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:	Approved
Max Developmental Stage Source:	TTD; ChEMBL; IUPHAR/BPS

Structural Similarity Between NPASS Natural Products and NPD4601

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	188
0.1-0.2	1030
0.2-0.3	3808
0.3-0.4	15647
0.4-0.5	6547
0.5-0.6	1854
0.6-0.7	1262
0.7-0.8	473
0.8-0.85	56
0.85-0.9	16
0.9-0.95	2
0.95-1	7

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
High Similarity	1.0	NPC81654
High Similarity	1.0	NPC79129
High Similarity	1.0	NPC49196
High Similarity	1.0	NPC313985
High Similarity	1.0	NPC195461
High Similarity	1.0	NPC249150
High Similarity	0.9887	NPC50503
High Similarity	0.9435	NPC175474
High Similarity	0.9235	NPC52557
High Similarity	0.8696	NPC196251
High Similarity	0.8696	NPC102338
High Similarity	0.8696	NPC111602
High Similarity	0.8696	NPC63199
High Similarity	0.8649	NPC472112
High Similarity	0.8626	NPC472108
High Similarity	0.8626	NPC139291
High Similarity	0.8556	NPC472113
High Similarity	0.8541	NPC472323
High Similarity	0.8534	NPC312870
High Similarity	0.8534	NPC128265
High Similarity	0.8534	NPC199851
High Similarity	0.8534	NPC294909
High Similarity	0.8534	NPC254240
High Similarity	0.852	NPC234999
High Similarity	0.8516	NPC15840
Intermediate Similarity	0.8462	NPC219336
Intermediate Similarity	0.8446	NPC162730
Intermediate Similarity	0.8444	NPC472123
Intermediate Similarity	0.8432	NPC472107
Intermediate Similarity	0.8432	NPC79062
Intermediate Similarity	0.8415	NPC469896
Intermediate Similarity	0.8407	NPC183662
Intermediate Similarity	0.8407	NPC217372
Intermediate Similarity	0.8407	NPC15573
Intermediate Similarity	0.8368	NPC85066
Intermediate Similarity	0.8368	NPC181502
Intermediate Similarity	0.8351	NPC474116
Intermediate Similarity	0.8342	NPC475778
Intermediate Similarity	0.8325	NPC245916
Intermediate Similarity	0.8324	NPC472110
Intermediate Similarity	0.8324	NPC472109
Intermediate Similarity	0.828	NPC472119
Intermediate Similarity	0.8278	NPC317430
Intermediate Similarity	0.8276	NPC52254
Intermediate Similarity	0.8272	NPC19692
Intermediate Similarity	0.8272	NPC220151
Intermediate Similarity	0.8254	NPC329858
Intermediate Similarity	0.8226	NPC143533
Intermediate Similarity	0.8212	NPC271797
Intermediate Similarity	0.8212	NPC21174
Intermediate Similarity	0.8197	NPC329688
Intermediate Similarity	0.8197	NPC189812
Intermediate Similarity	0.8182	NPC258480
Intermediate Similarity	0.8168	NPC55493
Intermediate Similarity	0.8158	NPC469501
Intermediate Similarity	0.8158	NPC314333
Intermediate Similarity	0.8158	NPC469470
Intermediate Similarity	0.8152	NPC24594
Intermediate Similarity	0.8152	NPC472122
Intermediate Similarity	0.8137	NPC82070
Intermediate Similarity	0.8128	NPC476114
Intermediate Similarity	0.8128	NPC19679
Intermediate Similarity	0.8103	NPC241024
Intermediate Similarity	0.8095	NPC66210
Intermediate Similarity	0.8083	NPC289299
Intermediate Similarity	0.8083	NPC57994
Intermediate Similarity	0.8049	NPC281049
Intermediate Similarity	0.8049	NPC174788
Intermediate Similarity	0.8048	NPC33949
Intermediate Similarity	0.804	NPC18661
Intermediate Similarity	0.8032	NPC472104
Intermediate Similarity	0.8031	NPC472295
Intermediate Similarity	0.8031	NPC81802
Intermediate Similarity	0.8031	NPC269886
Intermediate Similarity	0.8031	NPC472210
Intermediate Similarity	0.8031	NPC247735
Intermediate Similarity	0.8029	NPC475271
Intermediate Similarity	0.8021	NPC472105
Intermediate Similarity	0.8021	NPC187827
Intermediate Similarity	0.8021	NPC472097
Intermediate Similarity	0.8	NPC478077
Intermediate Similarity	0.7979	NPC113626
Intermediate Similarity	0.7968	NPC213468
Intermediate Similarity	0.7941	NPC221100
Intermediate Similarity	0.7941	NPC234078
Intermediate Similarity	0.7921	NPC469743
Intermediate Similarity	0.7921	NPC478158
Intermediate Similarity	0.7914	NPC326575
Intermediate Similarity	0.791	NPC477065
Intermediate Similarity	0.7906	NPC235684
Intermediate Similarity	0.7906	NPC62749
Intermediate Similarity	0.7889	NPC476874
Intermediate Similarity	0.7879	NPC214428
Intermediate Similarity	0.7876	NPC95783
Intermediate Similarity	0.7864	NPC330009
Intermediate Similarity	0.7864	NPC148183
Intermediate Similarity	0.7864	NPC152768
Intermediate Similarity	0.7864	NPC469928
Intermediate Similarity	0.7861	NPC267885
Intermediate Similarity	0.7857	NPC472116
Intermediate Similarity	0.7849	NPC161861
Intermediate Similarity	0.7831	NPC91179
Intermediate Similarity	0.782	NPC21638
Intermediate Similarity	0.7819	NPC234987
Intermediate Similarity	0.7816	NPC478157
Intermediate Similarity	0.7812	NPC315555
Intermediate Similarity	0.7812	NPC99428
Intermediate Similarity	0.7807	NPC110500
Intermediate Similarity	0.7807	NPC149155
Intermediate Similarity	0.7807	NPC203468
Intermediate Similarity	0.7789	NPC249040
Intermediate Similarity	0.7784	NPC206967
Intermediate Similarity	0.7784	NPC78020
Intermediate Similarity	0.7784	NPC154293
Intermediate Similarity	0.7778	NPC248041
Intermediate Similarity	0.7778	NPC126709
Intermediate Similarity	0.7778	NPC133261
Intermediate Similarity	0.7772	NPC277350
Intermediate Similarity	0.7761	NPC476098
Intermediate Similarity	0.7756	NPC204303
Intermediate Similarity	0.7737	NPC300688
Intermediate Similarity	0.7736	NPC235885
Intermediate Similarity	0.7732	NPC321708
Intermediate Similarity	0.7725	NPC14113
Intermediate Similarity	0.7725	NPC145885
Intermediate Similarity	0.7725	NPC84827
Intermediate Similarity	0.7723	NPC185742
Intermediate Similarity	0.7723	NPC475847
Intermediate Similarity	0.7707	NPC475422
Intermediate Similarity	0.7704	NPC472292
Intermediate Similarity	0.7696	NPC87755
Intermediate Similarity	0.7692	NPC203614
Intermediate Similarity	0.7692	NPC204491
Intermediate Similarity	0.7684	NPC55772
Intermediate Similarity	0.7684	NPC283219
Intermediate Similarity	0.7681	NPC54744
Intermediate Similarity	0.768	NPC119700
Intermediate Similarity	0.7677	NPC231342
Intermediate Similarity	0.7673	NPC165599
Intermediate Similarity	0.766	NPC97525
Intermediate Similarity	0.7659	NPC162860
Intermediate Similarity	0.7653	NPC243716
Intermediate Similarity	0.765	NPC473105
Intermediate Similarity	0.7644	NPC313640
Intermediate Similarity	0.7637	NPC285469
Intermediate Similarity	0.7633	NPC75634
Intermediate Similarity	0.7632	NPC111275
Intermediate Similarity	0.7632	NPC151939
Intermediate Similarity	0.763	NPC472099
Intermediate Similarity	0.7617	NPC165201
Intermediate Similarity	0.7617	NPC472294
Intermediate Similarity	0.7609	NPC81229
Intermediate Similarity	0.7609	NPC255229
Intermediate Similarity	0.7604	NPC475720
Intermediate Similarity	0.7604	NPC302191
Intermediate Similarity	0.7604	NPC71037
Intermediate Similarity	0.7604	NPC474192
Intermediate Similarity	0.7598	NPC238457
Intermediate Similarity	0.7596	NPC472291
Intermediate Similarity	0.7588	NPC472293
Intermediate Similarity	0.7586	NPC476115
Intermediate Similarity	0.7581	NPC470508
Intermediate Similarity	0.7574	NPC475506
Intermediate Similarity	0.7568	NPC16667
Intermediate Similarity	0.7562	NPC472297
Intermediate Similarity	0.7562	NPC472296
Intermediate Similarity	0.7561	NPC474905
Intermediate Similarity	0.7561	NPC54420
Intermediate Similarity	0.7558	NPC14288
Intermediate Similarity	0.7552	NPC198339
Intermediate Similarity	0.7538	NPC474121
Intermediate Similarity	0.7537	NPC193761
Intermediate Similarity	0.7537	NPC155143
Intermediate Similarity	0.7536	NPC96321
Intermediate Similarity	0.7536	NPC473041
Intermediate Similarity	0.7526	NPC228835
Intermediate Similarity	0.7523	NPC64216
Intermediate Similarity	0.7522	NPC284685
Intermediate Similarity	0.7512	NPC477175
Intermediate Similarity	0.7512	NPC322135
Intermediate Similarity	0.7512	NPC470730
Intermediate Similarity	0.7512	NPC306376
Intermediate Similarity	0.7512	NPC102008
Intermediate Similarity	0.7512	NPC2395
Intermediate Similarity	0.7511	NPC470784
Intermediate Similarity	0.75	NPC11445
Intermediate Similarity	0.75	NPC201700
Intermediate Similarity	0.75	NPC261251
Intermediate Similarity	0.75	NPC98715
Intermediate Similarity	0.7489	NPC191489
Intermediate Similarity	0.7488	NPC271862
Intermediate Similarity	0.7488	NPC305984
Intermediate Similarity	0.7488	NPC477548
Intermediate Similarity	0.7488	NPC312645
Intermediate Similarity	0.7488	NPC300183
Intermediate Similarity	0.7486	NPC207726
Intermediate Similarity	0.7477	NPC475816
Intermediate Similarity	0.7477	NPC475969
Intermediate Similarity	0.7477	NPC475859
Intermediate Similarity	0.7476	NPC244741

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