NP-MRD: Showing NP-Card for Arachidonoyl serinol (NP0339383)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 21:33:35 UTC

Updated at

2024-09-11 21:33:36 UTC

NP-MRD ID

NP0339383

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Arachidonoyl serinol

Description

Arachidonoyl Serinol belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. Thus, arachidonoyl serinol is considered to be a fatty amide lipid molecule. Arachidonoyl Serinol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Arachidonoyl glycerol (2-AG) has been isolated from porcine brain, and has been characterized as the natural endocannabinoid ligand for the CB1 receptor (PMID: 8954083 , 9399597 ). Replacement of the sn-2 oxygen in the glycerol moiety of 2-AG with a nitrogen atom gives arachidonoyl serinol (PMID: 8893848 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02271200292D          

 27 26  0  0  0  0            999 V2000
    9.0763  -10.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9014  -10.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139  -11.5566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1389  -11.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515  -12.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765  -12.2712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515  -10.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765  -10.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139  -10.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1389  -10.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515   -9.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765   -9.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7890   -8.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3771   -7.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5521   -7.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1395   -7.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765   -6.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7884   -5.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3759   -5.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5509   -5.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1389   -4.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5509   -3.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3759   -3.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7877   -2.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6116   -2.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0235   -2.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END


  Mrv0541 02271200292D          

 27 26  0  0  0  0            999 V2000
    9.0763  -10.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9014  -10.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139  -11.5566    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1389  -11.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515  -12.2712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765  -12.2712    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515  -10.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765  -10.8420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3139  -10.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1389  -10.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515   -9.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765   -9.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7890   -8.6987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3771   -7.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5521   -7.9835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1395   -7.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5515   -6.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3765   -6.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7884   -5.8390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3759   -5.1243    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5509   -5.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1389   -4.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5509   -3.6944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3759   -3.6926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7877   -2.9779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6116   -2.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0235   -2.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  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  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  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
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339383

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NC(CO)CO

> <INCHI_IDENTIFIER>
InChI=1S/C23H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(27)24-22(20-25)21-26/h6-7,9-10,12-13,15-16,22,25-26H,2-5,8,11,14,17-21H2,1H3,(H,24,27)/b7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
QHELXIATGZYOIB-DOFZRALJSA-N

> <FORMULA>
C23H39NO3

> <MOLECULAR_WEIGHT>
377.5607

> <EXACT_MASS>
377.292994119

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
45.31883375417432

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z)-N-(1,3-dihydroxypropan-2-yl)icosa-5,8,11,14-tetraenamide

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
4.683467309000001

> <ALOGPS_LOGS>
-5.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.738556460778891

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.82357253696766

> <JCHEM_PKA_STRONGEST_BASIC>
-0.26695465114214023

> <JCHEM_POLAR_SURFACE_AREA>
69.56

> <JCHEM_REFRACTIVITY>
118.9277

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
AA dihydroxypropylamine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0      16.942 -20.238   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      18.483 -20.238   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0      19.253 -21.572   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      20.793 -21.572   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.563 -22.906   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      23.103 -22.906   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      21.563 -20.238   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      23.103 -20.238   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      19.253 -18.904   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.793 -18.904   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.563 -17.571   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.103 -17.571   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.873 -16.238   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.104 -14.904   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.564 -14.903   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      20.794 -13.568   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      21.563 -12.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.103 -12.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.872 -10.899   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.102  -9.565   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      21.562  -9.563   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.793  -8.230   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.562  -6.896   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      23.102  -6.893   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.870  -5.559   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      25.408  -5.557   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      26.177  -4.223   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7                                                            
CONECT    9    2   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   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

View in JSmol

Synonyms

Value	Source
N-[(2-Hydroxy-1-hydroxymethyl)ethyl]-5Z,8Z,11Z,14Z-eicosatetraenamide	HMDB

Chemical Formula

C₂₃H₃₉NO₃

Average Mass

377.5607 Da

Monoisotopic Mass

377.29299 Da

IUPAC Name

(5Z,8Z,11Z,14Z)-N-(1,3-dihydroxypropan-2-yl)icosa-5,8,11,14-tetraenamide

Traditional Name

AA dihydroxypropylamine

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NC(CO)CO

InChI Identifier

InChI=1S/C23H39NO3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(27)24-22(20-25)21-26/h6-7,9-10,12-13,15-16,22,25-26H,2-5,8,11,14,17-21H2,1H3,(H,24,27)/b7-6-,10-9-,13-12-,16-15-

InChI Key

QHELXIATGZYOIB-DOFZRALJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

N-acyl amines

Alternative Parents

Substituents

N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-acyl amines (LMFA08020072 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.35	ALOGPS
logP	4.68	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.82	ChemAxon
pKa (Strongest Basic)	-0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.56 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	118.93 m³·mol⁻¹	ChemAxon
Polarizability	45.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013650

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029620

KNApSAcK ID

Not Available

Chemspider ID

8771144

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10595770

PDB ID

Not Available

ChEBI ID

332319

Good Scents ID

Not Available

References

General References

Showing NP-Card for Arachidonoyl serinol (NP0339383)

MOL for NP0339383 (Arachidonoyl serinol)

3D MOL for NP0339383 (Arachidonoyl serinol)

3D SDF for NP0339383 (Arachidonoyl serinol)

3D-SDF for NP0339383 (Arachidonoyl serinol)

PDB for NP0339383 (Arachidonoyl serinol)

3D PDB for NP0339383 (Arachidonoyl serinol)

SMILES for NP0339383 (Arachidonoyl serinol)

INCHI for NP0339383 (Arachidonoyl serinol)

Structure for NP0339383 (Arachidonoyl serinol)

3D Structure for NP0339383 (Arachidonoyl serinol)