Yohimbine

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	d4f3ade2-6c78-4816-a9c1-c128b7afedb2
Taxonomy	Alkaloids and derivatives > Yohimbine alkaloids
IUPAC Name	methyl (1S,15R,18S,19R,20S)-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)[C@H]1[C@H](CC[C@@H]2[C@@H]1C[C@H]3C4=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/t12-,15-,17-,18-,19+/m0/s1
InChI Key	BLGXFZZNTVWLAY-SCYLSFHTSA-N
Popularity	10,937 references in papers

Physical and Chemical Properties

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Molecular Formula	C₂₁H₂₆N₂O₃
Molecular Weight	354.40 g/mol
Exact Mass	354.19434270 g/mol
Topological Polar Surface Area (TPSA)	65.60 Å²
XlogP	2.90
Atomic LogP (AlogP)	2.65
H-Bond Acceptor	4
H-Bond Donor	2
Rotatable Bonds	1

Synonyms

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Yohimbin

146-48-5

Quebrachin

Quebrachine

Corynine

APHRODINE

Yohimbic acid methyl ester

Aphrosol

(+)-Yohimbine

Yohimex

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9856	98.56%
Caco-2	+	0.9312	93.12%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	-	0.9000	90.00%
Subcellular localzation	Mitochondria	0.7506	75.06%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9368	93.68%
OATP1B3 inhibitior	+	0.9479	94.79%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.9071	90.71%
P-glycoprotein inhibitior	-	0.7032	70.32%
P-glycoprotein substrate	+	0.9344	93.44%
CYP3A4 substrate	+	0.7976	79.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4913	49.13%
CYP3A4 inhibition	-	0.8333	83.33%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9094	90.94%
CYP2D6 inhibition	+	0.8931	89.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.5764	57.64%
CYP inhibitory promiscuity	-	0.8682	86.82%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6191	61.91%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9861	98.61%
Skin irritation	-	0.7617	76.17%
Skin corrosion	-	0.9523	95.23%
Ames mutagenesis	-	0.6378	63.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.8763	87.63%
Micronuclear	+	0.6100	61.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.9054	90.54%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.9778	97.78%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	+	0.7565	75.65%
Acute Oral Toxicity (c)	II	0.4961	49.61%
Estrogen receptor binding	+	0.6268	62.68%
Androgen receptor binding	+	0.7850	78.50%
Thyroid receptor binding	-	0.5760	57.60%
Glucocorticoid receptor binding	-	0.6381	63.81%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	-	0.8545	85.45%
Honey bee toxicity	-	0.8352	83.52%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	-	0.5922	59.22%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL256	P0DMS8	Adenosine A3 receptor	95 nM	IC50	PMID: 16250647
CHEMBL229	P35348	Alpha-1a adrenergic receptor	29 nM 1057 nM	Ki Ki	via Super-PRED PMID: 7562902
CHEMBL232	P35368	Alpha-1b adrenergic receptor	7.2 nM 1.1 nM 517 nM 7.2 nM	Ki Ki Ki Ki	PMID: 7658428 PMID: 7658428 via Super-PRED via Super-PRED
CHEMBL223	P25100	Alpha-1d adrenergic receptor	1013 nM 253 nM 1.6 nM 3.5 nM	IC50 Ki Ki Ki	via CMAUP via Super-PRED via Super-PRED via Super-PRED
CHEMBL1867	P08913	Alpha-2a adrenergic receptor	8.4 nM 6.151 nM 0.42 nM	IC50 IC50 Ki	PMID: 23403082 via CMAUP via Super-PRED
CHEMBL1942	P18089	Alpha-2b adrenergic receptor	1.16 nM 17 nM	Ki IC50	via Super-PRED via CMAUP
CHEMBL1916	P18825	Alpha-2c adrenergic receptor	16 nM 0.5 nM 36 nM	IC50 Ki IC50	via Super-PRED via Super-PRED via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	8.4 nM 2031.7 nM	IC50 IC50	PMID: 15481972 via CMAUP
CHEMBL1781	P11387	DNA topoisomerase I	30000 nM	IC50	PMID: 15974606
CHEMBL217	P14416	Dopamine D2 receptor	2060 nM	IC50	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	89.1 nM	Potency	via Super-PRED
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	14689.2 nM	Potency	via CMAUP
CHEMBL1833	P41595	Serotonin 2b (5-HT2b) receptor	74 nM	IC50	via CMAUP
CHEMBL3371	P50406	Serotonin 6 (5-HT6) receptor	1689 nM	IC50	via CMAUP

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

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Alstonia angustifolia

Alstonia macrophylla

Amsonia elliptica

Aspidosperma discolor

Aspidosperma eburneum

Aspidosperma excelsum

Aspidosperma polyneuron

Aspidosperma pyricollum