NP-MRD: Showing NP-Card for 10,11-Dihydro-12R-hydroxy-leukotriene E4 (NP0339021)

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Record Information

Version

2.0

Created at

2024-09-11 19:17:25 UTC

Updated at

2024-09-11 19:17:26 UTC

NP-MRD ID

NP0339021

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10,11-Dihydro-12R-hydroxy-leukotriene E4

Description

10,11-Dihydro-12R-hydroxy-leukotriene E4, also known as e-LTB(,3) or ELTB3, belongs to the class of organic compounds known as hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds. Thus, 10,11-dihydro-12R-hydroxy-leukotriene E4 is considered to be an eicosanoid lipid molecule. The PGs and TXs are collectively identified as prostanoids. 10,11-Dihydro-12R-hydroxy-leukotriene E4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. LTE4, activate contractile and inflammatory processes via specific interaction with putative seven transmembrane-spanning receptors that couple to G proteins and subsequent intracellular signaling pathways. All mammalian cells except erythrocytes synthesize eicosanoids. Leukotrienes are eicosanoids.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208062D          

 31 30  0  0  1  0            999 V2000
   14.7462   -8.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4606   -8.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4606   -9.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1751   -9.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1751  -10.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8896  -11.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8896  -11.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1751  -12.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1751  -13.1662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.8896  -13.5788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4606  -13.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7462  -13.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0317  -13.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3172  -13.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6027  -13.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8882  -13.1663    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1738  -13.5788    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4593  -13.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7448  -13.5788    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7448  -14.4038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0304  -13.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0304  -12.3413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3159  -13.5788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8882  -12.3413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1738  -11.9287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6027  -11.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3172  -12.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0317  -11.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0317  -11.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3172  -10.6912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7462  -10.6912    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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 24  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END


  Mrv0541 02251208062D          

 31 30  0  0  1  0            999 V2000
   14.7462   -8.2162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4606   -8.6287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4606   -9.4537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1751   -9.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1751  -10.6912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8896  -11.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8896  -11.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1751  -12.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1751  -13.1662    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.8896  -13.5788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4606  -13.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7462  -13.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0317  -13.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3172  -13.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6027  -13.5788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8882  -13.1663    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1738  -13.5788    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4593  -13.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7448  -13.5788    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7448  -14.4038    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0304  -13.1663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0304  -12.3413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3159  -13.5788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8882  -12.3413    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.1738  -11.9287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6027  -11.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3172  -12.3413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0317  -11.9287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0317  -11.1037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3172  -10.6912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7462  -10.6912    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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 24  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339021

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H39NO6S/c1-2-3-4-5-6-8-12-18(25)13-9-7-10-15-21(31-17-19(24)23(29)30)20(26)14-11-16-22(27)28/h6-10,15,18-21,25-26H,2-5,11-14,16-17,24H2,1H3,(H,27,28)(H,29,30)/b8-6-,9-7+,15-10+/t18-,19+,20-,21+/m0/s1

> <INCHI_KEY>
FZJOTYMARNGISF-YXSOTRFDSA-N

> <FORMULA>
C23H39NO6S

> <MOLECULAR_WEIGHT>
457.624

> <EXACT_MASS>
457.249808675

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
53.02040065202767

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6R,7E,9E,12S,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5,12-dihydroxyicosa-7,9,14-trienoic acid

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
1.0019314286017582

> <ALOGPS_LOGS>
-4.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
4.455705839673921

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.345420424367948

> <JCHEM_PKA_STRONGEST_BASIC>
9.130042322044691

> <JCHEM_POLAR_SURFACE_AREA>
141.08

> <JCHEM_REFRACTIVITY>
128.1726

> <JCHEM_ROTATABLE_BOND_COUNT>
19

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.28e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6R,7E,9E,12S,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5,12-dihydroxyicosa-7,9,14-trienoic 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      27.526 -15.337   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.860 -16.107   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.860 -17.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.194 -18.417   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      30.194 -19.957   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      31.527 -20.727   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      31.527 -22.267   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      30.194 -23.037   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.194 -24.577   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      31.527 -25.347   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      28.860 -25.347   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.526 -24.577   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.193 -25.347   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.859 -24.577   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.525 -25.347   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      22.191 -24.577   0.000  0.00  0.00           C+0
HETATM   17  S   UNK     0      20.858 -25.347   0.000  0.00  0.00           S+0
HETATM   18  C   UNK     0      19.524 -24.577   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      18.190 -25.347   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0      18.190 -26.887   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      16.857 -24.577   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      16.857 -23.037   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      15.523 -25.347   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      22.191 -23.037   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      20.858 -22.267   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      23.525 -22.267   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      24.859 -23.037   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.193 -22.267   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      26.193 -20.727   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      24.859 -19.957   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      27.526 -19.957   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   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   24                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   16   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   60    0
END

View in JSmol

Synonyms

Value	Source
(5S,6R,12R)-Dihydroxy-6-(S-cysteinyl)-(7E,9E,14Z)-eicosatrienoate	HMDB
(5S,6R,12R)-Dihydroxy-6-(S-cysteinyl)-(7E,9E,14Z)-eicosatrienoic acid	HMDB
5,12-Dihydroxy-6-cysteinyl-7,9,14-eicosatrienoate	HMDB
5,12-Dihydroxy-6-cysteinyl-7,9,14-eicosatrienoic acid	HMDB
5S,12R-Dihydroxy-6-S-cysteinyl-7E,9E,14Z-eicosatrienoate	HMDB
5S,12R-Dihydroxy-6-S-cysteinyl-7E,9E,14Z-eicosatrienoic acid	HMDB
e-LTB(,3)	HMDB
ELTB3	HMDB
epsilon-LTB(,3)	HMDB

Chemical Formula

C₂₃H₃₉NO₆S

Average Mass

457.6240 Da

Monoisotopic Mass

457.24981 Da

IUPAC Name

(5S,6R,7E,9E,12S,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5,12-dihydroxyicosa-7,9,14-trienoic acid

Traditional Name

(5S,6R,7E,9E,12S,14Z)-6-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-5,12-dihydroxyicosa-7,9,14-trienoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C23H39NO6S/c1-2-3-4-5-6-8-12-18(25)13-9-7-10-15-21(31-17-19(24)23(29)30)20(26)14-11-16-22(27)28/h6-10,15,18-21,25-26H,2-5,11-14,16-17,24H2,1H3,(H,27,28)(H,29,30)/b8-6-,9-7+,15-10+/t18-,19+,20-,21+/m0/s1

InChI Key

FZJOTYMARNGISF-YXSOTRFDSA-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 hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Hydroxyeicosatrienoic acids

Alternative Parents

Substituents

Hydroxyeicosatrienoic acid
Long-chain fatty acid
Cysteine or derivatives
S-alkyl-l-cysteine
Alpha-amino acid
Alpha-amino acid or derivatives
D-alpha-amino acid
Hydroxy fatty acid
Thia fatty acid
Dicarboxylic acid or derivatives
Fatty acid
Unsaturated fatty acid
Amino acid or derivatives
Amino acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Dialkylthioether
Sulfenyl compound
Thioether
Primary aliphatic amine
Organic oxygen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organosulfur compound
Primary amine
Amine
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	0.45	ALOGPS
logP	1	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	2.35	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	141.08 Å²	ChemAxon
Rotatable Bond Count	19	ChemAxon
Refractivity	128.17 m³·mol⁻¹	ChemAxon
Polarizability	53.02 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

HMDB0012501

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029103

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

53481446

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 10,11-Dihydro-12R-hydroxy-leukotriene E4 (NP0339021)

MOL for NP0339021 (10,11-Dihydro-12R-hydroxy-leukotriene E4)

3D MOL for NP0339021 (10,11-Dihydro-12R-hydroxy-leukotriene E4)

3D SDF for NP0339021 (10,11-Dihydro-12R-hydroxy-leukotriene E4)

3D-SDF for NP0339021 (10,11-Dihydro-12R-hydroxy-leukotriene E4)

PDB for NP0339021 (10,11-Dihydro-12R-hydroxy-leukotriene E4)

3D PDB for NP0339021 (10,11-Dihydro-12R-hydroxy-leukotriene E4)

SMILES for NP0339021 (10,11-Dihydro-12R-hydroxy-leukotriene E4)

INCHI for NP0339021 (10,11-Dihydro-12R-hydroxy-leukotriene E4)

Structure for NP0339021 (10,11-Dihydro-12R-hydroxy-leukotriene E4)

3D Structure for NP0339021 (10,11-Dihydro-12R-hydroxy-leukotriene E4)