NPASS drugs

Drug Information

Drug ID:	NPD8357
Drug Name:	Rifaximin
Molecular Formula:	C43H51N3O11
Canonical SMILES:	CO[C@H]1/C=C/O[C@@]2(C)Oc3c(C2=O)c2c(c(c3C)O)c(O)c(c3c2nc2n3ccc(c2)C)N=C(/C(=CC=C[C@@H]([C@@H]([C@H]([C@H]([C@H]([C@@H]([C@@H]1C)OC(=O)C)C)O)C)O)C)/C)O
Standard InCHI:	InChI=1S/C43H51N3O11/c1-19-14-16-46-28(18-19)44-32-29-30-37(50)25(7)40-31(29)41(52)43(9,57-40)55-17-15-27(54-10)22(4)39(56-26(8)47)24(6)36(49)23(5)35(48)20(2)12-11-13-21(3)42(53)45-33(34(32)46)38(30)51/h11-18,20,22-24,27,35-36,39,48-51H,1-10H3,(H,45,53)/b12-11+,17-15+,21-13-/t20-,22+,23+,24+,27-,35-,36+,39+,43-/m0/s1
Standard InCHIKey:	NZCRJKRKKOLAOJ-XRCRFVBUSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD8357

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	495
0.1-0.2	2249
0.2-0.3	8040
0.3-0.4	6864
0.4-0.5	10060
0.5-0.6	2823
0.6-0.7	354
0.7-0.8	5
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	0.7393	NPC317567
Intermediate Similarity	0.7164	NPC227033
Intermediate Similarity	0.7028	NPC472067
Intermediate Similarity	0.7028	NPC472066
Intermediate Similarity	0.7028	NPC472031
Remote Similarity	0.6899	NPC472068
Remote Similarity	0.6879	NPC101312
Remote Similarity	0.6857	NPC179896
Remote Similarity	0.6835	NPC227824
Remote Similarity	0.6801	NPC88923
Remote Similarity	0.6801	NPC100734
Remote Similarity	0.6801	NPC315634
Remote Similarity	0.6791	NPC230683
Remote Similarity	0.6746	NPC129897
Remote Similarity	0.6737	NPC6786
Remote Similarity	0.6713	NPC30540
Remote Similarity	0.6689	NPC279589
Remote Similarity	0.6667	NPC45048
Remote Similarity	0.6667	NPC191489
Remote Similarity	0.6656	NPC237901
Remote Similarity	0.6656	NPC195788
Remote Similarity	0.6655	NPC137353
Remote Similarity	0.6655	NPC67401
Remote Similarity	0.6633	NPC284685
Remote Similarity	0.6631	NPC314987
Remote Similarity	0.662	NPC472061
Remote Similarity	0.6611	NPC89549
Remote Similarity	0.6607	NPC251071
Remote Similarity	0.6593	NPC207620
Remote Similarity	0.6572	NPC169716
Remote Similarity	0.657	NPC260909
Remote Similarity	0.6567	NPC209981
Remote Similarity	0.6566	NPC472589
Remote Similarity	0.6566	NPC318068
Remote Similarity	0.6564	NPC291609
Remote Similarity	0.6556	NPC470042
Remote Similarity	0.6542	NPC183537
Remote Similarity	0.6529	NPC124300
Remote Similarity	0.6522	NPC472436
Remote Similarity	0.652	NPC189079
Remote Similarity	0.6519	NPC310618
Remote Similarity	0.6519	NPC72715
Remote Similarity	0.6516	NPC314222
Remote Similarity	0.6516	NPC196449
Remote Similarity	0.6514	NPC187145
Remote Similarity	0.6512	NPC471978
Remote Similarity	0.65	NPC185197
Remote Similarity	0.65	NPC473833
Remote Similarity	0.6498	NPC329982
Remote Similarity	0.6498	NPC472588
Remote Similarity	0.6497	NPC1608
Remote Similarity	0.6478	NPC282346
Remote Similarity	0.6477	NPC478045
Remote Similarity	0.6477	NPC469439
Remote Similarity	0.6473	NPC72905
Remote Similarity	0.6455	NPC120513
Remote Similarity	0.6455	NPC13603
Remote Similarity	0.6447	NPC471979
Remote Similarity	0.6446	NPC474701
Remote Similarity	0.6438	NPC473639
Remote Similarity	0.6438	NPC475844
Remote Similarity	0.6431	NPC473800
Remote Similarity	0.6431	NPC77878
Remote Similarity	0.6431	NPC133609
Remote Similarity	0.6424	NPC215837
Remote Similarity	0.6421	NPC303374
Remote Similarity	0.6421	NPC53255
Remote Similarity	0.6421	NPC472435
Remote Similarity	0.6421	NPC475301
Remote Similarity	0.6421	NPC85879
Remote Similarity	0.6421	NPC326930
Remote Similarity	0.6418	NPC174760
Remote Similarity	0.6403	NPC328928
Remote Similarity	0.6396	NPC280799
Remote Similarity	0.6395	NPC477795
Remote Similarity	0.6395	NPC142385
Remote Similarity	0.6395	NPC477796
Remote Similarity	0.6395	NPC477805
Remote Similarity	0.6395	NPC477806
Remote Similarity	0.6389	NPC474688
Remote Similarity	0.6385	NPC218388
Remote Similarity	0.6382	NPC99891
Remote Similarity	0.6382	NPC132385
Remote Similarity	0.6373	NPC124313
Remote Similarity	0.6364	NPC173250
Remote Similarity	0.6364	NPC270515
Remote Similarity	0.6351	NPC469734
Remote Similarity	0.6351	NPC178858
Remote Similarity	0.6348	NPC304837
Remote Similarity	0.6348	NPC41501
Remote Similarity	0.6348	NPC476258
Remote Similarity	0.6345	NPC329631
Remote Similarity	0.6342	NPC203373
Remote Similarity	0.634	NPC315467
Remote Similarity	0.6333	NPC473441
Remote Similarity	0.6333	NPC131273
Remote Similarity	0.6333	NPC244543
Remote Similarity	0.633	NPC107836
Remote Similarity	0.6329	NPC473449
Remote Similarity	0.6327	NPC210296
Remote Similarity	0.6319	NPC274640
Remote Similarity	0.6314	NPC166722
Remote Similarity	0.6312	NPC169402
Remote Similarity	0.6312	NPC478080
Remote Similarity	0.631	NPC474192
Remote Similarity	0.631	NPC475720
Remote Similarity	0.6305	NPC207283
Remote Similarity	0.6305	NPC84164
Remote Similarity	0.6303	NPC150239
Remote Similarity	0.6301	NPC473187
Remote Similarity	0.6296	NPC107123
Remote Similarity	0.6294	NPC51388
Remote Similarity	0.6293	NPC168922
Remote Similarity	0.6288	NPC51854
Remote Similarity	0.6286	NPC472098
Remote Similarity	0.6284	NPC188400
Remote Similarity	0.6284	NPC15406
Remote Similarity	0.6281	NPC198503
Remote Similarity	0.6279	NPC471015
Remote Similarity	0.6277	NPC3207
Remote Similarity	0.6276	NPC477531
Remote Similarity	0.6272	NPC97746
Remote Similarity	0.6271	NPC63109
Remote Similarity	0.6267	NPC473188
Remote Similarity	0.6266	NPC478009
Remote Similarity	0.6266	NPC478010
Remote Similarity	0.6263	NPC252251
Remote Similarity	0.6263	NPC160898
Remote Similarity	0.6259	NPC46970
Remote Similarity	0.6259	NPC474183
Remote Similarity	0.6254	NPC9729
Remote Similarity	0.6254	NPC132329
Remote Similarity	0.625	NPC74619
Remote Similarity	0.625	NPC200888
Remote Similarity	0.625	NPC470018
Remote Similarity	0.625	NPC477395
Remote Similarity	0.625	NPC202503
Remote Similarity	0.6242	NPC58209
Remote Similarity	0.6242	NPC120239
Remote Similarity	0.6241	NPC116238
Remote Similarity	0.6241	NPC209174
Remote Similarity	0.6238	NPC478083
Remote Similarity	0.6237	NPC475816
Remote Similarity	0.6233	NPC473105
Remote Similarity	0.6233	NPC134637
Remote Similarity	0.6232	NPC247803
Remote Similarity	0.6232	NPC46561
Remote Similarity	0.6229	NPC208364
Remote Similarity	0.6224	NPC476995
Remote Similarity	0.6221	NPC475315
Remote Similarity	0.6221	NPC324619
Remote Similarity	0.6221	NPC477396
Remote Similarity	0.6221	NPC152620
Remote Similarity	0.622	NPC160666
Remote Similarity	0.622	NPC316065
Remote Similarity	0.622	NPC289905
Remote Similarity	0.6218	NPC471303
Remote Similarity	0.6216	NPC119134
Remote Similarity	0.6215	NPC179287
Remote Similarity	0.6215	NPC21638
Remote Similarity	0.6214	NPC314834
Remote Similarity	0.6213	NPC302807
Remote Similarity	0.6212	NPC263937
Remote Similarity	0.6212	NPC94428
Remote Similarity	0.6212	NPC476220
Remote Similarity	0.6212	NPC160113
Remote Similarity	0.6208	NPC472434
Remote Similarity	0.6208	NPC477393
Remote Similarity	0.6208	NPC311451
Remote Similarity	0.6208	NPC208522
Remote Similarity	0.6207	NPC237978
Remote Similarity	0.6203	NPC473565
Remote Similarity	0.6202	NPC144452
Remote Similarity	0.62	NPC91868
Remote Similarity	0.62	NPC63971
Remote Similarity	0.6199	NPC233334
Remote Similarity	0.6197	NPC478006
Remote Similarity	0.6195	NPC171393
Remote Similarity	0.6195	NPC295452
Remote Similarity	0.6194	NPC227908
Remote Similarity	0.619	NPC108342
Remote Similarity	0.6189	NPC128115
Remote Similarity	0.6187	NPC475533
Remote Similarity	0.6182	NPC471782
Remote Similarity	0.6182	NPC471583
Remote Similarity	0.6182	NPC253482
Remote Similarity	0.6179	NPC165964
Remote Similarity	0.6177	NPC220852
Remote Similarity	0.6176	NPC216507
Remote Similarity	0.6176	NPC472842
Remote Similarity	0.6174	NPC475648
Remote Similarity	0.6174	NPC160100
Remote Similarity	0.6172	NPC314882
Remote Similarity	0.6172	NPC471513
Remote Similarity	0.6172	NPC140296
Remote Similarity	0.6172	NPC473458
Remote Similarity	0.617	NPC264176
Remote Similarity	0.617	NPC38237
Remote Similarity	0.617	NPC305542
Remote Similarity	0.617	NPC48353

Drug Structure

NPD8357 OpenBabel08211713012D 62 67 0 0 1 0 0 0 0 0999 V2000 3.1810 -2.7645 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0007 -4.4464 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4542 -4.9013 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6440 0.4397 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0989 -3.0153 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3343 -1.2269 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2435 1.9235 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1158 0.9772 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2627 1.5947 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6316 1.9740 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2083 -4.1805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8438 -4.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5504 -4.1805 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6549 -3.4439 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8438 0.6467 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6957 -3.3431 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2083 0.8170 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8295 -1.7826 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2218 -2.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4136 -3.6812 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0851 -4.0102 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8788 -0.1475 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.2078 -2.6462 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.3781 -1.3528 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.2870 -0.0050 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2247 0.6081 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4136 0.3178 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 0.8703 -1.6817 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4491 -0.7173 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2844 -1.1995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1202 -0.1475 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6139 -1.1995 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4491 -2.6462 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6139 -2.1640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8788 -3.2160 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3781 -2.0107 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0733 -0.3621 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2844 -2.1640 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2078 -0.7173 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.5175 -0.3971 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6549 0.3178 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6549 -3.6812 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0851 0.6467 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3034 -0.9015 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.1202 -3.2160 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.3034 -2.4620 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.4596 1.1952 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6440 -3.8031 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3343 -2.1366 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8136 0.2561 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1196 -2.6462 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2421 1.0829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.2421 -4.4464 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0007 1.0829 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5504 0.8170 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0989 -0.3482 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5181 -4.7594 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9214 -1.3714 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7192 -0.0760 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9549 -2.1640 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1983 -4.3205 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 19 1 0 0 0 0 3 21 1 0 0 0 0 7 25 1 0 0 0 0 8 26 1 0 0 0 0 10 54 1 0 0 0 0 11 12 2 0 0 0 0 11 13 1 0 0 0 0 12 20 1 0 0 0 0 13 21 2 0 0 0 0 14 16 2 0 0 0 0 14 19 1 0 0 0 0 15 17 2 0 0 0 0 15 27 1 0 0 0 0 16 46 1 0 0 0 0 17 55 1 0 0 0 0 18 19 2 0 0 0 0 18 28 1 0 0 0 0 20 2 1 1 0 0 0 20 35 1 0 0 0 0 21 42 1 0 0 0 0 22 4 1 1 0 0 0 22 27 1 0 0 0 0 22 39 1 0 0 0 0 23 5 1 6 0 0 0 23 35 1 0 0 0 0 23 36 1 0 0 0 0 24 6 1 6 0 0 0 24 36 1 0 0 0 0 24 39 1 0 0 0 0 25 37 2 0 0 0 0 25 40 1 0 0 0 0 26 47 2 0 0 0 0 26 56 1 0 0 0 0 27 54 1 6 0 0 0 28 44 2 0 0 0 0 28 46 1 0 0 0 0 29 30 2 0 0 0 0 29 31 1 0 0 0 0 29 32 1 0 0 0 0 30 37 1 0 0 0 0 30 38 1 0 0 0 0 31 40 2 0 0 0 0 31 41 1 0 0 0 0 32 34 2 0 0 0 0 32 44 1 0 0 0 0 33 34 1 0 0 0 0 33 38 2 0 0 0 0 33 45 1 0 0 0 0 34 46 1 0 0 0 0 35 48 1 1 0 0 0 36 49 1 6 0 0 0 37 50 1 0 0 0 0 38 51 1 0 0 0 0 39 56 1 1 0 0 0 40 57 1 0 0 0 0 41 43 1 0 0 0 0 41 52 2 0 0 0 0 42 45 2 3 0 0 0 42 53 1 0 0 0 0 43 9 1 6 0 0 0 43 55 1 0 0 0 0 43 57 1 0 0 0 0 48 58 1 0 0 0 0 49 59 1 0 0 0 0 50 60 1 0 0 0 0 51 61 1 0 0 0 0 53 62 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB001908; DAP001006
DrugBank	DB01220
ChEMBL	CHEMBL1617
IUPHAR/BPS
PharmaGKB	PA164752443
KEGG Drug	D02554
PubChem CID
ChEBI	75246
CAS Number	80621-81-4

Drug Properties

Molecular Weight	785.35
ALogP	0.6205
MLogP	4.65
XLogP	3.805
HDA	11
HBD	5
Rotatable Bonds	18
TPSA	202.39
RO5 Violation	1