NPASS drugs

Drug Information

Drug ID:	NPD6354
Drug Name:	etarotene
Molecular Formula:	C25H32O2S
Canonical SMILES:	CCS(=O)(=O)c1ccc(cc1)/C=C(/c1ccc2c(c1)C(C)(C)CCC2(C)C)C
Standard InCHI:	InChI=1S/C25H32O2S/c1-7-28(26,27)21-11-8-19(9-12-21)16-18(2)20-10-13-22-23(17-20)25(5,6)15-14-24(22,3)4/h8-13,16-17H,7,14-15H2,1-6H3/b18-16+
Standard InCHIKey:	UDAZCXVIYSIEFX-FBMGVBCBSA-N
Max Developmental Stage:	Discontinued
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD6354

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	583
0.1-0.2	1737
0.2-0.3	7097
0.3-0.4	15786
0.4-0.5	5001
0.5-0.6	591
0.6-0.7	88
0.7-0.8	7
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	0.7474	NPC159661
Intermediate Similarity	0.7447	NPC3190
Intermediate Similarity	0.7447	NPC249018
Intermediate Similarity	0.7053	NPC307195
Intermediate Similarity	0.7041	NPC315216
Intermediate Similarity	0.7021	NPC54269
Intermediate Similarity	0.7021	NPC212463
Remote Similarity	0.6947	NPC96835
Remote Similarity	0.6947	NPC258492
Remote Similarity	0.6915	NPC158028
Remote Similarity	0.6915	NPC87099
Remote Similarity	0.6915	NPC135433
Remote Similarity	0.6915	NPC39799
Remote Similarity	0.6915	NPC280135
Remote Similarity	0.6915	NPC193578
Remote Similarity	0.6915	NPC1008
Remote Similarity	0.6915	NPC226999
Remote Similarity	0.6882	NPC5324
Remote Similarity	0.6837	NPC66270
Remote Similarity	0.6837	NPC245896
Remote Similarity	0.6809	NPC72670
Remote Similarity	0.6762	NPC298115
Remote Similarity	0.6731	NPC60408
Remote Similarity	0.6702	NPC213570
Remote Similarity	0.6702	NPC246822
Remote Similarity	0.6702	NPC139416
Remote Similarity	0.67	NPC50063
Remote Similarity	0.6667	NPC6107
Remote Similarity	0.6636	NPC220596
Remote Similarity	0.6636	NPC125226
Remote Similarity	0.6635	NPC148231
Remote Similarity	0.6559	NPC113837
Remote Similarity	0.6559	NPC289915
Remote Similarity	0.6559	NPC178527
Remote Similarity	0.65	NPC255345
Remote Similarity	0.6489	NPC267443
Remote Similarity	0.6471	NPC242628
Remote Similarity	0.6465	NPC302129
Remote Similarity	0.6458	NPC251490
Remote Similarity	0.6421	NPC181786
Remote Similarity	0.6396	NPC219573
Remote Similarity	0.6396	NPC185208
Remote Similarity	0.6383	NPC36440
Remote Similarity	0.6372	NPC221825
Remote Similarity	0.6344	NPC22627
Remote Similarity	0.6339	NPC324602
Remote Similarity	0.6339	NPC239185
Remote Similarity	0.6327	NPC1901
Remote Similarity	0.6316	NPC128248
Remote Similarity	0.6316	NPC136810
Remote Similarity	0.6316	NPC133809
Remote Similarity	0.6316	NPC476993
Remote Similarity	0.6286	NPC267704
Remote Similarity	0.6283	NPC134882
Remote Similarity	0.6277	NPC32312
Remote Similarity	0.6277	NPC291066
Remote Similarity	0.6277	NPC198023
Remote Similarity	0.6277	NPC155172
Remote Similarity	0.6239	NPC26224
Remote Similarity	0.6237	NPC22786
Remote Similarity	0.6237	NPC29680
Remote Similarity	0.6237	NPC71009
Remote Similarity	0.6216	NPC289883
Remote Similarity	0.6207	NPC19856
Remote Similarity	0.6195	NPC226041
Remote Similarity	0.6195	NPC265220
Remote Similarity	0.619	NPC125549
Remote Similarity	0.6174	NPC109514
Remote Similarity	0.617	NPC45756
Remote Similarity	0.617	NPC88566
Remote Similarity	0.617	NPC113670
Remote Similarity	0.6154	NPC56168
Remote Similarity	0.6146	NPC52330
Remote Similarity	0.614	NPC75724
Remote Similarity	0.614	NPC49994
Remote Similarity	0.6139	NPC110264
Remote Similarity	0.6134	NPC21929
Remote Similarity	0.6129	NPC246588
Remote Similarity	0.6129	NPC310758
Remote Similarity	0.6129	NPC150196
Remote Similarity	0.6129	NPC210849
Remote Similarity	0.6129	NPC54368
Remote Similarity	0.6129	NPC248705
Remote Similarity	0.6129	NPC238023
Remote Similarity	0.6126	NPC323420
Remote Similarity	0.6126	NPC59677
Remote Similarity	0.6122	NPC263385
Remote Similarity	0.6102	NPC471186
Remote Similarity	0.605	NPC142326
Remote Similarity	0.605	NPC94751
Remote Similarity	0.6034	NPC225079
Remote Similarity	0.6022	NPC147062
Remote Similarity	0.6018	NPC260233
Remote Similarity	0.6	NPC472979
Remote Similarity	0.6	NPC27252
Remote Similarity	0.5982	NPC155232
Remote Similarity	0.5982	NPC475057
Remote Similarity	0.5982	NPC153885
Remote Similarity	0.5966	NPC243601
Remote Similarity	0.5965	NPC317400
Remote Similarity	0.5957	NPC45255
Remote Similarity	0.5957	NPC135924
Remote Similarity	0.595	NPC149455
Remote Similarity	0.595	NPC64642
Remote Similarity	0.595	NPC475006
Remote Similarity	0.595	NPC472982
Remote Similarity	0.595	NPC470252
Remote Similarity	0.5946	NPC19256
Remote Similarity	0.5946	NPC277277
Remote Similarity	0.5932	NPC472691
Remote Similarity	0.5932	NPC474866
Remote Similarity	0.5932	NPC471829
Remote Similarity	0.5932	NPC475939
Remote Similarity	0.5929	NPC238219
Remote Similarity	0.5914	NPC36357
Remote Similarity	0.5914	NPC8235
Remote Similarity	0.5914	NPC64270
Remote Similarity	0.5914	NPC114327
Remote Similarity	0.5909	NPC267262
Remote Similarity	0.5897	NPC472879
Remote Similarity	0.5895	NPC66517
Remote Similarity	0.5893	NPC475059
Remote Similarity	0.5893	NPC475023
Remote Similarity	0.5893	NPC284475
Remote Similarity	0.5893	NPC133461
Remote Similarity	0.5877	NPC472880
Remote Similarity	0.5868	NPC472980
Remote Similarity	0.5865	NPC67863
Remote Similarity	0.5859	NPC473206
Remote Similarity	0.5854	NPC95126
Remote Similarity	0.5854	NPC475002
Remote Similarity	0.5854	NPC265513
Remote Similarity	0.5841	NPC188844
Remote Similarity	0.5841	NPC1682
Remote Similarity	0.5833	NPC133162
Remote Similarity	0.5833	NPC95429
Remote Similarity	0.5833	NPC21211
Remote Similarity	0.5833	NPC313850
Remote Similarity	0.5818	NPC69057
Remote Similarity	0.581	NPC272260
Remote Similarity	0.5806	NPC120441
Remote Similarity	0.5806	NPC212114
Remote Similarity	0.5806	NPC65873
Remote Similarity	0.5806	NPC471188
Remote Similarity	0.5806	NPC300345
Remote Similarity	0.5806	NPC280789
Remote Similarity	0.5806	NPC471189
Remote Similarity	0.5804	NPC173413
Remote Similarity	0.5794	NPC230068
Remote Similarity	0.5785	NPC472699
Remote Similarity	0.5785	NPC472700
Remote Similarity	0.5776	NPC251579
Remote Similarity	0.5776	NPC133135
Remote Similarity	0.5769	NPC9796
Remote Similarity	0.5763	NPC474582
Remote Similarity	0.576	NPC93287
Remote Similarity	0.5752	NPC103346
Remote Similarity	0.5738	NPC472701
Remote Similarity	0.5738	NPC472695
Remote Similarity	0.5738	NPC472683
Remote Similarity	0.5738	NPC472696
Remote Similarity	0.5729	NPC200745
Remote Similarity	0.5727	NPC160339
Remote Similarity	0.5727	NPC307
Remote Similarity	0.5726	NPC120393
Remote Similarity	0.5714	NPC471721
Remote Similarity	0.5714	NPC418308
Remote Similarity	0.5714	NPC239854
Remote Similarity	0.5714	NPC103488
Remote Similarity	0.5703	NPC472862
Remote Similarity	0.5703	NPC105141
Remote Similarity	0.5703	NPC242764
Remote Similarity	0.5702	NPC128645
Remote Similarity	0.5699	NPC269586
Remote Similarity	0.5699	NPC198841
Remote Similarity	0.5669	NPC195922
Remote Similarity	0.5669	NPC221275
Remote Similarity	0.5669	NPC215419
Remote Similarity	0.5659	NPC476440
Remote Similarity	0.5659	NPC45794
Remote Similarity	0.5648	NPC73637
Remote Similarity	0.5648	NPC121478
Remote Similarity	0.5645	NPC273837
Remote Similarity	0.5641	NPC469891
Remote Similarity	0.5641	NPC469892
Remote Similarity	0.5641	NPC469890
Remote Similarity	0.5636	NPC475710
Remote Similarity	0.5635	NPC46940
Remote Similarity	0.5635	NPC470253
Remote Similarity	0.563	NPC289117
Remote Similarity	0.563	NPC245927
Remote Similarity	0.563	NPC264728
Remote Similarity	0.5625	NPC153308
Remote Similarity	0.5625	NPC157778
Remote Similarity	0.5625	NPC469719
Remote Similarity	0.562	NPC472221
Remote Similarity	0.562	NPC472222
Remote Similarity	0.5619	NPC179726
Remote Similarity	0.5615	NPC254233
Remote Similarity	0.5614	NPC470926

Drug Structure

NPD6354 OpenBabel08211709092D 28 30 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 -4.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.3660 0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5000 -0.1340 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6340 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5000 3.5981 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 -2.5000 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 -6.0000 -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 -1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5000 2.5981 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 -6.0000 1.7321 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 -3.0000 -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 -1.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0000 1.7321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.5000 0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5000 2.5981 0.0000 C 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 -0.0000 0.0000 S 0 0 0 0 0 0 0 0 0 0 0 0 1 7 1 0 0 0 0 2 18 1 0 0 0 0 3 24 1 0 0 0 0 4 24 1 0 0 0 0 5 25 1 0 0 0 0 6 25 1 0 0 0 0 7 28 1 0 0 0 0 8 11 1 0 0 0 0 8 19 2 0 0 0 0 9 12 2 0 0 0 0 9 19 1 0 0 0 0 10 13 2 0 0 0 0 10 20 1 0 0 0 0 11 21 2 0 0 0 0 12 21 1 0 0 0 0 13 22 1 0 0 0 0 14 15 1 0 0 0 0 14 24 1 0 0 0 0 15 25 1 0 0 0 0 16 18 2 0 0 0 0 16 19 1 0 0 0 0 17 20 2 0 0 0 0 17 23 1 0 0 0 0 18 20 1 0 0 0 0 21 28 1 0 0 0 0 22 23 2 0 0 0 0 22 24 1 0 0 0 0 23 25 1 0 0 0 0 26 28 2 0 0 0 0 27 28 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DIB013687
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID
ChEBI
CAS Number

Drug Properties

Molecular Weight	396.21
ALogP	2.7949
MLogP	3.88
XLogP	10.829
HDA	2
HBD	0
Rotatable Bonds	10
TPSA	42.52
RO5 Violation	1