NP-MRD: Showing NP-Card for methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate (NP0210787)

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Record Information

Version

2.0

Created at

2022-09-05 08:45:18 UTC

Updated at

2022-09-05 08:45:18 UTC

NP-MRD ID

NP0210787

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate

Description

Methyl (3S,4aR,8S,8aR)-8-hydroxy-3-methyl-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxine-6-carboxylate belongs to the class of organic compounds known as 1,4-dioxanes. These are organic compounds containing 1,4-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 4. methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate is found in Phyllosticta cirsii. Based on a literature review very few articles have been published on methyl (3S,4aR,8S,8aR)-8-hydroxy-3-methyl-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxine-6-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
    4.8379    1.2388   -0.2436 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5000    0.9276    0.0802 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9230   -0.2208   -0.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6642   -0.9350   -1.1987 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5484   -0.6102   -0.1541 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945   -1.7148   -0.6955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2950   -2.1394   -0.4253 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7496   -3.1148   -1.2830 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1403   -0.8837   -0.4669 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5076   -1.1452   -0.4312 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3533   -0.1231   -0.0287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5552   -0.1065   -0.3534 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8038    0.9603    0.8014 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4774    2.2566    0.3307 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4541    1.1402    0.6695 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.0362    0.7117 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7454    0.2654    0.7327 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1897    2.0463    0.4329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9714    1.5080   -1.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5277    0.3744   -0.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417   -2.2891   -1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -2.4864    0.6455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6371   -4.0214   -0.8890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -0.2904   -1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1456    0.8068    1.8517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7983    2.7659   -0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6555    2.9506    1.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4067    2.0445   -0.2302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9525   -0.6292    1.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9238    1.3400    0.4941 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1714    0.1208    1.7684 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
  5  6  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  5  1  0
 16  9  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  1
  8 23  1  0
  9 24  1  6
 13 25  1  1
 14 26  1  0
 14 27  1  0
 14 28  1  0
 16 29  1  1
 17 30  1  0
 17 31  1  0
M  END


  Mrv1652309052210452D          

 17 18  0  0  1  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 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    0.7145   -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  2  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
    2.1434   -0.4125    0.0000 C   0  0  1  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
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  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  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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 16 15  1  6  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
  5 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210787

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C[C@H](O)[C@H]2OC(=O)[C@H](C)O[C@@H]2C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O6/c1-5-10(13)17-9-7(12)3-6(11(14)15-2)4-8(9)16-5/h3,5,7-9,12H,4H2,1-2H3/t5-,7-,8+,9+/m0/s1

> <INCHI_KEY>
YRHWCZIEBATYGC-URJBTRRKSA-N

> <FORMULA>
C11H14O6

> <MOLECULAR_WEIGHT>
242.227

> <EXACT_MASS>
242.079038171

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.776796873915863

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (3S,4aR,8S,8aR)-8-hydroxy-3-methyl-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxine-6-carboxylate

> <JCHEM_LOGP>
0.09349849133333352

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.642265106768352

> <JCHEM_PKA_STRONGEST_BASIC>
-3.392673242299522

> <JCHEM_POLAR_SURFACE_AREA>
82.06000000000002

> <JCHEM_REFRACTIVITY>
55.56690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3S,4aR,8S,8aR)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3H-1,4-benzodioxine-6-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -1.334  -2.310   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   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   17                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   17                                                  
CONECT   17   16    5                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
Methyl (3S,4ar,8S,8ar)-8-hydroxy-3-methyl-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxine-6-carboxylic acid	Generator

Chemical Formula

C₁₁H₁₄O₆

Average Mass

242.2270 Da

Monoisotopic Mass

242.07904 Da

IUPAC Name

methyl (3S,4aR,8S,8aR)-8-hydroxy-3-methyl-2-oxo-2,3,4a,5,8,8a-hexahydro-1,4-benzodioxine-6-carboxylate

Traditional Name

methyl (3S,4aR,8S,8aR)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3H-1,4-benzodioxine-6-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C[C@H](O)[C@H]2OC(=O)[C@H](C)O[C@@H]2C1

InChI Identifier

InChI=1S/C11H14O6/c1-5-10(13)17-9-7(12)3-6(11(14)15-2)4-8(9)16-5/h3,5,7-9,12H,4H2,1-2H3/t5-,7-,8+,9+/m0/s1

InChI Key

YRHWCZIEBATYGC-URJBTRRKSA-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
Phyllosticta cirsii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1,4-dioxanes. These are organic compounds containing 1,4-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 4.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Dioxanes

Sub Class

1,4-dioxanes

Direct Parent

1,4-dioxanes

Alternative Parents

Substituents

Para-dioxane
Dicarboxylic acid or derivatives
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Secondary alcohol
Ether
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
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	0.093	ChemAxon
pKa (Strongest Acidic)	13.64	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.57 m³·mol⁻¹	ChemAxon
Polarizability	23.78 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

163010757

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate (NP0210787)

MOL for NP0210787 (methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate)

3D MOL for NP0210787 (methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate)

3D SDF for NP0210787 (methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate)

3D-SDF for NP0210787 (methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate)

PDB for NP0210787 (methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate)

3D PDB for NP0210787 (methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate)

SMILES for NP0210787 (methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate)

INCHI for NP0210787 (methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate)

Structure for NP0210787 (methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate)

3D Structure for NP0210787 (methyl (3s,4ar,8s,8ar)-8-hydroxy-3-methyl-2-oxo-4a,5,8,8a-tetrahydro-3h-1,4-benzodioxine-6-carboxylate)