NP-MRD: Showing NP-Card for 8-Isoprostaglandin E1 (NP0334733)

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Record Information

Version

2.0

Created at

2024-09-10 19:43:38 UTC

Updated at

2024-09-10 19:43:38 UTC

NP-MRD ID

NP0334733

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-Isoprostaglandin E1

Description

8-Isoprostaglandin E1, also known as iso-pge1 or ovinonic acid, belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid. Thus, 8-isoprostaglandin E1 is considered to be an eicosanoid lipid molecule. Thus, a total of 64 isomers can be generated for each of the D-, E-, and F{alpha}-ring isoprostanes. 8-Isoprostaglandin E1 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signaling pathways. Nevertheless, isoprostanes are isomeric with prostaglandins and have been given the prefix D-, E-, and F{alpha}- to denote the prostane ring shared with PGD2, PGE2, and PGF2{alpha} respectively. Prostaglandins are eicosanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes) and leukotrienes from leukocytes, hence the derivation of their names. The isoprostanes embody a vast family of novel prostaglandin-like lipids that are produced by nonenzymatic peroxidation of arachidonic acid (AA) in response to free radicals and reactive oxygen species.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 02231219582D          

 25 25  0  0  1  0            999 V2000
   23.4852  -19.5224    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1356  -21.2294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0331  -16.8174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7746  -20.9658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2162  -19.6067    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3656  -19.7774    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.0331  -19.2925    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   22.7005  -19.7774    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.4456  -20.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5810  -19.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6206  -20.5620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9679  -20.0745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0331  -18.4674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1832  -19.8196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7475  -18.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5701  -20.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7475  -17.2299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.4620  -16.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7855  -20.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4620  -15.9924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1724  -20.6687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1766  -15.5799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1766  -14.7549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3877  -20.4137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8910  -14.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  1  1  6  0  0  0
  2 11  2  0  0  0  0
 17  3  1  1  0  0  0
  4 24  1  0  0  0  0
  5 24  2  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  1  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 13  1  1  0  0  0
  8  9  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 16 19  1  0  0  0  0
 17 18  1  0  0  0  0
 18 20  1  0  0  0  0
 19 21  1  0  0  0  0
 20 22  1  0  0  0  0
 21 24  1  0  0  0  0
 22 23  1  0  0  0  0
 23 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334733

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@H]1CCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16-,17+,19+/m0/s1

> <INCHI_KEY>
GMVPRGQOIOIIMI-JCPCGATGSA-N

> <FORMULA>
C20H34O5

> <MOLECULAR_WEIGHT>
354.481

> <EXACT_MASS>
354.240624198

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
41.51397882505392

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[(1S,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
3.5871917936666664

> <ALOGPS_LOGS>
-3.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.680474481265463

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.353232088584439

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6263175145935014

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
98.31849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
iso-PGE1

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      43.839 -36.442   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      39.453 -39.628   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      41.128 -31.392   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      29.446 -39.136   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      30.270 -36.599   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      39.882 -36.918   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      41.128 -36.013   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      42.374 -36.918   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      41.898 -38.382   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      38.418 -36.442   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      40.358 -38.382   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      37.273 -37.472   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      41.128 -34.472   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.809 -36.997   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      42.462 -33.702   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      34.664 -38.027   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      42.462 -32.162   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      43.796 -31.392   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.200 -37.551   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      43.796 -29.852   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      32.055 -38.582   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      45.130 -29.082   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      45.130 -27.542   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      30.590 -38.106   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      46.463 -26.772   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2   11                                                            
CONECT    3   17                                                            
CONECT    4   24                                                            
CONECT    5   24                                                            
CONECT    6    7   10   11                                                  
CONECT    7    6    8   13                                                  
CONECT    8    1    7    9                                                  
CONECT    9    8   11                                                       
CONECT   10    6   12                                                       
CONECT   11    2    6    9                                                  
CONECT   12   10   14                                                       
CONECT   13    7   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17                                                       
CONECT   16   14   19                                                       
CONECT   17    3   15   18                                                  
CONECT   18   17   20                                                       
CONECT   19   16   21                                                       
CONECT   20   18   22                                                       
CONECT   21   19   24                                                       
CONECT   22   20   23                                                       
CONECT   23   22   25                                                       
CONECT   24    4    5   21                                                  
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   50    0
END

View in JSmol

Synonyms

Value	Source
Isoprostaglandin e1, (8beta,11beta,12alpha,13E,15R)-isomer	HMDB
Isoprostaglandin e1	HMDB
Isoprostaglandin e1, (8beta,11alpha,12alpha,13E,15S)-isomer	HMDB
Iso-pge1	HMDB
Isoprostaglandin e1, (8beta,11beta,12alpha,13E,15S)-isomer	HMDB
11a,15-(S)-Dihydroxy-9-oxo-13-trans-8-isoprostenoate	HMDB
11a,15-(S)-Dihydroxy-9-oxo-13-trans-8-isoprostenoic acid	HMDB
8-Iso-pge1	HMDB
Ovinonic acid	HMDB

Chemical Formula

C₂₀H₃₄O₅

Average Mass

354.4810 Da

Monoisotopic Mass

354.24062 Da

IUPAC Name

7-[(1S,2R,3R)-3-hydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoic acid

Traditional Name

iso-PGE1

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@H]1CCCCCCC(O)=O

InChI Identifier

InChI=1S/C20H34O5/c1-2-3-6-9-15(21)12-13-17-16(18(22)14-19(17)23)10-7-4-5-8-11-20(24)25/h12-13,15-17,19,21,23H,2-11,14H2,1H3,(H,24,25)/b13-12+/t15-,16-,17+,19+/m0/s1

InChI Key

GMVPRGQOIOIIMI-JCPCGATGSA-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 prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
Long-chain fatty acid
Fatty alcohol
Hydroxy fatty acid
Cyclopentanol
Cyclic alcohol
Cyclic ketone
Ketone
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Isoprostanes (LMFA03110002 )

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	3.04	ALOGPS
logP	3.59	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	4.35	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	94.83 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	98.32 m³·mol⁻¹	ChemAxon
Polarizability	41.51 Å³	ChemAxon
Number of Rings	1	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

HMDB0004686

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB023405

KNApSAcK ID

Not Available

Chemspider ID

4446333

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283212

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 8-Isoprostaglandin E1 (NP0334733)

MOL for NP0334733 (8-Isoprostaglandin E1)

3D MOL for NP0334733 (8-Isoprostaglandin E1)

3D SDF for NP0334733 (8-Isoprostaglandin E1)

3D-SDF for NP0334733 (8-Isoprostaglandin E1)

PDB for NP0334733 (8-Isoprostaglandin E1)

3D PDB for NP0334733 (8-Isoprostaglandin E1)

SMILES for NP0334733 (8-Isoprostaglandin E1)

INCHI for NP0334733 (8-Isoprostaglandin E1)

Structure for NP0334733 (8-Isoprostaglandin E1)

3D Structure for NP0334733 (8-Isoprostaglandin E1)