NP-MRD: Showing NP-Card for 11-Hydroxyeicosatetraenoate glyceryl ester (NP0339030)

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Record Information

Version

2.0

Created at

2024-09-11 19:20:42 UTC

Updated at

2024-09-11 19:20:42 UTC

NP-MRD ID

NP0339030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

11-Hydroxyeicosatetraenoate glyceryl ester

Description

11-Hydroxyeicosatetraenoate glyceryl ester, also known as 11-hete-g, belongs to the class of organic compounds known as endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail. 11-Hydroxyeicosatetraenoate glyceryl ester is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208062D          

 28 27  0  0  1  0            999 V2000
   18.1500  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4356  -14.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7211  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0066  -14.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777  -14.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632  -13.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487  -13.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487  -12.3445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4342  -11.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632  -11.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777  -12.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922  -11.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922  -11.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0066  -10.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0066   -9.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922   -9.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922   -8.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777   -8.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777   -7.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922   -6.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632   -6.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487   -7.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4342   -6.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7198   -7.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487   -8.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4342   -8.6320    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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  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  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
M  END


  Mrv0541 02251208062D          

 28 27  0  0  1  0            999 V2000
   18.1500  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4356  -14.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7211  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0066  -14.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777  -14.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632  -14.4070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632  -13.5820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487  -13.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487  -12.3445    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.4342  -11.9320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632  -11.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777  -12.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922  -11.9320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922  -11.1070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0066  -10.6945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0066   -9.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922   -9.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922   -8.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777   -8.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5777   -7.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2922   -6.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8632   -6.9820    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487   -7.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4342   -6.9820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7198   -7.3945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1487   -8.2195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4342   -8.6320    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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  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  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 27  1  0  0  0  0
 25 26  1  0  0  0  0
 27 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C=C/[C@@H](O)C\C=C/C\C=C/CCCC(=O)OC(CO)CO

> <INCHI_IDENTIFIER>
InChI=1S/C23H38O5/c1-2-3-4-5-7-10-13-16-21(26)17-14-11-8-6-9-12-15-18-23(27)28-22(19-24)20-25/h6-7,9-11,13-14,16,21-22,24-26H,2-5,8,12,15,17-20H2,1H3/b9-6-,10-7-,14-11-,16-13+/t21-/m1/s1

> <INCHI_KEY>
SSHLWLAPLZCWOT-XYOZOUKRSA-N

> <FORMULA>
C23H38O5

> <MOLECULAR_WEIGHT>
394.5448

> <EXACT_MASS>
394.271924326

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
45.88910785704906

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate

> <ALOGPS_LOGP>
4.62

> <JCHEM_LOGP>
4.181816846

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.979619367999383

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.278372842011322

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6087117775248538

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
118.49339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
18

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.94e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate

> <JCHEM_VEBER_RULE>
0

$$$$

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      33.880 -26.893   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.546 -27.663   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.213 -26.893   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.879 -27.663   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.545 -26.893   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.212 -27.663   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.878 -26.893   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.878 -25.353   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.544 -24.583   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.544 -23.043   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      23.211 -22.273   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      25.878 -22.273   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      27.212 -23.043   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      28.545 -22.273   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.545 -20.733   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.879 -19.963   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.879 -18.423   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      28.545 -17.653   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.545 -16.113   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.212 -15.343   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.212 -13.803   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      28.545 -13.033   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      25.878 -13.033   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      24.544 -13.803   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      23.211 -13.033   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      21.877 -13.803   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      24.544 -15.343   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      23.211 -16.113   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   12                                                  
CONECT   11   10                                                            
CONECT   12   10   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   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   27                                                  
CONECT   25   24   26                                                       
CONECT   26   25                                                            
CONECT   27   24   28                                                       
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

View in JSmol

Synonyms

Value	Source
11-Hydroxyeicosatetraenoic acid glyceryl ester	Generator
(11S)-Hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl-2-glyceryl ester	HMDB
(5Z,8Z,12E,14Z)-11S-Hydroxyeicosatetraenoyl-2-glyceryl ester	HMDB
11-HETE-g	HMDB
2-[(11S)-Hydroxy-(5Z,8Z,12E,14Z)-eicosatetraenoyl]-glycerol	HMDB
1,3-Dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoic acid	Generator

Chemical Formula

C₂₃H₃₈O₅

Average Mass

394.5448 Da

Monoisotopic Mass

394.27192 Da

IUPAC Name

1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate

Traditional Name

1,3-dihydroxypropan-2-yl (5Z,8Z,11S,12E,14Z)-11-hydroxyicosa-5,8,12,14-tetraenoate

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C=C/[C@@H](O)C\C=C/C\C=C/CCCC(=O)OC(CO)CO

InChI Identifier

InChI=1S/C23H38O5/c1-2-3-4-5-7-10-13-16-21(26)17-14-11-8-6-9-12-15-18-23(27)28-22(19-24)20-25/h6-7,9-11,13-14,16,21-22,24-26H,2-5,8,12,15,17-20H2,1H3/b9-6-,10-7-,14-11-,16-13+/t21-/m1/s1

InChI Key

SSHLWLAPLZCWOT-XYOZOUKRSA-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 endocannabinoids. These are arachidonic acid derivatives containing either an N-acetylethanolamine(type 1) or a glycerol(types 2 and 3) moiety attached to the aliphatic tail.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Endocannabinoids

Sub Class

Not Available

Direct Parent

Endocannabinoids

Alternative Parents

Substituents

2-arachidonoylglycerol-skeleton
Hydroxyeicosapolyenoic acid
Eicosanoid
Fatty alcohol
2-acyl-sn-glycerol
Monoradylglycerol
Monoacylglycerol
Glycerolipid
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

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	4.62	ALOGPS
logP	4.18	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	14.28	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	118.49 m³·mol⁻¹	ChemAxon
Polarizability	45.89 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

HMDB0012530

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029112

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

53481455

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 11-Hydroxyeicosatetraenoate glyceryl ester (NP0339030)

MOL for NP0339030 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D MOL for NP0339030 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D SDF for NP0339030 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D-SDF for NP0339030 (11-Hydroxyeicosatetraenoate glyceryl ester)

PDB for NP0339030 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D PDB for NP0339030 (11-Hydroxyeicosatetraenoate glyceryl ester)

SMILES for NP0339030 (11-Hydroxyeicosatetraenoate glyceryl ester)

INCHI for NP0339030 (11-Hydroxyeicosatetraenoate glyceryl ester)

Structure for NP0339030 (11-Hydroxyeicosatetraenoate glyceryl ester)

3D Structure for NP0339030 (11-Hydroxyeicosatetraenoate glyceryl ester)