Showing NP-Card for 10,11-Dihydro-12-oxo-LTB4 (NP0339020)

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Record Information
Version2.0
Created at2024-09-11 19:17:02 UTC
Updated at2024-09-11 19:17:03 UTC
NP-MRD IDNP0339020
Secondary Accession NumbersNone
Natural Product Identification
Common Name10,11-Dihydro-12-oxo-LTB4
Description10,11-Dihydro-12-oxo-LTB4, also known as 12-oxo-10,11-dihydro-LTB(,4), 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-12-oxo-LTB4 is considered to be an eicosanoid lipid molecule. The PGs and TXs are collectively identified as prostanoids. 10,11-Dihydro-12-oxo-LTB4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. LTB4 is the major metabolite in neutrophil polymorphonuclear leukocytes. Leukotrienes are eicosanoids. All mammalian cells except erythrocytes synthesize eicosanoids. Leukotrienes are metabolites of arachidonic acid derived from the action of 5-LO (5-lipoxygenase). 10,11-Dihydro-12-oxo-LTB4 was first documented in 1996 (PMID: 8632343). 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.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339020 (10,11-Dihydro-12-oxo-LTB4)

  Mrv0541 02251208062D          

 24 23  0  0  1  0            999 V2000
   14.5527  -10.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5527  -10.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8382  -11.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8382  -12.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1238  -12.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1238  -13.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4093  -13.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6948  -13.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9804  -13.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2659  -13.4605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9804  -14.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6948  -15.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6948  -15.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4093  -16.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4093  -17.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1238  -17.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8382  -17.1731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8382  -16.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5527  -17.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5527  -18.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2672  -18.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2672  -19.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5527  -20.0606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9817  -20.0606    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  2  0  0  0  0
  9 11  1  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  2  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
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3D MOL for NP0339020 (10,11-Dihydro-12-oxo-LTB4)

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3D SDF for NP0339020 (10,11-Dihydro-12-oxo-LTB4)
  Mrv0541 02251208062D          

 24 23  0  0  1  0            999 V2000
   14.5527  -10.1605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5527  -10.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8382  -11.3980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8382  -12.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1238  -12.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1238  -13.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4093  -13.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6948  -13.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9804  -13.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2659  -13.4605    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9804  -14.6980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6948  -15.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6948  -15.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4093  -16.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4093  -17.1731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1238  -17.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8382  -17.1731    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8382  -16.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5527  -17.5856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5527  -18.4106    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2672  -18.8231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2672  -19.6481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5527  -20.0606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.9817  -20.0606    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  2  0  0  0  0
  9 11  1  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  2  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>
NP0339020

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-9,11,15,19,22H,2-5,10,12-14,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,15-11-/t19-/m0/s1

> <INCHI_KEY>
AHHXLFNPCWCNQF-SOOJVSLFSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.81931127096303

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,6Z,8E,14Z)-5-hydroxy-12-oxoicosa-6,8,14-trienoic acid

> <ALOGPS_LOGP>
4.57

> <JCHEM_LOGP>
4.539063675333334

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.448224032492426

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.58410162972704

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5455147157558118

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
100.9943

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.04e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6Z,8E,14Z)-5-hydroxy-12-oxoicosa-6,8,14-trienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0339020 (10,11-Dihydro-12-oxo-LTB4)
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PDB for NP0339020 (10,11-Dihydro-12-oxo-LTB4)
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      27.165 -18.966   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.165 -20.506   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.831 -21.276   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      25.831 -22.816   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.498 -23.586   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      24.498 -25.126   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      23.164 -25.896   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      21.830 -25.126   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.497 -25.896   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      19.163 -25.126   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      20.497 -27.436   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      21.830 -28.206   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.830 -29.746   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.164 -30.516   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.164 -32.056   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.498 -32.826   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      25.831 -32.056   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      25.831 -30.516   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      27.165 -32.826   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.165 -34.366   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.499 -35.136   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      28.499 -36.676   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      27.165 -37.446   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      29.833 -37.446   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

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3D PDB for NP0339020 (10,11-Dihydro-12-oxo-LTB4)
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SMILES for NP0339020 (10,11-Dihydro-12-oxo-LTB4)
CCCCC\C=C/CC(=O)CC\C=C\C=C/[C@H](O)CCCC(O)=O
Download
INCHI for NP0339020 (10,11-Dihydro-12-oxo-LTB4)
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-9,11,15,19,22H,2-5,10,12-14,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,15-11-/t19-/m0/s1
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View in JSmol
Synonyms
ValueSource
12-oxo-(5S)-Hydroxy-(6Z,8E,14Z)-eicosatrienoateHMDB
12-oxo-(5S)-Hydroxy-(6Z,8E,14Z)-eicosatrienoic acidHMDB
12-oxo-(5S)-Hydroxy-(6Z,8E,14Z)-eicosatrienoic acid anionHMDB
12-oxo-10,11-Dihydro-LTB(,4)HMDB
Chemical FormulaC20H32O4
Average Mass336.4657 Da
Monoisotopic Mass336.23006 Da
IUPAC Name(5R,6Z,8E,14Z)-5-hydroxy-12-oxoicosa-6,8,14-trienoic acid
Traditional Name(5R,6Z,8E,14Z)-5-hydroxy-12-oxoicosa-6,8,14-trienoic acid
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/CC(=O)CC\C=C\C=C/[C@H](O)CCCC(O)=O
InChI Identifier
InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-9,11,15,19,22H,2-5,10,12-14,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,15-11-/t19-/m0/s1
InChI KeyAHHXLFNPCWCNQF-SOOJVSLFSA-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 hydroxyeicosatrienoic acids. These are eicosanoic acids with an attached hydroxyl group and three CC double bonds.
KingdomOrganic compounds  
Super ClassLipids and lipid-like molecules  
ClassFatty Acyls  
Sub ClassEicosanoids  
Direct ParentHydroxyeicosatrienoic acids  
Alternative Parents
Substituents
  • Hydroxyeicosatrienoic acid
    • 

  • Long-chain fatty acid
    • 

  • Hydroxy fatty acid
    • 

  • Keto fatty acid
    • 

  • Fatty acid
    • 

  • Unsaturated fatty acid
    • 

  • Ketone
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organooxygen compound
    • 

  • Alcohol
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organic oxygen compound
    • 

  • Carbonyl group
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
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
logP4.57ALOGPS
logP4.54ChemAxon
logS-4.5ALOGPS
pKa (Strongest Acidic)4.58ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity100.99 m³·mol⁻¹ChemAxon
Polarizability38.82 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012498  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029102  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53481445  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Powell WS, Rokach J, Khanapure SP, Manna S, Hashefi M, Gravel S, Macleod RJ, Falck JR, Bhatt RK: Effects of metabolites of leukotriene B4 on human neutrophil migration and cytosolic calcium levels. J Pharmacol Exp Ther. 1996 Feb;276(2):728-36. [PubMed:8632343  ]