NPASS drugs

Drug Information

Drug ID:	NPD4161
Drug Name:	amsilarotene
Molecular Formula:	C20H27NO3Si2
Canonical SMILES:	O=C(c1cc(cc(c1)[Si](C)(C)C)[Si](C)(C)C)Nc1ccc(cc1)C(=O)O
Standard InCHI:	InChI=1S/C20H27NO3Si2/c1-25(2,3)17-11-15(12-18(13-17)26(4,5)6)19(22)21-16-9-7-14(8-10-16)20(23)24/h7-13H,1-6H3,(H,21,22)(H,23,24)
Standard InCHIKey:	VVTNSTLJOVCBDL-UHFFFAOYSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD4161

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	154
0.1-0.2	1290
0.2-0.3	5181
0.3-0.4	8593
0.4-0.5	12082
0.5-0.6	3207
0.6-0.7	348
0.7-0.8	32
0.8-0.85	2
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	0.9007	NPC242933
Intermediate Similarity	0.844	NPC314098
Intermediate Similarity	0.8116	NPC150323
Intermediate Similarity	0.7958	NPC205946
Intermediate Similarity	0.7891	NPC253476
Intermediate Similarity	0.7647	NPC472241
Intermediate Similarity	0.7582	NPC43477
Intermediate Similarity	0.7516	NPC472243
Intermediate Similarity	0.75	NPC472242
Intermediate Similarity	0.747	NPC470971
Intermediate Similarity	0.7466	NPC472244
Intermediate Similarity	0.7466	NPC470343
Intermediate Similarity	0.7465	NPC229353
Intermediate Similarity	0.7451	NPC319645
Intermediate Similarity	0.7415	NPC314278
Intermediate Similarity	0.7368	NPC173295
Intermediate Similarity	0.7361	NPC130931
Intermediate Similarity	0.7305	NPC182131
Intermediate Similarity	0.7297	NPC322433
Intermediate Similarity	0.7241	NPC470317
Intermediate Similarity	0.7186	NPC189116
Intermediate Similarity	0.7161	NPC287358
Intermediate Similarity	0.7152	NPC472245
Intermediate Similarity	0.7143	NPC300596
Intermediate Similarity	0.7143	NPC237649
Intermediate Similarity	0.7108	NPC36495
Intermediate Similarity	0.7102	NPC471742
Intermediate Similarity	0.7099	NPC144691
Intermediate Similarity	0.7089	NPC301702
Intermediate Similarity	0.7086	NPC122235
Intermediate Similarity	0.7055	NPC314223
Intermediate Similarity	0.7055	NPC226143
Intermediate Similarity	0.7047	NPC226794
Intermediate Similarity	0.7039	NPC194562
Intermediate Similarity	0.7	NPC313293
Remote Similarity	0.6983	NPC473815
Remote Similarity	0.6977	NPC318183
Remote Similarity	0.6975	NPC315829
Remote Similarity	0.6974	NPC150863
Remote Similarity	0.6936	NPC73280
Remote Similarity	0.6933	NPC192533
Remote Similarity	0.6928	NPC314431
Remote Similarity	0.6928	NPC280807
Remote Similarity	0.6923	NPC199737
Remote Similarity	0.6919	NPC471778
Remote Similarity	0.6914	NPC478039
Remote Similarity	0.6914	NPC146370
Remote Similarity	0.6899	NPC181527
Remote Similarity	0.6892	NPC179605
Remote Similarity	0.6892	NPC279385
Remote Similarity	0.6879	NPC292265
Remote Similarity	0.6864	NPC27904
Remote Similarity	0.6857	NPC475607
Remote Similarity	0.6846	NPC103292
Remote Similarity	0.6842	NPC471130
Remote Similarity	0.6833	NPC160381
Remote Similarity	0.6832	NPC308197
Remote Similarity	0.6824	NPC88970
Remote Similarity	0.6818	NPC474081
Remote Similarity	0.6818	NPC14849
Remote Similarity	0.68	NPC475594
Remote Similarity	0.68	NPC328611
Remote Similarity	0.68	NPC248862
Remote Similarity	0.679	NPC314186
Remote Similarity	0.6784	NPC204867
Remote Similarity	0.6759	NPC57051
Remote Similarity	0.6746	NPC123241
Remote Similarity	0.6746	NPC61013
Remote Similarity	0.6743	NPC177261
Remote Similarity	0.6721	NPC83111
Remote Similarity	0.6707	NPC259678
Remote Similarity	0.6706	NPC193410
Remote Similarity	0.6705	NPC470548
Remote Similarity	0.6689	NPC268534
Remote Similarity	0.6687	NPC315224
Remote Similarity	0.6686	NPC474814
Remote Similarity	0.6686	NPC112336
Remote Similarity	0.6685	NPC474041
Remote Similarity	0.6685	NPC182057
Remote Similarity	0.6685	NPC475761
Remote Similarity	0.6685	NPC131450
Remote Similarity	0.6685	NPC147298
Remote Similarity	0.6667	NPC474926
Remote Similarity	0.6667	NPC248117
Remote Similarity	0.6667	NPC471743
Remote Similarity	0.6646	NPC315051
Remote Similarity	0.6645	NPC254698
Remote Similarity	0.6645	NPC209389
Remote Similarity	0.663	NPC5630
Remote Similarity	0.6628	NPC293458
Remote Similarity	0.6627	NPC242000
Remote Similarity	0.6625	NPC316574
Remote Similarity	0.6625	NPC159722
Remote Similarity	0.6611	NPC288305
Remote Similarity	0.6609	NPC472114
Remote Similarity	0.6609	NPC472115
Remote Similarity	0.6596	NPC141454
Remote Similarity	0.6595	NPC203628
Remote Similarity	0.6584	NPC238412
Remote Similarity	0.6579	NPC39818
Remote Similarity	0.657	NPC322644
Remote Similarity	0.657	NPC474058
Remote Similarity	0.6545	NPC471944
Remote Similarity	0.6543	NPC314252
Remote Similarity	0.6543	NPC303214
Remote Similarity	0.6543	NPC181526
Remote Similarity	0.6543	NPC204156
Remote Similarity	0.6541	NPC474473
Remote Similarity	0.6534	NPC469915
Remote Similarity	0.6516	NPC250476
Remote Similarity	0.6514	NPC471652
Remote Similarity	0.6513	NPC257490
Remote Similarity	0.6513	NPC39679
Remote Similarity	0.6512	NPC471122
Remote Similarity	0.6503	NPC2823
Remote Similarity	0.6503	NPC49184
Remote Similarity	0.65	NPC474815
Remote Similarity	0.65	NPC218594
Remote Similarity	0.65	NPC99043
Remote Similarity	0.6497	NPC126676
Remote Similarity	0.6497	NPC469671
Remote Similarity	0.6497	NPC477432
Remote Similarity	0.6494	NPC292143
Remote Similarity	0.6494	NPC139506
Remote Similarity	0.649	NPC291962
Remote Similarity	0.649	NPC177684
Remote Similarity	0.6488	NPC473329
Remote Similarity	0.6485	NPC130797
Remote Similarity	0.6485	NPC323798
Remote Similarity	0.6485	NPC190945
Remote Similarity	0.6484	NPC243058
Remote Similarity	0.6481	NPC83214
Remote Similarity	0.648	NPC84347
Remote Similarity	0.6479	NPC38262
Remote Similarity	0.6477	NPC224970
Remote Similarity	0.6477	NPC223595
Remote Similarity	0.6477	NPC167724
Remote Similarity	0.6474	NPC58827
Remote Similarity	0.6474	NPC307437
Remote Similarity	0.6474	NPC72473
Remote Similarity	0.6464	NPC475685
Remote Similarity	0.6456	NPC231382
Remote Similarity	0.6456	NPC316746
Remote Similarity	0.6448	NPC97584
Remote Similarity	0.6448	NPC203635
Remote Similarity	0.6447	NPC112373
Remote Similarity	0.6447	NPC258531
Remote Similarity	0.6447	NPC161956
Remote Similarity	0.6438	NPC162417
Remote Similarity	0.6438	NPC316104
Remote Similarity	0.6437	NPC253667
Remote Similarity	0.6437	NPC35510
Remote Similarity	0.6425	NPC303225
Remote Similarity	0.6424	NPC478040
Remote Similarity	0.6415	NPC476689
Remote Similarity	0.6415	NPC476685
Remote Similarity	0.6415	NPC476687
Remote Similarity	0.6414	NPC87413
Remote Similarity	0.6402	NPC471164
Remote Similarity	0.64	NPC298449
Remote Similarity	0.6398	NPC316405
Remote Similarity	0.6398	NPC221873
Remote Similarity	0.6392	NPC165599
Remote Similarity	0.6387	NPC317758
Remote Similarity	0.6379	NPC472102
Remote Similarity	0.6379	NPC309531
Remote Similarity	0.6379	NPC315368
Remote Similarity	0.6378	NPC90415
Remote Similarity	0.6378	NPC150308
Remote Similarity	0.6374	NPC298320
Remote Similarity	0.6373	NPC232600
Remote Similarity	0.6369	NPC191310
Remote Similarity	0.6364	NPC299582
Remote Similarity	0.6364	NPC471124
Remote Similarity	0.6364	NPC303951
Remote Similarity	0.6359	NPC301292
Remote Similarity	0.6359	NPC313112
Remote Similarity	0.6358	NPC153694
Remote Similarity	0.6358	NPC211525
Remote Similarity	0.6354	NPC186669
Remote Similarity	0.6354	NPC219848
Remote Similarity	0.6349	NPC45850
Remote Similarity	0.6348	NPC472118
Remote Similarity	0.6343	NPC99632
Remote Similarity	0.6343	NPC476231
Remote Similarity	0.6343	NPC282339
Remote Similarity	0.6332	NPC9894
Remote Similarity	0.6332	NPC23294
Remote Similarity	0.6328	NPC214960
Remote Similarity	0.6328	NPC279527
Remote Similarity	0.6327	NPC225400
Remote Similarity	0.6324	NPC322621
Remote Similarity	0.6319	NPC256268
Remote Similarity	0.6319	NPC43218
Remote Similarity	0.6319	NPC475094
Remote Similarity	0.6318	NPC118228
Remote Similarity	0.6313	NPC355
Remote Similarity	0.6307	NPC313757
Remote Similarity	0.6298	NPC129624
Remote Similarity	0.6298	NPC203202

Drug Structure

NPD4161 OpenBabel08211704332D 28 29 0 0 0 0 0 0 0 0999 V2000 0.0000 1.0000 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 2.1340 -2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5000 -2.5981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8660 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 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 3.0000 0.0000 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 5.5000 -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 4.5000 0.8660 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 2.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0000 1.7321 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5000 -2.5981 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0000 -1.7321 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 Si 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 -1.7321 0.0000 Si 0 0 0 0 0 0 0 0 0 0 0 0 4.5000 2.5981 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0000 -3.4641 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 25 1 0 0 0 0 2 25 1 0 0 0 0 3 25 1 0 0 0 0 4 26 1 0 0 0 0 5 26 1 0 0 0 0 6 26 1 0 0 0 0 7 9 1 0 0 0 0 7 14 2 0 0 0 0 8 10 2 0 0 0 0 8 14 1 0 0 0 0 9 16 2 0 0 0 0 10 16 1 0 0 0 0 11 15 2 0 0 0 0 11 17 1 0 0 0 0 12 15 1 0 0 0 0 12 18 2 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 19 1 0 0 0 0 16 21 1 0 0 0 0 17 25 1 0 0 0 0 18 26 1 0 0 0 0 19 21 1 0 0 0 0 19 22 2 0 0 0 0 20 23 1 0 0 0 0 20 24 2 0 0 0 0 21 27 1 0 0 0 0 23 28 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB007345
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	385.15
ALogP	4.6488
MLogP	3
XLogP	5.728
HDA	4
HBD	2
Rotatable Bonds	13
TPSA	66.4
RO5 Violation	1