NP-MRD: Showing NP-Card for 2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid (NP0294376)

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Record Information

Version

2.0

Created at

2022-09-10 02:53:08 UTC

Updated at

2022-09-10 02:53:08 UTC

NP-MRD ID

NP0294376

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid

Description

ACMC-20n0qe belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. 2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid is found in Ephedra distachya. ACMC-20n0qe is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
   -4.2170   -1.1342   -0.2990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6101   -0.0589    0.6081 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1948   -0.0141    0.3977 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3059   -0.3481    1.4356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265   -0.6875    2.5564 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1473   -0.3257    1.2955 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7550    0.0079    0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2097    0.0281    0.0563 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7902    0.3977   -1.1648 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1504    0.4300   -1.3325 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0227    0.1031   -0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4003    0.1405   -0.5018 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4707   -0.2626    0.8903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0886   -0.2959    1.0625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2410    1.2403    0.3102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5979    2.2466   -0.0782 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6201    1.3560    0.4679 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8155   -1.0382   -1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8610   -2.1013    0.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3093   -1.0501   -0.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8379   -0.3820    1.6626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8294    0.2669   -0.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7377   -0.5996    2.1531 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1636    0.2833   -0.6730 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1171    0.6598   -1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5956    0.7223   -2.2977 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8476   -0.7171   -0.8328 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1458   -0.5218    1.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7043   -0.5890    2.0274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0801    2.2437    0.5091 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
  2 15  1  0
 15 17  1  0
 15 16  2  0
 14  8  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  1
  3 22  1  0
  6 23  1  0
  7 24  1  0
  9 25  1  0
 10 26  1  0
 12 27  1  0
 13 28  1  0
 14 29  1  0
 17 30  1  0
M  END


  Mrv0541 04121513212D          

 17 17  0  0  0  0            999 V2000
    1.4289   -1.6500    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
    0.7145   -2.8875    0.0000 N   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
    0.0000   -1.6500    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
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    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   -5.3625    0.0000 C   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
   -3.5724   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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   -3.7125    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  1  0  0  0  0
  4  5  2  0  0  0  0
  6  4  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0294376

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H13NO4/c1-8(12(16)17)13-11(15)7-4-9-2-5-10(14)6-3-9/h2-8,14H,1H3,(H,13,15)(H,16,17)

> <INCHI_KEY>
MGHQKUMJBPRMPS-UHFFFAOYSA-N

> <FORMULA>
C12H13NO4

> <MOLECULAR_WEIGHT>
235.239

> <EXACT_MASS>
235.084457903

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
23.92447826966759

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[3-(4-hydroxyphenyl)prop-2-enamido]propanoic acid

> <ALOGPS_LOGP>
1.69

> <JCHEM_LOGP>
1.296001941

> <ALOGPS_LOGS>
-2.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.42007492008683

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.735871106763956

> <JCHEM_PKA_STRONGEST_BASIC>
-0.678307307436884

> <JCHEM_POLAR_SURFACE_AREA>
86.63000000000001

> <JCHEM_REFRACTIVITY>
62.338200000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[3-(4-hydroxyphenyl)prop-2-enamido]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       1.334  -5.390   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13    8                                                       
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₂H₁₃NO₄

Average Mass

235.2390 Da

Monoisotopic Mass

235.08446 Da

IUPAC Name

2-[3-(4-hydroxyphenyl)prop-2-enamido]propanoic acid

Traditional Name

2-[3-(4-hydroxyphenyl)prop-2-enamido]propanoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C12H13NO4/c1-8(12(16)17)13-11(15)7-4-9-2-5-10(14)6-3-9/h2-8,14H,1H3,(H,13,15)(H,16,17)

InChI Key

MGHQKUMJBPRMPS-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
Ephedra distachya	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-acyl-alpha amino acids

Alternative Parents

Substituents

N-acyl-alpha-amino acid
Cinnamic acid amide
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Alanine or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Monocarboxylic acid or derivatives
Carboxylic acid
Organonitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
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	1.69	ALOGPS
logP	1.3	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.74	ChemAxon
pKa (Strongest Basic)	-0.68	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.63 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	62.34 m³·mol⁻¹	ChemAxon
Polarizability	23.92 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

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

71343879

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid (NP0294376)

MOL for NP0294376 (2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid)

3D MOL for NP0294376 (2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid)

3D SDF for NP0294376 (2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid)

3D-SDF for NP0294376 (2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid)

PDB for NP0294376 (2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid)

3D PDB for NP0294376 (2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid)

SMILES for NP0294376 (2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid)

INCHI for NP0294376 (2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid)

Structure for NP0294376 (2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid)

3D Structure for NP0294376 (2-{[1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}propanoic acid)