Compound Detail

CHEMBL15245

YOHIMBINE

🧪 Phase III

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🧪 Phase III

COC(=O)[C@@H]1[C@H]2C[C@H]3c4[nH]c5ccccc5c4CCN3C[C@@H]2CC[C@@H]1O

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL15245
Name	YOHIMBINE
Phase	Phase III
Structure Type	MOL
InChI Key	BLGXFZZNTVWLAY-SCYLSFHTSA-N
Therapeutic	✓ Yes

Known Names

Yohimbine Yohimbinum

Targets

212

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

354.4

MW (Da)

2.65

ALogP

HBA

HBD

65.6

PSA (Å²)

0.77

QED

Ro5 Violations

Rot. Bonds

Drug Information

Molecule Type	Small molecule
Chirality	Single Enantiomer

Flags

Natural Product

Extended Properties

Molecular Formula	C21H26N2O3
MW	354.45
Aromatic Rings	2
Heavy Atoms	26
NP-Likeness	1.17

Indications

Erectile Dysfunction Alcoholism Cocaine-Related Disorders Diabetes Mellitus, Type 2 Opioid-Related Disorders Stress Disorders, Post-Traumatic Hypotension, Orthostatic Marijuana Abuse Orthostatic Intolerance Parkinson Disease

ATC Classification

G04BE04

yohimbine

Level 1: GENITO URINARY SYSTEM AND SEX HORMONES

Level 2: UROLOGICALS

Activity Summary

Ki 116 meas. best 10.4

IC50 51 meas. best 8.21

Kd 42 meas. best 8.32

EC50 3 meas. best 8.07

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
Beta-2 adrenergic receptor CHEMBL210	Ki	10.4	10.4	0.0	1
Alpha-2C adrenergic receptor CHEMBL1916	Ki	9.6	8.9778	0.3	9
Adrenergic receptor alpha-2 CHEMBL2095158	Ki	9.4	8.25	0.4	13
Alpha-2A adrenergic receptor CHEMBL1867	Ki	9.38	8.5464	0.4	11
Alpha-2 adrenergic receptor CHEMBL2111338	Ki	9.22	8.3033	0.6	3
Adrenergic receptor alpha-2 CHEMBL2093864	Ki	9.22	7.6884	0.6	19
Alpha-1B adrenergic receptor CHEMBL232	Ki	8.96	7.4775	1.1	4
Alpha-2B adrenergic receptor CHEMBL1942	Ki	8.94	8.304	1.2	10
Alpha-1D adrenergic receptor CHEMBL223	Ki	8.8	7.11	1.6	4
Alpha-2B adrenergic receptor CHEMBL266	Ki	8.7	8.7	2.0	1
Alpha-1A adrenergic receptor CHEMBL4892	Ki	8.44	7.115	3.6	4
Alpha-2A adrenergic receptor CHEMBL2350	Ki	8.36	8.36	4.4	1
Alpha-2A adrenergic receptor CHEMBL1867	Kd	8.32	8.205	4.8	2
Alpha-2A adrenergic receptor CHEMBL1867	IC50	8.21	8.035	6.2	4
Adrenergic receptor alpha-1 CHEMBL1907610	Kd	8.14	6.5827	7.2	11
Alpha-2C adrenergic receptor CHEMBL1916	IC50	8.11	7.775	7.7	2
Adrenergic receptor alpha-2 CHEMBL2095158	IC50	8.1	7.0514	8.0	7
Cytochrome P450 2D6 CHEMBL289	IC50	8.08	6.885	8.4	2
Alpha-2A adrenergic receptor CHEMBL1867	EC50	8.07	7.945	8.5	2
Adrenergic receptor alpha-2 CHEMBL2093864	IC50	8.04	7.2888	9.1	8
Alpha-2 adrenergic receptor CHEMBL2111338	Kd	7.98	7.98	10.5	1
Adrenergic receptor alpha-2 CHEMBL2093864	Kd	7.91	7.56	12.3	11
Cavia porcellus CHEMBL369	Kd	7.9	7.9	12.6	1
Alpha-2B adrenergic receptor CHEMBL1942	IC50	7.77	7.415	17.0	2
Rattus norvegicus CHEMBL376	Kd	7.65	7.085	22.4	2
5-hydroxytryptamine receptor 1D CHEMBL1983	Ki	7.6	7.6	25.1	1
Adrenergic receptor alpha-2 CHEMBL2095158	Kd	7.59	6.2322	25.7	9
Unchecked CHEMBL612545	Ki	7.48	7.285	33.0	4
Unchecked CHEMBL612545	IC50	7.42	7.0733	38.0	3
5-hydroxytryptamine receptor 2B CHEMBL1833	Ki	7.37	7.35	43.0	2
Voltage-dependent L-type calcium channel subunit alpha-1C CHEMBL3762	Ki	7.35	7.35	45.0	1
Alpha-2A adrenergic receptor CHEMBL4744	Ki	7.31	7.31	49.0	2
5-hydroxytryptamine receptor 1A CHEMBL214	Ki	7.3	7.3	50.1	1
Alpha-1D adrenergic receptor CHEMBL326	Ki	7.28	7.28	52.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	Ki	7.14	7.14	72.0	1
5-hydroxytryptamine receptor 2B CHEMBL1833	IC50	7.13	7.13	74.0	1
5-hydroxytryptamine receptor 1A CHEMBL273	IC50	6.9	6.9	126.0	1
Cytochrome P450 2D6 CHEMBL289	Ki	6.85	6.6771	140.0	7
Adrenergic receptor alpha-1 CHEMBL2094251	Kd	6.83	6.465	147.9	2
5-hydroxytryptamine receptor 1B CHEMBL1898	Ki	6.8	6.8	158.5	1
Alpha-1A adrenergic receptor CHEMBL229	Ki	6.7	6.34	199.5	2
Adrenergic receptor alpha-1 CHEMBL1907610	Ki	6.44	6.41	360.0	4
Alpha-1A adrenergic receptor CHEMBL229	Kd	6.4	6.4	398.1	1
D(2) dopamine receptor CHEMBL217	Ki	6.4	6.28	398.1	2
Alpha-1A adrenergic receptor CHEMBL319	Ki	6.3	6.3	500.0	1
Rattus norvegicus CHEMBL376	Ki	6.3	6.3	505.0	1
Alpha-1B adrenergic receptor CHEMBL315	Ki	6.18	6.18	658.0	1
5-hydroxytryptamine receptor 6 CHEMBL3371	Ki	6.11	6.11	784.0	1
Adrenergic receptor alpha-1 CHEMBL1907610	IC50	6.0	5.8967	1000.0	3
Alpha-1D adrenergic receptor CHEMBL223	IC50	5.99	5.99	1013.0	1

Pharmacokinetic Data

Parameter	Value	Units	Species
CL	34.4	mL.min-1.g-1	Homo sapiens
CL	7.0	mL.min-1.g-1	Homo sapiens
CL	2.0	mL.min-1.g-1	Rattus norvegicus
T1/2	0.06167	hr	Mus musculus
T1/2	1.0	hr	Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
Beta-2 adrenergic receptor	Ki	=	0.04	nM	10.4	Binding affinity to human beta 2 adrenergic receptor assessed as inhibition cons...	38516587
Alpha-2C adrenergic receptor	Ki	=	0.2512	nM	9.6	Displacement of [3H]RX821,002 from human ADRA2C expressed in CHO cells	38857067
Adrenergic receptor alpha-2	Ki	=	0.4	nM	9.4	Compound was evaluated for inhibition of binding of [3H]yohimbine to Alpha-2 adr...	7658428
Alpha-2A adrenergic receptor	Ki	=	0.42	nM	9.38	Binding affinity against human Alpha-2A adrenergic receptor expressed stably in ...	10762040
Alpha-2C adrenergic receptor	Ki	=	0.5	nM	9.3	Displacement of [3H]RX821002 from human recombinant alpha2C adrenoceptor express...	24805037
Alpha-2C adrenergic receptor	Ki	=	0.5	nM	9.3	Displacement of [3H]RX-821002 from human adrenergic alpha2C receptor expressed i...	25557493
Alpha-2 adrenergic receptor	Ki	=	0.6	nM	9.22	Compound was evaluated for inhibition of binding of [3H]yohimbine to Alpha-2 adr...	7658428
Adrenergic receptor alpha-2	Ki	=	0.6	nM	9.22	Compound was evaluated for inhibition of binding of [3H]yohimbine to Alpha-2 adr...	7658428
Adrenergic receptor alpha-2	Ki	=	0.6	nM	9.22	Compound was evaluated for inhibition of binding of [3H]-yohimbine to Alpha-2 ad...	7658428
Alpha-2C adrenergic receptor	Ki	=	0.8	nM	9.1	Displacement of [3H]RX 821002 from human recombinant adrenergic alpha-2C recepto...	31834797
Alpha-2C adrenergic receptor	Ki	=	0.88	nM	9.06	In vitro binding affinity measured by displacement of [3H]rauwolscine from alpha...	15911252
Adrenergic receptor alpha-2	Ki	=	0.9	nM	9.05	Compound was evaluated for inhibition of binding of [3H]yohimbine to Alpha-2 adr...	7658428
Adrenergic receptor alpha-2	Ki	=	1.0	nM	9.0	Compound was evaluated for inhibition of binding of [3H]yohimbine to Alpha-2 adr...	7658428
Alpha-1B adrenergic receptor	Ki	=	1.1	nM	8.96	Binding affinity against Alpha-1B adrenergic receptor from hamster clones.	7658428
Alpha-2B adrenergic receptor	Ki	=	1.16	nM	8.94	Displacement of [3H]RX 821002 from human recombinant adrenergic alpha-2B recepto...	31834797
Alpha-2A adrenergic receptor	Ki	=	1.4	nM	8.85	In vitro binding affinity towards alpha-2a adrenergic receptor	15911252
Alpha-2C adrenergic receptor	Ki	=	1.549	nM	8.81	Displacement of [3H]-rauwolscine from human recombinant adrenergic alpha-2C rece...	38593423
Alpha-1D adrenergic receptor	Ki	=	1.6	nM	8.8	Binding affinity against Alpha-1D adrenergic receptor, from human clones.	7658428
Adrenergic receptor alpha-2	Ki	=	1.8	nM	8.74	Compound was evaluated for inhibition of binding of [3H]yohimbine to Alpha-2 adr...	7658428
Alpha-2B adrenergic receptor	Ki	=	1.995	nM	8.7	Displacement of [3H]RX821,002 from human ADRA2B expressed in CHO cells	38857067

Literature References

PubMed	DOI	Target Context	# Activities
7658428	10.1021/jm00018a001	Adrenergic receptor alpha-2	19
38857067	10.1021/acs.jmedchem.4c00323	ADMET	13
-	10.1016/0960-894X(96)00406-4	Adrenergic receptor alpha-2	12
16407989	10.1038/nchembio705	Alpha-2A adrenergic receptor	12
38857067	10.1021/acs.jmedchem.4c00323	Alpha-2A adrenergic receptor	8
37468498	10.1038/s41467-023-40064-9	D(1A) dopamine receptor	7
37468498	10.1038/s41467-023-40064-9	Alpha-1A adrenergic receptor	7
8487254	10.1021/jm00061a004	Cytochrome P450 2D6	6
37468498	10.1038/s41467-023-40064-9	Alpha-2A adrenergic receptor	5
11602674	-	ATP-dependent translocase ABCB1	5
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 2B	4
37468498	10.1038/s41467-023-40064-9	5-hydroxytryptamine receptor 1A	4
37468498	10.1038/s41467-023-40064-9	Muscarinic acetylcholine receptor M2	4
17181165	10.1021/jm060743g	Mus musculus	4
2887657	10.1021/jm00392a005	Adrenergic receptor alpha-2	4
2570150	10.1021/jm00129a002	Unchecked	3
23403082	10.1016/j.bmcl.2013.01.025	Alpha-2A adrenergic receptor	3
1671705	10.1021/jm00106a036	Adrenergic receptor alpha-2	3
2886664	10.1021/jm00391a015	Adrenergic receptor alpha-1	3
37468498	10.1038/s41467-023-40064-9	Sodium-dependent dopamine transporter	3

Data from ChEMBL 36 via Core Engine