NP-MRD: Showing NP-Card for Tubakialactone D (NP0043996)

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Record Information

Version

1.0

Created at

2021-06-22 17:44:36 UTC

Updated at

2021-06-22 17:44:36 UTC

NP-MRD ID

NP0043996

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tubakialactone D

Description

3-Hydroxy-5,7-dimethoxy-3-methyl-1,3-dihydro-2-benzofuran-1-one belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone. Tubakialactone D is found in Tubakia sp. ECN-111. It was first documented in 2017 (Nakashima, et al.). Based on a literature review very few articles have been published on 3-hydroxy-5,7-dimethoxy-3-methyl-1,3-dihydro-2-benzofuran-1-one.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306222119442D          

 16 17  0  0  0  0            999 V2000
    0.4243    0.3820    0.0000 C   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
    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
    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
    1.9233   -1.1104    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
    0.8838   -2.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 O   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   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    0.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4743    0.7232    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  2 11  1  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043996

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(OC)=C2C(=O)OC(C)(O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O5/c1-11(13)7-4-6(14-2)5-8(15-3)9(7)10(12)16-11/h4-5,13H,1-3H3

> <INCHI_KEY>
RMGNNSPUTGOLDS-UHFFFAOYSA-N

> <FORMULA>
C11H12O5

> <MOLECULAR_WEIGHT>
224.212

> <EXACT_MASS>
224.068473486

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
21.627559283679318

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-5,7-dimethoxy-3-methyl-1,3-dihydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
1.096446334

> <ALOGPS_LOGS>
-1.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.049446619458294

> <JCHEM_PKA_STRONGEST_BASIC>
-4.526772048648941

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
55.616

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-5,7-dimethoxy-3-methyl-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0       0.792   0.713   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.650  -4.013   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.220  -1.303   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.924  -4.383   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       3.590  -5.153   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       7.591   0.237   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.591   1.777   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.752   1.350   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11   16                                             
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    3    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    2                                                       
CONECT   12    7   13                                                       
CONECT   13   12                                                            
CONECT   14    5   15                                                       
CONECT   15   14                                                            
CONECT   16    2                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    NP0043996
HETATM    1  C1  UNL     1       3.317  -1.869  -0.033  1.00  0.00           C  
HETATM    2  O1  UNL     1       1.944  -2.142  -0.197  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.000  -1.126  -0.179  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.436   0.174   0.003  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.537   1.213   0.028  1.00  0.00           C  
HETATM    6  O2  UNL     1       1.007   2.495   0.212  1.00  0.00           O  
HETATM    7  C5  UNL     1       2.351   2.830   0.380  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.790   0.921  -0.134  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.238  -0.371  -0.317  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.345  -1.421  -0.343  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.720  -0.365  -0.461  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.375  -1.118   0.695  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.068  -0.922  -1.685  1.00  0.00           O  
HETATM   14  O4  UNL     1      -3.112   0.986  -0.354  1.00  0.00           O  
HETATM   15  C11 UNL     1      -1.973   1.754  -0.160  1.00  0.00           C  
HETATM   16  O5  UNL     1      -1.923   3.016  -0.019  1.00  0.00           O  
HETATM   17  H1  UNL     1       3.666  -1.205  -0.838  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.402  -1.290   0.928  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.912  -2.776   0.110  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.497   0.351   0.126  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.894   2.155   1.076  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.381   3.866   0.825  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.916   2.856  -0.588  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.610  -2.451  -0.480  1.00  0.00           H  
HETATM   25  H9  UNL     1      -4.448  -0.811   0.680  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.290  -2.207   0.586  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.885  -0.733   1.619  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.482  -1.812  -1.480  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4   10
CONECT    4    5   20
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   21   22   23
CONECT    8    9   15
CONECT    9   10   10   11
CONECT   10   24
CONECT   11   12   13   14
CONECT   12   25   26   27
CONECT   13   28
CONECT   14   15
CONECT   15   16   16
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂O₅

Average Mass

224.2120 Da

Monoisotopic Mass

224.06847 Da

IUPAC Name

3-hydroxy-5,7-dimethoxy-3-methyl-1,3-dihydro-2-benzofuran-1-one

Traditional Name

3-hydroxy-5,7-dimethoxy-3-methyl-2-benzofuran-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(OC)=C2C(=O)OC(C)(O)C2=C1

InChI Identifier

InChI=1S/C11H12O5/c1-11(13)7-4-6(14-2)5-8(15-3)9(7)10(12)16-11/h4-5,13H,1-3H3

InChI Key

RMGNNSPUTGOLDS-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Tubakia sp. ECN-111	Linigton's dataset	Ken-ichi Nakashima, Junko Tomida, Takao Hirai, Yuji Morita, Yoshiaki Kawamura, Makoto Inoue. Tuba...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzofuranones. These are organic compounds containing a benzene ring fused to a furanone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzofurans

Sub Class

Benzofuranones

Direct Parent

Benzofuranones

Alternative Parents

Substituents

Isobenzofuranone
Phthalide
Benzofuranone
Isocoumaran
Anisole
Alkyl aryl ether
Benzenoid
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	0.87	ALOGPS
logP	1.1	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	11.05	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.62 m³·mol⁻¹	ChemAxon
Polarizability	21.63 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

78435285

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139591206

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ken-ichi Nakashima, Junko Tomida, Takao Hirai, Yuji Morita, Yoshiaki Kawamura, Makoto Inoue (2017). Ken-ichi Nakashima, Junko Tomida, Takao Hirai, Yuji Morita, Yoshiaki Kawamura, Makoto Inoue. Tubakialactones A–E, new polyketides from the endophytic fungus Tubakia sp. ECN-111. Tetrahedron Letters Volume 58, Issue 23, 7 June 2017, Pages 2248-2251. DOI: 10.1016/j.tetlet.2017.04.076. Tetrahedron Letters.

Showing NP-Card for Tubakialactone D (NP0043996)

MOL for NP0043996 (Tubakialactone D)

3D MOL for NP0043996 (Tubakialactone D)

3D SDF for NP0043996 (Tubakialactone D)

3D-SDF for NP0043996 (Tubakialactone D)

PDB for NP0043996 (Tubakialactone D)

3D PDB for NP0043996 (Tubakialactone D)

SMILES for NP0043996 (Tubakialactone D)

INCHI for NP0043996 (Tubakialactone D)

Structure for NP0043996 (Tubakialactone D)

3D Structure for NP0043996 (Tubakialactone D)