NPASS drugs

Drug Information

Drug ID:	NPD5100
Drug Name:	Losmapimod
Molecular Formula:	C22H26FN3O2
Canonical SMILES:	Fc1cc(cc(c1C)c1ccc(cn1)C(=NCC(C)(C)C)O)C(=NC1CC1)O
Standard InCHI:	InChI=1S/C22H26FN3O2/c1-13-17(9-15(10-18(13)23)21(28)26-16-6-7-16)19-8-5-14(11-24-19)20(27)25-12-22(2,3)4/h5,8-11,16H,6-7,12H2,1-4H3,(H,25,27)(H,26,28)
Standard InCHIKey:	KKYABQBFGDZVNQ-UHFFFAOYSA-N
Max Developmental Stage:	Phase 3
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD5100

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	329
0.1-0.2	1671
0.2-0.3	9818
0.3-0.4	12024
0.4-0.5	3918
0.5-0.6	1577
0.6-0.7	1277
0.7-0.8	275
0.8-0.85	1
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	0.8012	NPC98187
Intermediate Similarity	0.7976	NPC129721
Intermediate Similarity	0.7943	NPC203754
Intermediate Similarity	0.7943	NPC150048
Intermediate Similarity	0.7874	NPC158129
Intermediate Similarity	0.7857	NPC95783
Intermediate Similarity	0.7791	NPC473057
Intermediate Similarity	0.7791	NPC194640
Intermediate Similarity	0.7778	NPC131718
Intermediate Similarity	0.7746	NPC471178
Intermediate Similarity	0.7727	NPC313791
Intermediate Similarity	0.7701	NPC474561
Intermediate Similarity	0.7701	NPC49954
Intermediate Similarity	0.7688	NPC97367
Intermediate Similarity	0.7643	NPC212125
Intermediate Similarity	0.764	NPC134586
Intermediate Similarity	0.763	NPC282231
Intermediate Similarity	0.763	NPC124542
Intermediate Similarity	0.763	NPC59779
Intermediate Similarity	0.763	NPC471177
Intermediate Similarity	0.76	NPC160105
Intermediate Similarity	0.7598	NPC211997
Intermediate Similarity	0.7586	NPC102423
Intermediate Similarity	0.7584	NPC139763
Intermediate Similarity	0.7572	NPC279918
Intermediate Similarity	0.7562	NPC256893
Intermediate Similarity	0.7557	NPC63751
Intermediate Similarity	0.754	NPC329541
Intermediate Similarity	0.7528	NPC471294
Intermediate Similarity	0.7528	NPC314603
Intermediate Similarity	0.7527	NPC48938
Intermediate Similarity	0.7527	NPC19679
Intermediate Similarity	0.75	NPC326575
Intermediate Similarity	0.7485	NPC471323
Intermediate Similarity	0.7485	NPC469760
Intermediate Similarity	0.7485	NPC469763
Intermediate Similarity	0.7485	NPC73952
Intermediate Similarity	0.7485	NPC469765
Intermediate Similarity	0.7485	NPC469786
Intermediate Similarity	0.7485	NPC25008
Intermediate Similarity	0.7485	NPC259644
Intermediate Similarity	0.7459	NPC46580
Intermediate Similarity	0.7459	NPC248462
Intermediate Similarity	0.7458	NPC201700
Intermediate Similarity	0.7446	NPC62510
Intermediate Similarity	0.7446	NPC314002
Intermediate Similarity	0.7442	NPC75540
Intermediate Similarity	0.7442	NPC207726
Intermediate Similarity	0.7442	NPC212376
Intermediate Similarity	0.7442	NPC211572
Intermediate Similarity	0.7442	NPC80597
Intermediate Similarity	0.7442	NPC70922
Intermediate Similarity	0.743	NPC259545
Intermediate Similarity	0.7429	NPC16667
Intermediate Similarity	0.7421	NPC471313
Intermediate Similarity	0.7421	NPC471311
Intermediate Similarity	0.7421	NPC224928
Intermediate Similarity	0.7421	NPC306397
Intermediate Similarity	0.7416	NPC314940
Intermediate Similarity	0.7416	NPC280548
Intermediate Similarity	0.7416	NPC473764
Intermediate Similarity	0.7414	NPC230869
Intermediate Similarity	0.7409	NPC328318
Intermediate Similarity	0.7409	NPC328596
Intermediate Similarity	0.7405	NPC171171
Intermediate Similarity	0.7403	NPC151939
Intermediate Similarity	0.7401	NPC54988
Intermediate Similarity	0.7401	NPC108469
Intermediate Similarity	0.7399	NPC285469
Intermediate Similarity	0.7394	NPC99666
Intermediate Similarity	0.7391	NPC204717
Intermediate Similarity	0.7391	NPC207851
Intermediate Similarity	0.7386	NPC311276
Intermediate Similarity	0.7378	NPC29702
Intermediate Similarity	0.7368	NPC105818
Intermediate Similarity	0.7368	NPC24678
Intermediate Similarity	0.7365	NPC60553
Intermediate Similarity	0.7363	NPC176199
Intermediate Similarity	0.7363	NPC215795
Intermediate Similarity	0.7363	NPC472443
Intermediate Similarity	0.7363	NPC232340
Intermediate Similarity	0.7356	NPC469762
Intermediate Similarity	0.7346	NPC324611
Intermediate Similarity	0.7337	NPC220765
Intermediate Similarity	0.7333	NPC314102
Intermediate Similarity	0.7333	NPC34508
Intermediate Similarity	0.7333	NPC251722
Intermediate Similarity	0.7333	NPC475070
Intermediate Similarity	0.733	NPC315214
Intermediate Similarity	0.733	NPC47298
Intermediate Similarity	0.733	NPC229332
Intermediate Similarity	0.7318	NPC194411
Intermediate Similarity	0.7316	NPC133366
Intermediate Similarity	0.7314	NPC67056
Intermediate Similarity	0.7312	NPC165370
Intermediate Similarity	0.7308	NPC248454
Intermediate Similarity	0.7308	NPC59269
Intermediate Similarity	0.7302	NPC195268
Intermediate Similarity	0.7302	NPC133140
Intermediate Similarity	0.7299	NPC141353
Intermediate Similarity	0.7299	NPC469785
Intermediate Similarity	0.7297	NPC284559
Intermediate Similarity	0.7296	NPC317373
Intermediate Similarity	0.7289	NPC169433
Intermediate Similarity	0.7288	NPC32028
Intermediate Similarity	0.7288	NPC159319
Intermediate Similarity	0.7288	NPC476118
Intermediate Similarity	0.7273	NPC25899
Intermediate Similarity	0.7273	NPC317030
Intermediate Similarity	0.7273	NPC204565
Intermediate Similarity	0.7268	NPC133261
Intermediate Similarity	0.7268	NPC213468
Intermediate Similarity	0.7263	NPC474177
Intermediate Similarity	0.7253	NPC472122
Intermediate Similarity	0.7253	NPC24594
Intermediate Similarity	0.725	NPC112206
Intermediate Similarity	0.725	NPC202605
Intermediate Similarity	0.7245	NPC327592
Intermediate Similarity	0.7243	NPC472444
Intermediate Similarity	0.7243	NPC133306
Intermediate Similarity	0.7235	NPC314372
Intermediate Similarity	0.7235	NPC159856
Intermediate Similarity	0.7234	NPC65215
Intermediate Similarity	0.7234	NPC173028
Intermediate Similarity	0.7232	NPC177404
Intermediate Similarity	0.7231	NPC57398
Intermediate Similarity	0.7228	NPC300688
Intermediate Similarity	0.7222	NPC477111
Intermediate Similarity	0.7219	NPC474707
Intermediate Similarity	0.7216	NPC84508
Intermediate Similarity	0.7213	NPC64436
Intermediate Similarity	0.7213	NPC68354
Intermediate Similarity	0.7209	NPC187951
Intermediate Similarity	0.7207	NPC41717
Intermediate Similarity	0.7204	NPC284678
Intermediate Similarity	0.7204	NPC165495
Intermediate Similarity	0.7202	NPC212213
Intermediate Similarity	0.72	NPC208284
Intermediate Similarity	0.72	NPC51054
Intermediate Similarity	0.7198	NPC275305
Intermediate Similarity	0.7198	NPC37423
Intermediate Similarity	0.7196	NPC3715
Intermediate Similarity	0.7194	NPC53144
Intermediate Similarity	0.7191	NPC472587
Intermediate Similarity	0.7189	NPC233936
Intermediate Similarity	0.7182	NPC252590
Intermediate Similarity	0.7175	NPC81229
Intermediate Similarity	0.7175	NPC255229
Intermediate Similarity	0.7174	NPC270009
Intermediate Similarity	0.717	NPC46358
Intermediate Similarity	0.7169	NPC328029
Intermediate Similarity	0.7167	NPC317430
Intermediate Similarity	0.7166	NPC15102
Intermediate Similarity	0.7165	NPC4071
Intermediate Similarity	0.7165	NPC32200
Intermediate Similarity	0.7165	NPC476167
Intermediate Similarity	0.7165	NPC476582
Intermediate Similarity	0.7165	NPC476578
Intermediate Similarity	0.7158	NPC473763
Intermediate Similarity	0.7158	NPC267885
Intermediate Similarity	0.7158	NPC117244
Intermediate Similarity	0.7157	NPC476581
Intermediate Similarity	0.7157	NPC329708
Intermediate Similarity	0.7157	NPC118832
Intermediate Similarity	0.7157	NPC165349
Intermediate Similarity	0.7157	NPC16452
Intermediate Similarity	0.7157	NPC264166
Intermediate Similarity	0.7157	NPC274291
Intermediate Similarity	0.7157	NPC47059
Intermediate Similarity	0.7157	NPC36229
Intermediate Similarity	0.7151	NPC470508
Intermediate Similarity	0.7151	NPC163055
Intermediate Similarity	0.715	NPC5145
Intermediate Similarity	0.715	NPC77555
Intermediate Similarity	0.7143	NPC211813
Intermediate Similarity	0.7143	NPC472123
Intermediate Similarity	0.7143	NPC38736
Intermediate Similarity	0.7143	NPC128751
Intermediate Similarity	0.7135	NPC15840
Intermediate Similarity	0.7135	NPC48192
Intermediate Similarity	0.7135	NPC187827
Intermediate Similarity	0.7135	NPC472105
Intermediate Similarity	0.7127	NPC126481
Intermediate Similarity	0.7126	NPC470233
Intermediate Similarity	0.712	NPC141915
Intermediate Similarity	0.712	NPC114335
Intermediate Similarity	0.712	NPC184964
Intermediate Similarity	0.712	NPC324149
Intermediate Similarity	0.712	NPC96890
Intermediate Similarity	0.712	NPC293472
Intermediate Similarity	0.712	NPC280964
Intermediate Similarity	0.7119	NPC56765
Intermediate Similarity	0.7119	NPC135141
Intermediate Similarity	0.7119	NPC92796
Intermediate Similarity	0.7118	NPC190296
Intermediate Similarity	0.7113	NPC102008
Intermediate Similarity	0.7113	NPC474916
Intermediate Similarity	0.7113	NPC192315
Intermediate Similarity	0.711	NPC37548
Intermediate Similarity	0.7107	NPC200836

Drug Structure

NPD5100 OpenBabel08211706322D 30 32 0 0 0 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 3.0981 -5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -5.0000 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 -5.6962 -2.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.1962 -2.0000 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 -2.5981 -0.5000 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 0.8660 -0.5000 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 -1.7321 1.0000 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 -3.4641 -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 -1.7321 -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 -0.8660 -0.5000 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 -4.3301 -0.5000 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 -2.5981 2.5000 0.0000 F 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 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 -4.3301 -1.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 22 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 8 2 0 0 0 0 5 14 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 0 0 0 0 7 16 1 0 0 0 0 8 19 1 0 0 0 0 9 15 2 0 0 0 0 9 17 1 0 0 0 0 10 15 1 0 0 0 0 10 18 2 0 0 0 0 11 14 2 0 0 0 0 11 24 1 0 0 0 0 12 22 1 0 0 0 0 12 25 1 0 0 0 0 13 17 2 0 0 0 0 13 18 1 0 0 0 0 14 20 1 0 0 0 0 15 21 1 0 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 18 23 1 0 0 0 0 19 24 2 0 0 0 0 20 25 2 3 0 0 0 20 27 1 0 0 0 0 21 26 2 3 0 0 0 21 28 1 0 0 0 0 27 29 1 0 0 0 0 28 30 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000554
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	11552706
ChEBI
CAS Number

Drug Properties

Molecular Weight	383.20
ALogP	1.5636
MLogP	3.22
XLogP	4.792
HDA	5
HBD	2
Rotatable Bonds	13
TPSA	78.07
RO5 Violation	0