NPASS drugs

Drug Information

Drug ID:	NPD5196
Drug Name:	Mitoxantrone
Molecular Formula:	C22H28N4O6
Canonical SMILES:	OCCNCCNc1ccc(c2c1C(=O)c1c(C2=O)c(O)ccc1O)NCCNCCO
Standard InCHI:	InChI=1S/C22H28N4O6/c27-11-9-23-5-7-25-13-1-2-14(26-8-6-24-10-12-28)18-17(13)21(31)19-15(29)3-4-16(30)20(19)22(18)32/h1-4,23-30H,5-12H2
Standard InCHIKey:	KKZJGLLVHKMTCM-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5196

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	251
0.1-0.2	1256
0.2-0.3	5311
0.3-0.4	7427
0.4-0.5	7760
0.5-0.6	8118
0.6-0.7	745
0.7-0.8	22
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

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
Intermediate Similarity	0.7638	NPC317727
Intermediate Similarity	0.7634	NPC471778
Intermediate Similarity	0.7537	NPC133156
Intermediate Similarity	0.75	NPC112336
Intermediate Similarity	0.75	NPC474814
Intermediate Similarity	0.7419	NPC204867
Intermediate Similarity	0.7379	NPC478075
Intermediate Similarity	0.7236	NPC474059
Intermediate Similarity	0.7228	NPC170333
Intermediate Similarity	0.7216	NPC474815
Intermediate Similarity	0.7192	NPC316282
Intermediate Similarity	0.7181	NPC199737
Intermediate Similarity	0.7175	NPC313720
Intermediate Similarity	0.7175	NPC17160
Intermediate Similarity	0.7158	NPC144691
Intermediate Similarity	0.7109	NPC25961
Intermediate Similarity	0.7047	NPC126676
Intermediate Similarity	0.7047	NPC469671
Intermediate Similarity	0.7045	NPC285254
Intermediate Similarity	0.7026	NPC471743
Intermediate Similarity	0.7015	NPC477998
Intermediate Similarity	0.7005	NPC298320
Remote Similarity	0.6977	NPC298449
Remote Similarity	0.6967	NPC212123
Remote Similarity	0.6948	NPC474366
Remote Similarity	0.6883	NPC208522
Remote Similarity	0.6882	NPC241392
Remote Similarity	0.6881	NPC134702
Remote Similarity	0.6881	NPC295531
Remote Similarity	0.6854	NPC100573
Remote Similarity	0.6854	NPC207873
Remote Similarity	0.6852	NPC114468
Remote Similarity	0.685	NPC470317
Remote Similarity	0.6837	NPC220337
Remote Similarity	0.6827	NPC17677
Remote Similarity	0.682	NPC148391
Remote Similarity	0.6814	NPC5630
Remote Similarity	0.6808	NPC222561
Remote Similarity	0.6804	NPC182131
Remote Similarity	0.68	NPC291305
Remote Similarity	0.68	NPC472163
Remote Similarity	0.6794	NPC90358
Remote Similarity	0.6794	NPC107828
Remote Similarity	0.6787	NPC118189
Remote Similarity	0.6787	NPC7560
Remote Similarity	0.6776	NPC90185
Remote Similarity	0.6774	NPC30749
Remote Similarity	0.6771	NPC93653
Remote Similarity	0.6766	NPC469973
Remote Similarity	0.6765	NPC329790
Remote Similarity	0.6759	NPC218303
Remote Similarity	0.6757	NPC251071
Remote Similarity	0.6748	NPC206109
Remote Similarity	0.6748	NPC114039
Remote Similarity	0.6746	NPC132874
Remote Similarity	0.6746	NPC218733
Remote Similarity	0.6746	NPC138615
Remote Similarity	0.6746	NPC265642
Remote Similarity	0.6743	NPC2905
Remote Similarity	0.6743	NPC176113
Remote Similarity	0.6736	NPC475983
Remote Similarity	0.6735	NPC472118
Remote Similarity	0.6732	NPC313293
Remote Similarity	0.673	NPC471489
Remote Similarity	0.673	NPC176371
Remote Similarity	0.673	NPC136573
Remote Similarity	0.6729	NPC198160
Remote Similarity	0.6728	NPC305542
Remote Similarity	0.6721	NPC43477
Remote Similarity	0.6712	NPC76478
Remote Similarity	0.6703	NPC297322
Remote Similarity	0.67	NPC49184
Remote Similarity	0.6699	NPC1820
Remote Similarity	0.6698	NPC288759
Remote Similarity	0.6697	NPC217903
Remote Similarity	0.6682	NPC295479
Remote Similarity	0.6682	NPC9894
Remote Similarity	0.6682	NPC220241
Remote Similarity	0.6667	NPC49547
Remote Similarity	0.6667	NPC238108
Remote Similarity	0.6667	NPC150308
Remote Similarity	0.6667	NPC112752
Remote Similarity	0.6667	NPC311054
Remote Similarity	0.6652	NPC182853
Remote Similarity	0.6652	NPC154922
Remote Similarity	0.6651	NPC232600
Remote Similarity	0.6651	NPC116178
Remote Similarity	0.6651	NPC303214
Remote Similarity	0.6651	NPC308943
Remote Similarity	0.6637	NPC13249
Remote Similarity	0.6636	NPC301292
Remote Similarity	0.6636	NPC234772
Remote Similarity	0.6636	NPC313112
Remote Similarity	0.6632	NPC68967
Remote Similarity	0.6631	NPC146370
Remote Similarity	0.6631	NPC470579
Remote Similarity	0.6622	NPC122886
Remote Similarity	0.6621	NPC268223
Remote Similarity	0.6621	NPC321166
Remote Similarity	0.662	NPC1464
Remote Similarity	0.662	NPC15987
Remote Similarity	0.6618	NPC203628
Remote Similarity	0.661	NPC96915
Remote Similarity	0.6603	NPC198205
Remote Similarity	0.6603	NPC21483
Remote Similarity	0.6602	NPC18890
Remote Similarity	0.6598	NPC132385
Remote Similarity	0.6584	NPC283810
Remote Similarity	0.6584	NPC166169
Remote Similarity	0.6575	NPC219087
Remote Similarity	0.6569	NPC471742
Remote Similarity	0.6557	NPC241263
Remote Similarity	0.6556	NPC136588
Remote Similarity	0.6556	NPC199253
Remote Similarity	0.6544	NPC330683
Remote Similarity	0.6544	NPC329567
Remote Similarity	0.654	NPC90967
Remote Similarity	0.654	NPC198390
Remote Similarity	0.6538	NPC70340
Remote Similarity	0.6538	NPC92803
Remote Similarity	0.6532	NPC293151
Remote Similarity	0.6531	NPC189116
Remote Similarity	0.6528	NPC225400
Remote Similarity	0.6524	NPC469815
Remote Similarity	0.6524	NPC469816
Remote Similarity	0.652	NPC314659
Remote Similarity	0.6515	NPC185172
Remote Similarity	0.6514	NPC477160
Remote Similarity	0.6511	NPC113455
Remote Similarity	0.6508	NPC476444
Remote Similarity	0.6505	NPC276674
Remote Similarity	0.6505	NPC33902
Remote Similarity	0.6505	NPC87391
Remote Similarity	0.6504	NPC94842
Remote Similarity	0.6498	NPC477999
Remote Similarity	0.6498	NPC471155
Remote Similarity	0.6498	NPC472538
Remote Similarity	0.6498	NPC470786
Remote Similarity	0.6497	NPC299582
Remote Similarity	0.6495	NPC469732
Remote Similarity	0.6493	NPC125924
Remote Similarity	0.6491	NPC74575
Remote Similarity	0.6488	NPC302235
Remote Similarity	0.6486	NPC305060
Remote Similarity	0.6484	NPC246693
Remote Similarity	0.6484	NPC242358
Remote Similarity	0.6484	NPC110609
Remote Similarity	0.6484	NPC70622
Remote Similarity	0.6484	NPC253476
Remote Similarity	0.6482	NPC314693
Remote Similarity	0.648	NPC471530
Remote Similarity	0.6473	NPC206186
Remote Similarity	0.6471	NPC197335
Remote Similarity	0.6468	NPC270241
Remote Similarity	0.6468	NPC470548
Remote Similarity	0.6465	NPC96730
Remote Similarity	0.6457	NPC469727
Remote Similarity	0.6455	NPC23294
Remote Similarity	0.6453	NPC475094
Remote Similarity	0.6453	NPC151171
Remote Similarity	0.645	NPC292265
Remote Similarity	0.6448	NPC52407
Remote Similarity	0.6447	NPC292143
Remote Similarity	0.6447	NPC139506
Remote Similarity	0.6444	NPC276657
Remote Similarity	0.6442	NPC320088
Remote Similarity	0.6441	NPC55470
Remote Similarity	0.6441	NPC375356
Remote Similarity	0.6439	NPC477159
Remote Similarity	0.6438	NPC473187
Remote Similarity	0.6432	NPC272268
Remote Similarity	0.6432	NPC193906
Remote Similarity	0.6432	NPC234933
Remote Similarity	0.6432	NPC51388
Remote Similarity	0.6432	NPC112937
Remote Similarity	0.6432	NPC23080
Remote Similarity	0.6429	NPC205992
Remote Similarity	0.6429	NPC27904
Remote Similarity	0.6429	NPC120239
Remote Similarity	0.6429	NPC313582
Remote Similarity	0.6425	NPC288854
Remote Similarity	0.6425	NPC306765
Remote Similarity	0.6422	NPC270918
Remote Similarity	0.6422	NPC85613
Remote Similarity	0.6422	NPC70092
Remote Similarity	0.6418	NPC73280
Remote Similarity	0.6416	NPC329830
Remote Similarity	0.6411	NPC45389
Remote Similarity	0.6409	NPC303951
Remote Similarity	0.6404	NPC477187
Remote Similarity	0.6404	NPC115588
Remote Similarity	0.6402	NPC218388
Remote Similarity	0.64	NPC288110
Remote Similarity	0.6398	NPC245923
Remote Similarity	0.6398	NPC45850
Remote Similarity	0.6398	NPC78284
Remote Similarity	0.6395	NPC476220
Remote Similarity	0.6395	NPC160113
Remote Similarity	0.6394	NPC21425
Remote Similarity	0.6393	NPC86834

Drug Structure

NPD5196 OpenBabel08211706322D 40 42 0 0 0 0 0 0 0 0999 V2000 -2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 5.0000 0.0000 C 0 0 0 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 -1.7321 2.0000 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 1.7321 2.0000 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 -0.8660 1.5000 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 0.8660 1.5000 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 -0.0000 2.0000 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 -4.3301 3.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -2.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 3.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 5.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -6.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 13 1 0 0 0 0 2 14 1 0 0 0 0 3 4 2 0 0 0 0 3 15 1 0 0 0 0 4 16 1 0 0 0 0 5 7 1 0 0 0 0 5 23 1 0 0 0 0 6 8 1 0 0 0 0 6 24 1 0 0 0 0 7 25 1 0 0 0 0 8 26 1 0 0 0 0 9 11 1 0 0 0 0 9 23 1 0 0 0 0 10 12 1 0 0 0 0 10 24 1 0 0 0 0 11 27 1 0 0 0 0 12 28 1 0 0 0 0 13 17 2 0 0 0 0 13 25 1 0 0 0 0 14 18 2 0 0 0 0 14 26 1 0 0 0 0 15 19 2 0 0 0 0 15 29 1 0 0 0 0 16 20 2 0 0 0 0 16 30 1 0 0 0 0 17 18 1 0 0 0 0 17 21 1 0 0 0 0 18 22 1 0 0 0 0 19 20 1 0 0 0 0 19 21 1 0 0 0 0 20 22 1 0 0 0 0 21 31 2 0 0 0 0 22 32 2 0 0 0 0 23 33 1 0 0 0 0 24 34 1 0 0 0 0 25 35 1 0 0 0 0 26 36 1 0 0 0 0 27 37 1 0 0 0 0 28 38 1 0 0 0 0 29 39 1 0 0 0 0 30 40 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB006637; DAP000057
DrugBank	DB01204
ChEMBL	CHEMBL58
IUPHAR/BPS	7242
PharmaGKB	PA450526
KEGG Drug
PubChem CID	4212
ChEBI	50729
CAS Number	65271-80-9

Drug Properties

Molecular Weight	444.20
ALogP	-3.9576
MLogP	2.78
XLogP	-2.166
HDA	8
HBD	8
Rotatable Bonds	16
TPSA	163.18
RO5 Violation	2