NP-MRD: Showing NP-Card for 18E-20-oxo-20-CoA-LTB4 (NP0339065)

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Record Information

Version

2.0

Created at

2024-09-11 19:31:28 UTC

Updated at

2024-09-11 19:31:28 UTC

NP-MRD ID

NP0339065

Secondary Accession Numbers

None

Natural Product Identification

Common Name

18E-20-oxo-20-CoA-LTB4

Description

18E-20-oxo-20-CoA-LTB4 belongs to the class of organic compounds known as long-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 2-enoyl chain of 13 to 21 carbon atoms. 18E-20-oxo-20-CoA-LTB4 is a very strong basic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208082D          

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M  CHG  4   7  -1  11  -1  23  -1  24  -1
M  END


  Mrv0541 02251208082D          

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 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  2  0  0  0  0
 43 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  2  0  0  0  0
 49 51  1  0  0  0  0
 51 52  2  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  2  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  6  0  0  0
 58 60  1  0  0  0  0
 60 61  2  0  0  0  0
 61 62  1  0  0  0  0
 62 63  2  0  0  0  0
 63 64  1  0  0  0  0
 64 65  2  0  0  0  0
 65 66  1  0  0  0  0
 66 67  1  6  0  0  0
 66 68  1  0  0  0  0
 68 69  1  0  0  0  0
 69 70  1  0  0  0  0
 70 71  1  0  0  0  0
 71 72  1  0  0  0  0
 71 73  2  0  0  0  0
M  CHG  4   7  -1  11  -1  23  -1  24  -1
M  END
> <DATABASE_ID>
NP0339065

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H](CCCC(O)=O)\C=C/C=C/C=C/[C@@H](O)C\C=C/CC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@@H](O)[C@H]1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C41H62N7O21P3S/c1-41(2,24-66-72(63,64)69-71(61,62)65-23-29-35(68-70(58,59)60)34(55)40(67-29)48-26-47-33-37(42)45-25-46-38(33)48)36(56)39(57)44-20-19-30(51)43-21-22-73-32(54)18-11-5-3-4-8-13-27(49)14-9-6-7-10-15-28(50)16-12-17-31(52)53/h4,6-11,14-15,18,25-29,34-36,40,49-50,55-56H,3,5,12-13,16-17,19-24H2,1-2H3,(H,43,51)(H,44,57)(H,52,53)(H,61,62)(H,63,64)(H2,42,45,46)(H2,58,59,60)/p-4/b7-6+,8-4-,14-9+,15-10-,18-11+/t27-,28-,29+,34-,35-,36?,40+/m0/s1

> <INCHI_KEY>
PBPMTFAECBJRFW-KBPAAJSHSA-J

> <FORMULA>
C41H58N7O21P3S

> <MOLECULAR_WEIGHT>
1109.92

> <EXACT_MASS>
1109.261932179

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
105.16871635785289

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-({2-[(2-{[(2E,6Z,9S,10E,12E,14Z,16R)-19-carboxy-9,16-dihydroxynonadeca-2,6,10,12,14-pentaenoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropyl ({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate

> <ALOGPS_LOGP>
1.96

> <JCHEM_LOGP>
-3.716080288297545

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
2.674784178119324

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8251831305403119

> <JCHEM_PKA_STRONGEST_BASIC>
5.1012985271112345

> <JCHEM_POLAR_SURFACE_AREA>
452.71

> <JCHEM_REFRACTIVITY>
260.8212000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
34

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.21e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-({2-[(2-{[(2E,6Z,9S,10E,12E,14Z,16R)-19-carboxy-9,16-dihydroxynonadeca-2,6,10,12,14-pentaenoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropyl {[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate

> <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      14.424 -23.315   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      15.329 -24.560   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.234 -25.806   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.575 -23.655   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      16.414 -22.124   0.000  0.00  0.00           O+0
HETATM    6  P   UNK     0      17.660 -21.219   0.000  0.00  0.00           P+0
HETATM    7  O   UNK     0      16.755 -19.973   0.000  0.00  0.00           O-1
HETATM    8  O   UNK     0      18.565 -22.464   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      18.906 -20.313   0.000  0.00  0.00           O+0
HETATM   10  P   UNK     0      18.745 -18.782   0.000  0.00  0.00           P+0
HETATM   11  O   UNK     0      17.213 -18.943   0.000  0.00  0.00           O-1
HETATM   12  O   UNK     0      20.277 -18.621   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      18.584 -17.250   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      17.177 -16.624   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      17.016 -15.092   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      15.682 -14.322   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      16.003 -12.816   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      17.534 -12.655   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      18.304 -11.321   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      18.161 -14.062   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      19.667 -14.382   0.000  0.00  0.00           O+0
HETATM   22  P   UNK     0      20.143 -15.847   0.000  0.00  0.00           P+0
HETATM   23  O   UNK     0      18.678 -16.323   0.000  0.00  0.00           O-1
HETATM   24  O   UNK     0      21.608 -15.371   0.000  0.00  0.00           O-1
HETATM   25  O   UNK     0      20.619 -17.311   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0      14.972 -11.671   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      13.441 -11.832   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0      12.814 -10.426   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      13.959  -9.395   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.959  -7.855   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0      12.625  -7.085   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0      15.292  -7.085   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      16.626  -7.855   0.000  0.00  0.00           C+0
HETATM   34  N   UNK     0      16.626  -9.395   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0      15.292 -10.165   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      14.083 -25.466   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      12.677 -24.839   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      14.244 -26.997   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      12.999 -27.903   0.000  0.00  0.00           O+0
HETATM   40  N   UNK     0      15.651 -27.624   0.000  0.00  0.00           N+0
HETATM   41  C   UNK     0      16.897 -26.719   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      18.304 -27.345   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      19.550 -26.440   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      19.389 -24.908   0.000  0.00  0.00           O+0
HETATM   45  N   UNK     0      20.957 -27.066   0.000  0.00  0.00           N+0
HETATM   46  C   UNK     0      22.203 -26.161   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      23.610 -26.787   0.000  0.00  0.00           C+0
HETATM   48  S   UNK     0      24.855 -25.882   0.000  0.00  0.00           S+0
HETATM   49  C   UNK     0      26.262 -26.508   0.000  0.00  0.00           C+0
HETATM   50  O   UNK     0      26.423 -28.040   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0      27.508 -25.603   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      27.347 -24.072   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      28.593 -23.166   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      28.432 -21.635   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      29.678 -20.730   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      29.517 -19.198   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      28.110 -18.572   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      27.949 -17.040   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0      26.542 -16.414   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0      29.195 -16.135   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      29.034 -14.603   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      30.280 -13.698   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      30.119 -12.167   0.000  0.00  0.00           C+0
HETATM   64  C   UNK     0      31.365 -11.261   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0      31.204  -9.730   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      29.797  -9.103   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0      28.551 -10.009   0.000  0.00  0.00           O+0
HETATM   68  C   UNK     0      29.636  -7.572   0.000  0.00  0.00           C+0
HETATM   69  C   UNK     0      28.229  -6.945   0.000  0.00  0.00           C+0
HETATM   70  C   UNK     0      28.068  -5.414   0.000  0.00  0.00           C+0
HETATM   71  C   UNK     0      26.661  -4.787   0.000  0.00  0.00           C+0
HETATM   72  O   UNK     0      26.500  -3.256   0.000  0.00  0.00           O+0
HETATM   73  O   UNK     0      25.416  -5.693   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   36                                             
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8    9                                             
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   26                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   15   18   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   17   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   26   29   34                                                  
CONECT   36    2   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43                                                            
CONECT   45   43   46                                                       
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49                                                            
CONECT   51   49   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59   60                                                  
CONECT   59   58                                                            
CONECT   60   58   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   70   72   73                                                  
CONECT   72   71                                                            
CONECT   73   71                                                            
MASTER        0    0    0    0    0    0    0    0   73    0  150    0
END

View in JSmol

Synonyms

Value	Source
CoA-20-COOH-19E-LTB(,4)	HMDB
coenzyme A-20-COOH-19E-LTB(,4)	HMDB

Chemical Formula

C₄₁H₅₈N₇O₂₁P₃S

Average Mass

1109.9200 Da

Monoisotopic Mass

1109.26193 Da

IUPAC Name

3-({2-[(2-{[(2E,6Z,9S,10E,12E,14Z,16R)-19-carboxy-9,16-dihydroxynonadeca-2,6,10,12,14-pentaenoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropyl ({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate

Traditional Name

3-({2-[(2-{[(2E,6Z,9S,10E,12E,14Z,16R)-19-carboxy-9,16-dihydroxynonadeca-2,6,10,12,14-pentaenoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-3-hydroxy-2,2-dimethylpropyl {[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate

CAS Registry Number

Not Available

SMILES

O[C@H](CCCC(O)=O)\C=C/C=C/C=C/[C@@H](O)C\C=C/CC\C=C\C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@@H](O)[C@H]1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C41H62N7O21P3S/c1-41(2,24-66-72(63,64)69-71(61,62)65-23-29-35(68-70(58,59)60)34(55)40(67-29)48-26-47-33-37(42)45-25-46-38(33)48)36(56)39(57)44-20-19-30(51)43-21-22-73-32(54)18-11-5-3-4-8-13-27(49)14-9-6-7-10-15-28(50)16-12-17-31(52)53/h4,6-11,14-15,18,25-29,34-36,40,49-50,55-56H,3,5,12-13,16-17,19-24H2,1-2H3,(H,43,51)(H,44,57)(H,52,53)(H,61,62)(H,63,64)(H2,42,45,46)(H2,58,59,60)/p-4/b7-6+,8-4-,14-9+,15-10-,18-11+/t27-,28-,29+,34-,35-,36?,40+/m0/s1

InChI Key

PBPMTFAECBJRFW-KBPAAJSHSA-J

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 long-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a long-chain 2-enoyl chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-chain 2-enoyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Pentose phosphate
Ribonucleoside 3'-phosphate
Pentose-5-phosphate
Long-chain fatty acid
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Aminopyrimidine
Hydroxy fatty acid
Thia fatty acid
Fatty acid
Imidolactam
Fatty amide
Alkyl phosphate
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Unsaturated fatty acid
Pyrimidine
Tetrahydrofuran
Heteroaromatic compound
Imidazole
Azole
Thiocarboxylic acid ester
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Amino acid
Carbothioic s-ester
Amino acid or derivatives
Sulfenyl compound
Azacycle
Organoheterocyclic compound
Carboxylic acid
Oxacycle
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Thiocarboxylic acid or derivatives
Organosulfur compound
Organic nitrogen compound
Organonitrogen compound
Primary amine
Carbonyl group
Hydrocarbon derivative
Alcohol
Amine
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organic oxide
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	1.96	ALOGPS
logP	-3.7	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	5.1	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	452.71 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	260.82 m³·mol⁻¹	ChemAxon
Polarizability	105.17 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029147

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

53481492

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 18E-20-oxo-20-CoA-LTB4 (NP0339065)

MOL for NP0339065 (18E-20-oxo-20-CoA-LTB4)

3D MOL for NP0339065 (18E-20-oxo-20-CoA-LTB4)

3D SDF for NP0339065 (18E-20-oxo-20-CoA-LTB4)

3D-SDF for NP0339065 (18E-20-oxo-20-CoA-LTB4)

PDB for NP0339065 (18E-20-oxo-20-CoA-LTB4)

3D PDB for NP0339065 (18E-20-oxo-20-CoA-LTB4)

SMILES for NP0339065 (18E-20-oxo-20-CoA-LTB4)

INCHI for NP0339065 (18E-20-oxo-20-CoA-LTB4)

Structure for NP0339065 (18E-20-oxo-20-CoA-LTB4)

3D Structure for NP0339065 (18E-20-oxo-20-CoA-LTB4)