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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-01-30 15:46:08 UTC

Update Date

2021-09-14 15:20:32 UTC

HMDB ID

HMDB0011639

Secondary Accession Numbers

HMDB11639

Metabolite Identification

Common Name

Topaquinone

Description

Topaquinone (TPQ), is the quinone of 2,4,5-trihydroxyphenylalanine. TPQ is the cofactor in most copper-containing amine oxidases. It is produced by post-translational modification of a strictly conserved active-site tyrosine residue with the participation of the copper ion at the active site. Once formed, TPQ acts as a switch between the heterolytic transformation of amine substrates to aldehydes, via a pyridoxal phosphate-like Schiff base complex, and one electron chemistry involving reduction of molecular oxygen (PMID: 12686122 ).

Structure

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


  Mrv1652309042000342D          

 15 15  0  0  1  0            999 V2000
   10.6245   -7.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6245   -8.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9100   -7.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9100   -8.7471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1955   -7.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1955   -8.3346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9100   -9.5721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4811   -8.7471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9100   -6.2720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3390   -7.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0535   -7.5096    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.7680   -7.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4824   -7.5096    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7680   -6.2720    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0535   -8.3346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  4  2  0  0  0  0
  8  6  2  0  0  0  0
  9  3  1  0  0  0  0
 10  1  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 12  2  0  0  0  0
 11 15  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0011639

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11H,1,10H2,(H,14,15)/t5-/m0/s1

> <INCHI_KEY>
YWRFBISQAMHSIX-YFKPBYRVSA-N

> <FORMULA>
C9H9NO5

> <MOLECULAR_WEIGHT>
211.1715

> <EXACT_MASS>
211.048072403

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.846902845749458

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-3-(6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid

> <ALOGPS_LOGP>
-2.00

> <JCHEM_LOGP>
-2.7921812074213297

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
5.0745824185101345

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.730048513025273

> <JCHEM_PKA_STRONGEST_BASIC>
8.775936886531614

> <JCHEM_POLAR_SURFACE_AREA>
117.69000000000001

> <JCHEM_REFRACTIVITY>
51.370400000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-3-(6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      19.832 -14.018   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.832 -15.558   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.499 -13.248   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      18.499 -16.328   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.165 -14.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      17.165 -15.558   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      18.499 -17.868   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      15.831 -16.328   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      18.499 -11.708   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      21.166 -13.248   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.500 -14.018   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.834 -13.248   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      25.167 -14.018   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      23.834 -11.708   0.000  0.00  0.00           O+0
HETATM   15  N   UNK     0      22.500 -15.558   0.000  0.00  0.00           N+0
CONECT    1    2    3   10                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5    9                                                  
CONECT    4    2    6    7                                                  
CONECT    5    3    6                                                       
CONECT    6    4    5    8                                                  
CONECT    7    4                                                            
CONECT    8    6                                                            
CONECT    9    3                                                            
CONECT   10    1   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(S)-a-Amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoate	HMDB
(S)-a-Amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acid	HMDB
(S)-alpha-Amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoate	HMDB
(S)-alpha-Amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acid	HMDB
2,4,5-Trihydroxyphenylalanine quinone	HMDB
6-Hydroxydopa quinone	HMDB
6-Hydroxydopaquinone	HMDB
a-Amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoate	HMDB
a-Amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoic acid	HMDB
alpha-Amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoate	HMDB
alpha-Amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoic acid	HMDB
O-Topaquinone	HMDB
Topa quinone	HMDB
TPQ	HMDB
6-Hydroxydopa quinone, (6-OH-3,4-dioxo)-tautomer	HMDB
6-Hydroxyphenylalanine-3,4-dione	HMDB

Chemical Formula

C₉H₉NO₅

Average Molecular Weight

211.1715

Monoisotopic Molecular Weight

211.048072403

IUPAC Name

(2S)-2-amino-3-(6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid

Traditional Name

(2S)-2-amino-3-(6-hydroxy-3,4-dioxocyclohexa-1,5-dien-1-yl)propanoic acid

CAS Registry Number

64192-68-3

SMILES

N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(O)=O

InChI Identifier

InChI=1S/C9H9NO5/c10-5(9(14)15)1-4-2-7(12)8(13)3-6(4)11/h2-3,5,11H,1,10H2,(H,14,15)/t5-/m0/s1

InChI Key

YWRFBISQAMHSIX-YFKPBYRVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
O-benzoquinone
Quinone
Vinylogous acid
Ketone
Amino acid
Cyclic ketone
Carboxylic acid
Enol
Monocarboxylic acid or derivatives
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

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	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.86 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.8	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.73	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	117.69 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	51.37 m³·mol⁻¹	ChemAxon
Polarizability	18.85 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]+	145.562	30932474
DeepCCS	[M-H]-	143.167	30932474
DeepCCS	[M-2H]-	176.355	30932474
DeepCCS	[M+Na]+	151.539	30932474
AllCCS	[M+H]+	145.6	32859911
AllCCS	[M+H-H2O]+	141.6	32859911
AllCCS	[M+NH4]+	149.2	32859911
AllCCS	[M+Na]+	150.3	32859911
AllCCS	[M-H]-	141.9	32859911
AllCCS	[M+Na-2H]-	142.2	32859911
AllCCS	[M+HCOO]-	142.6	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.	1.85 minutes	32390414
Predicted by Siyang on May 30, 2022	9.9463 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	7.81 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	327.5 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	478.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	302.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	49.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	173.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	266.2 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	236.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	779.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	616.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	42.0 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	797.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	186.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	190.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	654.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	373.2 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	438.2 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Topaquinone	N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(O)=O	3209.0	Standard polar	33892256
Topaquinone	N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(O)=O	1737.4	Standard non polar	33892256
Topaquinone	N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(O)=O	2187.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Topaquinone,1TMS,isomer #1	C[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@H](N)C(=O)O	2213.8	Semi standard non polar	33892256
Topaquinone,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(=O)C(=O)C=C1O	2126.5	Semi standard non polar	33892256
Topaquinone,1TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(=O)O	2195.3	Semi standard non polar	33892256
Topaquinone,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C	2258.5	Semi standard non polar	33892256
Topaquinone,2TMS,isomer #2	C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C)C(=O)O	2262.1	Semi standard non polar	33892256
Topaquinone,2TMS,isomer #3	C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(=O)O[Si](C)(C)C	2190.3	Semi standard non polar	33892256
Topaquinone,2TMS,isomer #4	C[Si](C)(C)N([C@@H](CC1=CC(=O)C(=O)C=C1O)C(=O)O)[Si](C)(C)C	2320.1	Semi standard non polar	33892256
Topaquinone,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2287.2	Semi standard non polar	33892256
Topaquinone,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C)C(=O)O[Si](C)(C)C	2211.7	Standard non polar	33892256
Topaquinone,3TMS,isomer #1	C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C)C(=O)O[Si](C)(C)C	3197.4	Standard polar	33892256
Topaquinone,3TMS,isomer #2	C[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2383.9	Semi standard non polar	33892256
Topaquinone,3TMS,isomer #2	C[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	2272.1	Standard non polar	33892256
Topaquinone,3TMS,isomer #2	C[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C	3278.1	Standard polar	33892256
Topaquinone,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O)N([Si](C)(C)C)[Si](C)(C)C	2325.7	Semi standard non polar	33892256
Topaquinone,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O)N([Si](C)(C)C)[Si](C)(C)C	2307.2	Standard non polar	33892256
Topaquinone,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O)N([Si](C)(C)C)[Si](C)(C)C	3296.9	Standard polar	33892256
Topaquinone,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2384.3	Semi standard non polar	33892256
Topaquinone,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	2321.7	Standard non polar	33892256
Topaquinone,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C)N([Si](C)(C)C)[Si](C)(C)C	3072.0	Standard polar	33892256
Topaquinone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@H](N)C(=O)O	2471.2	Semi standard non polar	33892256
Topaquinone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(=O)C(=O)C=C1O	2406.2	Semi standard non polar	33892256
Topaquinone,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(=O)O	2437.4	Semi standard non polar	33892256
Topaquinone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C(C)(C)C	2712.7	Semi standard non polar	33892256
Topaquinone,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O	2726.8	Semi standard non polar	33892256
Topaquinone,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(=O)O[Si](C)(C)C(C)(C)C	2687.9	Semi standard non polar	33892256
Topaquinone,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC(=O)C(=O)C=C1O)C(=O)O)[Si](C)(C)C(C)(C)C	2766.5	Semi standard non polar	33892256
Topaquinone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2965.4	Semi standard non polar	33892256
Topaquinone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	2784.8	Standard non polar	33892256
Topaquinone,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	3328.5	Standard polar	33892256
Topaquinone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3084.0	Semi standard non polar	33892256
Topaquinone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2846.1	Standard non polar	33892256
Topaquinone,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@@H](C(=O)O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3364.3	Standard polar	33892256
Topaquinone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3026.5	Semi standard non polar	33892256
Topaquinone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2949.0	Standard non polar	33892256
Topaquinone,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3367.5	Standard polar	33892256
Topaquinone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3335.9	Semi standard non polar	33892256
Topaquinone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3065.8	Standard non polar	33892256
Topaquinone,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C(C)(C)C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3276.7	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
beta-Alanine metabolism	Not Available
GABA-Transaminase Deficiency		Not Available
Ureidopropionase Deficiency		Not Available
Carnosinuria, carnosinemia		Not Available
Tyrosine 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

FDB028336

KNApSAcK ID

Not Available

Chemspider ID

110408

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Topaquinone

METLIN ID

Not Available

PubChem Compound

123871

PDB ID

Not Available

ChEBI ID

36076

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

Klinman JP: The multi-functional topa-quinone copper amine oxidases. Biochim Biophys Acta. 2003 Apr 11;1647(1-2):131-7. [PubMed:12686122 ]

Enzymes

Enzyme Details

1. Amiloride-sensitive amine oxidase [copper-containing]

General function:: Involved in copper ion binding
Specific function:: Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:: ABP1
Uniprot ID:: P19801
Molecular weight:: 85377.1

Enzyme Details

2. Membrane primary amine oxidase

General function:: Involved in copper ion binding
Specific function:: Cell adhesion protein that participates in lymphocyte recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-independent fashion. Has a monoamine oxidase activity. May play a role in adipogenesis.
Gene Name:: AOC3
Uniprot ID:: Q16853
Molecular weight:: 84621.27

Enzyme Details

3. Retina-specific copper amine oxidase

General function:: Involved in copper ion binding
Specific function:: Has a monoamine oxidase activity with substrate specificity for 2-phenylethylamine and tryptamine. May play a role in adipogenesis. May be a critical modulator of signal transmission in retina.
Gene Name:: AOC2
Uniprot ID:: O75106
Molecular weight:: 80515.11

Showing metabocard for Topaquinone (HMDB0011639)

MOL for HMDB0011639 (Topaquinone)

3D MOL for HMDB0011639 (Topaquinone)

3D SDF for HMDB0011639 (Topaquinone)

3D-SDF for HMDB0011639 (Topaquinone)

PDB for HMDB0011639 (Topaquinone)

3D PDB for HMDB0011639 (Topaquinone)

SMILES for HMDB0011639 (Topaquinone)

INCHI for HMDB0011639 (Topaquinone)

Structure for HMDB0011639 (Topaquinone)

3D Structure for HMDB0011639 (Topaquinone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes