NP-MRD: Showing NP-Card for 5-Hydroxytryptophol glucuronide (NP0339210)

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Record Information

Version

2.0

Created at

2024-09-11 20:25:52 UTC

Updated at

2024-09-11 20:25:52 UTC

NP-MRD ID

NP0339210

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-Hydroxytryptophol glucuronide

Description

5-Hydroxytryptophol glucuronide belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose. 5-Hydroxytryptophol glucuronide was first documented in 2005 (PMID: 15664340). 5-Hydroxytryptophol glucuronide is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 17112495).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016502D          

 24 26  0  0  1  0            999 V2000
    8.8497  -11.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2623  -10.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9199  -11.6282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7484  -12.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0873  -11.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3930  -10.2556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3067  -11.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2623  -11.9621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4998  -11.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0873  -10.5332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6393   -9.9200    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3615  -12.9872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8497  -12.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0247  -12.6766    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.6122  -13.3911    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.6122  -11.9621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7872  -13.3911    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.7872  -11.9621    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3747  -12.6766    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.0247  -14.1056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3747  -14.1056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5497  -12.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3747  -11.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5497  -11.2476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  8  1  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  3  7  1  0  0  0  0
  4 12  1  0  0  0  0
  5  8  2  0  0  0  0
  5  9  1  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 15 14  1  0  0  0  0
 16 14  1  0  0  0  0
 14 13  1  6  0  0  0
 17 15  1  0  0  0  0
 15 20  1  6  0  0  0
 18 16  1  0  0  0  0
 19 17  1  0  0  0  0
 17 21  1  1  0  0  0
 19 18  1  0  0  0  0
 18 23  1  1  0  0  0
 19 22  1  6  0  0  0
 24 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339210

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCC1=CNC2=C1C=C(O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H21NO7/c18-4-3-8-6-17-11-2-1-9(5-10(8)11)23-16-15(22)14(21)13(20)12(7-19)24-16/h1-2,5-6,12-22H,3-4,7H2/t12-,13-,14+,15-,16+/m1/s1

> <INCHI_KEY>
MYNVMBICAGQOMG-LJIZCISZSA-N

> <FORMULA>
C16H21NO7

> <MOLECULAR_WEIGHT>
339.3404

> <EXACT_MASS>
339.131802031

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.06385840878856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,4S,5S,6R)-2-{[3-(2-hydroxyethyl)-1H-indol-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
-0.52

> <JCHEM_LOGP>
-0.9783141683333337

> <ALOGPS_LOGS>
-1.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.19517607104024

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200038358303017

> <JCHEM_PKA_STRONGEST_BASIC>
-2.4305488307638896

> <JCHEM_POLAR_SURFACE_AREA>
135.4

> <JCHEM_REFRACTIVITY>
82.8407

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.05e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,4S,5S,6R)-2-{[3-(2-hydroxyethyl)-1H-indol-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      16.519 -20.996   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.290 -19.662   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.250 -21.706   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.930 -23.212   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      18.830 -22.329   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      21.267 -19.144   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      21.106 -20.675   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.290 -22.329   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.600 -20.996   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.830 -19.662   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0      19.860 -18.517   0.000  0.00  0.00           N+0
HETATM   12  O   UNK     0      23.075 -24.243   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      16.519 -23.663   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      14.979 -23.663   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.209 -24.997   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      14.209 -22.329   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      12.669 -24.997   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.669 -22.329   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.899 -23.663   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      14.979 -26.330   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      11.899 -26.330   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.359 -23.663   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      11.899 -20.996   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.359 -20.996   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1   10                                                       
CONECT    3    4    7                                                       
CONECT    4    3   12                                                       
CONECT    5    8    9                                                       
CONECT    6    7   11                                                       
CONECT    7    3    6    9                                                  
CONECT    8    1    5   13                                                  
CONECT    9    5    7   10                                                  
CONECT   10    2    9   11                                                  
CONECT   11    6   10                                                       
CONECT   12    4                                                            
CONECT   13    8   14                                                       
CONECT   14   15   16   13                                                  
CONECT   15   14   17   20                                                  
CONECT   16   14   18                                                       
CONECT   17   15   19   21                                                  
CONECT   18   16   19   23                                                  
CONECT   19   17   18   22                                                  
CONECT   20   15                                                            
CONECT   21   17                                                            
CONECT   22   19                                                            
CONECT   23   18   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Value	Source
5 Hydroxytryptophol glucuronide	HMDB
5-Hydroxytryptophol glucuronide	MeSH

Chemical Formula

C₁₆H₂₁NO₇

Average Mass

339.3404 Da

Monoisotopic Mass

339.13180 Da

IUPAC Name

(2R,3R,4S,5S,6R)-2-{[3-(2-hydroxyethyl)-1H-indol-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

(2R,3R,4S,5S,6R)-2-{[3-(2-hydroxyethyl)-1H-indol-5-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

OCCC1=CNC2=C1C=C(O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C=C2

InChI Identifier

InChI=1S/C16H21NO7/c18-4-3-8-6-17-11-2-1-9(5-10(8)11)23-16-15(22)14(21)13(20)12(7-19)24-16/h1-2,5-6,12-22H,3-4,7H2/t12-,13-,14+,15-,16+/m1/s1

InChI Key

MYNVMBICAGQOMG-LJIZCISZSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans, and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-Fructose, and L rhamnose.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Phenolic glycosides

Alternative Parents

Substituents

Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
3-alkylindole
Indole
Indole or derivatives
Monosaccharide
Oxane
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Secondary alcohol
Polyol
Azacycle
Oxacycle
Acetal
Organoheterocyclic compound
Alcohol
Primary alcohol
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	-0.52	ALOGPS
logP	-0.98	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-2.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	135.4 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.84 m³·mol⁻¹	ChemAxon
Polarizability	34.06 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013200

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029328

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481648

PDB ID

Not Available

ChEBI ID

32649

Good Scents ID

Not Available

References

General References

Stephanson N, Dahl H, Helander A, Beck O: Determination of urinary 5-hydroxytryptophol glucuronide by liquid chromatography-mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Feb 25;816(1-2):107-12. doi: 10.1016/j.jchromb.2004.11.026. [PubMed:15664340 ]
Dierkes J, Wolfersdorf M, Borucki K, Weinmann W, Wiesbeck G, Beck O, Borg S, Wurst FM: Determination of glucuronidated 5-hydroxytryptophol (GTOL), a marker of recent alcohol intake, by ELISA technique. Clin Biochem. 2007 Jan;40(1-2):128-31. doi: 10.1016/j.clinbiochem.2006.10.010. Epub 2006 Oct 20. [PubMed:17112495 ]

Showing NP-Card for 5-Hydroxytryptophol glucuronide (NP0339210)

MOL for NP0339210 (5-Hydroxytryptophol glucuronide)

3D MOL for NP0339210 (5-Hydroxytryptophol glucuronide)

3D SDF for NP0339210 (5-Hydroxytryptophol glucuronide)

3D-SDF for NP0339210 (5-Hydroxytryptophol glucuronide)

PDB for NP0339210 (5-Hydroxytryptophol glucuronide)

3D PDB for NP0339210 (5-Hydroxytryptophol glucuronide)

SMILES for NP0339210 (5-Hydroxytryptophol glucuronide)

INCHI for NP0339210 (5-Hydroxytryptophol glucuronide)

Structure for NP0339210 (5-Hydroxytryptophol glucuronide)

3D Structure for NP0339210 (5-Hydroxytryptophol glucuronide)