NPASS drugs

Drug Information

Drug ID:	NPD4600
Drug Name:	Yohimbine Hydrochloride
Molecular Formula:	C21H26N2O3.ClH
Canonical SMILES:	COC(=O)[C@H]1[C@@H](O)CC[C@@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1.Cl
Standard InCHI:	"InChI=1S/C21H26N2O3.ClH/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;1H/t12-,15-,17-,18-,19+;/m0./s1"
Standard InCHIKey:	PIPZGJSEDRMUAW-VJDCAHTMSA-N
Max Developmental Stage:	Approved
Max Developmental Stage Source:	ChEMBL

Structural Similarity Between NPASS Natural Products and NPD4600

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	77487
0.1-0.2	130327
0.2-0.3	3114
0.3-0.4	517
0.4-0.5	169
0.5-0.6	59
0.6-0.7	28
0.7-0.8	20
0.8-0.85	1
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	NPC81654
High Similarity	0.9851	NPC284075
High Similarity	0.9851	NPC313985
High Similarity	0.9851	NPC249150
High Similarity	0.9851	NPC326180
High Similarity	0.9851	NPC33619
High Similarity	0.9851	NPC540096
High Similarity	0.9851	NPC572911
High Similarity	0.9851	NPC581804
High Similarity	0.9851	NPC604228
High Similarity	0.9851	NPC605528
High Similarity	0.9851	NPC609573
Intermediate Similarity	0.8219	NPC547922
Intermediate Similarity	0.7895	NPC533577
Intermediate Similarity	0.7895	NPC551430
Intermediate Similarity	0.7895	NPC556820
Intermediate Similarity	0.7895	NPC584466
Intermediate Similarity	0.7792	NPC511098
Intermediate Similarity	0.7792	NPC519056
Intermediate Similarity	0.7792	NPC526529
Intermediate Similarity	0.7792	NPC529689
Intermediate Similarity	0.7792	NPC557068
Intermediate Similarity	0.7792	NPC559773
Intermediate Similarity	0.7792	NPC596131
Intermediate Similarity	0.7662	NPC64453
Intermediate Similarity	0.7662	NPC574555
Intermediate Similarity	0.7662	NPC592718
Intermediate Similarity	0.7436	NPC506842
Intermediate Similarity	0.7368	NPC486452
Intermediate Similarity	0.7368	NPC253786
Intermediate Similarity	0.7368	NPC74591
Intermediate Similarity	0.7	NPC514799
Intermediate Similarity	0.7	NPC578730
Remote Similarity	0.6875	NPC289227
Remote Similarity	0.6835	NPC170067
Remote Similarity	0.6835	NPC486443
Remote Similarity	0.6835	NPC486446
Remote Similarity	0.6835	NPC509472
Remote Similarity	0.6835	NPC586724
Remote Similarity	0.6711	NPC270945
Remote Similarity	0.6711	NPC15732
Remote Similarity	0.6522	NPC321871
Remote Similarity	0.6522	NPC303096
Remote Similarity	0.6386	NPC572094
Remote Similarity	0.6341	NPC50503
Remote Similarity	0.6341	NPC539322
Remote Similarity	0.6341	NPC553376
Remote Similarity	0.6341	NPC607669
Remote Similarity	0.6265	NPC319179
Remote Similarity	0.622	NPC486449
Remote Similarity	0.622	NPC63199
Remote Similarity	0.622	NPC93956
Remote Similarity	0.622	NPC319597
Remote Similarity	0.622	NPC111602
Remote Similarity	0.622	NPC102338
Remote Similarity	0.622	NPC196251
Remote Similarity	0.622	NPC255696
Remote Similarity	0.622	NPC601589
Remote Similarity	0.622	NPC602673
Remote Similarity	0.6163	NPC8613
Remote Similarity	0.6104	NPC185200
Remote Similarity	0.5952	NPC278785
Remote Similarity	0.5952	NPC175474
Remote Similarity	0.5952	NPC99921
Remote Similarity	0.5952	NPC535924
Remote Similarity	0.5904	NPC516311
Remote Similarity	0.5833	NPC202407
Remote Similarity	0.5833	NPC245312
Remote Similarity	0.5833	NPC206728
Remote Similarity	0.5833	NPC273374
Remote Similarity	0.5833	NPC153585
Remote Similarity	0.5833	NPC47948
Remote Similarity	0.5789	NPC63310
Remote Similarity	0.5789	NPC191489
Remote Similarity	0.5789	NPC611619
Remote Similarity	0.5698	NPC139078
Remote Similarity	0.5647	NPC483467
Remote Similarity	0.5632	NPC312870
Remote Similarity	0.5632	NPC199851
Remote Similarity	0.5632	NPC294909
Remote Similarity	0.5632	NPC254240
Remote Similarity	0.5632	NPC220791
Remote Similarity	0.5632	NPC128265
Remote Similarity	0.5632	NPC312996
Remote Similarity	0.5632	NPC513219
Remote Similarity	0.5632	NPC548074
Remote Similarity	0.5632	NPC552071
Remote Similarity	0.5632	NPC604675
Remote Similarity	0.5618	NPC90545
Remote Similarity	0.5618	NPC303299
Remote Similarity	0.5618	NPC159060
Remote Similarity	0.5618	NPC111858
Remote Similarity	0.5618	NPC515564
Remote Similarity	0.5556	NPC505862
Remote Similarity	0.5444	NPC575218
Remote Similarity	0.5432	NPC559722
Remote Similarity	0.5432	NPC591443
Remote Similarity	0.5402	NPC107782
Remote Similarity	0.5402	NPC271686
Remote Similarity	0.5402	NPC486454
Remote Similarity	0.5402	NPC608488
Remote Similarity	0.5375	NPC21174
Remote Similarity	0.5333	NPC199393
Remote Similarity	0.5316	NPC313029
Remote Similarity	0.5309	NPC229173
Remote Similarity	0.5309	NPC569899
Remote Similarity	0.5287	NPC516417
Remote Similarity	0.5287	NPC523632
Remote Similarity	0.5181	NPC165441
Remote Similarity	0.5181	NPC509219
Remote Similarity	0.5104	NPC562331
Remote Similarity	0.5091	NPC170039
Remote Similarity	0.5067	NPC522298
Remote Similarity	0.5057	NPC220151
Remote Similarity	0.5057	NPC19692
Remote Similarity	0.5057	NPC522873
Remote Similarity	0.5057	NPC610395
Remote Similarity	0.5055	NPC62418
Remote Similarity	0.5055	NPC113169
Remote Similarity	0.5055	NPC569747

Drug Structure

NPD4600 OpenBabel08211705262D 29 32 0 0 1 0 0 0 0 0999 V2000 2.8932 -1.9986 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5000 -6.3776 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5002 -5.4092 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3380 -6.8617 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3384 -4.9255 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2070 -3.4751 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2072 -2.5074 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6919 -6.8624 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5301 -6.3786 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6925 -3.9584 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3685 -4.9266 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3687 -3.9588 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1767 -6.3780 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8534 -6.3783 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5307 -3.4747 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 2.1769 -5.4096 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6923 -4.9261 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 6.3692 -2.0232 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 5.5310 -2.5069 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.8536 -5.4099 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6518 -1.9990 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0151 -4.9258 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 5.5302 -5.4102 0.0000 N 0 0 3 0 0 0 0 0 0 0 0 0 6.3695 -1.0079 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6521 -0.9837 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7724 -2.5065 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3223 -0.6171 0.0000 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.0153 -3.9258 0.0000 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4903 -0.5000 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 28 1 0 0 0 0 24 29 1 0 0 0 0 M END $$$$

External Identifiers

TTD
DrugBank
ChEMBL
IUPHAR/BPS
PharmaGKB
KEGG Drug
PubChem CID	0
ChEBI
CAS Number

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