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Showing NP-Card for (2e)-n-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid (NP0296360)

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Record Information
Version2.0
Created at2022-09-10 05:53:25 UTC
Updated at2022-09-10 05:53:25 UTC
NP-MRD IDNP0296360
Secondary Accession NumbersNone
Natural Product Identification
Common Name(2e)-n-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid
DescriptionIdrocilamide, also known as srilane or LCB 29, 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. (2e)-n-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid is found in Erythrophleum chlorostachys. (2e)-n-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid was first documented in 2020 (PMID: 32022481). Based on a literature review very few articles have been published on Idrocilamide.
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0296360 ((2e)-n-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid)


  Mrv1652309102207532D          

 14 14  0  0  0  0            999 V2000
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
    0.7145    3.7125    0.0000 N   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
M  END
Download

3D MOL for NP0296360 ((2e)-n-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid)

     RDKit          3D

 27 27  0  0  0  0  0  0  0  0999 V2000
    2.8341    0.7615   -0.8123 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7438   -0.2819   -0.6572 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0569   -1.3462    0.1975 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7321   -0.7268    1.4473 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6053   -0.2430    1.7048 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3282    0.3598    2.9531 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5148   -0.2674    0.7474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6842    0.2453    1.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8090    0.2470    0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0078    0.8146    0.4984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1207    0.8559   -0.3166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0842    0.3272   -1.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8904   -0.2509   -2.0155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7918   -0.2761   -1.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0883    1.5787   -0.3502 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0834   -0.6977   -1.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6138    0.1057   -0.0551 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7981   -2.1666    0.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349   -1.8021   -0.3435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6925    1.2670    3.1852 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5966   -0.6984   -0.2408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7859    0.6828    2.0044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0407    1.2394    1.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0245    1.3188    0.0736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9611    0.3685   -2.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8272   -0.6805   -3.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8955   -0.7348   -1.5587 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  5  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14  9  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
 10 23  1  0
 11 24  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
M  END
Download

3D SDF for NP0296360 ((2e)-n-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid)


  Mrv1652309102207532D          

 14 14  0  0  0  0            999 V2000
    1.4289    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    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
    0.7145    3.7125    0.0000 N   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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  4  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0296360

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCCN=C(O)\C=C\C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H13NO2/c13-9-8-12-11(14)7-6-10-4-2-1-3-5-10/h1-7,13H,8-9H2,(H,12,14)/b7-6+

> <INCHI_KEY>
OSCTXCOERRNGLW-VOTSOKGWSA-N

> <FORMULA>
C11H13NO2

> <MOLECULAR_WEIGHT>
191.23

> <EXACT_MASS>
191.094628663

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
21.43694388665037

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-N-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid

> <JCHEM_LOGP>
1.4044606416927659

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.572722203892702

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.554676666428652

> <JCHEM_PKA_STRONGEST_BASIC>
4.613888041542512

> <JCHEM_POLAR_SURFACE_AREA>
52.82000000000001

> <JCHEM_REFRACTIVITY>
56.59280000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
idrocilamide

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0296360 ((2e)-n-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid)

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PDB for NP0296360 ((2e)-n-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid)
HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  O   UNK     0       2.667  10.780   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0       1.334   6.930   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

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3D PDB for NP0296360 ((2e)-n-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid)
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SMILES for NP0296360 ((2e)-n-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid)
OCCN=C(O)\C=C\C1=CC=CC=C1
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INCHI for NP0296360 ((2e)-n-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid)
InChI=1S/C11H13NO2/c13-9-8-12-11(14)7-6-10-4-2-1-3-5-10/h1-7,13H,8-9H2,(H,12,14)/b7-6+
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View in JSmol
Synonyms
ValueSource
SrilaneKegg
N-(2-Hydroxyethyl)cinnamideMeSH
LCB 29MeSH
BroliteneMeSH
Chemical FormulaC11H13NO2
Average Mass191.2300 Da
Monoisotopic Mass191.09463 Da
IUPAC Name(2E)-N-(2-hydroxyethyl)-3-phenylprop-2-enimidic acid
Traditional Nameidrocilamide
CAS Registry NumberNot Available
SMILES
OCCN=C(O)\C=C\C1=CC=CC=C1
InChI Identifier
InChI=1S/C11H13NO2/c13-9-8-12-11(14)7-6-10-4-2-1-3-5-10/h1-7,13H,8-9H2,(H,12,14)/b7-6+
InChI KeyOSCTXCOERRNGLW-VOTSOKGWSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Erythrophleum chlorostachysLOTUS Database
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.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassCinnamic acids and derivatives  
Sub ClassCinnamic acid amides  
Direct ParentCinnamic acid amides  
Alternative Parents
Substituents
  • Cinnamic acid amide
    • 

  • Styrene
    • 

  • N-acylethanolamine
    • 

  • Monocyclic benzene moiety
    • 

  • Benzenoid
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Alkanolamine
    • 

  • Carboxylic acid derivative
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Primary alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.4ChemAxon
pKa (Strongest Acidic)6.55ChemAxon
pKa (Strongest Basic)4.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area52.82 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity56.59 m³·mol⁻¹ChemAxon
Polarizability21.44 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1267352  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIdrocilamide  
METLIN IDNot Available
PubChem Compound1550874  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Dufrenoy P, Charlet R, Hechelski M, Daich A, Waterlot C, Jawhara S, Ghinet A: New Efficient Eco-Friendly Supported Catalysts for the Synthesis of Amides with Antioxidant and Anti-Inflammatory Properties. ChemMedChem. 2020 Mar 5;15(5):459-467. doi: 10.1002/cmdc.201900641. Epub 2020 Feb  12. [PubMed:32022481  ] 
  2. LOTUS database [Link]