NP-MRD: Showing NP-Card for N-trans-p-Coumaroyloctopamine (NP0047467)

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Record Information

Version

2.0

Created at

2022-03-17 20:40:42 UTC

Updated at

2022-03-17 20:40:42 UTC

NP-MRD ID

NP0047467

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-trans-p-Coumaroyloctopamine

Description

N-trans-p-Coumaroyloctopamine, also known as 4-coumaroylnoradrenaline, 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. N-trans-p-Coumaroyloctopamine is a moderately basic compound (based on its pKa). Outside of the human body, N-trans-p-Coumaroyloctopamine is found, on average, in the highest concentration within a few different foods, such as yellow bell peppers, red bell peppers, and pepper (c. Annuum) and in a lower concentration in orange bell peppers and green bell peppers. N-trans-p-Coumaroyloctopamine has also been detected, but not quantified in, several different foods, such as eggplants, fruits, herbs and spices, and italian sweet red peppers. N-trans-p-Coumaroyloctopamine is found in Capsicum annuum var. grossum . This could make N-trans-p-coumaroyloctopamine a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241210062D          

 22 23  0  0  0  0            999 V2000
   -2.8398    0.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5012    0.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5012   -0.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8398   -0.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974   -0.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0974    0.4510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2437    0.8634    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6126    0.4510    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6950   -0.3740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3550   -0.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3550   -1.6114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1396    0.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2220    1.6114    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8091    0.3093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5612    0.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2308    0.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1510   -0.6545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8219   -1.1358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5740   -0.7961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6552    0.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9829    0.5060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2437   -1.2773    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 10  1  0  0  0  0
  8  9  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 21  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 19 22  1  0  0  0  0
 20 21  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0047467

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO4/c19-14-6-1-12(2-7-14)3-10-17(22)18-11-16(21)13-4-8-15(20)9-5-13/h1-10,16,19-21H,11H2,(H,18,22)/b10-3+

> <INCHI_KEY>
VATOSFCFMOPAHX-XCVCLJGOSA-N

> <FORMULA>
C17H17NO4

> <MOLECULAR_WEIGHT>
299.3212

> <EXACT_MASS>
299.115758037

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
31.976016215083124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide

> <ALOGPS_LOGP>
1.72

> <JCHEM_LOGP>
2.0398272439999996

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.747615234626899

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.144032638908278

> <JCHEM_PKA_STRONGEST_BASIC>
1.1087055393622485

> <JCHEM_POLAR_SURFACE_AREA>
89.79

> <JCHEM_REFRACTIVITY>
84.3157

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-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      -5.301   1.612   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.536   0.842   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.536  -0.698   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.301  -1.468   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.915  -0.698   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.915   0.842   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.922   1.612   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      -1.144   0.842   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -1.297  -0.698   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.529  -1.468   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.529  -3.008   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.261   1.476   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.414   3.008   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.510   0.577   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.914   1.211   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.164   0.313   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.015  -1.222   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.268  -2.120   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.671  -1.486   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.823   0.046   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.568   0.945   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       7.922  -2.384   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   10                                                  
CONECT    6    1    5                                                       
CONECT    7    2                                                            
CONECT    8    9   12                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9   11                                                  
CONECT   11   10                                                            
CONECT   12    8   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   16   20                                                       
CONECT   22   19                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
4-Coumaroylnoradrenaline	HMDB
p-Coumaroylnoradrenaline	HMDB
(2E)-N-[2-Hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxyphenyl)prop-2-enimidate	Generator

Chemical Formula

C₁₇H₁₇NO₄

Average Mass

299.3212 Da

Monoisotopic Mass

299.11576 Da

IUPAC Name

(2E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide

Traditional Name

(2E)-N-[2-hydroxy-2-(4-hydroxyphenyl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide

CAS Registry Number

66648-45-1

SMILES

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

InChI Identifier

InChI=1S/C17H17NO4/c19-14-6-1-12(2-7-14)3-10-17(22)18-11-16(21)13-4-8-15(20)9-5-13/h1-10,16,19-21H,11H2,(H,18,22)/b10-3+

InChI Key

VATOSFCFMOPAHX-XCVCLJGOSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Capsicum annuum var. annuum	Plant	KNApSAcK
Solanum melongena	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Carboxamide group
Secondary alcohol
Secondary carboxylic acid amide
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Alcohol
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic alcohol
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	1.72	ALOGPS
logP	2.04	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	9.14	ChemAxon
pKa (Strongest Basic)	1.11	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	89.79 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	84.32 m³·mol⁻¹	ChemAxon
Polarizability	31.98 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

HMDB0032804

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010778

KNApSAcK ID

Not Available

Chemspider ID

23550803

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23874492

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for N-trans-p-Coumaroyloctopamine (NP0047467)

MOL for NP0047467 (N-trans-p-Coumaroyloctopamine)

3D MOL for NP0047467 (N-trans-p-Coumaroyloctopamine)

3D SDF for NP0047467 (N-trans-p-Coumaroyloctopamine)

3D-SDF for NP0047467 (N-trans-p-Coumaroyloctopamine)

PDB for NP0047467 (N-trans-p-Coumaroyloctopamine)

3D PDB for NP0047467 (N-trans-p-Coumaroyloctopamine)

SMILES for NP0047467 (N-trans-p-Coumaroyloctopamine)

INCHI for NP0047467 (N-trans-p-Coumaroyloctopamine)

Structure for NP0047467 (N-trans-p-Coumaroyloctopamine)

3D Structure for NP0047467 (N-trans-p-Coumaroyloctopamine)