NP-MRD: Showing NP-Card for {8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate (NP0234802)

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Record Information

Version

2.0

Created at

2022-09-06 17:04:19 UTC

Updated at

2022-09-06 17:04:19 UTC

NP-MRD ID

NP0234802

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate

Description

{8-Hydroxy-4,9-dioxo-4H,9H-naphtho[2,3-c]furan-1-yl}methyl acetate belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. {8-Hydroxy-4,9-dioxo-4H,9H-naphtho[2,3-c]furan-1-yl}methyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004251506282D          

 21 23  0  0  0  0            999 V2000
   -0.2706   -4.5152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5363   -4.3437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0884   -4.9567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7913   -3.5590    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5983   -3.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -2.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3683   -1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8532   -1.2680    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
    3.3523   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668   -2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -2.7604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -2.3479    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
  2  4  1  0  0  0  0
  4  5  1  0  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  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 12 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
  6 21  2  0  0  0  0
  9 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0234802

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC1=C2C(=CO1)C(=O)C1=CC=CC(O)=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H10O6/c1-7(16)20-6-11-13-9(5-21-11)14(18)8-3-2-4-10(17)12(8)15(13)19/h2-5,17H,6H2,1H3

> <INCHI_KEY>
OYCTYROBRSPREE-UHFFFAOYSA-N

> <FORMULA>
C15H10O6

> <MOLECULAR_WEIGHT>
286.239

> <EXACT_MASS>
286.047738042

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
27.29667065330779

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{8-hydroxy-4,9-dioxo-4H,9H-naphtho[2,3-c]furan-1-yl}methyl acetate

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
1.9991630399999996

> <ALOGPS_LOGS>
-2.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.177865681398307

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1928939768191325

> <JCHEM_POLAR_SURFACE_AREA>
93.81

> <JCHEM_REFRACTIVITY>
71.4902

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.18e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate

> <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      -0.505  -8.428   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.001  -8.108   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.032  -9.253   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.477  -6.644   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.983  -6.323   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.459  -4.859   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.554  -3.613   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.459  -2.367   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.258  -0.533   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.591  -2.843   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.925  -2.073   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.259  -2.843   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.259  -4.383   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.925  -5.153   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.925  -6.693   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.591  -4.383   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.258  -5.153   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.258  -6.693   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.924  -4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   21                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   12   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    6    9                                                  
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

View in JSmol

Synonyms

Value	Source
{8-hydroxy-4,9-dioxo-4H,9H-naphtho[2,3-c]furan-1-yl}methyl acetic acid	Generator

Chemical Formula

C₁₅H₁₀O₆

Average Mass

286.2390 Da

Monoisotopic Mass

286.04774 Da

IUPAC Name

{8-hydroxy-4,9-dioxo-4H,9H-naphtho[2,3-c]furan-1-yl}methyl acetate

Traditional Name

{8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC1=C2C(=CO1)C(=O)C1=CC=CC(O)=C1C2=O

InChI Identifier

InChI=1S/C15H10O6/c1-7(16)20-6-11-13-9(5-21-11)14(18)8-3-2-4-10(17)12(8)15(13)19/h2-5,17H,6H2,1H3

InChI Key

OYCTYROBRSPREE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four 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

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Naphthalene
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Furan
Heteroaromatic compound
Vinylogous acid
Carboxylic acid ester
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
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	2.55	ALOGPS
logP	2	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.18	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	93.81 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.49 m³·mol⁻¹	ChemAxon
Polarizability	27.3 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

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

10401719

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate (NP0234802)

MOL for NP0234802 ({8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate)

3D MOL for NP0234802 ({8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate)

3D SDF for NP0234802 ({8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate)

3D-SDF for NP0234802 ({8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate)

PDB for NP0234802 ({8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate)

3D PDB for NP0234802 ({8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate)

SMILES for NP0234802 ({8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate)

INCHI for NP0234802 ({8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate)

Structure for NP0234802 ({8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate)

3D Structure for NP0234802 ({8-hydroxy-4,9-dioxonaphtho[2,3-c]furan-1-yl}methyl acetate)