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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 10:22:27 UTC

Update Date

2023-02-21 17:16:54 UTC

HMDB ID

HMDB0004076

Secondary Accession Numbers

HMDB04076

Metabolite Identification

Common Name

5-Hydroxykynurenamine

Description

5-Hydroxykynurenamine, also known as mausamine, 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. A hydroxykynurenamine where the hydroxy group is located at the 5-position. 5-Hydroxykynurenamine is a very strong basic compound (based on its pKa). 5-Hydroxykynurenamine exists in all living organisms, ranging from bacteria to humans. Within humans, 5-hydroxykynurenamine participates in a number of enzymatic reactions. In particular, 5-hydroxykynurenamine can be biosynthesized from 5-hydroxykynurenine; which is mediated by the enzyme aromatic-L-amino-acid decarboxylase. In addition, 5-hydroxykynurenamine can be converted into 4,6-dihydroxyquinoline; which is mediated by the enzyme kynurenine 3-monooxygenase. In humans, 5-hydroxykynurenamine is involved in tryptophan metabolism.

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

View in JSmol View NMR Assignments View Stereo Labels

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

Chemical Formula

C₉H₁₂N₂O₂

Average Molecular Weight

180.2038

Monoisotopic Molecular Weight

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 )

Ontology

Not Available

Endogenous (HMDB: HMDB0004076)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0004076)

Role

Not Available

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	0.354	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	140.512	31661259
DarkChem	[M-H]-	139.215	31661259
DeepCCS	[M+H]+	144.228	30932474
DeepCCS	[M-H]-	140.491	30932474
DeepCCS	[M-2H]-	177.908	30932474
DeepCCS	[M+Na]+	153.447	30932474
AllCCS	[M+H]+	140.2	32859911
AllCCS	[M+H-H2O]+	136.0	32859911
AllCCS	[M+NH4]+	144.1	32859911
AllCCS	[M+Na]+	145.3	32859911
AllCCS	[M-H]-	138.7	32859911
AllCCS	[M+Na-2H]-	139.6	32859911
AllCCS	[M+HCOO]-	140.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	1.52 minutes	32390414
Predicted by Siyang on May 30, 2022	8.8709 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.71 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	201.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	486.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	252.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	77.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	51.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	236.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	255.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	720.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	564.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	57.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	666.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	172.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	194.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	593.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	504.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	255.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxykynurenamine	NCCC(=O)C1=C(N)C=CC(O)=C1	3301.1	Standard polar	33892256
5-Hydroxykynurenamine	NCCC(=O)C1=C(N)C=CC(O)=C1	2025.4	Standard non polar	33892256
5-Hydroxykynurenamine	NCCC(=O)C1=C(N)C=CC(O)=C1	2084.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxykynurenamine,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N)C(C(=O)CCN)=C1	1981.2	Semi standard non polar	33892256
5-Hydroxykynurenamine,1TMS,isomer #2	C[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N	2092.8	Semi standard non polar	33892256
5-Hydroxykynurenamine,1TMS,isomer #3	C[Si](C)(C)NC1=CC=C(O)C=C1C(=O)CCN	2043.2	Semi standard non polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #1	C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C=C1C(=O)CCN	2074.9	Semi standard non polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #1	C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C=C1C(=O)CCN	2151.9	Standard non polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #1	C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C=C1C(=O)CCN	2565.3	Standard polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #2	C[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N	2078.1	Semi standard non polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #2	C[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N	2169.8	Standard non polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #2	C[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N	2677.1	Standard polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #3	C[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N[Si](C)(C)C	2201.0	Semi standard non polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #3	C[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N[Si](C)(C)C	2318.2	Standard non polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #3	C[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N[Si](C)(C)C	2585.5	Standard polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #4	C[Si](C)(C)N(CCC(=O)C1=CC(O)=CC=C1N)[Si](C)(C)C	2259.0	Semi standard non polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #4	C[Si](C)(C)N(CCC(=O)C1=CC(O)=CC=C1N)[Si](C)(C)C	2358.3	Standard non polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #4	C[Si](C)(C)N(CCC(=O)C1=CC(O)=CC=C1N)[Si](C)(C)C	2893.7	Standard polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #5	C[Si](C)(C)N(C1=CC=C(O)C=C1C(=O)CCN)[Si](C)(C)C	2110.4	Semi standard non polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #5	C[Si](C)(C)N(C1=CC=C(O)C=C1C(=O)CCN)[Si](C)(C)C	2241.6	Standard non polar	33892256
5-Hydroxykynurenamine,2TMS,isomer #5	C[Si](C)(C)N(C1=CC=C(O)C=C1C(=O)CCN)[Si](C)(C)C	2708.6	Standard polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #1	C[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N[Si](C)(C)C	2203.6	Semi standard non polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #1	C[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N[Si](C)(C)C	2233.5	Standard non polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #1	C[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N[Si](C)(C)C	2364.8	Standard polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C(=O)CCN)=C1	2086.1	Semi standard non polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C(=O)CCN)=C1	2249.3	Standard non polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #2	C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C(=O)CCN)=C1	2383.0	Standard polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(N)C(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)=C1	2261.6	Semi standard non polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(N)C(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)=C1	2352.4	Standard non polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #3	C[Si](C)(C)OC1=CC=C(N)C(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)=C1	2625.9	Standard polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #4	C[Si](C)(C)NC1=CC=C(O)C=C1C(=O)CCN([Si](C)(C)C)[Si](C)(C)C	2359.6	Semi standard non polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #4	C[Si](C)(C)NC1=CC=C(O)C=C1C(=O)CCN([Si](C)(C)C)[Si](C)(C)C	2509.0	Standard non polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #4	C[Si](C)(C)NC1=CC=C(O)C=C1C(=O)CCN([Si](C)(C)C)[Si](C)(C)C	2473.8	Standard polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #5	C[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2209.5	Semi standard non polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #5	C[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2392.5	Standard non polar	33892256
5-Hydroxykynurenamine,3TMS,isomer #5	C[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2386.3	Standard polar	33892256
5-Hydroxykynurenamine,4TMS,isomer #1	C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C=C1C(=O)CCN([Si](C)(C)C)[Si](C)(C)C	2366.2	Semi standard non polar	33892256
5-Hydroxykynurenamine,4TMS,isomer #1	C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C=C1C(=O)CCN([Si](C)(C)C)[Si](C)(C)C	2369.5	Standard non polar	33892256
5-Hydroxykynurenamine,4TMS,isomer #1	C[Si](C)(C)NC1=CC=C(O[Si](C)(C)C)C=C1C(=O)CCN([Si](C)(C)C)[Si](C)(C)C	2342.4	Standard polar	33892256
5-Hydroxykynurenamine,4TMS,isomer #2	C[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2196.6	Semi standard non polar	33892256
5-Hydroxykynurenamine,4TMS,isomer #2	C[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2314.9	Standard non polar	33892256
5-Hydroxykynurenamine,4TMS,isomer #2	C[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C)=CC=C1N([Si](C)(C)C)[Si](C)(C)C	2212.0	Standard polar	33892256
5-Hydroxykynurenamine,4TMS,isomer #3	C[Si](C)(C)N(CCC(=O)C1=CC(O)=CC=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2366.3	Semi standard non polar	33892256
5-Hydroxykynurenamine,4TMS,isomer #3	C[Si](C)(C)N(CCC(=O)C1=CC(O)=CC=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2553.7	Standard non polar	33892256
5-Hydroxykynurenamine,4TMS,isomer #3	C[Si](C)(C)N(CCC(=O)C1=CC(O)=CC=C1N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C	2328.4	Standard polar	33892256
5-Hydroxykynurenamine,5TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)=C1	2406.7	Semi standard non polar	33892256
5-Hydroxykynurenamine,5TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)=C1	2437.8	Standard non polar	33892256
5-Hydroxykynurenamine,5TMS,isomer #1	C[Si](C)(C)OC1=CC=C(N([Si](C)(C)C)[Si](C)(C)C)C(C(=O)CCN([Si](C)(C)C)[Si](C)(C)C)=C1	2189.7	Standard polar	33892256
5-Hydroxykynurenamine,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N)C(C(=O)CCN)=C1	2261.4	Semi standard non polar	33892256
5-Hydroxykynurenamine,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N	2354.4	Semi standard non polar	33892256
5-Hydroxykynurenamine,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NC1=CC=C(O)C=C1C(=O)CCN	2350.8	Semi standard non polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1C(=O)CCN	2596.3	Semi standard non polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1C(=O)CCN	2606.3	Standard non polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1C(=O)CCN	2675.8	Standard polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N	2592.7	Semi standard non polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N	2602.0	Standard non polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N	2779.2	Standard polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N[Si](C)(C)C(C)(C)C	2733.4	Semi standard non polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N[Si](C)(C)C(C)(C)C	2748.0	Standard non polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N[Si](C)(C)C(C)(C)C	2687.6	Standard polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCC(=O)C1=CC(O)=CC=C1N)[Si](C)(C)C(C)(C)C	2717.9	Semi standard non polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCC(=O)C1=CC(O)=CC=C1N)[Si](C)(C)C(C)(C)C	2747.5	Standard non polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N(CCC(=O)C1=CC(O)=CC=C1N)[Si](C)(C)C(C)(C)C	2879.5	Standard polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=CC=C(O)C=C1C(=O)CCN)[Si](C)(C)C(C)(C)C	2588.9	Semi standard non polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=CC=C(O)C=C1C(=O)CCN)[Si](C)(C)C(C)(C)C	2619.6	Standard non polar	33892256
5-Hydroxykynurenamine,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)N(C1=CC=C(O)C=C1C(=O)CCN)[Si](C)(C)C(C)(C)C	2725.4	Standard polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N[Si](C)(C)C(C)(C)C	2906.0	Semi standard non polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N[Si](C)(C)C(C)(C)C	2853.0	Standard non polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N[Si](C)(C)C(C)(C)C	2678.7	Standard polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C(=O)CCN)=C1	2800.7	Semi standard non polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C(=O)CCN)=C1	2803.6	Standard non polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C(=O)CCN)=C1	2634.0	Standard polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(N)C(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2976.8	Semi standard non polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(N)C(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2935.7	Standard non polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(N)C(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2801.9	Standard polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=CC=C(O)C=C1C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3076.3	Semi standard non polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=CC=C(O)C=C1C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3047.0	Standard non polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)NC1=CC=C(O)C=C1C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2721.8	Standard polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2879.0	Semi standard non polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2947.8	Standard non polar	33892256
5-Hydroxykynurenamine,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2663.1	Standard polar	33892256
5-Hydroxykynurenamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3295.2	Semi standard non polar	33892256
5-Hydroxykynurenamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3092.8	Standard non polar	33892256
5-Hydroxykynurenamine,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)NC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2747.6	Standard polar	33892256
5-Hydroxykynurenamine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3094.2	Semi standard non polar	33892256
5-Hydroxykynurenamine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3033.5	Standard non polar	33892256
5-Hydroxykynurenamine,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)NCCC(=O)C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2648.2	Standard polar	33892256
5-Hydroxykynurenamine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC(=O)C1=CC(O)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3225.5	Semi standard non polar	33892256
5-Hydroxykynurenamine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC(=O)C1=CC(O)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3217.1	Standard non polar	33892256
5-Hydroxykynurenamine,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N(CCC(=O)C1=CC(O)=CC=C1N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2688.7	Standard polar	33892256
5-Hydroxykynurenamine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3486.8	Semi standard non polar	33892256
5-Hydroxykynurenamine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	3263.4	Standard non polar	33892256
5-Hydroxykynurenamine,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C(C(=O)CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C1	2685.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxykynurenamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0019-5900000000-f09282080286ae8e6aa5	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxykynurenamine GC-MS (1 TMS) - 70eV, Positive	splash10-000i-3900000000-e0e99034c616fa690ed9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-Hydroxykynurenamine 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 - 5-Hydroxykynurenamine 10V, Positive-QTOF	splash10-03e9-0900000000-fdcafa493a3a3738f189	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxykynurenamine 20V, Positive-QTOF	splash10-03dj-1900000000-cc40b42cbe0bab3e9572	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxykynurenamine 40V, Positive-QTOF	splash10-0aba-8900000000-b0f4a5f21f7abe4af468	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxykynurenamine 10V, Negative-QTOF	splash10-004i-0900000000-c870ac2fb24b5478768e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxykynurenamine 20V, Negative-QTOF	splash10-0fb9-0900000000-c0a66828c2d20d72fea2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxykynurenamine 40V, Negative-QTOF	splash10-0a4i-4900000000-e62241e70455598c384a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxykynurenamine 10V, Positive-QTOF	splash10-01q9-0900000000-2b86f21423bc0444ee36	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxykynurenamine 20V, Positive-QTOF	splash10-03dr-0900000000-0a9fb7f6ed0b1ae79819	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxykynurenamine 40V, Positive-QTOF	splash10-0a4i-6900000000-0b9c3a67126643a1f520	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxykynurenamine 10V, Negative-QTOF	splash10-004i-0900000000-38cccaa8ebaeff68bb36	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxykynurenamine 20V, Negative-QTOF	splash10-0a4i-1900000000-cbe38c7a27b047e43dcf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxykynurenamine 40V, Negative-QTOF	splash10-0udl-9100000000-3c7df192acbf739fd1cc	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
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, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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
Predicted 1D NMR	¹H 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]-)	2023-02-03	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

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

Normal Concentrations

Not Available

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

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

VMH ID

5HXKYNAM

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [PubMed:14468719 ]
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. [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. [PubMed:5655081 ]
Joh Y: Synthesis of 5-hydroxykynuramine hydrochloride (mausamine). J Biochem. 1965 Sep;58(3):248-50. [PubMed:5861330 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] B

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. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:: MAOB
Uniprot ID:: P27338
Molecular weight:: 58762.475

Reactions

5-Hydroxykynurenamine + Water + Oxygen → 4,6-Dihydroxyquinoline + Ammonia + Hydrogen peroxide + Water	details

Enzyme Details

2. 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

Reactions

5-Hydroxykynurenamine + Water + Oxygen → 4,6-Dihydroxyquinoline + Ammonia + Hydrogen peroxide + Water	details

Enzyme Details

3. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P20711
Molecular weight:: 53893.755

Reactions

5-Hydroxykynurenamine + Carbon dioxide → 5-Hydroxykynurenine	details

Showing metabocard for 5-Hydroxykynurenamine (HMDB0004076)

MOL for HMDB0004076 (5-Hydroxykynurenamine)

3D MOL for HMDB0004076 (5-Hydroxykynurenamine)

3D SDF for HMDB0004076 (5-Hydroxykynurenamine)

3D-SDF for HMDB0004076 (5-Hydroxykynurenamine)

PDB for HMDB0004076 (5-Hydroxykynurenamine)

3D PDB for HMDB0004076 (5-Hydroxykynurenamine)

SMILES for HMDB0004076 (5-Hydroxykynurenamine)

INCHI for HMDB0004076 (5-Hydroxykynurenamine)

Structure for HMDB0004076 (5-Hydroxykynurenamine)

3D Structure for HMDB0004076 (5-Hydroxykynurenamine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions

Reactions

Reactions