Melanin (CHEM035626)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:56:18 UTC
Update Date2016-11-09 01:21:20 UTC
Accession NumberCHEM035626
Identification
Common NameMelanin
ClassSmall Molecule
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.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AllomelaninsHMDB
MelaninsHMDB
PhaeomelaninsHMDB
Chemical FormulaC18H10N2O4
Average Molecular Mass318.283 g/mol
Monoisotopic Mass318.064 g/mol
CAS Registry Number8049-97-6
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
SMILESCC1=C2NC=C3C2=C(C2=CNC4=C(C)C(=O)C(=O)C3=C24)C(=O)C1=O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ku-0094000000-94704d5e412ed2489f17Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-ca3bb49729033ec75f80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014l-0089000000-bc7ad58775b231f90e84Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0229-0090000000-dc286795a5fc4078c357Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-80dff8e14771680560aaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0019000000-395c4a7d06b442e4dcf1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06ri-0091000000-760c7a558bb6db841316Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-4e47ddd4efc907375a4fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-0009000000-2c08c7c7a9e445b436e4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-07ci-0091000000-438444e04c7ab334b33aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-92cfd0e072e19008dfb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009000000-92cfd0e072e19008dfb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0092000000-a9de3724b70ffcb23cf8Spectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0004068
FooDB IDFDB023298
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID46115
BioCyc IDNot Available
METLIN ID7011
PDB IDNot Available
Wikipedia LinkMelanin
Chemspider ID4884931
ChEBI ID89634
PubChem Compound ID6325610
Kegg Compound IDC05606
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Pugh ND, Balachandran P, Lata H, Dayan FE, Joshi V, Bedir E, Makino T, Moraes R, Khan I, Pasco DS: Melanin: dietary mucosal immune modulator from Echinacea and other botanical supplements. Int Immunopharmacol. 2005 Apr;5(4):637-47.
2. Borges CR, Roberts JC, Wilkins DG, Rollins DE: Relationship of melanin degradation products to actual melanin content: application to human hair. Anal Biochem. 2001 Mar 1;290(1):116-25.
3. Alaluf S, Atkins D, Barrett K, Blount M, Carter N, Heath A: The impact of epidermal melanin on objective measurements of human skin colour. Pigment Cell Res. 2002 Apr;15(2):119-26.
4. Wenczl E, Van der Schans GP, Roza L, Kolb RM, Timmerman AJ, Smit NP, Pavel S, Schothorst AA: (Pheo)melanin photosensitizes UVA-induced DNA damage in cultured human melanocytes. J Invest Dermatol. 1998 Oct;111(4):678-82.
5. Nielsen KP, Zhao L, Stamnes JJ, Stamnes K, Moan J: The importance of the depth distribution of melanin in skin for DNA protection and other photobiological processes. J Photochem Photobiol B. 2006 Mar 1;82(3):194-8. Epub 2006 Jan 4.
6. Watanabe T, Tamura A, Yoshimura Y, Nakazawa H: Determination of melanin in human hair by photoacoustic spectroscopy. Anal Biochem. 1997 Dec 15;254(2):267-71.
7. Claridge E, Cotton S, Hall P, Moncrieff M: From colour to tissue histology: Physics-based interpretation of images of pigmented skin lesions. Med Image Anal. 2003 Dec;7(4):489-502.
8. Schmidt R, Krien P, Regnier M: The use of diethylaminoethyl-cellulose-membrane filters in a bioassay to quantify melanin synthesis. Anal Biochem. 1996 Mar 15;235(2):113-8.
9. Lu H, Edwards C, Gaskell S, Pearse A, Marks R: Melanin content and distribution in the surface corneocyte with skin phototypes. Br J Dermatol. 1996 Aug;135(2):263-7.
10. Kronstrand R, Forstberg-Peterson S, Kagedal B, Ahlner J, Larson G: Codeine concentration in hair after oral administration is dependent on melanin content. Clin Chem. 1999 Sep;45(9):1485-94.
11. Bartosik J, Wulf HC, Kobayasi T: Melanin and melanosome complexes in long standing stable vitiligo--an ultrastructural study. Eur J Dermatol. 1998 Mar;8(2):95-7.
12. Svensson SP, Lindgren S, Powell W, Green H: Melanin inhibits cytotoxic effects of doxorubicin and daunorubicin in MOLT 4 cells. Pigment Cell Res. 2003 Aug;16(4):351-4.
13. Dwyer T, Muller HK, Blizzard L, Ashbolt R, Phillips G: The use of spectrophotometry to estimate melanin density in Caucasians. Cancer Epidemiol Biomarkers Prev. 1998 Mar;7(3):203-6.
14. Shimada M, Yamada Y, Itoh M, Yatagai T: Melanin and blood concentration in human skin studied by multiple regression analysis: experiments. Phys Med Biol. 2001 Sep;46(9):2385-95.
15. Yamashita T, Kuwahara T, Gonzalez S, Takahashi M: Non-invasive visualization of melanin and melanocytes by reflectance-mode confocal microscopy. J Invest Dermatol. 2005 Jan;124(1):235-40.
16. Huang Z, Zeng H, Hamzavi I, Alajlan A, Tan E, McLean DI, Lui H: Cutaneous melanin exhibiting fluorescence emission under near-infrared light excitation. J Biomed Opt. 2006 May-Jun;11(3):34010.
17. Eng HL, Chen WJ: Melanin-producing medullary carcinoma of the thyroid gland. Arch Pathol Lab Med. 1989 Apr;113(4):377-80.
18. Mammone T, Marenus K, Muizzuddin N, Maes D: Evidence and utility of melanin degrading enzymes. J Cosmet Sci. 2004 Jan-Feb;55(1):116-7.
19. Shimada M, Yamada Y, Itoh M, Yatagai T: Melanin and blood concentration in a human skin model studied by multiple regression analysis: assessment by Monte Carlo simulation. Phys Med Biol. 2001 Sep;46(9):2397-406.
20. Nishidate I, Aizu Y, Mishina H: Depth visualization of a local blood region in skin tissue by use of diffuse reflectance images. Opt Lett. 2005 Aug 15;30(16):2128-30.