NP-MRD: Showing NP-Card for ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate (NP0322971)

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Record Information

Version

2.0

Created at

2022-09-12 02:05:31 UTC

Updated at

2022-09-12 02:05:32 UTC

NP-MRD ID

NP0322971

Secondary Accession Numbers

None

Natural Product Identification

Common Name

ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate

Description

Ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds. ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate is found in Alternaria gaisen. Ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 29  0  0  0  0  0  0  0  0999 V2000
    4.3411    0.0108   -0.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8464   -0.2668    0.9446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4713   -0.5949    0.9940 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4730    0.2384    0.5679 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8134    1.3599    0.1071 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0302   -0.0865    0.6113 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2678   -1.3921   -0.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7238   -1.6312   -0.2040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1757   -2.7581   -0.0817 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6173   -0.4650   -0.4423 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5452   -0.1474   -1.7793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0770    0.6669    0.4351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9810    1.8571    0.2111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1696    0.2884    1.7672 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7523    0.9494    0.1123 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8041   -0.6225   -1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3135    1.0823   -0.7144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4082   -0.2921   -0.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3865   -1.1849    1.3162 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1263    0.5451    1.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2610   -0.2403    1.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1278   -1.2527   -1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2788   -2.2352    0.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6263   -0.7333   -0.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2136   -0.6948   -2.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3864    2.7080   -0.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4495    2.1926    1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8221    1.6356   -0.4669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3523    1.0636    2.3686 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  1
 12 15  1  0
 15  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  6 21  1  1
  7 22  1  0
  7 23  1  0
 10 24  1  1
 11 25  1  0
 13 26  1  0
 13 27  1  0
 13 28  1  0
 14 29  1  0
M  END


  Mrv1533004241507452D          

 15 15  0  0  0  0            999 V2000
    4.2868   -0.0000    0.0000 C   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
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   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
    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
   -0.7145   -0.4125    0.0000 O   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 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
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    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
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
  6 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0322971

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)C1CC(=O)C(O)C(C)(O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O6/c1-3-14-8(12)6-4-5(10)7(11)9(2,13)15-6/h6-7,11,13H,3-4H2,1-2H3

> <INCHI_KEY>
RDJFMOKLERHSRJ-UHFFFAOYSA-N

> <FORMULA>
C9H14O6

> <MOLECULAR_WEIGHT>
218.205

> <EXACT_MASS>
218.079038171

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.85061598154073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate

> <ALOGPS_LOGP>
-0.44

> <JCHEM_LOGP>
-0.5311653086666666

> <ALOGPS_LOGS>
0.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.27297619713545

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.971523815616145

> <JCHEM_PKA_STRONGEST_BASIC>
-4.307855362894583

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
48.2254

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate

> <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       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   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  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12    6                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
Ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylic acid	Generator

Chemical Formula

C₉H₁₄O₆

Average Mass

218.2050 Da

Monoisotopic Mass

218.07904 Da

IUPAC Name

ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate

Traditional Name

ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate

CAS Registry Number

Not Available

SMILES

CCOC(=O)C1CC(=O)C(O)C(C)(O)O1

InChI Identifier

InChI=1S/C9H14O6/c1-3-14-8(12)6-4-5(10)7(11)9(2,13)15-6/h6-7,11,13H,3-4H2,1-2H3

InChI Key

RDJFMOKLERHSRJ-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
Alternaria gaisen	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrans. Pyrans are compounds containing a pyran ring, which is a six-member heterocyclic, non-aromatic ring with five carbon atoms, one oxygen atom and two ring double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Not Available

Direct Parent

Pyrans

Alternative Parents

Substituents

Oxane
Pyran
Carboxylic acid ester
Hemiacetal
Ketone
Secondary alcohol
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organic oxygen compound
Organooxygen compound
Carbonyl group
Organic oxide
Alcohol
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	-0.44	ALOGPS
logP	-0.53	ChemAxon
logS	0.21	ALOGPS
pKa (Strongest Acidic)	10.97	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.23 m³·mol⁻¹	ChemAxon
Polarizability	20.85 Å³	ChemAxon
Number of Rings	1	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

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 ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate (NP0322971)

MOL for NP0322971 (ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate)

3D MOL for NP0322971 (ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate)

3D SDF for NP0322971 (ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate)

3D-SDF for NP0322971 (ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate)

PDB for NP0322971 (ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate)

3D PDB for NP0322971 (ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate)

SMILES for NP0322971 (ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate)

INCHI for NP0322971 (ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate)

Structure for NP0322971 (ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate)

3D Structure for NP0322971 (ethyl 5,6-dihydroxy-6-methyl-4-oxooxane-2-carboxylate)