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Showing NP-Card for 11R-HEPE (NP0339032)

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Record Information
Version2.0
Created at2024-09-11 19:21:24 UTC
Updated at2024-09-11 19:21:25 UTC
NP-MRD IDNP0339032
Secondary Accession NumbersNone
Natural Product Identification
Common Name11R-HEPE
Description11R-HEPE belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds. Thus, 11R-hepe is considered to be an eicosanoid lipid molecule. 11R-HEPE was first documented in 2006 (PMID: 16386769). 11R-HEPE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339032 (11R-HEPE)


  Mrv0541 02251208062D          

 23 22  0  0  1  0            999 V2000
    8.3094  -10.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3094  -11.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5950  -11.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5950  -12.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3094  -12.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3094  -13.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0239  -14.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7384  -13.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4529  -14.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1674  -13.7499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1674  -12.9249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8818  -14.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8818  -14.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5963  -15.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3108  -14.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0252  -15.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7398  -14.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7398  -14.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4542  -13.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4542  -12.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1687  -12.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8832  -12.9249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1687  -11.6874    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  2  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  6  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  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
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3D MOL for NP0339032 (11R-HEPE)

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3D SDF for NP0339032 (11R-HEPE)

  Mrv0541 02251208062D          

 23 22  0  0  1  0            999 V2000
    8.3094  -10.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3094  -11.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5950  -11.6874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5950  -12.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3094  -12.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3094  -13.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0239  -14.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7384  -13.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4529  -14.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1674  -13.7499    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.1674  -12.9249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8818  -14.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8818  -14.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5963  -15.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3108  -14.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0252  -15.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7398  -14.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7398  -14.1624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4542  -13.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4542  -12.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1687  -12.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8832  -12.9249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1687  -11.6874    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  2  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  6  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  1  0  0  0  0
 21 23  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339032

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h3-4,6-7,9-11,13-14,16,19,21H,2,5,8,12,15,17-18H2,1H3,(H,22,23)/b4-3-,9-6-,10-7-,14-11-,16-13+/t19-/m0/s1

> <INCHI_KEY>
IDEHSDHMEMMYIR-DJWFCICMSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.57167495434685

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11R,12E,14Z,17Z)-11-hydroxyicosa-5,8,12,14,17-pentaenoic acid

> <ALOGPS_LOGP>
5.53

> <JCHEM_LOGP>
4.994438087333332

> <ALOGPS_LOGS>
-5.00

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.720819929173768

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819772002441711

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6087135248988464

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
102.5861

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.22e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11R-hepe

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339032 (11R-HEPE)
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PDB for NP0339032 (11R-HEPE)
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      15.511 -19.506   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.511 -21.046   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.177 -21.816   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.177 -23.356   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.511 -24.126   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.511 -25.666   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.845 -26.436   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.178 -25.666   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      19.512 -26.436   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.846 -25.666   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      20.846 -24.126   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      22.179 -26.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.179 -27.976   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.513 -28.746   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      24.847 -27.976   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      26.180 -28.746   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      27.514 -27.976   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.514 -26.436   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.848 -25.666   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.848 -24.126   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      30.182 -23.356   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      31.515 -24.126   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      30.182 -21.816   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                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

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3D PDB for NP0339032 (11R-HEPE)
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SMILES for NP0339032 (11R-HEPE)
CC\C=C/C\C=C/C=C/[C@H](O)C\C=C/C\C=C/CCCC(O)=O
Download
INCHI for NP0339032 (11R-HEPE)
InChI=1S/C20H30O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h3-4,6-7,9-11,13-14,16,19,21H,2,5,8,12,15,17-18H2,1H3,(H,22,23)/b4-3-,9-6-,10-7-,14-11-,16-13+/t19-/m0/s1
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View in JSmol
Synonyms
ValueSource
(11R)-Hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoic acidChEBI
(11R)-Hydroxy-(5Z,8Z,12E,14Z,17Z)-icosapentaenoic acidChEBI
(5Z,8Z,11R,12E,14Z,17Z)-11-Hydroxyicosapentaenoic acidChEBI
11R-Hydroxy-5Z,8Z,12E,14Z,17Z-eicosapentaenoic acidChEBI
(11R)-Hydroxy-(5Z,8Z,12E,14Z,17Z)-eicosapentaenoateGenerator
(11R)-Hydroxy-(5Z,8Z,12E,14Z,17Z)-icosapentaenoateGenerator
(5Z,8Z,11R,12E,14Z,17Z)-11-HydroxyicosapentaenoateGenerator
11R-Hydroxy-5Z,8Z,12E,14Z,17Z-eicosapentaenoateGenerator
11(R)-Hydroxyeicosa-5Z,8Z,12E,14Z,17Z-pentaenoateHMDB
11(R)-Hydroxyeicosa-5Z,8Z,12E,14Z,17Z-pentaenoic acidHMDB
Chemical FormulaC20H30O3
Average Mass318.4504 Da
Monoisotopic Mass318.21949 Da
IUPAC Name(5Z,8Z,11R,12E,14Z,17Z)-11-hydroxyicosa-5,8,12,14,17-pentaenoic acid
Traditional Name11R-hepe
CAS Registry NumberNot Available
SMILES
CC\C=C/C\C=C/C=C/[C@H](O)C\C=C/C\C=C/CCCC(O)=O
InChI Identifier
InChI=1S/C20H30O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(22)23/h3-4,6-7,9-11,13-14,16,19,21H,2,5,8,12,15,17-18H2,1H3,(H,22,23)/b4-3-,9-6-,10-7-,14-11-,16-13+/t19-/m0/s1
InChI KeyIDEHSDHMEMMYIR-DJWFCICMSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassEicosanoids  
Direct ParentHydroxyeicosapentaenoic acids  
Alternative Parents
Substituents
  • Hydroxyeicosapentaenoic acid
    • 

  • Long-chain fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organooxygen compound
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
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
logP5.53ALOGPS
logP4.99ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.82ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity102.59 m³·mol⁻¹ChemAxon
Polarizability37.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012534  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029114  
KNApSAcK IDNot Available
Chemspider ID4446310  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5283188  
PDB IDNot Available
ChEBI ID91264  
Good Scents IDNot Available
References
General References
  1. d'Ippolito G, Cutignano A, Tucci S, Romano G, Cimino G, Fontana A: Biosynthetic intermediates and stereochemical aspects of aldehyde biosynthesis in the marine diatom Thalassiosira rotula. Phytochemistry. 2006 Feb;67(3):314-22. doi: 10.1016/j.phytochem.2005.11.012. Epub  2006 Jan 4. [PubMed:16386769  ]