NP-MRD: Showing NP-Card for Avenanthramide L (NP0085205)

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Record Information

Version

2.0

Created at

2022-04-29 05:47:32 UTC

Updated at

2022-04-29 05:47:32 UTC

NP-MRD ID

NP0085205

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Avenanthramide L

Description

Avenanthramide L belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated. Avenanthramide L is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Avenanthramide L has been detected, but not quantified in, cereals and cereal products and oats. Avenanthramide L is found in Avena sativa, Avena sativa and Puccinia coronata f.sp. avenae. This could make avenanthramide L a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
   -1.5653   -1.2962   -1.2748 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4436   -0.3802   -0.4597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0612   -0.0446   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9852   -0.6788   -0.4806 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3399   -0.3012   -0.0152 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4024   -0.9296   -0.4607 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7598   -0.6412   -0.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0987    0.3456    0.8254 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4111    0.6217    1.1976 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4495   -0.1062    0.6625 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7739    0.1534    1.0214 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1176   -1.0949   -0.2373 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8243   -1.3700   -0.6067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5144    0.3598    0.0830 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8843    0.2222   -0.1758 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3647   -0.6741   -1.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7036   -0.8255   -1.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6274   -0.0725   -0.7753 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0038   -0.1873   -1.0428 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2039    0.8016    0.1607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8274    0.9611    0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5282    1.9196    1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4013    2.1790    1.9262 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5690    2.6532    2.1331 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1094    0.7515    0.6866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8475   -1.4757   -1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4581    0.4904    0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2434   -1.7356   -1.1832 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3031    0.9450    1.2721 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6444    1.4118    1.9135 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1613   -0.3547    1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9483   -1.6654   -0.6551 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6362   -2.1629   -1.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2276    1.1250    0.7681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6531   -1.2732   -1.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9882   -1.5380   -2.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6662    0.3660   -0.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9475    1.3988    0.6870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3335    2.1021    2.5021 H   0  0  0  0  0  0  0  0  0  0  0  0
 24 22  1  0
 22 23  2  0
 22 21  1  0
 21 15  2  0
 15 14  1  0
 14  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 21  1  0
 13  7  1  0
 24 39  1  0
 14 34  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 16 35  1  0
 17 36  1  0
 19 37  1  0
 20 38  1  0
M  END


  Mrv0541 02241216032D          

 24 25  0  0  0  0            999 V2000
   -3.9292   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9292   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156   -1.4431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5032   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5032   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6442   -1.4431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7882    0.2069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3581    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0731   -1.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3568   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0718    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7868   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5019    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9305    0.2069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9305    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169    1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5019    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6442    1.4431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2156    1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9306    1.4431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5005    1.4431    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  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
  5  8  1  0  0  0  0
  6 22  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 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
 15 16  1  0  0  0  0
 15 20  2  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 21  1  0  0  0  0
 19 20  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0085205

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=C(NC(=O)\C=C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H15NO5/c20-13-7-5-12(6-8-13)3-1-2-4-17(22)19-16-10-9-14(21)11-15(16)18(23)24/h1-11,20-21H,(H,19,22)(H,23,24)/b3-1+,4-2+

> <INCHI_KEY>
FRNDILDQFSAXAR-ZPUQHVIOSA-N

> <FORMULA>
C18H15NO5

> <MOLECULAR_WEIGHT>
325.3154

> <EXACT_MASS>
325.095022595

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
33.81366680162238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-2-[(2E,4E)-5-(4-hydroxyphenyl)penta-2,4-dienamido]benzoic acid

> <ALOGPS_LOGP>
3.40

> <JCHEM_LOGP>
3.7980560956666665

> <ALOGPS_LOGS>
-4.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.200753240329515

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3071329604039654

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6100212917755075

> <JCHEM_POLAR_SURFACE_AREA>
106.86000000000001

> <JCHEM_REFRACTIVITY>
92.8738

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.64e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-2-[(2E,4E)-5-(4-hydroxyphenyl)penta-2,4-dienamido]benzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.335  -0.384   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.335  -1.924   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.002  -2.694   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.673  -1.924   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.673  -0.384   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.002   0.384   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.669  -2.694   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      -3.338   0.386   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -2.003  -0.384   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.668   0.386   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.003  -1.924   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.666  -0.384   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.001   0.386   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.335  -0.384   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.670   0.386   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.005  -0.384   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.337   0.386   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.337   1.924   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.005   2.691   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.670   1.924   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.669   2.694   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -6.002   1.924   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -7.337   2.694   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -4.668   2.694   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    1    5   22                                                  
CONECT    7    2                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   12                                                       
CONECT   11    9                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   21                                                  
CONECT   19   18   20                                                       
CONECT   20   15   19                                                       
CONECT   21   18                                                            
CONECT   22    6   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

View in JSmol

Synonyms

Value	Source
5-Hydroxy-2-{[(2E,4E)-1-hydroxy-5-(4-hydroxyphenyl)penta-2,4-dien-1-ylidene]amino}benzoate	Generator

Chemical Formula

C₁₈H₁₅NO₅

Average Mass

325.3154 Da

Monoisotopic Mass

325.09502 Da

IUPAC Name

5-hydroxy-2-[(2E,4E)-5-(4-hydroxyphenyl)penta-2,4-dienamido]benzoic acid

Traditional Name

5-hydroxy-2-[(2E,4E)-5-(4-hydroxyphenyl)penta-2,4-dienamido]benzoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=C(NC(=O)\C=C\C=C\C2=CC=C(O)C=C2)C=CC(O)=C1

InChI Identifier

InChI=1S/C18H15NO5/c20-13-7-5-12(6-8-13)3-1-2-4-17(22)19-16-10-9-14(21)11-15(16)18(23)24/h1-11,20-21H,(H,19,22)(H,23,24)/b3-1+,4-2+

InChI Key

FRNDILDQFSAXAR-ZPUQHVIOSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Avena sativa	LOTUS Database	35616633
Avena sativa L.	Plant	KNApSAcK
Puccinia coronata f.sp. avenae	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acylaminobenzoic acid and derivatives. These are derivatives of amino benzoic acid derivatives where the amine group is N-acylated.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Acylaminobenzoic acid and derivatives

Alternative Parents

Substituents

Acylaminobenzoic acid or derivatives
Hydroxybenzoic acid
Benzoic acid
Anilide
Benzoyl
N-arylamide
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Carbonyl group
Organonitrogen compound
Organooxygen compound
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	3.4	ALOGPS
logP	3.8	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	3.31	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	106.86 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	92.87 m³·mol⁻¹	ChemAxon
Polarizability	33.81 Å³	ChemAxon
Number of Rings	2	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

HMDB0033193

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011205

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

101688490

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Avenanthramide L (NP0085205)

MOL for NP0085205 (Avenanthramide L)

3D MOL for NP0085205 (Avenanthramide L)

3D SDF for NP0085205 (Avenanthramide L)

3D-SDF for NP0085205 (Avenanthramide L)

PDB for NP0085205 (Avenanthramide L)

3D PDB for NP0085205 (Avenanthramide L)

SMILES for NP0085205 (Avenanthramide L)

INCHI for NP0085205 (Avenanthramide L)

Structure for NP0085205 (Avenanthramide L)

3D Structure for NP0085205 (Avenanthramide L)