NP-MRD: Showing NP-Card for 5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione (NP0244431)

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Record Information

Version

2.0

Created at

2022-09-07 05:13:49 UTC

Updated at

2022-09-07 05:13:49 UTC

NP-MRD ID

NP0244431

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione

Description

5-Hydroxy-7-methyl-1,2,3,4-tetrahydronaphthalene-1,4-dione belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione is found in Diospyros blancoi, Diospyros hebecarpa, Diospyros kaki, Diospyros virginiana, Euclea divinorum, Euclea natalensis and Nepenthes gracilis. 5-Hydroxy-7-methyl-1,2,3,4-tetrahydronaphthalene-1,4-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004191519142D          

 14 15  0  0  0  0            999 V2000
    0.0000   -1.6500    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
    0.7145   -0.4125    0.0000 C   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
    2.8579    0.8250    0.0000 O   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
    2.8579   -2.4750    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  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
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  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
  6 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244431

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=O)CCC(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H10O3/c1-6-4-7-8(12)2-3-9(13)11(7)10(14)5-6/h4-5,14H,2-3H2,1H3

> <INCHI_KEY>
KZQCBBYGLMOAMI-UHFFFAOYSA-N

> <FORMULA>
C11H10O3

> <MOLECULAR_WEIGHT>
190.198

> <EXACT_MASS>
190.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
19.359558534884272

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-7-methyl-1,2,3,4-tetrahydronaphthalene-1,4-dione

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.9966053823333332

> <ALOGPS_LOGS>
-1.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.829184226420438

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.349793454329197

> <JCHEM_PKA_STRONGEST_BASIC>
-5.629244370209073

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
52.1353

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.55e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -3.080   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   13                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14                                                  
CONECT   14   13    2                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₀O₃

Average Mass

190.1980 Da

Monoisotopic Mass

190.06299 Da

IUPAC Name

5-hydroxy-7-methyl-1,2,3,4-tetrahydronaphthalene-1,4-dione

Traditional Name

5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)CCC(=O)C2=C1

InChI Identifier

InChI=1S/C11H10O3/c1-6-4-7-8(12)2-3-9(13)11(7)10(14)5-6/h4-5,14H,2-3H2,1H3

InChI Key

KZQCBBYGLMOAMI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Diospyros blancoi	LOTUS Database	35616633
Diospyros hebecarpa	LOTUS Database	35616633
Diospyros kaki	LOTUS Database	35616633
Diospyros virginiana	LOTUS Database	35616633
Euclea divinorum	LOTUS Database	35616633
Euclea natalensis	LOTUS Database	35616633
Nepenthes gracilis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone).

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Naphthoquinone
Tetralin
Aryl alkyl ketone
Aryl ketone
Quinone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	1.83	ALOGPS
logP	2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	8.35	ChemAxon
pKa (Strongest Basic)	-5.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	52.14 m³·mol⁻¹	ChemAxon
Polarizability	19.36 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

16072923

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione (NP0244431)

MOL for NP0244431 (5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione)

3D MOL for NP0244431 (5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione)

3D SDF for NP0244431 (5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione)

3D-SDF for NP0244431 (5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione)

PDB for NP0244431 (5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione)

3D PDB for NP0244431 (5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione)

SMILES for NP0244431 (5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione)

INCHI for NP0244431 (5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione)

Structure for NP0244431 (5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione)

3D Structure for NP0244431 (5-hydroxy-7-methyl-2,3-dihydronaphthalene-1,4-dione)