NP-MRD: Showing NP-Card for 2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid (NP0164331)

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Record Information

Version

2.0

Created at

2022-09-02 23:11:39 UTC

Updated at

2022-09-02 23:11:39 UTC

NP-MRD ID

NP0164331

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid

Description

2-Amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid 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. 2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid is found in Aleurodiscus amorphus. 2-Amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 37  0  0  0  0  0  0  0  0999 V2000
   -5.2380    0.5422    1.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7879    0.2340    0.3488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4942    0.2423   -0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4435    0.5760    0.7376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1290    0.5814    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0046    0.9453    1.1914 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5141    0.8297    2.5792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9063    0.7515    3.6650 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675    0.0897    1.0867 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2045    0.8552    0.8028 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4375   -0.0235    0.6716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2419   -1.0272   -0.4535 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0247   -0.3222   -1.7020 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4659   -1.8379   -0.6121 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1431   -1.8537   -1.6832 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9611   -2.6485    0.4208 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9294    0.2373   -1.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9513   -0.1024   -1.9023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7241   -0.4488   -3.2414 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2512   -0.0977   -1.4128 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2630   -0.4422   -2.2951 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2590   -0.3398    2.3158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2598    0.9701    1.6538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5664    1.2930    2.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6020    0.8468    1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799    1.9891    1.0324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3592    1.5745    1.6204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0497    1.4201   -0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2712    0.6422    0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6802   -0.5047    1.6217 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3288   -1.6490   -0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3988   -0.9154   -2.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5219    0.5969   -1.6097 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7769   -2.3734    0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0855    0.2411   -1.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7601   -0.4367   -3.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2143   -0.4352   -1.9240 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 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
  5  6  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 16  1  0
 14 15  2  0
  6  7  1  0
  7  8  3  0
 20  3  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 17 35  1  0
 19 36  1  0
 21 37  1  0
  6 26  1  6
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  1
 13 32  1  0
 13 33  1  0
 16 34  1  0
M  END


  Mrv1533004151518482D          

 21 21  0  0  0  0            999 V2000
    4.6077    6.8762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0676    6.2525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2575    6.4084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7174    5.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9073    5.9407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6372    6.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1773    7.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9073    8.1234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9874    7.1880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5275    7.8116    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3672    5.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5570    5.4730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0169    4.8493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7932    5.0052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3333    4.3816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    3.6020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6835    3.9139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4135    5.3171    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6372    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9073    3.7579    0.0000 N   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 11 20  1  0  0  0  0
 20 21  3  0  0  0  0
M  END
> <DATABASE_ID>
NP0164331

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(O)=C1O)C(OCCC(N)C(O)=O)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O6/c1-20-10-5-7(4-9(16)12(10)17)11(6-14)21-3-2-8(15)13(18)19/h4-5,8,11,16-17H,2-3,15H2,1H3,(H,18,19)

> <INCHI_KEY>
HREWMXYKFXVCNP-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O6

> <MOLECULAR_WEIGHT>
296.279

> <EXACT_MASS>
296.100836243

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.49181055981065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid

> <ALOGPS_LOGP>
-1.92

> <JCHEM_LOGP>
-2.477594649740304

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.71330014643448

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.13905921136079957

> <JCHEM_PKA_STRONGEST_BASIC>
9.105813120800299

> <JCHEM_POLAR_SURFACE_AREA>
146.03

> <JCHEM_REFRACTIVITY>
71.50440000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       8.601  12.835   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.593  11.671   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.081  11.962   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.072  10.798   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.560  11.089   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.056  12.544   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.064  13.709   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.560  15.164   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.577  13.418   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.585  14.582   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.552   9.925   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.040  10.216   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.032   9.052   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.481   9.343   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.489   8.179   0.000  0.00  0.00           C+0
HETATM   16  N   UNK     0      -1.985   6.724   0.000  0.00  0.00           N+0
HETATM   17  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.009   7.306   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -4.505   9.925   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       3.056   8.470   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.560   7.015   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7    3   10                                                  
CONECT   10    9                                                            
CONECT   11    5   12   20                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   11   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
2-Amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoate	Generator

Chemical Formula

C₁₃H₁₆N₂O₆

Average Mass

296.2790 Da

Monoisotopic Mass

296.10084 Da

IUPAC Name

2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid

Traditional Name

2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(O)=C1O)C(OCCC(N)C(O)=O)C#N

InChI Identifier

InChI=1S/C13H16N2O6/c1-20-10-5-7(4-9(16)12(10)17)11(6-14)21-3-2-8(15)13(18)19/h4-5,8,11,16-17H,2-3,15H2,1H3,(H,18,19)

InChI Key

HREWMXYKFXVCNP-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
Aleurodiscus amorphus	LOTUS Database	35616633

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

Alpha-amino acid
Alpha-amino acid or derivatives
Methoxyphenol
Benzylether
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Catechol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Ether
Nitrile
Monocarboxylic acid or derivatives
Carbonitrile
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Organooxygen compound
Primary amine
Organonitrogen compound
Organopnictogen compound
Amine
Organic oxide
Primary aliphatic amine
Hydrocarbon derivative
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	-1.9	ALOGPS
logP	-2.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.14	ChemAxon
pKa (Strongest Basic)	9.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	146.03 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	71.5 m³·mol⁻¹	ChemAxon
Polarizability	28.49 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid (NP0164331)

MOL for NP0164331 (2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid)

3D MOL for NP0164331 (2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid)

3D SDF for NP0164331 (2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid)

3D-SDF for NP0164331 (2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid)

PDB for NP0164331 (2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid)

3D PDB for NP0164331 (2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid)

SMILES for NP0164331 (2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid)

INCHI for NP0164331 (2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid)

Structure for NP0164331 (2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid)

3D Structure for NP0164331 (2-amino-4-[cyano(3,4-dihydroxy-5-methoxyphenyl)methoxy]butanoic acid)