NP-MRD: Showing NP-Card for 4-Coumaroylputrescine (NP0047652)

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Record Information

Version

2.0

Created at

2022-03-17 20:43:43 UTC

Updated at

2022-03-17 20:43:43 UTC

NP-MRD ID

NP0047652

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Coumaroylputrescine

Description

4-Coumaroylputrescine belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. 4-Coumaroylputrescine is a very strong basic compound (based on its pKa). Outside of the human body, 4-Coumaroylputrescine has been detected, but not quantified in, several different foods, such as cereals and cereal products, fats and oils, fruits, and garden tomato. 4-Coumaroylputrescine is found in Oryza sativa , Pennisetum americanum , Persea gratissima and Zea mays . This could make 4-coumaroylputrescine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241216522D          

 17 17  0  0  0  0            999 V2000
   -0.7380   -2.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769   -1.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4769   -0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7380   -0.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0813   -1.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559   -2.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948   -1.6004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4769   -0.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2157   -0.3698    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2157    0.4511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4769    0.8616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3948    1.6825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6559    2.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0008    1.6004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9022   -0.2056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2157   -0.4511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3 17  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  2  0  0  0  0
 10 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
M  END
> <DATABASE_ID>
NP0047652

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NCCCCNC(=O)\C=C/C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H18N2O2/c14-9-1-2-10-15-13(17)8-5-11-3-6-12(16)7-4-11/h3-8,16H,1-2,9-10,14H2,(H,15,17)/b8-5-

> <INCHI_KEY>
CJHDBEPXEKGBDW-YVMONPNESA-N

> <FORMULA>
C13H18N2O2

> <MOLECULAR_WEIGHT>
234.2942

> <EXACT_MASS>
234.13682783

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
26.418677649063316

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-N-(4-aminobutyl)-3-(4-hydroxyphenyl)prop-2-enamide

> <ALOGPS_LOGP>
1.12

> <JCHEM_LOGP>
0.22419931278505054

> <ALOGPS_LOGS>
-2.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
16.232370935440716

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.29683990242163

> <JCHEM_PKA_STRONGEST_BASIC>
10.027301810332872

> <JCHEM_POLAR_SURFACE_AREA>
75.35

> <JCHEM_REFRACTIVITY>
69.21950000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-N-(4-aminobutyl)-3-(4-hydroxyphenyl)prop-2-enamide

> <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      -1.378  -3.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.757  -3.141   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.757  -1.608   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.378  -0.842   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.152  -1.608   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.152  -3.141   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.224  -3.907   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.604  -2.987   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.757  -1.455   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       4.136  -0.690   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.136   0.842   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.757   1.608   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.604   3.141   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.224   3.907   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       0.001   2.987   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       1.684  -0.384   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -4.136  -0.842   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    1    5    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16    9                                                            
CONECT   17    3                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

View in JSmol

Synonyms

Value	Source
(e)-N-(4-Aminobutyl)-3-(4-hydroxyphenyl)prop-2-enamide	HMDB
4-Hydroxycinnamoylputrescine	HMDB
(2Z)-N-(4-Aminobutyl)-3-(4-hydroxyphenyl)prop-2-enimidate	Generator

Chemical Formula

C₁₃H₁₈N₂O₂

Average Mass

234.2942 Da

Monoisotopic Mass

234.13683 Da

IUPAC Name

(2Z)-N-(4-aminobutyl)-3-(4-hydroxyphenyl)prop-2-enamide

Traditional Name

(2Z)-N-(4-aminobutyl)-3-(4-hydroxyphenyl)prop-2-enamide

CAS Registry Number

34136-53-3

SMILES

NCCCCNC(=O)\C=C/C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C13H18N2O2/c14-9-1-2-10-15-13(17)8-5-11-3-6-12(16)7-4-11/h3-8,16H,1-2,9-10,14H2,(H,15,17)/b8-5-

InChI Key

CJHDBEPXEKGBDW-YVMONPNESA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Oryza sativa	Plant	KNApSAcK
Pennisetum americanum	Plant	KNApSAcK
Persea americana	Plant	KNApSAcK
Solanum lycopersicum	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 coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Cinnamic acid amide
Coumaric acid or derivatives
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Amine
Carbonyl group
Organic nitrogen compound
Primary 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	1.12	ALOGPS
logP	0.22	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	9.3	ChemAxon
pKa (Strongest Basic)	10.03	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	75.35 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	69.22 m³·mol⁻¹	ChemAxon
Polarizability	26.42 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

HMDB0033461

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011503

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

131751428

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Coumaroylputrescine (NP0047652)

MOL for NP0047652 (4-Coumaroylputrescine)

3D MOL for NP0047652 (4-Coumaroylputrescine)

3D SDF for NP0047652 (4-Coumaroylputrescine)

3D-SDF for NP0047652 (4-Coumaroylputrescine)

PDB for NP0047652 (4-Coumaroylputrescine)

3D PDB for NP0047652 (4-Coumaroylputrescine)

SMILES for NP0047652 (4-Coumaroylputrescine)

INCHI for NP0047652 (4-Coumaroylputrescine)

Structure for NP0047652 (4-Coumaroylputrescine)

3D Structure for NP0047652 (4-Coumaroylputrescine)