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Showing NP-Card for Palmitoylglycine (NP0334611)

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Record Information
Version2.0
Created at2024-09-10 19:08:17 UTC
Updated at2024-09-10 19:08:17 UTC
NP-MRD IDNP0334611
Secondary Accession NumbersNone
Natural Product Identification
Common NamePalmitoylglycine
DescriptionPalmitoylglycine, also known as elmiric acid or hexadecanoylglycine, 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, palmitoylglycine is considered to be a fatty amide lipid molecule. Palmitoylglycine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Palmitoylglycine was first documented in 2001 (PMID: 11695892). An N-acylglycine in which the acyl group is specified as hexadecanoyl (palmitoyl) (PMID: 12913269) (PMID: 16190718) (PMID: 16201802) (PMID: 16637647).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0334611 (Palmitoylglycine)

140
  Mrv1652303102016492D          

 22 21  0  0  0  0            999 V2000
   -6.6111    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3256   -0.2328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6111    1.0048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8966   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1821    0.1797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4675   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4675   -1.0579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7530    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0385   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3240    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8950    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1804   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5341    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2487   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9631    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6777   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1067   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8213    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5358   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2503    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  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  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
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3D MOL for NP0334611 (Palmitoylglycine)

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3D SDF for NP0334611 (Palmitoylglycine)
140
  Mrv1652303102016492D          

 22 21  0  0  0  0            999 V2000
   -6.6111    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3256   -0.2328    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6111    1.0048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8966   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1821    0.1797    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4675   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4675   -1.0579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7530    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0385   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3240    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8950    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1804   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5341    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2487   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9631    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6777   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3923    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1067   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8213    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5358   -0.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2503    0.1797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  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  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334611

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCCCC(=O)NCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(20)19-16-18(21)22/h2-16H2,1H3,(H,19,20)(H,21,22)

> <INCHI_KEY>
KVTFEOAKFFQCCX-UHFFFAOYSA-N

> <FORMULA>
C18H35NO3

> <MOLECULAR_WEIGHT>
313.4754

> <EXACT_MASS>
313.261693991

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
39.94220924860111

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hexadecanamidoacetic acid

> <ALOGPS_LOGP>
6.18

> <JCHEM_LOGP>
5.151299538

> <ALOGPS_LOGS>
-5.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.99380161601848

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.046618031780419

> <JCHEM_PKA_STRONGEST_BASIC>
-1.678196375539359

> <JCHEM_POLAR_SURFACE_AREA>
66.4

> <JCHEM_REFRACTIVITY>
89.88709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.08e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-palmitoyl glycine

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334611 (Palmitoylglycine)
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PDB for NP0334611 (Palmitoylglycine)
HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 140                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  C   UNK     0     -12.341   0.335   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -13.674  -0.435   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0     -12.341   1.876   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0     -11.007  -0.435   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -9.673   0.335   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -8.339  -0.435   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -8.339  -1.975   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -7.006   0.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.672  -0.435   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.338   0.335   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.004  -0.435   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.671   0.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.337  -0.435   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.997   0.335   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.331  -0.435   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.664   0.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.998  -0.435   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.332   0.335   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.666  -0.435   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.000   0.335   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.333  -0.435   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.667   0.335   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    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                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

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3D PDB for NP0334611 (Palmitoylglycine)
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SMILES for NP0334611 (Palmitoylglycine)
CCCCCCCCCCCCCCCC(=O)NCC(O)=O
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INCHI for NP0334611 (Palmitoylglycine)
InChI=1S/C18H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(20)19-16-18(21)22/h2-16H2,1H3,(H,19,20)(H,21,22)
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Synonyms
ValueSource
2-(Hexadecanoylamino)acetic acidChEBI
2-Hexadecanamidoacetic acidChEBI
Elmiric acidChEBI
HexadecanoylglycineChEBI
N-PalmitoylglycineChEBI
2-(Hexadecanoylamino)acetateGenerator
2-HexadecanamidoacetateGenerator
ElmirateGenerator
N-Ethanoyl-hexadecanamideHMDB
Glycine stearamideHMDB
Glycine steatamideHMDB
N-(1-Oxooctadecyl)-glycineHMDB
N-(Carboxymethyl)octadecanamideHMDB
N-StearoylglycineHMDB
N-Palmitoyl glycineHMDB
PalmitoylglycineChEBI
Chemical FormulaC18H35NO3
Average Mass313.4754 Da
Monoisotopic Mass313.26169 Da
IUPAC Name2-hexadecanamidoacetic acid
Traditional NameN-palmitoyl glycine
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)NCC(O)=O
InChI Identifier
InChI=1S/C18H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17(20)19-16-18(21)22/h2-16H2,1H3,(H,19,20)(H,21,22)
InChI KeyKVTFEOAKFFQCCX-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-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
logP6.18ALOGPS
logP5.15ChemAxon
logS-5.6ALOGPS
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 Count16ChemAxon
Refractivity89.89 m³·mol⁻¹ChemAxon
Polarizability39.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0013034  
DrugBank IDDB03440  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029260  
KNApSAcK IDNot Available
Chemspider ID133100  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound151008  
PDB ID140  
ChEBI ID39540  
Good Scents IDNot Available
References
General References
  1. Haines DC, Tomchick DR, Machius M, Peterson JA: Pivotal role of water in the mechanism of P450BM-3. Biochemistry. 2001 Nov 13;40(45):13456-65. doi: 10.1021/bi011197q. [PubMed:11695892  ] 
  2. Okimura K, Ohki K, Nagai S, Sakura N: HPLC analysis of fatty acyl-glycine in the aqueous methanesulfonic acid hydrolysates of N-terminally fatty acylated peptides. Biol Pharm Bull. 2003 Aug;26(8):1166-9. doi: 10.1248/bpb.26.1166. [PubMed:12913269  ] 
  3. Jovanovic T, Farid R, Friesner RA, McDermott AE: Thermal equilibrium of high- and low-spin forms of cytochrome P450 BM-3: repositioning of the substrate? J Am Chem Soc. 2005 Oct 5;127(39):13548-52. doi: 10.1021/ja0524604. [PubMed:16190718  ] 
  4. Jovanovic T, McDermott AE: Observation of ligand binding to cytochrome P450 BM-3 by means of solid-state NMR spectroscopy. J Am Chem Soc. 2005 Oct 12;127(40):13816-21. doi: 10.1021/ja0438314. [PubMed:16201802  ] 
  5. Ravindranathan KP, Gallicchio E, Friesner RA, McDermott AE, Levy RM: Conformational equilibrium of cytochrome P450 BM-3 complexed with N-palmitoylglycine: a replica exchange molecular dynamics study. J Am Chem Soc. 2006 May 3;128(17):5786-91. doi: 10.1021/ja058465i. [PubMed:16637647  ]