NP-MRD: Showing NP-Card for 15-Epi-lipoxin B5 (NP0339054)

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Record Information

Version

2.0

Created at

2024-09-11 19:27:51 UTC

Updated at

2024-09-11 19:27:52 UTC

NP-MRD ID

NP0339054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-Epi-lipoxin B5

Description

15-Epi-lipoxin B5 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, 15-epi-lipoxin B5 is considered to be an eicosanoid lipid molecule. Lipoxins (LXs) and aspirin-triggered Lipoxin (ATL) are trihydroxytetraene-containing eicosanoids generated from arachidonic acid that are distinct in structure, formation, and function from the many other proinflammatory lipid-derived mediators. These eicosanoids (i.E., LXA4 and ATL) with a unique trihydroxytetraene structure function as 'stop signals' in inflammation and actively participate in dampening host responses to bring the inflammation to a close, namely, resolution. These endogenous eicosanoids have now emerged as founding members of the first class of lipid/chemical mediators involved in the resolution of the inflammatory response. This phenomenon is an active process that is governed by specific lipid mediators and involves a series of well-orchestrated temporal events. Lipoxin A4 (LXA4), ATL, and their metabolic stable analogs elicit cellular responses and regulate leukocyte trafficking in vivo by activating the specific receptor, ALX. 15-Epi-lipoxin B5 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Thus, potent locally released mediators serve as checkpoint controllers of inflammation. In addition to the well-appreciated ability of aspirin to inhibit PGs, aspirin also acetylates cyclooxygenase (COX)-2, triggering the formation of a 15-epimeric form of lipoxins, termed aspirin-triggered LXA4 (ATL). LXA4 and ATL elicit the multicellular responses via a specific G protein-coupled receptor (GPCR) termed ALX that has been identified in human.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208072D          

 25 24  0  0  1  0            999 V2000
   10.8748  -11.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6998  -11.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1123  -12.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9373  -12.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3498  -11.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1748  -11.3878    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.5873  -10.6733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5873  -12.1022    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.4123  -12.1022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1748  -12.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3498  -12.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9373  -13.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1123  -13.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6998  -14.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8748  -14.2456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4623  -13.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6373  -13.5312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2248  -12.8167    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.3998  -12.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6373  -12.1022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2248  -11.3878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6373  -10.6733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2248   -9.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6373   -9.2443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3998   -9.9588    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  2  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  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 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
 23 25  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339054

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/c1-2-3-8-14-18(22)19(23)15-10-7-5-4-6-9-12-17(21)13-11-16-20(24)25/h3-10,12,15,17-19,21-23H,2,11,13-14,16H2,1H3,(H,24,25)/b6-4-,7-5+,8-3-,12-9+,15-10+/t17-,18+,19+/m0/s1

> <INCHI_KEY>
VLLDKSJDBRLUOY-XIFXWWOOSA-N

> <FORMULA>
C20H30O5

> <MOLECULAR_WEIGHT>
350.4492

> <EXACT_MASS>
350.20932407

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.957342772537

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,6E,8Z,10E,12E,14R,15R,17Z)-5,14,15-trihydroxyicosa-6,8,10,12,17-pentaenoic acid

> <ALOGPS_LOGP>
4.32

> <JCHEM_LOGP>
2.688723413333333

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.63192684397179

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.646344730749973

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5455178992223586

> <JCHEM_POLAR_SURFACE_AREA>
97.99000000000001

> <JCHEM_REFRACTIVITY>
105.46309999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.93e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6E,8Z,10E,12E,14R,15R,17Z)-5,14,15-trihydroxyicosa-6,8,10,12,17-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      20.300 -21.257   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.840 -21.257   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.610 -22.591   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.150 -22.591   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.920 -21.257   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.460 -21.257   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      27.230 -19.923   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      27.230 -22.591   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      28.770 -22.591   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      26.460 -23.925   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.920 -23.925   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.150 -25.258   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.610 -25.258   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.840 -26.592   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.300 -26.592   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.530 -25.258   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.990 -25.258   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.220 -23.925   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      15.680 -23.925   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      17.990 -22.591   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      17.220 -21.257   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      17.990 -19.923   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      17.220 -18.590   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      17.990 -17.256   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      15.680 -18.590   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    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   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   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

View in JSmol

Synonyms

Value	Source
5(S),14(R),15(S)-Trihydroxy-6E,8Z,10E,12E,17Z-eicosapentaenoate	HMDB
5(S),14(R),15(S)-Trihydroxy-6E,8Z,10E,12E,17Z-eicosapentaenoic acid	HMDB
5(S),14(R),15(S)-Trihydroxy-6E,8Z,10E,12E,17Z-eicosapentaenoic acid anion	HMDB

Chemical Formula

C₂₀H₃₀O₅

Average Mass

350.4492 Da

Monoisotopic Mass

350.20932 Da

IUPAC Name

(5R,6E,8Z,10E,12E,14R,15R,17Z)-5,14,15-trihydroxyicosa-6,8,10,12,17-pentaenoic acid

Traditional Name

(5R,6E,8Z,10E,12E,14R,15R,17Z)-5,14,15-trihydroxyicosa-6,8,10,12,17-pentaenoic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O5/c1-2-3-8-14-18(22)19(23)15-10-7-5-4-6-9-12-17(21)13-11-16-20(24)25/h3-10,12,15,17-19,21-23H,2,11,13-14,16H2,1H3,(H,24,25)/b6-4-,7-5+,8-3-,12-9+,15-10+/t17-,18+,19+/m0/s1

InChI Key

VLLDKSJDBRLUOY-XIFXWWOOSA-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
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organooxygen compound
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	4.32	ALOGPS
logP	2.69	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.65	ChemAxon
pKa (Strongest Basic)	-1.5	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	13	ChemAxon
Refractivity	105.46 m³·mol⁻¹	ChemAxon
Polarizability	39.96 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

HMDB0012588

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029136

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

53481476

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 15-Epi-lipoxin B5 (NP0339054)

MOL for NP0339054 (15-Epi-lipoxin B5)

3D MOL for NP0339054 (15-Epi-lipoxin B5)

3D SDF for NP0339054 (15-Epi-lipoxin B5)

3D-SDF for NP0339054 (15-Epi-lipoxin B5)

PDB for NP0339054 (15-Epi-lipoxin B5)

3D PDB for NP0339054 (15-Epi-lipoxin B5)

SMILES for NP0339054 (15-Epi-lipoxin B5)

INCHI for NP0339054 (15-Epi-lipoxin B5)

Structure for NP0339054 (15-Epi-lipoxin B5)

3D Structure for NP0339054 (15-Epi-lipoxin B5)