NPASS drugs

Drug Information

Drug ID:	NPD4657
Drug Name:	Methadone
Molecular Formula:	C21H27NO
Canonical SMILES:	CCC(=O)C(c1ccccc1)(c1ccccc1)CC(N(C)C)C
Standard InCHI:	InChI=1S/C21H27NO/c1-5-20(23)21(16-17(2)22(3)4,18-12-8-6-9-13-18)19-14-10-7-11-15-19/h6-15,17H,5,16H2,1-4H3
Standard InCHIKey:	USSIQXCVUWKGNF-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD4657

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	81
0.1-0.2	819
0.2-0.3	2792
0.3-0.4	10457
0.4-0.5	13627
0.5-0.6	2576
0.6-0.7	484
0.7-0.8	53
0.8-0.85	0
0.85-0.9	1
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
High Similarity	0.8515	NPC167336
Intermediate Similarity	0.7889	NPC9796
Intermediate Similarity	0.781	NPC473418
Intermediate Similarity	0.7717	NPC272260
Intermediate Similarity	0.7685	NPC158854
Intermediate Similarity	0.7589	NPC473573
Intermediate Similarity	0.7573	NPC322598
Intermediate Similarity	0.7527	NPC151405
Intermediate Similarity	0.7527	NPC139901
Intermediate Similarity	0.7525	NPC246757
Intermediate Similarity	0.7525	NPC291070
Intermediate Similarity	0.7475	NPC298115
Intermediate Similarity	0.7449	NPC69057
Intermediate Similarity	0.7447	NPC95868
Intermediate Similarity	0.7444	NPC285679
Intermediate Similarity	0.7426	NPC59677
Intermediate Similarity	0.7419	NPC103488
Intermediate Similarity	0.7407	NPC45033
Intermediate Similarity	0.7368	NPC12936
Intermediate Similarity	0.7368	NPC231986
Intermediate Similarity	0.7368	NPC273033
Intermediate Similarity	0.7353	NPC71140
Intermediate Similarity	0.7333	NPC74458
Intermediate Similarity	0.7327	NPC470926
Intermediate Similarity	0.7282	NPC256452
Intermediate Similarity	0.7263	NPC285716
Intermediate Similarity	0.7263	NPC477703
Intermediate Similarity	0.7263	NPC17408
Intermediate Similarity	0.7263	NPC71664
Intermediate Similarity	0.7255	NPC323420
Intermediate Similarity	0.7216	NPC273758
Intermediate Similarity	0.7212	NPC185208
Intermediate Similarity	0.7212	NPC219573
Intermediate Similarity	0.7179	NPC226143
Intermediate Similarity	0.7167	NPC285394
Intermediate Similarity	0.7156	NPC476198
Intermediate Similarity	0.7143	NPC239185
Intermediate Similarity	0.7129	NPC231591
Intermediate Similarity	0.7113	NPC230068
Intermediate Similarity	0.7107	NPC79698
Intermediate Similarity	0.7083	NPC190567
Intermediate Similarity	0.7075	NPC134882
Intermediate Similarity	0.7071	NPC123476
Intermediate Similarity	0.7059	NPC277277
Intermediate Similarity	0.7053	NPC36342
Intermediate Similarity	0.7053	NPC2785
Intermediate Similarity	0.7053	NPC285470
Intermediate Similarity	0.703	NPC267262
Intermediate Similarity	0.701	NPC145053
Intermediate Similarity	0.7	NPC213126
Intermediate Similarity	0.7	NPC317474
Intermediate Similarity	0.7	NPC291027
Intermediate Similarity	0.7	NPC84281
Intermediate Similarity	0.7	NPC169485
Remote Similarity	0.699	NPC284475
Remote Similarity	0.699	NPC125226
Remote Similarity	0.6981	NPC265220
Remote Similarity	0.6979	NPC300205
Remote Similarity	0.6975	NPC27833
Remote Similarity	0.6972	NPC471317
Remote Similarity	0.697	NPC133162
Remote Similarity	0.6961	NPC418308
Remote Similarity	0.6961	NPC113307
Remote Similarity	0.6949	NPC220698
Remote Similarity	0.6947	NPC298023
Remote Similarity	0.6947	NPC245966
Remote Similarity	0.6947	NPC179726
Remote Similarity	0.6944	NPC109514
Remote Similarity	0.6944	NPC476993
Remote Similarity	0.6944	NPC474582
Remote Similarity	0.6937	NPC473498
Remote Similarity	0.6931	NPC17497
Remote Similarity	0.6931	NPC305602
Remote Similarity	0.6923	NPC155232
Remote Similarity	0.6923	NPC1682
Remote Similarity	0.6923	NPC153885
Remote Similarity	0.6923	NPC188844
Remote Similarity	0.6916	NPC75724
Remote Similarity	0.6916	NPC49994
Remote Similarity	0.6911	NPC119326
Remote Similarity	0.6907	NPC164086
Remote Similarity	0.6907	NPC157055
Remote Similarity	0.6905	NPC473962
Remote Similarity	0.6897	NPC33742
Remote Similarity	0.6897	NPC246904
Remote Similarity	0.6897	NPC113099
Remote Similarity	0.6893	NPC19256
Remote Similarity	0.6869	NPC474088
Remote Similarity	0.6863	NPC157778
Remote Similarity	0.6857	NPC238219
Remote Similarity	0.6857	NPC289883
Remote Similarity	0.6852	NPC12730
Remote Similarity	0.6852	NPC476042
Remote Similarity	0.6847	NPC67043
Remote Similarity	0.6842	NPC319579
Remote Similarity	0.6842	NPC271642
Remote Similarity	0.6838	NPC188010
Remote Similarity	0.6832	NPC160339
Remote Similarity	0.6832	NPC203076
Remote Similarity	0.6832	NPC307
Remote Similarity	0.6827	NPC133461
Remote Similarity	0.6827	NPC141607
Remote Similarity	0.6827	NPC187725
Remote Similarity	0.6825	NPC126458
Remote Similarity	0.6818	NPC471829
Remote Similarity	0.6818	NPC472691
Remote Similarity	0.6818	NPC474866
Remote Similarity	0.6818	NPC475939
Remote Similarity	0.681	NPC276949
Remote Similarity	0.681	NPC35850
Remote Similarity	0.6809	NPC208075
Remote Similarity	0.6792	NPC472880
Remote Similarity	0.6792	NPC329430
Remote Similarity	0.6792	NPC260233
Remote Similarity	0.6777	NPC257490
Remote Similarity	0.6765	NPC60408
Remote Similarity	0.6765	NPC43945
Remote Similarity	0.6762	NPC473661
Remote Similarity	0.6754	NPC292758
Remote Similarity	0.6754	NPC65855
Remote Similarity	0.675	NPC291962
Remote Similarity	0.675	NPC177684
Remote Similarity	0.6737	NPC98976
Remote Similarity	0.6731	NPC67585
Remote Similarity	0.6731	NPC173413
Remote Similarity	0.6731	NPC58872
Remote Similarity	0.6731	NPC303967
Remote Similarity	0.6731	NPC110420
Remote Similarity	0.6727	NPC239854
Remote Similarity	0.6726	NPC55529
Remote Similarity	0.6723	NPC476440
Remote Similarity	0.6723	NPC470545
Remote Similarity	0.6719	NPC313663
Remote Similarity	0.6702	NPC271437
Remote Similarity	0.6701	NPC76455
Remote Similarity	0.6701	NPC137847
Remote Similarity	0.67	NPC104070
Remote Similarity	0.67	NPC215008
Remote Similarity	0.67	NPC119677
Remote Similarity	0.6696	NPC474695
Remote Similarity	0.6694	NPC258531
Remote Similarity	0.6694	NPC112373
Remote Similarity	0.6694	NPC161956
Remote Similarity	0.6667	NPC10781
Remote Similarity	0.6667	NPC139658
Remote Similarity	0.6667	NPC116057
Remote Similarity	0.6667	NPC103048
Remote Similarity	0.6667	NPC240042
Remote Similarity	0.6667	NPC202613
Remote Similarity	0.6667	NPC293628
Remote Similarity	0.6667	NPC324569
Remote Similarity	0.6667	NPC470546
Remote Similarity	0.6667	NPC226041
Remote Similarity	0.6667	NPC472258
Remote Similarity	0.6667	NPC122493
Remote Similarity	0.6641	NPC316906
Remote Similarity	0.664	NPC136453
Remote Similarity	0.6639	NPC470544
Remote Similarity	0.6637	NPC472700
Remote Similarity	0.6637	NPC472699
Remote Similarity	0.6636	NPC206764
Remote Similarity	0.6636	NPC225079
Remote Similarity	0.6635	NPC325709
Remote Similarity	0.6635	NPC9822
Remote Similarity	0.6634	NPC169016
Remote Similarity	0.6632	NPC112609
Remote Similarity	0.6632	NPC113000
Remote Similarity	0.6632	NPC122327
Remote Similarity	0.6615	NPC118099
Remote Similarity	0.6615	NPC474787
Remote Similarity	0.6615	NPC151706
Remote Similarity	0.6615	NPC476102
Remote Similarity	0.6615	NPC474811
Remote Similarity	0.6615	NPC79465
Remote Similarity	0.6615	NPC260045
Remote Similarity	0.6615	NPC49577
Remote Similarity	0.6615	NPC90194
Remote Similarity	0.6615	NPC475318
Remote Similarity	0.6615	NPC474855
Remote Similarity	0.6615	NPC9687
Remote Similarity	0.6615	NPC273907
Remote Similarity	0.6615	NPC475598
Remote Similarity	0.6615	NPC293377
Remote Similarity	0.6615	NPC76785
Remote Similarity	0.6614	NPC69496
Remote Similarity	0.661	NPC472164
Remote Similarity	0.6598	NPC290638
Remote Similarity	0.6598	NPC329318
Remote Similarity	0.6591	NPC153007
Remote Similarity	0.6587	NPC89923
Remote Similarity	0.6587	NPC152850
Remote Similarity	0.6587	NPC71933
Remote Similarity	0.6587	NPC239990
Remote Similarity	0.6587	NPC305717
Remote Similarity	0.6587	NPC105114
Remote Similarity	0.6579	NPC472701
Remote Similarity	0.6579	NPC472683
Remote Similarity	0.6579	NPC472695
Remote Similarity	0.6579	NPC472696
Remote Similarity	0.6574	NPC12695

Drug Structure

NPD4657 OpenBabel08211705262D 23 24 0 0 1 0 0 0 0 0999 V2000 -0.3514 -2.9742 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 -3.3600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 -4.3200 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3255 -2.8800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 -2.1428 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2714 2.0142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7514 1.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3114 2.0142 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 1.4400 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6628 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2714 0.3514 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 1.1828 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8314 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 -0.9600 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6628 -2.8800 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -1.3114 0.3514 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 -0.3514 -1.3114 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8314 -0.4800 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 -3.3600 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.6086 -1.3114 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 5 1 0 0 0 0 2 17 1 0 0 0 0 3 22 1 0 0 0 0 4 22 1 0 0 0 0 5 20 1 0 0 0 0 6 8 2 0 0 0 0 6 9 1 0 0 0 0 7 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 1 0 0 0 0 9 13 2 0 0 0 0 10 14 1 0 0 0 0 11 15 2 0 0 0 0 12 18 2 0 0 0 0 13 18 1 0 0 0 0 14 19 2 0 0 0 0 15 19 1 0 0 0 0 16 17 1 0 0 0 0 16 21 1 0 0 0 0 17 22 1 0 0 0 0 18 21 1 0 0 0 0 19 21 1 0 0 0 0 20 21 1 0 0 0 0 20 23 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000267
DrugBank	DB00333
ChEMBL	CHEMBL651
IUPHAR/BPS	5458
PharmaGKB	PA450401
KEGG Drug
PubChem CID	4095
ChEBI	6807
CAS Number	76-99-3

Drug Properties

Molecular Weight	309.21
ALogP	-0.2664
MLogP	3.55
XLogP	7.247
HDA	2
HBD	0
Rotatable Bonds	11
TPSA	20.31
RO5 Violation	1