NP-MRD: Showing NP-Card for 4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one (NP0299233)

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Record Information

Version

2.0

Created at

2022-09-10 10:56:36 UTC

Updated at

2022-09-10 10:56:37 UTC

NP-MRD ID

NP0299233

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one

Description

4,5,8-Trihydroxy-6-methoxy-3-(2-oxopropyl)-1,2,3,4-tetrahydronaphthalen-1-one belongs to the class of organic compounds known as tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane. Based on a literature review very few articles have been published on 4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-1,2,3,4-tetrahydronaphthalen-1-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309102212562D          

 20 21  0  0  0  0            999 V2000
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   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
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   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
    0.7145   -0.4125    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
    0.0000    0.8250    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   -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
    3.5724   -0.4125    0.0000 C   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   -1.2375    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
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  3  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
  7 19  1  0  0  0  0
 19 20  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0299233

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)CC(CC(C)=O)C(O)C2=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O6/c1-6(15)3-7-4-8(16)11-9(17)5-10(20-2)14(19)12(11)13(7)18/h5,7,13,17-19H,3-4H2,1-2H3

> <INCHI_KEY>
DFKLLVDXSVLRDE-UHFFFAOYSA-N

> <FORMULA>
C14H16O6

> <MOLECULAR_WEIGHT>
280.276

> <EXACT_MASS>
280.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.87375131076164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-1,2,3,4-tetrahydronaphthalen-1-one

> <JCHEM_LOGP>
0.7544369413333329

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.538047000628728

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.989770121999328

> <JCHEM_PKA_STRONGEST_BASIC>
-3.379312229229156

> <JCHEM_POLAR_SURFACE_AREA>
104.06

> <JCHEM_REFRACTIVITY>
70.5563

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2H-naphthalen-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   19                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13   19                                                       
CONECT   19   18    7   20                                                  
CONECT   20   19                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₄H₁₆O₆

Average Mass

280.2760 Da

Monoisotopic Mass

280.09469 Da

IUPAC Name

4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-1,2,3,4-tetrahydronaphthalen-1-one

Traditional Name

4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2H-naphthalen-1-one

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)CC(CC(C)=O)C(O)C2=C1O

InChI Identifier

InChI=1S/C14H16O6/c1-6(15)3-7-4-8(16)11-9(17)5-10(20-2)14(19)12(11)13(7)18/h5,7,13,17-19H,3-4H2,1-2H3

InChI Key

DFKLLVDXSVLRDE-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 tetralins. These are polycyclic aromatic compounds containing a tetralin moiety, which consists of a benzene fused to a cyclohexane.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Tetralins

Sub Class

Not Available

Direct Parent

Tetralins

Alternative Parents

Substituents

Tetralin
Anisole
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Vinylogous acid
Ketone
Secondary alcohol
Polyol
Ether
Organooxygen compound
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	0.75	ChemAxon
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	70.56 m³·mol⁻¹	ChemAxon
Polarizability	27.87 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

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162868573

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one (NP0299233)

MOL for NP0299233 (4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

3D MOL for NP0299233 (4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

3D SDF for NP0299233 (4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

3D-SDF for NP0299233 (4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

PDB for NP0299233 (4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

3D PDB for NP0299233 (4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

SMILES for NP0299233 (4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

INCHI for NP0299233 (4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

Structure for NP0299233 (4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)

3D Structure for NP0299233 (4,5,8-trihydroxy-6-methoxy-3-(2-oxopropyl)-3,4-dihydro-2h-naphthalen-1-one)