NPASS drugs

Drug Information

Drug ID:	NPD4483
Drug Name:	rilmakalim
Molecular Formula:	C21H23NO5S
Canonical SMILES:	O=C1CCCN1[C@@H]1c2cc(ccc2OC([C@H]1O)(C)C)S(=O)(=O)c1ccccc1
Standard InCHI:	InChI=1S/C21H23NO5S/c1-21(2)20(24)19(22-12-6-9-18(22)23)16-13-15(10-11-17(16)27-21)28(25,26)14-7-4-3-5-8-14/h3-5,7-8,10-11,13,19-20,24H,6,9,12H2,1-2H3/t19-,20+/m1/s1
Standard InCHIKey:	LKAQWOWWTKFLNX-UXHICEINSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD4483

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	166
0.1-0.2	1070
0.2-0.3	3678
0.3-0.4	9314
0.4-0.5	5330
0.5-0.6	10510
0.6-0.7	820
0.7-0.8	2
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	0.7542	NPC469479
Intermediate Similarity	0.7363	NPC469505
Remote Similarity	0.6977	NPC307682
Remote Similarity	0.6914	NPC204546
Remote Similarity	0.6882	NPC254700
Remote Similarity	0.6868	NPC203424
Remote Similarity	0.6868	NPC206372
Remote Similarity	0.6857	NPC251439
Remote Similarity	0.6771	NPC2314
Remote Similarity	0.6765	NPC283079
Remote Similarity	0.676	NPC189908
Remote Similarity	0.6755	NPC233650
Remote Similarity	0.6743	NPC231163
Remote Similarity	0.6743	NPC318591
Remote Similarity	0.6737	NPC210140
Remote Similarity	0.672	NPC134858
Remote Similarity	0.6703	NPC477565
Remote Similarity	0.6703	NPC103379
Remote Similarity	0.6701	NPC149571
Remote Similarity	0.6686	NPC141739
Remote Similarity	0.6686	NPC136112
Remote Similarity	0.6685	NPC476151
Remote Similarity	0.6683	NPC308709
Remote Similarity	0.6667	NPC147091
Remote Similarity	0.665	NPC315542
Remote Similarity	0.6649	NPC150879
Remote Similarity	0.6648	NPC193528
Remote Similarity	0.6618	NPC477527
Remote Similarity	0.6615	NPC474470
Remote Similarity	0.6614	NPC313375
Remote Similarity	0.6614	NPC314725
Remote Similarity	0.6613	NPC127674
Remote Similarity	0.6613	NPC54379
Remote Similarity	0.6613	NPC5238
Remote Similarity	0.6613	NPC2413
Remote Similarity	0.6613	NPC204828
Remote Similarity	0.6613	NPC172765
Remote Similarity	0.6613	NPC249797
Remote Similarity	0.6613	NPC276588
Remote Similarity	0.6613	NPC39701
Remote Similarity	0.6613	NPC469817
Remote Similarity	0.6613	NPC295691
Remote Similarity	0.6613	NPC184026
Remote Similarity	0.6613	NPC110416
Remote Similarity	0.6613	NPC278799
Remote Similarity	0.6613	NPC207757
Remote Similarity	0.6613	NPC193949
Remote Similarity	0.6613	NPC189266
Remote Similarity	0.66	NPC283207
Remote Similarity	0.6597	NPC329717
Remote Similarity	0.6596	NPC59028
Remote Similarity	0.6596	NPC92191
Remote Similarity	0.6595	NPC471073
Remote Similarity	0.6595	NPC270811
Remote Similarity	0.6583	NPC329731
Remote Similarity	0.6578	NPC160931
Remote Similarity	0.6578	NPC37205
Remote Similarity	0.6575	NPC313414
Remote Similarity	0.6567	NPC477526
Remote Similarity	0.6566	NPC206061
Remote Similarity	0.6561	NPC205167
Remote Similarity	0.6557	NPC428
Remote Similarity	0.6557	NPC24233
Remote Similarity	0.6557	NPC147390
Remote Similarity	0.6557	NPC476571
Remote Similarity	0.6557	NPC246587
Remote Similarity	0.6557	NPC135538
Remote Similarity	0.6552	NPC118419
Remote Similarity	0.655	NPC218323
Remote Similarity	0.6548	NPC220961
Remote Similarity	0.6548	NPC474745
Remote Similarity	0.6546	NPC225597
Remote Similarity	0.6546	NPC470739
Remote Similarity	0.6546	NPC477640
Remote Similarity	0.6545	NPC471651
Remote Similarity	0.6545	NPC232514
Remote Similarity	0.6545	NPC276944
Remote Similarity	0.6545	NPC238530
Remote Similarity	0.6543	NPC129603
Remote Similarity	0.6534	NPC11147
Remote Similarity	0.6533	NPC276120
Remote Similarity	0.6533	NPC262725
Remote Similarity	0.6528	NPC82533
Remote Similarity	0.6528	NPC290759
Remote Similarity	0.6528	NPC266176
Remote Similarity	0.6528	NPC158148
Remote Similarity	0.6528	NPC204908
Remote Similarity	0.6528	NPC83198
Remote Similarity	0.6517	NPC237579
Remote Similarity	0.6514	NPC266425
Remote Similarity	0.6513	NPC190783
Remote Similarity	0.6513	NPC152680
Remote Similarity	0.6513	NPC232386
Remote Similarity	0.6505	NPC26601
Remote Similarity	0.6503	NPC476144
Remote Similarity	0.6503	NPC51957
Remote Similarity	0.6503	NPC191376
Remote Similarity	0.6503	NPC223873
Remote Similarity	0.6503	NPC179825
Remote Similarity	0.6503	NPC16107
Remote Similarity	0.6503	NPC321505
Remote Similarity	0.6503	NPC210437
Remote Similarity	0.6503	NPC106295
Remote Similarity	0.65	NPC4910
Remote Similarity	0.6497	NPC106606
Remote Similarity	0.6497	NPC474325
Remote Similarity	0.6495	NPC164608
Remote Similarity	0.6495	NPC474475
Remote Similarity	0.6491	NPC320242
Remote Similarity	0.649	NPC311357
Remote Similarity	0.6488	NPC24228
Remote Similarity	0.6486	NPC274026
Remote Similarity	0.6485	NPC473407
Remote Similarity	0.6485	NPC473378
Remote Similarity	0.6484	NPC185838
Remote Similarity	0.6482	NPC102760
Remote Similarity	0.6482	NPC248642
Remote Similarity	0.648	NPC304675
Remote Similarity	0.6477	NPC151706
Remote Similarity	0.6477	NPC90194
Remote Similarity	0.6477	NPC475318
Remote Similarity	0.6477	NPC9687
Remote Similarity	0.6477	NPC475598
Remote Similarity	0.6477	NPC474787
Remote Similarity	0.6477	NPC260045
Remote Similarity	0.6477	NPC79465
Remote Similarity	0.6477	NPC476102
Remote Similarity	0.6477	NPC76785
Remote Similarity	0.6477	NPC49577
Remote Similarity	0.6477	NPC293377
Remote Similarity	0.6477	NPC474811
Remote Similarity	0.6477	NPC118099
Remote Similarity	0.6477	NPC273907
Remote Similarity	0.6477	NPC474855
Remote Similarity	0.6474	NPC249274
Remote Similarity	0.6474	NPC18402
Remote Similarity	0.6474	NPC46067
Remote Similarity	0.6473	NPC475654
Remote Similarity	0.6471	NPC477564
Remote Similarity	0.6471	NPC59827
Remote Similarity	0.6471	NPC2295
Remote Similarity	0.6471	NPC184933
Remote Similarity	0.6467	NPC7467
Remote Similarity	0.6465	NPC244554
Remote Similarity	0.6465	NPC32154
Remote Similarity	0.6458	NPC169743
Remote Similarity	0.6458	NPC231198
Remote Similarity	0.6458	NPC186617
Remote Similarity	0.6455	NPC78359
Remote Similarity	0.6455	NPC65490
Remote Similarity	0.6455	NPC315707
Remote Similarity	0.6455	NPC148014
Remote Similarity	0.6455	NPC40389
Remote Similarity	0.645	NPC475981
Remote Similarity	0.645	NPC156576
Remote Similarity	0.645	NPC474746
Remote Similarity	0.6447	NPC32064
Remote Similarity	0.6447	NPC241704
Remote Similarity	0.6447	NPC222524
Remote Similarity	0.6447	NPC237044
Remote Similarity	0.6444	NPC474915
Remote Similarity	0.6444	NPC213206
Remote Similarity	0.6444	NPC328750
Remote Similarity	0.6444	NPC188163
Remote Similarity	0.6443	NPC58766
Remote Similarity	0.6443	NPC241055
Remote Similarity	0.6443	NPC475686
Remote Similarity	0.6443	NPC130921
Remote Similarity	0.644	NPC94292
Remote Similarity	0.6439	NPC149962
Remote Similarity	0.6439	NPC477258
Remote Similarity	0.6436	NPC216459
Remote Similarity	0.6436	NPC41178
Remote Similarity	0.6436	NPC138487
Remote Similarity	0.6436	NPC150670
Remote Similarity	0.6432	NPC473562
Remote Similarity	0.6429	NPC321133
Remote Similarity	0.6429	NPC136951
Remote Similarity	0.6429	NPC161155
Remote Similarity	0.6429	NPC97004
Remote Similarity	0.6425	NPC231572
Remote Similarity	0.6425	NPC474858
Remote Similarity	0.6425	NPC124657
Remote Similarity	0.6425	NPC123859
Remote Similarity	0.6421	NPC186595
Remote Similarity	0.6417	NPC82285
Remote Similarity	0.6417	NPC133011
Remote Similarity	0.6414	NPC294790
Remote Similarity	0.6414	NPC118633
Remote Similarity	0.6414	NPC329816
Remote Similarity	0.6414	NPC148693
Remote Similarity	0.6413	NPC253883
Remote Similarity	0.6413	NPC90844
Remote Similarity	0.6413	NPC95075
Remote Similarity	0.641	NPC311991
Remote Similarity	0.6408	NPC144314
Remote Similarity	0.6406	NPC218614
Remote Similarity	0.6402	NPC186063
Remote Similarity	0.6402	NPC133817
Remote Similarity	0.6402	NPC146288

Drug Structure

NPD4483 OpenBabel08211705262D 29 32 0 0 1 0 0 0 0 0999 V2000 1.3660 5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 5.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1808 2.1636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6808 1.2976 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 3.5116 2.9067 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 -1.0000 -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 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 2.7026 1.5055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 3.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.7321 4.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 2.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 1.9595 0.8363 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 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 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 4.0000 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 3.4641 4.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 21 1 0 0 0 0 2 21 1 0 0 0 0 3 4 2 0 0 0 0 3 5 1 0 0 0 0 4 7 1 0 0 0 0 5 8 2 0 0 0 0 6 9 1 0 0 0 0 6 12 1 0 0 0 0 7 14 2 0 0 0 0 8 14 1 0 0 0 0 9 18 1 0 0 0 0 10 11 2 0 0 0 0 10 15 1 0 0 0 0 11 17 1 0 0 0 0 12 22 1 0 0 0 0 13 15 2 0 0 0 0 13 16 1 0 0 0 0 14 28 1 0 0 0 0 15 28 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 27 1 0 0 0 0 18 22 1 0 0 0 0 18 23 2 0 0 0 0 19 20 1 0 0 0 0 19 22 1 6 0 0 0 20 21 1 0 0 0 0 20 24 1 1 0 0 0 21 27 1 0 0 0 0 24 29 1 0 0 0 0 25 28 2 0 0 0 0 26 28 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB000262
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	401.13
ALogP	-1.4227
MLogP	3
XLogP	2.902
HDA	5
HBD	1
Rotatable Bonds	6
TPSA	92.29
RO5 Violation	0