NPASS drugs

Drug Information

Drug ID:	NPD5099
Drug Name:	Fluphenazine
Molecular Formula:	C22H26F3N3OS
Canonical SMILES:	OCCN1CCN(CC1)CCCN1c2ccccc2Sc2c1cc(cc2)C(F)(F)F
Standard InCHI:	InChI=1S/C22H26F3N3OS/c23-22(24,25)17-6-7-21-19(16-17)28(18-4-1-2-5-20(18)30-21)9-3-8-26-10-12-27(13-11-26)14-15-29/h1-2,4-7,16,29H,3,8-15H2
Standard InCHIKey:	PLDUPXSUYLZYBN-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5099

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	228
0.1-0.2	3366
0.2-0.3	12590
0.3-0.4	10618
0.4-0.5	3365
0.5-0.6	699
0.6-0.7	22
0.7-0.8	1
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
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
High Similarity	0.916	NPC473417
Intermediate Similarity	0.7403	NPC321617
Remote Similarity	0.697	NPC291610
Remote Similarity	0.6866	NPC328877
Remote Similarity	0.6531	NPC475915
Remote Similarity	0.6519	NPC470301
Remote Similarity	0.6312	NPC22082
Remote Similarity	0.6312	NPC186284
Remote Similarity	0.6242	NPC313352
Remote Similarity	0.6169	NPC476950
Remote Similarity	0.6134	NPC175916
Remote Similarity	0.6104	NPC252794
Remote Similarity	0.6103	NPC66699
Remote Similarity	0.6096	NPC296163
Remote Similarity	0.604	NPC192209
Remote Similarity	0.604	NPC313449
Remote Similarity	0.6034	NPC328270
Remote Similarity	0.6026	NPC328590
Remote Similarity	0.6024	NPC264589
Remote Similarity	0.6014	NPC79618
Remote Similarity	0.6014	NPC434
Remote Similarity	0.6013	NPC283130
Remote Similarity	0.6013	NPC328683
Remote Similarity	0.601	NPC124636
Remote Similarity	0.598	NPC193370
Remote Similarity	0.5972	NPC302790
Remote Similarity	0.5964	NPC470824
Remote Similarity	0.595	NPC471741
Remote Similarity	0.5906	NPC218710
Remote Similarity	0.5878	NPC187036
Remote Similarity	0.586	NPC478079
Remote Similarity	0.5858	NPC109787
Remote Similarity	0.5855	NPC226143
Remote Similarity	0.5843	NPC88121
Remote Similarity	0.5839	NPC184437
Remote Similarity	0.5817	NPC302169
Remote Similarity	0.5813	NPC53044
Remote Similarity	0.5808	NPC320863
Remote Similarity	0.58	NPC288232
Remote Similarity	0.5795	NPC85651
Remote Similarity	0.5792	NPC133261
Remote Similarity	0.5784	NPC173344
Remote Similarity	0.5779	NPC257490
Remote Similarity	0.5779	NPC314192
Remote Similarity	0.5778	NPC318183
Remote Similarity	0.5776	NPC256893
Remote Similarity	0.5767	NPC128582
Remote Similarity	0.5767	NPC471123
Remote Similarity	0.5758	NPC243162
Remote Similarity	0.5756	NPC149014
Remote Similarity	0.5754	NPC317430
Remote Similarity	0.5747	NPC172937
Remote Similarity	0.5747	NPC94167
Remote Similarity	0.5746	NPC473880
Remote Similarity	0.5746	NPC472123
Remote Similarity	0.5739	NPC255229
Remote Similarity	0.5739	NPC81229
Remote Similarity	0.5714	NPC316582
Remote Similarity	0.5714	NPC20144
Remote Similarity	0.57	NPC77022
Remote Similarity	0.5698	NPC472114
Remote Similarity	0.5698	NPC475763
Remote Similarity	0.5698	NPC472115
Remote Similarity	0.5697	NPC469560
Remote Similarity	0.5693	NPC470926
Remote Similarity	0.5687	NPC9856
Remote Similarity	0.5686	NPC264580
Remote Similarity	0.5683	NPC150048
Remote Similarity	0.5683	NPC472122
Remote Similarity	0.5683	NPC203754
Remote Similarity	0.5683	NPC24594
Remote Similarity	0.5673	NPC216221
Remote Similarity	0.5667	NPC57051
Remote Similarity	0.5663	NPC130251
Remote Similarity	0.5657	NPC315257
Remote Similarity	0.5652	NPC326575
Remote Similarity	0.5649	NPC291962
Remote Similarity	0.5649	NPC177684
Remote Similarity	0.5647	NPC469735
Remote Similarity	0.5642	NPC475420
Remote Similarity	0.5642	NPC472106
Remote Similarity	0.5641	NPC268534
Remote Similarity	0.5635	NPC472118
Remote Similarity	0.5632	NPC478076
Remote Similarity	0.5629	NPC88097
Remote Similarity	0.5625	NPC104345
Remote Similarity	0.562	NPC78154
Remote Similarity	0.5618	NPC472101
Remote Similarity	0.5618	NPC472120
Remote Similarity	0.5613	NPC161956
Remote Similarity	0.5613	NPC258531
Remote Similarity	0.5613	NPC112373
Remote Similarity	0.5611	NPC182131
Remote Similarity	0.5607	NPC66936

Drug Structure

NPD5099 OpenBabel08211706322D 31 34 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -0.8660 1.5000 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 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 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 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 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 0.0000 -3.0000 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 0.0000 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -4.8660 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 -4.0000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -4.5000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 1.5000 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 -7.7942 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 4.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 0 0 0 1 4 1 0 0 0 0 2 5 1 0 0 0 0 3 8 1 0 0 0 0 3 9 1 0 0 0 0 4 18 2 0 0 0 0 5 20 2 0 0 0 0 6 7 2 0 0 0 0 6 17 1 0 0 0 0 7 21 1 0 0 0 0 8 26 1 0 0 0 0 9 28 1 0 0 0 0 10 12 1 0 0 0 0 10 26 1 0 0 0 0 11 13 1 0 0 0 0 11 26 1 0 0 0 0 12 27 1 0 0 0 0 13 27 1 0 0 0 0 14 15 1 0 0 0 0 14 27 1 0 0 0 0 15 29 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 22 1 0 0 0 0 18 20 1 0 0 0 0 18 28 1 0 0 0 0 19 21 2 0 0 0 0 19 28 1 0 0 0 0 20 30 1 0 0 0 0 21 30 1 0 0 0 0 22 23 1 0 0 0 0 22 24 1 0 0 0 0 22 25 1 0 0 0 0 29 31 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000371; DAP000375; DCL000806
DrugBank	DB00623
ChEMBL	CHEMBL726
IUPHAR/BPS	204
PharmaGKB	PA449676
KEGG Drug
PubChem CID	3372
ChEBI	5123
CAS Number	69-23-8

Drug Properties

Molecular Weight	437.17
ALogP	1.0728
MLogP	3
XLogP	4.409
HDA	4
HBD	1
Rotatable Bonds	11
TPSA	55.25
RO5 Violation	0