NP-MRD: Showing NP-Card for 1-O-Deacetyl-2alpha-hydroxykhayanolide E (NP0137808)

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Record Information

Version

2.0

Created at

2022-05-31 16:34:29 UTC

Updated at

2022-05-31 16:34:29 UTC

NP-MRD ID

NP0137808

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1-O-Deacetyl-2alpha-hydroxykhayanolide E

Description

1-O-Deacetyl-2alpha-hydroxykhayanolide E 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 1-O-Deacetyl-2alpha-hydroxykhayanolide E.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652305312218342D          

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M  END

     RDKit          3D

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M  END


  Mrv1652305312218342D          

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    2.0378   -2.2304    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855   -1.2891    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2885   -2.0588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9097   -0.8152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.4387   -1.4483    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6971    0.8315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5477    1.6428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  6  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  2  1  1  0  0  0
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  1  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 27 31  1  0  0  0  0
 25 32  1  0  0  0  0
 20 32  1  0  0  0  0
 32 33  1  1  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  1  0  0  0
 36 38  1  0  0  0  0
  8 38  1  0  0  0  0
 13 38  1  0  0  0  0
 38 39  1  1  0  0  0
 36 40  1  0  0  0  0
 15 40  1  0  0  0  0
 20 40  1  0  0  0  0
 40 41  1  1  0  0  0
 17 42  1  0  0  0  0
 10 42  1  0  0  0  0
 42 43  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0137808

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@](O)(C(=O)OC)[C@@]1([H])[C@@]2(C)C[C@]3(O)[C@]4([H])[C@@](O)(O[C@]56CC(=O)O[C@@]([H])(C7=COC=C7)[C@]5(C)CC[C@]([H])([C@]13C)[C@]46O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O11/c1-21-11-24(32)19-26(33)13(23(24,3)16(21)15(29)18(30)35-4)5-7-22(2)17(12-6-8-36-10-12)37-14(28)9-25(22,26)38-27(19,34)20(21)31/h6,8,10,13,15-17,19,29,32-34H,5,7,9,11H2,1-4H3/t13-,15+,16+,17+,19+,21-,22+,23-,24+,25-,26+,27-/m1/s1

> <INCHI_KEY>
ZDUBHZUNBSRUQC-UVQHVSCZSA-N

> <FORMULA>
C27H32O11

> <MOLECULAR_WEIGHT>
532.542

> <EXACT_MASS>
532.19446185

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.87690270744529

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2S)-2-[(1S,2S,3S,4R,7S,8R,12R,14R,16R,17R,18S)-8-(furan-3-yl)-1,3,14-trihydroxy-7,16,18-trimethyl-10,15-dioxo-9,13-dioxahexacyclo[14.2.1.0^{2,14}.0^{3,12}.0^{4,18}.0^{7,12}]nonadecan-17-yl]-2-hydroxyacetate

> <JCHEM_LOGP>
0.281159730333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.328609735810542

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.935343732999184

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8771568226788493

> <JCHEM_POLAR_SURFACE_AREA>
172.96

> <JCHEM_REFRACTIVITY>
123.4403

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(S)-(methyl [(1S,2S,3S,4R,7S,8R,12R,14R,16R,17R,18S)-8-(furan-3-yl)-1,3,14-trihydroxy-7,16,18-trimethyl-10,15-dioxo-9,13-dioxahexacyclo[14.2.1.0^{2,14}.0^{3,12}.0^{4,18}.0^{7,12}]nonadecan-17-yl](hydroxy)acetate)

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 31-MAY-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-MAY-22         0                                  
HETATM    1  H   UNK     0      -1.338  -2.947   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0       0.055  -2.291   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.073  -3.825   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.210  -1.413   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.083   0.122   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -2.603  -2.070   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.869  -1.192   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.448  -1.634   0.000  0.00  0.00           C+0
HETATM    9  H   UNK     0       1.423  -3.174   0.000  0.00  0.00           H+0
HETATM   10  C   UNK     0       1.896   0.395   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.563   1.167   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.399  -0.558   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.103  -1.062   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.992   0.474   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.427  -0.453   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       5.907  -0.026   0.000  0.00  0.00           H+0
HETATM   17  C   UNK     0       4.701   0.951   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.121   2.432   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.341   0.653   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.897  -0.952   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.933   0.290   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.473   0.250   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.294   1.553   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      10.173  -1.126   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.347  -2.430   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      10.886  -2.497   0.000  0.00  0.00           H+0
HETATM   27  C   UNK     0      10.056  -3.797   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.578  -4.028   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.829  -5.548   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      10.462  -6.256   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.366  -5.174   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       7.777  -2.351   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       8.619  -3.640   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       7.211  -3.839   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.670  -4.045   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.616  -2.855   0.000  0.00  0.00           C+0
HETATM   37  H   UNK     0       3.804  -4.163   0.000  0.00  0.00           H+0
HETATM   38  C   UNK     0       2.960  -2.406   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       2.405  -3.843   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       5.432  -1.522   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.419  -2.703   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       3.168   1.552   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       2.889   3.067   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    8                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6                                                            
CONECT    8    2    9   10   38                                             
CONECT    9    8                                                            
CONECT   10    8   11   12   42                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15   38                                             
CONECT   14   13                                                            
CONECT   15   13   16   17   40                                             
CONECT   16   15                                                            
CONECT   17   15   18   19   42                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   32   40                                             
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27   32                                             
CONECT   26   25                                                            
CONECT   27   25   28   31                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   27                                                       
CONECT   32   25   20   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37   38   40                                             
CONECT   37   36                                                            
CONECT   38   36    8   13   39                                             
CONECT   39   38                                                            
CONECT   40   36   15   20   41                                             
CONECT   41   40                                                            
CONECT   42   17   10   43                                                  
CONECT   43   42                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   98    0
END

View in JSmol

Synonyms

Value	Source
1-O-Deacetyl-2a-hydroxykhayanolide e	Generator
1-O-Deacetyl-2α-hydroxykhayanolide e	Generator

Chemical Formula

C₂₇H₃₂O₁₁

Average Mass

532.5420 Da

Monoisotopic Mass

532.19446 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

1189801-51-1

SMILES

[H][C@@](O)(C(=O)OC)[C@@]1([H])[C@@]2(C)C[C@]3(O)[C@]4([H])[C@@](O)(O[C@]56CC(=O)O[C@@]([H])(C7=COC=C7)[C@]5(C)CC[C@]([H])([C@]13C)[C@]46O)C2=O

InChI Identifier

InChI=1S/C27H32O11/c1-21-11-24(32)19-26(33)13(23(24,3)16(21)15(29)18(30)35-4)5-7-22(2)17(12-6-8-36-10-12)37-14(28)9-25(22,26)38-27(19,34)20(21)31/h6,8,10,13,15-17,19,29,32-34H,5,7,9,11H2,1-4H3/t13-,15+,16+,17+,19+,21-,22+,23-,24+,25-,26+,27-/m1/s1

InChI Key

ZDUBHZUNBSRUQC-UVQHVSCZSA-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
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Monosaccharide
Oxane
Cyclic alcohol
Furan
Heteroaromatic compound
Tertiary alcohol
Tetrahydrofuran
Methyl ester
Lactone
Ketone
Hemiacetal
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00048259

Chemspider ID

34966912

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91895445

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 1-O-Deacetyl-2alpha-hydroxykhayanolide E (NP0137808)

MOL for NP0137808 (1-O-Deacetyl-2alpha-hydroxykhayanolide E)

3D MOL for NP0137808 (1-O-Deacetyl-2alpha-hydroxykhayanolide E)

3D SDF for NP0137808 (1-O-Deacetyl-2alpha-hydroxykhayanolide E)

3D-SDF for NP0137808 (1-O-Deacetyl-2alpha-hydroxykhayanolide E)

PDB for NP0137808 (1-O-Deacetyl-2alpha-hydroxykhayanolide E)

3D PDB for NP0137808 (1-O-Deacetyl-2alpha-hydroxykhayanolide E)

SMILES for NP0137808 (1-O-Deacetyl-2alpha-hydroxykhayanolide E)

INCHI for NP0137808 (1-O-Deacetyl-2alpha-hydroxykhayanolide E)

Structure for NP0137808 (1-O-Deacetyl-2alpha-hydroxykhayanolide E)

3D Structure for NP0137808 (1-O-Deacetyl-2alpha-hydroxykhayanolide E)