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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:56:24 UTC

Update Date

2023-02-21 17:30:13 UTC

HMDB ID

HMDB0060741

Secondary Accession Numbers

HMDB60741

Metabolite Identification

Common Name

3-Hydroxy-4-aminopyridine

Description

3-Hydroxy-4-aminopyridine is a metabolite of dalfampridine. 4-Aminopyridine (fampridine, USAN dalfampridine) is an organic compound with the chemical formula C5H4N–NH2. The molecule is one of the three isomeric amines of pyridine. It is used primarily as a research tool, in characterizing subtypes of potassium channel, and has also been used to manage some of the symptoms of multiple sclerosis, and is indicated for symptomatic improvement of walking in adults with several variations of the disease. (Wikipedia)

Structure

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

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₅H₆N₂O

Average Molecular Weight

110.1139

Monoisotopic Molecular Weight

110.048012824

IUPAC Name

4-imino-1,4-dihydropyridin-3-ol

Traditional Name

4-imino-1H-pyridin-3-ol

CAS Registry Number

52334-53-9

SMILES

OC1=CNC=CC1=N

InChI Identifier

InChI=1S/C5H6N2O/c6-4-1-2-7-3-5(4)8/h1-3,8H,(H2,6,7)

InChI Key

DBDKLFOUWUHPDW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aminopyridines and derivatives. These are organic heterocyclic compounds containing an amino group attached to a pyridine ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Aminopyridines and derivatives

Direct Parent

Aminopyridines and derivatives

Alternative Parents

Substituents

Hydroxypyridine
Aminopyridine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0060741)

Organ

Kidney (HMDB: HMDB0060741)
Liver (HMDB: HMDB0060741)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0060741)

Cellular substructure

Cytoplasm (HMDB: HMDB0060741)

Source

Endogenous

Endogenous (HMDB: HMDB0060741)

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
Water Solubility	5.79 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-0.72	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	9.74	ChemAxon
pKa (Strongest Basic)	11.95	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	56.11 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	42.06 m³·mol⁻¹	ChemAxon
Polarizability	10.56 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]+	120.113	31661259
DarkChem	[M-H]-	117.228	31661259
DeepCCS	[M+H]+	125.722	30932474
DeepCCS	[M-H]-	123.718	30932474
DeepCCS	[M-2H]-	159.286	30932474
DeepCCS	[M+Na]+	133.936	30932474
AllCCS	[M+H]+	122.3	32859911
AllCCS	[M+H-H2O]+	117.3	32859911
AllCCS	[M+NH4]+	127.0	32859911
AllCCS	[M+Na]+	128.4	32859911
AllCCS	[M-H]-	117.8	32859911
AllCCS	[M+Na-2H]-	120.3	32859911
AllCCS	[M+HCOO]-	123.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-4-aminopyridine	OC1=CNC=CC1=N	1998.5	Standard polar	33892256
3-Hydroxy-4-aminopyridine	OC1=CNC=CC1=N	1226.5	Standard non polar	33892256
3-Hydroxy-4-aminopyridine	OC1=CNC=CC1=N	1353.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-4-aminopyridine,1TMS,isomer #1	C[Si](C)(C)OC1=C[NH]C=CC1=N	1368.1	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,1TMS,isomer #2	C[Si](C)(C)N1C=CC(=N)C(O)=C1	1539.0	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,1TMS,isomer #3	C[Si](C)(C)N=C1C=C[NH]C=C1O	1366.4	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TMS,isomer #1	C[Si](C)(C)OC1=CN([Si](C)(C)C)C=CC1=N	1547.1	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TMS,isomer #1	C[Si](C)(C)OC1=CN([Si](C)(C)C)C=CC1=N	1552.8	Standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TMS,isomer #1	C[Si](C)(C)OC1=CN([Si](C)(C)C)C=CC1=N	1819.5	Standard polar	33892256
3-Hydroxy-4-aminopyridine,2TMS,isomer #2	C[Si](C)(C)N=C1C=C[NH]C=C1O[Si](C)(C)C	1421.7	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TMS,isomer #2	C[Si](C)(C)N=C1C=C[NH]C=C1O[Si](C)(C)C	1503.1	Standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TMS,isomer #2	C[Si](C)(C)N=C1C=C[NH]C=C1O[Si](C)(C)C	1686.4	Standard polar	33892256
3-Hydroxy-4-aminopyridine,2TMS,isomer #3	C[Si](C)(C)N=C1C=CN([Si](C)(C)C)C=C1O	1537.7	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TMS,isomer #3	C[Si](C)(C)N=C1C=CN([Si](C)(C)C)C=C1O	1601.6	Standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TMS,isomer #3	C[Si](C)(C)N=C1C=CN([Si](C)(C)C)C=C1O	1917.3	Standard polar	33892256
3-Hydroxy-4-aminopyridine,3TMS,isomer #1	C[Si](C)(C)N=C1C=CN([Si](C)(C)C)C=C1O[Si](C)(C)C	1575.6	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,3TMS,isomer #1	C[Si](C)(C)N=C1C=CN([Si](C)(C)C)C=C1O[Si](C)(C)C	1684.1	Standard non polar	33892256
3-Hydroxy-4-aminopyridine,3TMS,isomer #1	C[Si](C)(C)N=C1C=CN([Si](C)(C)C)C=C1O[Si](C)(C)C	1758.1	Standard polar	33892256
3-Hydroxy-4-aminopyridine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=C[NH]C=CC1=N	1659.0	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C=CC(=N)C(O)=C1	1813.3	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C1C=C[NH]C=C1O	1612.7	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CN([Si](C)(C)C(C)(C)C)C=CC1=N	2048.3	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CN([Si](C)(C)C(C)(C)C)C=CC1=N	1993.4	Standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CN([Si](C)(C)C(C)(C)C)C=CC1=N	2043.2	Standard polar	33892256
3-Hydroxy-4-aminopyridine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C1C=C[NH]C=C1O[Si](C)(C)C(C)(C)C	1907.1	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C1C=C[NH]C=C1O[Si](C)(C)C(C)(C)C	1920.6	Standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N=C1C=C[NH]C=C1O[Si](C)(C)C(C)(C)C	1953.1	Standard polar	33892256
3-Hydroxy-4-aminopyridine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C1C=CN([Si](C)(C)C(C)(C)C)C=C1O	2048.3	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C1C=CN([Si](C)(C)C(C)(C)C)C=C1O	2023.6	Standard non polar	33892256
3-Hydroxy-4-aminopyridine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N=C1C=CN([Si](C)(C)C(C)(C)C)C=C1O	2095.7	Standard polar	33892256
3-Hydroxy-4-aminopyridine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1C=CN([Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2259.0	Semi standard non polar	33892256
3-Hydroxy-4-aminopyridine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1C=CN([Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2304.4	Standard non polar	33892256
3-Hydroxy-4-aminopyridine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N=C1C=CN([Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2107.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4-aminopyridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-9400000000-854e425cf3f7e1cec9af	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4-aminopyridine GC-MS (1 TMS) - 70eV, Positive	splash10-02mi-9800000000-751933b430f19a4a258a	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-4-aminopyridine 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-aminopyridine 10V, Positive-QTOF	splash10-03di-0900000000-aef35aa0d7b03f901ea3	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-aminopyridine 20V, Positive-QTOF	splash10-03di-3900000000-602d0e9cfe624e745a76	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-aminopyridine 40V, Positive-QTOF	splash10-0udi-9000000000-a886af5f08537180fa05	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-aminopyridine 10V, Negative-QTOF	splash10-0a4i-2900000000-1a71b4400b892323f645	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-aminopyridine 20V, Negative-QTOF	splash10-0a4i-2900000000-e4ee0c59fe5432e69291	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-aminopyridine 40V, Negative-QTOF	splash10-0udi-9000000000-f40c6f9547b84d754eb9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-aminopyridine 10V, Positive-QTOF	splash10-03di-0900000000-93059203859099fa37d8	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-aminopyridine 20V, Positive-QTOF	splash10-0gx0-9400000000-fe0c6e95449f4e3b2399	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-aminopyridine 40V, Positive-QTOF	splash10-0udi-9000000000-de7ffb197e05e930d774	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-aminopyridine 10V, Negative-QTOF	splash10-0a4i-0900000000-54009a42432c07b2ea86	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-aminopyridine 20V, Negative-QTOF	splash10-0a4i-6900000000-be863cf6237f8cee567a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-4-aminopyridine 40V, Negative-QTOF	splash10-0udi-9000000000-5ac19836fbadf8b3b69f	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	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]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

2762419

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

Not Available

Showing metabocard for 3-Hydroxy-4-aminopyridine (HMDB0060741)

MOL for HMDB0060741 (3-Hydroxy-4-aminopyridine)

3D MOL for HMDB0060741 (3-Hydroxy-4-aminopyridine)

3D SDF for HMDB0060741 (3-Hydroxy-4-aminopyridine)

3D-SDF for HMDB0060741 (3-Hydroxy-4-aminopyridine)

PDB for HMDB0060741 (3-Hydroxy-4-aminopyridine)

3D PDB for HMDB0060741 (3-Hydroxy-4-aminopyridine)

SMILES for HMDB0060741 (3-Hydroxy-4-aminopyridine)

INCHI for HMDB0060741 (3-Hydroxy-4-aminopyridine)

Structure for HMDB0060741 (3-Hydroxy-4-aminopyridine)

3D Structure for HMDB0060741 (3-Hydroxy-4-aminopyridine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra