Showing metabocard for Melanin (BMDB0004068)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
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Record Information
Version1.0
Creation Date2016-09-30 23:07:36 UTC
Update Date2020-05-21 16:28:46 UTC
BMDB IDBMDB0004068
Secondary Accession Numbers
  • BMDB04068
Metabolite Identification
Common NameMelanin
DescriptionMelanin, also known as melanin, belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings. Melanin is possibly soluble (in water) and a moderately basic compound (based on its pKa). Melanin can be biosynthesized from 5,6-dihydroxyindole-2-carboxylic acid through its interaction with the enzyme tyrosinase. In cattle, melanin is involved in the metabolic pathway called the tyrosine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AllomelaninsHMDB
MelaninsHMDB
PhaeomelaninsHMDB
Chemical FormulaC18H10N2O4
Average Molecular Weight318.283
Monoisotopic Molecular Weight318.064056818
IUPAC Name6,14-dimethyl-4,12-diazapentacyclo[8.6.1.1²,⁵.0¹³,¹⁷.0⁹,¹⁸]octadeca-1(17),2,5,9(18),10,13-hexaene-7,8,15,16-tetrone
Traditional Namemelanin
CAS Registry Number8049-97-6
SMILES
CC1=C2NC=C3C2=C(C2=CNC4=C(C)C(=O)C(=O)C3=C24)C(=O)C1=O
InChI Identifier
InChI=1S/C18H10N2O4/c1-5-13-9-7(3-19-13)12-10-8(11(9)17(23)15(5)21)4-20-14(10)6(2)16(22)18(12)24/h3-4,19-20H,1-2H3
InChI KeyXUMBMVFBXHLACL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as anthracenes. These are organic compounds containing a system of three linearly fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassAnthracenes
Sub ClassNot Available
Direct ParentAnthracenes
Alternative Parents
Substituents
  • Anthracene
  • Indolequinone
  • Indole
  • Indole or derivatives
  • Isoindole
  • Isoindole or derivatives
  • Quinone
  • Vinylogous amide
  • Pyrrole
  • Heteroaromatic compound
  • Cyclic ketone
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Myelin sheath
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.76ALOGPS
logP-0.27ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)12.65ChemAxon
pKa (Strongest Basic)1.34ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.34 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.28 m³·mol⁻¹ChemAxon
Polarizability31.77 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ku-0094000000-94704d5e412ed2489f17View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-ca3bb49729033ec75f80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-0089000000-bc7ad58775b231f90e84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-0090000000-dc286795a5fc4078c357View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-80dff8e14771680560aaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0019000000-395c4a7d06b442e4dcf1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06ri-0091000000-760c7a558bb6db841316View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-4e47ddd4efc907375a4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-2c08c7c7a9e445b436e4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07ci-0091000000-438444e04c7ab334b33aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-92cfd0e072e19008dfb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009000000-92cfd0e072e19008dfb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0092000000-a9de3724b70ffcb23cf8View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Myelin sheath
Biospecimen Locations
  • Adrenal Gland
  • Adrenal Medulla
  • Bladder
  • Epidermis
  • Fibroblasts
  • Hair
  • Neuron
  • Spleen
  • Thyroid Gland
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0004068
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023298
KNApSAcK IDNot Available
Chemspider ID4884931
KEGG Compound IDC05606
BioCyc IDNot Available
BiGG ID46115
Wikipedia LinkMelanin
METLIN ID7011
PubChem Compound6325610
PDB IDNot Available
ChEBI ID89634
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Tyrosinase
General function:
Involved in copper ion binding
Specific function:
This is a copper-containing oxidase that functions in the formation of pigments such as melanins and other polyphenolic compounds. Catalyzes the initial and rate limiting step in the cascade of reactions leading to melanin production from tyrosine. In addition to hydroxylating tyrosine to DOPA (3,4-dihydroxyphenylalanine), also catalyzes the oxidation of DOPA to DOPA-quinone, and possibly the oxidation of DHI (5,6-dihydroxyindole) to indole-5,6 quinone.
Gene Name:
TYR
Uniprot ID:
Q8MIU0
Molecular weight:
60304.0
Reactions
2 5,6-Dihydroxyindole-2-carboxylic acid + Oxygen → Melanin + Waterdetails