NP-MRD: Showing NP-Card for 2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate (NP0328408)

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Record Information

Version

2.0

Created at

2022-09-12 11:51:24 UTC

Updated at

2022-09-12 11:51:25 UTC

NP-MRD ID

NP0328408

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate

Description

2-Hydroxy-2-(3-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl acetate belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. 2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate is found in Goniothalamus giganteus. 2-Hydroxy-2-(3-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    2.7219    3.9215    0.3095 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752    2.9075    0.6246 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8654    3.0238    1.5670 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051    1.7939   -0.1652 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6249    0.7765    0.0773 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3063   -0.5013    0.4193 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9674   -1.2702    1.5060 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6059   -2.4601    1.8077 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6170   -2.8855    0.9871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9796   -2.1340   -0.1118 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3273   -0.9497   -0.3923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2847    0.6146   -1.0981 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9548    1.7720   -1.4380 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3130   -0.4274   -0.8111 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1088   -0.6911   -1.9936 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -1.5587   -1.8697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6193   -2.2632   -2.8135 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8434   -1.6551   -0.5828 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4239   -0.9342    0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2775   -0.0164    0.2762 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.8109    1.2536    0.0385 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7194    3.5513    0.6071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7528    4.1477   -0.7741 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5112    4.8646    0.8548 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0405    1.1016    0.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.9771    2.1860 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3158   -3.0495    2.6764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1228   -3.8187    1.2177 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7893   -2.5102   -0.7371 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6641   -0.4142   -1.2683 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3140    0.2737   -1.9803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7006    1.5662   -2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8395   -1.3773   -0.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6952   -2.3207   -0.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9349   -1.0196    1.4141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7365    0.0006    1.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9797    1.6649    0.9261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 20 14  1  0
 11  6  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  1
 12 31  1  6
 13 32  1  0
 14 33  1  1
 18 34  1  0
 19 35  1  0
 20 36  1  1
 21 37  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
M  END


  Mrv1533004241500182D          

 21 22  0  0  0  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    0.0000   -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 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    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  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  1  0  0  0  0
  5 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328408

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC(C(O)C1OC(=O)C=CC1O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O6/c1-9(16)20-14(10-5-3-2-4-6-10)13(19)15-11(17)7-8-12(18)21-15/h2-8,11,13-15,17,19H,1H3

> <INCHI_KEY>
BWDGXQDVXMUNDT-UHFFFAOYSA-N

> <FORMULA>
C15H16O6

> <MOLECULAR_WEIGHT>
292.287

> <EXACT_MASS>
292.094688235

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.398624469610468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-2-(3-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl acetate

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
0.8709763603333331

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.831867270593698

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.884459154891712

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3889334144966607

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
72.56920000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.97e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   16                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    8   15                                                  
CONECT   15   14                                                            
CONECT   16    5   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxy-2-(3-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl acetic acid	Generator

Chemical Formula

C₁₅H₁₆O₆

Average Mass

292.2870 Da

Monoisotopic Mass

292.09469 Da

IUPAC Name

2-hydroxy-2-(3-hydroxy-6-oxo-3,6-dihydro-2H-pyran-2-yl)-1-phenylethyl acetate

Traditional Name

2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC(C(O)C1OC(=O)C=CC1O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H16O6/c1-9(16)20-14(10-5-3-2-4-6-10)13(19)15-11(17)7-8-12(18)21-15/h2-8,11,13-15,17,19H,1H3

InChI Key

BWDGXQDVXMUNDT-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

Species Name	Source	Reference
Goniothalamus giganteus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyloxycarbonyls

Direct Parent

Benzyloxycarbonyls

Alternative Parents

Substituents

Benzyloxycarbonyl
Dihydropyranone
Dicarboxylic acid or derivatives
Pyran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	0.67	ALOGPS
logP	0.87	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	12.88	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	72.57 m³·mol⁻¹	ChemAxon
Polarizability	28.4 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate (NP0328408)

MOL for NP0328408 (2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate)

3D MOL for NP0328408 (2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate)

3D SDF for NP0328408 (2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate)

3D-SDF for NP0328408 (2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate)

PDB for NP0328408 (2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate)

3D PDB for NP0328408 (2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate)

SMILES for NP0328408 (2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate)

INCHI for NP0328408 (2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate)

Structure for NP0328408 (2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate)

3D Structure for NP0328408 (2-hydroxy-2-(3-hydroxy-6-oxo-2,3-dihydropyran-2-yl)-1-phenylethyl acetate)