MiMeDB: Showing metabocard for N-Linoleoylglycine (MMDBc0000747)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:54:06 UTC

Update Date

2022-08-31 06:11:52 UTC

Metabolite ID

MMDBc0000747

Metabolite Identification

Common Name

N-Linoleoylglycine

Description

2-{[(9Z,12Z)-1-hydroxyoctadeca-9,12-dien-1-ylidene]amino}acetic acid 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. 2-{[(9Z,12Z)-1-hydroxyoctadeca-9,12-dien-1-ylidene]amino}acetic acid is a moderately basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304041918092D          

 24 23  0  0  0  0            999 V2000
   -1.2375    6.4302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    5.7158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    5.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    4.2868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    1.4289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    0.0000    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  2  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
 19 17  1  0  0  0  0
 20 18  1  0  0  0  0
 21 18  1  4  0  0  0
 21 19  2  0  0  0  0
 22 19  1  0  0  0  0
 23 20  2  0  0  0  0
 24 20  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000747

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h6-7,9-10H,2-5,8,11-18H2,1H3,(H,21,22)(H,23,24)/b7-6-,10-9-

> <INCHI_KEY>
YCRHZEHWEYAHCO-HZJYTTRNSA-N

> <FORMULA>
C20H35NO3

> <MOLECULAR_WEIGHT>
337.504

> <EXACT_MASS>
337.261693991

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
41.309024134907986

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-{[(9Z,12Z)-1-hydroxyoctadeca-9,12-dien-1-ylidene]amino}acetic acid

> <ALOGPS_LOGP>
6.49

> <JCHEM_LOGP>
6.042481026982514

> <ALOGPS_LOGS>
-6.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
6.166623412590659

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.094491441856118

> <JCHEM_PKA_STRONGEST_BASIC>
2.1029684025488655

> <JCHEM_POLAR_SURFACE_AREA>
69.89

> <JCHEM_REFRACTIVITY>
101.84399999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.44e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{[(9Z,12Z)-1-hydroxyoctadeca-9,12-dien-1-ylidene]amino}acetic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-APR-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-APR-19         0                                  
HETATM    1  C   UNK     0      -2.310  12.003   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.080  10.669   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.310   9.336   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.080   8.002   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.310   6.668   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.080   5.335   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.310   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.310   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.540   5.335   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310   6.668   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.850   6.668   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.620   5.335   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.160   5.335   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.780   2.667   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.550   1.334   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       9.240   2.667   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       9.240   5.335   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.090   1.334   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.780   0.000   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   19                                                       
CONECT   18   20   21                                                       
CONECT   19   17   21   22                                                  
CONECT   20   18   23   24                                                  
CONECT   21   18   19                                                       
CONECT   22   19                                                            
CONECT   23   20                                                            
CONECT   24   20                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

Synonyms

Value	Source
2-{[(9Z,12Z)-1-hydroxyoctadeca-9,12-dien-1-ylidene]amino}acetate	Generator

Molecular Formula

C₂₀H₃₅NO₃

Average Mass

337.504

Monoisotopic Mass

337.261693991

IUPAC Name

2-{[(9Z,12Z)-1-hydroxyoctadeca-9,12-dien-1-ylidene]amino}acetic acid

Traditional Name

{[(9Z,12Z)-1-hydroxyoctadeca-9,12-dien-1-ylidene]amino}acetic acid

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(O)=NCC(O)=O

InChI Identifier

InChI=1S/C20H35NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19(22)21-18-20(23)24/h6-7,9-10H,2-5,8,11-18H2,1H3,(H,21,22)(H,23,24)/b7-6-,10-9-

InChI Key

YCRHZEHWEYAHCO-HZJYTTRNSA-N

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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

N-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 Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00024 g/L	ALOGPS
logP	6.49	ALOGPS
logP	6.04	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	4.09	ChemAxon
pKa (Strongest Basic)	2.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.89 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	101.84 m³·mol⁻¹	ChemAxon
Polarizability	41.31 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Bacteroidetes	1	Human feces; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	1	Human vaginal fluid; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	2	Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0240344

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6433346

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Showing metabocard for N-Linoleoylglycine (MMDBc0000747)

MOL for #<Metabolite:0x00007fdb19c18940>

3D MOL for #<Metabolite:0x00007fdb19c18940>

3D SDF for #<Metabolite:0x00007fdb19c18940>

3D-SDF for #<Metabolite:0x00007fdb19c18940>

PDB for #<Metabolite:0x00007fdb19c18940>

3D PDB for #<Metabolite:0x00007fdb19c18940>

SMILES for #<Metabolite:0x00007fdb19c18940>

INCHI for #<Metabolite:0x00007fdb19c18940>

Structure for #<Metabolite:0x00007fdb19c18940>

3D Structure for #<Metabolite:0x00007fdb19c18940>