NP-MRD: Showing NP-Card for 18R-HEPE (NP0339067)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 19:32:00 UTC

Updated at

2024-09-11 19:32:00 UTC

NP-MRD ID

NP0339067

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18R-HEPE

Description

18R-HEPE, also known as 18-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, 18R-hepe is considered to be an eicosanoid lipid molecule. 18R-HEPE is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208082D          

 23 22  0  0  1  0            999 V2000
   14.8911   -8.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7161   -8.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1286   -8.8654    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.9537   -8.8654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7161   -9.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8911   -9.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4786  -10.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6536  -10.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2411   -9.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4161   -9.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0036   -8.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1786   -8.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7661   -8.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9411   -8.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5286   -8.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7036   -8.8654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2911   -9.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7036  -10.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2911  -11.0088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7036  -11.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2911  -12.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4661  -12.4378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7036  -13.1523    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  6  0  0  0
  3  5  1  0  0  0  0
  5  6  2  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>
NP0339067

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,15,17,19,21H,2-3,8-9,14,16,18H2,1H3,(H,22,23)/b6-4-,7-5+,12-10-,13-11-,17-15+/t19-/m0/s1

> <INCHI_KEY>
LRWYBGFSVUBWMO-NQZHIPPKSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
37.124348221015715

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11E,14Z,16E,18S)-18-hydroxyicosa-5,8,11,14,16-pentaenoic acid

> <ALOGPS_LOGP>
5.60

> <JCHEM_LOGP>
4.994438087333332

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.606923431588807

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.819771984893506

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6585318353943026

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
102.5861

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.48e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8Z,11E,14Z,16E,18S)-18-hydroxyicosa-5,8,11,14,16-pentaenoic acid

> <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      27.797 -15.215   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      29.337 -15.215   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      30.107 -16.549   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      31.647 -16.549   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      29.337 -17.882   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.797 -17.882   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      27.027 -19.216   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      25.487 -19.216   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.717 -17.882   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.177 -17.882   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.407 -16.549   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      20.867 -16.549   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      20.097 -15.215   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.557 -15.215   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.787 -16.549   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      16.247 -16.549   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.477 -17.882   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      16.247 -19.216   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.477 -20.550   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.247 -21.883   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.477 -23.217   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      13.937 -23.217   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      16.247 -24.551   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    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

View in JSmol

Synonyms

Value	Source
18(R)-Hydroxyeicosa-5Z,8Z,11E,14Z,16E-pentaenoate	HMDB
18(R)-Hydroxyeicosa-5Z,8Z,11E,14Z,16E-pentaenoic acid	HMDB
18-HEPE	HMDB

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4504 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

(5Z,8Z,11E,14Z,16E,18S)-18-hydroxyicosa-5,8,11,14,16-pentaenoic acid

Traditional Name

(5Z,8Z,11E,14Z,16E,18S)-18-hydroxyicosa-5,8,11,14,16-pentaenoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O3/c1-2-19(21)17-15-13-11-9-7-5-3-4-6-8-10-12-14-16-18-20(22)23/h4-7,10-13,15,17,19,21H,2-3,8-9,14,16,18H2,1H3,(H,22,23)/b6-4-,7-5+,12-10-,13-11-,17-15+/t19-/m0/s1

InChI Key

LRWYBGFSVUBWMO-NQZHIPPKSA-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 hydroxyeicosapentaenoic acids. These are eicosanoic acids with an attached hydroxyl group and five CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosapentaenoic 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 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	5.6	ALOGPS
logP	4.99	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.82	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	102.59 m³·mol⁻¹	ChemAxon
Polarizability	37.12 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

HMDB0012611

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029149

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

53481496

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 18R-HEPE (NP0339067)

MOL for NP0339067 (18R-HEPE)

3D MOL for NP0339067 (18R-HEPE)

3D SDF for NP0339067 (18R-HEPE)

3D-SDF for NP0339067 (18R-HEPE)

PDB for NP0339067 (18R-HEPE)

3D PDB for NP0339067 (18R-HEPE)

SMILES for NP0339067 (18R-HEPE)

INCHI for NP0339067 (18R-HEPE)

Structure for NP0339067 (18R-HEPE)

3D Structure for NP0339067 (18R-HEPE)