NP-MRD: Showing NP-Card for methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate (NP0328191)

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Record Information

Version

2.0

Created at

2022-09-12 11:26:36 UTC

Updated at

2022-09-12 11:26:36 UTC

NP-MRD ID

NP0328191

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate

Description

Methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]Heptadec-15-ene-16-carboxylate 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. Based on a literature review very few articles have been published on methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]Heptadec-15-ene-16-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122213262D          

 35 40  0  0  0  0            999 V2000
    6.5218   -0.8121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

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M  END


  Mrv1652309122213262D          

 35 40  0  0  0  0            999 V2000
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    3.0685    3.0938    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 18 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 16 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 13 33  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
  9 34  1  0  0  0  0
 34 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328191

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC(=O)C2CC1(C)C1CCC3(C)C(CCC33OC13C2O)C(C)C1OC1C(C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O6/c1-14(2)15(3)22-23(34-22)16(4)18-8-11-28-27(18,6)10-9-21-26(5)13-17(24(31)29(21,28)35-28)20(30)12-19(26)25(32)33-7/h12,14-18,21-24,31H,8-11,13H2,1-7H3

> <INCHI_KEY>
GQGRHHQOPCZNAP-UHFFFAOYSA-N

> <FORMULA>
C29H42O6

> <MOLECULAR_WEIGHT>
486.649

> <EXACT_MASS>
486.298139072

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
54.78863418045276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0^{2,11}.0^{5,9}.0^{9,11}]heptadec-15-ene-16-carboxylate

> <JCHEM_LOGP>
4.650449660333335

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.968780299513408

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.476690616520795

> <JCHEM_PKA_STRONGEST_BASIC>
-3.458236021441998

> <JCHEM_POLAR_SURFACE_AREA>
88.66000000000001

> <JCHEM_REFRACTIVITY>
130.463

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0^{2,11}.0^{5,9}.0^{9,11}]heptadec-15-ene-16-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0      12.174  -1.516   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.526  -0.119   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.992   0.018   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       9.106  -1.242   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       9.344   1.415   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.300   2.718   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.561   4.154   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.414   5.437   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       7.950   4.281   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.830   2.915   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.714   1.527   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.600  -0.008   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.063   1.659   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.232   0.328   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.692   0.323   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.900   1.668   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.040   0.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.341   1.896   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.264   0.795   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.680  -0.688   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.228   1.176   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.710   0.760   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -2.329   2.252   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.745   3.735   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.237   4.117   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.668   4.837   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.084   6.320   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.176   4.455   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.081   3.424   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.463   4.122   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.661   3.065   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       4.433   4.417   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       5.275   3.095   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.342   4.363   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.728   5.775   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   34                                                  
CONECT   10    9   11                                                       
CONECT   11   10    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14   33                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   31                                             
CONECT   17   16                                                            
CONECT   18   16   19   29                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   23                                                  
CONECT   22   21   23                                                       
CONECT   23   22   21   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   18   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   16   32   33                                             
CONECT   32   31   33                                                       
CONECT   33   32   13   31   34                                             
CONECT   34   33    9   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Value	Source
Methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0,.0,.0,]heptadec-15-ene-16-carboxylic acid	Generator

Chemical Formula

C₂₉H₄₂O₆

Average Mass

486.6490 Da

Monoisotopic Mass

486.29814 Da

IUPAC Name

methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0^{2,11}.0^{5,9}.0^{9,11}]heptadec-15-ene-16-carboxylate

Traditional Name

methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0^{2,11}.0^{5,9}.0^{9,11}]heptadec-15-ene-16-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC(=O)C2CC1(C)C1CCC3(C)C(CCC33OC13C2O)C(C)C1OC1C(C)C(C)C

InChI Identifier

InChI=1S/C29H42O6/c1-14(2)15(3)22-23(34-22)16(4)18-8-11-28-27(18,6)10-9-21-26(5)13-17(24(31)29(21,28)35-28)20(30)12-19(26)25(32)33-7/h12,14-18,21-24,31H,8-11,13H2,1-7H3

InChI Key

GQGRHHQOPCZNAP-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
Sesquiterpenoid
Cyclohexenone
Oxepane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Cyclic alcohol
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	4.65	ChemAxon
pKa (Strongest Acidic)	13.48	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	88.66 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	130.46 m³·mol⁻¹	ChemAxon
Polarizability	54.79 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

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

162983631

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate (NP0328191)

MOL for NP0328191 (methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate)

3D MOL for NP0328191 (methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate)

3D SDF for NP0328191 (methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate)

3D-SDF for NP0328191 (methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate)

PDB for NP0328191 (methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate)

3D PDB for NP0328191 (methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate)

SMILES for NP0328191 (methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate)

INCHI for NP0328191 (methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate)

Structure for NP0328191 (methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate)

3D Structure for NP0328191 (methyl 12-hydroxy-1,5-dimethyl-6-{1-[3-(3-methylbutan-2-yl)oxiran-2-yl]ethyl}-14-oxo-10-oxapentacyclo[11.3.1.0²,¹¹.0⁵,⁹.0⁹,¹¹]heptadec-15-ene-16-carboxylate)