NP-MRD: Showing NP-Card for methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate (NP0165052)

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Record Information

Version

2.0

Created at

2022-09-03 00:04:10 UTC

Updated at

2022-09-03 00:04:10 UTC

NP-MRD ID

NP0165052

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate

Description

Methyl 4a,7-dimethyl-4,6-dioxo-4H,4aH,5H,6H,7H,7aH,8H-indeno[5,6-b]furan-7a-carboxylate belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate is found in Bryopteris filicina. Methyl 4a,7-dimethyl-4,6-dioxo-4H,4aH,5H,6H,7H,7aH,8H-indeno[5,6-b]furan-7a-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
    3.2098    1.7873    0.6267 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2255    1.0783   -0.1123 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1608    0.4386    0.5028 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0942    0.5076    1.7539 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1633   -0.2865   -0.3286 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5421    0.6463   -1.2832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5468    1.4595   -0.5150 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1528    2.5675   -0.9132 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9620    3.0091    0.0044 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8892    2.1471    1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9762    1.1356    0.7508 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4483   -0.0509    1.4050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5491   -0.1384    2.6468 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8304   -1.0602    0.5178 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8832   -1.6166   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0062   -2.0935    1.1515 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9628   -2.4304    0.0622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7043   -3.3837    0.0537 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8801   -1.4212   -1.0275 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2752   -1.0464   -1.4770 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8698    2.8405    0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3299    1.4073    1.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1866    1.7636    0.1121 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2063    1.3730   -1.6712 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9961    0.1327   -2.1486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5690    3.8772   -0.0571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4184    2.1839    2.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4701   -2.4081   -1.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6974   -2.0038    0.2632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3753   -0.8089   -0.9924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510   -2.9598    1.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4902   -1.7021    2.0553 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2815   -1.8295   -1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6062   -1.8952   -2.1438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3213   -0.1509   -2.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9834   -1.0690   -0.6241 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
  5  3  1  1
  5  6  1  0
  6  7  1  0
  7 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 14  5  1  0
 19  5  1  0
  8  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  0
  6 25  1  0
 10 27  1  0
  9 26  1  0
 15 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
 19 33  1  6
 20 34  1  0
 20 35  1  0
 20 36  1  0
M  END


  Mrv1533004171502542D          

 20 22  0  0  0  0            999 V2000
    2.4183    1.8404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    1.0200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371    0.5350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0834    0.8706    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1369   -0.0305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6218   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1369   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371   -1.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    0.6369    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
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  7 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0165052

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C12CC3=C(C=CO3)C(=O)C1(C)CC(=O)C2C

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c1-8-10(16)6-14(2)12(17)9-4-5-20-11(9)7-15(8,14)13(18)19-3/h4-5,8H,6-7H2,1-3H3

> <INCHI_KEY>
NOAGOEKLGLFLHJ-UHFFFAOYSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.288

> <EXACT_MASS>
276.099773615

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.453703245402238

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 4a,7-dimethyl-4,6-dioxo-4H,4aH,5H,6H,7H,7aH,8H-indeno[5,6-b]furan-7a-carboxylate

> <ALOGPS_LOGP>
1.70

> <JCHEM_LOGP>
1.553728619333333

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.401017883379225

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0477934550853765

> <JCHEM_POLAR_SURFACE_AREA>
73.58

> <JCHEM_REFRACTIVITY>
69.4718

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.81e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4a,7-dimethyl-4,6-dioxo-5H,7H,8H-indeno[5,6-b]furan-7a-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       4.514   3.435   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       4.675   1.904   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.429   0.999   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.022   1.625   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       7.722  -0.057   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.627  -1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.722  -2.549   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.429  -3.604   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.320  -1.303   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.220   1.189   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   14   19                                             
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12    5   15   16                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17    5   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4a,7-dimethyl-4,6-dioxo-4H,4ah,5H,6H,7H,7ah,8H-indeno[5,6-b]furan-7a-carboxylic acid	Generator

Chemical Formula

C₁₅H₁₆O₅

Average Mass

276.2880 Da

Monoisotopic Mass

276.09977 Da

IUPAC Name

methyl 4a,7-dimethyl-4,6-dioxo-4H,4aH,5H,6H,7H,7aH,8H-indeno[5,6-b]furan-7a-carboxylate

Traditional Name

methyl 4a,7-dimethyl-4,6-dioxo-5H,7H,8H-indeno[5,6-b]furan-7a-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C12CC3=C(C=CO3)C(=O)C1(C)CC(=O)C2C

InChI Identifier

InChI=1S/C15H16O5/c1-8-10(16)6-14(2)12(17)9-4-5-20-11(9)7-15(8,14)13(18)19-3/h4-5,8H,6-7H2,1-3H3

InChI Key

NOAGOEKLGLFLHJ-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
Bryopteris filicina	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofurans. These are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Not Available

Direct Parent

Benzofurans

Alternative Parents

Substituents

Benzofuran
Aryl ketone
Aryl alkyl ketone
Furan
Methyl ester
Heteroaromatic compound
Carboxylic acid ester
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.7	ALOGPS
logP	1.55	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	16.4	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	73.58 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.47 m³·mol⁻¹	ChemAxon
Polarizability	27.45 Å³	ChemAxon
Number of Rings	3	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 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate (NP0165052)

MOL for NP0165052 (methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate)

3D MOL for NP0165052 (methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate)

3D SDF for NP0165052 (methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate)

3D-SDF for NP0165052 (methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate)

PDB for NP0165052 (methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate)

3D PDB for NP0165052 (methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate)

SMILES for NP0165052 (methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate)

INCHI for NP0165052 (methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate)

Structure for NP0165052 (methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate)

3D Structure for NP0165052 (methyl 4a,7-dimethyl-4,6-dioxo-5h,7h,8h-indeno[5,6-b]furan-7a-carboxylate)