NP-MRD: Showing NP-Card for 6-Hydroxymelatonin (NP0087136)

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Record Information

Version

2.0

Created at

2022-05-11 16:41:07 UTC

Updated at

2022-05-11 16:41:07 UTC

NP-MRD ID

NP0087136

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-Hydroxymelatonin

Description

6-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 beans, new zealand spinachs, ginsengs, mountain yams, and scarlet beans. This could make 6-hydroxymelatonin a potential biomarker for the consumption of these foods. Similar to melatonin, 6-OHM is a full agonist of the MT1 and MT2 receptors. It is also an antioxidant and neuroprotective, and is even more potent in this regard relative to melatonin. 6-Hydroxymelatonin is found in Mus musculus. 6-Hydroxymelatonin was first documented in 1987 (PMID: 3035087). 6-Hydroxymelatonin (6-OHM) is a naturally occurring, endogenous, major active metabolite of melatonin (PMID: 15356035) (PMID: 16300638) (PMID: 22430231) (PMID: 3608151) (PMID: 7562371) (PMID: 3436070).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.7185    2.7790    0.9278 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3943    1.5561    0.8842 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8714    0.3827    0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5984    0.2610   -0.1271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1442   -0.9654   -0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0606   -1.3502   -1.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2410   -0.4869   -1.4020 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0040   -0.2014   -0.1399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1323    0.6459   -0.4471 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0491    1.0893    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2014    1.9564    0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8660    0.7272    1.7417 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0412   -2.6888   -1.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2575   -3.1536   -1.1047 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9280   -2.0978   -0.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2058   -1.9723   -0.0627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6495   -0.7565    0.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9461   -0.6603    0.9313 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559    2.9083    0.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2463    2.9315    1.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5100    3.5825    0.8611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9792    1.1401   -0.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8921   -0.9325   -2.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8524    0.4972   -1.7630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4010    0.2640    0.6412 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3665   -1.1771    0.2974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2815    0.9420   -1.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5798    2.4779    1.1271 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8232    2.7451   -0.4680 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9581    1.3400   -0.2831 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7056   -3.3299   -1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5985   -4.1404   -1.2187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8038   -2.8699   -0.0550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5664   -1.4435    0.9753 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 17  2  0
 17 18  1  0
 17 16  1  0
 16 15  2  0
 15 14  1  0
 14 13  1  0
 13  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  5 15  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
 18 34  1  0
 16 33  1  0
 14 32  1  0
 13 31  1  0
  7 23  1  0
  7 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
  4 22  1  0
M  END


  Mrv0541 02231219522D          

 18 19  0  0  0  0            999 V2000
   25.6576  -12.0198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6576  -13.6699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2599  -10.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9016  -10.4424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.5817  -13.5087    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.6454  -11.2266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8381  -11.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6576  -11.1948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9652   -9.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7089  -10.2723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3721  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3721  -12.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8011  -13.2574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5817  -12.1809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8011  -12.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0632  -12.8449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0867  -13.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0867  -12.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  1 12  1  0  0  0  0
  2 11  1  0  0  0  0
  3 10  2  0  0  0  0
  4  6  1  0  0  0  0
  4 10  1  0  0  0  0
  5 13  1  0  0  0  0
  5 16  1  0  0  0  0
  6  7  1  0  0  0  0
  7 14  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 11 17  1  0  0  0  0
 12 18  1  0  0  0  0
 13 15  1  0  0  0  0
 13 17  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 15 18  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0087136

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)

> <INCHI_KEY>
OMYMRCXOJJZYKE-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O3

> <MOLECULAR_WEIGHT>
248.2777

> <EXACT_MASS>
248.116092388

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.646859447844083

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

> <ALOGPS_LOGP>
0.80

> <JCHEM_LOGP>
0.8440474656666671

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.88686461347585

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.293899803560572

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9409566074830477

> <JCHEM_POLAR_SURFACE_AREA>
74.35

> <JCHEM_REFRACTIVITY>
68.26080000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.73e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      47.894 -22.437   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      47.894 -25.517   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      58.352 -20.321   0.000  0.00  0.00           O+0
HETATM    4  N   UNK     0      55.816 -19.492   0.000  0.00  0.00           N+0
HETATM    5  N   UNK     0      53.353 -25.216   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      55.338 -20.956   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      53.831 -21.274   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      47.894 -20.897   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      57.802 -17.711   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      57.323 -19.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      49.228 -24.747   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      49.228 -23.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      51.895 -24.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      53.353 -22.738   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      51.895 -23.207   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      54.251 -23.977   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      50.562 -25.517   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      50.562 -22.437   0.000  0.00  0.00           C+0
CONECT    1    8   12                                                       
CONECT    2   11                                                            
CONECT    3   10                                                            
CONECT    4    6   10                                                       
CONECT    5   13   16                                                       
CONECT    6    4    7                                                       
CONECT    7    6   14                                                       
CONECT    8    1                                                            
CONECT    9   10                                                            
CONECT   10    3    4    9                                                  
CONECT   11    2   12   17                                                  
CONECT   12    1   11   18                                                  
CONECT   13    5   15   17                                                  
CONECT   14    7   15   16                                                  
CONECT   15   13   14   18                                                  
CONECT   16    5   14                                                       
CONECT   17   11   13                                                       
CONECT   18   12   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
Lopac-H-0627	ChEBI
6-Oxymelatonin	HMDB
6-Hydroxy-N-acetyl-5-methoxytryptamine	HMDB
6-Hydroxy-N-acetyl-5-methoxytryptamine	HMDB

Chemical Formula

C₁₃H₁₆N₂O₃

Average Mass

248.2777 Da

Monoisotopic Mass

248.11609 Da

IUPAC Name

N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

Traditional Name

N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C2NC=C(CCNC(C)=O)C2=C1

InChI Identifier

InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)

InChI Key

OMYMRCXOJJZYKE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Hydroxyindoles

Direct Parent

Hydroxyindoles

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

acetamides (CHEBI:2198 )
tryptamines (CHEBI:2198 )
a small molecule (CPD-12014 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	0.8	ALOGPS
logP	0.84	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	9.29	ChemAxon
pKa (Strongest Basic)	-0.94	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	74.35 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.26 m³·mol⁻¹	ChemAxon
Polarizability	26.65 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0004081

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023304

KNApSAcK ID

Not Available

Chemspider ID

1794

KEGG Compound ID

C05643

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

2198

Good Scents ID

Not Available

References

General References

Higa S, Suzuki T, Sakoda S, Kishimoto S, Takaba Y, Nakajima A, Markey SP: Disturbed function of the pineal gland in familial amyloid polyneuropathy. J Neural Transm. 1987;69(1-2):97-103. [PubMed:3035087 ]
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 ]
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 ]
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Showing NP-Card for 6-Hydroxymelatonin (NP0087136)

MOL for NP0087136 (6-Hydroxymelatonin)

3D MOL for NP0087136 (6-Hydroxymelatonin)

3D SDF for NP0087136 (6-Hydroxymelatonin)

3D-SDF for NP0087136 (6-Hydroxymelatonin)

PDB for NP0087136 (6-Hydroxymelatonin)

3D PDB for NP0087136 (6-Hydroxymelatonin)

SMILES for NP0087136 (6-Hydroxymelatonin)

INCHI for NP0087136 (6-Hydroxymelatonin)

Structure for NP0087136 (6-Hydroxymelatonin)

3D Structure for NP0087136 (6-Hydroxymelatonin)