NP-MRD: Showing NP-Card for N-trans-Cinnamoyltyramine (NP0069021)

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Record Information

Version

2.0

Created at

2022-04-28 14:17:23 UTC

Updated at

2022-04-28 14:17:24 UTC

NP-MRD ID

NP0069021

Secondary Accession Numbers

None

Natural Product Identification

Common Name

N-trans-Cinnamoyltyramine

Description

N-trans-cinnamoyltyramine belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid. N-trans-Cinnamoyltyramine is found in Aristolochia cucurbitifolia, Aristolochia elegans and Phellodendron japonicum MAXIM. N-trans-Cinnamoyltyramine was first documented in 2002 (PMID: 12579800). Based on a literature review a small amount of articles have been published on N-trans-cinnamoyltyramine (PMID: 14643446) (PMID: 17319684) (PMID: 21128731) (PMID: 25212867).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
   -0.1266   -1.9327   -0.4038 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5769   -0.9490   -0.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0223   -1.0411   -0.1572 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881   -0.1150    0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3247   -0.2851    0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1532    0.7597    0.4237 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5105    0.6877    0.2983 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0864   -0.4468   -0.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3146   -1.5055   -0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9255   -1.3955   -0.5138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0043    0.2058    0.5342 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4332    0.3070    0.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0641    0.2252   -0.6920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5641    0.3365   -0.5689 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1780    1.5709   -0.6193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5537    1.6559   -0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3485    0.5413   -0.3402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7267    0.6002   -0.2234 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7325   -0.7060   -0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3588   -0.7787   -0.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4109   -1.9526   -0.5873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4978    0.8227    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7001    1.6439    0.8459 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1725    1.4993    0.6116 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1570   -0.4855   -0.3340 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7498   -2.3999   -1.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3220   -2.2180   -0.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5683    0.9947    0.8478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7311    1.2945    1.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8556   -0.5308    1.2706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8776   -0.7183   -1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7749    1.1046   -1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5718    2.4663   -0.7488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0101    2.6412   -0.5482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2452    1.4504   -0.2497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3581   -1.5928   -0.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8657   -1.7549   -0.3648 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  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
 14 20  1  0
 20 19  2  0
 19 17  1  0
 10  5  1  0
 18 35  1  0
 16 34  1  0
 15 33  1  0
 13 31  1  0
 13 32  1  0
 12 29  1  0
 12 30  1  0
 11 28  1  0
  3 21  1  0
  4 22  1  0
  6 23  1  0
  7 24  1  0
  8 25  1  0
  9 26  1  0
 10 27  1  0
 20 37  1  0
 19 36  1  0
M  END


  Mrv1652304282216172D          

 20 21  0  0  0  0            999 V2000
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 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
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
  2 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069021

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(CCNC(=O)\C=C\C2=CC=CC=C2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H17NO2/c19-16-9-6-15(7-10-16)12-13-18-17(20)11-8-14-4-2-1-3-5-14/h1-11,19H,12-13H2,(H,18,20)/b11-8+

> <INCHI_KEY>
KGOYCHSKGXJDND-DHZHZOJOSA-N

> <FORMULA>
C17H17NO2

> <MOLECULAR_WEIGHT>
267.328

> <EXACT_MASS>
267.125928791

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
30.054428722719255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.2623887126666666

> <ALOGPS_LOGS>
-4.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.11557198622256

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.504587376755673

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3876776460311061

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
81.12730000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.73e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-[2-(4-hydroxyphenyl)ethyl]-3-phenylprop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.001  -8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667  -6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.667  -6.160   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.001  -8.470   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.336  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
(2E)-N-[2-(4-Hydroxyphenyl)ethyl]-3-phenyl-2-propenamide	ChEBI
(e)-N-[2-(4-Hydroxyphenyl)ethyl]-3-phenyl-2-propenamide	ChEBI
Cinnamoyltyramine	ChEBI
N-Cinnamoyltyramine	ChEBI
trans-Cinnamoyl-p-hydroxybenzenethylamine	ChEBI

Chemical Formula

C₁₇H₁₇NO₂

Average Mass

267.3280 Da

Monoisotopic Mass

267.12593 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

OC1=CC=C(CCNC(=O)\C=C\C2=CC=CC=C2)C=C1

InChI Identifier

InChI=1S/C17H17NO2/c19-16-9-6-15(7-10-16)12-13-18-17(20)11-8-14-4-2-1-3-5-14/h1-11,19H,12-13H2,(H,18,20)/b11-8+

InChI Key

KGOYCHSKGXJDND-DHZHZOJOSA-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
Aristolochia cucurbitifolia	LOTUS Database	35616633
Aristolochia elegans	Plant	KNApSAcK
Phellodendron japonicum MAXIM	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid amides. These are amides of cinnamic acids. Cinnamic acid is an aromatic compound containing a benzene and a carboxylic acid group forming 3-phenylprop-2-enoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid amides

Direct Parent

Cinnamic acid amides

Alternative Parents

Substituents

Cinnamic acid amide
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Organic nitrogen 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	3.01	ALOGPS
logP	3.26	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	9.5	ChemAxon
pKa (Strongest Basic)	-0.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.13 m³·mol⁻¹	ChemAxon
Polarizability	30.05 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

Not Available

KNApSAcK ID

C00027156

Chemspider ID

4475103

KEGG Compound ID

Not Available

BioCyc ID

CPD-8941

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5315911

PDB ID

Not Available

ChEBI ID

177872

Good Scents ID

Not Available

References

General References

Park JB, Schoene N: N-Caffeoyltyramine arrests growth of U937 and Jurkat cells by inhibiting protein tyrosine phosphorylation and inducing caspase-3. Cancer Lett. 2003 Dec 30;202(2):161-71. doi: 10.1016/j.canlet.2003.08.010. [PubMed:14643446 ]
Yang GZ, Zhao S, Li YC: [Studies on the chemical constituents of Lycianthes biflora]. Yao Xue Xue Bao. 2002 Jun;37(6):437-9. [PubMed:12579800 ]
Park JB: Caffedymine from cocoa has COX inhibitory activity suppressing the expression of a platelet activation marker, P-selectin. J Agric Food Chem. 2007 Mar 21;55(6):2171-5. doi: 10.1021/jf0628835. Epub 2007 Feb 24. [PubMed:17319684 ]
Yang Y, Song ZG, Liu ZQ: Synthesis and antioxidant capacities of hydroxyl derivatives of cinnamoylphenethylamine in protecting DNA and scavenging radicals. Free Radic Res. 2011 Apr;45(4):445-53. doi: 10.3109/10715762.2010.540576. Epub 2010 Dec 3. [PubMed:21128731 ]
Le Thi H, Lin CH, Smeda RJ, Leigh ND, Wycoff WG, Fritschi FB: Isolation and identification of an allelopathic phenylethylamine in rice. Phytochemistry. 2014 Dec;108:109-21. doi: 10.1016/j.phytochem.2014.08.019. Epub 2014 Sep 8. [PubMed:25212867 ]

Showing NP-Card for N-trans-Cinnamoyltyramine (NP0069021)

MOL for NP0069021 (N-trans-Cinnamoyltyramine)

3D MOL for NP0069021 (N-trans-Cinnamoyltyramine)

3D SDF for NP0069021 (N-trans-Cinnamoyltyramine)

3D-SDF for NP0069021 (N-trans-Cinnamoyltyramine)

PDB for NP0069021 (N-trans-Cinnamoyltyramine)

3D PDB for NP0069021 (N-trans-Cinnamoyltyramine)

SMILES for NP0069021 (N-trans-Cinnamoyltyramine)

INCHI for NP0069021 (N-trans-Cinnamoyltyramine)

Structure for NP0069021 (N-trans-Cinnamoyltyramine)

3D Structure for NP0069021 (N-trans-Cinnamoyltyramine)