NP-MRD: Showing NP-Card for 6,7-Dihydro-12-epi-LTB4 (NP0339096)

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Record Information

Version

2.0

Created at

2024-09-11 19:39:48 UTC

Updated at

2024-09-11 19:39:48 UTC

NP-MRD ID

NP0339096

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6,7-Dihydro-12-epi-LTB4

Description

6,7-Dihydro-12-epi-LTB4, also known as 5S12Sectr, 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, 6,7-dihydro-12-epi-LTB4 is considered to be an eicosanoid lipid molecule. The PGs and TXs are collectively identified as prostanoids. 6,7-Dihydro-12-epi-LTB4 is formed when leukotriene B4 (LTB4) is metabolized by beta-oxidation. 6,7-Dihydro-12-epi-LTB4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Biologically active LTB4 is metabolized by w-oxidation carried out by specific cytochrome P450s (CYP4F) followed by beta-oxidation from the w-carboxy position and after CoA ester formation. The immediate product of 5-LO is LTA4 (leukotriene A4), which is enzymatically converted into either LTB4 (leukotriene B4) by LTA4 hydrolase or LTC4 (leukotriene C4) by LTC4 synthase. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). All mammalian cells except erythrocytes synthesize eicosanoids.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208102D          

 24 23  0  0  1  0            999 V2000
   14.4217  -15.7558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1362  -16.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1362  -16.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8506  -17.4059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8506  -18.2309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5651  -18.6434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5651  -19.4684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8506  -19.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8506  -20.7059    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.5651  -21.1184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.1362  -21.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4217  -20.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7072  -21.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9928  -20.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2782  -21.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5638  -20.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8493  -21.1184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8493  -21.9434    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1348  -20.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4203  -21.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7059  -20.7059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9914  -21.1184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2769  -20.7059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9914  -21.9434    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  1  0  0  0
  9 11  1  0  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  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  6  0  0  0
 17 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
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339096

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-10,14,18-19,21-22H,2-5,11-13,15-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+/t18-,19+/m1/s1

> <INCHI_KEY>
ZMZNVSWCIRFLBV-GRXSAWGRSA-N

> <FORMULA>
C20H34O4

> <MOLECULAR_WEIGHT>
338.4816

> <EXACT_MASS>
338.245709576

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
41.031057785559184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,8E,10E,12R,14Z)-5,12-dihydroxyicosa-8,10,14-trienoic acid

> <ALOGPS_LOGP>
5.79

> <JCHEM_LOGP>
4.331562873666666

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.72082644168118

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.707760451946075

> <JCHEM_PKA_STRONGEST_BASIC>
-1.05971735137605

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
102.02239999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,8E,10E,12R,14Z)-5,12-dihydroxyicosa-8,10,14-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      26.921 -29.411   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.254 -30.181   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.254 -31.721   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.588 -32.491   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.588 -34.031   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.922 -34.801   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      30.922 -36.341   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.588 -37.111   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      29.588 -38.651   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      30.922 -39.421   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      28.254 -39.421   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.921 -38.651   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.587 -39.421   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.253 -38.651   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      22.919 -39.421   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      21.586 -38.651   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.252 -39.421   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      20.252 -40.961   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      18.918 -38.651   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      17.585 -39.421   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      16.251 -38.651   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.917 -39.421   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.584 -38.651   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      14.917 -40.961   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                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   46    0
END

View in JSmol

Synonyms

Value	Source
(5S,12S)-Dihydroxy-(8E,10E,14Z)-eicosatrienoate	HMDB
(5S,12S)-Dihydroxy-(8E,10E,14Z)-eicosatrienoic acid	HMDB
5S12SECtr	HMDB
6,7-Dihydro-12-epi-leukotriene b(,4)	HMDB

Chemical Formula

C₂₀H₃₄O₄

Average Mass

338.4816 Da

Monoisotopic Mass

338.24571 Da

IUPAC Name

(5R,8E,10E,12R,14Z)-5,12-dihydroxyicosa-8,10,14-trienoic acid

Traditional Name

(5R,8E,10E,12R,14Z)-5,12-dihydroxyicosa-8,10,14-trienoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H34O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-10,14,18-19,21-22H,2-5,11-13,15-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+/t18-,19+/m1/s1

InChI Key

ZMZNVSWCIRFLBV-GRXSAWGRSA-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
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	5.79	ALOGPS
logP	4.33	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.71	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	102.02 m³·mol⁻¹	ChemAxon
Polarizability	41.03 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

HMDB0012838

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029182

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

53481527

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 6,7-Dihydro-12-epi-LTB4 (NP0339096)

MOL for NP0339096 (6,7-Dihydro-12-epi-LTB4)

3D MOL for NP0339096 (6,7-Dihydro-12-epi-LTB4)

3D SDF for NP0339096 (6,7-Dihydro-12-epi-LTB4)

3D-SDF for NP0339096 (6,7-Dihydro-12-epi-LTB4)

PDB for NP0339096 (6,7-Dihydro-12-epi-LTB4)

3D PDB for NP0339096 (6,7-Dihydro-12-epi-LTB4)

SMILES for NP0339096 (6,7-Dihydro-12-epi-LTB4)

INCHI for NP0339096 (6,7-Dihydro-12-epi-LTB4)

Structure for NP0339096 (6,7-Dihydro-12-epi-LTB4)

3D Structure for NP0339096 (6,7-Dihydro-12-epi-LTB4)