NP-MRD: Showing NP-Card for 2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid (NP0204432)

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Record Information

Version

2.0

Created at

2022-09-05 00:06:11 UTC

Updated at

2022-09-05 00:06:11 UTC

NP-MRD ID

NP0204432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid

Description

2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid is found in Garcinia dulcis, Lonicera caerulea, Prunus mume and Tagetes patula.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309272007352D          

 15 14  0  0  0  0            999 V2000
 2500.0020 2500.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7169 2500.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4318 2500.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2502.1468 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2502.8617 2500.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2501.4318 2499.5882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2871 2500.8255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5722 2500.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2497.8552 2500.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2497.1382 2500.4117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2498.5722 2499.5882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0020 2499.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 2500.7169 2499.1744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2499.2871 2499.1744    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 2500.0020 2501.2387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  6  2  0  0  0  0
  4  5  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 11  2  0  0  0  0
  9 10  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0204432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC(O)(CC(=O)OC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H12O7/c1-14-5(9)3-8(13,7(11)12)4-6(10)15-2/h13H,3-4H2,1-2H3,(H,11,12)

> <INCHI_KEY>
XLYPVOJLUJUWKA-UHFFFAOYSA-N

> <FORMULA>
C8H12O7

> <MOLECULAR_WEIGHT>
220.177

> <EXACT_MASS>
220.058302726

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
19.55718543871535

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid

> <ALOGPS_LOGP>
-0.68

> <JCHEM_LOGP>
-1.03089934

> <ALOGPS_LOGS>
-0.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.347594523707244

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3240097428133266

> <JCHEM_PKA_STRONGEST_BASIC>
-4.1860065322612074

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
45.1621

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    4666.6704667.439   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    4668.0054668.208   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    4669.3394667.439   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    4670.6744668.208   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    4672.0094667.439   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    4669.3394665.898   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    4665.3364668.208   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    4664.0014667.439   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    4662.6634668.208   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    4661.3254667.435   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    4664.0014665.898   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0    4666.6704665.898   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    4668.0054665.126   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0    4665.3364665.126   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0    4666.6704668.979   0.000  0.00  0.00           O+0
CONECT    1    2    7   12   15                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8                                                            
CONECT   12    1   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
1,5-Dimethyl citric acid	Generator
2-Hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoate	Generator
sym-Dimethyl citrate	PhytoBank
alpha,alpha'-Dimethyl citrate	PhytoBank
α,α'-Dimethyl citrate	PhytoBank
α,α’-Dimethyl citrate	PhytoBank
2-Hydroxy-1,2,3-propanetricarboxylic acid-1,3-dimethylester	PhytoBank
2-Hydroxy-1,2,3-propanetricarboxylic acid 1,3-dimethyl ester	PhytoBank

Chemical Formula

C₈H₁₂O₇

Average Mass

220.1770 Da

Monoisotopic Mass

220.05830 Da

IUPAC Name

2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid

Traditional Name

2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid

CAS Registry Number

Not Available

SMILES

COC(=O)CC(O)(CC(=O)OC)C(O)=O

InChI Identifier

InChI=1S/C8H12O7/c1-14-5(9)3-8(13,7(11)12)4-6(10)15-2/h13H,3-4H2,1-2H3,(H,11,12)

InChI Key

XLYPVOJLUJUWKA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Garcinia dulcis	LOTUS Database	35616633
Lonicera caerulea	LOTUS Database	35616633
Prunus mume	LOTUS Database	35616633
Tagetes patula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acid methyl ester
Alpha-hydroxy acid
Hydroxy acid
Fatty acyl
Methyl ester
Tertiary alcohol
Carboxylic acid ester
Carboxylic acid
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	-0.68	ALOGPS
logP	-1	ChemAxon
logS	-0.15	ALOGPS
pKa (Strongest Acidic)	3.32	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	45.16 m³·mol⁻¹	ChemAxon
Polarizability	19.56 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB093570

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

12566214

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid (NP0204432)

MOL for NP0204432 (2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid)

3D MOL for NP0204432 (2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid)

3D SDF for NP0204432 (2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid)

3D-SDF for NP0204432 (2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid)

PDB for NP0204432 (2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid)

3D PDB for NP0204432 (2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid)

SMILES for NP0204432 (2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid)

INCHI for NP0204432 (2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid)

Structure for NP0204432 (2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid)

3D Structure for NP0204432 (2-hydroxy-4-methoxy-2-(2-methoxy-2-oxoethyl)-4-oxobutanoic acid)