NP-MRD: Showing NP-Card for cis-N-(p-Coumaroyl)serotonin (NP0068968)

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Record Information

Version

2.0

Created at

2022-04-28 14:14:54 UTC

Updated at

2022-04-28 14:14:54 UTC

NP-MRD ID

NP0068968

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cis-N-(p-Coumaroyl)serotonin

Description

ZINC5553933 belongs to the class of organic compounds known as n-acylserotonins. These are aromatic heterocyclic compounds containing a serotonin, in which the amine group is acylated. cis-N-(p-Coumaroyl)serotonin is found in Amorphophallus konjac, Amorphophallus konjac K.Koch and Centaurea montana. Based on a literature review very few articles have been published on ZINC5553933.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
   -2.5877   -0.1639   -0.8855 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6573   -0.4393   -0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8265   -0.6161    1.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9348   -0.4580    1.9436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1850   -0.0809    1.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2799   -0.8333    1.8449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5686   -0.5835    1.4975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8241    0.4556    0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1238    0.7338    0.2643 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7654    1.2121    0.1513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4517    0.9535    0.5068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3525   -0.6102   -0.5595 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9024   -0.7746   -0.9765 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8729   -1.2365    0.1407 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2360   -1.2584   -0.4210 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9979   -2.2573   -0.9243 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1976   -1.7437   -1.3408 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1973   -0.4218   -1.1040 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1492    0.5826   -1.3100 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8954    1.8865   -0.9491 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6894    2.2264   -0.3754 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4029    3.5406    0.0063 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7578    1.2154   -0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9888   -0.0884   -0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8949   -0.9017    1.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9566   -0.6131    3.0589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1055   -1.6682    2.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4052   -1.1964    1.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6479    1.3851    0.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9734    2.0340   -0.5328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6567    1.6053    0.1720 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7327   -0.2229   -1.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0099   -1.5820   -1.7865 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4343    0.1174   -1.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6182   -2.2803    0.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7873   -0.6124    1.0227 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7178   -3.2853   -0.9793 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9523   -2.3259   -1.7685 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0778    0.2680   -1.7645 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6228    2.6731   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    3.8798    0.9504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8037    1.4848    0.2652 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  2  0
  7  6  1  0
  6  5  2  0
  5  4  1  0
  4  3  2  0
  3  2  1  0
  2  1  2  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
  5 11  1  0
 11 10  2  0
 10  8  1  0
 24 15  1  0
 24 18  1  0
  9 29  1  0
  7 28  1  0
  6 27  1  0
  4 26  1  0
  3 25  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 17 38  1  0
 19 39  1  0
 20 40  1  0
 22 41  1  0
 23 42  1  0
 11 31  1  0
 10 30  1  0
M  END


  Mrv1652304282216142D          

 24 26  0  0  0  0            999 V2000
   -3.2077    4.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6556    4.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8487    4.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5937    3.7777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457    3.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9527    3.3362    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7332    2.4502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9263    2.6217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8400    3.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1256    3.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5889    3.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3034    3.8547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0178    3.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0178    2.6172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7323    3.8547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4468    3.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4468    2.6172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1613    2.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1613    1.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4468    0.9672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7323    1.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7323    2.2047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4468    0.1422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9106    5.5185    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  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  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  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 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
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 20 23  1  0  0  0  0
  2 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0068968

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C(\C=C/C(=O)NCCC2=CNC3=CC=C(O)C=C23)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H18N2O3/c22-15-4-1-13(2-5-15)3-8-19(24)20-10-9-14-12-21-18-7-6-16(23)11-17(14)18/h1-8,11-12,21-23H,9-10H2,(H,20,24)/b8-3-

> <INCHI_KEY>
WLZPAFGVOWCVMG-BAQGIRSFSA-N

> <FORMULA>
C19H18N2O3

> <MOLECULAR_WEIGHT>
322.364

> <EXACT_MASS>
322.131742448

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
33.88214048799025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide

> <ALOGPS_LOGP>
3.01

> <JCHEM_LOGP>
3.0575853839999994

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.79465929719754

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.181924962662672

> <JCHEM_PKA_STRONGEST_BASIC>
-0.38748250906927384

> <JCHEM_POLAR_SURFACE_AREA>
85.35000000000001

> <JCHEM_REFRACTIVITY>
94.19470000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.62e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-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      -5.988   7.692   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.957   8.837   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.451   8.516   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.975   7.052   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.005   5.907   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.512   6.228   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -3.235   4.574   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -1.729   4.894   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.568   6.425   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.234   7.195   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.099   6.425   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.433   7.195   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.767   6.425   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.767   4.885   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.100   7.195   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.434   6.425   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.434   4.885   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.768   4.115   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.768   2.575   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.434   1.805   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.100   2.575   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.100   4.115   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       6.434   0.265   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.433  10.301   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
CONECT   23   20                                                            
CONECT   24    2                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₁₈N₂O₃

Average Mass

322.3640 Da

Monoisotopic Mass

322.13174 Da

IUPAC Name

(2Z)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide

Traditional Name

(2Z)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide

CAS Registry Number

Not Available

SMILES

OC1=CC=C(\C=C/C(=O)NCCC2=CNC3=CC=C(O)C=C23)C=C1

InChI Identifier

InChI=1S/C19H18N2O3/c22-15-4-1-13(2-5-15)3-8-19(24)20-10-9-14-12-21-18-7-6-16(23)11-17(14)18/h1-8,11-12,21-23H,9-10H2,(H,20,24)/b8-3-

InChI Key

WLZPAFGVOWCVMG-BAQGIRSFSA-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
Amorphophallus konjac	LOTUS Database	35616633
Amorphophallus konjac K.Koch	Plant	KNApSAcK
Centaurea montana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylserotonins. These are aromatic heterocyclic compounds containing a serotonin, in which the amine group is acylated.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

N-acylserotonins

Alternative Parents

Substituents

N-acylserotonin
Cinnamic acid amide
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Hydroxyindole
3-alkylindole
Indole
Styrene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Substituted pyrrole
Heteroaromatic compound
Pyrrole
Carboxamide group
Secondary carboxylic acid amide
Azacycle
Carboxylic acid derivative
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organonitrogen compound
Organooxygen 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	3.01	ALOGPS
logP	3.06	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.18	ChemAxon
pKa (Strongest Basic)	-0.39	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	85.35 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	94.19 m³·mol⁻¹	ChemAxon
Polarizability	33.88 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00027080

Chemspider ID

8556891

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10381448

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for cis-N-(p-Coumaroyl)serotonin (NP0068968)

MOL for NP0068968 (cis-N-(p-Coumaroyl)serotonin)

3D MOL for NP0068968 (cis-N-(p-Coumaroyl)serotonin)

3D SDF for NP0068968 (cis-N-(p-Coumaroyl)serotonin)

3D-SDF for NP0068968 (cis-N-(p-Coumaroyl)serotonin)

PDB for NP0068968 (cis-N-(p-Coumaroyl)serotonin)

3D PDB for NP0068968 (cis-N-(p-Coumaroyl)serotonin)

SMILES for NP0068968 (cis-N-(p-Coumaroyl)serotonin)

INCHI for NP0068968 (cis-N-(p-Coumaroyl)serotonin)

Structure for NP0068968 (cis-N-(p-Coumaroyl)serotonin)

3D Structure for NP0068968 (cis-N-(p-Coumaroyl)serotonin)