Showing Compound (R)-Synephrine (FDB000709)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:41 UTC

Update date

2019-11-26 02:55:16 UTC

Primary ID

FDB000709

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(R)-Synephrine

Description

(R)-Synephrine belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position (R)-Synephrine is a very strong basic compound (based on its pKa) (R)-Synephrine has been detected, but not quantified in, several different foods, such as citrus, fruits, lemons, mandarin orange (clementine, tangerine), and sweet oranges. This could make (R)-synephrine a potential biomarker for the consumption of these foods.

CAS Number

94-07-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(+)-[(Methylamino)methyl]-benzenemethano	HMDB
(+)-P-Synephrine	HMDB
(+)-Synephrine	HMDB
(+/-)-synephrine	ChEBI
1-(4-Hydroxyphenyl)-2-(methylamino)ethanol	ChEBI
1-(4-Hydroxyphenyl)-2-methylaminoethanol	ChEBI
4-Hydroxy-a-[(methylamino)methyl]benzenemethanol	Generator
4-Hydroxy-alpha-[(methylamino)methyl]benzenemethanol	ChEBI
4-Hydroxy-α-[(methylamino)methyl]benzenemethanol	Generator
b-Methylamino-a-(4-hydroxyphenyl)ethyl alcohol	Generator

Showing 1 to 10 of 25 entries

Predicted Properties

Property	Value	Source
Water Solubility	46.9 g/L	ALOGPS
logP	-0.73	ALOGPS
logP	0.74	ChemAxon
logS	-0.59	ALOGPS
pKa (Strongest Acidic)	9.46	ChemAxon
pKa (Strongest Basic)	8.13	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	61.72 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	48.17 m³·mol⁻¹	ChemAxon
Polarizability	19.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H13NO3

IUPAC name

4-[(R)-hydroxy[(methylamino)methoxy]methyl]phenol

InChI Identifier

InChI=1S/C9H13NO3/c1-10-6-13-9(12)7-2-4-8(11)5-3-7/h2-5,9-12H,6H2,1H3/t9-/m1/s1

InChI Key

GBBBJHCSNNEWLH-SECBINFHSA-N

Isomeric SMILES

CNCO[C@@H](O)C1=CC=C(O)C=C1

Average Molecular Weight

183.2044

Monoisotopic Molecular Weight

183.089543287

Classification

Description

Belongs to the class of organic compounds known as 1-hydroxy-2-unsubstituted benzenoids. These are phenols that are unsubstituted at the 2-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-2-unsubstituted benzenoids

Direct Parent

1-hydroxy-2-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Hemiaminal
Hemiacetal
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic alcohol
Organooxygen compound
Organonitrogen compound
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	-0.45	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 64.65%; H 7.84%; N 8.38%; O 19.14%	DFC
Melting Point	Mp 162-164° dec.	DFC
Optical Rotation	[a]25D -55.6 (c, 0.5 in M HCl)	DFC

Showing 1 to 10 of 14 entries

Spectra

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

119

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04826

CRC / DFC (Dictionary of Food Compounds) ID

BZZ90-X:BFT10-L

EAFUS ID

Not Available

Dr. Duke ID

SYNEPHRINE

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Synephrine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cardiovascular	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
hypertensive			DUKE
oxytocic	36063	A drug that stimulates contraction of the myometrium. Oxytocics are used to induce labour, obstetric at term, to prevent or control postpartum or postabortion haemorrhage, and to assess foetal status in high risk pregnancies. They may also be used alone or with other drugs to induce abortions (abortifacients).	DUKE
vasoconstrictor	50514	Drug used to cause constriction of the blood vessels.	DUKE