
Remote Similarity	0.6286	NPC255721
Remote Similarity	0.6259	NPC76327
Remote Similarity	0.625	NPC327226
Remote Similarity	0.625	NPC291359
Remote Similarity	0.625	NPC317254
Remote Similarity	0.6242	NPC184161
Remote Similarity	0.6231	NPC78154
Remote Similarity	0.6228	NPC10875
Remote Similarity	0.6228	NPC10730
Remote Similarity	0.6224	NPC322735
Remote Similarity	0.6218	NPC317872
Remote Similarity	0.6211	NPC472103
Remote Similarity	0.6196	NPC315829
Remote Similarity	0.6196	NPC254798
Remote Similarity	0.619	NPC321869
Remote Similarity	0.6183	NPC226438
Remote Similarity	0.6181	NPC118202
Remote Similarity	0.6181	NPC329190
Remote Similarity	0.6178	NPC64205
Remote Similarity	0.6174	NPC474862
Remote Similarity	0.6173	NPC472242
Remote Similarity	0.6169	NPC314473
Remote Similarity	0.6169	NPC314098
Remote Similarity	0.6165	NPC58674
Remote Similarity	0.6164	NPC311737
Remote Similarity	0.6164	NPC38458
Remote Similarity	0.6154	NPC184437
Remote Similarity	0.6149	NPC150323
Remote Similarity	0.6144	NPC469666
Remote Similarity	0.6139	NPC159722
Remote Similarity	0.6135	NPC472100
Remote Similarity	0.6129	NPC476687
Remote Similarity	0.6129	NPC476689
Remote Similarity	0.6129	NPC476685
Remote Similarity	0.6119	NPC25565
Remote Similarity	0.6098	NPC161292
Remote Similarity	0.6096	NPC82963
Remote Similarity	0.6093	NPC317758
Remote Similarity	0.6092	NPC257354
Remote Similarity	0.609	NPC208757
Remote Similarity	0.6089	NPC192270
Remote Similarity	0.6087	NPC178902
Remote Similarity	0.6081	NPC283760
Remote Similarity	0.6076	NPC475707
Remote Similarity	0.6074	NPC475439
Remote Similarity	0.6074	NPC473501
Remote Similarity	0.6074	NPC33168
Remote Similarity	0.6069	NPC19555
Remote Similarity	0.6062	NPC243162
Remote Similarity	0.6062	NPC472243
Remote Similarity	0.6057	NPC83241
Remote Similarity	0.6056	NPC65855
Remote Similarity	0.6056	NPC292758
Remote Similarity	0.6056	NPC471785
Remote Similarity	0.6053	NPC474479
Remote Similarity	0.6053	NPC474926
Remote Similarity	0.6048	NPC153769
Remote Similarity	0.6045	NPC161972
Remote Similarity	0.6045	NPC303045
Remote Similarity	0.604	NPC326232
Remote Similarity	0.6038	NPC126637
Remote Similarity	0.6037	NPC259678
Remote Similarity	0.6031	NPC470877
Remote Similarity	0.6027	NPC222982
Remote Similarity	0.6026	NPC283130
Remote Similarity	0.6026	NPC328683
Remote Similarity	0.6023	NPC477158
Remote Similarity	0.6014	NPC329358
Remote Similarity	0.6012	NPC314186
Remote Similarity	0.6	NPC471638
Remote Similarity	0.6	NPC319645
Remote Similarity	0.5989	NPC95412
Remote Similarity	0.5988	NPC472241
Remote Similarity	0.5985	NPC74936
Remote Similarity	0.5985	NPC159178
Remote Similarity	0.5985	NPC121872
Remote Similarity	0.5985	NPC141139
Remote Similarity	0.5985	NPC471307
Remote Similarity	0.5985	NPC78041
Remote Similarity	0.5985	NPC209764
Remote Similarity	0.5977	NPC238430
Remote Similarity	0.5973	NPC319950
Remote Similarity	0.596	NPC27581
Remote Similarity	0.5957	NPC231705
Remote Similarity	0.5956	NPC311242
Remote Similarity	0.5954	NPC12429
Remote Similarity	0.5952	NPC219383
Remote Similarity	0.5951	NPC314287
Remote Similarity	0.5948	NPC472414
Remote Similarity	0.5948	NPC4974
Remote Similarity	0.5944	NPC258056
Remote Similarity	0.5944	NPC290566
Remote Similarity	0.5944	NPC145638
Remote Similarity	0.5941	NPC477156
Remote Similarity	0.5941	NPC477157
Remote Similarity	0.5939	NPC478039
Remote Similarity	0.5933	NPC317564
Remote Similarity	0.5933	NPC190663
Remote Similarity	0.5933	NPC80150
Remote Similarity	0.5932	NPC34508
Remote Similarity	0.5922	NPC293472
Remote Similarity	0.5918	NPC101139
Remote Similarity	0.5917	NPC471132
Remote Similarity	0.5915	NPC282578
Remote Similarity	0.5915	NPC142297
Remote Similarity	0.5915	NPC323798
Remote Similarity	0.5909	NPC278097
Remote Similarity	0.5906	NPC117180
Remote Similarity	0.5903	NPC474149
Remote Similarity	0.5901	NPC214988
Remote Similarity	0.5897	NPC280807
Remote Similarity	0.5897	NPC314431
Remote Similarity	0.5896	NPC72291
Remote Similarity	0.5896	NPC85651
Remote Similarity	0.5896	NPC253667
Remote Similarity	0.5896	NPC289776
Remote Similarity	0.5896	NPC133470
Remote Similarity	0.5896	NPC191863
Remote Similarity	0.5896	NPC35510
Remote Similarity	0.589	NPC264782
Remote Similarity	0.5889	NPC270009
Remote Similarity	0.5882	NPC3371
Remote Similarity	0.5878	NPC198747
Remote Similarity	0.5878	NPC211237
Remote Similarity	0.5878	NPC473031
Remote Similarity	0.5878	NPC2265
Remote Similarity	0.5876	NPC158129
Remote Similarity	0.5874	NPC153690
Remote Similarity	0.5874	NPC96224
Remote Similarity	0.5874	NPC24101
Remote Similarity	0.587	NPC323726
Remote Similarity	0.5867	NPC14950
Remote Similarity	0.5866	NPC168153
Remote Similarity	0.5866	NPC288785
Remote Similarity	0.5865	NPC172128
Remote Similarity	0.5865	NPC316108
Remote Similarity	0.5864	NPC197921
Remote Similarity	0.5859	NPC87299
Remote Similarity	0.5859	NPC329319
Remote Similarity	0.5859	NPC99394
Remote Similarity	0.5859	NPC103326
Remote Similarity	0.5857	NPC471310
Remote Similarity	0.5855	NPC252878
Remote Similarity	0.5855	NPC160493
Remote Similarity	0.5852	NPC469462
Remote Similarity	0.5852	NPC471309
Remote Similarity	0.585	NPC142599
Remote Similarity	0.5848	NPC141353
Remote Similarity	0.5844	NPC95733
Remote Similarity	0.5844	NPC47667
Remote Similarity	0.5844	NPC62101
Remote Similarity	0.5843	NPC225381
Remote Similarity	0.5839	NPC137096
Remote Similarity	0.5839	NPC169328
Remote Similarity	0.5838	NPC231862
Remote Similarity	0.5833	NPC318086
Remote Similarity	0.5833	NPC477839
Remote Similarity	0.5833	NPC150863

Drug Structure

NPD471 OpenBabel08201723202D 23 23 0 0 1 0 0 0 0 0999 V2000 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -5.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 3 1 0 0 0 0 1 6 2 0 0 0 0 2 4 2 0 0 0 0 2 6 1 0 0 0 0 3 7 2 0 0 0 0 4 7 1 0 0 0 0 5 16 1 0 0 0 0 6 9 1 0 0 0 0 7 15 1 0 0 0 0 8 5 1 6 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 17 1 1 0 0 0 10 11 1 0 0 0 0 10 12 1 0 0 0 0 10 13 1 0 0 0 0 11 14 2 3 0 0 0 11 18 1 0 0 0 0 15 19 2 0 0 0 0 15 20 2 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000460; DAP001356
DrugBank	DB00446
ChEMBL	CHEMBL130
IUPHAR/BPS
PharmaGKB	PA448927
KEGG Drug	D00104
PubChem CID	5959
ChEBI	17698
CAS Number	56-75-7

Drug Properties

Molecular Weight	322.01
ALogP	0.6616
MLogP	1.68
XLogP	1.663
HDA	4
HBD	3
Rotatable Bonds	12
TPSA	116.19
RO5 Violation	0