NP-MRD: Showing NP-Card for Theasaponin A4 (NP0338606)

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Record Information

Version

2.0

Created at

2024-09-11 16:21:18 UTC

Updated at

2024-09-11 16:21:19 UTC

NP-MRD ID

NP0338606

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Theasaponin A4

Description

Theasaponin A4, also known as 4,5-lta4, belongs to the class of organic compounds known as epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain. Thus, theasaponin A4 is considered to be an eicosanoid lipid molecule. Theasaponin A4 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI

 
  Mrv0541 02241221432D          
 
 23 23  0  0  1  0            999 V2000
   11.5734   -8.2682    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.2873   -8.6819    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.4202   -7.7403    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8560   -8.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0010   -8.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1421   -8.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7187   -8.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4284   -8.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4325   -8.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7107   -8.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1462   -8.6819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4287   -7.4817    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9969   -8.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2794   -8.2682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5655   -8.6819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5655   -9.5059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8694  -10.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7956  -10.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2285   -9.4794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9347   -9.8931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6448   -9.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3623   -9.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0761   -9.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  1  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  2  0  0  0  0
 10 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  1  0  0  0  0
 17 18  2  0  0  0  0
 18 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
  2  3  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0338606

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC\C=C/C\C=C/C=C/C=C/C[C@H]1O[C@@H]1CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18-19(23-18)16-17-20(21)22/h6-7,9-14,18-19H,2-5,8,15-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,14-13+/t18-,19-/m1/s1

> <INCHI_KEY>
ANXVUHHMAOYZPG-BOCYDZBOSA-N

> <FORMULA>
C20H30O3

> <MOLECULAR_WEIGHT>
318.4504

> <EXACT_MASS>
318.219494826

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
38.49552295220651

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(2R,3R)-3-[(2E,4E,6Z,9Z)-pentadeca-2,4,6,9-tetraen-1-yl]oxiran-2-yl]propanoic acid

> <ALOGPS_LOGP>
5.99

> <JCHEM_LOGP>
5.287252249333332

> <ALOGPS_LOGS>
-5.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.490069599956588

> <JCHEM_PKA_STRONGEST_BASIC>
-4.204933358642824

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
99.4749

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.38e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,5-leukotriene A4

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      21.604 -15.434   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.936 -16.206   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      23.184 -14.449   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      20.264 -16.206   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      24.269 -15.434   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.932 -15.434   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.608 -16.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.600 -16.206   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.941 -15.434   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      16.260 -15.434   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      28.273 -16.206   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      26.934 -13.966   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      14.928 -16.206   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.588 -15.434   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      12.256 -16.206   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.256 -17.744   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.823 -18.673   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.552 -18.673   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.360 -17.695   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.678 -18.467   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.004 -17.688   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      19.343 -18.446   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.675 -17.666   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    3                                                  
CONECT    3    1    2                                                       
CONECT    4    1    6                                                       
CONECT    5    2    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11   12                                                  
CONECT   10    8   13                                                       
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13   10   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   46    0
END

View in JSmol

Synonyms

Value	Source
(4R,5R,7E,9E,11Z,14Z)-4,5-Epoxy-7,9,11,14-eicosatetraenoic acid	ChEBI
(4R,5R,7E,9E,11Z,14Z)-4,5-Epoxyeicosa-7,9,11,14-tetraenoic acid	ChEBI
4,5-LTA4	ChEBI
4R,5R-Ep 7t9t11c14c-20:4	ChEBI
4R,5R-Ep 7t9t11c14c-C20:4	ChEBI
4R,5R-Epoxy-7E,9E,11Z,14Z-eicosatetraenoic acid	ChEBI
(4R,5R,7E,9E,11Z,14Z)-4,5-Epoxy-7,9,11,14-eicosatetraenoate	Generator
(4R,5R,7E,9E,11Z,14Z)-4,5-Epoxyeicosa-7,9,11,14-tetraenoate	Generator
4R,5R-Epoxy-7E,9E,11Z,14Z-eicosatetraenoate	Generator

Chemical Formula

C₂₀H₃₀O₃

Average Mass

318.4504 Da

Monoisotopic Mass

318.21949 Da

IUPAC Name

3-[(2R,3R)-3-[(2E,4E,6Z,9Z)-pentadeca-2,4,6,9-tetraen-1-yl]oxiran-2-yl]propanoic acid

Traditional Name

4,5-leukotriene A4

CAS Registry Number

Not Available

SMILES

CCCCC\C=C/C\C=C/C=C/C=C/C[C@H]1O[C@@H]1CCC(O)=O

InChI Identifier

InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18-19(23-18)16-17-20(21)22/h6-7,9-14,18-19H,2-5,8,15-17H2,1H3,(H,21,22)/b7-6-,10-9-,12-11+,14-13+/t18-,19-/m1/s1

InChI Key

ANXVUHHMAOYZPG-BOCYDZBOSA-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 epoxy fatty acids. These are fatty acids containing an oxirane ring as part of the aliphatic chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Epoxy fatty acids

Alternative Parents

Substituents

Epoxy fatty acid
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

leukotriene (CHEBI:28367 )
polyunsaturated fatty acid (CHEBI:28367 )
epoxy fatty acid (CHEBI:28367 )
Leukotrienes (LMFA03020034 )

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	5.99	ALOGPS
logP	5.29	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.49	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	99.47 m³·mol⁻¹	ChemAxon
Polarizability	38.5 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB001830

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02645

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5280534

PDB ID

Not Available

ChEBI ID

28367

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Theasaponin A4 (NP0338606)

MOL for NP0338606 (Theasaponin A4)

3D MOL for NP0338606 (Theasaponin A4)

3D SDF for NP0338606 (Theasaponin A4)

3D-SDF for NP0338606 (Theasaponin A4)

PDB for NP0338606 (Theasaponin A4)

3D PDB for NP0338606 (Theasaponin A4)

SMILES for NP0338606 (Theasaponin A4)

INCHI for NP0338606 (Theasaponin A4)

Structure for NP0338606 (Theasaponin A4)

3D Structure for NP0338606 (Theasaponin A4)