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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:33:07 UTC

Update Date

2022-09-22 17:44:26 UTC

HMDB ID

HMDB0255737

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Norfenefrine

Description

Norfenefrine belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. Based on a literature review a significant number of articles have been published on Norfenefrine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Norfenefrine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Norfenefrine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Norfenefrine HCL	ChEMBL
WV-569	ChEMBL
3-Octopamine	MeSH
A.S. cor	MeSH
Norfenefrin ziethen	MeSH
Norfenefrin-ratiopharm	MeSH
Novadral	MeSH
alpha-(Aminomethyl)-3-hydroxybenzyl alcohol	MeSH
m-Octopamine	MeSH
Norfenefrine citrate (1:1), (R)-(R-(r,r))-isomer	MeSH
Norfenefrine citrate (1:1), (R-(r,r))-isomer	MeSH
Norfenefrine hydrochloride	MeSH
Norfenefrine hydrochloride, (+,-)-isomer	MeSH
Norfenefrine hydrochloride, (R)-isomer	MeSH
Norfenefrine hydrochloride, (S)-isomer	MeSH
Norfenefrine sulfate	MeSH
Norfenefrine, (+)-isomer	MeSH
Norfenefrine, (+,-)-isomer	MeSH
Norfenefrine, (-)-isomer	MeSH
Norfenefrine, 2H-labeled CPD	MeSH
Norphenylephrine	MeSH

Chemical Formula

C₈H₁₁NO₂

Average Molecular Weight

153.181

Monoisotopic Molecular Weight

153.078978598

IUPAC Name

3-(2-amino-1-hydroxyethyl)phenol

Traditional Name

norfenefrine

CAS Registry Number

Not Available

SMILES

NCC(O)C1=CC(O)=CC=C1

InChI Identifier

InChI=1S/C8H11NO2/c9-5-8(11)6-2-1-3-7(10)4-6/h1-4,8,10-11H,5,9H2

InChI Key

LRCXRAABFLIVAI-UHFFFAOYSA-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
Organic oxygen compound
Aromatic alcohol
Alcohol
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (HMDB: HMDB0255737)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	-0.95	ALOGPS
logP	-0.32	ChemAxon
logS	-0.91	ALOGPS
pKa (Strongest Acidic)	9.56	ChemAxon
pKa (Strongest Basic)	8.91	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	66.48 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	42.47 m³·mol⁻¹	ChemAxon
Polarizability	15.94 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
DeepCCS	[M+H]+	132.76	30932474
DeepCCS	[M-H]-	129.145	30932474
DeepCCS	[M-2H]-	166.635	30932474
DeepCCS	[M+Na]+	142.139	30932474
AllCCS	[M+H]+	136.3	32859911
AllCCS	[M+H-H2O]+	132.1	32859911
AllCCS	[M+NH4]+	140.3	32859911
AllCCS	[M+Na]+	141.5	32859911
AllCCS	[M-H]-	131.3	32859911
AllCCS	[M+Na-2H]-	132.8	32859911
AllCCS	[M+HCOO]-	134.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Norfenefrine	NCC(O)C1=CC(O)=CC=C1	2724.4	Standard polar	33892256
Norfenefrine	NCC(O)C1=CC(O)=CC=C1	1678.3	Standard non polar	33892256
Norfenefrine	NCC(O)C1=CC(O)=CC=C1	1686.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Norfenefrine,3TMS,isomer #1	C[Si](C)(C)NCC(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	1662.3	Semi standard non polar	33892256
Norfenefrine,3TMS,isomer #1	C[Si](C)(C)NCC(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	1775.2	Standard non polar	33892256
Norfenefrine,3TMS,isomer #1	C[Si](C)(C)NCC(O[Si](C)(C)C)C1=CC=CC(O[Si](C)(C)C)=C1	1852.4	Standard polar	33892256
Norfenefrine,3TMS,isomer #2	C[Si](C)(C)OC(CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC(O)=C1	1916.7	Semi standard non polar	33892256
Norfenefrine,3TMS,isomer #2	C[Si](C)(C)OC(CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC(O)=C1	1972.2	Standard non polar	33892256
Norfenefrine,3TMS,isomer #2	C[Si](C)(C)OC(CN([Si](C)(C)C)[Si](C)(C)C)C1=CC=CC(O)=C1	1963.1	Standard polar	33892256
Norfenefrine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=CC(C(O)CN([Si](C)(C)C)[Si](C)(C)C)=C1	1919.4	Semi standard non polar	33892256
Norfenefrine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=CC(C(O)CN([Si](C)(C)C)[Si](C)(C)C)=C1	1922.3	Standard non polar	33892256
Norfenefrine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=CC(C(O)CN([Si](C)(C)C)[Si](C)(C)C)=C1	2020.1	Standard polar	33892256
Norfenefrine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	1960.4	Semi standard non polar	33892256
Norfenefrine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	1916.6	Standard non polar	33892256
Norfenefrine,4TMS,isomer #1	C[Si](C)(C)OC1=CC=CC(C(CN([Si](C)(C)C)[Si](C)(C)C)O[Si](C)(C)C)=C1	1842.7	Standard polar	33892256
Norfenefrine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2372.0	Semi standard non polar	33892256
Norfenefrine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2398.3	Standard non polar	33892256
Norfenefrine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCC(O[Si](C)(C)C(C)(C)C)C1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1	2245.4	Standard polar	33892256
Norfenefrine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1	2559.7	Semi standard non polar	33892256
Norfenefrine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1	2549.0	Standard non polar	33892256
Norfenefrine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C1=CC=CC(O)=C1	2285.2	Standard polar	33892256
Norfenefrine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2619.7	Semi standard non polar	33892256
Norfenefrine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2539.3	Standard non polar	33892256
Norfenefrine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(O)CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2347.2	Standard polar	33892256
Norfenefrine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	2814.9	Semi standard non polar	33892256
Norfenefrine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	2661.1	Standard non polar	33892256
Norfenefrine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=CC(C(CN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)=C1	2290.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9300000000-40330f2c1bf2ebefeb65	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Norfenefrine GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfenefrine 10V, Positive-QTOF	splash10-0f79-0900000000-0bda02b399d19c8ff474	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfenefrine 20V, Positive-QTOF	splash10-014r-0900000000-7c2b89c8c7a99b2c7e3a	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfenefrine 40V, Positive-QTOF	splash10-014i-9800000000-5bfd7aabfadf0af291c7	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfenefrine 10V, Negative-QTOF	splash10-0udi-0900000000-cc89bba67c70481f3dab	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfenefrine 20V, Negative-QTOF	splash10-0ul0-1900000000-b31b96036ccfcc6e0054	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Norfenefrine 40V, Negative-QTOF	splash10-0006-9400000000-89ad250cd0672b514f54	2017-07-26	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-10-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
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	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13378

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4379

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Norfenefrine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Norfenefrine (HMDB0255737)

MOL for HMDB0255737 (Norfenefrine)

3D MOL for HMDB0255737 (Norfenefrine)

3D SDF for HMDB0255737 (Norfenefrine)

3D-SDF for HMDB0255737 (Norfenefrine)

PDB for HMDB0255737 (Norfenefrine)

3D PDB for HMDB0255737 (Norfenefrine)

SMILES for HMDB0255737 (Norfenefrine)

INCHI for HMDB0255737 (Norfenefrine)

Structure for HMDB0255737 (Norfenefrine)

3D Structure for HMDB0255737 (Norfenefrine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra