NPASS drugs

Drug Information

Drug ID:	NPD4422
Drug Name:	BMS-816336
Molecular Formula:	C21H22ClN3O2
Canonical SMILES:	Clc1cccc(c1C)Oc1cccn2c1nnc2[C@]12CC[C@](CC1)(CC2)O
Standard InCHI:	InChI=1S/C21H22ClN3O2/c1-14-15(22)4-2-5-16(14)27-17-6-3-13-25-18(17)23-24-19(25)20-7-10-21(26,11-8-20)12-9-20/h2-6,13,26H,7-12H2,1H3/t20-,21+
Standard InCHIKey:	BAGSDLHAZBBSOF-OYRHEFFESA-N
Max Developmental Stage:	Phase 1
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD4422

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	614
0.1-0.2	3771
0.2-0.3	9259
0.3-0.4	11091
0.4-0.5	4521
0.5-0.6	1488
0.6-0.7	146
0.7-0.8	0
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
Remote Similarity	0.6944	NPC471614
Remote Similarity	0.6769	NPC56271
Remote Similarity	0.6722	NPC242923
Remote Similarity	0.6709	NPC475774
Remote Similarity	0.6707	NPC132631
Remote Similarity	0.6707	NPC103687
Remote Similarity	0.6641	NPC228206
Remote Similarity	0.6626	NPC471603
Remote Similarity	0.6614	NPC180504
Remote Similarity	0.6601	NPC160666
Remote Similarity	0.6576	NPC30540
Remote Similarity	0.6494	NPC130570
Remote Similarity	0.6477	NPC472067
Remote Similarity	0.6477	NPC472031
Remote Similarity	0.6477	NPC472066
Remote Similarity	0.6475	NPC290689
Remote Similarity	0.6468	NPC289786
Remote Similarity	0.6466	NPC308906
Remote Similarity	0.6457	NPC315822
Remote Similarity	0.6456	NPC267928
Remote Similarity	0.6423	NPC251160
Remote Similarity	0.6413	NPC471178
Remote Similarity	0.6412	NPC477796
Remote Similarity	0.6412	NPC477805
Remote Similarity	0.6412	NPC477806
Remote Similarity	0.6412	NPC477795
Remote Similarity	0.6393	NPC287208
Remote Similarity	0.6368	NPC472289
Remote Similarity	0.6356	NPC202605
Remote Similarity	0.6356	NPC112206
Remote Similarity	0.6345	NPC62995
Remote Similarity	0.6345	NPC473053
Remote Similarity	0.634	NPC471593
Remote Similarity	0.6337	NPC36229
Remote Similarity	0.6337	NPC16452
Remote Similarity	0.6337	NPC476581
Remote Similarity	0.6328	NPC314954
Remote Similarity	0.6327	NPC470931
Remote Similarity	0.6327	NPC476465
Remote Similarity	0.6307	NPC477019
Remote Similarity	0.6307	NPC19872
Remote Similarity	0.629	NPC53069
Remote Similarity	0.629	NPC296482
Remote Similarity	0.629	NPC202768
Remote Similarity	0.6289	NPC473185
Remote Similarity	0.6287	NPC195268
Remote Similarity	0.6287	NPC133140
Remote Similarity	0.6279	NPC300114
Remote Similarity	0.6279	NPC475253
Remote Similarity	0.6278	NPC472068
Remote Similarity	0.627	NPC285558
Remote Similarity	0.6266	NPC476578
Remote Similarity	0.6266	NPC476582
Remote Similarity	0.6266	NPC4071
Remote Similarity	0.6265	NPC476287
Remote Similarity	0.626	NPC122463
Remote Similarity	0.625	NPC124542
Remote Similarity	0.625	NPC59779
Remote Similarity	0.625	NPC471177
Remote Similarity	0.625	NPC2497
Remote Similarity	0.6245	NPC132642
Remote Similarity	0.6235	NPC174672
Remote Similarity	0.6231	NPC96584
Remote Similarity	0.6231	NPC255800
Remote Similarity	0.623	NPC476138
Remote Similarity	0.623	NPC245816
Remote Similarity	0.6226	NPC187145
Remote Similarity	0.6225	NPC94157
Remote Similarity	0.622	NPC313189
Remote Similarity	0.6216	NPC201508
Remote Similarity	0.6214	NPC31930
Remote Similarity	0.6206	NPC213530
Remote Similarity	0.6206	NPC193267
Remote Similarity	0.6204	NPC118832
Remote Similarity	0.6204	NPC329708
Remote Similarity	0.6204	NPC264166
Remote Similarity	0.6204	NPC274291
Remote Similarity	0.6204	NPC165349
Remote Similarity	0.6204	NPC47059
Remote Similarity	0.6203	NPC472434
Remote Similarity	0.6203	NPC3715
Remote Similarity	0.6202	NPC476997
Remote Similarity	0.6178	NPC476998
Remote Similarity	0.6178	NPC476996
Remote Similarity	0.6173	NPC11017
Remote Similarity	0.6166	NPC473822
Remote Similarity	0.6166	NPC197141
Remote Similarity	0.616	NPC171409
Remote Similarity	0.616	NPC26679
Remote Similarity	0.616	NPC177056
Remote Similarity	0.616	NPC96405
Remote Similarity	0.6157	NPC310118
Remote Similarity	0.6151	NPC8022
Remote Similarity	0.6151	NPC470799
Remote Similarity	0.6142	NPC250178
Remote Similarity	0.6141	NPC194967
Remote Similarity	0.6139	NPC476994
Remote Similarity	0.613	NPC469554
Remote Similarity	0.6129	NPC82548
Remote Similarity	0.6125	NPC307963
Remote Similarity	0.6121	NPC211997
Remote Similarity	0.612	NPC208284
Remote Similarity	0.6113	NPC472111
Remote Similarity	0.6107	NPC141053
Remote Similarity	0.6104	NPC185782
Remote Similarity	0.6104	NPC469589
Remote Similarity	0.6104	NPC174758
Remote Similarity	0.6102	NPC100079
Remote Similarity	0.6102	NPC23614
Remote Similarity	0.61	NPC280638
Remote Similarity	0.6098	NPC473183
Remote Similarity	0.6089	NPC135549
Remote Similarity	0.6081	NPC472435
Remote Similarity	0.608	NPC11464
Remote Similarity	0.608	NPC167860
Remote Similarity	0.608	NPC123976
Remote Similarity	0.6078	NPC134586
Remote Similarity	0.6071	NPC271215
Remote Similarity	0.6071	NPC149471
Remote Similarity	0.6071	NPC266931
Remote Similarity	0.6069	NPC101543
Remote Similarity	0.6066	NPC287437
Remote Similarity	0.6055	NPC477533
Remote Similarity	0.6043	NPC144114
Remote Similarity	0.6042	NPC92111
Remote Similarity	0.6041	NPC176538
Remote Similarity	0.6041	NPC234197
Remote Similarity	0.6038	NPC110151
Remote Similarity	0.6024	NPC170114
Remote Similarity	0.6024	NPC288349
Remote Similarity	0.6023	NPC471615
Remote Similarity	0.6023	NPC473184
Remote Similarity	0.6017	NPC141915
Remote Similarity	0.6017	NPC114335
Remote Similarity	0.6017	NPC280964
Remote Similarity	0.6016	NPC46451
Remote Similarity	0.6016	NPC473179
Remote Similarity	0.6016	NPC232727
Remote Similarity	0.6014	NPC472436
Remote Similarity	0.6009	NPC473057
Remote Similarity	0.6008	NPC472193
Remote Similarity	0.6008	NPC216612
Remote Similarity	0.6008	NPC118121
Remote Similarity	0.6008	NPC251090
Remote Similarity	0.6	NPC295228
Remote Similarity	0.6	NPC76748
Remote Similarity	0.5992	NPC174049
Remote Similarity	0.5992	NPC475085
Remote Similarity	0.5992	NPC475112
Remote Similarity	0.5992	NPC291535
Remote Similarity	0.5984	NPC224928
Remote Similarity	0.5984	NPC235076
Remote Similarity	0.5984	NPC323345
Remote Similarity	0.5984	NPC470549
Remote Similarity	0.5984	NPC470164
Remote Similarity	0.5977	NPC476995
Remote Similarity	0.5977	NPC204446
Remote Similarity	0.5976	NPC209769
Remote Similarity	0.5975	NPC219963
Remote Similarity	0.5975	NPC470474
Remote Similarity	0.5975	NPC477891
Remote Similarity	0.5975	NPC266551
Remote Similarity	0.5975	NPC161887
Remote Similarity	0.5974	NPC477888
Remote Similarity	0.597	NPC476999
Remote Similarity	0.597	NPC99891
Remote Similarity	0.5968	NPC469440
Remote Similarity	0.5968	NPC200836
Remote Similarity	0.5966	NPC20249
Remote Similarity	0.5965	NPC177404
Remote Similarity	0.5961	NPC274982
Remote Similarity	0.5959	NPC239954
Remote Similarity	0.5958	NPC296527
Remote Similarity	0.5957	NPC98187
Remote Similarity	0.5952	NPC188420
Remote Similarity	0.5952	NPC470020
Remote Similarity	0.5952	NPC5145
Remote Similarity	0.5951	NPC267423
Remote Similarity	0.595	NPC99666
Remote Similarity	0.5948	NPC295452
Remote Similarity	0.5948	NPC39092
Remote Similarity	0.5948	NPC171393
Remote Similarity	0.5944	NPC470930
Remote Similarity	0.5944	NPC164374
Remote Similarity	0.5944	NPC472259
Remote Similarity	0.5944	NPC137929
Remote Similarity	0.5944	NPC475070
Remote Similarity	0.5943	NPC13880
Remote Similarity	0.5939	NPC97367
Remote Similarity	0.5938	NPC12100
Remote Similarity	0.5936	NPC477111
Remote Similarity	0.5935	NPC476167
Remote Similarity	0.5935	NPC18487
Remote Similarity	0.5933	NPC477861
Remote Similarity	0.5932	NPC271792
Remote Similarity	0.5932	NPC115595
Remote Similarity	0.5927	NPC470678
Remote Similarity	0.5926	NPC198673
Remote Similarity	0.5926	NPC226202
Remote Similarity	0.5926	NPC103230

Drug Structure

NPD4422 OpenBabel08211705262D 28 32 0 0 1 0 0 0 0 0999 V2000 6.8253 -3.5787 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4426 -0.6746 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0892 0.0382 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 8.0021 -1.3550 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.5014 -0.9804 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8247 -0.6240 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8683 0.0001 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9342 -1.6179 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4869 -0.4180 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9343 0.5394 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0001 -1.0786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7629 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1479 -0.2676 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0311 -2.6107 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.8190 -2.2166 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7659 -0.3182 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5040 -1.3162 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.7629 -1.4971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5290 -1.4601 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8684 -1.0787 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 8.6019 -2.8220 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.5055 -2.2152 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.7430 -2.1924 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.1594 -1.0304 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.6607 0.3814 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3544 -2.2543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1991 -0.1591 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 14 1 0 0 0 0 2 4 2 0 0 0 0 2 5 1 0 0 0 0 3 6 1 0 0 0 0 3 13 2 0 0 0 0 4 15 1 0 0 0 0 5 16 2 0 0 0 0 6 17 2 0 0 0 0 7 10 1 0 0 0 0 7 20 1 0 0 0 0 8 11 1 0 0 0 0 8 20 1 0 0 0 0 9 12 1 0 0 0 0 9 20 1 0 0 0 0 10 21 1 0 0 0 0 11 21 1 0 0 0 0 12 21 1 0 0 0 0 13 25 1 0 0 0 0 14 15 2 0 0 0 0 14 16 1 0 0 0 0 15 22 1 0 0 0 0 16 27 1 0 0 0 0 17 18 1 0 0 0 0 17 27 1 0 0 0 0 18 23 2 0 0 0 0 18 25 1 0 0 0 0 19 24 2 0 0 0 0 19 25 1 0 0 0 0 20 19 1 1 0 0 0 21 26 1 1 0 0 0 23 24 1 0 0 0 0 26 28 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB004190
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	383.14
ALogP	1.0844
MLogP	3.11
XLogP	5.023
HDA	4
HBD	1
Rotatable Bonds	6
TPSA	59.65
RO5 Violation	1