NP-MRD: Showing NP-Card for 13E-Tetranor-16-carboxy-LTE4 (NP0339050)

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Record Information

Version

2.0

Created at

2024-09-11 19:26:45 UTC

Updated at

2024-09-11 19:26:45 UTC

NP-MRD ID

NP0339050

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13E-Tetranor-16-carboxy-LTE4

Description

13E-Tetranor-16-carboxy-LTE4, also known as omega-COOH-13E-tetranor-lte4, belongs to the class of organic compounds known as cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Thus, 13E-tetranor-16-carboxy-lte4 is considered to be an eicosanoid lipid molecule. 13E-Tetranor-16-carboxy-LTE4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 13E-tetranor-16-carboxy-LTE4 is a metabolite through lipid oxidation of Leukotriene E4 (LTE4). Cysteinyl leukotrienes (CysLTs) are a family of potent inflammatory mediators that appear to contribute to the pathophysiologic features of allergic rhinitis. Leukotriene E4 (LTE4) is a cysteinyl leukotriene. All mammalian cells except erythrocytes synthesize eicosanoids. The PGs and TXs are collectively identified as prostanoids.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303102016462D          

 28 27  0  0  1  0            999 V2000
   13.8568  -14.8946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4443  -14.1801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8568  -13.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4443  -12.7512    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.8568  -12.0367    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6818  -12.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0943  -11.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9194  -11.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3319  -10.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1569  -10.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5694   -9.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1569   -9.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5694   -8.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1569   -7.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5694   -7.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3944   -7.0354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1569   -6.3209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4443  -11.3223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6193  -11.3223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8568  -10.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4443   -9.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8568   -9.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4443   -8.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6193   -8.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8568   -7.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6193  -14.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2068  -13.4657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2068  -14.8946    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
  2 26  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 18  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 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  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 18 19  1  1  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
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  END


  Mrv1652303102016462D          

 28 27  0  0  1  0            999 V2000
   13.8568  -14.8946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4443  -14.1801    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8568  -13.4657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4443  -12.7512    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.8568  -12.0367    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.6818  -12.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0943  -11.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9194  -11.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3319  -10.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1569  -10.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5694   -9.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1569   -9.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5694   -8.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1569   -7.7499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5694   -7.0354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3944   -7.0354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1569   -6.3209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4443  -11.3223    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.6193  -11.3223    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8568  -10.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4443   -9.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8568   -9.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4443   -8.4643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6193   -8.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8568   -7.7499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6193  -14.1801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2068  -13.4657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2068  -14.8946    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
  2 26  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 18  1  1  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 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  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 18 19  1  1  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
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339050

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C19H27NO7S/c20-14(19(26)27)13-28-16(15(21)9-8-12-18(24)25)10-6-4-2-1-3-5-7-11-17(22)23/h1-7,10,14-16,21H,8-9,11-13,20H2,(H,22,23)(H,24,25)(H,26,27)/b3-1-,4-2+,7-5+,10-6+/t14-,15+,16-/m1/s1

> <INCHI_KEY>
MAFGRSDWXFSHMK-SRKAIYCDSA-N

> <FORMULA>
C19H27NO7S

> <MOLECULAR_WEIGHT>
413.485

> <EXACT_MASS>
413.150822913

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
44.623457950028936

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E,5Z,7E,9E,11R,12S)-11-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-12-hydroxyhexadeca-3,5,7,9-tetraenedioic acid

> <ALOGPS_LOGP>
-0.98

> <JCHEM_LOGP>
-1.0835205558359182

> <ALOGPS_LOGS>
-3.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.273938700421356

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.383187651171233

> <JCHEM_PKA_STRONGEST_BASIC>
9.13006036752924

> <JCHEM_POLAR_SURFACE_AREA>
158.14999999999998

> <JCHEM_REFRACTIVITY>
110.88109999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E,5Z,7E,9E,11R,12S)-11-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-12-hydroxyhexadeca-3,5,7,9-tetraenedioic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-MAR-20         0                                  
HETATM    1  N   UNK     0      25.866 -27.803   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      25.096 -26.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      25.866 -25.136   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0      25.096 -23.802   0.000  0.00  0.00           S+0
HETATM    5  C   UNK     0      25.866 -22.469   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      27.406 -22.469   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      28.176 -21.135   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.716 -21.135   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.486 -19.801   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      32.026 -19.801   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.796 -18.467   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.026 -17.134   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.796 -15.800   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      32.026 -14.466   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      32.796 -13.133   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      34.336 -13.133   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      32.026 -11.799   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      25.096 -21.135   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      23.556 -21.135   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      25.866 -19.801   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.096 -18.467   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      25.866 -17.134   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.096 -15.800   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      23.556 -15.800   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      25.866 -14.466   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      23.556 -26.470   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      22.786 -25.136   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      22.786 -27.803   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   26                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18    5   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                                                            
CONECT   26    2   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   54    0
END

View in JSmol

Synonyms

Value	Source
Omega-COOH-13E-tetranor-lte4	HMDB

Chemical Formula

C₁₉H₂₇NO₇S

Average Mass

413.4850 Da

Monoisotopic Mass

413.15082 Da

IUPAC Name

(3E,5Z,7E,9E,11R,12S)-11-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-12-hydroxyhexadeca-3,5,7,9-tetraenedioic acid

Traditional Name

(3E,5Z,7E,9E,11R,12S)-11-{[(2S)-2-amino-2-carboxyethyl]sulfanyl}-12-hydroxyhexadeca-3,5,7,9-tetraenedioic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C19H27NO7S/c20-14(19(26)27)13-28-16(15(21)9-8-12-18(24)25)10-6-4-2-1-3-5-7-11-17(22)23/h1-7,10,14-16,21H,8-9,11-13,20H2,(H,22,23)(H,24,25)(H,26,27)/b3-1-,4-2+,7-5+,10-6+/t14-,15+,16-/m1/s1

InChI Key

MAFGRSDWXFSHMK-SRKAIYCDSA-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 cysteine and derivatives. Cysteine and derivatives are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Cysteine and derivatives

Alternative Parents

Substituents

Cysteine or derivatives
S-alkyl-l-cysteine
Alpha-amino acid
D-alpha-amino acid
Tricarboxylic acid or derivatives
Hydroxy fatty acid
Thia fatty acid
Fatty acyl
Secondary alcohol
Amino acid
Carboxylic acid
Dialkylthioether
Sulfenyl compound
Thioether
Alcohol
Hydrocarbon derivative
Organic oxide
Primary amine
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Amine
Organic nitrogen 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	-0.98	ALOGPS
logP	-1.1	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	2.38	ChemAxon
pKa (Strongest Basic)	9.13	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	158.15 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	110.88 m³·mol⁻¹	ChemAxon
Polarizability	44.62 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0012575

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029132

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

53481472

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 13E-Tetranor-16-carboxy-LTE4 (NP0339050)

MOL for NP0339050 (13E-Tetranor-16-carboxy-LTE4)

3D MOL for NP0339050 (13E-Tetranor-16-carboxy-LTE4)

3D SDF for NP0339050 (13E-Tetranor-16-carboxy-LTE4)

3D-SDF for NP0339050 (13E-Tetranor-16-carboxy-LTE4)

PDB for NP0339050 (13E-Tetranor-16-carboxy-LTE4)

3D PDB for NP0339050 (13E-Tetranor-16-carboxy-LTE4)

SMILES for NP0339050 (13E-Tetranor-16-carboxy-LTE4)

INCHI for NP0339050 (13E-Tetranor-16-carboxy-LTE4)

Structure for NP0339050 (13E-Tetranor-16-carboxy-LTE4)

3D Structure for NP0339050 (13E-Tetranor-16-carboxy-LTE4)