NP-MRD: Showing NP-Card for 2-hydroxy-2-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate (NP0195987)

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Record Information

Version

2.0

Created at

2022-09-04 13:57:49 UTC

Updated at

2022-09-04 13:57:49 UTC

NP-MRD ID

NP0195987

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Goniodiol 8-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-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate is found in Goniothalamus amuyon. Based on a literature review very few articles have been published on Goniodiol 8-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
    0.0256    3.8816   -0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5987    2.8898    0.2454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2746    3.2210    1.2484 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3722    1.5630    0.0062 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8787    0.5234    0.8605 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7741   -0.3863    0.1169 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6765    0.1126   -0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372   -0.7070   -1.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5074   -2.0728   -1.3075 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6095   -2.5824   -0.3952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7476   -1.7475    0.3137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3591   -0.1654    1.3983 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1340    0.7611    2.1349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1999   -0.7528    0.3032 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4159   -1.4303    0.9146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5046   -1.6374   -0.0257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6345   -0.9201   -1.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6707    0.1246   -1.4139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8037    0.8145   -2.4695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6288    0.3353   -0.5304 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3547    3.5564   -1.7233 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3819    4.9163   -0.4709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0812    3.8175   -0.7086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4367    1.0438    1.6690 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7170    1.1790   -0.9705 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2524   -0.3315   -2.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1843   -2.7399   -1.8628 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5920   -3.6656   -0.2424 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0729   -2.2289    1.0189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0291   -0.9307    2.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776    1.6345    1.6647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7044   -1.4652   -0.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7896   -0.7162    1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1554   -2.3882    1.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2385   -2.4134    0.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4668   -1.0930   -1.8135 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
 17 18  1  0
 18 19  2  0
 18 20  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 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  1
 12 30  1  1
 13 31  1  0
 14 32  1  6
 15 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
M  END


  Mrv1652309042215572D          

 20 21  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    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
    0.0000   -0.8250    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
    0.7145    0.4125    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
    1.4289   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  1  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
    2.8579   -0.8250    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
    3.5724   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   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
  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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
  5 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 12  1  1  0  0  0
 14 15  1  0  0  0  0
 15 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
 18 20  1  0  0  0  0
 14 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0195987

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC(C(O)[C@H]1CC=CC(=O)O1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c1-10(16)19-15(11-6-3-2-4-7-11)14(18)12-8-5-9-13(17)20-12/h2-7,9,12,14-15,18H,8H2,1H3/t12-,14?,15?/m1/s1

> <INCHI_KEY>
VWWLVBSOTCIVHI-LRVUVFPRSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.288

> <EXACT_MASS>
276.099773615

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.399866246919732

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
1.7899725073333328

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.879285600367524

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.047881664568184

> <JCHEM_PKA_STRONGEST_BASIC>
-3.65131064294597

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
71.3617

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.667  -6.160   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Value	Source
Goniodiol 8-acetic acid	Generator

Chemical Formula

C₁₅H₁₆O₅

Average Mass

276.2880 Da

Monoisotopic Mass

276.09977 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(=O)OC(C(O)[C@H]1CC=CC(=O)O1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H16O5/c1-10(16)19-15(11-6-3-2-4-7-11)14(18)12-8-5-9-13(17)20-12/h2-7,9,12,14-15,18H,8H2,1H3/t12-,14?,15?/m1/s1

InChI Key

VWWLVBSOTCIVHI-LRVUVFPRSA-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 amuyon	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
Pyran
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.79	ChemAxon
pKa (Strongest Acidic)	13.05	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	71.36 m³·mol⁻¹	ChemAxon
Polarizability	27.4 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

95532495

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129317213

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-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate (NP0195987)

MOL for NP0195987 (2-hydroxy-2-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate)

3D MOL for NP0195987 (2-hydroxy-2-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate)

3D SDF for NP0195987 (2-hydroxy-2-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate)

3D-SDF for NP0195987 (2-hydroxy-2-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate)

PDB for NP0195987 (2-hydroxy-2-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate)

3D PDB for NP0195987 (2-hydroxy-2-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate)

SMILES for NP0195987 (2-hydroxy-2-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate)

INCHI for NP0195987 (2-hydroxy-2-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate)

Structure for NP0195987 (2-hydroxy-2-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate)

3D Structure for NP0195987 (2-hydroxy-2-[(2r)-6-oxo-2,3-dihydropyran-2-yl]-1-phenylethyl acetate)