UCSF

ZINC03860825

Draw Identity 99% 90% 80% 70%

Substance Information

In ZINC since Heavy atoms Benign functionality
October 3rd, 2005 26 Yes

Popular Name: Yohimbine Hydrochloride Yohimbine Hydrochloride

Find On: PubMed — Wikipedia — Google

CAS Numbers: 146-48-5 , 51811-82-6 , 65-19-0 , [65-19-0]

Other Names:

(+)-Yohimbin

(+)-Yohimbine

(+)-yohimbine; (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester; 17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester; Johimbin; Quebrachin; Yohimbin; Yohimbine; aphrodine; corynine; quebrachine; yohimbic acid methyl ester

(16alpha,17alpha)-17-Hydroxy-yohimban-16-carboxylic acid methyl ester

(16alpha,17alpha)-17-hydroxyyohimban-16-carboxylic acid methyl ester

146-48-5

146-48-5; C09256; Yohimbine

146-48-5; D08685; Yohimbine (DCF)

17-Hydroxy-yohimbane-16-carboxylic acid methyl ester

17-Hydroxyyohimban-16-carboxylic acid methyl ester

17-Hydroxyyohimban-16-carboxylic acid methyl ester hydrochloride

17alpha-Hydroxy-20-alpha-yohimban-16-beta-carboxylic acid, methyl ester, hydrochloride; AI3-60247; Antagonil; Aphrodine hydrochloride; C21H26N2O3.HCl; EINECS 200-600-4; LS-162742; NSC 19509; Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl est

17alpha-hydroxyyohimban-16alpha-carboxylic acid methyl ester

2-Hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-indolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylic acid methyl ester

4-25-00-01237 (Beilstein Handbook Reference)

65-19-0

65-19-0; D06671; Yohimbine hydrochloride (USP)

65-19-0; Prestwick_961; Yohimbine hydrochloride

70

AC1L1S1D

Actibine

Antagonil, Yohimbe, Aphrodine hydrochloride, Yohimbine monohydrochloride

APHRODINE

Aphrodyne

Aphrosol

Baron-X

BCBcMAP01_000032

Benz[g]indolo[2,3-a]quinolizine, yohimban-16-carboxylic acid deriv.

Bio1_000455

Bio1_000944

Bio1_001433

Bio2_000458

Bio2_000938

BPBio1_000472

BRD-A87445400-003-02-8

BRD-K35586044-001-02-6

BRD-K35586044-003-03-0

BRN 0097276

BSPBio_000428

BSPBio_001236

C09256

CHEBI:10093

CHEMBL15245

CID8969

Corynine

D08685

DAP000087

Dayto himbin

DB01392

DNC009968

EINECS 205-672-0

Giemsa Stain

HMS1362N17

HMS1792N17

HMS1990N17

HMS2089G19

I14-13374

IDI1_002213

InChI=1/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/s

Johimbin

KBio2_000576

KBio2_003144

KBio2_005712

KBio3_001031

KBio3_001032

KBioGR_000576

KBioSS_000576

LS-162738

methyl (16alpha,17alpha)-17-hydroxyyohimban-16-carboxylate

methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate

methyl 17alpha-hydroxyyohimban-16alpha-carboxylate

MFCD00012674

MFCD00081642

MLS000728591

MLS001333983

MolPort-001-794-653

NCGC00025018-05

NCGC00025018-06

NCGC00025018-07

nchembio.188-comp13

nchembio705-2

NSC19509

Prestwick0_000584

Prestwick1_000584

Prestwick2_000584

Prestwick3_000584

Quebrachin

Quebrachine

SMP1_000320

SMR000058527

SMR000470778

SPBio_002647

STOCK1N-51304

Thybine

trans-Quinolizidine yohimbine

UNII-2Y49VWD90Q

Yocon

Yohimar

Yohimban-16-.alpha.-carboxylic acid, 17-.alpha.-hydroxy-, methyl ester

Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl ester

Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)-

Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17alpha)- (9CI)

Yohimban-16alpha-carboxylic acid, 17alpha-hydroxy-, methyl ester (8CI)

Yohimbic acid methyl ester

Yohimbin

Yohimbine

Yohimbine (DCF)

Yohimbine HCl

Yohimbine HCl (USP)

Yohimbine hydrochloride (Antagonil)

Yohimbine Hydrochloride (USP)

Yohimbine Hydrochloride [65-19-0]

Yohimbine hydrochloride, 99%

YOHIMBINE HYDROCHLORIDE; [65-19-0]

Yohimbine, HCl

Yohimbine.HCl

Yohimbol-16alpha-carboxylic acid, methyl ester (6CI)

Yohimex

Yoman

Yovital

Download: MOL2 SDF SMILES Flexibase

Annotations

Vendors

Physical Representations

Type pH range xlogP Des A‑Pol Apolar desolvation (kcal/mol) Des Pol Polar desolvation (kcal/mol) H Don H-bond donors H Acc H-bond acceptors Chg Net charge tPSA (Ų) MWT Molecular weight (g/mol) RB Rotatable bonds DL
Ref Reference (pH 7) 3.22 8.17 -43.2 3 5 1 67 355.458 2 ↓
Hi High (pH 8-9.5) 3.22 6.05 -10.14 2 5 0 66 354.45 2 ↓

Vendor Notes

Note Type Comments Provided By
Molecular_Solubility 3.74 Bitter DB
Mp [°C] 285 - 288 Acros Organics
MP 288-290 °C (dec.)(lit.) Indofine
ALOGPS_SOLUBILITY 3.48e-01 g/l DrugBank-approved
Purity >99% Fluorochem
UniProt Database Links ADA2A_HUMAN; ADA2B_HUMAN; OAR1_LOCMI; OAR1_LYMST; OAR2_LYMST; OAR_DROME ChEBI
Therapy alpha adrenergic blocker, mydriatic, antidepressant SMDC Pharmakon
Therapy alpha2 Adrenoceptor antagonist isolated from Cortnanthe johimbe SMDC Iconix
Melting_Point ca 300? Alfa-Aesar
Melting_Point ca 300° Alfa-Aesar
Patent Database Links EP1700601; EP1762236; US2004092536; US2006040929; US2007112067; US2007190023; US2007196511; US2007212429; US2007232698; US2007238762; US2008280919; WO2006091697; WO2007087367; WO2007098390; WO2007101349 ChEBI
SOLUBILITY H2O: 10 mg/mL Indofine
H phrase H311: Toxic in contact with skin Acros Organics
H phrase H311: Toxic in contact with skin; H373: May cause damage to organs through prolonged or repeated exposure; H331: Toxic if inhaled Acros Organics
Target NULL Selleck Chemicals
P phrase P280: Wear protective gloves/protective clothing/eye protection/face protection Acros Organics
P phrase P280: Wear protective gloves/protective clothing/eye protection/face protection; P312: Call a POISON CENTER or doctor/physician if you feel unwell; P302 + P350: IF ON SKIN: Gently wash with plenty of soap and water; P304 + P340: IF INHALED: Remove victim Acros Organics
R phrase R23/24: Toxic by inhalation and in contact with skin. Acros Organics
R phrase R23/24: Toxic by inhalation and in contact with skin.; R33: Danger of cumulative effects. Acros Organics
Reactome Database Links REACT_15538; REACT_163726; REACT_22239; REACT_22289 ChEBI
S phrase S24/25: Avoid contact with skin and eyes. Acros Organics
Hazard T: Toxic Acros Organics

Activity (Go SEA)

Clustered Target Annotations
Code Description Organism Class Affinity (nM) LE (kcal/mol/atom) Type
5HT2A-1-E Serotonin 2a (5-HT2a) Receptor (cluster #1 Of 3), Eukaryotic Eukaryotes 1622 0.31 Binding ≤ 10μM
5HT2C-1-E Serotonin 2c (5-HT2c) Receptor (cluster #1 Of 3), Eukaryotic Eukaryotes 10000 0.27 Binding ≤ 10μM
AA3R-1-E Adenosine Receptor A3 (cluster #1 Of 6), Eukaryotic Eukaryotes 95 0.38 Binding ≤ 10μM
ADA1A-1-E Alpha-1a Adrenergic Receptor (cluster #1 Of 3), Eukaryotic Eukaryotes 1057 0.32 Binding ≤ 10μM
ADA1B-1-E Alpha-1b Adrenergic Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 966 0.32 Binding ≤ 10μM
ADA1D-1-E Alpha-1d Adrenergic Receptor (cluster #1 Of 3), Eukaryotic Eukaryotes 289 0.35 Binding ≤ 10μM
ADA2A-1-E Alpha-2a Adrenergic Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 1 0.48 Binding ≤ 10μM
ADA2A-1-E Alpha-2a Adrenergic Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 49 0.39 Binding ≤ 10μM
ADA2B-1-E Alpha-2b Adrenergic Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 7 0.44 Binding ≤ 10μM
ADA2B-1-E Alpha-2b Adrenergic Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 54 0.39 Binding ≤ 10μM
ADA2C-1-E Alpha-2c Adrenergic Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 1 0.48 Binding ≤ 10μM
ADA2C-1-E Alpha-2c Adrenergic Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 54 0.39 Binding ≤ 10μM
CAC1C-1-E Voltage-gated L-type Calcium Channel Alpha-1C Subunit (cluster #1 Of 1), Eukaryotic Eukaryotes 45 0.40 Binding ≤ 10μM
DRD1-1-E Dopamine D1 Receptor (cluster #1 Of 4), Eukaryotic Eukaryotes 2000 0.31 Binding ≤ 10μM
DRD3-1-E Dopamine D3 Receptor (cluster #1 Of 2), Eukaryotic Eukaryotes 2430 0.30 Binding ≤ 10μM
DRD4-3-E Dopamine D4 Receptor (cluster #3 Of 4), Eukaryotic Eukaryotes 2000 0.31 Binding ≤ 10μM
DRD5-1-E Dopamine D5 Receptor (cluster #1 Of 1), Eukaryotic Eukaryotes 2000 0.31 Binding ≤ 10μM
ADA2A-2-E Alpha-2a Adrenergic Receptor (cluster #2 Of 3), Eukaryotic Eukaryotes 165 0.37 Functional ≤ 10μM
ADA2B-2-E Alpha-2b Adrenergic Receptor (cluster #2 Of 3), Eukaryotic Eukaryotes 165 0.37 Functional ≤ 10μM
ADA2C-2-E Alpha-2c Adrenergic Receptor (cluster #2 Of 3), Eukaryotic Eukaryotes 165 0.37 Functional ≤ 10μM
CP2D6-1-E Cytochrome P450 2D6 (cluster #1 Of 3), Eukaryotic Eukaryotes 8 0.44 ADME/T ≤ 10μM
CP2D6-1-E Cytochrome P450 2D6 (cluster #1 Of 3), Eukaryotic Eukaryotes 80 0.38 ADME/T ≤ 10μM
DRD2-4-E Dopamine D2 Receptor (cluster #4 Of 24), Eukaryotic Eukaryotes 2000 0.31 Binding ≤ 10μM
Z104304-1-O Adrenergic Receptor Alpha-1 (cluster #1 Of 3), Other Other 360 0.35 Binding ≤ 10μM
Z50425-3-O Plasmodium Falciparum (cluster #3 Of 22), Other Other 3162 0.30 Functional ≤ 10μM
Z50587-5-O Homo Sapiens (cluster #5 Of 9), Other Other 1100 0.32 Functional ≤ 10μM
Z50597-1-O Rattus Norvegicus (cluster #1 Of 12), Other Other 505 0.34 Functional ≤ 10μM
ChEMBL Target Annotations
Uniprot Swissprot Description Affinity (nM) LE (kcal/mol/atom) Type
AA3R_HUMAN P33765 Adenosine A3 Receptor, Human 95 0.38 Binding ≤ 1μM
Z104304 Z104304 Adrenergic Receptor Alpha-1 1000 0.32 Binding ≤ 1μM
ADA1A_BOVIN P18130 Alpha-1a Adrenergic Receptor, Bovin 200 0.36 Binding ≤ 1μM
ADA1B_HUMAN P35368 Alpha-1b Adrenergic Receptor, Human 1.1 0.48 Binding ≤ 1μM
ADA1D_HUMAN P25100 Alpha-1d Adrenergic Receptor, Human 1.6 0.47 Binding ≤ 1μM
ADA1D_RAT P23944 Alpha-1d Adrenergic Receptor, Rat 52 0.39 Binding ≤ 1μM
ADA2A_HUMAN P08913 Alpha-2a Adrenergic Receptor, Human 0.4 0.51 Binding ≤ 1μM
ADA2A_RAT P22909 Alpha-2a Adrenergic Receptor, Rat 0.6 0.50 Binding ≤ 1μM
ADA2A_BOVIN Q28838 Alpha-2a Adrenergic Receptor, Bovin 49 0.39 Binding ≤ 1μM
ADA2A_MOUSE Q01338 Alpha-2a Adrenergic Receptor, Mouse 0.6 0.50 Binding ≤ 1μM
ADA2A_PIG P18871 Alpha-2a Adrenergic Receptor, Pig 4.4 0.45 Binding ≤ 1μM
ADA2B_HUMAN P18089 Alpha-2b Adrenergic Receptor, Human 0.4 0.51 Binding ≤ 1μM
ADA2B_MOUSE P30545 Alpha-2b Adrenergic Receptor, Mouse 0.6 0.50 Binding ≤ 1μM
ADA2B_BOVIN O77700 Alpha-2b Adrenergic Receptor, Bovin 49 0.39 Binding ≤ 1μM
ADA2B_RAT P19328 Alpha-2b Adrenergic Receptor, Rat 0.6 0.50 Binding ≤ 1μM
ADA2C_RAT P22086 Alpha-2c Adrenergic Receptor, Rat 0.6 0.50 Binding ≤ 1μM
ADA2C_MOUSE Q01337 Alpha-2c Adrenergic Receptor, Mouse 0.6 0.50 Binding ≤ 1μM
ADA2C_HUMAN P18825 Alpha-2c Adrenergic Receptor, Human 0.4 0.51 Binding ≤ 1μM
CAC1C_RAT P22002 Voltage-gated L-type Calcium Channel Alpha-1C Subunit, Rat 45 0.40 Binding ≤ 1μM
AA3R_HUMAN P33765 Adenosine A3 Receptor, Human 95 0.38 Binding ≤ 10μM
Z104304 Z104304 Adrenergic Receptor Alpha-1 1000 0.32 Binding ≤ 10μM
ADA1A_BOVIN P18130 Alpha-1a Adrenergic Receptor, Bovin 200 0.36 Binding ≤ 10μM
ADA1A_HUMAN P35348 Alpha-1a Adrenergic Receptor, Human 1057 0.32 Binding ≤ 10μM
ADA1B_HUMAN P35368 Alpha-1b Adrenergic Receptor, Human 1.1 0.48 Binding ≤ 10μM
ADA1D_HUMAN P25100 Alpha-1d Adrenergic Receptor, Human 1.6 0.47 Binding ≤ 10μM
ADA1D_RAT P23944 Alpha-1d Adrenergic Receptor, Rat 52 0.39 Binding ≤ 10μM
ADA2A_PIG P18871 Alpha-2a Adrenergic Receptor, Pig 4.4 0.45 Binding ≤ 10μM
ADA2A_BOVIN Q28838 Alpha-2a Adrenergic Receptor, Bovin 49 0.39 Binding ≤ 10μM
ADA2A_MOUSE Q01338 Alpha-2a Adrenergic Receptor, Mouse 0.6 0.50 Binding ≤ 10μM
ADA2A_RAT P22909 Alpha-2a Adrenergic Receptor, Rat 0.6 0.50 Binding ≤ 10μM
ADA2A_HUMAN P08913 Alpha-2a Adrenergic Receptor, Human 0.4 0.51 Binding ≤ 10μM
ADA2B_MOUSE P30545 Alpha-2b Adrenergic Receptor, Mouse 0.6 0.50 Binding ≤ 10μM
ADA2B_HUMAN P18089 Alpha-2b Adrenergic Receptor, Human 0.4 0.51 Binding ≤ 10μM
ADA2B_BOVIN O77700 Alpha-2b Adrenergic Receptor, Bovin 49 0.39 Binding ≤ 10μM
ADA2B_RAT P19328 Alpha-2b Adrenergic Receptor, Rat 0.6 0.50 Binding ≤ 10μM
ADA2C_HUMAN P18825 Alpha-2c Adrenergic Receptor, Human 0.4 0.51 Binding ≤ 10μM
ADA2C_MOUSE Q01337 Alpha-2c Adrenergic Receptor, Mouse 0.6 0.50 Binding ≤ 10μM
ADA2C_RAT P22086 Alpha-2c Adrenergic Receptor, Rat 0.6 0.50 Binding ≤ 10μM
DRD1_RAT P18901 Dopamine D1 Receptor, Rat 2000 0.31 Binding ≤ 10μM
DRD2_RAT P61169 Dopamine D2 Receptor, Rat 1125 0.32 Binding ≤ 10μM
DRD3_RAT P19020 Dopamine D3 Receptor, Rat 2000 0.31 Binding ≤ 10μM
DRD4_RAT P30729 Dopamine D4 Receptor, Rat 2000 0.31 Binding ≤ 10μM
DRD5_RAT P25115 Dopamine D5 Receptor, Rat 2000 0.31 Binding ≤ 10μM
5HT2A_RAT P14842 Serotonin 2a (5-HT2a) Receptor, Rat 1621.8101 0.31 Binding ≤ 10μM
5HT2C_MOUSE P34968 Serotonin 2c (5-HT2c) Receptor, Mouse 10000 0.27 Binding ≤ 10μM
CAC1C_RAT P22002 Voltage-gated L-type Calcium Channel Alpha-1C Subunit, Rat 45 0.40 Binding ≤ 10μM
ADA2A_RAT P22909 Alpha-2a Adrenergic Receptor, Rat 165 0.37 Functional ≤ 10μM
ADA2B_RAT P19328 Alpha-2b Adrenergic Receptor, Rat 165 0.37 Functional ≤ 10μM
ADA2C_RAT P22086 Alpha-2c Adrenergic Receptor, Rat 165 0.37 Functional ≤ 10μM
Z50587 Z50587 Homo Sapiens 1100 0.32 Functional ≤ 10μM
Z50425 Z50425 Plasmodium Falciparum 1995.26231 0.31 Functional ≤ 10μM
Z50597 Z50597 Rattus Norvegicus 505 0.34 Functional ≤ 10μM
CP2D6_HUMAN P10635 Cytochrome P450 2D6, Human 180 0.36 ADME/T ≤ 10μM

Direct Reactome Annotations (via ChEBI)

Description Species
Class C/3 (Metabotropic glutamate/pheromone receptors)
G alpha (i) signalling events

Reactome Annotations from Targets (via Uniprot)

Description Species
Adenosine P1 receptors
Adrenaline signalling through Alpha-2 adrenergic receptor
Adrenaline,noradrenaline inhibits insulin secretion
Adrenoceptors
CYP2E1 reactions
Dopamine receptors
Fatty acids
G alpha (12/13) signalling events
G alpha (i) signalling events
G alpha (q) signalling events
G alpha (z) signalling events
Miscellaneous substrates
Serotonin receptors
Xenobiotics

Analogs ( Draw Identity 99% 90% 80% 70% )