NP-MRD: Showing NP-Card for Avenanthramide K (NP0045305)

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Record Information

Version

2.0

Created at

2022-03-17 19:17:36 UTC

Updated at

2022-03-17 19:17:36 UTC

NP-MRD ID

NP0045305

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Avenanthramide K

Description

Avenanthramide K is found in Avena sativa.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
    1.1711    2.5249    0.4759 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454    1.4213    0.2767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7979    1.4009    0.1306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4946    0.3181   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9562    0.3180   -0.2289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7123    1.4610   -0.1509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1058    1.4306   -0.2934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7653    0.2465   -0.5175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1342    0.1731   -0.6633 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9866   -0.8963   -0.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6324   -2.1001   -0.8187 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6286   -0.8751   -0.4555 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4044    0.2391    0.1947 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8135    0.1058    0.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5500    1.1734    0.8642 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9063    1.1055    1.0819 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6331    2.1661    1.6171 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5505   -0.0623    0.7521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8403   -1.1100    0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4491   -1.0544   -0.0061 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8004   -2.1835   -0.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6116   -2.2820   -0.9160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5706   -3.3546   -0.8958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3564    2.3317    0.1998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9982   -0.6383   -0.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2816    2.4347    0.0224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6860    2.3351   -0.2298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5711   -0.7239   -0.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1216   -2.9605   -0.8832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0159   -1.7661   -0.5140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9013   -0.6905    0.0495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0992    2.1028    1.1503 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0633    2.8854    1.0657 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6275   -0.1264    0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3327   -2.0313   -0.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2741   -3.3186   -1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
 23 21  1  0
 21 22  2  0
 21 20  1  0
 20 19  2  0
 19 18  1  0
 18 16  2  0
 16 17  1  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 12  2  0
 12 10  1  0
 10 11  1  0
 10  8  2  0
  8  9  1  0
  8  7  1  0
  7  6  2  0
 14 20  1  0
  6  5  1  0
 23 36  1  0
 19 35  1  0
 18 34  1  0
 17 33  1  0
 15 32  1  0
 13 31  1  0
  3 24  1  0
  4 25  1  0
 12 30  1  0
 11 29  1  0
  9 28  1  0
  7 27  1  0
  6 26  1  0
M  END


  Mrv0541 02271201072D          

 23 24  0  0  0  0            999 V2000
   -0.3830    2.2393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0975    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3830    0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314    1.8268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3830   -0.2357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3315   -0.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974   -0.6482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0459    0.5893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7603    1.0018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4748    0.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7603    1.8268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893    1.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038    0.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6182    1.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9038   -0.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6182   -0.6482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3327   -0.2356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3327    0.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3830    3.0643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0472    1.0019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0472   -0.6481    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  5 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 16 15  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 16 20  1  0  0  0  0
  1 21  1  0  0  0  0
 20 22  1  0  0  0  0
 19 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045305

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC=C(O)C=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C16H13NO6/c18-10-3-4-11(16(22)23)12(8-10)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)/b6-2+

> <INCHI_KEY>
OSILFOKGSJBVLY-QHHAFSJGSA-N

> <FORMULA>
C16H13NO6

> <MOLECULAR_WEIGHT>
315.2775

> <EXACT_MASS>
315.074287153

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
31.011557010651234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-4-hydroxybenzoic acid

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
2.967275100666667

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.020230091318764

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.867608748009035

> <JCHEM_PKA_STRONGEST_BASIC>
-2.0685230336253135

> <JCHEM_POLAR_SURFACE_AREA>
127.09000000000002

> <JCHEM_REFRACTIVITY>
84.53610000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.67e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-4-hydroxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      -0.715   4.180   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.049   3.410   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.049   1.870   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.715   1.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.619   1.870   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.619   3.410   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.715  -0.440   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.619  -1.210   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.048  -1.210   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0       1.952   1.100   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       3.286   1.870   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.620   1.100   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.286   3.410   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.953   1.870   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.287   1.100   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.621   1.870   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.287  -0.440   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.621  -1.210   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.954  -0.440   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.954   1.100   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.715   5.720   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      11.288   1.870   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      11.288  -1.210   0.000  0.00  0.00           O+0
CONECT    1    2    6   21                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10                                                  
CONECT    6    1    5                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11   14                                                       
CONECT   13   11                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15   20                                                       
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   23                                                  
CONECT   20   19   16   22                                                  
CONECT   21    1                                                            
CONECT   22   20                                                            
CONECT   23   19                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₃NO₆

Average Mass

315.2775 Da

Monoisotopic Mass

315.07429 Da

IUPAC Name

2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-4-hydroxybenzoic acid

Traditional Name

2-[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enamido]-4-hydroxybenzoic acid

CAS Registry Number

7664-41-7

SMILES

OC(=O)C1=CC=C(O)C=C1NC(=O)\C=C\C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C16H13NO6/c18-10-3-4-11(16(22)23)12(8-10)17-15(21)6-2-9-1-5-13(19)14(20)7-9/h1-8,18-20H,(H,17,21)(H,22,23)/b6-2+

InChI Key

OSILFOKGSJBVLY-QHHAFSJGSA-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.	FooDB	PHENOL EXPLORER

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as avenanthramides. These are a group of phenolic alkaloids consisting of conjugate of three phenylpropanoids (ferulic, caffeic, or p-coumaric acid) and anthranilic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Avenanthramides

Alternative Parents

Substituents

Avenanthramide
N-cinnamoylanthranilic acid
Acylaminobenzoic acid or derivatives
Cinnamic acid amide
Hydroxybenzoic acid
Anilide
Benzoic acid or derivatives
Benzoic acid
Styrene
N-arylamide
Catechol
Benzoyl
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous amide
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organooxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organic oxygen 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	2.55	ALOGPS
logP	2.97	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	3.87	ChemAxon
pKa (Strongest Basic)	-2.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.09 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	84.54 m³·mol⁻¹	ChemAxon
Polarizability	31.01 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000304

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

10018570

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Avenanthramide K (NP0045305)

MOL for NP0045305 (Avenanthramide K)

3D MOL for NP0045305 (Avenanthramide K)

3D SDF for NP0045305 (Avenanthramide K)

3D-SDF for NP0045305 (Avenanthramide K)

PDB for NP0045305 (Avenanthramide K)

3D PDB for NP0045305 (Avenanthramide K)

SMILES for NP0045305 (Avenanthramide K)

INCHI for NP0045305 (Avenanthramide K)

Structure for NP0045305 (Avenanthramide K)

3D Structure for NP0045305 (Avenanthramide K)