NP-MRD: Showing NP-Card for 15S-Hydroperoxyeicosatetraenoic acid (NP0050312)

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Record Information

Version

2.0

Created at

2022-04-27 20:52:25 UTC

Updated at

2022-04-27 20:52:25 UTC

NP-MRD ID

NP0050312

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15S-Hydroperoxyeicosatetraenoic acid

Description

15(S)-HPETE, also known as 15S-hpete or 15-HPAA, belongs to the class of organic compounds known as hydroperoxyeicosatetraenoic acids. These are eicosanoic acids with an attached hydroperoxyl group and four CC double bonds. Thus, 15(S)-hpete is considered to be an eicosanoid lipid molecule. 15(S)-HPETE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 15(S)-HPETE exists in all living organisms, ranging from bacteria to humans. 15S-Hydroperoxyeicosatetraenoic acid is found in Apis cerana, Mus musculus and Saprolegnia parasitica. 15S-Hydroperoxyeicosatetraenoic acid was first documented in 1993 (PMID: 8441337). The (S)-enantiomer of 15-HPETE (PMID: 8994519) (PMID: 15964853) (PMID: 15723435) (PMID: 8655602).

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 02231219552D          

 24 23  0  0  1  0            999 V2000
   25.7958  -10.2641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5102  -10.6766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7958  -15.2142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5102  -13.9767    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.7958   -9.4391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.5102   -9.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2247   -9.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9392   -9.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0812  -13.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6537   -9.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0812  -13.9767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3668  -12.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9378  -11.9141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9378  -10.2641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3682   -9.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7958  -14.3892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6523  -13.1517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9378  -12.7391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2233  -11.5016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2233  -10.6766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0812   -9.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9378   -9.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3668   -9.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6523   -9.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  5  1  1  6  0  0  0
  3 16  1  0  0  0  0
  4 16  2  0  0  0  0
  5  6  1  0  0  0  0
  5 21  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  1  0  0  0  0
 12 17  1  0  0  0  0
 13 18  1  0  0  0  0
 13 19  1  0  0  0  0
 14 20  1  0  0  0  0
 14 22  1  0  0  0  0
 17 18  2  0  0  0  0
 19 20  2  0  0  0  0
 21 23  2  0  0  0  0
 22 24  2  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0050312

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h4-5,8-11,14,17,19,23H,2-3,6-7,12-13,15-16,18H2,1H3,(H,21,22)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1

> <INCHI_KEY>
BFWYTORDSFIVKP-VAEKSGALSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.422233971583424

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5Z,8Z,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid

> <ALOGPS_LOGP>
5.86

> <JCHEM_LOGP>
5.805695121333333

> <ALOGPS_LOGS>
-5.27

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.712374063193028

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771784961381

> <JCHEM_PKA_STRONGEST_BASIC>
-4.236807609084836

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
102.81970000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.80e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15(S)-hpete

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      48.152 -19.160   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      49.486 -19.930   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      48.152 -28.400   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      49.486 -26.090   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      48.152 -17.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      49.486 -16.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      50.819 -17.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      52.153 -16.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      46.818 -24.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      53.487 -17.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      46.818 -26.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      45.485 -23.780   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      42.817 -22.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      42.817 -19.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      54.821 -16.850   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      48.152 -26.860   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      44.151 -24.550   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      42.817 -23.780   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      41.483 -21.470   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      41.483 -19.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      46.818 -16.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      42.817 -17.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.485 -17.620   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      44.151 -16.850   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1                                                            
CONECT    3   16                                                            
CONECT    4   16                                                            
CONECT    5    1    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7   10                                                       
CONECT    9   11   12                                                       
CONECT   10    8   15                                                       
CONECT   11    9   16                                                       
CONECT   12    9   17                                                       
CONECT   13   18   19                                                       
CONECT   14   20   22                                                       
CONECT   15   10                                                            
CONECT   16    3    4   11                                                  
CONECT   17   12   18                                                       
CONECT   18   13   17                                                       
CONECT   19   13   20                                                       
CONECT   20   14   19                                                       
CONECT   21    5   23                                                       
CONECT   22   14   24                                                       
CONECT   23   21   24                                                       
CONECT   24   22   23                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

View in JSmol

Synonyms

Value	Source
(5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoate	ChEBI
(5Z,8Z,11Z,13E)-(15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid	ChEBI
15-Hydroperoxyeicosatetraenoate	ChEBI
15-Hydroperoxyeicosatetraenoic acid	ChEBI
15-Hydroperoxyicosatetraenoate	ChEBI
15-Hydroperoxyicosatetraenoic acid	ChEBI
15S-HpETE	ChEBI
(5Z,8Z,11Z,13E,15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoic acid	HMDB
(5Z,8Z,11Z,13E,15S)-15-Hydroperoxyicosa-5,8,11,13-tetraenoate	HMDB
15S-Hydroperoxyeicosatetraenoate	HMDB
15S-Hydroperoxyeicosatetraenoic acid	HMDB
14,15-Epoxyarachidonic acid	HMDB
15-HPEA	HMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (Z,Z,Z,Z)-isomer	HMDB
15-Hydroperoxyarachidonic acid	HMDB
15-HPAA	HMDB
15-HPETE	HMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid	HMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (e,Z,Z,Z)-isomer	HMDB
15-Hydroperoxy-5,8,11,13-eicosatetraenoic acid, (S)-(e,Z,Z,Z)-isomer	HMDB
15-Hydroperoxy-5,8,11,14-eicosatetraenoic acid	HMDB
Arachidonic acid 15-hydroperoxide	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4657 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

(5Z,8Z,11Z,13E,15S)-15-hydroperoxyicosa-5,8,11,13-tetraenoic acid

Traditional Name

15(S)-hpete

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h4-5,8-11,14,17,19,23H,2-3,6-7,12-13,15-16,18H2,1H3,(H,21,22)/b5-4-,10-8-,11-9-,17-14+/t19-/m0/s1

InChI Key

BFWYTORDSFIVKP-VAEKSGALSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Apis cerana	LOTUS Database	35616633
Mus musculus	LOTUS Database	35616633
Saprolegnia parasitica	Chromalveolata	KNApSAcK

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroperoxyeicosatetraenoic acids

Alternative Parents

Substituents

Hydroperoxyeicosatetraenoic acid
Long-chain fatty acid
Hydroperoxy fatty acid
Fatty acid
Unsaturated fatty acid
Allylic hydroperoxide
Hydroperoxide
Carboxylic acid derivative
Alkyl hydroperoxide
Carboxylic acid
Peroxol
Monocarboxylic acid or derivatives
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

HPETE (CHEBI:15628 )
Hydroperoxy fatty acids (C05966 )
Hydroxy/hydroperoxyeicosatetraenoic acids (C05966 )
Hydroxy/hydroperoxyeicosatetraenoic acids (LMFA03060014 )

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	5.86	ALOGPS
logP	5.81	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	4.82	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	15	ChemAxon
Refractivity	102.82 m³·mol⁻¹	ChemAxon
Polarizability	38.42 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

External Links

HMDB ID

HMDB0004244

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

47085

Wikipedia Link

Not Available

METLIN ID

7039

PubChem Compound

5280893

PDB ID

Not Available

ChEBI ID

15628

Good Scents ID

Not Available

References

General References

Kuitert LM, Newton R, Barnes NC, Adcock IM, Barnes PJ: Eicosanoid mediator expression in mononuclear and polymorphonuclear cells in normal subjects and patients with atopic asthma and cystic fibrosis. Thorax. 1996 Dec;51(12):1223-8. doi: 10.1136/thx.51.12.1223. [PubMed:8994519 ]
Terao J, Nagao A, Yuki H, Itoh Y: Reduction of fatty acid hydroperoxides by human parotid saliva. Lipids. 1993 Feb;28(2):121-4. doi: 10.1007/BF02535775. [PubMed:8441337 ]
Lee SH, Williams MV, Dubois RN, Blair IA: Cyclooxygenase-2-mediated DNA damage. J Biol Chem. 2005 Aug 5;280(31):28337-46. doi: 10.1074/jbc.M504178200. Epub 2005 Jun 17. [PubMed:15964853 ]
Williams MV, Lee SH, Blair IA: Liquid chromatography/mass spectrometry analysis of bifunctional electrophiles and DNA adducts from vitamin C mediated decomposition of 15-hydroperoxyeicosatetraenoic acid. Rapid Commun Mass Spectrom. 2005;19(6):849-58. doi: 10.1002/rcm.1854. [PubMed:15723435 ]
Sultana C, Shen Y, Rattan V, Kalra VK: Lipoxygenase metabolites induced expression of adhesion molecules and transendothelial migration of monocyte-like HL-60 cells is linked to protein kinase C activation. J Cell Physiol. 1996 Jun;167(3):477-87. doi: 10.1002/(SICI)1097-4652(199606)167:3<477::AID-JCP12>3.0.CO;2-1. [PubMed:8655602 ]

Showing NP-Card for 15S-Hydroperoxyeicosatetraenoic acid (NP0050312)

MOL for NP0050312 (15S-Hydroperoxyeicosatetraenoic acid)

3D MOL for NP0050312 (15S-Hydroperoxyeicosatetraenoic acid)

3D SDF for NP0050312 (15S-Hydroperoxyeicosatetraenoic acid)

3D-SDF for NP0050312 (15S-Hydroperoxyeicosatetraenoic acid)

PDB for NP0050312 (15S-Hydroperoxyeicosatetraenoic acid)

3D PDB for NP0050312 (15S-Hydroperoxyeicosatetraenoic acid)

SMILES for NP0050312 (15S-Hydroperoxyeicosatetraenoic acid)

INCHI for NP0050312 (15S-Hydroperoxyeicosatetraenoic acid)

Structure for NP0050312 (15S-Hydroperoxyeicosatetraenoic acid)

3D Structure for NP0050312 (15S-Hydroperoxyeicosatetraenoic acid)