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Showing NP-Card for Oleoyl glycine (NP0339373)

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Record Information
Version2.0
Created at2024-09-11 21:30:52 UTC
Updated at2024-09-11 21:30:52 UTC
NP-MRD IDNP0339373
Secondary Accession NumbersNone
Natural Product Identification
Common NameOleoyl glycine
DescriptionOleoyl glycine, also known as elmiric acid or EMA-1, belongs to the class of organic compounds known as n-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. Thus, oleoyl glycine is considered to be a fatty amide lipid molecule. N-oleoyl glycine is an acylglycine with oleoic acid (C18:1(9Z))moiety attached to glycine molecule. Oleoyl glycine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Oleoyl glycine was first documented in 2004 (PMID: 15449956). The enzyme was specific for glycine as an acceptor molecule (PMID: 17085322).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0339373 (Oleoyl glycine)


  Mrv1652303102016522D          

 24 23  0  0  0  0            999 V2000
    6.6517   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3662  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0807   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7951  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5096   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2241  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9386   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6531  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3675   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0820   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7965  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5109   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2255  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9399   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6544  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3689   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0834  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7978   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7978   -8.7811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5123  -10.0186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2268   -9.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9412  -10.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6557   -9.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9413  -10.8435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 22  2  0  0  0  0
M  END
Download

3D MOL for NP0339373 (Oleoyl glycine)

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3D SDF for NP0339373 (Oleoyl glycine)

  Mrv1652303102016522D          

 24 23  0  0  0  0            999 V2000
    6.6517   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3662  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0807   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7951  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5096   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2241  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9386   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6531  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3675   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0820   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7965  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5109   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2255  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9399   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6544  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3689   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0834  -10.0186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7978   -9.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7978   -8.7811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5123  -10.0186    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2268   -9.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9412  -10.0185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6557   -9.6059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9413  -10.8435    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
 24 22  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339373

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCC\C=C/CCCCCCCC(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)/b10-9-

> <INCHI_KEY>
HPFXACZRFJDURI-KTKRTIGZSA-N

> <FORMULA>
C20H37NO3

> <MOLECULAR_WEIGHT>
339.5127

> <EXACT_MASS>
339.277344055

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
42.702558917864096

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-[(9Z)-octadec-9-enamido]acetic acid

> <ALOGPS_LOGP>
6.68

> <JCHEM_LOGP>
5.678515211333333

> <ALOGPS_LOGS>
-6.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.018755584127888

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.046618031811936

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6781963756507396

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
100.20569999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.47e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-oleoyl glycine

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339373 (Oleoyl glycine)
Download
PDB for NP0339373 (Oleoyl glycine)
HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0      12.417 -17.931   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.750 -18.701   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      15.084 -17.931   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.418 -18.701   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      17.751 -17.931   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.085 -18.701   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      20.419 -17.931   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.752 -18.701   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      23.086 -17.931   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.420 -17.931   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      25.753 -18.701   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.087 -17.931   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      28.421 -18.701   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.754 -17.931   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      31.088 -18.701   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      32.422 -17.931   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      33.756 -18.701   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      35.089 -17.931   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      35.089 -16.391   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      36.423 -18.701   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      37.757 -17.931   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      39.090 -18.701   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      40.424 -17.931   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      39.090 -20.241   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   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

Download
3D PDB for NP0339373 (Oleoyl glycine)
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SMILES for NP0339373 (Oleoyl glycine)
CCCCCCCC\C=C/CCCCCCCC(=O)NCC(O)=O
Download
INCHI for NP0339373 (Oleoyl glycine)
InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)/b10-9-
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View in JSmol
Synonyms
ValueSource
Elmiric acidChEBI
EMA-1ChEBI
N-(9Z-Octadecenoyl)-glycineChEBI
ElmirateGenerator
(Z)-N-(1-oxo-9-Octadecenyl)glycineHMDB
Acylglycine 18:1(9Z)HMDB
NO-GlyHMDB
N-OleoylglycineMeSH
Chemical FormulaC20H37NO3
Average Mass339.5127 Da
Monoisotopic Mass339.27734 Da
IUPAC Name2-[(9Z)-octadec-9-enamido]acetic acid
Traditional NameN-oleoyl glycine
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C20H37NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h9-10H,2-8,11-18H2,1H3,(H,21,22)(H,23,24)/b10-9-
InChI KeyHPFXACZRFJDURI-KTKRTIGZSA-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-acyl-alpha amino acids. N-acyl-alpha amino acids are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassCarboxylic acids and derivatives  
Sub ClassAmino acids, peptides, and analogues  
Direct ParentN-acyl-alpha amino acids  
Alternative Parents
Substituents
  • N-acyl-alpha-amino acid
    • 

  • Fatty amide
    • 

  • N-acyl-amine
    • 

  • Fatty acyl
    • 

  • Carboxamide group
    • 

  • Secondary carboxylic acid amide
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carbonyl group
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • 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
logP6.68ALOGPS
logP5.68ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)4.05ChemAxon
pKa (Strongest Basic)-1.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity100.21 m³·mol⁻¹ChemAxon
Polarizability42.7 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013631  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029608  
KNApSAcK IDNot Available
Chemspider ID4941514  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6436908  
PDB IDNot Available
ChEBI ID73723  
Good Scents IDNot Available
References
General References
  1. Merkler DJ, Chew GH, Gee AJ, Merkler KA, Sorondo JP, Johnson ME: Oleic acid derived metabolites in mouse neuroblastoma N18TG2 cells. Biochemistry. 2004 Oct 5;43(39):12667-74. doi: 10.1021/bi049529p. [PubMed:15449956  ] 
  2. Chaturvedi S, Driscoll WJ, Elliot BM, Faraday MM, Grunberg NE, Mueller GP: In vivo evidence that N-oleoylglycine acts independently of its conversion to oleamide. Prostaglandins Other Lipid Mediat. 2006 Dec;81(3-4):136-49. doi:  10.1016/j.prostaglandins.2006.09.001. Epub 2006 Oct 5. [PubMed:17085322  ]