MiMeDB: Showing metabocard for 5-Hydroxykynurenamine (MMDBc0047944)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-23 23:17:51 UTC

Update Date

2022-09-01 02:02:37 UTC

Metabolite ID

MMDBc0047944

Metabolite Identification

Common Name

5-Hydroxykynurenamine

Description

5-Hydroxykynurenamine is an intermediate in the tryptophan metabolic pathway [Kegg: C05638]. It is generated from 5-hydroxykynurenine via the enzyme DOPA decarboxylase.

Structure

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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      26.330 -11.661   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      22.329  -6.271   0.000  0.00  0.00           O+0
HETATM    3  N   UNK     0      26.330  -3.961   0.000  0.00  0.00           N+0
HETATM    4  N   UNK     0      20.995  -8.581   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      24.997  -4.731   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.997  -6.271   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.663  -7.041   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.997 -10.891   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.329  -9.351   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.663  -8.581   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.997  -9.351   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.663 -11.661   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.329 -10.891   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    7                                                            
CONECT    3    5                                                            
CONECT    4    9                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    2    6   10                                                  
CONECT    8    1   11   12                                                  
CONECT    9    4   10   13                                                  
CONECT   10    7    9   11                                                  
CONECT   11    8   10                                                       
CONECT   12    8   13                                                       
CONECT   13    9   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Synonyms

Value	Source
3-Amino-1-(2-amino-5-hydroxyphenyl)-1-propanone	ChEBI
Mausamine	ChEBI
Mousamine	ChEBI
5-Hydroxykynuramine	HMDB
5-Hydroxykynuramine monohydrobromide	HMDB
5-Hydroxykynuramine dihydrochloride	HMDB
5-Hydroxykynuramine dihydrobromide	HMDB

Molecular Formula

C₉H₁₂N₂O₂

Average Mass

180.2038

Monoisotopic Mass

180.089877638

IUPAC Name

3-amino-1-(2-amino-5-hydroxyphenyl)propan-1-one

Traditional Name

5-hydroxykynurenamine

CAS Registry Number

708-23-6

SMILES

NCCC(=O)C1=C(N)C=CC(O)=C1

InChI Identifier

InChI=1S/C9H12N2O2/c10-4-3-9(13)7-5-6(12)1-2-8(7)11/h1-2,5,12H,3-4,10-11H2

InChI Key

JANBBPTXDKFOQR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Aminophenol
P-aminophenol
Benzoyl
Aryl alkyl ketone
Aniline or substituted anilines
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Beta-aminoketone
Benzenoid
Vinylogous amide
Primary amine
Organic oxide
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Amine
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxykynurenamine (CHEBI:28715 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.59 g/L	ALOGPS
logP	-0.47	ALOGPS
logP	-0.13	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	10.01	ChemAxon
pKa (Strongest Basic)	9.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	89.34 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.2 m³·mol⁻¹	ChemAxon
Polarizability	18.71 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-5900000000-f09282080286ae8e6aa5	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-000i-3900000000-e0e99034c616fa690ed9	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-0900000000-fdcafa493a3a3738f189	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dj-1900000000-cc40b42cbe0bab3e9572	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0aba-8900000000-b0f4a5f21f7abe4af468	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-c870ac2fb24b5478768e	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-0900000000-c0a66828c2d20d72fea2	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-4900000000-e62241e70455598c384a	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-2b86f21423bc0444ee36	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dr-0900000000-0a9fb7f6ed0b1ae79819	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-6900000000-0b9c3a67126643a1f520	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-38cccaa8ebaeff68bb36	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1900000000-cbe38c7a27b047e43dcf	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udl-9100000000-3c7df192acbf739fd1cc	2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191832	Amine oxidase [flavin-containing] B	Unknown	P27338	Homo sapiens
MMDBp0191840	Amine oxidase [flavin-containing] A	Unknown	P21397	Homo sapiens
MMDBp0191948	Aromatic-L-amino-acid decarboxylase	Enzyme	P20711	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000121	5-Hydroxykynurenine	5-Hydroxykynurenamine	Not Available	5-Hydroxykynurenamine Decarboxy-Lyase	VMH	30371894
MMDBr0000122	5-Hydroxykynurenamine	4,6-Dihydroxyquinoline	Monoamine oxidase a	5-Hydroxykynurenamine:Oxygen Oxidoreductase (Deaminating) (Flavin-Containing)	VMH	15035803 8920635 9653080

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	46	Human feces; Pig ; Human ; Cattle	Metabolic reconstruction
Bacteria	Proteobacteria	105	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab	Metabolic reconstruction
Bacteria	Actinobacteria	44	Human feces; Human ; Human supragingival plaque	Metabolic reconstruction
Bacteria	Bacteroidetes	3	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	1	Human ; Human feces	Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0004076

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023300

KNApSAcK ID

Not Available

Chemspider ID

144400

KEGG Compound ID

C05638

BioCyc ID

Not Available

BiGG ID

46174

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

164719

PDB ID

Not Available

ChEBI ID

28715

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Makino K, Jo Y, Murakami Y, Murakami K, Hasegawa F: 5-hydroxykynuramine (mausamine). Med J Osaka Univ. 1968 Sep;19(1):27-30. [PubMed:4885724 ]
Back W: [Synthesis of o-acylamino-beta-dimethylamino-propiophenones. 4. Synthesis of primary Mannich-bases]. Arch Pharm (Weinheim). 1972 Jun;305(6):448-55. doi: 10.1002/ardp.19723050608. [PubMed:5049691 ]
Murakami Y, Makino K: Conversion of 5-hydroxykynurenine to 5-hydroxykynuramine and 4,6-dihydroxyquinoline in mouse liver homogenate. J Biochem. 1968 Jan;63(1):20-4. doi: 10.1093/oxfordjournals.jbchem.a128743. [PubMed:5655081 ]
Joh Y: Synthesis of 5-hydroxykynuramine hydrochloride (mausamine). J Biochem. 1965 Sep;58(3):248-50. doi: 10.1093/oxfordjournals.jbchem.a128193. [PubMed:5861330 ]
MAKINO K, JOH Y, HASEGAWA F: The detection of mausamine in the brain of mouse. Biochem Biophys Res Commun. 1962 Jan 24;6:432-7. doi: 10.1016/0006-291x(62)90370-4. [PubMed:14468719 ]

Showing metabocard for 5-Hydroxykynurenamine (MMDBc0047944)

MOL for #<Metabolite:0x00007fe2a457e0c0>

3D MOL for #<Metabolite:0x00007fe2a457e0c0>

3D SDF for #<Metabolite:0x00007fe2a457e0c0>

3D-SDF for #<Metabolite:0x00007fe2a457e0c0>

PDB for #<Metabolite:0x00007fe2a457e0c0>

3D PDB for #<Metabolite:0x00007fe2a457e0c0>

SMILES for #<Metabolite:0x00007fe2a457e0c0>

INCHI for #<Metabolite:0x00007fe2a457e0c0>

Structure for #<Metabolite:0x00007fe2a457e0c0>

3D Structure for #<Metabolite:0x00007fe2a457e0c0>