NP-MRD: Showing NP-Card for 8R-HPETE (NP0050331)

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Record Information

Version

2.0

Created at

2022-04-27 20:53:14 UTC

Updated at

2022-04-27 20:53:14 UTC

NP-MRD ID

NP0050331

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8R-HPETE

Description

(5Z,8R,9E,11Z,14Z,17Z)-8-hydroperoxyicosapentaenoic acid, also known as (8R)-hydroperoxy-(5Z,9E,11Z,14Z,17Z)-eicosapentaenoic acid or (8R)-hpepe, belongs to the class of organic compounds known as hydroperoxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and five CC double bonds. 8R-HPETE is found in Agardhiella subulata. Based on a literature review very few articles have been published on (5Z,8R,9E,11Z,14Z,17Z)-8-hydroperoxyicosapentaenoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304272222532D          

 24 23  0  0  1  0            999 V2000
   -0.9059    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9059    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6204    2.3645    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6204    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7638    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4783    4.8395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    4.4270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    3.6020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072    3.1895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9072    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    1.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1927    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3349    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    2.3645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  1 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  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  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 23  1  1  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050331

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC\C=C/C\C=C/C\C=C/C=C/[C@@H](C\C=C/CCCC(O)=O)OO

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O4/c1-2-3-4-5-6-7-8-9-10-13-16-19(24-23)17-14-11-12-15-18-20(21)22/h3-4,6-7,9-11,13-14,16,19,23H,2,5,8,12,15,17-18H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,14-11-,16-13+/t19-/m0/s1

> <INCHI_KEY>
FKUQDPQMNVKDHV-CLXNAOOQSA-N

> <FORMULA>
C20H30O4

> <MOLECULAR_WEIGHT>
334.456

> <EXACT_MASS>
334.214409446

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.59423194737903

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8R,9E,11Z,14Z,17Z)-8-hydroperoxyicosa-5,9,11,14,17-pentaenoic acid

> <ALOGPS_LOGP>
5.56

> <JCHEM_LOGP>
5.443773464666666

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.71107422095279

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.390349853072395

> <JCHEM_PKA_STRONGEST_BASIC>
-4.237376144832223

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
103.93630000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8R,9E,11Z,14Z,17Z)-8-hydroperoxyicosa-5,9,11,14,17-pentaenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-22         0                                  
HETATM    1  C   UNK     0      -1.691   3.644   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.691   2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.025   4.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.025   5.954   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.358   6.724   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.358   8.264   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.692   9.034   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -7.026   8.264   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.359   9.034   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -9.693   8.264   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -9.693   6.724   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -11.027   5.954   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -11.027   4.414   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -9.693   3.644   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -9.693   2.104   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.358   3.644   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.692   4.414   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    1   11   23                                                  
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                                                            
CONECT   23   10   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

View in JSmol

Synonyms

Value	Source
(8R)-HPEPE	ChEBI
(8R)-Hydroperoxy-(5Z,9E,11Z,14Z,17Z)-eicosapentaenoic acid	ChEBI
(8R)-Hydroperoxy-(5Z,9E,11Z,14Z,17Z)-icosapentaenoic acid	ChEBI
(8R)-Hydroperoxy-(5Z,9E,11Z,14Z,17Z)-eicosapentaenoate	Generator
(8R)-Hydroperoxy-(5Z,9E,11Z,14Z,17Z)-icosapentaenoate	Generator
(5Z,8R,9E,11Z,14Z,17Z)-8-Hydroperoxyicosapentaenoate	Generator

Chemical Formula

C₂₀H₃₀O₄

Average Mass

334.4560 Da

Monoisotopic Mass

334.21441 Da

IUPAC Name

(5Z,8R,9E,11Z,14Z,17Z)-8-hydroperoxyicosa-5,9,11,14,17-pentaenoic acid

Traditional Name

(5Z,8R,9E,11Z,14Z,17Z)-8-hydroperoxyicosa-5,9,11,14,17-pentaenoic acid

CAS Registry Number

Not Available

SMILES

CC\C=C/C\C=C/C\C=C/C=C/[C@@H](C\C=C/CCCC(O)=O)OO

InChI Identifier

InChI=1S/C20H30O4/c1-2-3-4-5-6-7-8-9-10-13-16-19(24-23)17-14-11-12-15-18-20(21)22/h3-4,6-7,9-11,13-14,16,19,23H,2,5,8,12,15,17-18H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,14-11-,16-13+/t19-/m0/s1

InChI Key

FKUQDPQMNVKDHV-CLXNAOOQSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agardhiella subulata	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroperoxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and five CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroperoxyeicosapentaenoic acids

Alternative Parents

Substituents

Hydroperoxyeicosapentaenoic acid
Long-chain fatty acid
Hydroperoxy fatty acid
Fatty acid
Unsaturated fatty acid
Allylic hydroperoxide
Hydroperoxide
Alkyl hydroperoxide
Peroxol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.56	ALOGPS
logP	5.44	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.39	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	103.94 m³·mol⁻¹	ChemAxon
Polarizability	38.59 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58827627

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

123132032

PDB ID

Not Available

ChEBI ID

136662

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 8R-HPETE (NP0050331)

MOL for NP0050331 (8R-HPETE)

3D MOL for NP0050331 (8R-HPETE)

3D SDF for NP0050331 (8R-HPETE)

3D-SDF for NP0050331 (8R-HPETE)

PDB for NP0050331 (8R-HPETE)

3D PDB for NP0050331 (8R-HPETE)

SMILES for NP0050331 (8R-HPETE)

INCHI for NP0050331 (8R-HPETE)

Structure for NP0050331 (8R-HPETE)

3D Structure for NP0050331 (8R-HPETE)