NP-MRD: Showing NP-Card for 3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid (NP0167285)

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Record Information

Version

2.0

Created at

2022-09-03 02:50:42 UTC

Updated at

2022-09-03 02:50:42 UTC

NP-MRD ID

NP0167285

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid

Description

Methyl 4-(3,4-dihydroxybenzamido)butanoate belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom. Based on a literature review very few articles have been published on methyl 4-(3,4-dihydroxybenzamido)butanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 33  0  0  0  0  0  0  0  0999 V2000
   -6.3327   -0.6095   -0.9634 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9281   -0.7205   -1.0836 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1291    0.2385   -0.4830 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6890    1.1672    0.1438 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6577    0.1946   -0.5616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0918    1.3695    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5408    1.2378    0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1866    0.0332    0.6103 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775   -0.6509    0.8407 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -1.9080    1.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1799   -0.3281    0.5177 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5835    0.8208   -0.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9322    1.0715   -0.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8684    0.1354   -0.0241 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2152    0.3310   -0.2771 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4871   -1.0281    0.6011 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4525   -1.9876    0.9689 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1751   -1.2556    0.8661 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7936   -1.4456   -0.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6172    0.3456   -0.4792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7340   -0.5899   -2.0161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2369   -0.7217   -0.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2982    0.2115   -1.6233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2804    1.2699    1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4238    2.3424   -0.1773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1239    2.1549    0.5714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3094    1.2679   -1.0446 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5813   -2.6918    0.8465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8598    1.5627   -0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2239    1.9942   -0.8780 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5435    1.1859   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1087   -2.8181    1.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8415   -2.1739    1.3632 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
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 16 18  2  0
 18 11  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
 10 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 17 32  1  0
 18 33  1  0
M  END


  Mrv1652309032204502D          

 18 18  0  0  0  0            999 V2000
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  4  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 11 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0167285

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CCCN=C(O)C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H15NO5/c1-18-11(16)3-2-6-13-12(17)8-4-5-9(14)10(15)7-8/h4-5,7,14-15H,2-3,6H2,1H3,(H,13,17)

> <INCHI_KEY>
NCUSLXOBXZICBK-UHFFFAOYSA-N

> <FORMULA>
C12H15NO5

> <MOLECULAR_WEIGHT>
253.254

> <EXACT_MASS>
253.095022587

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
26.101298886087008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4-dihydroxy-N-(4-methoxy-4-oxobutyl)benzene-1-carboximidic acid

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
1.4095869653333333

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.596765026873546

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.009704085437699

> <JCHEM_PKA_STRONGEST_BASIC>
4.586023921924056

> <JCHEM_POLAR_SURFACE_AREA>
99.35000000000002

> <JCHEM_REFRACTIVITY>
64.8247

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,4-dihydroxy-N-(4-methoxy-4-oxobutyl)benzenecarboximidic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       4.001  -8.470   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335 -10.780   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -6.160   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      10.669  -6.160   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       9.336  -8.470   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   11                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4-(3,4-dihydroxybenzamido)butanoic acid	Generator

Chemical Formula

C₁₂H₁₅NO₅

Average Mass

253.2540 Da

Monoisotopic Mass

253.09502 Da

IUPAC Name

3,4-dihydroxy-N-(4-methoxy-4-oxobutyl)benzene-1-carboximidic acid

Traditional Name

3,4-dihydroxy-N-(4-methoxy-4-oxobutyl)benzenecarboximidic acid

CAS Registry Number

Not Available

SMILES

COC(=O)CCCN=C(O)C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C12H15NO5/c1-18-11(16)3-2-6-13-12(17)8-4-5-9(14)10(15)7-8/h4-5,7,14-15H,2-3,6H2,1H3,(H,13,17)

InChI Key

NCUSLXOBXZICBK-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Gamma amino acids and derivatives

Alternative Parents

Substituents

Gamma amino acid or derivatives
Benzamide
Benzoic acid or derivatives
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid methyl ester
Phenol
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Methyl ester
Carboxamide group
Carboxylic acid ester
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen 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	0.85	ALOGPS
logP	1.41	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	8.01	ChemAxon
pKa (Strongest Basic)	4.59	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	99.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	64.82 m³·mol⁻¹	ChemAxon
Polarizability	26.1 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

71116062

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102218164

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid (NP0167285)

MOL for NP0167285 (3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid)

3D MOL for NP0167285 (3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid)

3D SDF for NP0167285 (3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid)

3D-SDF for NP0167285 (3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid)

PDB for NP0167285 (3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid)

3D PDB for NP0167285 (3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid)

SMILES for NP0167285 (3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid)

INCHI for NP0167285 (3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid)

Structure for NP0167285 (3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid)

3D Structure for NP0167285 (3,4-dihydroxy-n-(4-methoxy-4-oxobutyl)benzenecarboximidic acid)