Showing Compound Epinephrine (FDB021889)

Record Information

Version

1.0

Creation date

2011-09-21 00:04:37 UTC

Update date

2019-11-26 03:21:00 UTC

Primary ID

FDB021889

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Epinephrine

Description

Epinephrine is a catecholamine, a sympathomimetic monoamine derived from the amino acids phenylalanine and tyrosine. It is the active sympathomimetic hormone secreted from the adrenal medulla in most species. It stimulates both the alpha- and beta- adrenergic systems, causes systemic vasoconstriction and gastrointestinal relaxation, stimulates the heart, and dilates bronchi and cerebral vessels. It is used in asthma and cardiac failure and to delay absorption of local anesthetics. Epinephrine also constricts arterioles in the skin and gut while dilating arterioles in leg muscles. It elevates the blood sugar level by increasing hydrolysis of glycogen to glucose in the liver, and at the same time begins the breakdown of lipids in adipocytes. Epinephrine has a suppressive effect on the immune system. [HMDB]

CAS Number

51-43-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(-)-(R)-Epinephrine	ChEBI
(-)-3,4-Dihydroxy-a-((methylamino)methyl)benzyl alcohol	Generator
(-)-3,4-Dihydroxy-a-[(methylamino)methyl]-benzyl alcohol	HMDB
(-)-3,4-dihydroxy-a-[(methylamino)methyl]-Benzyl alcohol	hmdb
(-)-3,4-Dihydroxy-a-[2-(methylamino)ethyl]benzyl alcohol	HMDB
(-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol	ChEBI
(-)-3,4-Dihydroxy-alpha-[(methylamino)methyl]-benzyl alcohol	HMDB
(-)-3,4-dihydroxy-alpha-[(methylamino)methyl]-Benzyl alcohol	hmdb
(-)-3,4-Dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcohol	HMDB
(-)-3,4-Dihydroxy-α-((methylamino)methyl)benzyl alcohol	Generator

Showing 1 to 10 of 108 entries

Predicted Properties

Property	Value	Source
Water Solubility	18.6 g/L	ALOGPS
logP	-0.82	ALOGPS
logP	-0.43	ChemAxon
logS	-0.99	ALOGPS
pKa (Strongest Acidic)	9.69	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	72.72 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.23 m³·mol⁻¹	ChemAxon
Polarizability	19.04 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C9H13NO3

IUPAC name

4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol

InChI Identifier

InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3/t9-/m0/s1

InChI Key

UCTWMZQNUQWSLP-VIFPVBQESA-N

Isomeric SMILES

CNC[C@H](O)C1=CC(O)=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 catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Monocyclic benzene moiety
1,2-aminoalcohol
Secondary alcohol
Secondary amine
Secondary aliphatic amine
Aromatic alcohol
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Amine
Organopnictogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

adrenaline (CHEBI:28918 )
Biogenic amines (C00788 )
Adrenalines (C00788 )

Ontology

Endogenous

Biological:

Microbe:

Escherichia:

Escherichia coli

Bacillus

Biological location:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Epinephrine, non-derivatized, GC-MS Spectrum	splash10-014i-0900000000-5ca773e378035e522e65	Spectrum
GC-MS	Epinephrine, non-derivatized, GC-MS Spectrum	splash10-014i-0900000000-5ca773e378035e522e65	Spectrum
Predicted GC-MS	Epinephrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0006-9600000000-584d6e44f2be8cb4eeb1	Spectrum
Predicted GC-MS	Epinephrine, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00si-7639000000-5bde61303f7506ecea58	Spectrum
Predicted GC-MS	Epinephrine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_3_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_3_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TMS_3_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TBDMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Epinephrine, TBDMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-014i-0900000000-7718bec49c1a109083e5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4i-4900000000-ec5581e838e2a4a66139	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-004i-9200000000-4572448ba3dadff2d2a6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-001i-0900000000-9da12d9c8551de2507be	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-03di-0900000000-12dd42d00be1feb2ea6f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-0900000000-57c9bc614d9bbbfeed6b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-00dj-0900000000-375b0df9797eb0a3db5f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-0fdk-1900000000-04c230e802b08770ccd4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-014i-0900000000-b707acd2982b875d2b8a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-014i-0900000000-f3590054822872902032	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0a4i-1900000000-7d7916641e9f2b8c2a1d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0adi-8900000000-5bbc248c0ddc66e4fe40	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004i-9300000000-af8ce8ce2cdd535404e9	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0159-0900000000-f2fafb87963f9f1c6960	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0uxr-2900000000-b54ca44315664cba912a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0udi-4900000000-881b25fed45874c66e13	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0ugi-9500000000-1fadd0dd0beb4816b39d	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-004j-9000000000-61011b8f179c08d62b62	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-03di-0900000000-32c82b77af021d75c50c	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0159-0900000000-92937e3a48622f40baed	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014r-0900000000-b00275b1e8611c273f02	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0k9l-7900000000-065763dae156017492c9	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0900000000-45c50917c3f404f38e71	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01q9-1900000000-713b357534dc0f81ae97	2017-07-26	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-5900000000-c6b1d16c9e7e36805557	2017-07-26	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

28918

Phenol-Explorer ID

Not Available

DrugBank ID

DB00668

HMDB ID

HMDB00068

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

35997

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

Epinephrine

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

Avocado	Expected but not quantified	Not Available	F. W. Knapp. Some Characteristics of Eggplant and Avocado Poiyphenolases. J. Food Science. 30(6), 930-936, 1965
Eggplant	Expected but not quantified	Not Available	F. W. Knapp. Some Characteristics of Eggplant and Avocado Poiyphenolases. J. Food Science. 30(6), 930-936, 1965
Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB

Showing 1 to 10 of 31 entries

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Alpha-2A adrenergic receptor	ADRA2A	P08913
Alpha-2B adrenergic receptor	ADRA2B	P18089
Beta-1 adrenergic receptor	ADRB1	P08588
Beta-2 adrenergic receptor	ADRB2	P07550
Phenylalanine-4-hydroxylase	PAH	P00439