NP-MRD: Showing NP-Card for norpinguisone methyl ester (NP0219428)

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Record Information

Version

1.0

Created at

2022-09-05 20:24:38 UTC

Updated at

2022-09-05 20:24:38 UTC

NP-MRD ID

NP0219428

Secondary Accession Numbers

None

Natural Product Identification

Common Name

norpinguisone methyl ester

Description

Norpinguisone Methyl Ester 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. norpinguisone methyl ester is found in Bryopteris filicina, Porella cordaeana and Porella navicularis. It was first documented in 2010 (PMID: 20302921). Based on a literature review very few articles have been published on Norpinguisone Methyl Ester.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222242D          

 19 21  0  0  1  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  1  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  1  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
    1.1387   -0.0305    0.0000 C   0  0  1  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
  5  3  1  1  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  1  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0219428

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]12CC3=C(C=CO3)C(=O)[C@]1(C)CC[C@H]2C

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O4/c1-9-4-6-14(2)12(16)10-5-7-19-11(10)8-15(9,14)13(17)18-3/h5,7,9H,4,6,8H2,1-3H3/t9-,14+,15+/m1/s1

> <INCHI_KEY>
HKOZPZRWAYCCLH-NKZPBKNFSA-N

> <FORMULA>
C15H18O4

> <MOLECULAR_WEIGHT>
262.305

> <EXACT_MASS>
262.12050906

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
27.28866422455474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (4aR,7R,7aR)-4a,7-dimethyl-4-oxo-4H,4aH,5H,6H,7H,7aH,8H-indeno[5,6-b]furan-7a-carboxylate

> <JCHEM_LOGP>
2.476979162666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0474385748061894

> <JCHEM_POLAR_SURFACE_AREA>
56.51

> <JCHEM_REFRACTIVITY>
68.8045

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4aR,7R,7aR)-4a,7-dimethyl-4-oxo-5H,6H,7H,8H-indeno[5,6-b]furan-7a-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       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  C   UNK     0       2.126  -0.057   0.000  0.00  0.00           C+0
HETATM   19  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   18                                             
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                                                       
CONECT   18   17    5   19                                                  
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₈O₄

Average Mass

262.3050 Da

Monoisotopic Mass

262.12051 Da

IUPAC Name

methyl (4aR,7R,7aR)-4a,7-dimethyl-4-oxo-4H,4aH,5H,6H,7H,7aH,8H-indeno[5,6-b]furan-7a-carboxylate

Traditional Name

methyl (4aR,7R,7aR)-4a,7-dimethyl-4-oxo-5H,6H,7H,8H-indeno[5,6-b]furan-7a-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]12CC3=C(C=CO3)C(=O)[C@]1(C)CC[C@H]2C

InChI Identifier

InChI=1S/C15H18O4/c1-9-4-6-14(2)12(16)10-5-7-19-11(10)8-15(9,14)13(17)18-3/h5,7,9H,4,6,8H2,1-3H3/t9-,14+,15+/m1/s1

InChI Key

HKOZPZRWAYCCLH-NKZPBKNFSA-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
Porella cordaeana	LOTUS Database	35616633
Porella navicularis	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 alkyl ketone
Aryl ketone
Furan
Heteroaromatic compound
Methyl ester
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzofurans (CHEBI:67835 )

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	2.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	56.51 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.8 m³·mol⁻¹	ChemAxon
Polarizability	27.29 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

26343631

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14164937

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Quang DN, Asakawa Y: Chemical constituents of the Vietnamese liverwort Porella densifolia. Fitoterapia. 2010 Sep;81(6):659-61. doi: 10.1016/j.fitote.2010.03.014. Epub 2010 Mar 17. [PubMed:20302921 ]
LOTUS database [Link]

Showing NP-Card for norpinguisone methyl ester (NP0219428)

MOL for NP0219428 (norpinguisone methyl ester)

3D MOL for NP0219428 (norpinguisone methyl ester)

3D SDF for NP0219428 (norpinguisone methyl ester)

3D-SDF for NP0219428 (norpinguisone methyl ester)

PDB for NP0219428 (norpinguisone methyl ester)

3D PDB for NP0219428 (norpinguisone methyl ester)

SMILES for NP0219428 (norpinguisone methyl ester)

INCHI for NP0219428 (norpinguisone methyl ester)

Structure for NP0219428 (norpinguisone methyl ester)

3D Structure for NP0219428 (norpinguisone methyl ester)