NP-MRD: Showing NP-Card for dihydroechinofuran (NP0199079)

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Record Information

Version

2.0

Created at

2022-09-04 17:39:17 UTC

Updated at

2022-09-04 17:39:17 UTC

NP-MRD ID

NP0199079

Secondary Accession Numbers

None

Natural Product Identification

Common Name

dihydroechinofuran

Description

2-[4-(4-Methylpent-3-en-1-yl)-2,5-dihydrofuran-2-yl]cyclohexa-2,5-diene-1,4-dione belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain. dihydroechinofuran is found in Lithospermum erythrorhizon. 2-[4-(4-Methylpent-3-en-1-yl)-2,5-dihydrofuran-2-yl]cyclohexa-2,5-diene-1,4-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 38  0  0  0  0  0  0  0  0999 V2000
    4.1304   -0.5617   -1.5603 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1305    0.7113   -0.8165 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4263    1.5111   -0.9640 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2069    1.2422   -0.0706 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8678    0.8179    0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4749   -0.5164   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0687   -0.8745    0.2514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7912   -0.1845    0.9431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0267   -1.0061    1.0625 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2491   -0.2183    0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1950    1.0669    0.5187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4217    1.8443    0.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3724    3.0768   -0.0109 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7232    1.2227    0.3482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7905   -0.0633    0.6435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5793   -0.8104    0.8815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6934   -2.0445    1.1622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985   -1.9508    0.0191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5370   -2.1701   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4552   -0.5224   -2.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9440   -1.4626   -0.9658 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1713   -0.7597   -1.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1190    1.1411   -0.1799 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2045    2.5976   -0.8650 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8801    1.3446   -1.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5144    2.2498    0.3716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1337    1.5907   -0.0916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7159    0.9241    1.4331 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4776   -0.6010   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1053   -1.2957    0.3601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    0.7912    1.3437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0229   -1.5336    2.0253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2558    1.5953    0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6364    1.7862    0.1688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7661   -0.5157    0.6968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2501   -2.3806   -1.1739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1963   -2.9937    0.5567 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 18  1  0
 18 19  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 19  7  1  0
 16 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  5 28  1  0
  6 29  1  0
  6 30  1  0
  8 31  1  0
  9 32  1  1
 19 36  1  0
 19 37  1  0
 11 33  1  0
 14 34  1  0
 15 35  1  0
M  END


  Mrv1533004231521162D          

 19 20  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3819   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270   -2.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -2.5070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0470   -1.7224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6119   -3.1745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4324   -3.0882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9173   -3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7378   -3.6695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5817   -4.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7613   -4.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2763   -3.9282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4559   -4.0144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 11 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0199079

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC1=CC(OC1)C1=CC(=O)C=CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O3/c1-11(2)4-3-5-12-8-16(19-10-12)14-9-13(17)6-7-15(14)18/h4,6-9,16H,3,5,10H2,1-2H3

> <INCHI_KEY>
MQVIMAJNAQWVSP-UHFFFAOYSA-N

> <FORMULA>
C16H18O3

> <MOLECULAR_WEIGHT>
258.317

> <EXACT_MASS>
258.12559444

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
28.18202908206975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[4-(4-methylpent-3-en-1-yl)-2,5-dihydrofuran-2-yl]cyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
2.22

> <JCHEM_LOGP>
3.1005529943333325

> <ALOGPS_LOGS>
-3.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.642576147895067

> <JCHEM_PKA_STRONGEST_BASIC>
-4.234144227841104

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
78.01619999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.43e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[4-(4-methylpent-3-en-1-yl)-2,5-dihydrofuran-2-yl]cyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.580  -3.215   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.104  -4.680   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.564  -4.680   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.088  -3.215   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.009  -5.926   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.540  -5.765   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.446  -7.011   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.977  -6.850   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       4.819  -8.417   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.288  -8.578   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.382  -7.333   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.851  -7.494   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9    6                                                       
CONECT   11    8   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   11   18                                                  
CONECT   18   17                                                            
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₈O₃

Average Mass

258.3170 Da

Monoisotopic Mass

258.12559 Da

IUPAC Name

2-[4-(4-methylpent-3-en-1-yl)-2,5-dihydrofuran-2-yl]cyclohexa-2,5-diene-1,4-dione

Traditional Name

2-[4-(4-methylpent-3-en-1-yl)-2,5-dihydrofuran-2-yl]cyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCCC1=CC(OC1)C1=CC(=O)C=CC1=O

InChI Identifier

InChI=1S/C16H18O3/c1-11(2)4-3-5-12-8-16(19-10-12)14-9-13(17)6-7-15(14)18/h4,6-9,16H,3,5,10H2,1-2H3

InChI Key

MQVIMAJNAQWVSP-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
Lithospermum erythrorhizon	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prenylquinones. These are quinones with a structure characterized by the quinone ring substituted by an prenyl side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Prenylquinones

Alternative Parents

Substituents

Prenylbenzoquinone
P-benzoquinone
Quinone
Dihydrofuran
Ketone
Cyclic ketone
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

prenylquinone (CHEBI:81531 )

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	2.22	ALOGPS
logP	3.1	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	16.64	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	78.02 m³·mol⁻¹	ChemAxon
Polarizability	28.18 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

C18134

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13850222

PDB ID

Not Available

ChEBI ID

81531

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for dihydroechinofuran (NP0199079)

MOL for NP0199079 (dihydroechinofuran)

3D MOL for NP0199079 (dihydroechinofuran)

3D SDF for NP0199079 (dihydroechinofuran)

3D-SDF for NP0199079 (dihydroechinofuran)

PDB for NP0199079 (dihydroechinofuran)

3D PDB for NP0199079 (dihydroechinofuran)

SMILES for NP0199079 (dihydroechinofuran)

INCHI for NP0199079 (dihydroechinofuran)

Structure for NP0199079 (dihydroechinofuran)

3D Structure for NP0199079 (dihydroechinofuran)