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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:40 UTC

Update Date

2023-02-21 17:16:14 UTC

HMDB ID

HMDB0002182

Secondary Accession Numbers

HMDB02182

Metabolite Identification

Common Name

Phenylephrine

Description

Phenylephrine, also known as mesaton or fenilefrina, belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. Phenylephrine is a very strong basic compound (based on its pKa). Phenylephrine is a bitter tasting compound. Outside of the human body,. It is often used in combination with tropicamide as a synergist when tropicamide alone is not sufficient.

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 388                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       4.414   2.017   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.080  -3.373   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0       7.081   3.557   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       5.748   1.247   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.081   2.017   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748  -0.293   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -1.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.081  -1.063   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414  -2.603   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.081  -2.603   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -3.373   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415   4.327   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    9                                                            
CONECT    3    5   12                                                       
CONECT    4    1    5    6                                                  
CONECT    5    3    4                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    2    7   11                                                  
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    3                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-m-Hydroxy-alpha-(methylaminomethyl)benzyl alcohol	ChEBI
Fenilefrina	ChEBI
L-(3-Hydroxyphenyl)-N-methylethanolamine	ChEBI
Phenylephrinum	ChEBI
R(-)-Phenylephrine	ChEBI
Phenylephrine minims	Kegg
(-)-m-Hydroxy-a-(methylaminomethyl)benzyl alcohol	Generator
(-)-m-Hydroxy-α-(methylaminomethyl)benzyl alcohol	Generator
Adrianol	HMDB
Ak-dilate	HMDB
Ak-nefrin	HMDB
Alcon efrin	HMDB
Alconefrin nasal drops 12	HMDB
Alconefrin nasal drops 25	HMDB
Alconefrin nasal drops 50	HMDB
Alconefrin nasal spray 25	HMDB
Biomydrin	HMDB
Dilatair	HMDB
Dionephrine	HMDB
Doktors	HMDB
Duration	HMDB
I-phrine	HMDB
Isophrim	HMDB
Isophrin	HMDB
Isopto frin	HMDB
m-Methylaminoethanolphenol	HMDB
m-Oxedrine	HMDB
m-Sympathol	HMDB
m-Sympatol	HMDB
m-Synephrine	HMDB
Mesaton	HMDB
Mesatone	HMDB
Mesatonum	HMDB
Metaoxedrin	HMDB
Metaoxedrine	HMDB
Metaoxedrinum	HMDB
Metasympatol	HMDB
Metasynephrine	HMDB
Mezaton	HMDB
Minims phenylephrine	HMDB
Mydfrin	HMDB
Neo-synephrine	HMDB
Neo-synephrine nasal drops	HMDB
Neo-synephrine nasal jelly	HMDB
Neo-synephrine nasal spray	HMDB
Neo-synephrine pediatric nasal drops	HMDB
Neofrin	HMDB
Neophryn	HMDB
Neosynephrine	HMDB
Nostril	HMDB
Nostril spray pump	HMDB
Nostril spray pump mild	HMDB
Ocu-phrin sterile eye drops	HMDB
Ocu-phrin sterile ophthalmic solution	HMDB
Ocugestrin	HMDB
Phenoptic	HMDB
Prefrin	HMDB
Prefrin liquifilm	HMDB
Pyracort D	HMDB
R(-)-Mezaton	HMDB
Relief eye drops for red eyes	HMDB
Rhinall	HMDB
Spersaphrine	HMDB
Vicks sinex	HMDB
Visadron	HMDB
Neo synephrine	HMDB
Phenylephrine tannate	HMDB
Tannate, phenylephrine	HMDB
(R)-3-Hydroxy-alpha-((methylamino)methyl)benzenemethanol	HMDB
Phenylephrine hydrochloride	HMDB

Chemical Formula

C₉H₁₃NO₂

Average Molecular Weight

167.205

Monoisotopic Molecular Weight

167.094628665

IUPAC Name

3-[(1R)-1-hydroxy-2-(methylamino)ethyl]phenol

Traditional Name

phenylephrine

CAS Registry Number

59-42-7

SMILES

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

InChI Identifier

InChI=1S/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/m0/s1

InChI Key

SONNWYBIRXJNDC-VIFPVBQESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-hydroxy-4-unsubstituted benzenoids

Alternative Parents

Substituents

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

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenylethanolamines (CHEBI:8093 )
secondary amino compound (CHEBI:8093 )

Ontology

Physiological effect

Organoleptic effect

Taste

Bitter

Adipose tissue (HMDB: HMDB0002182)
Adipose tissue (HMDB: HMDB0002182)

Muscle tissue

Skeletal muscle (HMDB: HMDB0002182)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 7866557)

Tissue substructure

Muscle (HMDB: HMDB0002182)

Cell

Nerve cell (HMDB: HMDB0002182)
Neuron (HMDB: HMDB0002182)

Organ

Excreta

Biofluid or Excreta

Urine (PMID: 19309105)

Source

Exogenous

Exogenous (HMDB: HMDB0002182)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0002182)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	-0.31	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	22 g/L	ALOGPS
logP	-0.69	ALOGPS
logP	-0.07	ChemAxon
logS	-0.88	ALOGPS
pKa (Strongest Acidic)	9.07	ChemAxon
pKa (Strongest Basic)	9.69	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	52.49 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	47.25 m³·mol⁻¹	ChemAxon
Polarizability	18.2 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	139.658	31661259
DarkChem	[M-H]-	135.086	31661259
DeepCCS	[M+H]+	136.64	30932474
DeepCCS	[M-H]-	134.067	30932474
DeepCCS	[M-2H]-	169.905	30932474
DeepCCS	[M+Na]+	145.425	30932474
AllCCS	[M+H]+	137.7	32859911
AllCCS	[M+H-H2O]+	133.3	32859911
AllCCS	[M+NH4]+	141.7	32859911
AllCCS	[M+Na]+	142.8	32859911
AllCCS	[M-H]-	137.1	32859911
AllCCS	[M+Na-2H]-	138.3	32859911
AllCCS	[M+HCOO]-	139.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Phenylephrine	CNC[C@H](O)C1=CC(O)=CC=C1	2744.8	Standard polar	33892256
Phenylephrine	CNC[C@H](O)C1=CC(O)=CC=C1	1613.0	Standard non polar	33892256
Phenylephrine	CNC[C@H](O)C1=CC(O)=CC=C1	1671.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Phenylephrine,1TMS,isomer #1	CNC[C@H](O[Si](C)(C)C)C1=CC=CC(O)=C1	1696.2	Semi standard non polar	33892256
Phenylephrine,1TMS,isomer #2	CNC[C@H](O)C1=CC=CC(O[Si](C)(C)C)=C1	1652.2	Semi standard non polar	33892256
Phenylephrine,1TMS,isomer #3	CN(C[C@H](O)C1=CC=CC(O)=C1)[Si](C)(C)C	1754.1	Semi standard non polar	33892256
Phenylephrine,2TMS,isomer #1	CNC[C@H](O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	1640.9	Semi standard non polar	33892256
Phenylephrine,2TMS,isomer #2	CN(C[C@H](O[Si](C)(C)C)C1=CC=CC(O)=C1)[Si](C)(C)C	1794.1	Semi standard non polar	33892256
Phenylephrine,2TMS,isomer #3	CN(C[C@H](O)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C	1804.2	Semi standard non polar	33892256
Phenylephrine,3TMS,isomer #1	CN(C[C@H](O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C	1805.8	Semi standard non polar	33892256
Phenylephrine,3TMS,isomer #1	CN(C[C@H](O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C	1802.8	Standard non polar	33892256
Phenylephrine,3TMS,isomer #1	CN(C[C@H](O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1)[Si](C)(C)C	1815.2	Standard polar	33892256
Phenylephrine,1TBDMS,isomer #1	CNC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1	1908.6	Semi standard non polar	33892256
Phenylephrine,1TBDMS,isomer #2	CNC[C@H](O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	1901.7	Semi standard non polar	33892256
Phenylephrine,1TBDMS,isomer #3	CN(C[C@H](O)C1=CC=CC(O)=C1)[Si](C)(C)C(C)(C)C	1997.2	Semi standard non polar	33892256
Phenylephrine,2TBDMS,isomer #1	CNC[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2111.5	Semi standard non polar	33892256
Phenylephrine,2TBDMS,isomer #2	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1)[Si](C)(C)C(C)(C)C	2278.6	Semi standard non polar	33892256
Phenylephrine,2TBDMS,isomer #3	CN(C[C@H](O)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2287.5	Semi standard non polar	33892256
Phenylephrine,3TBDMS,isomer #1	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2524.6	Semi standard non polar	33892256
Phenylephrine,3TBDMS,isomer #1	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2443.0	Standard non polar	33892256
Phenylephrine,3TBDMS,isomer #1	CN(C[C@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)[Si](C)(C)C(C)(C)C	2205.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Phenylephrine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-014i-0900000000-b11a2a880d1683fa6cae	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylephrine GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)	splash10-01b9-6900000000-bbdd210a846be116dbcd	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylephrine GC-EI-TOF (Non-derivatized)	splash10-014i-0900000000-b11a2a880d1683fa6cae	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Phenylephrine GC-EI-TOF (Non-derivatized)	splash10-01b9-6900000000-bbdd210a846be116dbcd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylephrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-3ea7ffd258ffba5a376a	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylephrine GC-MS (2 TMS) - 70eV, Positive	splash10-014i-4920000000-54a2b2a88914c83610f2	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Phenylephrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-0udi-0900000000-d95a741ffcfe3f7bb7e9	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-0006-9800000000-7695881b36499169fb71	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-054o-9200000000-888fce606d860cd39be2	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative-QTOF	splash10-014i-0900000000-edfcbc18ccdb6872b791	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative-QTOF	splash10-00di-0900000000-15132688bbc7ac0be42f	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative-QTOF	splash10-00di-2900000000-34ccc7192518d4c14210	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative-QTOF	splash10-00di-3900000000-e619f4210f81c11f61be	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative-QTOF	splash10-00dl-6900000000-3178337a019ac9bf313d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive-QTOF	splash10-0gb9-0900000000-e738818606836c1d6d1a	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive-QTOF	splash10-0udi-0900000000-36b72327f64f1355a502	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive-QTOF	splash10-052o-4900000000-935a9659fe39602b138d	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive-QTOF	splash10-052f-9800000000-7d83555b537d6fec673b	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive-QTOF	splash10-054o-9400000000-5ef2f6d1da57087e6ac7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOF	splash10-014i-0900000000-4a910a2109ba191b96e7	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ , negative-QTOF	splash10-014i-0900000000-edfcbc18ccdb6872b791	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ , negative-QTOF	splash10-00di-0900000000-15132688bbc7ac0be42f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ , negative-QTOF	splash10-00di-2900000000-34ccc7192518d4c14210	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ , negative-QTOF	splash10-00di-3900000000-e8a5a4f1aae0796866a7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Phenylephrine LC-ESI-QQ , negative-QTOF	splash10-00dl-6900000000-3178337a019ac9bf313d	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylephrine 10V, Positive-QTOF	splash10-0uxr-0900000000-8c4893aa69ea6a1ceecb	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylephrine 20V, Positive-QTOF	splash10-0uxr-0900000000-4406afb22d76646e2ef8	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylephrine 40V, Positive-QTOF	splash10-01c3-7900000000-56a2a2741d2166bf31bc	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylephrine 10V, Negative-QTOF	splash10-014i-0900000000-0cf5a5fa80f87facb9ad	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylephrine 20V, Negative-QTOF	splash10-014j-2900000000-687762e0d4bf3efbffec	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Phenylephrine 40V, Negative-QTOF	splash10-0006-9400000000-140e96de62b4341791d9	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Adipose Tissue
Bladder
Brain
Kidney
Neuron
Prostate
Skeletal Muscle
Spleen

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2.3 (0.029-3.0) uM	Adult (>18 years old)	Both	Normal	7866557	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	0.0019 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	19309105	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB00388

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022891

KNApSAcK ID

Not Available

Chemspider ID

5818

KEGG Compound ID

C07441

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Phenylephrine

METLIN ID

699

PubChem Compound

6041

PDB ID

Not Available

ChEBI ID

8093

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Kamiya A, Kawada T, Yamamoto K, Michikami D, Ariumi H, Miyamoto T, Uemura K, Sugimachi M, Sunagawa K: Muscle sympathetic nerve activity averaged over 1 minute parallels renal and cardiac sympathetic nerve activity in response to a forced baroreceptor pressure change. Circulation. 2005 Jul 19;112(3):384-6. Epub 2005 Jul 5. [PubMed:15998668 ]
Thebault S, Zholos A, Enfissi A, Slomianny C, Dewailly E, Roudbaraki M, Parys J, Prevarskaya N: Receptor-operated Ca2+ entry mediated by TRPC3/TRPC6 proteins in rat prostate smooth muscle (PS1) cell line. J Cell Physiol. 2005 Jul;204(1):320-8. [PubMed:15672411 ]
Rios JD, Horikawa Y, Chen LL, Kublin CL, Hodges RR, Dartt DA, Zoukhri D: Age-dependent alterations in mouse exorbital lacrimal gland structure, innervation and secretory response. Exp Eye Res. 2005 Apr;80(4):477-91. [PubMed:15781275 ]
Gao YJ, Zeng ZH, Teoh K, Sharma AM, Abouzahr L, Cybulsky I, Lamy A, Semelhago L, Lee RM: Perivascular adipose tissue modulates vascular function in the human internal thoracic artery. J Thorac Cardiovasc Surg. 2005 Oct;130(4):1130-6. [PubMed:16214530 ]
Gonzalez-Cadavid NF, Ryndin I, Vernet D, Magee TR, Rajfer J: Presence of NMDA receptor subunits in the male lower urogenital tract. J Androl. 2000 Jul-Aug;21(4):566-78. [PubMed:10901443 ]
Grassi G, Dell'Oro R, Facchini A, Quarti Trevano F, Bolla GB, Mancia G: Effect of central and peripheral body fat distribution on sympathetic and baroreflex function in obese normotensives. J Hypertens. 2004 Dec;22(12):2363-9. [PubMed:15614031 ]
Bouchelouche K, Andersen L, Alvarez S, Nordling J, Bouchelouche P: Increased contractile response to phenylephrine in detrusor of patients with bladder outlet obstruction: effect of the alpha1A and alpha1D-adrenergic receptor antagonist tamsulosin. J Urol. 2005 Feb;173(2):657-61. [PubMed:15643283 ]
Boschmann M, Krupp G, Luft FC, Klaus S, Jordan J: In vivo response to alpha(1)-adrenoreceptor stimulation in human white adipose tissue. Obes Res. 2002 Jun;10(6):555-8. [PubMed:12055332 ]
Chueh SC, Chern JW, Choong CM, Guh JH, Teng CM: Characterization of some novel alpha 1-adrenoceptor antagonists in human hyperplastic prostate. Eur J Pharmacol. 2002 Jun 7;445(1-2):125-31. [PubMed:12065203 ]
Wang SY, Song Y, Xu M, Hao TP, Han QD, Zhang YY: [Redistribution of three alpha1-adrenergic receptor subtypes in the stably transfected HEK 293A cells upon agonist stimulation.]. Sheng Li Xue Bao. 2005 Aug 25;57(4):480-5. [PubMed:16094496 ]
Guh JH, Hsieh CH, Teng CM: Investigation of the effects of some alkaloidal alpha1-adrenoceptor antagonists on human hyperplastic prostate. Eur J Pharmacol. 1999 Jun 25;374(3):503-10. [PubMed:10422796 ]
Nomiya M, Yamaguchi O: A quantitative analysis of mRNA expression of alpha 1 and beta-adrenoceptor subtypes and their functional roles in human normal and obstructed bladders. J Urol. 2003 Aug;170(2 Pt 1):649-53. [PubMed:12853849 ]
Lam KY, Yuen AP: Cancer of the larynx in Hong Kong: a clinico-pathological study. Eur J Surg Oncol. 1996 Apr;22(2):166-70. [PubMed:8608835 ]

Enzymes

Enzyme Details

1. 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

Enzyme Details

2. 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

3. 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

4. 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

Enzyme Details

5. Alpha-1B 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
Gene Name:: ADRA1B
Uniprot ID:: P35368
Molecular weight:: 56835.4

Enzyme Details

6. Ras GTPase-activating protein-binding protein 1

General function:: Involved in nucleotide binding
Specific function:: May be a regulated effector of stress granule assembly. Phosphorylation-dependent sequence-specific endoribonuclease in vitro. Cleaves exclusively between cytosine and adenine and cleaves MYC mRNA preferentially at the 3'-UTR. ATP- and magnesium-dependent helicase. Unwinds preferentially partial DNA and RNA duplexes having a 17 bp annealed portion and either a hanging 3' tail or hanging tails at both 5'- and 3'-ends. Unwinds DNA/DNA, RNA/DNA, and RNA/RNA substrates with comparable efficiency. Acts unidirectionally by moving in the 5' to 3' direction along the bound single-stranded DNA.
Gene Name:: G3BP1
Uniprot ID:: Q13283
Molecular weight:: 52164.045

Showing metabocard for Phenylephrine (HMDB0002182)

MOL for HMDB0002182 (Phenylephrine)

3D MOL for HMDB0002182 (Phenylephrine)

3D SDF for HMDB0002182 (Phenylephrine)

3D-SDF for HMDB0002182 (Phenylephrine)

PDB for HMDB0002182 (Phenylephrine)

3D PDB for HMDB0002182 (Phenylephrine)

SMILES for HMDB0002182 (Phenylephrine)

INCHI for HMDB0002182 (Phenylephrine)

Structure for HMDB0002182 (Phenylephrine)

3D Structure for HMDB0002182 (Phenylephrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes