NP-MRD: Showing NP-Card for (2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid (NP0319347)

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Record Information

Version

2.0

Created at

2022-09-11 20:19:50 UTC

Updated at

2022-09-11 20:19:50 UTC

NP-MRD ID

NP0319347

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid

Description

3-(3,4-Dihydroxy-5-methoxybenzoyloxymethyl)alanine belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. (2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid is found in Aleurodiscus amorphus. Based on a literature review very few articles have been published on 3-(3,4-Dihydroxy-5-methoxybenzoyloxymethyl)alanine.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 35  0  0  0  0  0  0  0  0999 V2000
   -4.5927    2.1302    1.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8004    0.7570    0.8266 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7606   -0.0752    0.3948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4926    0.4184    0.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5079   -0.4212   -0.2336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1572    0.1131   -0.4539 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0878    1.3248   -0.2588 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8670   -0.7072   -0.8794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1595   -0.2383   -1.0981 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7979    0.3489    0.1388 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1989    0.8049   -0.2930 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.8925   -0.3429   -0.7631 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8828    1.5028    0.8200 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3531    2.5322    1.3109 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0896    1.0873    1.3646 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7266   -1.7771   -0.4655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9855   -2.2677   -0.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2513   -3.6008   -0.4741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9949   -1.4107    0.1710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2447   -1.9496    0.3655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6853    2.3058    1.6783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4701    2.5308    1.5863 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4180    2.6154    0.0881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3214    1.4707    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7985   -1.0956   -1.4014 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1786    0.4970   -1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2420    1.1675    0.5982 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9152   -0.4389    0.9194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0372    1.5048   -1.1398 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3035   -0.9462   -0.0415 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5030   -0.1796   -1.5880 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1974    0.1387    1.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9292   -2.4141   -0.7964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1512   -4.0285   -0.3423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0148   -1.3564    0.6805 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 19 20  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 15  1  0
 13 14  2  0
 19  3  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  4 24  1  0
 16 33  1  0
 18 34  1  0
 20 35  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  6
 12 30  1  0
 12 31  1  0
 15 32  1  0
M  END


  Mrv1652309112222192D          

 20 20  0  0  1  0            999 V2000
   -5.0013    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    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
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    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
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  5 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
  3 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0319347

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(O)=C1O)C(=O)OCC[C@H](N)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C12H15NO7/c1-19-9-5-6(4-8(14)10(9)15)12(18)20-3-2-7(13)11(16)17/h4-5,7,14-15H,2-3,13H2,1H3,(H,16,17)/t7-/m0/s1

> <INCHI_KEY>
DOGIWBIDAAYBPO-ZETCQYMHSA-N

> <FORMULA>
C12H15NO7

> <MOLECULAR_WEIGHT>
285.252

> <EXACT_MASS>
285.084851827

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.584922468220004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid

> <JCHEM_LOGP>
-2.0978154713861104

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.866750894924133

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.9599616051194735

> <JCHEM_PKA_STRONGEST_BASIC>
9.586180544192063

> <JCHEM_POLAR_SURFACE_AREA>
139.31

> <JCHEM_REFRACTIVITY>
67.1534

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.667   6.160   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.335   0.000   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -8.002   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16    5   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    3   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₅NO₇

Average Mass

285.2520 Da

Monoisotopic Mass

285.08485 Da

IUPAC Name

(2S)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid

Traditional Name

(2S)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(O)=C1O)C(=O)OCC[C@H](N)C(O)=O

InChI Identifier

InChI=1S/C12H15NO7/c1-19-9-5-6(4-8(14)10(9)15)12(18)20-3-2-7(13)11(16)17/h4-5,7,14-15H,2-3,13H2,1H3,(H,16,17)/t7-/m0/s1

InChI Key

DOGIWBIDAAYBPO-ZETCQYMHSA-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
Aleurodiscus amorphus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acid and derivatives

Alternative Parents

Substituents

Gallic acid or derivatives
M-methoxybenzoic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Methoxyphenol
Benzoate ester
Alpha-amino acid
Alpha-amino acid or derivatives
L-alpha-amino acid
Phenoxy compound
Catechol
Benzoyl
Phenol ether
Anisole
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
1-hydroxy-4-unsubstituted benzenoid
Carboxylic acid ester
Amino acid
Amino acid or derivatives
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Carboxylic acid
Ether
Organic nitrogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
Primary amine
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Primary aliphatic amine
Amine
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	-2.1	ChemAxon
pKa (Strongest Acidic)	0.96	ChemAxon
pKa (Strongest Basic)	9.59	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	139.31 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	67.15 m³·mol⁻¹	ChemAxon
Polarizability	27.58 Å³	ChemAxon
Number of Rings	1	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78436512

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101450523

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid (NP0319347)

MOL for NP0319347 ((2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid)

3D MOL for NP0319347 ((2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid)

3D SDF for NP0319347 ((2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid)

3D-SDF for NP0319347 ((2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid)

PDB for NP0319347 ((2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid)

3D PDB for NP0319347 ((2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid)

SMILES for NP0319347 ((2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid)

INCHI for NP0319347 ((2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid)

Structure for NP0319347 ((2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid)

3D Structure for NP0319347 ((2s)-2-amino-4-(3,4-dihydroxy-5-methoxybenzoyloxy)butanoic acid)