NP-MRD: Showing NP-Card for 3-Methoxy-4-hydroxyphenylglycolaldehyde (NP0087126)

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Record Information

Version

2.0

Created at

2022-05-11 16:40:50 UTC

Updated at

2022-05-11 16:40:50 UTC

NP-MRD ID

NP0087126

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-Methoxy-4-hydroxyphenylglycolaldehyde

Description

3-Methoxy-4-hydroxyphenylglycolaldehyde, also known as 4-hydroxy-3-methoxy mandelaldehyde, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 3-Methoxy-4-hydroxyphenylglycolaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methoxy-4-hydroxyphenylglycolaldehyde is the monoamine oxidase (MAO) aldehyde metabolite of metanephrine. 3-Methoxy-4-hydroxyphenylglycolaldehyde exists in all living organisms, ranging from bacteria to humans. Within humans, 3-methoxy-4-hydroxyphenylglycolaldehyde participates in a number of enzymatic reactions. In particular, 3-methoxy-4-hydroxyphenylglycolaldehyde can be biosynthesized from normetanephrine; which is mediated by the enzyme amine oxidase [flavin-containing] a. In addition, 3-methoxy-4-hydroxyphenylglycolaldehyde can be biosynthesized from metanephrine through the action of the enzyme amine oxidase [flavin-containing] a. Metanephrine is an O-methylated metabolite formed by catechol-O-methyltransferase (COMT) from epinephrine. In humans, 3-methoxy-4-hydroxyphenylglycolaldehyde is involved in the metabolic disorder called the monoamine oxidase-a deficiency (mao-a) pathway. Outside of the human body, 3-Methoxy-4-hydroxyphenylglycolaldehyde has been detected, but not quantified in, several different foods, such as chervils, kai-lans, calabash, custard apples, and tea. This could make 3-methoxy-4-hydroxyphenylglycolaldehyde a potential biomarker for the consumption of these foods. Catecholamines are substantially increased during stress, exercise or smoking and could result in clinically important platelet activation if their action was not rapidly regulated. Catecholamines play an important role in platelet activation and aggregation, epinephrine being the most potent one. The inhibitory effects of methoxy phenolic derivatives on epinephrine-induced platelet aggregation may possibly be attributed to their free radical scavenging properties. There is substantial evidence to conclude that an internal rapid autoregulation of epinephrine-induced platelet aggregation, caused by its metabolic degradation products, takes place in vivo.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02231219522D          

 13 13  0  0  0  0            999 V2000
   27.5218  -11.7090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364   -8.8214    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508  -12.5340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.3797   -9.2339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508   -9.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8073  -11.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6653   -8.8214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364  -11.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508  -11.7090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9508  -10.0589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2364  -10.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6653  -11.2964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6653  -10.4714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  8  1  0  0  0  0
  2  5  1  0  0  0  0
  3  9  1  0  0  0  0
  4  7  2  0  0  0  0
  5  7  1  0  0  0  0
  5 10  1  0  0  0  0
  8  9  2  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 11  2  0  0  0  0
 10 13  1  0  0  0  0
 12 13  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0087126

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=CC(=C1)C(O)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-5,8,11-12H,1H3

> <INCHI_KEY>
VISAJVAPYPFKCL-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
17.671285440421318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde

> <ALOGPS_LOGP>
0.49

> <JCHEM_LOGP>
0.27598280499999994

> <ALOGPS_LOGS>
-1.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.947572767111232

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.903212004669111

> <JCHEM_PKA_STRONGEST_BASIC>
-3.756563475609691

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
46.22250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde

> <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      51.374 -21.857   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      52.708 -16.467   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      54.041 -23.397   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      56.709 -17.237   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      54.041 -17.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      50.040 -21.087   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      55.375 -16.467   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      52.708 -21.087   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      54.041 -21.857   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      54.041 -18.777   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      52.708 -19.547   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      55.375 -21.087   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      55.375 -19.547   0.000  0.00  0.00           C+0
CONECT    1    6    8                                                       
CONECT    2    5                                                            
CONECT    3    9                                                            
CONECT    4    7                                                            
CONECT    5    2    7   10                                                  
CONECT    6    1                                                            
CONECT    7    4    5                                                       
CONECT    8    1    9   11                                                  
CONECT    9    3    8   12                                                  
CONECT   10    5   11   13                                                  
CONECT   11    8   10                                                       
CONECT   12    9   13                                                       
CONECT   13   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol

Synonyms

Value	Source
4-Hydroxy-3-methoxy mandelaldehyde	HMDB
4-Hydroxy-3-methoxymandelaldehyde	HMDB
4-Hydroxy-3-methoxyphenylglycolaldehyde	HMDB
a,4-Dihydroxy-3-methoxy-benzeneacetaldehyde	HMDB

Chemical Formula

C₉H₁₀O₄

Average Mass

182.1733 Da

Monoisotopic Mass

182.05791 Da

IUPAC Name

2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde

Traditional Name

2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetaldehyde

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(=C1)C(O)C=O

InChI Identifier

InChI=1S/C9H10O4/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-5,8,11-12H,1H3

InChI Key

VISAJVAPYPFKCL-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
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 methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Methoxyphenol
Phenylacetaldehyde
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Monocyclic benzene moiety
Alpha-hydroxyaldehyde
Secondary alcohol
Ether
Aromatic alcohol
Organooxygen compound
Aldehyde
Carbonyl group
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

glycolaldehydes (CHEBI:27932 )
a small molecule (CPD-11876 )

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	0.49	ALOGPS
logP	0.28	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	9.9	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	46.22 m³·mol⁻¹	ChemAxon
Polarizability	17.67 Å³	ChemAxon
Number of Rings	1	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

HMDB0004061

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023294

KNApSAcK ID

Not Available

Chemspider ID

389601

KEGG Compound ID

C05583

BioCyc ID

Not Available

BiGG ID

46069

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440729

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3-Methoxy-4-hydroxyphenylglycolaldehyde (NP0087126)

MOL for NP0087126 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

3D MOL for NP0087126 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

3D SDF for NP0087126 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

3D-SDF for NP0087126 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

PDB for NP0087126 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

3D PDB for NP0087126 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

SMILES for NP0087126 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

INCHI for NP0087126 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

Structure for NP0087126 (3-Methoxy-4-hydroxyphenylglycolaldehyde)

3D Structure for NP0087126 (3-Methoxy-4-hydroxyphenylglycolaldehyde)