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Record Information
Version2.0
Created at2022-05-11 18:25:38 UTC
Updated at2022-05-11 18:25:38 UTC
NP-MRD IDNP0090905
Secondary Accession NumbersNone
Natural Product Identification
Common Name11-beta-Hydroxyandrosterone-3-glucuronide
Description6-Hydroxymelatonin, also known as lopac-H-0627, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 6-Hydroxymelatonin is an extremely weak basic (essentially neutral) compound (based on its pKa). 6-Hydroxymelatonin exists in all living organisms, ranging from bacteria to humans. 6-Hydroxymelatonin can be biosynthesized from melatonin; which is catalyzed by the enzyme cytochrome P450 1A1. In humans, 6-hydroxymelatonin is involved in tryptophan metabolism. Outside of the human body, 6-Hydroxymelatonin has been detected, but not quantified in, several different foods, such as lemon grass, papaya, corianders, sparkleberries, and wax gourds. This could make 6-hydroxymelatonin a potential biomarker for the consumption of these foods. It is also an antioxidant and neuroprotective, and is even more potent in this regard relative to melatonin. Similar to melatonin, 6-OHM is a full agonist of the MT1 and MT2 receptors. 11-beta-Hydroxyandrosterone-3-glucuronide was first documented in 1985 (PMID: 3964785). 6-Hydroxymelatonin (6-OHM) is a naturally occurring, endogenous, major active metabolite of melatonin (PMID: 15356035) (PMID: 16300638) (PMID: 22430231) (PMID: 2646423).
Structure
Thumb
Synonyms
ValueSource
Lopac-H-0627ChEBI
6-OxymelatoninHMDB
6-Hydroxy-N-acetyl-5-methoxytryptamineHMDB
11-beta-Hydroxyetiocholanolone-3-glucuronideHMDB
11beta-Hydroxyandrosterone 3-glucuronideHMDB
11-b-Hydroxyandrosterone-3-glucuronideGenerator
11-Β-hydroxyandrosterone-3-glucuronideGenerator
Chemical FormulaC25H38O9
Average Mass482.5638 Da
Monoisotopic Mass482.25158 Da
IUPAC Name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7S,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}oxane-2-carboxylic acid
Traditional Name(2S,3S,4S,5R,6R)-3,4,5-trihydroxy-6-{[(1S,2S,5R,7S,10S,11S,15S,17S)-17-hydroxy-2,15-dimethyl-14-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-yl]oxy}oxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
[H][C@@]12CCC(=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CC[C@@]2([H])C[C@@H](CC[C@]12C)O[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)C(O)=O
InChI Identifier
InChI=1S/C25H38O9/c1-24-8-7-12(33-23-20(30)18(28)19(29)21(34-23)22(31)32)9-11(24)3-4-13-14-5-6-16(27)25(14,2)10-15(26)17(13)24/h11-15,17-21,23,26,28-30H,3-10H2,1-2H3,(H,31,32)/t11-,12+,13-,14-,15-,17+,18-,19-,20+,21-,23+,24-,25-/m0/s1
InChI KeyBRPLOVMHAFXVOQ-HUMIJZDLSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassHydroxyindoles
Direct ParentHydroxyindoles
Alternative Parents
Substituents
  • Hydroxyindole
  • 3-alkylindole
  • Indole
  • Anisole
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Ether
  • Carboximidic acid derivative
  • Carboximidic acid
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP0.8ALOGPS
logP1.01ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)3.47ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area153.75 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity117.68 m³·mol⁻¹ChemAxon
Polarizability50.35 ųChemAxon
Number of Rings5ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0004081
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023304
KNApSAcK IDNot Available
Chemspider ID1794
KEGG Compound IDC05643
BioCyc IDCPD-12014
BiGG ID46185
Wikipedia Link6-Hydroxymelatonin
METLIN ID7013
PubChem Compound1864
PDB IDNot Available
ChEBI ID2198
Good Scents IDNot Available
References
General References
  1. Frisch H, Waldhauser F, Waldhor T, Mullner-Eidenbock A, Neupane P, Schweitzer K: Increase in 6-hydroxymelatonin excretion in humans during ascent to high altitudes. J Clin Endocrinol Metab. 2004 Sep;89(9):4388-90. doi: 10.1210/jc.2003-032214. [PubMed:15356035 ]
  2. Maharaj DS, Maharaj H, Daya S, Glass BD: Melatonin and 6-hydroxymelatonin protect against iron-induced neurotoxicity. J Neurochem. 2006 Jan;96(1):78-81. doi: 10.1111/j.1471-4159.2005.03532.x. Epub 2005 Nov 21. [PubMed:16300638 ]
  3. Ozkan E, Yaman H, Cakir E, Deniz O, Oztosun M, Gumus S, Akgul EO, Agilli M, Cayci T, Kurt YG, Aydin I, Arslan Y, Ilhan N, Ilhan N, Erbil MK: Plasma melatonin and urinary 6-hydroxymelatonin levels in patients with pulmonary tuberculosis. Inflammation. 2012 Aug;35(4):1429-34. doi: 10.1007/s10753-012-9456-3. [PubMed:22430231 ]
  4. Neville S, Arendt J, Ioannides C: A study of the mutagenicity of melatonin and 6-hydroxymelatonin. J Pineal Res. 1989;6(1):73-6. doi: 10.1111/j.1600-079x.1989.tb00404.x. [PubMed:2646423 ]
  5. Young IM, Leone RM, Francis P, Stovell P, Silman RE: Melatonin is metabolized to N-acetyl serotonin and 6-hydroxymelatonin in man. J Clin Endocrinol Metab. 1985 Jan;60(1):114-9. doi: 10.1210/jcem-60-1-114. [PubMed:3964785 ]