(-)-Synephrine

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	3271b31f-7593-430f-a655-fed10ca0156a
Taxonomy	Benzenoids > Phenols > 1-hydroxy-2-unsubstituted benzenoids
IUPAC Name	4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol
SMILES (Canonical)	CNCC(C1=CC=C(C=C1)O)O
SMILES (Isomeric)	CNC[C@@H](C1=CC=C(C=C1)O)O
InChI	InChI=1S/C9H13NO2/c1-10-6-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1
InChI Key	YRCWQPVGYLYSOX-VIFPVBQESA-N
Popularity	8 references in papers

Physical and Chemical Properties

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Molecular Formula	C₉H₁₃NO₂
Molecular Weight	167.20 g/mol
Exact Mass	167.094628657 g/mol
Topological Polar Surface Area (TPSA)	52.50 Å²
XlogP	-0.60
Atomic LogP (AlogP)	0.64
H-Bond Acceptor	3
H-Bond Donor	3
Rotatable Bonds	3

Synonyms

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D(-)-Synephrine

D-synephrine

(-)-Oxedrine

(-)-Sympatol

614-35-7

4-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol

Synephrine (R-isomer)

(R)-synephrine

l-Sympatol

l-Synephrine

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	+	0.9889	98.89%
Caco-2	+	0.6864	68.64%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.4885	48.85%
OATP2B1 inhibitior	-	0.8645	86.45%
OATP1B1 inhibitior	+	0.8702	87.02%
OATP1B3 inhibitior	+	0.9562	95.62%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.9827	98.27%
P-glycoprotein inhibitior	-	0.9732	97.32%
P-glycoprotein substrate	-	0.8579	85.79%
CYP3A4 substrate	-	0.7466	74.66%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5676	56.76%
CYP3A4 inhibition	-	0.8580	85.80%
CYP2C9 inhibition	-	0.9646	96.46%
CYP2C19 inhibition	-	0.9088	90.88%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9046	90.46%
CYP2C8 inhibition	-	0.9059	90.59%
CYP inhibitory promiscuity	-	0.9594	95.94%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7208	72.08%
Carcinogenicity (trinary)	Non-required	0.7329	73.29%
Eye corrosion	-	0.7730	77.30%
Eye irritation	-	0.6173	61.73%
Skin irritation	-	0.6099	60.99%
Skin corrosion	-	0.5470	54.70%
Ames mutagenesis	-	0.9300	93.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7604	76.04%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.6039	60.39%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.6503	65.03%
Mitochondrial toxicity	+	0.9875	98.75%
Nephrotoxicity	-	0.6991	69.91%
Acute Oral Toxicity (c)	II	0.7473	74.73%
Estrogen receptor binding	-	0.8683	86.83%
Androgen receptor binding	-	0.7709	77.09%
Thyroid receptor binding	-	0.7624	76.24%
Glucocorticoid receptor binding	-	0.8453	84.53%
Aromatase binding	-	0.8461	84.61%
PPAR gamma	-	0.9351	93.51%
Honey bee toxicity	-	0.8619	86.19%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6200	62.00%
Fish aquatic toxicity	-	0.9443	94.43%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293237	P54132	Bloom syndrome protein	2.8 nM	Potency	via Super-PRED
CHEMBL3397	P11712	Cytochrome P450 2C9	39810.7 nM	Potency	via CMAUP
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	158.5 nM 631 nM 158.5 nM 631 nM 158.5 nM	Potency Potency Potency Potency Potency	via CMAUP via CMAUP via CMAUP via CMAUP via Super-PRED
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	12589.3 nM	Potency	via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	707.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	95.68%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.81%	96.09%
CHEMBL2581	P07339	Cathepsin D	93.48%	98.95%
CHEMBL242	Q92731	Estrogen receptor beta	92.12%	98.35%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.09%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	85.39%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.32%	94.45%
CHEMBL4208	P20618	Proteasome component C5	82.42%	90.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.38%	89.62%

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.

Agnorhiza bolanderi

Anaxagorea crassipetala

Araujia sericifera

Arnica nevadensis

Artemisia gmelinii

Beyeria sulcata var. brevipes

Bursaria spinosa

Chloranthus tianmushanensis

Chromolaena odorata

Chromolaena pulchella

Citrus × aurantium

Citrus deliciosa