NP-MRD: Showing NP-Card for 2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one (NP0314880)

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Record Information

Version

2.0

Created at

2022-09-11 13:13:07 UTC

Updated at

2022-09-11 13:13:07 UTC

NP-MRD ID

NP0314880

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one

Description

2-(4,8-Dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-2H,3H,4H-furo[2,3-b]chromen-4-one belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). 2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one is found in Ferula pallida. 2-(4,8-Dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-2H,3H,4H-furo[2,3-b]chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251510102D          

 30 32  0  0  0  0            999 V2000
  -12.9535    6.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3404    5.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5558    5.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3843    6.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5997    6.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9866    6.2810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2019    6.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0304    7.3429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5888    5.9839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7604    5.1769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5450    4.9220    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1581    5.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9427    5.2191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0459    4.7644    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4328    5.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9479    4.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7183    5.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0039    5.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2894    5.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5749    5.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5749    4.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8605    5.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460    5.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1460    4.4914    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4315    5.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7170    5.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026    5.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7170    4.4914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7684    6.0701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3559    6.7846    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
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M  END

     RDKit          3D

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M  END


  Mrv1533004251510102D          

 30 32  0  0  0  0            999 V2000
  -12.9535    6.0682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.3404    5.5162    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5558    5.7711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3843    6.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0314880

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C2C(OC3=C(C(C)C(C)(CCC=C(C)CC(=O)CC(C)C)O3)C2=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C25H32O5/c1-15(2)12-18(26)13-16(3)8-7-11-25(5)17(4)22-23(27)20-10-9-19(28-6)14-21(20)29-24(22)30-25/h8-10,14-15,17H,7,11-13H2,1-6H3

> <INCHI_KEY>
WODHGNNMBPUNHS-UHFFFAOYSA-N

> <FORMULA>
C25H32O5

> <MOLECULAR_WEIGHT>
412.526

> <EXACT_MASS>
412.22497413

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
46.90156058587827

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-2H,3H,4H-furo[2,3-b]chromen-4-one

> <ALOGPS_LOGP>
5.48

> <JCHEM_LOGP>
5.368504412

> <ALOGPS_LOGS>
-5.12

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.785095916831708

> <JCHEM_PKA_STRONGEST_BASIC>
-4.606064590037763

> <JCHEM_POLAR_SURFACE_AREA>
61.830000000000005

> <JCHEM_REFRACTIVITY>
127.25469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.13e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3H-furo[2,3-b]chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0     -24.180  11.327   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0     -23.035  10.297   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0     -21.571  10.773   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -21.251  12.279   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -19.786  12.755   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -18.642  11.724   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -17.177  12.200   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0     -16.857  13.707   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0     -16.033  11.170   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -16.353   9.664   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0     -17.817   9.188   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0     -18.962  10.218   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -20.426   9.742   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0     -15.019   8.894   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0     -13.875   9.924   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -12.969   8.678   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -12.541  10.694   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -11.207   9.924   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.874  10.694   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -8.540   9.924   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -8.540   8.384   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.206  10.694   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.873   9.924   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -5.873   8.384   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.539  10.694   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.205   9.924   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -1.871  10.694   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.205   8.384   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0     -14.501  11.331   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -13.731  12.665   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   29                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11    6   13                                                  
CONECT   13   12    3                                                       
CONECT   14   10   15                                                       
CONECT   15   14   16   17   29                                             
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   15    9   30                                                  
CONECT   30   29                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₂O₅

Average Mass

412.5260 Da

Monoisotopic Mass

412.22497 Da

IUPAC Name

2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-2H,3H,4H-furo[2,3-b]chromen-4-one

Traditional Name

2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3H-furo[2,3-b]chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(OC3=C(C(C)C(C)(CCC=C(C)CC(=O)CC(C)C)O3)C2=O)=C1

InChI Identifier

InChI=1S/C25H32O5/c1-15(2)12-18(26)13-16(3)8-7-11-25(5)17(4)22-23(27)20-10-9-19(28-6)14-21(20)29-24(22)30-25/h8-10,14-15,17H,7,11-13H2,1-6H3

InChI Key

WODHGNNMBPUNHS-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
Ferula pallida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Not Available

Direct Parent

Coumarins and derivatives

Alternative Parents

Substituents

Chromone
Coumarin
Benzopyran
1-benzopyran
Furopyran
Anisole
Phenol ether
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Vinylogous ester
Furan
Heteroaromatic compound
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	5.48	ALOGPS
logP	5.37	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	16.79	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	127.25 m³·mol⁻¹	ChemAxon
Polarizability	46.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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 2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one (NP0314880)

MOL for NP0314880 (2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one)

3D MOL for NP0314880 (2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one)

3D SDF for NP0314880 (2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one)

3D-SDF for NP0314880 (2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one)

PDB for NP0314880 (2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one)

3D PDB for NP0314880 (2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one)

SMILES for NP0314880 (2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one)

INCHI for NP0314880 (2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one)

Structure for NP0314880 (2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one)

3D Structure for NP0314880 (2-(4,8-dimethyl-6-oxonon-3-en-1-yl)-7-methoxy-2,3-dimethyl-3h-furo[2,3-b]chromen-4-one)