beta-Yohimbine

Details

• Internal ID: 9e844908-bb7c-4154-a9ec-734af424028e
• Taxonomy: Alkaloids and derivatives > Yohimbine alkaloids
• IUPAC Name: methyl 18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• SMILES (Canonical): COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
• SMILES (Isomeric): COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O
• 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
• InChI Key: BLGXFZZNTVWLAY-UHFFFAOYSA-N
• Popularity: 12 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₂₆N₂O₃
• Molecular Weight: 354.40 g/mol
• Exact Mass: 354.19434270 g/mol
• Topological Polar Surface Area (TPSA): 65.60 Ų
• XlogP: 2.90

Synonyms

• .beta.-Yohimbine
• Amberlite CG-400
• NSC407306
• methyl 17-hydroxy-20xi-yohimban-16-carboxylate
• CHEBI:48565
• 483-09-0
• Methyl 17-hydroxyyohimban-16-carboxylate
• Isorauhimbin
• methyl 18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16beta,17alpha,20alpha)-
• 37247-87-3
• alpha-Yohimbine;Corynanthidine;Isoyohimbine
• (-)-beta-Yohimbine; Amsonin; Amsonine; NSC 93133; beta-Yohimbin
• 3-Epirauwolscine; 3-epi-Rauwolscine
• NSC-93133
• EC-Yohimbine
• A.-Yohimbine
• NSC-407306
• COYNANTHINE
• Methyl 17-hydroxyyohimban-16-carboxylate #
• NSC19509
• Yohimbol-16.alpha.-carboxylic acid, methyl ester
• MLS000863574
• SCHEMBL564022
• Yohimban-16-alpha-carboxylic acid, 17-beta-hydroxy-, methyl ester
• Yohimban-16alpha-carboxylic acid, 17beta-hydroxy-, methyl ester
• MEGxp0_001106
• MEGxp0_002061
• CHEMBL1531132
• Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16alpha,17beta)-
• Yohimban-16.alpha.-carboxylic acid, 17.alpha.-hydroxy-, methyl ester
• ACon1_000583
• ACon1_000625
• BDBM86230
• DTXSID60859258
• BLGXFZZNTVWLAY-UHFFFAOYSA-N
• Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16-alpha,17-beta)-
• Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16.alpha.,17.alpha.)-
• HMS2269J09
• HMS3370N12
• HMS3372A16
• HMS3744C13
• methyl (1S,15R,18S,19S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
• NSC_2866
• NSC93133
• BBL008941
• STK801336
• AKOS005612952
• NCGC00015878-03
• NCGC00015878-04
• NCGC00015878-08
• CAS_146-48-5
• NCI60_001630
• NCI60_003875
• NCI60_003876
• SMR000440723
• LS-162739
• FT-0603181
• FT-0696324
• Yohimban-16.beta.-carboxylic acid, methyl ester
• L000506
• Yohimban-16.alpha.-carboxylic acid, methyl ester
• BRD-A51410489-001-01-4
• BRD-A51410489-003-02-8
• Q27121266
• B0005-144043
• Yohimban-16-carboxylic acid, methyl ester, (16.alpha.,17.beta.)-
• Yohimban-16-carboxylic acid, methyl ester, (16.beta.,17.alpha.)-
• 1,2,3,4,4a,5,7,8,13,13b,14,14a-Dodecahydro-2-hydroxy-1-(methoxycarbonyl)benz[g]indolo[2,3-a]quinolizine
• Methyl 18-hydroxy-3,13- diazapentacyclo[11.8.0.02,10.04,9.015,20]henicosa- 2(10),4,6,8-tetraene-19-carboxylate

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL229	P35348	Alpha-1a adrenergic receptor	29 nM	Ki	via Super-PRED
CHEMBL232	P35368	Alpha-1b adrenergic receptor	517 nM; 7.2 nM	Ki; Ki	via Super-PRED; via Super-PRED
CHEMBL223	P25100	Alpha-1d adrenergic receptor	1.6 nM; 3.5 nM; 253 nM	Ki; Ki; Ki	via Super-PRED; via Super-PRED; via Super-PRED
CHEMBL1867	P08913	Alpha-2a adrenergic receptor	0.42 nM	Ki	via Super-PRED
CHEMBL1942	P18089	Alpha-2b adrenergic receptor	1.16 nM	Ki	via Super-PRED
CHEMBL1916	P18825	Alpha-2c adrenergic receptor	0.5 nM; 16 nM	Ki; IC50	via Super-PRED; via Super-PRED
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	31622.8 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	39810.7 nM	Potency	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	89.1 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.57%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.19%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.93%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.05%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.87%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.92%	97.09%
CHEMBL2581	P07339	Cathepsin D	91.35%	98.95%
CHEMBL1914	P06276	Butyrylcholinesterase	90.98%	95.00%
CHEMBL2535	P11166	Glucose transporter	88.62%	98.75%
CHEMBL228	P31645	Serotonin transporter	88.51%	95.51%
CHEMBL5028	O14672	ADAM10	86.11%	97.50%
CHEMBL4040	P28482	MAP kinase ERK2	84.35%	83.82%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.97%	99.23%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	80.04%	94.08%

Plants that contains it

• Alstonia angustifolia
• Alstonia constricta
• Aspidosperma discolor
• Aspidosperma eburneum
• Aspidosperma excelsum
• Aspidosperma polyneuron
• Aspidosperma pyricollum
• Aspidosperma ramiflorum
• Catharanthus roseus
• Corynanthe pachyceras
• Rauvolfia salicifolia
• Rauvolfia serpentina
• Rauvolfia verticillata
• Rauvolfia vomitoria
• Tabernaemontana corymbosa
• Uncaria callophylla

Cross-Links

• PubChem: 2866
• NPASS: NPC313985
• ChEMBL: CHEMBL1531132
• LOTUS: LTS0253657
• wikiData: Q27121266