NP-MRD: Showing NP-Card for 4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione (NP0224876)

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Record Information

Version

2.0

Created at

2022-09-06 03:26:01 UTC

Updated at

2022-09-06 03:26:01 UTC

NP-MRD ID

NP0224876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione

Description

4-(Furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-12,14-diene-6,11-dione belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione is found in Syzygiella autumnalis. 4-(Furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]Hexadeca-12,14-diene-6,11-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251515332D          

 25 29  0  0  0  0            999 V2000
    2.5645    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0493    1.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7941    2.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6011    2.2295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0136    1.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4615    0.9019    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  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
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 21 25  1  0  0  0  0
M  END


  Mrv1533004251515332D          

 25 29  0  0  0  0            999 V2000
    2.5645    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1340    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9590    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3509    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1794    1.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7925    2.4389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5771    2.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0493    1.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7941    2.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6011    2.2295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0136    1.5150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4615    0.9019    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  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
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  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
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
 10 19  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 21 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12C3CC4C(=O)OC(CC4(C)C1C=CC=C2C(=O)O3)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H20O5/c1-19-9-14(11-6-7-23-10-11)24-18(22)13(19)8-16-20(2)12(17(21)25-16)4-3-5-15(19)20/h3-7,10,13-16H,8-9H2,1-2H3

> <INCHI_KEY>
XEZOJYUGDLQLHQ-UHFFFAOYSA-N

> <FORMULA>
C20H20O5

> <MOLECULAR_WEIGHT>
340.375

> <EXACT_MASS>
340.131073744

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
45

> <JCHEM_AVERAGE_POLARIZABILITY>
34.93475518843198

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione

> <ALOGPS_LOGP>
3.42

> <JCHEM_LOGP>
2.7517702886666657

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8885658278615236

> <JCHEM_POLAR_SURFACE_AREA>
65.74000000000001

> <JCHEM_REFRACTIVITY>
89.93110000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.39e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione

> <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       4.787   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.454  -0.000   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.453  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.120  -0.000   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.655  -0.476   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.250   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.790   0.770   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.655   2.016   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.335   3.522   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.479   4.553   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.944   4.077   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.453   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.120   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.959   3.072   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.788   2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.949   3.842   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      10.455   4.162   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      11.225   2.828   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.195   1.684   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   18                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    2   19                                                  
CONECT   19   18   10   14   20                                             
CONECT   20   19                                                            
CONECT   21    4   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₀O₅

Average Mass

340.3750 Da

Monoisotopic Mass

340.13107 Da

IUPAC Name

4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione

Traditional Name

4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione

CAS Registry Number

Not Available

SMILES

CC12C3CC4C(=O)OC(CC4(C)C1C=CC=C2C(=O)O3)C1=COC=C1

InChI Identifier

InChI=1S/C20H20O5/c1-19-9-14(11-6-7-23-10-11)24-18(22)13(19)8-16-20(2)12(17(21)25-16)4-3-5-15(19)20/h3-7,10,13-16H,8-9H2,1-2H3

InChI Key

XEZOJYUGDLQLHQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Jamesoniella autumnalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxane
Pyran
Heteroaromatic compound
Furan
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen 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	3.42	ALOGPS
logP	2.75	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.74 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.93 m³·mol⁻¹	ChemAxon
Polarizability	34.93 Å³	ChemAxon
Number of Rings	5	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 4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione (NP0224876)

MOL for NP0224876 (4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione)

3D MOL for NP0224876 (4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione)

3D SDF for NP0224876 (4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione)

3D-SDF for NP0224876 (4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione)

PDB for NP0224876 (4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione)

3D PDB for NP0224876 (4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione)

SMILES for NP0224876 (4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione)

INCHI for NP0224876 (4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione)

Structure for NP0224876 (4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione)

3D Structure for NP0224876 (4-(furan-3-yl)-2,16-dimethyl-5,10-dioxatetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadeca-12,14-diene-6,11-dione)