NPASS drugs

Drug Information

Drug ID:	NPD4094
Drug Name:	Normethadone
Molecular Formula:	C20H25NO
Canonical SMILES:	CCC(=O)C(c1ccccc1)(c1ccccc1)CCN(C)C
Standard InCHI:	InChI=1S/C20H25NO/c1-4-19(22)20(15-16-21(2)3,17-11-7-5-8-12-17)18-13-9-6-10-14-18/h5-14H,4,15-16H2,1-3H3
Standard InCHIKey:	WCJFBSYALHQBSK-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	DrugBank

Structural Similarity Between NPASS Natural Products and NPD4094

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	80
0.1-0.2	870
0.2-0.3	2596
0.3-0.4	10112
0.4-0.5	13866
0.5-0.6	2783
0.6-0.7	510
0.7-0.8	71
0.8-0.85	2
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	0.8317	NPC167336
Intermediate Similarity	0.8068	NPC9796
Intermediate Similarity	0.7889	NPC272260
Intermediate Similarity	0.783	NPC158854
Intermediate Similarity	0.7692	NPC151405
Intermediate Similarity	0.7692	NPC139901
Intermediate Similarity	0.7629	NPC298115
Intermediate Similarity	0.7619	NPC473418
Intermediate Similarity	0.7614	NPC285679
Intermediate Similarity	0.7609	NPC95868
Intermediate Similarity	0.7604	NPC69057
Intermediate Similarity	0.7582	NPC103488
Intermediate Similarity	0.7576	NPC59677
Intermediate Similarity	0.7547	NPC45033
Intermediate Similarity	0.7527	NPC273033
Intermediate Similarity	0.7527	NPC12936
Intermediate Similarity	0.75	NPC74458
Intermediate Similarity	0.75	NPC71140
Intermediate Similarity	0.7426	NPC256452
Intermediate Similarity	0.7419	NPC71664
Intermediate Similarity	0.7419	NPC477703
Intermediate Similarity	0.7419	NPC17408
Intermediate Similarity	0.7419	NPC285716
Intermediate Similarity	0.7411	NPC473573
Intermediate Similarity	0.74	NPC323420
Intermediate Similarity	0.7379	NPC322598
Intermediate Similarity	0.7368	NPC273758
Intermediate Similarity	0.7353	NPC185208
Intermediate Similarity	0.7353	NPC219573
Intermediate Similarity	0.7327	NPC291070
Intermediate Similarity	0.7327	NPC246757
Intermediate Similarity	0.7282	NPC239185
Intermediate Similarity	0.7273	NPC231591
Intermediate Similarity	0.7263	NPC230068
Intermediate Similarity	0.7234	NPC190567
Intermediate Similarity	0.7216	NPC123476
Intermediate Similarity	0.7212	NPC134882
Intermediate Similarity	0.7204	NPC2785
Intermediate Similarity	0.7204	NPC36342
Intermediate Similarity	0.7204	NPC285470
Intermediate Similarity	0.72	NPC277277
Intermediate Similarity	0.7172	NPC267262
Intermediate Similarity	0.7158	NPC145053
Intermediate Similarity	0.7158	NPC231986
Intermediate Similarity	0.7155	NPC226143
Intermediate Similarity	0.7129	NPC284475
Intermediate Similarity	0.7129	NPC470926
Intermediate Similarity	0.7129	NPC125226
Intermediate Similarity	0.7128	NPC300205
Intermediate Similarity	0.7115	NPC265220
Intermediate Similarity	0.7113	NPC133162
Intermediate Similarity	0.7103	NPC471317
Intermediate Similarity	0.71	NPC418308
Intermediate Similarity	0.71	NPC113307
Intermediate Similarity	0.7097	NPC245966
Intermediate Similarity	0.7097	NPC179726
Intermediate Similarity	0.7097	NPC298023
Intermediate Similarity	0.7075	NPC476993
Intermediate Similarity	0.7075	NPC109514
Intermediate Similarity	0.7071	NPC17497
Intermediate Similarity	0.7071	NPC305602
Intermediate Similarity	0.7059	NPC155232
Intermediate Similarity	0.7059	NPC1682
Intermediate Similarity	0.7059	NPC188844
Intermediate Similarity	0.7059	NPC153885
Intermediate Similarity	0.7053	NPC157055
Intermediate Similarity	0.7053	NPC164086
Intermediate Similarity	0.7048	NPC49994
Intermediate Similarity	0.7048	NPC75724
Intermediate Similarity	0.703	NPC19256
Intermediate Similarity	0.701	NPC474088
Intermediate Similarity	0.7	NPC285394
Intermediate Similarity	0.7	NPC157778
Remote Similarity	0.699	NPC289883
Remote Similarity	0.699	NPC238219
Remote Similarity	0.6989	NPC271642
Remote Similarity	0.6981	NPC476042
Remote Similarity	0.6972	NPC476198
Remote Similarity	0.697	NPC203076
Remote Similarity	0.697	NPC160339
Remote Similarity	0.697	NPC307
Remote Similarity	0.6961	NPC187725
Remote Similarity	0.6961	NPC133461
Remote Similarity	0.6961	NPC141607
Remote Similarity	0.6957	NPC208075
Remote Similarity	0.6944	NPC474866
Remote Similarity	0.6944	NPC475939
Remote Similarity	0.6944	NPC471829
Remote Similarity	0.6944	NPC472691
Remote Similarity	0.6942	NPC79698
Remote Similarity	0.6923	NPC472880
Remote Similarity	0.6923	NPC260233
Remote Similarity	0.6909	NPC473498
Remote Similarity	0.69	NPC43945
Remote Similarity	0.69	NPC60408
Remote Similarity	0.6893	NPC473661
Remote Similarity	0.6885	NPC119326
Remote Similarity	0.6882	NPC98976
Remote Similarity	0.6863	NPC58872
Remote Similarity	0.6863	NPC67585
Remote Similarity	0.6863	NPC173413
Remote Similarity	0.6863	NPC303967
Remote Similarity	0.6863	NPC110420
Remote Similarity	0.6848	NPC271437
Remote Similarity	0.6847	NPC55529
Remote Similarity	0.6842	NPC137847
Remote Similarity	0.6842	NPC76455
Remote Similarity	0.6837	NPC215008
Remote Similarity	0.6837	NPC104070
Remote Similarity	0.6833	NPC291027
Remote Similarity	0.6833	NPC317474
Remote Similarity	0.6833	NPC169485
Remote Similarity	0.6833	NPC84281
Remote Similarity	0.6833	NPC213126
Remote Similarity	0.6825	NPC313663
Remote Similarity	0.6809	NPC139658
Remote Similarity	0.6807	NPC27833
Remote Similarity	0.6792	NPC103048
Remote Similarity	0.6792	NPC226041
Remote Similarity	0.6792	NPC240042
Remote Similarity	0.6789	NPC202613
Remote Similarity	0.678	NPC220698
Remote Similarity	0.6768	NPC169016
Remote Similarity	0.6765	NPC9822
Remote Similarity	0.6765	NPC325709
Remote Similarity	0.6762	NPC206764
Remote Similarity	0.6759	NPC225079
Remote Similarity	0.6759	NPC474582
Remote Similarity	0.6757	NPC472699
Remote Similarity	0.6757	NPC472700
Remote Similarity	0.675	NPC257490
Remote Similarity	0.6746	NPC473962
Remote Similarity	0.6744	NPC316906
Remote Similarity	0.6737	NPC329318
Remote Similarity	0.6724	NPC33742
Remote Similarity	0.6724	NPC246904
Remote Similarity	0.6724	NPC113099
Remote Similarity	0.6723	NPC177684
Remote Similarity	0.6723	NPC291962
Remote Similarity	0.6703	NPC98880
Remote Similarity	0.67	NPC252067
Remote Similarity	0.6698	NPC12695
Remote Similarity	0.6696	NPC472696
Remote Similarity	0.6696	NPC472701
Remote Similarity	0.6696	NPC472683
Remote Similarity	0.6696	NPC472695
Remote Similarity	0.6667	NPC477693
Remote Similarity	0.6667	NPC44830
Remote Similarity	0.6667	NPC161956
Remote Similarity	0.6667	NPC54647
Remote Similarity	0.6667	NPC67043
Remote Similarity	0.6667	NPC197581
Remote Similarity	0.6667	NPC319579
Remote Similarity	0.6667	NPC126458
Remote Similarity	0.6667	NPC471186
Remote Similarity	0.6667	NPC12730
Remote Similarity	0.6667	NPC39600
Remote Similarity	0.6667	NPC258531
Remote Similarity	0.6667	NPC112373
Remote Similarity	0.6667	NPC221825
Remote Similarity	0.6667	NPC34243
Remote Similarity	0.6667	NPC188010
Remote Similarity	0.6667	NPC477704
Remote Similarity	0.6638	NPC35850
Remote Similarity	0.6638	NPC276949
Remote Similarity	0.6637	NPC470252
Remote Similarity	0.6636	NPC329556
Remote Similarity	0.6636	NPC472258
Remote Similarity	0.6635	NPC103346
Remote Similarity	0.6635	NPC86987
Remote Similarity	0.6633	NPC73978
Remote Similarity	0.663	NPC95289
Remote Similarity	0.6607	NPC274089
Remote Similarity	0.6607	NPC191215
Remote Similarity	0.6606	NPC316797
Remote Similarity	0.6606	NPC472879
Remote Similarity	0.6606	NPC128248
Remote Similarity	0.6606	NPC136810
Remote Similarity	0.6606	NPC133809
Remote Similarity	0.6604	NPC329430
Remote Similarity	0.6593	NPC311343
Remote Similarity	0.6591	NPC22786
Remote Similarity	0.6591	NPC29680
Remote Similarity	0.6581	NPC472164
Remote Similarity	0.6579	NPC65855
Remote Similarity	0.6579	NPC292758
Remote Similarity	0.6574	NPC145052
Remote Similarity	0.6569	NPC473031
Remote Similarity	0.6569	NPC322387
Remote Similarity	0.6566	NPC14326
Remote Similarity	0.6556	NPC178527
Remote Similarity	0.6555	NPC476440
Remote Similarity	0.6555	NPC470545
Remote Similarity	0.6549	NPC470007
Remote Similarity	0.6545	NPC239854
Remote Similarity	0.6538	NPC70940
Remote Similarity	0.6538	NPC86670
Remote Similarity	0.6538	NPC274455
Remote Similarity	0.6538	NPC172128
Remote Similarity	0.6538	NPC84288

Drug Structure

NPD4094 OpenBabel08211704332D 22 23 0 0 0 0 0 0 0 0999 V2000 -0.3660 3.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 2.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -2.0981 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8660 -1.2321 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -2.0981 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 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.2321 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 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3660 -0.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3660 1.3660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6340 1.3660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 4 1 0 0 0 0 2 21 1 0 0 0 0 3 21 1 0 0 0 0 4 19 1 0 0 0 0 5 7 2 0 0 0 0 5 8 1 0 0 0 0 6 9 2 0 0 0 0 6 10 1 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 13 1 0 0 0 0 10 14 2 0 0 0 0 11 17 2 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 14 18 1 0 0 0 0 15 16 1 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 20 1 0 0 0 0 18 20 1 0 0 0 0 19 20 1 0 0 0 0 19 22 2 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank	DB11609
ChEMBL	CHEMBL346331
IUPHAR/BPS
PharmaGKB
KEGG Drug	D07384
PubChem CID
ChEBI	135242
CAS Number	467-85-6

Drug Properties

Molecular Weight	295.19
ALogP	-0.0625
MLogP	3.44
XLogP	6.787
HDA	2
HBD	0
Rotatable Bonds	10
TPSA	20.31
RO5 Violation	1