NP-MRD: Showing NP-Card for 8-iso-PGA1 (NP0334705)

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Record Information

Version

2.0

Created at

2024-09-10 19:36:19 UTC

Updated at

2024-09-10 19:36:19 UTC

NP-MRD ID

NP0334705

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-iso-PGA1

Description

8-Iso-PGA1 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-iso-pga1 is considered to be an eicosanoid lipid molecule. The PGs and TXs are collectively identified as prostanoids. 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. 8-Iso-PGA1 is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All mammalian cells except erythrocytes synthesize eicosanoids. Thus, it may be possible that the isoprostanes are playing somewhat of a causal role in those disease states. These accumulate to substantial levels in many clinical conditions characterized in part by accumulation of free radicals and reactive oxygen species, including asthma, hypertension and ischemia reperfusion injury.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231219262D          

 24 24  0  0  1  0            999 V2000
   18.3598  -10.2635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.2574   -5.8515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.9990   -9.9998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4405   -8.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5899   -8.8115    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   19.2574   -8.3265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.8053   -8.5565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1922   -9.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8449   -9.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9247   -8.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4075   -8.8537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2574   -7.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6699   -9.5961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7944   -9.4057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9717   -7.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9717   -6.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.0099   -9.1507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6863   -5.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6863   -5.0265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4008   -4.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3968   -9.7027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4008   -3.7891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1152   -3.3765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6121   -9.4477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  9  2  0  0  0  0
 16  2  1  1  0  0  0
  3 24  1  0  0  0  0
  4 24  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  1  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  6 12  1  1  0  0  0
  7  8  1  0  0  0  0
  8 11  1  0  0  0  0
  9 13  1  0  0  0  0
 10 13  2  0  0  0  0
 11 14  1  0  0  0  0
 12 15  2  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 16 18  1  0  0  0  0
 17 21  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  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
M  END
> <DATABASE_ID>
NP0334705

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H32O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18-/m0/s1

> <INCHI_KEY>
BGKHCLZFGPIKKU-DRSVPBQLSA-N

> <FORMULA>
C20H32O4

> <MOLECULAR_WEIGHT>
336.4657

> <EXACT_MASS>
336.230059512

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
39.81320961212484

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
4.737872620333333

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
17.74675363107826

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.45154130592671

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5972323838202795

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
97.9733

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-iso-PGA1

> <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      34.272 -19.158   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      35.947 -10.923   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      24.265 -18.666   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      25.089 -16.129   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      34.701 -16.448   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.947 -15.543   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      33.237 -15.972   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      32.092 -17.003   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      35.177 -17.913   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.193 -16.448   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      30.627 -16.527   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      35.947 -14.003   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      36.717 -17.913   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      29.483 -17.557   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      37.281 -13.233   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      37.281 -11.693   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.018 -17.081   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      38.614 -10.923   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      38.614  -9.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      39.948  -8.613   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      26.874 -18.112   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      39.948  -7.073   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      41.282  -6.303   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      25.409 -17.636   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   16                                                            
CONECT    3   24                                                            
CONECT    4   24                                                            
CONECT    5    6    7    9                                                  
CONECT    6    5   10   12                                                  
CONECT    7    5    8                                                       
CONECT    8    7   11                                                       
CONECT    9    1    5   13                                                  
CONECT   10    6   13                                                       
CONECT   11    8   14                                                       
CONECT   12    6   15                                                       
CONECT   13    9   10                                                       
CONECT   14   11   17                                                       
CONECT   15   12   16                                                       
CONECT   16    2   15   18                                                  
CONECT   17   14   21                                                       
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   22                                                       
CONECT   21   17   24                                                       
CONECT   22   20   23                                                       
CONECT   23   22                                                            
CONECT   24    3    4   21                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   48    0
END

View in JSmol

Synonyms

Value	Source
(8S,12S)-15S-Hydroxy-9-oxoprosta-10Z,13E-dien-1-Oate	HMDB
(8S,12S)-15S-Hydroxy-9-oxoprosta-10Z,13E-dien-1-Oic acid	HMDB
8-Isoprostaglandin a1 (8-iso pga1)	HMDB
9-oxo-15S-Hydroxy-10Z,13E-prostadienoate	HMDB
9-oxo-15S-Hydroxy-10Z,13E-prostadienoic acid	HMDB
9-oxo-15S-Hydroxy-10Z,13E-prostadienoic acid-cyclo[8S,12S]	HMDB

Chemical Formula

C₂₀H₃₂O₄

Average Mass

336.4657 Da

Monoisotopic Mass

336.23006 Da

IUPAC Name

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

Traditional Name

8-iso-PGA1

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H32O4/c1-2-3-6-9-17(21)14-12-16-13-15-19(22)18(16)10-7-4-5-8-11-20(23)24/h12-18,21H,2-11H2,1H3,(H,23,24)/b14-12+/t16-,17-,18-/m0/s1

InChI Key

BGKHCLZFGPIKKU-DRSVPBQLSA-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
Ketone
Cyclic ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Isoprostanes (LMFA03110008 )

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	4.21	ALOGPS
logP	4.74	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.45	ChemAxon
pKa (Strongest Basic)	-1.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	97.97 m³·mol⁻¹	ChemAxon
Polarizability	39.81 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

HMDB0002236

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB022923

KNApSAcK ID

Not Available

Chemspider ID

4975993

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6473771

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 8-iso-PGA1 (NP0334705)

MOL for NP0334705 (8-iso-PGA1)

3D MOL for NP0334705 (8-iso-PGA1)

3D SDF for NP0334705 (8-iso-PGA1)

3D-SDF for NP0334705 (8-iso-PGA1)

PDB for NP0334705 (8-iso-PGA1)

3D PDB for NP0334705 (8-iso-PGA1)

SMILES for NP0334705 (8-iso-PGA1)

INCHI for NP0334705 (8-iso-PGA1)

Structure for NP0334705 (8-iso-PGA1)

3D Structure for NP0334705 (8-iso-PGA1)