NP-MRD: Showing NP-Card for (5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid (NP0217844)

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Record Information

Version

2.0

Created at

2022-09-05 18:19:15 UTC

Updated at

2022-09-05 18:19:15 UTC

NP-MRD ID

NP0217844

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid

Description

(5S,8E,10E,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated. (5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid is found in Mus musculus. Based on a literature review very few articles have been published on (5S,8E,10E,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052220192D          

 25 24  0  0  1  0            999 V2000
   -3.2408   11.3289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2408   10.5039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9552   10.0914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263   10.0914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5263    9.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    8.8539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8118    8.0289    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5263    7.6164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    7.6164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0974    6.7914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    6.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829    5.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    5.1414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3316    4.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.9039    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7605    4.3164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0461    3.0789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0474    1.8414    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  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  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  4  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  6  0  0  0
 15 17  1  0  0  0  0
 18 17  1  4  0  0  0
 18 19  2  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
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0217844

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3?,13-8+,14-9?/t18-,19-/m1/s1

> <INCHI_KEY>
PTJFJXLGRSTECQ-OGITZFQVSA-N

> <FORMULA>
C20H32O5

> <MOLECULAR_WEIGHT>
352.471

> <EXACT_MASS>
352.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
42.47878656744826

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,8E,10E,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid

> <JCHEM_LOGP>
2.688870060333332

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.843936486031904

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.646345072403522

> <JCHEM_PKA_STRONGEST_BASIC>
-1.1987619626600479

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
104.91369999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(5S,8E,10E,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  O   UNK     0      -6.049  21.147   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.049  19.607   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -7.383  18.837   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -4.716  18.837   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.716  17.297   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.382  16.527   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.382  14.987   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.716  14.217   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.048  14.217   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.048  12.677   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.715  11.907   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.715  10.367   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.619   9.597   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.619   8.057   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.953   7.287   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.286   8.057   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.953   5.747   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.286   4.977   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.286   3.437   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.954   3.437   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.287   2.667   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.621   3.437   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.955   2.667   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      11.288   3.437   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   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   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

View in JSmol

Synonyms

Value	Source
(5S,8E,10E,12R)-5,12,20-Trihydroxyicosa-6,8,10,14-tetraenoate	Generator

Chemical Formula

C₂₀H₃₂O₅

Average Mass

352.4710 Da

Monoisotopic Mass

352.22497 Da

IUPAC Name

(5S,8E,10E,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid

Traditional Name

(5S,8E,10E,12R)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3?,13-8+,14-9?/t18-,19-/m1/s1

InChI Key

PTJFJXLGRSTECQ-OGITZFQVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mus musculus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as leukotrienes. These are eicosanoids containing a hydroxyl group attached to the aliphatic chain of an arachidonic acid. Leukotrienes have four double bonds, three (and only three) of which are conjugated.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Leukotrienes

Alternative Parents

Substituents

Leukotriene
Hydroxyeicosatetraenoic acid
Long-chain fatty acid
Hydroxy fatty acid
Fatty acid
Unsaturated fatty acid
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	2.69	ChemAxon
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	97.99 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	104.91 m³·mol⁻¹	ChemAxon
Polarizability	42.48 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

163060613

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid (NP0217844)

MOL for NP0217844 ((5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid)

3D MOL for NP0217844 ((5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid)

3D SDF for NP0217844 ((5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid)

3D-SDF for NP0217844 ((5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid)

PDB for NP0217844 ((5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid)

3D PDB for NP0217844 ((5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid)

SMILES for NP0217844 ((5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid)

INCHI for NP0217844 ((5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid)

Structure for NP0217844 ((5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid)

3D Structure for NP0217844 ((5s,8e,10e,12r)-5,12,20-trihydroxyicosa-6,8,10,14-tetraenoic acid)