NP-MRD: Showing NP-Card for 2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone (NP0146254)

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Record Information

Version

2.0

Created at

2022-09-02 01:36:53 UTC

Updated at

2022-09-02 01:36:53 UTC

NP-MRD ID

NP0146254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone

Description

Diospongin A belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain. 2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone is found in Dioscorea spongiosa. 2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone was first documented in 2009 (PMID: 19824665). Based on a literature review a small amount of articles have been published on Diospongin A (PMID: 31595914) (PMID: 28451195) (PMID: 25867851) (PMID: 23168684).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    1.7788   -0.1119   -1.4873 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2088   -0.0358   -0.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3653   -0.5099    0.8519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0817   -1.0145    0.2964 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8747   -1.5258    1.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8915   -2.3896    0.6157 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3236   -3.6855    0.5808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9884   -1.9349   -0.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7310   -0.4814   -1.0251 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8386    0.4085   -0.6177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0724    0.0006   -0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0822    0.8640    0.1601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8522    2.2162    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6091    2.6602   -0.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6094    1.7829   -0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5512   -0.0482   -0.4533 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5289    0.5171   -0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2627    0.9356   -1.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5251    1.4672   -1.0020 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0134    1.5597    0.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2908    1.1424    1.3866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176    0.6096    1.1802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2078    0.4041    1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9237   -1.2685    1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3344   -1.8973   -0.3623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4228   -0.7260    1.8675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2889   -2.1506    2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8595   -2.4139    1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7164   -3.7863   -0.1818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2688   -2.4866   -1.4782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9910   -2.1828   -1.2469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905   -0.3530   -2.1395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2974   -1.0448   -0.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0374    0.4806    0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6195    2.9350    0.4216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4604    3.7326   -0.2795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6701    2.1956   -0.9451 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8556    0.8527   -2.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0824    1.7901   -1.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0067    1.9797    0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6798    1.2177    2.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4835    0.2953    2.0647 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  4 16  1  0
 16  9  1  0
  9  8  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
  8  6  1  0
 15 10  1  0
 22 17  1  0
  7 29  1  0
  6 28  1  1
  5 26  1  0
  5 27  1  0
  4 25  1  6
  3 23  1  0
  3 24  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
  9 32  1  6
  8 30  1  0
  8 31  1  0
 11 33  1  0
 12 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
M  END


  Mrv1652309022203362D          

 22 24  0  0  1  0            999 V2000
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 10 15  1  0  0  0  0
  9 16  1  0  0  0  0
  4 16  1  0  0  0  0
  2 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1C[C@H](CC(=O)C2=CC=CC=C2)O[C@@H](C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H20O3/c20-16-11-17(13-18(21)14-7-3-1-4-8-14)22-19(12-16)15-9-5-2-6-10-15/h1-10,16-17,19-20H,11-13H2/t16-,17+,19-/m0/s1

> <INCHI_KEY>
HQTSVUPKAYCDEB-SCTDSRPQSA-N

> <FORMULA>
C19H20O3

> <MOLECULAR_WEIGHT>
296.366

> <EXACT_MASS>
296.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
32.05492574883918

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(2R,4S,6S)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethan-1-one

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
2.7558513786666667

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.309359204432674

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.593283732577042

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7636762654407994

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
85.29090000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.11e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(2R,4S,6S)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   10                                                       
CONECT   16    9    4                                                       
CONECT   17    2   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₀O₃

Average Mass

296.3660 Da

Monoisotopic Mass

296.14124 Da

IUPAC Name

2-[(2R,4S,6S)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethan-1-one

Traditional Name

2-[(2R,4S,6S)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone

CAS Registry Number

Not Available

SMILES

O[C@H]1C[C@H](CC(=O)C2=CC=CC=C2)O[C@@H](C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C19H20O3/c20-16-11-17(13-18(21)14-7-3-1-4-8-14)22-19(12-16)15-9-5-2-6-10-15/h1-10,16-17,19-20H,11-13H2/t16-,17+,19-/m0/s1

InChI Key

HQTSVUPKAYCDEB-SCTDSRPQSA-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

Species Name	Source	Reference
Dioscorea spongiosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as linear diarylheptanoids. These are diarylheptanoids with an open heptane chain. The two aromatic rings are linked only by the heptane chain.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Diarylheptanoids

Sub Class

Linear diarylheptanoids

Direct Parent

Linear diarylheptanoids

Alternative Parents

Substituents

Linear 1,7-diphenylheptane skeleton
Alkyl-phenylketone
Phenylketone
Benzoyl
Aryl alkyl ketone
Aryl ketone
Monocyclic benzene moiety
Oxane
Benzenoid
Ketone
Secondary alcohol
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	2.8	ALOGPS
logP	2.76	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.59	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	85.29 m³·mol⁻¹	ChemAxon
Polarizability	32.05 Å³	ChemAxon
Number of Rings	3	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9827037

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11652299

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bharath Y, Choudhury UM, Sadhana N, Mohapatra DK: The Mukaiyama type aldol reaction for the synthesis of trans-2,6-disubstituted tetrahydropyrans: synthesis of diospongin A and B. Org Biomol Chem. 2019 Oct 23;17(41):9169-9181. doi: 10.1039/c9ob01549c. [PubMed:31595914 ]
Ermanis K, Hsiao YT, Kaya U, Jeuken A, Clarke PA: The stereodivergent formation of 2,6-cis and 2,6-trans-tetrahydropyrans: experimental and computational investigation of the mechanism of a thioester oxy-Michael cyclization. Chem Sci. 2017 Jan 1;8(1):482-490. doi: 10.1039/c6sc03478k. Epub 2016 Aug 30. [PubMed:28451195 ]
Merad J, Borkar P, Bouyon Yenda T, Roux C, Pons JM, Parrain JL, Chuzel O, Bressy C: Highly Enantioselective Acylation of Acyclic Meso 1,3-Diols through Synergistic Isothiourea-Catalyzed Desymmetrization/Chiroablative Kinetic Resolution. Org Lett. 2015 May 1;17(9):2118-21. doi: 10.1021/acs.orglett.5b00707. Epub 2015 Apr 13. [PubMed:25867851 ]
Yao H, Ren J, Tong R: A short and flexible route to tetrahydropyran-4-ones via conjugated nitrile oxides cycloaddition and oxa-Michael cyclization: a concise diastereoselective total synthesis of (+/-)-diospongin A. Chem Commun (Camb). 2013 Jan 7;49(2):193-5. doi: 10.1039/c2cc37772a. Epub 2012 Nov 21. [PubMed:23168684 ]
Lee K, Kim H, Hong J: A facile and efficient synthesis of 4-hydroxy-2,6-cis-tetrahydropyrans via tandem cross-metathesis/thermal S(N)2' reaction: protecting-group-free synthesis of (+/-)-diospongin A. Org Lett. 2009 Nov 19;11(22):5202-5. doi: 10.1021/ol902125d. [PubMed:19824665 ]
LOTUS database [Link]

Showing NP-Card for 2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone (NP0146254)

MOL for NP0146254 (2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone)

3D MOL for NP0146254 (2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone)

3D SDF for NP0146254 (2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone)

3D-SDF for NP0146254 (2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone)

PDB for NP0146254 (2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone)

3D PDB for NP0146254 (2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone)

SMILES for NP0146254 (2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone)

INCHI for NP0146254 (2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone)

Structure for NP0146254 (2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone)

3D Structure for NP0146254 (2-[(2r,4s,6s)-4-hydroxy-6-phenyloxan-2-yl]-1-phenylethanone)