NPASS drugs

Drug Information

Drug ID:	NPD5991
Drug Name:	Doxapram
Molecular Formula:	C24H30N2O2
Canonical SMILES:	CCN1CC(C(C1=O)(c1ccccc1)c1ccccc1)CCN1CCOCC1
Standard InCHI:	InChI=1S/C24H30N2O2/c1-2-26-19-22(13-14-25-15-17-28-18-16-25)24(23(26)27,20-9-5-3-6-10-20)21-11-7-4-8-12-21/h3-12,22H,2,13-19H2,1H3
Standard InCHIKey:	XFDJYSQDBULQSI-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD5991

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	89
0.1-0.2	767
0.2-0.3	2474
0.3-0.4	10777
0.4-0.5	14186
0.5-0.6	2233
0.6-0.7	314
0.7-0.8	50
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	0.7913	NPC473418
Intermediate Similarity	0.7647	NPC158854
Intermediate Similarity	0.7518	NPC161069
Intermediate Similarity	0.7419	NPC473573
Intermediate Similarity	0.7405	NPC239990
Intermediate Similarity	0.7405	NPC152850
Intermediate Similarity	0.7405	NPC89923
Intermediate Similarity	0.7405	NPC71933
Intermediate Similarity	0.7405	NPC105114
Intermediate Similarity	0.7328	NPC136453
Intermediate Similarity	0.7311	NPC167336
Intermediate Similarity	0.7305	NPC138775
Intermediate Similarity	0.725	NPC45033
Intermediate Similarity	0.7239	NPC157311
Intermediate Similarity	0.7218	NPC473322
Intermediate Similarity	0.7185	NPC8761
Intermediate Similarity	0.7185	NPC473962
Intermediate Similarity	0.7185	NPC44805
Intermediate Similarity	0.7154	NPC84281
Intermediate Similarity	0.7154	NPC169485
Intermediate Similarity	0.7154	NPC291027
Intermediate Similarity	0.7154	NPC213126
Intermediate Similarity	0.7154	NPC317474
Intermediate Similarity	0.7153	NPC79465
Intermediate Similarity	0.7153	NPC476102
Intermediate Similarity	0.7153	NPC474787
Intermediate Similarity	0.7153	NPC260045
Intermediate Similarity	0.7153	NPC151706
Intermediate Similarity	0.7153	NPC474855
Intermediate Similarity	0.7153	NPC118099
Intermediate Similarity	0.7153	NPC76785
Intermediate Similarity	0.7153	NPC293377
Intermediate Similarity	0.7153	NPC9687
Intermediate Similarity	0.7153	NPC475598
Intermediate Similarity	0.7153	NPC273907
Intermediate Similarity	0.7153	NPC475318
Intermediate Similarity	0.7153	NPC49577
Intermediate Similarity	0.7153	NPC90194
Intermediate Similarity	0.7153	NPC474811
Intermediate Similarity	0.7121	NPC79698
Intermediate Similarity	0.7109	NPC220698
Intermediate Similarity	0.7077	NPC314192
Intermediate Similarity	0.7049	NPC55529
Intermediate Similarity	0.7043	NPC71140
Intermediate Similarity	0.7043	NPC474974
Intermediate Similarity	0.7037	NPC69496
Intermediate Similarity	0.7007	NPC245836
Intermediate Similarity	0.7007	NPC233910
Intermediate Similarity	0.7	NPC200964
Intermediate Similarity	0.7	NPC302169
Remote Similarity	0.6993	NPC262077
Remote Similarity	0.6985	NPC255447
Remote Similarity	0.6983	NPC256452
Remote Similarity	0.6953	NPC285926
Remote Similarity	0.6953	NPC14672
Remote Similarity	0.6953	NPC315276
Remote Similarity	0.695	NPC263493
Remote Similarity	0.695	NPC269398
Remote Similarity	0.6933	NPC113946
Remote Similarity	0.6929	NPC33742
Remote Similarity	0.6923	NPC5620
Remote Similarity	0.6923	NPC209509
Remote Similarity	0.6912	NPC200589
Remote Similarity	0.6899	NPC470545
Remote Similarity	0.687	NPC27833
Remote Similarity	0.6866	NPC474847
Remote Similarity	0.6861	NPC126458
Remote Similarity	0.6857	NPC471123
Remote Similarity	0.685	NPC276949
Remote Similarity	0.685	NPC35850
Remote Similarity	0.6846	NPC470546
Remote Similarity	0.6842	NPC474082
Remote Similarity	0.6842	NPC175726
Remote Similarity	0.6842	NPC6975
Remote Similarity	0.6822	NPC470544
Remote Similarity	0.6814	NPC305602
Remote Similarity	0.6814	NPC17497
Remote Similarity	0.6809	NPC476133
Remote Similarity	0.6809	NPC98424
Remote Similarity	0.6809	NPC316906
Remote Similarity	0.6809	NPC178662
Remote Similarity	0.6809	NPC470884
Remote Similarity	0.6809	NPC92784
Remote Similarity	0.6797	NPC246904
Remote Similarity	0.6788	NPC179224
Remote Similarity	0.6761	NPC469560
Remote Similarity	0.6755	NPC29285
Remote Similarity	0.6736	NPC476978
Remote Similarity	0.6735	NPC129666
Remote Similarity	0.6723	NPC472258
Remote Similarity	0.6712	NPC145113
Remote Similarity	0.6711	NPC122590
Remote Similarity	0.6711	NPC66936
Remote Similarity	0.6694	NPC473498
Remote Similarity	0.6692	NPC202521
Remote Similarity	0.6692	NPC71684
Remote Similarity	0.6667	NPC322598
Remote Similarity	0.6643	NPC239762
Remote Similarity	0.6643	NPC313663
Remote Similarity	0.6643	NPC163392
Remote Similarity	0.6623	NPC73644
Remote Similarity	0.6621	NPC52748
Remote Similarity	0.662	NPC471265
Remote Similarity	0.662	NPC471264
Remote Similarity	0.6619	NPC130309
Remote Similarity	0.6617	NPC476990
Remote Similarity	0.6604	NPC96901
Remote Similarity	0.6603	NPC472106
Remote Similarity	0.6599	NPC329761
Remote Similarity	0.6599	NPC225648
Remote Similarity	0.6596	NPC248283
Remote Similarity	0.6594	NPC469666
Remote Similarity	0.6594	NPC111428
Remote Similarity	0.6581	NPC472101
Remote Similarity	0.6581	NPC470926
Remote Similarity	0.6581	NPC472120
Remote Similarity	0.6569	NPC65310
Remote Similarity	0.6561	NPC279527
Remote Similarity	0.6561	NPC214960
Remote Similarity	0.6554	NPC240848
Remote Similarity	0.6554	NPC471821
Remote Similarity	0.6554	NPC471820
Remote Similarity	0.6552	NPC22082
Remote Similarity	0.6552	NPC186284
Remote Similarity	0.6544	NPC222466
Remote Similarity	0.6544	NPC285394
Remote Similarity	0.6525	NPC473661
Remote Similarity	0.6522	NPC475427
Remote Similarity	0.6519	NPC252878
Remote Similarity	0.6519	NPC26285
Remote Similarity	0.651	NPC2501
Remote Similarity	0.6507	NPC471516
Remote Similarity	0.6504	NPC329375
Remote Similarity	0.6503	NPC127741
Remote Similarity	0.65	NPC285622
Remote Similarity	0.6496	NPC101719
Remote Similarity	0.6494	NPC104345
Remote Similarity	0.6483	NPC150712
Remote Similarity	0.648	NPC143516
Remote Similarity	0.6475	NPC213969
Remote Similarity	0.6475	NPC165726
Remote Similarity	0.6474	NPC472117
Remote Similarity	0.6474	NPC176983
Remote Similarity	0.6471	NPC46427
Remote Similarity	0.6463	NPC313867
Remote Similarity	0.6463	NPC316008
Remote Similarity	0.6458	NPC281104
Remote Similarity	0.6454	NPC257390
Remote Similarity	0.6443	NPC105717
Remote Similarity	0.6441	NPC125226
Remote Similarity	0.6438	NPC139326
Remote Similarity	0.6438	NPC197682
Remote Similarity	0.6438	NPC470301
Remote Similarity	0.6434	NPC269340
Remote Similarity	0.6429	NPC231986
Remote Similarity	0.6429	NPC471447
Remote Similarity	0.6429	NPC474804
Remote Similarity	0.6429	NPC474973
Remote Similarity	0.6429	NPC130898
Remote Similarity	0.6424	NPC473329
Remote Similarity	0.6424	NPC162104
Remote Similarity	0.6419	NPC314358
Remote Similarity	0.6414	NPC307357
Remote Similarity	0.6414	NPC268841
Remote Similarity	0.6414	NPC46098
Remote Similarity	0.641	NPC472102
Remote Similarity	0.641	NPC309531
Remote Similarity	0.6402	NPC11149
Remote Similarity	0.64	NPC283783
Remote Similarity	0.6398	NPC137627
Remote Similarity	0.6395	NPC314388
Remote Similarity	0.6395	NPC315283
Remote Similarity	0.6387	NPC222029
Remote Similarity	0.6382	NPC473341
Remote Similarity	0.6372	NPC230068
Remote Similarity	0.637	NPC315051
Remote Similarity	0.637	NPC168113
Remote Similarity	0.6369	NPC471051
Remote Similarity	0.6369	NPC471053
Remote Similarity	0.6369	NPC471052
Remote Similarity	0.6357	NPC81092
Remote Similarity	0.6357	NPC103605
Remote Similarity	0.6351	NPC471680
Remote Similarity	0.6349	NPC476198
Remote Similarity	0.6346	NPC276085
Remote Similarity	0.6343	NPC310467
Remote Similarity	0.6338	NPC246913
Remote Similarity	0.6323	NPC297145
Remote Similarity	0.6323	NPC197743
Remote Similarity	0.6319	NPC473360
Remote Similarity	0.6316	NPC239357
Remote Similarity	0.6316	NPC474088
Remote Similarity	0.6316	NPC233702
Remote Similarity	0.6306	NPC225319
Remote Similarity	0.6296	NPC251212
Remote Similarity	0.6296	NPC214626
Remote Similarity	0.6296	NPC139085
Remote Similarity	0.6294	NPC287401
Remote Similarity	0.629	NPC316797
Remote Similarity	0.629	NPC474582

Drug Structure

NPD5991 OpenBabel08211708292D 28 31 0 0 1 0 0 0 0 0999 V2000 -0.9863 1.3575 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1013 0.9634 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6817 -3.4707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3259 -4.4395 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6817 -2.5020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8428 -3.9551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1649 -3.9551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5131 -3.9551 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8428 -2.0176 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0038 -3.4707 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1649 -2.9863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5131 -2.9863 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2858 -2.1519 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2333 -1.9505 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8291 -2.4690 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5822 -3.5917 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4774 -3.1889 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2304 -4.3116 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8390 -0.4844 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0038 -2.5020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3259 -2.5020 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6375 -1.4320 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -0.7199 -0.6482 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.3259 -1.5332 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8816 -2.6704 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6675 -0.4468 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.1780 -4.1102 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 0 0 0 2 26 1 0 0 0 0 3 5 2 0 0 0 0 3 6 1 0 0 0 0 4 7 2 0 0 0 0 4 8 1 0 0 0 0 5 9 1 0 0 0 0 6 10 2 0 0 0 0 7 11 1 0 0 0 0 8 12 2 0 0 0 0 9 20 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 14 1 0 0 0 0 13 22 1 0 0 0 0 14 25 1 0 0 0 0 15 17 1 0 0 0 0 15 25 1 0 0 0 0 16 18 1 0 0 0 0 16 25 1 0 0 0 0 17 28 1 0 0 0 0 18 28 1 0 0 0 0 19 22 1 0 0 0 0 19 26 1 0 0 0 0 20 24 1 0 0 0 0 21 24 1 0 0 0 0 22 24 1 0 0 0 0 23 24 1 0 0 0 0 23 26 1 0 0 0 0 23 27 2 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP001295
DrugBank	DB00561
ChEMBL	CHEMBL1754
IUPHAR/BPS	7169
PharmaGKB	PA164784026
KEGG Drug	D01872
PubChem CID	3156
ChEBI	681848
CAS Number	309-29-5

Drug Properties

Molecular Weight	378.23
ALogP	-1.3173
MLogP	3.66
XLogP	6.246
HDA	4
HBD	0
Rotatable Bonds	7
TPSA	32.78
RO5 Violation	1