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enzymes (4) Show 4 proteins

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-18 09:17:15 UTC

Update Date

2023-02-21 17:15:59 UTC

HMDB ID

HMDB0001943

Secondary Accession Numbers

HMDB01943

Metabolite Identification

Common Name

Pseudoephedrine

Description

Pseudoephedrine is a member of the class of phenylethanolamines that is (1S)-2-(methylamino)-1-phenylethan-1-ol in which the pro-S hydrogen at position 2 is replaced by a methyl group. It has a role as a sympathomimetic agent, an anti-asthmatic drug, a bronchodilator agent, a vasoconstrictor agent, a central nervous system drug, a nasal decongestant, a xenobiotic and a plant metabolite. It is a secondary alcohol, a secondary amino compound and a member of phenylethanolamines. It is a conjugate base of a pseudoephedrine(1+). Pseudoephedrine is a sympathomimetic drug of the phenethylamine and amphetamine chemical classes. It may be used as a nasal/sinus decongestant, as a stimulant, or as a wakefulness-promoting agent in higher doses. It was first characterized in 1889, by the German chemists Ladenburg and Oelschlägel, who used a sample that had been isolated from Ephedra vulgaris by the Merck pharmaceutical corporation of Darmstadt, Germany. The salts pseudoephedrine hydrochloride and pseudoephedrine sulfate are found in many over-the-counter preparations, either as a single ingredient or (more commonly) in a fixed-dose combination with one or more additional active ingredients such as antihistamines, guaifenesin, dextromethorphan, paracetamol (acetaminophen) or an NSAID (such as aspirin or ibuprofen). At first, pseudoephedrine was known as a natural substance that occurs in shrubs of the Ephedra genus, which grow worldwide. Almost all commercial pseudoephedrine, however, is produced by fermenting dextrose in the presence of benzaldehyde. The primary product, (R)-phenylacetylcarbinol, is aminated to make pseudoephedrine. Pseudoephedrine acts on α- and β2-adrenergic receptors, to cause vasoconstriction and relaxation of smooth muscle in the bronchi, respectively. α-Adrenergic receptors are located on the muscles lining the walls of blood vessels. When these receptors are activated, the muscles contract, causing the blood vessels to constrict (vasoconstriction). The constricted blood vessels now allow less fluid to leave the blood vessels and enter the nose, throat and sinus linings, which results in decreased inflammation of nasal membranes, as well as decreased mucus production. Thus, by constriction of blood vessels, mainly those located in the nasal passages, pseudoephedrine causes a decrease in the symptoms of nasal congestion. Activation of β2-adrenergic receptors produces relaxation of smooth muscle of the bronchi, causing bronchial dilation and in turn decreasing congestion (although not fluid) and difficulty breathing.

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 852                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       3.080   1.540   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       5.748   3.080   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       5.748   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.748  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.080  -1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.748  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.080  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414  -3.850   0.000  0.00  0.00           C+0
CONECT    1    4                                                            
CONECT    2    3    9                                                       
CONECT    3    2    4    6                                                  
CONECT    4    1    3    5                                                  
CONECT    5    4    7    8                                                  
CONECT    6    3                                                            
CONECT    7    5   10                                                       
CONECT    8    5   11                                                       
CONECT    9    2                                                            
CONECT   10    7   12                                                       
CONECT   11    8   12                                                       
CONECT   12   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

COMPND    HMDB0001943
HETATM    1  C1  UNL     1      -2.822   0.485  -1.170  1.00  0.00           C  
HETATM    2  N1  UNL     1      -1.607  -0.055  -0.664  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.212   0.393   0.633  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.229   0.002   1.710  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.076  -0.282   1.000  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.180  -1.669   0.992  1.00  0.00           O  
HETATM    7  C5  UNL     1       1.172  -0.052   0.051  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.214   0.959  -0.879  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.288   1.098  -1.734  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.346   0.241  -1.691  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.313  -0.774  -0.764  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.244  -0.926   0.099  1.00  0.00           C  
HETATM   13  H1  UNL     1      -3.589   0.725  -0.430  1.00  0.00           H  
HETATM   14  H2  UNL     1      -3.241  -0.253  -1.902  1.00  0.00           H  
HETATM   15  H3  UNL     1      -2.608   1.447  -1.722  1.00  0.00           H  
HETATM   16  H4  UNL     1      -1.400  -1.028  -0.895  1.00  0.00           H  
HETATM   17  H5  UNL     1      -1.167   1.482   0.637  1.00  0.00           H  
HETATM   18  H6  UNL     1      -2.423   0.828   2.414  1.00  0.00           H  
HETATM   19  H7  UNL     1      -3.187  -0.324   1.271  1.00  0.00           H  
HETATM   20  H8  UNL     1      -1.864  -0.865   2.318  1.00  0.00           H  
HETATM   21  H9  UNL     1       0.441  -0.046   2.020  1.00  0.00           H  
HETATM   22  H10 UNL     1       0.154  -2.095   0.163  1.00  0.00           H  
HETATM   23  H11 UNL     1       0.392   1.635  -0.920  1.00  0.00           H  
HETATM   24  H12 UNL     1       2.238   1.935  -2.446  1.00  0.00           H  
HETATM   25  H13 UNL     1       4.177   0.342  -2.346  1.00  0.00           H  
HETATM   26  H14 UNL     1       4.174  -1.451  -0.749  1.00  0.00           H  
HETATM   27  H15 UNL     1       2.301  -1.752   0.794  1.00  0.00           H  
CONECT    1    2   13   14   15
CONECT    2    3   16
CONECT    3    4    5   17
CONECT    4   18   19   20
CONECT    5    6    7   21
CONECT    6   22
CONECT    7    8    8   12
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   25
CONECT   11   12   12   26
CONECT   12   27
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(+) Threo-2-(methylamino)-1-phenyl-1-propanol	ChEBI
(+)-(1S,2S)-Pseudoephedrine	ChEBI
(+)-Pseudoephedrine	ChEBI
(+)-Psi-ephedrine	ChEBI
(+)-Threo-ephedrine	ChEBI
(1S,2S)-(+)-Pseudoephedrine	ChEBI
(1S,2S)-Pseudoephedrine	ChEBI
2-(Methylamino)-1-phenyl-1-propanol	ChEBI
D-Isoephedrine	ChEBI
D-Pseudoephedrine	ChEBI
D-Psi-2-methylamino-1-phenyl-1-propanol	ChEBI
D-Psi-ephedrine	ChEBI
Isoephedrine	ChEBI
L(+)-Psi-ephedrine	ChEBI
L-(+)-Pseudoephedrine	ChEBI
Pseudoefedrina	ChEBI
Pseudoephedrine D-form	ChEBI
Pseudoephedrinum	ChEBI
Psi-ephedrin	ChEBI
Psi-ephedrine	ChEBI
trans-Ephedrine	ChEBI
Neodurasina	Kegg
Acunaso	Kegg
1-Ephedrine	HMDB
Besan	HMDB
D-Pseudoephedrine base	HMDB
Novafed	HMDB
Pseudoephedrine ephedrine	HMDB
Sudafed	HMDB
Ephedrine threo isomer	HMDB
Pseudoephedrine HCL	HMDB
Threo isomer OF ephedrine	HMDB
Pseudoephedrine hydrochloride	HMDB

Chemical Formula

C₁₀H₁₅NO

Average Molecular Weight

165.2322

Monoisotopic Molecular Weight

165.115364107

IUPAC Name

(1S,2S)-2-(methylamino)-1-phenylpropan-1-ol

Traditional Name

pseudoephedrine

CAS Registry Number

90-82-4

SMILES

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

InChI Identifier

InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1

InChI Key

KWGRBVOPPLSCSI-WCBMZHEXSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpropanes

Direct Parent

Phenylpropanes

Alternative Parents

Substituents

Phenylpropane
Aralkylamine
1,2-aminoalcohol
Secondary alcohol
Secondary aliphatic amine
Secondary amine
Alcohol
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Amine
Aromatic alcohol
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary alcohol (CHEBI:51209 )
secondary amine (CHEBI:51209 )
Phenylalanine derived alkaloids (C02765 )

Ontology

Physiological effect

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0001943)
Extracellular (HMDB: HMDB0001943)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0001943)

Excreta

Biofluid or Excreta

Feces (PMID: 25037050)
Urine (PMID: 32966057)

Process

Not Available

Role

Industrial application

Sympathomimetic agent (HMDB: HMDB0001943)
Vasoconstrictor agent (HMDB: HMDB0001943)
Bronchodilator agent (HMDB: HMDB0001943)
Nasal decongestant (HMDB: HMDB0001943)

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0001943)
Central nervous system drug (HMDB: HMDB0001943)
Anti-asthmatic drug (HMDB: HMDB0001943)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	119 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	0.89	KRIL,MB & FUNG,HL (1990)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.26 g/L	ALOGPS
logP	1	ALOGPS
logP	1.32	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	13.89	ChemAxon
pKa (Strongest Basic)	9.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	32.26 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	49.69 m³·mol⁻¹	ChemAxon
Polarizability	18.83 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	138.332	31661259
DarkChem	[M-H]-	136.21	31661259
AllCCS	[M+H]+	138.32	32859911
AllCCS	[M-H]-	139.184	32859911
DeepCCS	[M+H]+	143.072	30932474
DeepCCS	[M-H]-	140.677	30932474
DeepCCS	[M-2H]-	174.016	30932474
DeepCCS	[M+Na]+	148.985	30932474
AllCCS	[M+H]+	138.3	32859911
AllCCS	[M+H-H2O]+	133.9	32859911
AllCCS	[M+NH4]+	142.4	32859911
AllCCS	[M+Na]+	143.6	32859911
AllCCS	[M-H]-	139.2	32859911
AllCCS	[M+Na-2H]-	140.4	32859911
AllCCS	[M+HCOO]-	141.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pseudoephedrine	CN[C@@H](C)[C@@H](O)C1=CC=CC=C1	2130.9	Standard polar	33892256
Pseudoephedrine	CN[C@@H](C)[C@@H](O)C1=CC=CC=C1	1344.6	Standard non polar	33892256
Pseudoephedrine	CN[C@@H](C)[C@@H](O)C1=CC=CC=C1	1380.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Pseudoephedrine,1TMS,isomer #1	CN[C@@H](C)[C@@H](O[Si](C)(C)C)C1=CC=CC=C1	1413.7	Semi standard non polar	33892256
Pseudoephedrine,1TMS,isomer #2	C[C@@H]([C@@H](O)C1=CC=CC=C1)N(C)[Si](C)(C)C	1524.2	Semi standard non polar	33892256
Pseudoephedrine,2TMS,isomer #1	C[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C	1572.6	Semi standard non polar	33892256
Pseudoephedrine,2TMS,isomer #1	C[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C	1556.8	Standard non polar	33892256
Pseudoephedrine,2TMS,isomer #1	C[C@@H]([C@@H](O[Si](C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C	1691.1	Standard polar	33892256
Pseudoephedrine,1TBDMS,isomer #1	CN[C@@H](C)[C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1	1643.6	Semi standard non polar	33892256
Pseudoephedrine,1TBDMS,isomer #2	C[C@@H]([C@@H](O)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C	1754.6	Semi standard non polar	33892256
Pseudoephedrine,2TBDMS,isomer #1	C[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C	2047.3	Semi standard non polar	33892256
Pseudoephedrine,2TBDMS,isomer #1	C[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C	1989.4	Standard non polar	33892256
Pseudoephedrine,2TBDMS,isomer #1	C[C@@H]([C@@H](O[Si](C)(C)C(C)(C)C)C1=CC=CC=C1)N(C)[Si](C)(C)C(C)(C)C	2002.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Pseudoephedrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-9200000000-0c3fe6959703a851b9cc	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pseudoephedrine GC-MS (1 TMS) - 70eV, Positive	splash10-05cr-4900000000-d9ac11e33b32a9e427ad	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pseudoephedrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9000000000-8f0484f72b48017f1f2e	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pseudoephedrine Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-016s-3900000000-868bf4bba93d8b4be696	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pseudoephedrine Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-0159-2900000000-6c55fc67b7576cb42a8a	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Pseudoephedrine Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-0006-9700000000-459686cbaf7d3b59c202	2012-07-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoephedrine 10V, Positive-QTOF	splash10-00kb-0900000000-677d622716b4c2545f16	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoephedrine 20V, Positive-QTOF	splash10-00kb-2900000000-416def0e527ddf116a39	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoephedrine 40V, Positive-QTOF	splash10-0aou-9500000000-155625a572f19610e138	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoephedrine 10V, Negative-QTOF	splash10-03di-0900000000-ea7e1b550b5dc0d6d41d	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoephedrine 20V, Negative-QTOF	splash10-03dj-2900000000-f4de25860574bb60daf1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoephedrine 40V, Negative-QTOF	splash10-0a6r-9600000000-62e375458e5f83795e90	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoephedrine 10V, Negative-QTOF	splash10-0297-3900000000-4496fbcd8548f7ccc58a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoephedrine 20V, Negative-QTOF	splash10-014i-1900000000-03e637debccd8d202e3c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoephedrine 40V, Negative-QTOF	splash10-004i-9100000000-7ead088c2f003219a1cf	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoephedrine 10V, Positive-QTOF	splash10-0002-0900000000-0282f3e8fc4bf9296a38	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoephedrine 20V, Positive-QTOF	splash10-014m-3900000000-8ee8987e88c6a5601ef7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pseudoephedrine 40V, Positive-QTOF	splash10-0006-9300000000-e3932e53d7936649b8db	2021-09-25	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	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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
Feces
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Blood	Detected and Quantified	3.02 (0.012-6.05) uM	Adult (>18 years old)	Both	Normal	17230461	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

Colorectal cancer
Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

DB00852

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Pseudoephedrine

METLIN ID

2189

PubChem Compound

7028

PDB ID

Not Available

ChEBI ID

51209

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)

Download (PDF)

General References

Not Available

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. 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

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

Showing metabocard for Pseudoephedrine (HMDB0001943)

MOL for HMDB0001943 (Pseudoephedrine)

3D MOL for HMDB0001943 (Pseudoephedrine)

3D SDF for HMDB0001943 (Pseudoephedrine)

3D-SDF for HMDB0001943 (Pseudoephedrine)

PDB for HMDB0001943 (Pseudoephedrine)

3D PDB for HMDB0001943 (Pseudoephedrine)

SMILES for HMDB0001943 (Pseudoephedrine)

INCHI for HMDB0001943 (Pseudoephedrine)

Structure for HMDB0001943 (Pseudoephedrine)

3D Structure for HMDB0001943 (Pseudoephedrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes