NP-MRD: Showing NP-Card for (+)-Epoxydon monoacetate (NP0066278)

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Record Information

Version

2.0

Created at

2022-04-28 10:33:12 UTC

Updated at

2022-04-28 10:33:12 UTC

NP-MRD ID

NP0066278

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Epoxydon monoacetate

Description

(1Alpha,6alpha)-3-(Acetoxymethyl)-5beta-hydroxy-7-oxabicyclo[4.1.0]Hepta-3-ene-2-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. (+)-Epoxydon monoacetate is found in Apiospora montagnei, Arthrinium arundinis, Ascochyta chrysanthemi, Mycosphaerella ligulicola, Phoma chrysanthemi and Stagonosporopsis ligulicola. Based on a literature review very few articles have been published on (1alpha,6alpha)-3-(Acetoxymethyl)-5beta-hydroxy-7-oxabicyclo[4.1.0]Hepta-3-ene-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282212332D          

 14 15  0  0  1  0            999 V2000
    0.4763   -0.8250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4763   -0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9053   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3342   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7631   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0487   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382   -0.4125    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  2  0  0  0  0
  5  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
  3 13  1  6  0  0  0
  2 14  1  6  0  0  0
  1 14  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0066278

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=C[C@@H](O)[C@H]2O[C@H]2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O5/c1-4(10)13-3-5-2-6(11)8-9(14-8)7(5)12/h2,6,8-9,11H,3H2,1H3/t6-,8-,9+/m1/s1

> <INCHI_KEY>
LJUIMTRKOODZAJ-VDAHYXPESA-N

> <FORMULA>
C9H10O5

> <MOLECULAR_WEIGHT>
198.174

> <EXACT_MASS>
198.052823422

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
18.37280166994931

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,5R,6R)-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl acetate

> <ALOGPS_LOGP>
-0.65

> <JCHEM_LOGP>
-0.6613396049999996

> <ALOGPS_LOGS>
-0.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.67071267459554

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.653277676397831

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3877265612637304

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
45.17510000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,5R,6R)-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       0.889  -1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.889  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.223   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.556  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.556  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.223  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.223  -3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.890  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.224  -1.540   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.558  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.891  -1.540   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.558  -3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.223   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -0.445  -0.770   0.000  0.00  0.00           O+0
CONECT    1    2    6   14                                                  
CONECT    2    1    3   14                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    3                                                            
CONECT   14    2    1                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
(1a,6a)-3-(Acetoxymethyl)-5b-hydroxy-7-oxabicyclo[4.1.0]hepta-3-ene-2-one	Generator
(1Α,6α)-3-(acetoxymethyl)-5β-hydroxy-7-oxabicyclo[4.1.0]hepta-3-ene-2-one	Generator

Chemical Formula

C₉H₁₀O₅

Average Mass

198.1740 Da

Monoisotopic Mass

198.05282 Da

IUPAC Name

[(1R,5R,6R)-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl acetate

Traditional Name

[(1R,5R,6R)-5-hydroxy-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=C[C@@H](O)[C@H]2O[C@H]2C1=O

InChI Identifier

InChI=1S/C9H10O5/c1-4(10)13-3-5-2-6(11)8-9(14-8)7(5)12/h2,6,8-9,11H,3H2,1H3/t6-,8-,9+/m1/s1

InChI Key

LJUIMTRKOODZAJ-VDAHYXPESA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Apiospora montagnei	Fungi	KNApSAcK
Arthrinium arundinis	LOTUS Database	35616633
Ascochyta chrysanthemi	Fungi	KNApSAcK
Mycosphaerella ligulicola	Fungi	KNApSAcK
Phoma chrysanthemi	Fungi	KNApSAcK
Stagonosporopsis ligulicola	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
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	-0.65	ALOGPS
logP	-0.66	ChemAxon
logS	-0.23	ALOGPS
pKa (Strongest Acidic)	13.65	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.18 m³·mol⁻¹	ChemAxon
Polarizability	18.37 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

61702315

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101414027

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (+)-Epoxydon monoacetate (NP0066278)

MOL for NP0066278 ((+)-Epoxydon monoacetate)

3D MOL for NP0066278 ((+)-Epoxydon monoacetate)

3D SDF for NP0066278 ((+)-Epoxydon monoacetate)

3D-SDF for NP0066278 ((+)-Epoxydon monoacetate)

PDB for NP0066278 ((+)-Epoxydon monoacetate)

3D PDB for NP0066278 ((+)-Epoxydon monoacetate)

SMILES for NP0066278 ((+)-Epoxydon monoacetate)

INCHI for NP0066278 ((+)-Epoxydon monoacetate)

Structure for NP0066278 ((+)-Epoxydon monoacetate)

3D Structure for NP0066278 ((+)-Epoxydon monoacetate)