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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (11) Show 11 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:14:29 UTC

HMDB ID

HMDB0000068

Secondary Accession Numbers

HMDB0000615
HMDB00068
HMDB00615

Metabolite Identification

Common 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.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 18-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAR-20         0                                  
HETATM    1  C   UNK     0      -2.565  -1.362   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.231  -2.132   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.103  -1.362   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.103   0.178   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.231   0.948   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.565   0.178   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.898  -2.132   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -3.898   0.948   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.436   0.948   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.770   0.178   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       1.436   2.488   0.000  0.00  0.00           O+0
HETATM   12  N   UNK     0       4.104   0.948   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       5.437   0.178   0.000  0.00  0.00           C+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5    8                                                  
CONECT    7    1                                                            
CONECT    8    6                                                            
CONECT    9    4   10   11                                                  
CONECT   10    9   12                                                       
CONECT   11    9                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-(R)-Epinephrine	ChEBI
(-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol	ChEBI
(-)-Adrenaline	ChEBI
(R)-(-)-Adrenaline	ChEBI
(R)-(-)-Adnephrine	ChEBI
(R)-(-)-Epinephrine	ChEBI
(R)-(-)-Epirenamine	ChEBI
4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol	ChEBI
Adrenalin	ChEBI
Adrenaline	ChEBI
Epinefrina	ChEBI
Epinephrin	ChEBI
Epinephrinum	ChEBI
Epipen	ChEBI
Epipen JR	ChEBI
L-Adrenaline	ChEBI
Levoepinephrine	ChEBI
Primatene	ChEBI
Auvi-Q	Kegg
(-)-3,4-Dihydroxy-a-((methylamino)methyl)benzyl alcohol	Generator
(-)-3,4-Dihydroxy-α-((methylamino)methyl)benzyl alcohol	Generator
(-)-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	HMDB
(-)-3,4-Dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcohol	HMDB
(-)-Epinephrine	HMDB
(R)-4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol	HMDB
(R)-Adrenaline	HMDB
(R)-Epinephrine	HMDB
Adnephrine	HMDB
Adrenal	HMDB
Adrenine	HMDB
Adrin	HMDB
Ana-kit	HMDB
Bosmin	HMDB
Bronkaid mist	HMDB
Chelafrin	HMDB
Epifrin	HMDB
Epiglaufrin	HMDB
Epinephran	HMDB
Epirenan	HMDB
Eppy	HMDB
Exadrin	HMDB
Glauposine	HMDB
Hemisine	HMDB
Hemostasin	HMDB
Hemostatin	HMDB
Hypernephrin	HMDB
Isoptoepinal	HMDB
L-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol	HMDB
L-Epinephrine	HMDB
L-Epirenamine	HMDB
L-Methylaminoethanolcatechol	HMDB
Levorenen	HMDB
Levorenin	HMDB
Levorenine	HMDB
Levoreninum	HMDB
Lyodrin	HMDB
Methylarterenol	HMDB
Mucidrina	HMDB
Nephridine	HMDB
Nieraline	HMDB
Paranephrin	HMDB
Primatene mist	HMDB
R-(-)-Epinephrine	HMDB
Renaglandin	HMDB
Renaleptine	HMDB
Renalina	HMDB
Renoform	HMDB
Renostypticin	HMDB
Renostyptin	HMDB
Scurenaline	HMDB
Simplene	HMDB
Styptirenal	HMDB
Supracapsulin	HMDB
Supranephrane	HMDB
Suprarenaline	HMDB
Suprarenin	HMDB
Surrenine	HMDB
Sus-phrine	HMDB
Takamina	HMDB
Vasoconstrictine	HMDB
Vasotonin	HMDB
4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol	HMDB
Epinephrine bitartrate	HMDB
Epinephrine hydrogen tartrate	HMDB
Lyophrin	HMDB
Adrenaline bitartrate	HMDB
Adrenaline hydrochloride	HMDB
Epinephrine acetate	HMDB
Allergan brand OF adrenaline hydrochloride	HMDB
Epitrate	HMDB
Acetate, epinephrine	HMDB
Adrenaline acid tartrate	HMDB
Epinephrine hydrochloride	HMDB
Medihaler-epi	HMDB

Chemical Formula

C₉H₁₃NO₃

Average Molecular Weight

183.2044

Monoisotopic Molecular Weight

183.089543287

IUPAC Name

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

Traditional Name

epinephrine

CAS Registry Number

51-43-4

SMILES

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

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

Chemical Taxonomy

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

Physiological effect

Health effect

Circulatory system disorder

Blood and lymphatic system disorder

Hemorrhagic disorder

Subarachnoid hemorrhage (HMDB: HMDB0000068)

Nervous system disorder

Central nervous system disorder

Psychiatric disorder

Schizophrenia (HMDB: HMDB0000068)

Traumatic brain injury (HMDB: HMDB0000068)

Endocrine system disorder

Adrenal disorder

Pheochromocytoma (HMDB: HMDB0000068)
Addison's Disease (HMDB: HMDB0000068)

Adipose tissue (HMDB: HMDB0000068)
Adipose tissue (HMDB: HMDB0000068)

Nervous tissue

Nervous tissue (HMDB: HMDB0000068)

Epithelium

Epidermis (HMDB: HMDB0000068)

Eye Lens (HMDB: HMDB0000068)

Muscle tissue

Skeletal muscle (HMDB: HMDB0000068)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7704967)
Cerebrospinal Fluid (CSF) (PMID: 12834252)
Cerebrospinal fluid (HMDB: HMDB0000068)

Cell

Fibroblast

Fibroblast (HMDB: HMDB0000068)

Hematocyte

Platelet (HMDB: HMDB0000068)

Tissue substructure

Muscle (HMDB: HMDB0000068)

Organ substructure

Organ

Gland

Adrenal Gland (HMDB: HMDB0000068)
Adrenal Gland (HMDB: HMDB0000068)

Excreta

Biofluid or Excreta

Urine (PMID: 10349032)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0000068)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)

Endogenous

Endogenous (HMDB: HMDB0000068)

Microbe

Escherichia coli (HMDB: HMDB0000068)
Bacillus (HMDB: HMDB0000068)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tyrosine Metabolism (PathBank: SMP0087328)
Catecholamine Biosynthesis (HMDB: HMDB0000068)
Catecholamine Biosynthesis (PathBank: SMP0063606)

Disease pathway

Tyrosinemia, Transient, of the Newborn (PathBank: SMP0120779)
Aromatic L-Aminoacid Decarboxylase Deficiency (PathBank: SMP0120457)
Tyrosine Hydroxylase Deficiency (PathBank: SMP0120562)
Hawkinsinuria (PathBank: SMP0120711)
Tyrosinemia Type I (PathBank: SMP0120729)
Alkaptonuria (PathBank: SMP0120453)
Dopamine beta-Hydroxylase Deficiency (PathBank: SMP0120563)
Monoamine Oxidase-A Deficiency (MAO-A) (PathBank: SMP0120817)

Drug action pathway

Disulfiram Action Pathway (HMDB: HMDB0000068)
Disulfiram Action Pathway (PathBank: SMP0000429)
Epinephrine Action Pathway (PathBank: SMP0000661)

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0000068)

Biomarker

Addison's Disease (MarkerDB: MDB00000035)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	211.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.18 mg/mL	Not Available
LogP	-1.37	HANSCH,C & LEO,AJ (1985)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	144.833	30932474
[M-H]-	MetCCS_train_neg	137.866	30932474
[M+H]+	Astarita_pos	132.7	30932474
[M-H]-	Not Available	140.9	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000283

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	145.069	31661259
DarkChem	[M-H]-	141.448	31661259
AllCCS	[M+H]+	141.613	32859911
AllCCS	[M-H]-	140.618	32859911
DeepCCS	[M+H]+	144.244	30932474
DeepCCS	[M-H]-	141.848	30932474
DeepCCS	[M-2H]-	175.787	30932474
DeepCCS	[M+Na]+	150.451	30932474
AllCCS	[M+H]+	141.6	32859911
AllCCS	[M+H-H2O]+	137.5	32859911
AllCCS	[M+NH4]+	145.5	32859911
AllCCS	[M+Na]+	146.6	32859911
AllCCS	[M-H]-	140.6	32859911
AllCCS	[M+Na-2H]-	141.6	32859911
AllCCS	[M+HCOO]-	142.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.24 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8772 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.69 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	284.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	409.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	256.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	67.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	39.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	274.3 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	224.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	822.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	561.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	39.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	693.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	166.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	175.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	705.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	522.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	291.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epinephrine	CNC[C@H](O)C1=CC(O)=C(O)C=C1	3056.2	Standard polar	33892256
Epinephrine	CNC[C@H](O)C1=CC(O)=C(O)C=C1	1820.5	Standard non polar	33892256
Epinephrine	CNC[C@H](O)C1=CC(O)=C(O)C=C1	1827.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epinephrine,1TMS,isomer #1	CNC[C@H](O[Si](C)(C)C)C1=CC=C(O)C(O)=C1	1870.7	Semi standard non polar	33892256
Epinephrine,1TMS,isomer #2	CNC[C@H](O)C1=CC=C(O)C(O[Si](C)(C)C)=C1	1814.9	Semi standard non polar	33892256
Epinephrine,1TMS,isomer #3	CNC[C@H](O)C1=CC=C(O[Si](C)(C)C)C(O)=C1	1826.5	Semi standard non polar	33892256
Epinephrine,1TMS,isomer #4	CN(C[C@H](O)C1=CC=C(O)C(O)=C1)[Si](C)(C)C	1994.8	Semi standard non polar	33892256
Epinephrine,2TMS,isomer #1	CNC[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1	1804.8	Semi standard non polar	33892256
Epinephrine,2TMS,isomer #2	CNC[C@H](O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1	1804.1	Semi standard non polar	33892256
Epinephrine,2TMS,isomer #3	CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O)C(O)=C1)[Si](C)(C)C	1990.1	Semi standard non polar	33892256
Epinephrine,2TMS,isomer #4	CNC[C@H](O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1859.5	Semi standard non polar	33892256
Epinephrine,2TMS,isomer #5	CN(C[C@H](O)C1=CC=C(O)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	1959.0	Semi standard non polar	33892256
Epinephrine,2TMS,isomer #6	CN(C[C@H](O)C1=CC=C(O[Si](C)(C)C)C(O)=C1)[Si](C)(C)C	1985.3	Semi standard non polar	33892256
Epinephrine,3TMS,isomer #1	CNC[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1	1856.3	Semi standard non polar	33892256
Epinephrine,3TMS,isomer #2	CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O)=C1)[Si](C)(C)C	1955.3	Semi standard non polar	33892256
Epinephrine,3TMS,isomer #3	CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	1949.4	Semi standard non polar	33892256
Epinephrine,3TMS,isomer #4	CN(C[C@H](O)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2004.7	Semi standard non polar	33892256
Epinephrine,4TMS,isomer #1	CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	2023.0	Semi standard non polar	33892256
Epinephrine,4TMS,isomer #1	CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	1994.6	Standard non polar	33892256
Epinephrine,4TMS,isomer #1	CN(C[C@H](O[Si](C)(C)C)C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[Si](C)(C)C	1930.9	Standard polar	33892256
Epinephrine,1TBDMS,isomer #1	CNC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C1	2093.7	Semi standard non polar	33892256
Epinephrine,1TBDMS,isomer #2	CNC[C@H](O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2075.5	Semi standard non polar	33892256
Epinephrine,1TBDMS,isomer #3	CNC[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2090.6	Semi standard non polar	33892256
Epinephrine,1TBDMS,isomer #4	CN(C[C@H](O)C1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C	2230.5	Semi standard non polar	33892256
Epinephrine,2TBDMS,isomer #1	CNC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1	2288.3	Semi standard non polar	33892256
Epinephrine,2TBDMS,isomer #2	CNC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1	2294.3	Semi standard non polar	33892256
Epinephrine,2TBDMS,isomer #3	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O)=C1)[Si](C)(C)C(C)(C)C	2484.2	Semi standard non polar	33892256
Epinephrine,2TBDMS,isomer #4	CNC[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2361.2	Semi standard non polar	33892256
Epinephrine,2TBDMS,isomer #5	CN(C[C@H](O)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2451.6	Semi standard non polar	33892256
Epinephrine,2TBDMS,isomer #6	CN(C[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[Si](C)(C)C(C)(C)C	2489.7	Semi standard non polar	33892256
Epinephrine,3TBDMS,isomer #1	CNC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1	2520.8	Semi standard non polar	33892256
Epinephrine,3TBDMS,isomer #2	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[Si](C)(C)C(C)(C)C	2698.9	Semi standard non polar	33892256
Epinephrine,3TBDMS,isomer #3	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2690.3	Semi standard non polar	33892256
Epinephrine,3TBDMS,isomer #4	CN(C[C@H](O)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2724.8	Semi standard non polar	33892256
Epinephrine,4TBDMS,isomer #1	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2938.8	Semi standard non polar	33892256
Epinephrine,4TBDMS,isomer #1	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2768.0	Standard non polar	33892256
Epinephrine,4TBDMS,isomer #1	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2420.0	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Urine

Tissue Locations

Adipose Tissue
Adrenal Cortex
Adrenal Gland
Adrenal Medulla
Bladder
Epidermis
Eye Lens
Fibroblasts
Intestine
Kidney
Liver
Neuron
Ovary
Pancreas
Placenta
Platelet
Skeletal Muscle
Testis

Pathways

Name	SMPDB/PathBank	KEGG
Tyrosine metabolism	Not Available
Tyrosine metabolism	Not Available
Aromatic L-Aminoacid Decarboxylase Deficiency		Not Available
Tyrosine hydroxylase deficiency		Not Available
Alkaptonuria		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.0003 +/- 0.00003 uM	Adult (>18 years old)	Male	Normal	7704967	details
Blood	Detected and Quantified	0.00072 (0.00049-0.0013) uM	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Blood	Detected and Quantified	0.00164 +/- 0.00012 uM	Adult (>18 years old)	Both	Normal	12121816	details
Blood	Detected and Quantified	0.00029 +/- 0.000021 uM	Adult (>18 years old)	Female	Normal	7704967	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.034 (0.0063-0.062) uM	Adult (>18 years old)	Female	Normal	12834252	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.00024 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.0 (0.0-0.00022) uM	Adult (>18 years old)	Both	Normal	15123562	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000235 +/- 0.00003277 uM	Not Specified	Not Specified	Normal	6744640	details
Urine	Detected and Quantified	0.002 +/- 0.00099 umol/mmol creatinine	Children (1-13 years old)	Both	Normal	10349032	details
Urine	Detected and Quantified	0.0052 (0.00043-0.0099) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	9931050	details
Urine	Detected and Quantified	0.0021 (0.00098-0.0052) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0.0057 +/- 0.00092 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	3122251	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25729574	details
Urine	Detected and Quantified	0.016 (0.001-0.089) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	21670092	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.00014 +/- 0.000036 uM	Adult (>18 years old)	Male	Addison's disease	7704967	details
Blood	Detected and Quantified	0.001 +/- 0.00036 uM	Adult (>18 years old)	Both	Subarachnoid haemorrhage	12121816	details
Blood	Detected and Quantified	0.00029 (0.00005-0.00054) uM	Adult (>18 years old)	Both	Pheochromocytoma	9626157	details
Blood	Detected and Quantified	0.0025 (0.0002-0.0048) uM	Adult (>18 years old)	Both	Pheochromocytoma	9626157	details
Blood	Detected and Quantified	0.00241 +/- 0.00057 uM	Adult (>18 years old)	Both	Head trauma	12121816	details
Blood	Detected and Quantified	0.000077 +/- 0.000025 uM	Adult (>18 years old)	Female	Addison's disease	7704967	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000453 +/- 0.00004916 uM	Adult (>18 years old)	Not Specified	borderline hypertensives	6744640	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000147 +/- 0.000109 uM	Adult (>18 years old)	Not Specified	Cerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000109 uM	Adult (>18 years old)	Not Specified	Cerebral infarction, headache, paresthesia and ununconfirmed suspicion of leucemic infaction or brain metastasis with normal CSF value but renal insufficiency	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000251 uM	Adult (>18 years old)	Not Specified	Haemorrhagic infarction	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000300 uM	Adult (>18 years old)	Not Specified	Bacterial meningitis	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000481 uM	Adult (>18 years old)	Not Specified	Leucemic meningiosa	4031843	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.000153 uM	Adult (>18 years old)	Not Specified	Encephalitis	4031843	details
Urine	Detected and Quantified	0.011 +/- 0.0022 umol/mmol creatinine	Adult (>18 years old)	Both	Exercise	3122251	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Schizophrenia	25729574	details

Associated Disorders and Diseases

Disease References

Addison's Disease
Bornstein SR, Breidert M, Ehrhart-Bornstein M, Kloos B, Scherbaum WA: Plasma catecholamines in patients with Addison's disease. Clin Endocrinol (Oxf). 1995 Feb;42(2):215-8. [PubMed:7704967 ]
Subarachnoid hemorrhage
Lambert G, Naredi S, Eden E, Rydenhag B, Friberg P: Monoamine metabolism and sympathetic nervous activation following subarachnoid haemorrhage: influence of gender and hydrocephalus. Brain Res Bull. 2002 May;58(1):77-82. [PubMed:12121816 ]
Pheochromocytoma
Eisenhofer G, Keiser H, Friberg P, Mezey E, Huynh TT, Hiremagalur B, Ellingson T, Duddempudi S, Eijsbouts A, Lenders JW: Plasma metanephrines are markers of pheochromocytoma produced by catechol-O-methyltransferase within tumors. J Clin Endocrinol Metab. 1998 Jun;83(6):2175-85. [PubMed:9626157 ]
Head injury
Lambert G, Naredi S, Eden E, Rydenhag B, Friberg P: Monoamine metabolism and sympathetic nervous activation following subarachnoid haemorrhage: influence of gender and hydrocephalus. Brain Res Bull. 2002 May;58(1):77-82. [PubMed:12121816 ]
Cerebral infarction
Ratge D, Bauersfeld W, Wisser H: The relationship of free and conjugated catecholamines in plasma and cerebrospinal fluid in cerebral and meningeal disease. J Neural Transm. 1985;62(3-4):267-84. [PubMed:4031843 ]
Bacterial meningitis
Ratge D, Bauersfeld W, Wisser H: The relationship of free and conjugated catecholamines in plasma and cerebrospinal fluid in cerebral and meningeal disease. J Neural Transm. 1985;62(3-4):267-84. [PubMed:4031843 ]
Encephalitis
Ratge D, Bauersfeld W, Wisser H: The relationship of free and conjugated catecholamines in plasma and cerebrospinal fluid in cerebral and meningeal disease. J Neural Transm. 1985;62(3-4):267-84. [PubMed:4031843 ]
Schizophrenia
Fryar-Williams S, Strobel JE: Biomarkers of a five-domain translational substrate for schizophrenia and schizoaffective psychosis. Biomark Res. 2015 Feb 6;3:3. doi: 10.1186/s40364-015-0028-1. eCollection 2015. [PubMed:25729574 ]

Associated OMIM IDs

240200 (Addison's Disease)
105800 (Subarachnoid hemorrhage)
171300 (Pheochromocytoma)
181500 (Schizophrenia)

External Links

DrugBank ID

DB00668

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28918

Food Biomarker Ontology

Not Available

VMH ID

ADRNL

MarkerDB ID

MDB00000035

Good Scents ID

Not Available

References

Synthesis Reference

Singer, Robert A.; Carreira, Erick M. An in situ procedure for catalytic, enantioselective acetate aldol addition. Application to the synthesis of (R)-(-)-epinephrine. Tetrahedron Letters (1997), 38(6), 927-930.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Blagitko N, Schulz U, Schinzel AA, Ropers HH, Kalscheuer VM: gamma2-COP, a novel imprinted gene on chromosome 7q32, defines a new imprinting cluster in the human genome. Hum Mol Genet. 1999 Dec;8(13):2387-96. [PubMed:10556286 ]
Goldstein DS, Eisenhofer G, Kopin IJ: Sources and significance of plasma levels of catechols and their metabolites in humans. J Pharmacol Exp Ther. 2003 Jun;305(3):800-11. Epub 2003 Mar 20. [PubMed:12649306 ]
Kurtis JD, Friedman JF, Leenstra T, Langdon GC, Wu HW, Manalo DL, Su L, Jiz M, Jarilla B, Pablo AO, McGarvey ST, Olveda RM, Acosta LP: Pubertal development predicts resistance to infection and reinfection with Schistosoma japonicum. Clin Infect Dis. 2006 Jun 15;42(12):1692-8. Epub 2006 May 12. [PubMed:16705573 ]
Eisenhofer G, Keiser H, Friberg P, Mezey E, Huynh TT, Hiremagalur B, Ellingson T, Duddempudi S, Eijsbouts A, Lenders JW: Plasma metanephrines are markers of pheochromocytoma produced by catechol-O-methyltransferase within tumors. J Clin Endocrinol Metab. 1998 Jun;83(6):2175-85. [PubMed:9626157 ]
Igdoura SA, Gafuik C, Mertineit C, Saberi F, Pshezhetsky AV, Potier M, Trasler JM, Gravel RA: Cloning of the cDNA and gene encoding mouse lysosomal sialidase and correction of sialidase deficiency in human sialidosis and mouse SM/J fibroblasts. Hum Mol Genet. 1998 Jan;7(1):115-21. [PubMed:9384611 ]
Kaufer D, Ogle WO, Pincus ZS, Clark KL, Nicholas AC, Dinkel KM, Dumas TC, Ferguson D, Lee AL, Winters MA, Sapolsky RM: Restructuring the neuronal stress response with anti-glucocorticoid gene delivery. Nat Neurosci. 2004 Sep;7(9):947-53. Epub 2004 Aug 8. [PubMed:15300253 ]
Yasuda G, Umemura S, Ishii M: Characterization of bunazosin-sensitive alpha1-adrenoceptors in human renal medulla. J Cardiovasc Pharmacol. 1997 Aug;30(2):163-8. [PubMed:9269942 ]
Gear AR, Camerini D: Platelet chemokines and chemokine receptors: linking hemostasis, inflammation, and host defense. Microcirculation. 2003 Jun;10(3-4):335-50. [PubMed:12851650 ]
Wilson BS, Petrella E, Lowe SR, Lien K, Mackensen DG, Gridley DS, Stickney DR: Radiolocalization of human small cell lung cancer and antigen-positive normal tissues using monoclonal antibody LS2D617. Cancer Res. 1990 May 15;50(10):3124-30. [PubMed:2159374 ]
Blakely RD, Apparsundaram S: Structural diversity in the catecholamine transporter gene family: molecular cloning and characterization of an L-epinephrine transporter from bullfrog sympathetic ganglia. Adv Pharmacol. 1998;42:206-10. [PubMed:9327880 ]
Belloni AS, Albertin G, Forneris ML, Nussdorfer GG: Proadrenomedullin-derived peptides as autocrine-paracrine regulators of cell growth. Histol Histopathol. 2001 Oct;16(4):1263-74. [PubMed:11642745 ]
Contreras LN, Arregger AL, Persi GG, Gonzalez NS, Cardoso EM: A new less-invasive and more informative low-dose ACTH test: salivary steroids in response to intramuscular corticotrophin. Clin Endocrinol (Oxf). 2004 Dec;61(6):675-82. [PubMed:15579180 ]
Kushnir MM, Rockwood AL, Roberts WL, Pattison EG, Owen WE, Bunker AM, Meikle AW: Development and performance evaluation of a tandem mass spectrometry assay for 4 adrenal steroids. Clin Chem. 2006 Aug;52(8):1559-67. Epub 2006 Jun 15. [PubMed:16777916 ]
Krohn K, Uibo R, Aavik E, Peterson P, Savilahti K: Identification by molecular cloning of an autoantigen associated with Addison's disease as steroid 17 alpha-hydroxylase. Lancet. 1992 Mar 28;339(8796):770-3. [PubMed:1347802 ]
Bornstein SR, Breidert M, Ehrhart-Bornstein M, Kloos B, Scherbaum WA: Plasma catecholamines in patients with Addison's disease. Clin Endocrinol (Oxf). 1995 Feb;42(2):215-8. [PubMed:7704967 ]
Engelborghs S, Marescau B, De Deyn PP: Amino acids and biogenic amines in cerebrospinal fluid of patients with Parkinson's disease. Neurochem Res. 2003 Aug;28(8):1145-50. [PubMed:12834252 ]
Hiroi N, Yanagisawa R, Yoshida-Hiroi M, Endo T, Kawase T, Tsuchida Y, Toyama K, Shibuya K, Nakata K, Yoshino G: Retroperitoneal hemorrhage due to bilateral adrenal metastases from lung adenocarcinoma. J Endocrinol Invest. 2006 Jun;29(6):551-4. [PubMed:16840834 ]
Kennedy B, Bigby TD, Ziegler MG: Nonadrenal epinephrine-forming enzymes in humans. Characteristics, distribution, regulation, and relationship to epinephrine levels. J Clin Invest. 1995 Jun;95(6):2896-902. [PubMed:7769131 ]
Panholzer TJ, Beyer J, Lichtwald K: Coupled-column liquid chromatographic analysis of catecholamines, serotonin, and metabolites in human urine. Clin Chem. 1999 Feb;45(2):262-8. [PubMed:9931050 ]
De Bellis MD, Baum AS, Birmaher B, Keshavan MS, Eccard CH, Boring AM, Jenkins FJ, Ryan ND: A.E. Bennett Research Award. Developmental traumatology. Part I: Biological stress systems. Biol Psychiatry. 1999 May 15;45(10):1259-70. [PubMed:10349032 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Reactions

Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxide	details

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Reactions

Epinephrine + Water + Oxygen → 3,4-Dihydroxymandelaldehyde + Methylamine + Hydrogen peroxide	details

Enzyme Details

3. Catechol O-methyltransferase

General function:: Involved in magnesium ion binding
Specific function:: Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:: COMT
Uniprot ID:: P21964
Molecular weight:: 30036.77

Reactions

S-Adenosylmethionine + Epinephrine → S-Adenosylhomocysteine + Metanephrine	details

Enzyme Details

4. Phenylalanine-4-hydroxylase

General function:: Involved in amino acid binding
Specific function:: Not Available
Gene Name:: PAH
Uniprot ID:: P00439
Molecular weight:: 51861.565

Enzyme Details

5. Phenylethanolamine N-methyltransferase

General function:: Involved in methyltransferase activity
Specific function:: Converts noradrenaline to adrenaline.
Gene Name:: PNMT
Uniprot ID:: P11086
Molecular weight:: 30854.745

Reactions

S-Adenosylmethionine + Norepinephrine → S-Adenosylhomocysteine + Epinephrine	details

Enzyme Details

6. Alpha-2A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:: ADRA2A
Uniprot ID:: P08913
Molecular weight:: 48956.3

Enzyme Details

7. Alpha-2B adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine > norepinephrine > epinephrine = oxymetazoline > dopamine > p-tyramine = phenylephrine > serotonin > p-synephrine / p-octopamine. For antagonists, the rank order is yohimbine > chlorpromazine > phentolamine > mianserine > spiperone > prazosin > alprenolol > propanolol > pindolol
Gene Name:: ADRA2B
Uniprot ID:: P18089
Molecular weight:: 49953.1

Enzyme Details

8. Beta-1 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity
Gene Name:: ADRB1
Uniprot ID:: P08588
Molecular weight:: 51322.1

Enzyme Details

9. Beta-2 adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine
Gene Name:: ADRB2
Uniprot ID:: P07550
Molecular weight:: 46458.3

Enzyme Details

10. Alpha-1A adrenergic receptor

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:: ADRA1A
Uniprot ID:: P35348
Molecular weight:: 51486.0

Only showing the first 10 proteins. There are 11 proteins in total.

Show all enzymes and transporters

Showing metabocard for Epinephrine (HMDB0000068)

MOL for HMDB0000068 (Epinephrine)

3D MOL for HMDB0000068 (Epinephrine)

3D SDF for HMDB0000068 (Epinephrine)

3D-SDF for HMDB0000068 (Epinephrine)

PDB for HMDB0000068 (Epinephrine)

3D PDB for HMDB0000068 (Epinephrine)

SMILES for HMDB0000068 (Epinephrine)

INCHI for HMDB0000068 (Epinephrine)

Structure for HMDB0000068 (Epinephrine)

3D Structure for HMDB0000068 (Epinephrine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions

Reactions