NP-MRD: Showing NP-Card for 1,3,6,8-Tetrahydroxynaphthalene (NP0050397)

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Record Information

Version

2.0

Created at

2022-04-27 20:57:12 UTC

Updated at

2022-04-27 20:57:12 UTC

NP-MRD ID

NP0050397

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,3,6,8-Tetrahydroxynaphthalene

Description

Naphthalene-1,3,6,8-tetrol, also known as 1,3,6,8-tetrahydroxynaphthalene or 1,3,6,8-naphthalenetetrol, belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position. A naphthalenetetrol that is naphthalene substituted by hydroxy groups at positions 1, 3, 6 and 8. 1,3,6,8-Tetrahydroxynaphthalene is found in Aspergillus oryzae, Colletotrichum lagenarium, Glarea lozoyensis and Streptomyces griseus. Naphthalene-1,3,6,8-tetrol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 04121516572D          

 14 15  0  0  0  0            999 V2000
    0.0000   -1.6500    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
    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
    4.2868   -1.6500    0.0000 O   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
    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  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 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>
NP0050397

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=CC(O)=CC(O)=C2C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H8O4/c11-6-1-5-2-7(12)4-9(14)10(5)8(13)3-6/h1-4,11-14H

> <INCHI_KEY>
BCMKHWMDTMUUSI-UHFFFAOYSA-N

> <FORMULA>
C10H8O4

> <MOLECULAR_WEIGHT>
192.17

> <EXACT_MASS>
192.042258738

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
18.320100794244667

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
naphthalene-1,3,6,8-tetrol

> <ALOGPS_LOGP>
0.93

> <JCHEM_LOGP>
1.748461286

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.238521261583015

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.454563111837603

> <JCHEM_PKA_STRONGEST_BASIC>
-5.6854681183085

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
50.431799999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.60e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,3,6,8-naphthalenetetrol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+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  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+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   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12    6   14                                                  
CONECT   14   13    2                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
1,3,6,8-Naphthalenetetrol	ChEBI
1,3,6,8-Tetrahydroxynaphthalene	ChEBI

Chemical Formula

C₁₀H₈O₄

Average Mass

192.1700 Da

Monoisotopic Mass

192.04226 Da

IUPAC Name

naphthalene-1,3,6,8-tetrol

Traditional Name

1,3,6,8-naphthalenetetrol

CAS Registry Number

Not Available

SMILES

OC1=CC2=CC(O)=CC(O)=C2C(O)=C1

InChI Identifier

InChI=1S/C10H8O4/c11-6-1-5-2-7(12)4-9(14)10(5)8(13)3-6/h1-4,11-14H

InChI Key

BCMKHWMDTMUUSI-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Aspergillus oryzae	LOTUS Database	35616633
Colletotrichum lagenarium	Fungi	KNApSAcK
Glarea lozoyensis	LOTUS Database	35616633
Streptomyces griseus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthols and derivatives. These are naphthalene derivatives carrying one or more hydroxyl (-OH) groups at any ring position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Naphthols and derivatives

Direct Parent

Naphthols and derivatives

Alternative Parents

Substituents

1-naphthol
2-naphthol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthalenetetrol (CHEBI:18365 )
an aromatic compound (TETRAHYD-CPD )

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	0.93	ALOGPS
logP	1.75	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	8.45	ChemAxon
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	50.43 m³·mol⁻¹	ChemAxon
Polarizability	18.32 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

C00000548

Chemspider ID

Not Available

KEGG Compound ID

C04033

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

440202

PDB ID

Not Available

ChEBI ID

18365

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 1,3,6,8-Tetrahydroxynaphthalene (NP0050397)

MOL for NP0050397 (1,3,6,8-Tetrahydroxynaphthalene)

3D MOL for NP0050397 (1,3,6,8-Tetrahydroxynaphthalene)

3D SDF for NP0050397 (1,3,6,8-Tetrahydroxynaphthalene)

3D-SDF for NP0050397 (1,3,6,8-Tetrahydroxynaphthalene)

PDB for NP0050397 (1,3,6,8-Tetrahydroxynaphthalene)

3D PDB for NP0050397 (1,3,6,8-Tetrahydroxynaphthalene)

SMILES for NP0050397 (1,3,6,8-Tetrahydroxynaphthalene)

INCHI for NP0050397 (1,3,6,8-Tetrahydroxynaphthalene)

Structure for NP0050397 (1,3,6,8-Tetrahydroxynaphthalene)

3D Structure for NP0050397 (1,3,6,8-Tetrahydroxynaphthalene)