NP-MRD: Showing NP-Card for Prostaglandin G1 (NP0339162)

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Record Information

Version

2.0

Created at

2024-09-11 19:59:21 UTC

Updated at

2024-09-11 19:59:22 UTC

NP-MRD ID

NP0339162

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Prostaglandin G1

Description

Prostaglandin G1, also known as 9S-hpete or PGG(,1), 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. Prostaglandins are eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs) and lipoxins (LXs). Prostaglandin G1 is an extremely weak basic (essentially neutral) compound (based on its pKa). The PGs and TXs are collectively identified as prostanoids. All mammalian cells except erythrocytes synthesize eicosanoids. All eicosanoids function locally at the site of synthesis, through receptor-mediated G-protein linked signalling pathways. 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. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208152D          

 26 27  0  0  1  0            999 V2000
   13.8821  -16.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8821  -16.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1677  -15.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1677  -14.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4532  -14.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4532  -13.6956    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1677  -13.2831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1677  -12.4580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7387  -13.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7387  -12.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0243  -12.0455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3098  -12.4580    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8335  -11.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3098  -10.8080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5953  -11.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5953  -12.0455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0243  -11.2205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7387  -10.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4532  -11.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1677  -10.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8821  -11.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5966  -10.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3111  -11.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0256  -10.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7401  -11.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0256   -9.9830    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 13  1  6  0  0  0
 12 16  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  1  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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  END


  Mrv0541 02251208152D          

 26 27  0  0  1  0            999 V2000
   13.8821  -16.9956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8821  -16.1706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1677  -15.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1677  -14.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4532  -14.5206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4532  -13.6956    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.1677  -13.2831    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1677  -12.4580    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7387  -13.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7387  -12.4580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0243  -12.0455    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.3098  -12.4580    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    9.8335  -11.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3098  -10.8080    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.5953  -11.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5953  -12.0455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0243  -11.2205    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7387  -10.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4532  -11.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1677  -10.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8821  -11.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5966  -10.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3111  -11.2205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0256  -10.8080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7401  -11.2205    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0256   -9.9830    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
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  9  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  2  0  0  0  0
 11 10  1  6  0  0  0
 11 12  1  0  0  0  0
 11 17  1  0  0  0  0
 12 13  1  6  0  0  0
 12 16  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  1  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
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339162

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCC[C@H](OO)\C=C\[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h12-13,15-19,23H,2-11,14H2,1H3,(H,21,22)/b13-12+/t15-,16-,17-,18+,19-/m0/s1

> <INCHI_KEY>
QXCRWNZYEVOQMB-NDWDMBLISA-N

> <FORMULA>
C20H34O6

> <MOLECULAR_WEIGHT>
370.4804

> <EXACT_MASS>
370.23553882

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
42.054083282630515

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-[(1S,4R,5S,6S)-6-[(1E,3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid

> <ALOGPS_LOGP>
4.32

> <JCHEM_LOGP>
4.768184619999999

> <ALOGPS_LOGS>
-4.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.71241761760145

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.405126520074798

> <JCHEM_PKA_STRONGEST_BASIC>
-4.236788543423214

> <JCHEM_POLAR_SURFACE_AREA>
85.22

> <JCHEM_REFRACTIVITY>
98.2755

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-[(1S,4R,5S,6S)-6-[(1E,3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid

> <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      25.913 -31.725   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      25.913 -30.185   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      24.580 -29.415   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      24.580 -27.875   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      23.246 -27.105   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.246 -25.565   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      24.580 -24.795   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      24.580 -23.255   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      21.912 -24.795   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.912 -23.255   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.579 -22.485   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.245 -23.255   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.356 -21.715   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.245 -20.175   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      17.911 -20.945   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      17.911 -22.485   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      20.579 -20.945   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.912 -20.175   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.246 -20.945   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.580 -20.175   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.913 -20.945   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.247 -20.175   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      28.581 -20.945   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      29.914 -20.175   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      31.248 -20.945   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      29.914 -18.635   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   16                                                       
CONECT   16   12   15                                                       
CONECT   17   11   14   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

View in JSmol

Synonyms

Value	Source
(9S)-Hydroperoxy-(5Z,7E,11Z,14Z)-eicosatetraenoate	HMDB
(9S)-Hydroperoxy-(5Z,7E,11Z,14Z)-eicosatetraenoic acid	HMDB
9alpha, 11alpha-Epidioxy-15(S)-hydroperoxy-13-trans-prostenoate	HMDB
9alpha, 11alpha-Epidioxy-15(S)-hydroperoxy-13-trans-prostenoic acid	HMDB
9S-HPETE	HMDB
PGG(,1)	HMDB
7-[(1S,4R,5S,6S)-6-[(1E,3S)-3-Hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoate	Generator

Chemical Formula

C₂₀H₃₄O₆

Average Mass

370.4804 Da

Monoisotopic Mass

370.23554 Da

IUPAC Name

7-[(1S,4R,5S,6S)-6-[(1E,3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid

Traditional Name

7-[(1S,4R,5S,6S)-6-[(1E,3S)-3-hydroperoxyoct-1-en-1-yl]-2,3-dioxabicyclo[2.2.1]heptan-5-yl]heptanoic acid

CAS Registry Number

Not Available

SMILES

CCCCC[C@H](OO)\C=C\[C@@H]1[C@@H]2C[C@@H](OO2)[C@H]1CCCCCCC(O)=O

InChI Identifier

InChI=1S/C20H34O6/c1-2-3-6-9-15(24-23)12-13-17-16(18-14-19(17)26-25-18)10-7-4-5-8-11-20(21)22/h12-13,15-19,23H,2-11,14H2,1H3,(H,21,22)/b13-12+/t15-,16-,17-,18+,19-/m0/s1

InChI Key

QXCRWNZYEVOQMB-NDWDMBLISA-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
Hydroperoxy fatty acid
Heterocyclic fatty acid
Ortho-dioxane
Allylic hydroperoxide
Ortho-dioxolane
Dialkyl peroxide
Hydroperoxide
Alkyl hydroperoxide
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Peroxol
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.32	ALOGPS
logP	4.77	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	4.41	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	98.28 m³·mol⁻¹	ChemAxon
Polarizability	42.05 Å³	ChemAxon
Number of Rings	2	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

HMDB0013039

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029264

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

53481591

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Prostaglandin G1 (NP0339162)

MOL for NP0339162 (Prostaglandin G1)

3D MOL for NP0339162 (Prostaglandin G1)

3D SDF for NP0339162 (Prostaglandin G1)

3D-SDF for NP0339162 (Prostaglandin G1)

PDB for NP0339162 (Prostaglandin G1)

3D PDB for NP0339162 (Prostaglandin G1)

SMILES for NP0339162 (Prostaglandin G1)

INCHI for NP0339162 (Prostaglandin G1)

Structure for NP0339162 (Prostaglandin G1)

3D Structure for NP0339162 (Prostaglandin G1)