NPASS drugs

Drug Information

Drug ID:	NPD5025
Drug Name:	Apremilast
Molecular Formula:	C22H24N2O7S
Canonical SMILES:	CCOc1cc(ccc1OC)[C@H](N1C(=O)c2c(C1=O)c(ccc2)N=C(O)C)CS(=O)(=O)C
Standard InCHI:	InChI=1S/C22H24N2O7S/c1-5-31-19-11-14(9-10-18(19)30-3)17(12-32(4,28)29)24-21(26)15-7-6-8-16(23-13(2)25)20(15)22(24)27/h6-11,17H,5,12H2,1-4H3,(H,23,25)/t17-/m1/s1
Standard InCHIKey:	IMOZEMNVLZVGJZ-QGZVFWFLSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5025

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	261
0.1-0.2	1517
0.2-0.3	7572
0.3-0.4	5046
0.4-0.5	7192
0.5-0.6	8253
0.6-0.7	1023
0.7-0.8	26
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	0.7981	NPC313327
Intermediate Similarity	0.7583	NPC207971
Intermediate Similarity	0.7547	NPC268077
Intermediate Similarity	0.7442	NPC207873
Intermediate Similarity	0.7442	NPC100573
Intermediate Similarity	0.7429	NPC71124
Intermediate Similarity	0.7395	NPC16249
Intermediate Similarity	0.7383	NPC163829
Intermediate Similarity	0.734	NPC270301
Intermediate Similarity	0.7321	NPC254957
Intermediate Similarity	0.7311	NPC5374
Intermediate Similarity	0.7291	NPC5167
Intermediate Similarity	0.7256	NPC473460
Intermediate Similarity	0.7206	NPC85613
Intermediate Similarity	0.7202	NPC90185
Intermediate Similarity	0.7189	NPC158551
Intermediate Similarity	0.7156	NPC308943
Intermediate Similarity	0.7143	NPC473422
Intermediate Similarity	0.7123	NPC198401
Intermediate Similarity	0.7091	NPC471561
Intermediate Similarity	0.7085	NPC55470
Intermediate Similarity	0.7072	NPC10732
Intermediate Similarity	0.7072	NPC470481
Intermediate Similarity	0.7072	NPC470482
Intermediate Similarity	0.7033	NPC116007
Intermediate Similarity	0.7018	NPC41216
Remote Similarity	0.6959	NPC127178
Remote Similarity	0.6957	NPC222524
Remote Similarity	0.6951	NPC471532
Remote Similarity	0.6943	NPC148124
Remote Similarity	0.6934	NPC45389
Remote Similarity	0.693	NPC477258
Remote Similarity	0.692	NPC159815
Remote Similarity	0.6904	NPC119669
Remote Similarity	0.69	NPC99724
Remote Similarity	0.6887	NPC477259
Remote Similarity	0.6887	NPC169387
Remote Similarity	0.6875	NPC283810
Remote Similarity	0.6872	NPC126556
Remote Similarity	0.6872	NPC83511
Remote Similarity	0.6866	NPC193906
Remote Similarity	0.6866	NPC23080
Remote Similarity	0.6866	NPC17677
Remote Similarity	0.6861	NPC475133
Remote Similarity	0.6856	NPC10653
Remote Similarity	0.6856	NPC318525
Remote Similarity	0.6854	NPC174629
Remote Similarity	0.6847	NPC478075
Remote Similarity	0.6847	NPC222561
Remote Similarity	0.6845	NPC164608
Remote Similarity	0.6833	NPC14339
Remote Similarity	0.6832	NPC135006
Remote Similarity	0.6828	NPC471531
Remote Similarity	0.6825	NPC473007
Remote Similarity	0.6825	NPC102760
Remote Similarity	0.6824	NPC248903
Remote Similarity	0.682	NPC24228
Remote Similarity	0.6816	NPC93653
Remote Similarity	0.681	NPC27887
Remote Similarity	0.6798	NPC153631
Remote Similarity	0.6791	NPC473004
Remote Similarity	0.6791	NPC204970
Remote Similarity	0.6789	NPC100863
Remote Similarity	0.6789	NPC112937
Remote Similarity	0.6784	NPC298449
Remote Similarity	0.6781	NPC26928
Remote Similarity	0.6776	NPC473008
Remote Similarity	0.6757	NPC475147
Remote Similarity	0.6731	NPC303581
Remote Similarity	0.6731	NPC67978
Remote Similarity	0.673	NPC314659
Remote Similarity	0.6729	NPC471650
Remote Similarity	0.6716	NPC299582
Remote Similarity	0.6716	NPC24954
Remote Similarity	0.6715	NPC86469
Remote Similarity	0.6714	NPC32064
Remote Similarity	0.6709	NPC476436
Remote Similarity	0.6698	NPC208890
Remote Similarity	0.6697	NPC108847
Remote Similarity	0.6697	NPC471489
Remote Similarity	0.6696	NPC119722
Remote Similarity	0.6696	NPC116178
Remote Similarity	0.6683	NPC476569
Remote Similarity	0.6682	NPC197335
Remote Similarity	0.6681	NPC470480
Remote Similarity	0.6681	NPC172222
Remote Similarity	0.6667	NPC308267
Remote Similarity	0.6667	NPC321166
Remote Similarity	0.6667	NPC122886
Remote Similarity	0.6667	NPC284842
Remote Similarity	0.6667	NPC217903
Remote Similarity	0.6667	NPC138083
Remote Similarity	0.6653	NPC160113
Remote Similarity	0.6653	NPC253675
Remote Similarity	0.6653	NPC476220
Remote Similarity	0.6652	NPC138830
Remote Similarity	0.6652	NPC295479
Remote Similarity	0.6652	NPC220241
Remote Similarity	0.6651	NPC477186
Remote Similarity	0.6651	NPC99723
Remote Similarity	0.6636	NPC226708
Remote Similarity	0.6636	NPC276120
Remote Similarity	0.6635	NPC287588
Remote Similarity	0.6635	NPC35680
Remote Similarity	0.6625	NPC154922
Remote Similarity	0.6622	NPC198160
Remote Similarity	0.662	NPC283207
Remote Similarity	0.662	NPC64140
Remote Similarity	0.662	NPC174122
Remote Similarity	0.6619	NPC285941
Remote Similarity	0.6615	NPC307682
Remote Similarity	0.6609	NPC38964
Remote Similarity	0.6608	NPC269449
Remote Similarity	0.6601	NPC57512
Remote Similarity	0.6594	NPC236668
Remote Similarity	0.6592	NPC473005
Remote Similarity	0.6587	NPC471604
Remote Similarity	0.6584	NPC470708
Remote Similarity	0.6581	NPC71539
Remote Similarity	0.6581	NPC250960
Remote Similarity	0.6577	NPC67904
Remote Similarity	0.6575	NPC230313
Remote Similarity	0.6575	NPC243626
Remote Similarity	0.6574	NPC162694
Remote Similarity	0.6574	NPC234069
Remote Similarity	0.657	NPC231198
Remote Similarity	0.6569	NPC476429
Remote Similarity	0.6565	NPC146976
Remote Similarity	0.6564	NPC328750
Remote Similarity	0.6564	NPC188163
Remote Similarity	0.6564	NPC213206
Remote Similarity	0.6564	NPC474915
Remote Similarity	0.656	NPC303374
Remote Similarity	0.6558	NPC276674
Remote Similarity	0.6558	NPC33902
Remote Similarity	0.6555	NPC241055
Remote Similarity	0.6552	NPC82056
Remote Similarity	0.6545	NPC266425
Remote Similarity	0.6543	NPC304837
Remote Similarity	0.6543	NPC476258
Remote Similarity	0.6542	NPC179704
Remote Similarity	0.654	NPC157931
Remote Similarity	0.6535	NPC25961
Remote Similarity	0.6535	NPC58661
Remote Similarity	0.653	NPC94499
Remote Similarity	0.6528	NPC21425
Remote Similarity	0.6526	NPC121400
Remote Similarity	0.6526	NPC190461
Remote Similarity	0.6526	NPC28368
Remote Similarity	0.6524	NPC288110
Remote Similarity	0.6517	NPC478189
Remote Similarity	0.6516	NPC161804
Remote Similarity	0.6515	NPC185838
Remote Similarity	0.6513	NPC74216
Remote Similarity	0.6513	NPC314682
Remote Similarity	0.6512	NPC249405
Remote Similarity	0.6507	NPC61731
Remote Similarity	0.6507	NPC186569
Remote Similarity	0.6507	NPC471648
Remote Similarity	0.6504	NPC477161
Remote Similarity	0.65	NPC428
Remote Similarity	0.65	NPC476571
Remote Similarity	0.65	NPC24233
Remote Similarity	0.65	NPC147390
Remote Similarity	0.65	NPC135538
Remote Similarity	0.65	NPC469815
Remote Similarity	0.65	NPC469816
Remote Similarity	0.65	NPC246587
Remote Similarity	0.65	NPC475959
Remote Similarity	0.6498	NPC266994
Remote Similarity	0.6498	NPC320088
Remote Similarity	0.6496	NPC476069
Remote Similarity	0.6492	NPC270515
Remote Similarity	0.6491	NPC85661
Remote Similarity	0.649	NPC306669
Remote Similarity	0.649	NPC113455
Remote Similarity	0.6486	NPC215098
Remote Similarity	0.6486	NPC124302
Remote Similarity	0.6486	NPC70290
Remote Similarity	0.6486	NPC14622
Remote Similarity	0.6486	NPC46744
Remote Similarity	0.6486	NPC73020
Remote Similarity	0.6481	NPC195120
Remote Similarity	0.6481	NPC87560
Remote Similarity	0.6481	NPC87391
Remote Similarity	0.6481	NPC182853
Remote Similarity	0.6479	NPC39822
Remote Similarity	0.6478	NPC127996
Remote Similarity	0.6475	NPC41501
Remote Similarity	0.6473	NPC329631
Remote Similarity	0.6473	NPC254700
Remote Similarity	0.6471	NPC33256
Remote Similarity	0.6468	NPC469539
Remote Similarity	0.6468	NPC469540
Remote Similarity	0.6468	NPC312531
Remote Similarity	0.6468	NPC128476
Remote Similarity	0.6468	NPC329830
Remote Similarity	0.6468	NPC474904
Remote Similarity	0.6468	NPC29531
Remote Similarity	0.646	NPC38961

Drug Structure

NPD5025 OpenBabel08211706322D 33 35 0 0 1 0 0 0 0 0999 V2000 1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3147 2.3956 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 6.0000 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 1.7321 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3147 -1.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 -1.0685 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8147 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 4.0000 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 0.0000 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8147 1.5296 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 -2.8147 -0.2024 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3147 0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 0.0000 C 0 0 2 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 -0.0000 4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3147 0.6636 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8366 0.0055 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6456 1.4067 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8147 1.5296 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.3147 0.6636 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0934 -0.6637 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8535 2.3849 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 -0.8660 5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 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 -7.3147 0.6636 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 13 1 0 0 0 0 3 30 1 0 0 0 0 4 32 1 0 0 0 0 5 31 1 0 0 0 0 6 7 2 0 0 0 0 6 8 1 0 0 0 0 7 15 1 0 0 0 0 8 16 2 0 0 0 0 9 10 2 0 0 0 0 9 14 1 0 0 0 0 10 18 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 32 1 0 0 0 0 13 23 2 3 0 0 0 13 25 1 0 0 0 0 14 17 1 0 0 0 0 15 20 2 0 0 0 0 15 21 1 0 0 0 0 16 20 1 0 0 0 0 16 23 1 0 0 0 0 17 12 1 1 0 0 0 17 24 1 0 0 0 0 18 19 2 0 0 0 0 18 30 1 0 0 0 0 19 31 1 0 0 0 0 20 22 1 0 0 0 0 21 24 1 0 0 0 0 21 26 2 0 0 0 0 22 24 1 0 0 0 0 22 27 2 0 0 0 0 25 33 1 0 0 0 0 28 32 2 0 0 0 0 29 32 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000699
DrugBank	DB05676
ChEMBL	CHEMBL514800
IUPHAR/BPS	7372
PharmaGKB
KEGG Drug	D08860
PubChem CID	11561674
ChEBI	78540
CAS Number	608141-41-9

Drug Properties

Molecular Weight	460.13
ALogP	-1.0449
MLogP	2.78
XLogP	2.647
HDA	7
HBD	1
Rotatable Bonds	13
TPSA	130.95
RO5 Violation	0