NPASS drugs

Drug Information

Drug ID:	NPD4664
Drug Name:
Molecular Formula:	C21H27NO4
Canonical SMILES:	COc1cc(ccc1OC)CC1N(C)CCc2c1cc(OC)c(c2)OC
Standard InCHI:	"InChI=1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3"
Standard InCHIKey:	KGPAYJZAMGEDIQ-UHFFFAOYSA-N
Max Developmental Stage:	Clinical (unspecified phase)
Max Developmental Stage Source:	TTD

Structural Similarity Between NPASS Natural Products and NPD4664

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.
Tanimoto coefficient is calculated based on PubChem 881-bit substructure fingerprints.

Range	Similarity Score Range
0-0.1	141868
0.1-0.2	64044
0.2-0.3	4581
0.3-0.4	653
0.4-0.5	385
0.5-0.6	151
0.6-0.7	26
0.7-0.8	13
0.8-0.85	3
0.85-0.9	1
0.9-0.95	0
0.95-1	5

Similar Natural Products

High Similarity: Tc>=0.85; Intermediate Similarity: 0.7 <= Tc < 0.85; Remote Similarity: 0.5 <= Tc < 0.7

Similarity Level	Similarity Score	Natural Product ID
High Similarity	1.0	NPC213206
High Similarity	1.0	NPC188163
High Similarity	1.0	NPC328750
High Similarity	1.0	NPC602942
High Similarity	1.0	NPC608528
High Similarity	0.875	NPC308771
Intermediate Similarity	0.8444	NPC314682
Intermediate Similarity	0.8444	NPC535693
Intermediate Similarity	0.8444	NPC607670
Intermediate Similarity	0.7547	NPC247639
Intermediate Similarity	0.7547	NPC25084
Intermediate Similarity	0.75	NPC577185
Intermediate Similarity	0.7451	NPC521945
Intermediate Similarity	0.7358	NPC320832
Intermediate Similarity	0.7308	NPC230831
Intermediate Similarity	0.7308	NPC135538
Intermediate Similarity	0.7308	NPC24233
Intermediate Similarity	0.7308	NPC606439
Intermediate Similarity	0.717	NPC135523
Intermediate Similarity	0.7059	NPC185838
Intermediate Similarity	0.7059	NPC601132
Intermediate Similarity	0.7	NPC531720
Remote Similarity	0.6939	NPC274392
Remote Similarity	0.6731	NPC474915
Remote Similarity	0.6667	NPC541687
Remote Similarity	0.661	NPC317272
Remote Similarity	0.661	NPC268503
Remote Similarity	0.661	NPC220089
Remote Similarity	0.6379	NPC296592
Remote Similarity	0.629	NPC256012
Remote Similarity	0.629	NPC600185
Remote Similarity	0.629	NPC610965
Remote Similarity	0.625	NPC504087
Remote Similarity	0.625	NPC596538
Remote Similarity	0.625	NPC603603
Remote Similarity	0.6182	NPC572505
Remote Similarity	0.6167	NPC225718
Remote Similarity	0.6154	NPC71583
Remote Similarity	0.6094	NPC12036
Remote Similarity	0.6094	NPC276890
Remote Similarity	0.6094	NPC502719
Remote Similarity	0.6034	NPC27887
Remote Similarity	0.6034	NPC93989
Remote Similarity	0.6	NPC148253
Remote Similarity	0.6	NPC37179
Remote Similarity	0.6	NPC500436
Remote Similarity	0.6	NPC556148
Remote Similarity	0.6	NPC563874
Remote Similarity	0.5957	NPC566279
Remote Similarity	0.5938	NPC76682
Remote Similarity	0.5938	NPC10908
Remote Similarity	0.5938	NPC63646
Remote Similarity	0.5938	NPC170299
Remote Similarity	0.5938	NPC317145
Remote Similarity	0.5938	NPC198498
Remote Similarity	0.5938	NPC115284
Remote Similarity	0.5938	NPC514529
Remote Similarity	0.5938	NPC574034
Remote Similarity	0.5938	NPC583622
Remote Similarity	0.5938	NPC602190
Remote Similarity	0.5909	NPC240841
Remote Similarity	0.5909	NPC41087
Remote Similarity	0.5909	NPC526734
Remote Similarity	0.5909	NPC536676
Remote Similarity	0.5909	NPC601652
Remote Similarity	0.5893	NPC291647
Remote Similarity	0.5893	NPC147390
Remote Similarity	0.5893	NPC428
Remote Similarity	0.5893	NPC476571
Remote Similarity	0.5873	NPC248714
Remote Similarity	0.5873	NPC528845
Remote Similarity	0.5873	NPC605742
Remote Similarity	0.5846	NPC108591
Remote Similarity	0.58	NPC544090
Remote Similarity	0.5797	NPC475393
Remote Similarity	0.5789	NPC576658
Remote Similarity	0.5763	NPC475959
Remote Similarity	0.5758	NPC562220
Remote Similarity	0.5714	NPC133849
Remote Similarity	0.5672	NPC12424
Remote Similarity	0.5672	NPC129518
Remote Similarity	0.5672	NPC75388
Remote Similarity	0.5672	NPC251580
Remote Similarity	0.5672	NPC328678
Remote Similarity	0.5672	NPC526804
Remote Similarity	0.5652	NPC526263
Remote Similarity	0.5625	NPC190031
Remote Similarity	0.5625	NPC64296
Remote Similarity	0.5625	NPC510170
Remote Similarity	0.5614	NPC45242
Remote Similarity	0.5588	NPC171758
Remote Similarity	0.5588	NPC150006
Remote Similarity	0.5588	NPC590468
Remote Similarity	0.5588	NPC603853
Remote Similarity	0.5522	NPC227060
Remote Similarity	0.5522	NPC68736
Remote Similarity	0.5517	NPC317439
Remote Similarity	0.5517	NPC257084
Remote Similarity	0.5507	NPC290582
Remote Similarity	0.5507	NPC217748
Remote Similarity	0.5507	NPC73492
Remote Similarity	0.5507	NPC182052
Remote Similarity	0.5507	NPC318170
Remote Similarity	0.5507	NPC271013
Remote Similarity	0.5507	NPC51141
Remote Similarity	0.5507	NPC273062
Remote Similarity	0.5507	NPC299990
Remote Similarity	0.5507	NPC207146
Remote Similarity	0.5507	NPC42663
Remote Similarity	0.5507	NPC15414
Remote Similarity	0.5507	NPC480587
Remote Similarity	0.5507	NPC116560
Remote Similarity	0.5507	NPC66535
Remote Similarity	0.5507	NPC215124
Remote Similarity	0.5507	NPC2706
Remote Similarity	0.5507	NPC575236
Remote Similarity	0.5507	NPC602833
Remote Similarity	0.5507	NPC603586
Remote Similarity	0.5507	NPC611435
Remote Similarity	0.5469	NPC82714
Remote Similarity	0.5455	NPC480592
Remote Similarity	0.5439	NPC210437
Remote Similarity	0.5439	NPC16107
Remote Similarity	0.5439	NPC106295
Remote Similarity	0.5439	NPC611909
Remote Similarity	0.5429	NPC322902
Remote Similarity	0.5429	NPC295424
Remote Similarity	0.5429	NPC279228
Remote Similarity	0.5429	NPC306863
Remote Similarity	0.5429	NPC65055
Remote Similarity	0.5405	NPC509002
Remote Similarity	0.5397	NPC520706
Remote Similarity	0.5352	NPC311973
Remote Similarity	0.5352	NPC239824
Remote Similarity	0.5352	NPC112248
Remote Similarity	0.5352	NPC518500
Remote Similarity	0.5352	NPC541031
Remote Similarity	0.5352	NPC548600
Remote Similarity	0.5352	NPC567930
Remote Similarity	0.5352	NPC588373
Remote Similarity	0.5352	NPC600054
Remote Similarity	0.5352	NPC601504
Remote Similarity	0.5345	NPC191376
Remote Similarity	0.5345	NPC51957
Remote Similarity	0.5345	NPC594036
Remote Similarity	0.5342	NPC162524
Remote Similarity	0.5312	NPC252540
Remote Similarity	0.5294	NPC522376
Remote Similarity	0.5278	NPC116465
Remote Similarity	0.5278	NPC23367
Remote Similarity	0.5278	NPC326451
Remote Similarity	0.5278	NPC511697
Remote Similarity	0.5278	NPC573711
Remote Similarity	0.5278	NPC601503
Remote Similarity	0.5254	NPC321505
Remote Similarity	0.5254	NPC179825
Remote Similarity	0.5231	NPC178735
Remote Similarity	0.5231	NPC30779
Remote Similarity	0.5231	NPC579875
Remote Similarity	0.5205	NPC105574
Remote Similarity	0.5205	NPC520021
Remote Similarity	0.5205	NPC523816
Remote Similarity	0.5205	NPC537921
Remote Similarity	0.5185	NPC264642
Remote Similarity	0.5185	NPC128019
Remote Similarity	0.5185	NPC603918
Remote Similarity	0.5172	NPC514568
Remote Similarity	0.5172	NPC609731
Remote Similarity	0.5167	NPC323595
Remote Similarity	0.5156	NPC289930
Remote Similarity	0.5152	NPC226122
Remote Similarity	0.5152	NPC102332
Remote Similarity	0.5152	NPC108373
Remote Similarity	0.5147	NPC571951
Remote Similarity	0.5143	NPC531615
Remote Similarity	0.5139	NPC286119
Remote Similarity	0.5139	NPC509732
Remote Similarity	0.5139	NPC600872
Remote Similarity	0.5106	NPC65196
Remote Similarity	0.5106	NPC150725
Remote Similarity	0.5085	NPC591198
Remote Similarity	0.5077	NPC226708
Remote Similarity	0.5077	NPC516677
Remote Similarity	0.5068	NPC185639
Remote Similarity	0.5068	NPC251735
Remote Similarity	0.5068	NPC254441
Remote Similarity	0.5068	NPC49075
Remote Similarity	0.5068	NPC223690
Remote Similarity	0.5068	NPC9532
Remote Similarity	0.5068	NPC199402
Remote Similarity	0.5068	NPC551063
Remote Similarity	0.5068	NPC565951
Remote Similarity	0.5068	NPC589719
Remote Similarity	0.5068	NPC599951
Remote Similarity	0.5068	NPC607401
Remote Similarity	0.5067	NPC302275
Remote Similarity	0.5067	NPC195538
Remote Similarity	0.5067	NPC541477
Remote Similarity	0.5067	NPC579307

Drug Structure

NPD4664 OpenBabel08211705262D 26 28 0 0 1 0 0 0 0 0999 V2000 -2.5981 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 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 0.8660 1.5000 0.0000 C 0 0 0 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 -4.3301 -3.5000 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 -0.8660 -3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 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 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 -3.4641 -2.0000 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 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 3 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 -5.1962 -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 -1.7321 -3.0000 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 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 22 1 0 0 0 0 2 23 1 0 0 0 0 3 24 1 0 0 0 0 4 25 1 0 0 0 0 5 26 1 0 0 0 0 6 7 2 0 0 0 0 6 14 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 15 1 0 0 0 0 9 22 1 0 0 0 0 10 14 1 0 0 0 0 10 17 1 0 0 0 0 11 14 2 0 0 0 0 11 19 1 0 0 0 0 12 15 2 0 0 0 0 12 20 1 0 0 0 0 13 16 2 0 0 0 0 13 21 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 17 22 1 0 0 0 0 18 19 2 0 0 0 0 18 23 1 0 0 0 0 19 24 1 0 0 0 0 20 21 2 0 0 0 0 20 25 1 0 0 0 0 21 26 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DCL000062
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	15548
ChEBI
CAS Number

Drug Properties

Molecular Weight	357.19
ALogP	0.1875
MLogP	3.22
XLogP	3.069
HDA	1
HBD	0
Rotatable Bonds	11
TPSA	40.16
RO5 Violation	0