Np mrd loader

Showing NP-Card for Entadamide A (NP0072076)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2022-04-28 17:27:20 UTC
Updated at2022-04-28 17:27:20 UTC
NP-MRD IDNP0072076
Secondary Accession NumbersNone
Natural Product Identification
Common NameEntadamide A
DescriptionEntadamide A belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine. Entadamide A is found in Clinacanthus nutans, Clinacanthus siamensis and Entada phaseoloides . Entadamide A was first documented in 2014 (PMID: 25490430). Based on a literature review a small amount of articles have been published on Entadamide A (PMID: 34424556) (PMID: 26390638) (PMID: 31696379) (PMID: 30635249).
Structure
Thumb
MOL3D MOLSDFPDBSMILESInChI

MOL for NP0072076 (Entadamide A)


  Mrv1652304282219272D          

 10  9  0  0  0  0            999 V2000
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
M  END
Download

3D MOL for NP0072076 (Entadamide A)

     RDKit          3D

 21 20  0  0  0  0  0  0  0  0999 V2000
    4.8129   -1.0404   -0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5853   -0.1367   -1.0472 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.9135   -0.5264   -0.5343 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0373    0.4325   -0.2858 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3349    0.1414    0.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7030   -1.0450    0.2667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2399    1.1835    0.3905 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6036    1.0478    0.7984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5091    0.3410   -0.1644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1341   -0.9573   -0.4434 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4547   -2.0045    0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1370   -0.3720    0.7486 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7427   -1.2133   -0.6892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5646   -1.5530   -0.4109 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3675    1.4502   -0.4034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8542    2.1771    0.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499    0.4288    1.7500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0332    2.0339    1.1248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5243    0.8982   -1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5549    0.3232    0.2087 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4743   -1.6090    0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  1 11  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  4 15  1  0
  7 16  1  0
  8 17  1  0
  8 18  1  0
  9 19  1  0
  9 20  1  0
 10 21  1  0
M  END
Download

3D SDF for NP0072076 (Entadamide A)


  Mrv1652304282219272D          

 10  9  0  0  0  0            999 V2000
   -2.3349    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    0.7145    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  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
M  END
> <DATABASE_ID>
NP0072076

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CS\C=C\C(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C6H11NO2S/c1-10-5-2-6(9)7-3-4-8/h2,5,8H,3-4H2,1H3,(H,7,9)/b5-2+

> <INCHI_KEY>
NBRCIHAGNJRRRI-GORDUTHDSA-N

> <FORMULA>
C6H11NO2S

> <MOLECULAR_WEIGHT>
161.22

> <EXACT_MASS>
161.051049772

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.976884277625018

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-N-(2-hydroxyethyl)-3-(methylsulfanyl)prop-2-enamide

> <ALOGPS_LOGP>
-0.33

> <JCHEM_LOGP>
-0.5070151383333328

> <ALOGPS_LOGS>
-1.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.257914554580314

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.346061753944568

> <JCHEM_PKA_STRONGEST_BASIC>
-0.4838864391435379

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
43.151700000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.47e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-N-(2-hydroxyethyl)-3-(methylsulfanyl)prop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0072076 (Entadamide A)

Download
PDB for NP0072076 (Entadamide A)
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      -4.358   2.104   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0      -3.025   1.334   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0       2.310   1.334   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+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                                                       
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END

Download
3D PDB for NP0072076 (Entadamide A)
Download
SMILES for NP0072076 (Entadamide A)
CS\C=C\C(=O)NCCO
Download
INCHI for NP0072076 (Entadamide A)
InChI=1S/C6H11NO2S/c1-10-5-2-6(9)7-3-4-8/h2,5,8H,3-4H2,1H3,(H,7,9)/b5-2+
Download
View in JSmol
Synonyms
ValueSource
N-(2-Hydroxyethyl)-3-methylthiopropenamideMeSH
Chemical FormulaC6H11NO2S
Average Mass161.2200 Da
Monoisotopic Mass161.05105 Da
IUPAC Name(2E)-N-(2-hydroxyethyl)-3-(methylsulfanyl)prop-2-enamide
Traditional Name(2E)-N-(2-hydroxyethyl)-3-(methylsulfanyl)prop-2-enamide
CAS Registry NumberNot Available
SMILES
CS\C=C\C(=O)NCCO
InChI Identifier
InChI=1S/C6H11NO2S/c1-10-5-2-6(9)7-3-4-8/h2,5,8H,3-4H2,1H3,(H,7,9)/b5-2+
InChI KeyNBRCIHAGNJRRRI-GORDUTHDSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Clinacanthus nutansLOTUS Database
Clinacanthus siamensisPlant
Entada phaseoloidesPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.
KingdomOrganic compounds  
Super ClassOrganic nitrogen compounds  
ClassOrganonitrogen compounds  
Sub ClassAmines  
Direct ParentN-acylethanolamines  
Alternative Parents
Substituents
  • N-acylethanolamine
    • 

  • Vinylogous thioester
    • 

  • Acrylic acid or derivatives
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Thioenolether
    • 

  • Carboxylic acid derivative
    • 

  • Sulfenyl compound
    • 

  • Primary alcohol
    • 

  • Organosulfur compound
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Alcohol
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP-0.33ALOGPS
logP-0.51ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)15.35ChemAxon
pKa (Strongest Basic)-0.48ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.15 m³·mol⁻¹ChemAxon
Polarizability16.98 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00031763  
Chemspider ID4943641  
KEGG Compound IDC20204  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6439215  
PDB IDNot Available
ChEBI ID179370  
Good Scents IDNot Available
References
General References
  1. Zhou Y, Shan H, Lu H: Optimization, extraction, and purification of three bioactive compounds from Entada phaseoloides by high-speed countercurrent chromatography. Biomed Chromatogr. 2021 Dec;35(12):e5232. doi: 10.1002/bmc.5232. Epub 2021 Sep 6. [PubMed:34424556  ] 
  2. Shen HP, Wang MY, Li XB: [Quality standard study on Entadae Semen]. Zhongguo Zhong Yao Za Zhi. 2015 May;40(10):1860-4. [PubMed:26390638  ] 
  3. Zamri N, Hamid HA: Comparative Study of Onion (Allium cepa) and Leek (Allium ampeloprasum): Identification of Organosulphur Compounds by UPLC-QTOF/MS and Anticancer Effect on MCF-7 Cells. Plant Foods Hum Nutr. 2019 Dec;74(4):525-530. doi: 10.1007/s11130-019-00770-6. [PubMed:31696379  ] 
  4. Barua CC, Buragohain L, Rizavi H, Gogoi SB, Rahman F, Siva B, Mounika K, Babu KS, Chandra Pathak D, Phukan A: Effect of seeds of Entada phaseoloides on chronic restrain stress in mice. J Ayurveda Integr Med. 2020 Oct-Dec;11(4):464-470. doi: 10.1016/j.jaim.2018.02.140. Epub 2019 Jan 8. [PubMed:30635249  ] 
  5. Tu SF, Liu RH, Cheng YB, Hsu YM, Du YC, El-Shazly M, Wu YC, Chang FR: Chemical constituents and bioactivities of Clinacanthus nutans aerial parts. Molecules. 2014 Dec 5;19(12):20382-90. doi: 10.3390/molecules191220382. [PubMed:25490430  ]