NP-MRD: Showing NP-Card for 2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid (NP0201875)

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Record Information

Version

2.0

Created at

2022-09-04 20:59:37 UTC

Updated at

2022-09-04 20:59:38 UTC

NP-MRD ID

NP0201875

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid

Description

2-[(3,4-Dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid is found in Actaea racemosa, Actaea simplex and Piscidia piscipula. 2-[(3,4-Dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 31  0  0  0  0  0  0  0  0999 V2000
    4.0785    1.2206    0.0648 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7913    0.1805    0.6768 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4808   -0.1460    1.8168 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7227   -0.6984    0.1896 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5740   -1.8126    1.0381 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3586   -0.0012    0.1924 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0664    0.3729    1.4997 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -1.0868   -0.1970 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0253   -0.5697   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5812   -0.0352   -1.3863 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8778    0.4463   -1.4201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6785    0.4123   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9912    0.8981   -0.3276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1350   -0.1189    0.8502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9199   -0.1650    1.9929 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8406   -0.5974    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3192    1.1579   -0.6898 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5567    1.0197   -1.9102 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0217    2.4098   -0.1914 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5415   -1.0673    2.2168 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9811   -1.0077   -0.8425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4178   -2.6140    0.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8523    0.8988    1.8196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4855   -1.8949    0.5556 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6818   -1.5267   -1.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9716   -0.0006   -2.2696 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3163    0.8676   -2.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3528    1.2804   -1.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8539    0.1684    2.0147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4148   -1.0147    1.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6679    3.0239    0.2664 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
  4  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  2  0
  6 17  1  0
 17 19  1  0
 17 18  2  0
 16  9  1  0
  5 22  1  0
  4 21  1  6
  3 20  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
 10 26  1  0
 11 27  1  0
 13 28  1  0
 15 29  1  0
 16 30  1  0
 19 31  1  0
M  END


  Mrv1533004241512422D          

 19 19  0  0  0  0            999 V2000
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    1.7605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.1895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.9039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  2  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  9 16  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0201875

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(C(O)=O)C(O)(CC1=CC=C(O)C(O)=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O8/c12-6-2-1-5(3-7(6)13)4-11(19,10(17)18)8(14)9(15)16/h1-3,8,12-14,19H,4H2,(H,15,16)(H,17,18)

> <INCHI_KEY>
PHFSBARLASYIFM-UHFFFAOYSA-N

> <FORMULA>
C11H12O8

> <MOLECULAR_WEIGHT>
272.209

> <EXACT_MASS>
272.053217346

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.911693037773993

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid

> <ALOGPS_LOGP>
0.48

> <JCHEM_LOGP>
-0.34683827833333347

> <ALOGPS_LOGS>
-1.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.478309639175053

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.9939954510183995

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3986610823586405

> <JCHEM_POLAR_SURFACE_AREA>
155.52

> <JCHEM_REFRACTIVITY>
59.50750000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.20e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.001   5.390   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -2.667   3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.770   3.286   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.770   5.954   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.310   5.954   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.000   7.287   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7    8   17                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9                                                       
CONECT   17    6   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

View in JSmol

Synonyms

Value	Source
2-[(3,4-Dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioate	Generator
rac-Fukiic acid	ChEMBL
rac-Fukiate	Generator
3,4-Dihydroxybenzyltartarate	Generator

Chemical Formula

C₁₁H₁₂O₈

Average Mass

272.2090 Da

Monoisotopic Mass

272.05322 Da

IUPAC Name

2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid

Traditional Name

2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid

CAS Registry Number

Not Available

SMILES

OC(C(O)=O)C(O)(CC1=CC=C(O)C(O)=C1)C(O)=O

InChI Identifier

InChI=1S/C11H12O8/c12-6-2-1-5(3-7(6)13)4-11(19,10(17)18)8(14)9(15)16/h1-3,8,12-14,19H,4H2,(H,15,16)(H,17,18)

InChI Key

PHFSBARLASYIFM-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
Actaea racemosa	LOTUS Database	35616633
Actaea simplex	LOTUS Database	35616633
Piscidia piscipula	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Beta-hydroxy acid
Sugar acid
Phenol
Alpha-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Hydroxy acid
Monosaccharide
Tertiary alcohol
Secondary alcohol
1,2-diol
Carboxylic acid
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	0.48	ALOGPS
logP	-0.35	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	2.99	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	155.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	59.51 m³·mol⁻¹	ChemAxon
Polarizability	23.91 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	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

Not Available

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

12309918

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid (NP0201875)

MOL for NP0201875 (2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid)

3D MOL for NP0201875 (2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid)

3D SDF for NP0201875 (2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid)

3D-SDF for NP0201875 (2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid)

PDB for NP0201875 (2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid)

3D PDB for NP0201875 (2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid)

SMILES for NP0201875 (2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid)

INCHI for NP0201875 (2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid)

Structure for NP0201875 (2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid)

3D Structure for NP0201875 (2-[(3,4-dihydroxyphenyl)methyl]-2,3-dihydroxybutanedioic acid)