NP-MRD: Showing NP-Card for 4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione (NP0324838)

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Record Information

Version

2.0

Created at

2022-09-12 05:09:25 UTC

Updated at

2022-09-12 05:09:25 UTC

NP-MRD ID

NP0324838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione

Description

4,11-Dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadeca-1,7,9(17),13,15-pentaene-3,12-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. 4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione is found in Gentiana asclepiadea. 4,11-Dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]Heptadeca-1,7,9(17),13,15-pentaene-3,12-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251515562D          

 19 22  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  7  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  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  0  0  0  0
  5 19  2  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0324838

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=C1OCC2=C3C1=CC=CC3=C1C(=O)OCCC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O4/c16-14-11-3-1-2-10-12(11)9(7-19-14)6-8-4-5-18-15(17)13(8)10/h1-3,6H,4-5,7H2

> <INCHI_KEY>
XJXPHHGLGJZRIG-UHFFFAOYSA-N

> <FORMULA>
C15H10O4

> <MOLECULAR_WEIGHT>
254.241

> <EXACT_MASS>
254.057908802

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
25.133882366922098

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1,7,9(17),13,15-pentaene-3,12-dione

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.360792308333333

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.6310646959573365

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
68.423

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.98e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1,7,9(17),13,15-pentaene-3,12-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  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      10.669   0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7   14                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    2   19                                                  
CONECT   19   18    5   14                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₀O₄

Average Mass

254.2410 Da

Monoisotopic Mass

254.05791 Da

IUPAC Name

4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1,7,9(17),13,15-pentaene-3,12-dione

Traditional Name

4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1,7,9(17),13,15-pentaene-3,12-dione

CAS Registry Number

Not Available

SMILES

O=C1OCC2=C3C1=CC=CC3=C1C(=O)OCCC1=C2

InChI Identifier

InChI=1S/C15H10O4/c16-14-11-3-1-2-10-12(11)9(7-19-14)6-8-4-5-18-15(17)13(8)10/h1-3,6H,4-5,7H2

InChI Key

XJXPHHGLGJZRIG-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gentiana asclepiadea	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
Benzopyran
Isochromane
Naphthalene
2-benzopyran
Dicarboxylic acid or derivatives
Pyran
Benzenoid
Lactone
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Organic oxide
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	2.16	ALOGPS
logP	2.36	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.42 m³·mol⁻¹	ChemAxon
Polarizability	25.13 Å³	ChemAxon
Number of Rings	4	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

15735800

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione (NP0324838)

MOL for NP0324838 (4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione)

3D MOL for NP0324838 (4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione)

3D SDF for NP0324838 (4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione)

3D-SDF for NP0324838 (4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione)

PDB for NP0324838 (4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione)

3D PDB for NP0324838 (4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione)

SMILES for NP0324838 (4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione)

INCHI for NP0324838 (4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione)

Structure for NP0324838 (4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione)

3D Structure for NP0324838 (4,11-dioxatetracyclo[7.7.1.0²,⁷.0¹³,¹⁷]heptadeca-1(16),2(7),8,13(17),14-pentaene-3,12-dione)