NPASS drugs

Drug Information

Drug ID:	NPD4601
Drug Name:	Yohimbine
Molecular Formula:	C21H26N2O3
Canonical SMILES:	COC(=O)[C@H]1[C@@H](O)CC[C@@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1
Standard InCHI:	"InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/t12-,15-,17-,18-,19+/m0/s1"
Standard InCHIKey:	BLGXFZZNTVWLAY-SCYLSFHTSA-N
Max Developmental Stage:	Phase 4
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD4601

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	77231
0.1-0.2	130549
0.2-0.3	3118
0.3-0.4	539
0.4-0.5	177
0.5-0.6	61
0.6-0.7	32
0.7-0.8	16
0.8-0.85	5
0.85-0.9	0
0.9-0.95	0
0.95-1	12

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	NPC284075
High Similarity	1.0	NPC313985
High Similarity	1.0	NPC249150
High Similarity	1.0	NPC326180
High Similarity	1.0	NPC33619
High Similarity	1.0	NPC540096
High Similarity	1.0	NPC572911
High Similarity	1.0	NPC581804
High Similarity	1.0	NPC604228
High Similarity	1.0	NPC605528
High Similarity	1.0	NPC609573
High Similarity	0.9851	NPC81654
Intermediate Similarity	0.8333	NPC547922
Intermediate Similarity	0.8	NPC533577
Intermediate Similarity	0.8	NPC551430
Intermediate Similarity	0.8	NPC556820
Intermediate Similarity	0.8	NPC584466
Intermediate Similarity	0.7895	NPC511098
Intermediate Similarity	0.7895	NPC519056
Intermediate Similarity	0.7895	NPC526529
Intermediate Similarity	0.7895	NPC529689
Intermediate Similarity	0.7895	NPC557068
Intermediate Similarity	0.7895	NPC559773
Intermediate Similarity	0.7895	NPC596131
Intermediate Similarity	0.7763	NPC64453
Intermediate Similarity	0.7763	NPC574555
Intermediate Similarity	0.7763	NPC592718
Intermediate Similarity	0.7532	NPC506842
Intermediate Similarity	0.7467	NPC486452
Intermediate Similarity	0.7467	NPC253786
Intermediate Similarity	0.7467	NPC74591
Intermediate Similarity	0.7089	NPC514799
Intermediate Similarity	0.7089	NPC578730
Remote Similarity	0.6962	NPC289227
Remote Similarity	0.6923	NPC170067
Remote Similarity	0.6923	NPC486443
Remote Similarity	0.6923	NPC486446
Remote Similarity	0.6923	NPC509472
Remote Similarity	0.6923	NPC586724
Remote Similarity	0.68	NPC270945
Remote Similarity	0.68	NPC15732
Remote Similarity	0.6593	NPC321871
Remote Similarity	0.6593	NPC303096
Remote Similarity	0.6463	NPC572094
Remote Similarity	0.642	NPC50503
Remote Similarity	0.642	NPC539322
Remote Similarity	0.642	NPC553376
Remote Similarity	0.642	NPC607669
Remote Similarity	0.6341	NPC319179
Remote Similarity	0.6296	NPC486449
Remote Similarity	0.6296	NPC63199
Remote Similarity	0.6296	NPC93956
Remote Similarity	0.6296	NPC319597
Remote Similarity	0.6296	NPC111602
Remote Similarity	0.6296	NPC102338
Remote Similarity	0.6296	NPC196251
Remote Similarity	0.6296	NPC255696
Remote Similarity	0.6296	NPC601589
Remote Similarity	0.6296	NPC602673
Remote Similarity	0.6235	NPC8613
Remote Similarity	0.6184	NPC185200
Remote Similarity	0.6024	NPC278785
Remote Similarity	0.6024	NPC175474
Remote Similarity	0.6024	NPC99921
Remote Similarity	0.6024	NPC535924
Remote Similarity	0.5976	NPC516311
Remote Similarity	0.5904	NPC202407
Remote Similarity	0.5904	NPC245312
Remote Similarity	0.5904	NPC206728
Remote Similarity	0.5904	NPC273374
Remote Similarity	0.5904	NPC153585
Remote Similarity	0.5904	NPC47948
Remote Similarity	0.5851	NPC63310
Remote Similarity	0.5851	NPC191489
Remote Similarity	0.5851	NPC611619
Remote Similarity	0.5765	NPC139078
Remote Similarity	0.5714	NPC483467
Remote Similarity	0.5698	NPC312870
Remote Similarity	0.5698	NPC199851
Remote Similarity	0.5698	NPC294909
Remote Similarity	0.5698	NPC254240
Remote Similarity	0.5698	NPC220791
Remote Similarity	0.5698	NPC128265
Remote Similarity	0.5698	NPC312996
Remote Similarity	0.5698	NPC513219
Remote Similarity	0.5698	NPC548074
Remote Similarity	0.5698	NPC552071
Remote Similarity	0.5698	NPC604675
Remote Similarity	0.5682	NPC90545
Remote Similarity	0.5682	NPC303299
Remote Similarity	0.5682	NPC159060
Remote Similarity	0.5682	NPC111858
Remote Similarity	0.5682	NPC515564
Remote Similarity	0.5618	NPC505862
Remote Similarity	0.5506	NPC575218
Remote Similarity	0.55	NPC559722
Remote Similarity	0.55	NPC591443
Remote Similarity	0.5465	NPC107782
Remote Similarity	0.5465	NPC271686
Remote Similarity	0.5465	NPC486454
Remote Similarity	0.5465	NPC608488
Remote Similarity	0.5443	NPC21174
Remote Similarity	0.5393	NPC199393
Remote Similarity	0.5385	NPC313029
Remote Similarity	0.5375	NPC229173
Remote Similarity	0.5375	NPC569899
Remote Similarity	0.5349	NPC516417
Remote Similarity	0.5349	NPC523632
Remote Similarity	0.5244	NPC165441
Remote Similarity	0.5244	NPC509219
Remote Similarity	0.5158	NPC562331
Remote Similarity	0.5138	NPC170039
Remote Similarity	0.5135	NPC522298
Remote Similarity	0.5116	NPC220151
Remote Similarity	0.5116	NPC19692
Remote Similarity	0.5116	NPC522873
Remote Similarity	0.5116	NPC610395
Remote Similarity	0.5111	NPC62418
Remote Similarity	0.5111	NPC113169
Remote Similarity	0.5111	NPC569747
Remote Similarity	0.5067	NPC88097
Remote Similarity	0.5067	NPC155350
Remote Similarity	0.506	NPC474897
Remote Similarity	0.5059	NPC507740
Remote Similarity	0.5056	NPC507600
Remote Similarity	0.5056	NPC611453

Drug Structure

NPD4601 OpenBabel08211705262D 28 32 0 0 1 0 0 0 0 0999 V2000 -0.1219 2.9272 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5151 -1.4518 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5149 -0.4834 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6771 -1.9359 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6767 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1919 1.4507 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1922 2.4185 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6768 -1.9366 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5150 -1.4528 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6774 0.9674 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3534 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3537 0.9670 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8384 -1.4522 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8383 -1.4525 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5157 1.4511 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8382 -0.4838 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6772 -0.0003 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 3.3542 2.9026 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.5159 2.4189 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.8385 -0.4841 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6368 2.9268 0.0000 C 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 2.5152 -0.4844 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 3.3544 3.9179 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6370 3.9421 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.7573 2.4193 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0002 1.0000 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4753 4.4258 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 1 26 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 13 2 0 0 0 0 5 16 2 0 0 0 0 6 7 1 0 0 0 0 7 18 1 0 0 0 0 8 9 1 0 0 0 0 8 14 1 0 0 0 0 9 23 1 0 0 0 0 10 17 1 0 0 0 0 11 12 1 0 0 0 0 11 23 1 0 0 0 0 12 6 1 1 0 0 0 12 15 1 0 0 0 0 13 14 1 0 0 0 0 13 16 1 0 0 0 0 14 20 2 0 0 0 0 15 10 1 6 0 0 0 15 19 1 0 0 0 0 16 22 1 0 0 0 0 17 20 1 0 0 0 0 17 23 1 6 0 0 0 18 19 1 0 0 0 0 18 24 1 1 0 0 0 19 21 1 1 0 0 0 20 22 1 0 0 0 0 21 25 2 0 0 0 0 21 26 1 0 0 0 0 22 27 1 0 0 0 0 24 28 1 0 0 0 0 M END $$$$

External Identifiers

TTD	DAP000087
DrugBank	DB01392
ChEMBL	CHEMBL15245
IUPHAR/BPS	102
PharmaGKB	PA451946
KEGG Drug
PubChem CID	8969
ChEBI	10093
CAS Number	146-48-5

Drug Properties

Molecular Weight	354.19
ALogP	-1.212
MLogP	3.22
XLogP	2.857
HDA	5
HBD	2
Rotatable Bonds	4
TPSA	65.56
RO5 Violation	0