NP-MRD: Showing NP-Card for methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate (NP0260686)

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Record Information

Version

2.0

Created at

2022-09-08 02:55:08 UTC

Updated at

2022-09-08 02:55:08 UTC

NP-MRD ID

NP0260686

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate

Description

Methyl 2-(2,2-dimethyl-6-oxo-3a,6,7,7a-tetrahydro-2H-1,3-benzodioxol-3a-yl)acetate belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate is found in Ajuga parviflora and Jacobaea argunensis. Methyl 2-(2,2-dimethyl-6-oxo-3a,6,7,7a-tetrahydro-2H-1,3-benzodioxol-3a-yl)acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 34  0  0  0  0  0  0  0  0999 V2000
    4.2022   -1.3519   -0.5001 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8919   -1.0361   -0.9974 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3261    0.2095   -0.7971 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0493    1.0393   -0.1468 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9741    0.5709   -1.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0576    0.5050   -0.1800 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3745    1.4552    0.8516 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0875    2.6792    0.8686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0400    3.0629   -0.1640 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9985    4.2249   -0.6880 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0377    2.0332   -0.5537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4481    0.6592   -0.6614 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1591   -0.1738    0.2345 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3362   -1.2877    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7157   -2.0721    1.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6523   -2.1465   -0.9194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0558   -0.8147    0.2925 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2346   -1.2132    0.6037 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4731   -2.3913   -0.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9614   -0.6907   -0.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0278    1.6233   -1.6598 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7209   -0.1157   -2.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0895    1.1724    1.6309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2200    3.4180    1.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5790    2.3138   -1.4803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8107    2.0593    0.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6118    0.2121   -1.6766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6799   -2.5989    1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9641   -1.4096    2.3688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0055   -2.8714    1.7644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1246   -1.8154   -1.8270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4409   -3.2060   -0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7404   -2.0431   -1.1235 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  6  5  1  6
  6 17  1  0
 17 14  1  0
 14 15  1  0
 14 16  1  0
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  9  1  0
  9 10  2  0
  9  8  1  0
  8  7  2  0
 12  6  1  0
  7  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  5 21  1  0
  5 22  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 16 33  1  0
 12 27  1  6
 11 25  1  0
 11 26  1  0
  8 24  1  0
  7 23  1  0
M  END


  Mrv1533004241510252D          

 17 18  0  0  0  0            999 V2000
   -1.0387   -3.4225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2850   -3.0870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1988   -2.2665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8662   -1.7816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549   -1.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415   -1.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2415   -0.1459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
  6 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0260686

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)CC12OC(C)(C)OC1CC(=O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H16O5/c1-11(2)16-9-6-8(13)4-5-12(9,17-11)7-10(14)15-3/h4-5,9H,6-7H2,1-3H3

> <INCHI_KEY>
RILPFFNPAKGKIG-UHFFFAOYSA-N

> <FORMULA>
C12H16O5

> <MOLECULAR_WEIGHT>
240.255

> <EXACT_MASS>
240.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
33

> <JCHEM_AVERAGE_POLARIZABILITY>
23.75665139417494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-(2,2-dimethyl-6-oxo-3a,6,7,7a-tetrahydro-2H-1,3-benzodioxol-3a-yl)acetate

> <ALOGPS_LOGP>
0.54

> <JCHEM_LOGP>
0.8232939703333328

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.91639578713012

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0963047194807505

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
59.71340000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.15e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)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      -1.939  -6.389   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.532  -5.762   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.371  -4.231   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.617  -3.326   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.036  -3.604   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.268  -2.549   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.318  -2.333   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.318  -0.272   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.268  -0.057   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   12   17                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16    6                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2-(2,2-dimethyl-6-oxo-3a,6,7,7a-tetrahydro-2H-1,3-benzodioxol-3a-yl)acetic acid	Generator

Chemical Formula

C₁₂H₁₆O₅

Average Mass

240.2550 Da

Monoisotopic Mass

240.09977 Da

IUPAC Name

methyl 2-(2,2-dimethyl-6-oxo-3a,6,7,7a-tetrahydro-2H-1,3-benzodioxol-3a-yl)acetate

Traditional Name

methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate

CAS Registry Number

Not Available

SMILES

COC(=O)CC12OC(C)(C)OC1CC(=O)C=C2

InChI Identifier

InChI=1S/C12H16O5/c1-11(2)16-9-6-8(13)4-5-12(9,17-11)7-10(14)15-3/h4-5,9H,6-7H2,1-3H3

InChI Key

RILPFFNPAKGKIG-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
Ajuga parviflora	LOTUS Database	35616633
Jacobaea argunensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Cyclohexenone
Methyl ester
Meta-dioxolane
Cyclic ketone
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
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	0.54	ALOGPS
logP	0.82	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	16.92	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.71 m³·mol⁻¹	ChemAxon
Polarizability	23.76 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 methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate (NP0260686)

MOL for NP0260686 (methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate)

3D MOL for NP0260686 (methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate)

3D SDF for NP0260686 (methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate)

3D-SDF for NP0260686 (methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate)

PDB for NP0260686 (methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate)

3D PDB for NP0260686 (methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate)

SMILES for NP0260686 (methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate)

INCHI for NP0260686 (methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate)

Structure for NP0260686 (methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate)

3D Structure for NP0260686 (methyl 2-(2,2-dimethyl-6-oxo-7,7a-dihydro-1,3-benzodioxol-3a-yl)acetate)