Np mrd loader

Showing NP-Card for 17-HETE (NP0339059)

Jump To Section:
IdentificationSpectraBioTaxonomyChemoTaxonomyPhysical propertiesLinksReferencesXML
Record Information
Version2.0
Created at2024-09-11 19:29:35 UTC
Updated at2024-09-11 19:29:35 UTC
NP-MRD IDNP0339059
Secondary Accession NumbersNone
Natural Product Identification
Common Name17-HETE
Description 17-HETE was first documented in 2014 (PMID: 25065748). Based on a literature review a significant number of articles have been published on 17-HETE (PMID: 37244564) (PMID: 34904633) (PMID: 34591339) (PMID: 34158817) (PMID: 32900329) (PMID: 30543782).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0339059 (17-HETE)


  Mrv2104 05262322012D          

 23 22  0  0  0  0            999 V2000
    9.6812  -15.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0937  -14.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9188  -14.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3313  -14.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1563  -14.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9188  -13.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0937  -13.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6812  -12.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0937  -11.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6812  -11.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0937  -10.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9188  -10.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3313   -9.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1563   -9.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5688  -10.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3938  -10.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8063  -11.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3938  -11.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8063  -12.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3938  -13.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8063  -14.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3938  -14.7945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6313  -14.0800    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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 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  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
Download

3D MOL for NP0339059 (17-HETE)

Download
3D SDF for NP0339059 (17-HETE)

  Mrv2104 05262322012D          

 23 22  0  0  0  0            999 V2000
    9.6812  -15.5090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0937  -14.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9188  -14.7945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3313  -14.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1563  -14.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9188  -13.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0937  -13.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6812  -12.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0937  -11.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6812  -11.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0937  -10.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9188  -10.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3313   -9.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1563   -9.7931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5688  -10.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3938  -10.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8063  -11.2221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3938  -11.9366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8063  -12.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3938  -13.3656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8063  -14.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3938  -14.7945    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6313  -14.0800    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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 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  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339059

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(O)C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C20H32O3/c1-2-16-19(21)17-14-12-10-8-6-4-3-5-7-9-11-13-15-18-20(22)23/h3,5-6,8-9,11-12,14,19,21H,2,4,7,10,13,15-18H2,1H3,(H,22,23)/b5-3-,8-6-,11-9-,14-12-

> <INCHI_KEY>
OPPIPPRXLIDJKN-JPURVOHMNA-N

> <FORMULA>
C20H32O3

> <MOLECULAR_WEIGHT>
320.473

> <EXACT_MASS>
320.23514489

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
38.00484816971378

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z)-17-hydroxyicosa-5,8,11,14-tetraenoic acid

> <JCHEM_LOGP>
5.200452284

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
18.444729922540997

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.8197721762113055

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2920754675696142

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
101.62349999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
17-hete

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339059 (17-HETE)
Download
PDB for NP0339059 (17-HETE)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      18.072 -28.950   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.842 -27.616   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.382 -27.616   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      21.152 -26.283   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      22.692 -26.283   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      20.382 -24.949   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      18.842 -24.949   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.072 -23.615   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.842 -22.282   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.072 -20.948   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.842 -19.614   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.382 -19.614   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.152 -18.280   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.692 -18.280   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.462 -19.614   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.002 -19.614   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.772 -20.948   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      25.002 -22.282   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      25.772 -23.615   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      25.002 -24.949   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.772 -26.283   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      25.002 -27.616   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      27.312 -26.283   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    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   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

Download
3D PDB for NP0339059 (17-HETE)
Download
SMILES for NP0339059 (17-HETE)
CCCC(O)C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
Download
INCHI for NP0339059 (17-HETE)
InChI=1/C20H32O3/c1-2-16-19(21)17-14-12-10-8-6-4-3-5-7-9-11-13-15-18-20(22)23/h3,5-6,8-9,11-12,14,19,21H,2,4,7,10,13,15-18H2,1H3,(H,22,23)/b5-3-,8-6-,11-9-,14-12-
Download
View in JSmol
SynonymsNot Available
Chemical FormulaC20H32O3
Average Mass320.4730 Da
Monoisotopic Mass320.23514 Da
IUPAC Name(5Z,8Z,11Z,14Z)-17-hydroxyicosa-5,8,11,14-tetraenoic acid
Traditional Name17-hete
CAS Registry NumberNot Available
SMILES
CCCC(O)C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1/C20H32O3/c1-2-16-19(21)17-14-12-10-8-6-4-3-5-7-9-11-13-15-18-20(22)23/h3,5-6,8-9,11-12,14,19,21H,2,4,7,10,13,15-18H2,1H3,(H,22,23)/b5-3-,8-6-,11-9-,14-12-
InChI KeyOPPIPPRXLIDJKN-JPURVOHMNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP5.2ChemAxon
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count14ChemAxon
Refractivity101.62 m³·mol⁻¹ChemAxon
Polarizability38 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Isse FA, Alammari AH, El-Sherbeni AA, El-Kadi AOS: 17-(R/S)-hydroxyeicosatetraenoic acid (HETE) induces cardiac hypertrophy through the CYP1B1 in enantioselective manners. Prostaglandins Other Lipid Mediat. 2023 Oct;168:106749. doi:  10.1016/j.prostaglandins.2023.106749. Epub 2023 May 25. [PubMed:37244564  ] 
  2. Gong Y, Ni X, Jin C, Li X, Wang Y, Wang O, Li M, Xing X, Wu Z, Jiang Y, Xia W: Serum Metabolomics Reveals Dysregulation and Diagnostic Potential of Oxylipins in Tumor-induced Osteomalacia. J Clin Endocrinol Metab. 2022 Apr 19;107(5):1383-1391. doi:  10.1210/clinem/dgab885. [PubMed:34904633  ] 
  3. Nagata N, Hamasaki Y, Inagaki S, Nakamura T, Horikami D, Yamamoto-Hanada K, Inuzuka Y, Shimosawa T, Kobayashi K, Narita M, Ohya Y, Murata T: Urinary lipid profile of atopic dermatitis in murine model and human patients. FASEB J. 2021 Nov;35(11):e21949. doi: 10.1096/fj.202100828R. [PubMed:34591339  ] 
  4. Zhu Z, Zhou W, Yang Y, Wang K, Li F, Dang Y: Quantitative Profiling of Oxylipin Reveals the Mechanism of Pien-Tze-Huang on Alcoholic Liver Disease. Evid Based Complement Alternat Med. 2021 Jun 1;2021:9931542. doi:  10.1155/2021/9931542. eCollection 2021. [PubMed:34158817  ] 
  5. Cioccari L, Luethi N, Duong T, Ryan E, Cutuli SL, Lloyd-Donald P, Eastwood GM, Peck L, Young H, Vaara ST, French CJ, Orford N, Dwivedi J, Lankadeva YR, Bailey M, Reid GE, Bellomo R: Cytokine and lipid metabolome effects of low-dose acetylsalicylic acid in critically ill patients with systemic inflammation: a pilot, feasibility, multicentre, randomised, placebo-controlled trial. Crit Care Resusc. 2020 Sep;22(3):227-236. doi: 10.1016/S1441-2772(23)00390-3. [PubMed:32900329  ] 
  6. Shoieb SM, El-Sherbeni AA, El-Kadi AOS: Subterminal hydroxyeicosatetraenoic acids: Crucial lipid mediators in normal physiology and disease states. Chem Biol Interact. 2019 Feb 1;299:140-150. doi: 10.1016/j.cbi.2018.12.004. Epub  2018 Dec 10. [PubMed:30543782  ] 
  7. Anwar-Mohamed A, Elshenawy OH, El-Sherbeni AA, Abdelrady M, El-Kadi AO: Acute arsenic treatment alters arachidonic acid and its associated metabolite levels in the brain of C57Bl/6 mice. Can J Physiol Pharmacol. 2014 Aug;92(8):693-702. doi: 10.1139/cjpp-2014-0136. [PubMed:25065748  ]