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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-01-30 15:46:08 UTC
Update Date2021-09-14 15:20:32 UTC
HMDB IDHMDB0011639
Secondary Accession Numbers
  • HMDB11639
Metabolite Identification
Common NameTopaquinone
DescriptionTopaquinone (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
Data?1582752932
Synonyms
ValueSource
(S)-a-Amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoateHMDB
(S)-a-Amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acidHMDB
(S)-alpha-Amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoateHMDB
(S)-alpha-Amino-6-hydroxy-3,4-dioxo-1,5-cyclohexadiene-1-propanoic acidHMDB
2,4,5-Trihydroxyphenylalanine quinoneHMDB
6-Hydroxydopa quinoneHMDB
6-HydroxydopaquinoneHMDB
a-Amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoateHMDB
a-Amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoic acidHMDB
alpha-Amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoateHMDB
alpha-Amino-6-hydroxy-3,4-dioxo-(as)-1,5-cyclohexadiene-1-propanoic acidHMDB
O-TopaquinoneHMDB
Topa quinoneHMDB
TPQHMDB
6-Hydroxydopa quinone, (6-OH-3,4-dioxo)-tautomerHMDB
6-Hydroxyphenylalanine-3,4-dioneHMDB
Chemical FormulaC9H9NO5
Average Molecular Weight211.1715
Monoisotopic Molecular Weight211.048072403
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 Number64192-68-3
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 KeyYWRFBISQAMHSIX-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentL-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 FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Source
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.86 g/LALOGPS
logP-2ALOGPS
logP-2.8ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.73ChemAxon
pKa (Strongest Basic)8.78ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity51.37 m³·mol⁻¹ChemAxon
Polarizability18.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+145.56230932474
DeepCCS[M-H]-143.16730932474
DeepCCS[M-2H]-176.35530932474
DeepCCS[M+Na]+151.53930932474
AllCCS[M+H]+145.632859911
AllCCS[M+H-H2O]+141.632859911
AllCCS[M+NH4]+149.232859911
AllCCS[M+Na]+150.332859911
AllCCS[M-H]-141.932859911
AllCCS[M+Na-2H]-142.232859911
AllCCS[M+HCOO]-142.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TopaquinoneN[C@@H](CC1=CC(=O)C(=O)C=C1O)C(O)=O3209.0Standard polar33892256
TopaquinoneN[C@@H](CC1=CC(=O)C(=O)C=C1O)C(O)=O1737.4Standard non polar33892256
TopaquinoneN[C@@H](CC1=CC(=O)C(=O)C=C1O)C(O)=O2187.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Topaquinone,1TMS,isomer #1C[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@H](N)C(=O)O2213.8Semi standard non polar33892256
Topaquinone,1TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(=O)C(=O)C=C1O2126.5Semi standard non polar33892256
Topaquinone,1TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(=O)O2195.3Semi standard non polar33892256
Topaquinone,2TMS,isomer #1C[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C2258.5Semi standard non polar33892256
Topaquinone,2TMS,isomer #2C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C)C(=O)O2262.1Semi standard non polar33892256
Topaquinone,2TMS,isomer #3C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(=O)O[Si](C)(C)C2190.3Semi standard non polar33892256
Topaquinone,2TMS,isomer #4C[Si](C)(C)N([C@@H](CC1=CC(=O)C(=O)C=C1O)C(=O)O)[Si](C)(C)C2320.1Semi standard non polar33892256
Topaquinone,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C)C(=O)O[Si](C)(C)C2287.2Semi standard non polar33892256
Topaquinone,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C)C(=O)O[Si](C)(C)C2211.7Standard non polar33892256
Topaquinone,3TMS,isomer #1C[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C)C(=O)O[Si](C)(C)C3197.4Standard polar33892256
Topaquinone,3TMS,isomer #2C[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2383.9Semi standard non polar33892256
Topaquinone,3TMS,isomer #2C[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C2272.1Standard non polar33892256
Topaquinone,3TMS,isomer #2C[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@@H](C(=O)O)N([Si](C)(C)C)[Si](C)(C)C3278.1Standard polar33892256
Topaquinone,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O)N([Si](C)(C)C)[Si](C)(C)C2325.7Semi standard non polar33892256
Topaquinone,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O)N([Si](C)(C)C)[Si](C)(C)C2307.2Standard non polar33892256
Topaquinone,3TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](CC1=CC(=O)C(=O)C=C1O)N([Si](C)(C)C)[Si](C)(C)C3296.9Standard polar33892256
Topaquinone,4TMS,isomer #1C[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)C2384.3Semi standard non polar33892256
Topaquinone,4TMS,isomer #1C[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)C2321.7Standard non polar33892256
Topaquinone,4TMS,isomer #1C[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)C3072.0Standard polar33892256
Topaquinone,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(=O)C(=O)C=C1C[C@H](N)C(=O)O2471.2Semi standard non polar33892256
Topaquinone,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(=O)C(=O)C=C1O2406.2Semi standard non polar33892256
Topaquinone,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(=O)O2437.4Semi standard non polar33892256
Topaquinone,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)[C@@H](N)CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C(C)(C)C2712.7Semi standard non polar33892256
Topaquinone,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O[Si](C)(C)C(C)(C)C)C(=O)O2726.8Semi standard non polar33892256
Topaquinone,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)N[C@@H](CC1=CC(=O)C(=O)C=C1O)C(=O)O[Si](C)(C)C(C)(C)C2687.9Semi standard non polar33892256
Topaquinone,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N([C@@H](CC1=CC(=O)C(=O)C=C1O)C(=O)O)[Si](C)(C)C(C)(C)C2766.5Semi standard non polar33892256
Topaquinone,3TBDMS,isomer #1CC(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)C2965.4Semi standard non polar33892256
Topaquinone,3TBDMS,isomer #1CC(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)C2784.8Standard non polar33892256
Topaquinone,3TBDMS,isomer #1CC(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)C3328.5Standard polar33892256
Topaquinone,3TBDMS,isomer #2CC(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)C3084.0Semi standard non polar33892256
Topaquinone,3TBDMS,isomer #2CC(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)C2846.1Standard non polar33892256
Topaquinone,3TBDMS,isomer #2CC(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)C3364.3Standard polar33892256
Topaquinone,3TBDMS,isomer #3CC(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)C3026.5Semi standard non polar33892256
Topaquinone,3TBDMS,isomer #3CC(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)C2949.0Standard non polar33892256
Topaquinone,3TBDMS,isomer #3CC(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)C3367.5Standard polar33892256
Topaquinone,4TBDMS,isomer #1CC(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)C3335.9Semi standard non polar33892256
Topaquinone,4TBDMS,isomer #1CC(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)C3065.8Standard non polar33892256
Topaquinone,4TBDMS,isomer #1CC(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)C3276.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Topaquinone GC-MS (Non-derivatized) - 70eV, Positivesplash10-00kf-4900000000-8000fefca905c692c6bb2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Topaquinone GC-MS (2 TMS) - 70eV, Positivesplash10-006x-9155000000-9f62f7d6a569a845f1912017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Topaquinone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topaquinone 10V, Positive-QTOFsplash10-02tc-0920000000-d016b4dc13ff26872de22017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topaquinone 20V, Positive-QTOFsplash10-014j-1900000000-e9e660167189a0f3df7b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topaquinone 40V, Positive-QTOFsplash10-0gb9-9100000000-e330ba78cb2c450f79af2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topaquinone 10V, Negative-QTOFsplash10-03di-0490000000-10cc522af99cf25fa6072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topaquinone 20V, Negative-QTOFsplash10-03kl-2930000000-faaea6b1c3327a3204042017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topaquinone 40V, Negative-QTOFsplash10-00di-9500000000-8e842526e55c7606e1072017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topaquinone 10V, Positive-QTOFsplash10-03dr-0950000000-5c274a2daa8ac5fdb60f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topaquinone 20V, Positive-QTOFsplash10-000j-1900000000-75224325d6d90326a3ce2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topaquinone 40V, Positive-QTOFsplash10-000i-5900000000-fb2113307dcb393ca87b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topaquinone 10V, Negative-QTOFsplash10-03di-0790000000-264298b854c17cbd06c02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topaquinone 20V, Negative-QTOFsplash10-000i-0900000000-fa2a9a83c16bdc9743e52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Topaquinone 40V, Negative-QTOFsplash10-000i-4900000000-edaf20a2d8ee4a49ed502021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028336
KNApSAcK IDNot Available
Chemspider ID110408
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTopaquinone
METLIN IDNot Available
PubChem Compound123871
PDB IDNot Available
ChEBI ID36076
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Klinman JP: The multi-functional topa-quinone copper amine oxidases. Biochim Biophys Acta. 2003 Apr 11;1647(1-2):131-7. [PubMed:12686122 ]

Enzymes

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
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
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