NP-MRD: Showing NP-Card for Na-p-Hydroxycoumaroyltryptophan (NP0049836)

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Record Information

Version

2.0

Created at

2022-03-17 21:18:54 UTC

Updated at

2022-03-17 21:18:54 UTC

NP-MRD ID

NP0049836

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Na-p-Hydroxycoumaroyltryptophan

Description

Na-p-Hydroxycoumaroyltryptophan 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. Na-p-Hydroxycoumaroyltryptophan is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Na-p-Hydroxycoumaroyltryptophan has been detected, but not quantified in, coffee and coffee products. Na-p-Hydroxycoumaroyltryptophan is found in Zea mays . This could make na-p-hydroxycoumaroyltryptophan a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241209232D          

 26 28  0  0  0  0            999 V2000
   -1.1722    1.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    1.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529    0.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6936    0.1815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853    0.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1829    0.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7658    1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5527    1.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7552    2.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1011    2.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9247    2.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3372    2.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9247    3.5490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3372    1.4053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622    2.8340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0522    0.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0536    0.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7658    1.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3400   -0.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3400   -1.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249   -1.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249   -2.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3400   -2.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0536   -2.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0536   -1.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3400   -3.5490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  2  0  0  0  0
  1  9  1  0  0  0  0
  2  3  2  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  2  0  0  0  0
 12 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
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 26  1  0  0  0  0
 24 25  2  0  0  0  0
M  END


  Mrv0541 02241209232D          

 26 28  0  0  0  0            999 V2000
   -1.1722    1.4286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486    1.4713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0529    0.7012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6936    0.1815    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853    0.6311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1829    0.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7658    1.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5527    1.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7552    2.0117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1011    2.1630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9247    2.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3372    2.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9247    3.5490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3372    1.4053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1622    2.8340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0522    0.9928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0536    0.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7658    1.4067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3400   -0.2461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3400   -1.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249   -1.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249   -2.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3400   -2.7240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0536   -2.3114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0536   -1.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3400   -3.5490    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  5  2  0  0  0  0
  1  9  1  0  0  0  0
  2  3  2  0  0  0  0
  2 10  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 14  1  0  0  0  0
 12 13  2  0  0  0  0
 12 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
 17 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 23 26  1  0  0  0  0
 24 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0049836

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C(CC1=CNC2=C1C=CC=C2)NC(=O)\C=C\C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H18N2O4/c23-15-8-5-13(6-9-15)7-10-19(24)22-18(20(25)26)11-14-12-21-17-4-2-1-3-16(14)17/h1-10,12,18,21,23H,11H2,(H,22,24)(H,25,26)/b10-7+

> <INCHI_KEY>
IDUPBPKKEQWWCP-JXMROGBWSA-N

> <FORMULA>
C20H18N2O4

> <MOLECULAR_WEIGHT>
350.3679

> <EXACT_MASS>
350.126657074

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.754104639747865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]-3-(1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
3.20

> <JCHEM_LOGP>
3.0510903016666657

> <ALOGPS_LOGS>
-4.81

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.420072204558053

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.955435630674385

> <JCHEM_PKA_STRONGEST_BASIC>
0.7026415980971698

> <JCHEM_POLAR_SURFACE_AREA>
102.42

> <JCHEM_REFRACTIVITY>
98.0437

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.42e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]-3-(1H-indol-3-yl)propanoic 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      -2.188   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.651   2.746   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.099   1.309   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      -1.295   0.339   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      -2.586   1.178   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.075   0.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.163   1.869   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.765   3.355   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.276   3.755   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.189   4.038   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.726   3.958   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.496   5.290   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.726   6.625   0.000  0.00  0.00           O+0
HETATM   14  N   UNK     0       2.496   2.623   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0       4.036   5.290   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.831   1.853   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.833   0.313   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.163   2.626   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.501  -0.459   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.501  -1.999   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.166  -2.772   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.166  -4.315   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.501  -5.085   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.833  -4.315   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.833  -2.772   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.501  -6.625   0.000  0.00  0.00           O+0
CONECT    1    2    5    9                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    1    4    6                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    1    8                                                       
CONECT   10    2   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12                                                            
CONECT   14   11   16                                                       
CONECT   15   12                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16   19                                                       
CONECT   18   16                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   20   24                                                       
CONECT   26   23                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

View in JSmol

Synonyms

Value	Source
2-{[(2E)-1-hydroxy-3-(4-hydroxyphenyl)prop-2-en-1-ylidene]amino}-3-(1H-indol-3-yl)propanoate	Generator

Chemical Formula

C₂₀H₁₈N₂O₄

Average Mass

350.3679 Da

Monoisotopic Mass

350.12666 Da

IUPAC Name

2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]-3-(1H-indol-3-yl)propanoic acid

Traditional Name

2-[(2E)-3-(4-hydroxyphenyl)prop-2-enamido]-3-(1H-indol-3-yl)propanoic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C(CC1=CNC2=C1C=CC=C2)NC(=O)\C=C\C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C20H18N2O4/c23-15-8-5-13(6-9-15)7-10-19(24)22-18(20(25)26)11-14-12-21-17-4-2-1-3-16(14)17/h1-10,12,18,21,23H,11H2,(H,22,24)(H,25,26)/b10-7+

InChI Key

IDUPBPKKEQWWCP-JXMROGBWSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coffea arabica L.	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coffea canephora	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Zea mays L.	Plant	KNApSAcK

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
Indolyl carboxylic acid derivative
3-alkylindole
Indole
Indole or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Secondary carboxylic acid amide
Carboxamide group
Organoheterocyclic compound
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid
Organooxygen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	3.2	ALOGPS
logP	3.05	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	3.96	ChemAxon
pKa (Strongest Basic)	0.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	102.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	98.04 m³·mol⁻¹	ChemAxon
Polarizability	36.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

HMDB0041370

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB021295

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

24891366

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Na-p-Hydroxycoumaroyltryptophan (NP0049836)

MOL for NP0049836 (Na-p-Hydroxycoumaroyltryptophan)

3D MOL for NP0049836 (Na-p-Hydroxycoumaroyltryptophan)

3D SDF for NP0049836 (Na-p-Hydroxycoumaroyltryptophan)

3D-SDF for NP0049836 (Na-p-Hydroxycoumaroyltryptophan)

PDB for NP0049836 (Na-p-Hydroxycoumaroyltryptophan)

3D PDB for NP0049836 (Na-p-Hydroxycoumaroyltryptophan)

SMILES for NP0049836 (Na-p-Hydroxycoumaroyltryptophan)

INCHI for NP0049836 (Na-p-Hydroxycoumaroyltryptophan)

Structure for NP0049836 (Na-p-Hydroxycoumaroyltryptophan)

3D Structure for NP0049836 (Na-p-Hydroxycoumaroyltryptophan)