NP-MRD: Showing NP-Card for (5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate (NP0339981)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-12 00:39:18 UTC

Updated at

2024-09-12 00:39:18 UTC

NP-MRD ID

NP0339981

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate

Description

(5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate, also known as 15-dehydro-prostaglandin E2 anion, 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 (5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533007131514022D          

 32 32  0  0  1  0            999 V2000
   -0.5662    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1483    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6332    8.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4178    8.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4617    7.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5894    9.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748    6.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9763    9.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0428    4.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9033    5.9808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1496    5.6452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4553    5.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2358    4.8247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1478   10.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    6.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2758    5.4539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    4.2727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5347   11.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9324   10.8226    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.0201    8.6988    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6771    7.0848    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206    4.8202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351    6.8827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7001    6.1943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1928    6.4691    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4656    5.1204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 13 12  2  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  1  0  0  0
 17 13  1  6  0  0  0
 17 16  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 14  1  0  0  0  0
 19 17  1  0  0  0  0
 20 11  1  0  0  0  0
 21 15  2  0  0  0  0
 22 18  2  0  0  0  0
 19 23  1  1  0  0  0
 24 20  2  0  0  0  0
 25 20  1  0  0  0  0
 26  4  1  0  0  0  0
 27  7  1  0  0  0  0
 28 12  1  0  0  0  0
 29 13  1  0  0  0  0
 16 30  1  6  0  0  0
 17 31  1  1  0  0  0
 19 32  1  6  0  0  0
M  CHG  1  25  -1
M  END


  Mrv1533007131514022D          

 32 32  0  0  1  0            999 V2000
   -0.5662    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1483    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8628    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6332    8.1467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4178    8.4017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5772    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4617    7.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5894    9.2087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2917    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0748    6.7877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9763    9.7607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206    5.6452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0428    4.6532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    6.0577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9033    5.9808    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.1496    5.6452    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.4553    5.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2358    4.8247    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1478   10.5677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0062    6.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2758    5.4539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6227    4.2727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5347   11.1197    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9324   10.8226    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    5.0201    8.6988    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6771    7.0848    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7206    4.8202    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4351    6.8827    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7001    6.1943    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1928    6.4691    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4656    5.1204    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  1  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  8  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 13 12  2  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  1  0  0  0
 17 13  1  6  0  0  0
 17 16  1  0  0  0  0
 18 14  1  0  0  0  0
 18 16  1  0  0  0  0
 19 14  1  0  0  0  0
 19 17  1  0  0  0  0
 20 11  1  0  0  0  0
 21 15  2  0  0  0  0
 22 18  2  0  0  0  0
 19 23  1  1  0  0  0
 24 20  2  0  0  0  0
 25 20  1  0  0  0  0
 26  4  1  0  0  0  0
 27  7  1  0  0  0  0
 28 12  1  0  0  0  0
 29 13  1  0  0  0  0
 16 30  1  6  0  0  0
 17 31  1  1  0  0  0
 19 32  1  6  0  0  0
M  CHG  1  25  -1
M  END
> <DATABASE_ID>
NP0339981

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30O5/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/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/p-1/b7-4-,13-12+/t16-,17-,19-/m1/s1

> <INCHI_KEY>
YRTJDWROBKPZNV-KMXMBPPJSA-M

> <FORMULA>
C20H29O5

> <MOLECULAR_WEIGHT>
349.448

> <EXACT_MASS>
349.202047614

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
38.553252390510806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoate

> <ALOGPS_LOGP>
3.10

> <JCHEM_LOGP>
3.636608624999999

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.678218203398721

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.303359015207499

> <JCHEM_PKA_STRONGEST_BASIC>
-2.93524020776586

> <JCHEM_POLAR_SURFACE_AREA>
94.5

> <JCHEM_REFRACTIVITY>
109.37479999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-dehydro-prostaglandin E2

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0      -1.057  10.538   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.277  11.308   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.610  10.538   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.515  15.207   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.980  15.683   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.944  11.308   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.195  13.701   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.300  17.189   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.278  10.538   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.340  12.670   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.156  18.220   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.945  10.538   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.279  11.308   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.280   8.686   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.612  11.308   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      11.019  11.164   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.613  10.538   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.050  10.020   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.774   9.006   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.476  19.726   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       5.612  12.848   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      13.581  10.181   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       8.629   7.976   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.331  20.757   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      12.941  20.202   0.000  0.00  0.00           O-1
HETATM   26  H   UNK     0       9.371  16.238   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       8.731  13.225   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       6.945   8.998   0.000  0.00  0.00           H+0
HETATM   29  H   UNK     0       8.279  12.848   0.000  0.00  0.00           H+0
HETATM   30  H   UNK     0      12.507  11.563   0.000  0.00  0.00           H+0
HETATM   31  H   UNK     0       9.693  12.076   0.000  0.00  0.00           H+0
HETATM   32  H   UNK     0       8.336   9.558   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    6                                                       
CONECT    4    5    7   26                                                  
CONECT    5    4    8                                                       
CONECT    6    3    9                                                       
CONECT    7    4   10   27                                                  
CONECT    8    5   11                                                       
CONECT    9    6   15                                                       
CONECT   10    7   16                                                       
CONECT   11    8   20                                                       
CONECT   12   13   15   28                                                  
CONECT   13   12   17   29                                                  
CONECT   14   18   19                                                       
CONECT   15    9   12   21                                                  
CONECT   16   10   17   18   30                                             
CONECT   17   13   16   19   31                                             
CONECT   18   14   16   22                                                  
CONECT   19   14   17   23   32                                             
CONECT   20   11   24   25                                                  
CONECT   21   15                                                            
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   20                                                            
CONECT   25   20                                                            
CONECT   26    4                                                            
CONECT   27    7                                                            
CONECT   28   12                                                            
CONECT   29   13                                                            
CONECT   30   16                                                            
CONECT   31   17                                                            
CONECT   32   19                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   64    0
END

View in JSmol

Synonyms

Value	Source
15-Dehydro-prostaglandin e2 anion	ChEBI
15-oxo-Prostaglandin e2	ChEBI
(5Z)-(15S)-11-Α-hydroxy-9,15-dioxoprosta-13-enoic acid	Generator
9,15-dioxo-11-Hydroxyprosta-5,13-dienoic acid	MeSH
15-keto-PGE2	MeSH
15-keto-Prostaglandin e2	MeSH
15-Ketoprostaglandin e2	MeSH
15-oxo-PGE2	MeSH
15-Ketoprostaglandin e2, (11alpha)-isomer	MeSH

Chemical Formula

C₂₀H₂₉O₅

Average Mass

349.4480 Da

Monoisotopic Mass

349.20205 Da

IUPAC Name

(5Z)-7-[(1R,2R,3R)-3-hydroxy-5-oxo-2-[(1E)-3-oxooct-1-en-1-yl]cyclopentyl]hept-5-enoate

Traditional Name

15-dehydro-prostaglandin E2

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H30O5/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/h4,7,12-13,16-17,19,23H,2-3,5-6,8-11,14H2,1H3,(H,24,25)/p-1/b7-4-,13-12+/t16-,17-,19-/m1/s1

InChI Key

YRTJDWROBKPZNV-KMXMBPPJSA-M

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
Hydroxy fatty acid
Cyclopentanol
Fatty acid
Unsaturated fatty acid
Acryloyl-group
Cyclic alcohol
Alpha,beta-unsaturated ketone
Enone
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic anion
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

prostaglandin carboxylic acid anion (CHEBI:57400 )

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	3.1	ALOGPS
logP	3.64	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	94.5 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	109.37 m³·mol⁻¹	ChemAxon
Polarizability	38.55 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB030125

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

25244714

PDB ID

Not Available

ChEBI ID

57400

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate (NP0339981)

MOL for NP0339981 ((5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate)

3D MOL for NP0339981 ((5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate)

3D SDF for NP0339981 ((5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate)

3D-SDF for NP0339981 ((5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate)

PDB for NP0339981 ((5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate)

3D PDB for NP0339981 ((5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate)

SMILES for NP0339981 ((5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate)

INCHI for NP0339981 ((5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate)

Structure for NP0339981 ((5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate)

3D Structure for NP0339981 ((5Z)-(15S)-11-α-hydroxy-9,15-dioxoprosta-13-enoate)