NPASS drugs

Drug Information

Drug ID:	NPD3554
Drug Name:	Labetalol
Molecular Formula:	C19H24N2O3
Canonical SMILES:	CC(CCc1ccccc1)NCC(c1ccc(c(c1)C(=N)O)O)O
Standard InCHI:	InChI=1S/C19H24N2O3/c1-13(7-8-14-5-3-2-4-6-14)21-12-18(23)15-9-10-17(22)16(11-15)19(20)24/h2-6,9-11,13,18,21-23H,7-8,12H2,1H3,(H2,20,24)
Standard InCHIKey:	SGUAFYQXFOLMHL-UHFFFAOYSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD3554

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	113
0.1-0.2	781
0.2-0.3	3232
0.3-0.4	9050
0.4-0.5	5059
0.5-0.6	9865
0.6-0.7	2614
0.7-0.8	173
0.8-0.85	3
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	0.8359	NPC213
Intermediate Similarity	0.8359	NPC10286
Intermediate Similarity	0.8346	NPC307020
Intermediate Similarity	0.7986	NPC168861
Intermediate Similarity	0.7972	NPC214988
Intermediate Similarity	0.7899	NPC322366
Intermediate Similarity	0.7891	NPC145638
Intermediate Similarity	0.7891	NPC290566
Intermediate Similarity	0.7836	NPC283760
Intermediate Similarity	0.7826	NPC29477
Intermediate Similarity	0.7744	NPC82963
Intermediate Similarity	0.7714	NPC477839
Intermediate Similarity	0.7692	NPC267237
Intermediate Similarity	0.7687	NPC137096
Intermediate Similarity	0.7687	NPC311737
Intermediate Similarity	0.7687	NPC38458
Intermediate Similarity	0.7674	NPC153690
Intermediate Similarity	0.7643	NPC236347
Intermediate Similarity	0.7643	NPC323775
Intermediate Similarity	0.7626	NPC95733
Intermediate Similarity	0.7626	NPC62101
Intermediate Similarity	0.7622	NPC208757
Intermediate Similarity	0.7594	NPC118202
Intermediate Similarity	0.7586	NPC64205
Intermediate Similarity	0.7568	NPC326241
Intermediate Similarity	0.7552	NPC326966
Intermediate Similarity	0.7538	NPC24101
Intermediate Similarity	0.7538	NPC96224
Intermediate Similarity	0.7537	NPC317254
Intermediate Similarity	0.7535	NPC325651
Intermediate Similarity	0.75	NPC226778
Intermediate Similarity	0.75	NPC304761
Intermediate Similarity	0.75	NPC247018
Intermediate Similarity	0.75	NPC307123
Intermediate Similarity	0.75	NPC150254
Intermediate Similarity	0.75	NPC147000
Intermediate Similarity	0.75	NPC97870
Intermediate Similarity	0.7445	NPC43275
Intermediate Similarity	0.7442	NPC211551
Intermediate Similarity	0.7432	NPC197921
Intermediate Similarity	0.7429	NPC211218
Intermediate Similarity	0.7424	NPC475018
Intermediate Similarity	0.7424	NPC474149
Intermediate Similarity	0.7413	NPC271808
Intermediate Similarity	0.741	NPC474862
Intermediate Similarity	0.7405	NPC63698
Intermediate Similarity	0.7405	NPC61885
Intermediate Similarity	0.7385	NPC231705
Intermediate Similarity	0.7383	NPC91953
Intermediate Similarity	0.7383	NPC469360
Intermediate Similarity	0.7358	NPC22014
Intermediate Similarity	0.7348	NPC258056
Intermediate Similarity	0.7346	NPC195392
Intermediate Similarity	0.7344	NPC327226
Intermediate Similarity	0.7333	NPC473137
Intermediate Similarity	0.7333	NPC12656
Intermediate Similarity	0.7328	NPC142297
Intermediate Similarity	0.7297	NPC473055
Intermediate Similarity	0.7297	NPC473052
Intermediate Similarity	0.7273	NPC476353
Intermediate Similarity	0.7273	NPC262365
Intermediate Similarity	0.7267	NPC212850
Intermediate Similarity	0.7267	NPC83289
Intermediate Similarity	0.7267	NPC477837
Intermediate Similarity	0.7267	NPC189724
Intermediate Similarity	0.7267	NPC477838
Intermediate Similarity	0.7266	NPC169207
Intermediate Similarity	0.7266	NPC213730
Intermediate Similarity	0.7266	NPC223451
Intermediate Similarity	0.7266	NPC115627
Intermediate Similarity	0.7266	NPC118522
Intermediate Similarity	0.726	NPC149379
Intermediate Similarity	0.7248	NPC322526
Intermediate Similarity	0.7246	NPC5932
Intermediate Similarity	0.7244	NPC476742
Intermediate Similarity	0.7239	NPC4493
Intermediate Similarity	0.7239	NPC165770
Intermediate Similarity	0.7239	NPC225679
Intermediate Similarity	0.7239	NPC476632
Intermediate Similarity	0.7218	NPC65855
Intermediate Similarity	0.7218	NPC292758
Intermediate Similarity	0.7214	NPC284078
Intermediate Similarity	0.7209	NPC7686
Intermediate Similarity	0.7209	NPC40258
Intermediate Similarity	0.7209	NPC91461
Intermediate Similarity	0.7208	NPC245974
Intermediate Similarity	0.7203	NPC141739
Intermediate Similarity	0.7203	NPC136112
Intermediate Similarity	0.7203	NPC320242
Intermediate Similarity	0.72	NPC476989
Intermediate Similarity	0.7197	NPC476741
Intermediate Similarity	0.7188	NPC78119
Intermediate Similarity	0.7188	NPC51333
Intermediate Similarity	0.7188	NPC132078
Intermediate Similarity	0.7188	NPC128723
Intermediate Similarity	0.7188	NPC125732
Intermediate Similarity	0.7188	NPC216468
Intermediate Similarity	0.7188	NPC79328
Intermediate Similarity	0.7185	NPC43525
Intermediate Similarity	0.7178	NPC209377
Intermediate Similarity	0.7176	NPC233396
Intermediate Similarity	0.7176	NPC474839
Intermediate Similarity	0.7176	NPC154899
Intermediate Similarity	0.717	NPC244336
Intermediate Similarity	0.7164	NPC44732
Intermediate Similarity	0.7161	NPC473491
Intermediate Similarity	0.7161	NPC476743
Intermediate Similarity	0.7154	NPC178902
Intermediate Similarity	0.7134	NPC56887
Intermediate Similarity	0.7134	NPC223077
Intermediate Similarity	0.7134	NPC193853
Intermediate Similarity	0.7133	NPC14600
Intermediate Similarity	0.7133	NPC41473
Intermediate Similarity	0.7133	NPC204848
Intermediate Similarity	0.7133	NPC318591
Intermediate Similarity	0.7133	NPC160607
Intermediate Similarity	0.7133	NPC231163
Intermediate Similarity	0.7133	NPC312770
Intermediate Similarity	0.7132	NPC117846
Intermediate Similarity	0.7132	NPC289381
Intermediate Similarity	0.7132	NPC155847
Intermediate Similarity	0.7132	NPC214200
Intermediate Similarity	0.7132	NPC228400
Intermediate Similarity	0.7122	NPC85276
Intermediate Similarity	0.7121	NPC135464
Intermediate Similarity	0.7121	NPC92623
Intermediate Similarity	0.7115	NPC476744
Intermediate Similarity	0.7111	NPC308689
Intermediate Similarity	0.7109	NPC290515
Intermediate Similarity	0.7109	NPC303611
Intermediate Similarity	0.7109	NPC226096
Intermediate Similarity	0.7109	NPC315921
Intermediate Similarity	0.7109	NPC164514
Intermediate Similarity	0.7109	NPC108606
Intermediate Similarity	0.7105	NPC204546
Intermediate Similarity	0.7099	NPC63931
Intermediate Similarity	0.7099	NPC119860
Intermediate Similarity	0.7089	NPC476268
Intermediate Similarity	0.7086	NPC170170
Intermediate Similarity	0.7086	NPC211468
Intermediate Similarity	0.7086	NPC219233
Intermediate Similarity	0.7083	NPC318965
Intermediate Similarity	0.708	NPC107240
Intermediate Similarity	0.7078	NPC247298
Intermediate Similarity	0.7075	NPC45191
Intermediate Similarity	0.7073	NPC280022
Intermediate Similarity	0.7071	NPC268572
Intermediate Similarity	0.7059	NPC228425
Intermediate Similarity	0.7059	NPC266741
Intermediate Similarity	0.705	NPC283468
Intermediate Similarity	0.7045	NPC138942
Intermediate Similarity	0.7045	NPC219286
Intermediate Similarity	0.7045	NPC99557
Intermediate Similarity	0.7042	NPC27581
Intermediate Similarity	0.7039	NPC323123
Intermediate Similarity	0.7032	NPC313414
Intermediate Similarity	0.703	NPC46009
Intermediate Similarity	0.7027	NPC328070
Intermediate Similarity	0.7027	NPC471953
Intermediate Similarity	0.7027	NPC244866
Intermediate Similarity	0.7023	NPC168829
Intermediate Similarity	0.7021	NPC263835
Intermediate Similarity	0.702	NPC471201
Intermediate Similarity	0.702	NPC48202
Intermediate Similarity	0.7019	NPC37205
Intermediate Similarity	0.7019	NPC29647
Intermediate Similarity	0.7019	NPC469243
Intermediate Similarity	0.7019	NPC160931
Intermediate Similarity	0.7013	NPC81026
Intermediate Similarity	0.7007	NPC126859
Intermediate Similarity	0.7007	NPC89769
Intermediate Similarity	0.7007	NPC259665
Intermediate Similarity	0.7	NPC122009
Intermediate Similarity	0.7	NPC131118
Intermediate Similarity	0.7	NPC233926
Intermediate Similarity	0.7	NPC237227
Remote Similarity	0.6986	NPC17374
Remote Similarity	0.6986	NPC8305
Remote Similarity	0.6986	NPC268763
Remote Similarity	0.6986	NPC66177
Remote Similarity	0.6986	NPC296712
Remote Similarity	0.6985	NPC227553
Remote Similarity	0.6981	NPC244509
Remote Similarity	0.6978	NPC281686
Remote Similarity	0.6978	NPC106551
Remote Similarity	0.6978	NPC188867
Remote Similarity	0.6977	NPC107619
Remote Similarity	0.6975	NPC206736
Remote Similarity	0.6975	NPC195766
Remote Similarity	0.6974	NPC299583
Remote Similarity	0.6974	NPC150712
Remote Similarity	0.6972	NPC86966
Remote Similarity	0.697	NPC288411
Remote Similarity	0.6968	NPC119569
Remote Similarity	0.6968	NPC16188
Remote Similarity	0.6959	NPC257390
Remote Similarity	0.6959	NPC473724
Remote Similarity	0.6953	NPC313650
Remote Similarity	0.6953	NPC26244
Remote Similarity	0.695	NPC151197

Drug Structure

NPD3554 OpenBabel08211703112D 29 30 0 0 1 0 0 0 0 0999 V2000 1.7321 6.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 3.0000 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 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 3.5000 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 -0.8660 0.5000 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 0.8660 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 5.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 2.0000 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 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 3.0000 0.0000 C 0 0 3 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 2.5981 0.5000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 4.5000 0.0000 N 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 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 -0.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 5.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -1.5000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 13 1 0 0 0 0 2 3 2 0 0 0 0 2 4 1 0 0 0 0 3 5 1 0 0 0 0 4 6 2 0 0 0 0 5 14 2 0 0 0 0 6 14 1 0 0 0 0 7 8 1 0 0 0 0 7 13 1 0 0 0 0 8 14 1 0 0 0 0 9 10 2 0 0 0 0 9 15 1 0 0 0 0 10 17 1 0 0 0 0 11 15 2 0 0 0 0 11 16 1 0 0 0 0 12 18 1 0 0 0 0 12 21 1 0 0 0 0 13 21 1 0 0 0 0 15 18 1 0 0 0 0 16 17 2 0 0 0 0 16 19 1 0 0 0 0 17 22 1 0 0 0 0 18 23 1 0 0 0 0 19 20 2 0 0 0 0 19 24 1 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 23 28 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000038
DrugBank	DB00598
ChEMBL	CHEMBL429
IUPHAR/BPS	7207
PharmaGKB	PA164743150
KEGG Drug
PubChem CID	3869
ChEBI	6343
CAS Number	36894-69-6

Drug Properties

Molecular Weight	328.18
ALogP	-1.6861
MLogP	3
XLogP	5.253
HDA	4
HBD	5
Rotatable Bonds	12
TPSA	96.57
RO5 Violation	1