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Showing NP-Card for Stearoylethanolamide (NP0339183)

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Record Information
Version2.0
Created at2024-09-11 20:13:07 UTC
Updated at2024-09-11 20:13:08 UTC
NP-MRD IDNP0339183
Secondary Accession NumbersNone
Natural Product Identification
Common NameStearoylethanolamide
DescriptionStearoylethanolamide, also known as stearamide mea or stearoyl-ea, 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. Thus, stearoylethanolamide is considered to be a fatty amide lipid molecule. Stearoylethanolamide is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339183 (Stearoylethanolamide)


  Mrv0541 02251208162D          

 23 22  0  0  0  0            999 V2000
    6.3282  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0426  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7571  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4716  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1861  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9005  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6151  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3295  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0440  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7585  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4729  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1874  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9019  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6164  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3309  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0453  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7598  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4743  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1888  -15.7227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4743  -14.4851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7598  -14.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7598  -13.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0453  -12.8351    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
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3D MOL for NP0339183 (Stearoylethanolamide)

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3D SDF for NP0339183 (Stearoylethanolamide)

  Mrv0541 02251208162D          

 23 22  0  0  0  0            999 V2000
    6.3282  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0426  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7571  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4716  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1861  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9005  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6151  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3295  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0440  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7585  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4729  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1874  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9019  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6164  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3309  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0453  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7598  -15.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4743  -15.3102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1888  -15.7227    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4743  -14.4851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7598  -14.0726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7598  -13.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0453  -12.8351    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  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  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339183

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCCCC(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23)

> <INCHI_KEY>
OTGQIQQTPXJQRG-UHFFFAOYSA-N

> <FORMULA>
C20H41NO2

> <MOLECULAR_WEIGHT>
327.545

> <EXACT_MASS>
327.313729561

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
44.340895704078925

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-(2-hydroxyethyl)octadecanamide

> <ALOGPS_LOGP>
6.67

> <JCHEM_LOGP>
5.872351547666668

> <ALOGPS_LOGS>
-5.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.451677713180988

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.463162762508802

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3259293688166086

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
99.29679999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.54e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
stearoyl-ethanolamine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339183 (Stearoylethanolamide)
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PDB for NP0339183 (Stearoylethanolamide)
HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      11.813 -29.349   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.146 -28.579   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.480 -29.349   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.814 -28.579   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.147 -29.349   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.481 -28.579   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.815 -29.349   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.148 -28.579   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      22.482 -29.349   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.816 -28.579   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.149 -29.349   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.483 -28.579   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.817 -29.349   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.151 -28.579   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      30.484 -29.349   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      31.818 -28.579   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.152 -29.349   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      34.485 -28.579   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      35.819 -29.349   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      34.485 -27.039   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      33.152 -26.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      33.152 -24.729   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      31.818 -23.959   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                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

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3D PDB for NP0339183 (Stearoylethanolamide)
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SMILES for NP0339183 (Stearoylethanolamide)
CCCCCCCCCCCCCCCCCC(=O)NCCO
Download
INCHI for NP0339183 (Stearoylethanolamide)
InChI=1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23)
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Synonyms
ValueSource
Monoethanolamine stearic acid amideChEBI
N-(2-Hydroxyethyl)stearamideChEBI
N-(Hydroxyethyl)stearamideChEBI
N-(Otadecanoyl)-ethanolamineChEBI
N-Octadecanoyl ethanolamineChEBI
N-OctadecanoylethanolamineChEBI
N-StearoylethanolamineChEBI
Stearamide meaChEBI
Stearic acid monoethanolamideChEBI
Stearic ethanolamideChEBI
Stearic monoethanolamideChEBI
Stearoyl ethanolamideChEBI
Stearoyl-eaChEBI
Stearoyl-ethanolamineChEBI
StearoylmonoethanolamideChEBI
Monoethanolamine stearate amideGenerator
Stearate monoethanolamideGenerator
N-(2-Hydroxyethyl)stearoylamideHMDB
StearoylethanolamideChEBI
Chemical FormulaC20H41NO2
Average Mass327.5450 Da
Monoisotopic Mass327.31373 Da
IUPAC NameN-(2-hydroxyethyl)octadecanamide
Traditional Namestearoyl-ethanolamine
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)NCCO
InChI Identifier
InChI=1S/C20H41NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h22H,2-19H2,1H3,(H,21,23)
InChI KeyOTGQIQQTPXJQRG-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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
    • 

  • Fatty amide
    • 

  • N-acyl-amine
    • 

  • Fatty acyl
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid derivative
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Primary alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP6.67ALOGPS
logP5.87ChemAxon
logS-6ALOGPS
pKa (Strongest Acidic)15.46ChemAxon
pKa (Strongest Basic)-0.33ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity99.3 m³·mol⁻¹ChemAxon
Polarizability44.34 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013078  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029286  
KNApSAcK IDNot Available
Chemspider ID25958  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkStearoylethanolamide  
METLIN IDNot Available
PubChem Compound27902  
PDB IDNot Available
ChEBI ID85299  
Good Scents IDNot Available
References
General References