MiMeDB: Showing metabocard for naphthalene-1,3,6,8-tetrol (MMDBc0054603)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-05 23:20:43 UTC

Update Date

2025-10-07 16:08:35 UTC

Metabolite ID

MMDBc0054603

Metabolite Identification

Common Name

naphthalene-1,3,6,8-tetrol

Description

naphthalene-1,3,6,8-tetrol is a polycyclic aromatic hydrocarbon derivative. There is little literature available on this metabolite, indicating a gap in research regarding its biological significance and potential applications.

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>
MMDBc0054603

> <DATABASE_NAME>
MIME

> <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

Synonyms

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

Molecular Formula

C₁₀H₈O₄

Average Mass

192.17

Monoisotopic Mass

192.042258738

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

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.6 g/L	ALOGPS
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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-24	315.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	42.4
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	354.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	507.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	620.6
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-24	408.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	1764.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	488.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	719.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	233.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	392.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	231.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	98.7
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	344.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	840.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	463.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	464.9
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	1511.6
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	848.0

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_1	C[Si](C)(C)OC1=CC(O)=C2C(O)=CC(O)=CC2=C1	standard non polar	2025-10-24	1427.81
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_2	C[Si](C)(C)OC1=CC(O)=CC2=CC(O)=CC(O)=C12	standard non polar	2025-10-24	1772.42
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(O)=CC(O)=CC2=C1	standard non polar	2025-10-24	1968.44
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_4	C[Si](C)(C)OC1=CC(O)=C2C(O[Si](C)(C)C)=CC(O)=CC2=C1	standard non polar	2025-10-24	1796.64
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_5	C[Si](C)(C)OC1=CC(O)=C2C(O)=CC(O[Si](C)(C)C)=CC2=C1	standard non polar	2025-10-24	2077.06
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_6	C[Si](C)(C)OC1=CC(O)=CC2=CC(O)=CC(O[Si](C)(C)C)=C12	standard non polar	2025-10-24	1982.97
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_7	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(O[Si](C)(C)C)=CC(O)=CC2=C1	standard non polar	2025-10-24	1476.17
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_8	C[Si](C)(C)OC1=CC(O)=C2C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=CC2=C1	standard non polar	2025-10-24	1897.05
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_9	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=CC2=C1	standard non polar	2025-10-24	2826.85
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_1	C[Si](C)(C)OC1=CC(O)=C2C(O)=CC(O)=CC2=C1	standard polar	2025-10-24	2086.0
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_2	C[Si](C)(C)OC1=CC(O)=CC2=CC(O)=CC(O)=C12	standard polar	2025-10-24	2264.31
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_3	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(O)=CC(O)=CC2=C1	standard polar	2025-10-24	1402.01
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_4	C[Si](C)(C)OC1=CC(O)=C2C(O[Si](C)(C)C)=CC(O)=CC2=C1	standard polar	2025-10-24	2150.96
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_5	C[Si](C)(C)OC1=CC(O)=C2C(O)=CC(O[Si](C)(C)C)=CC2=C1	standard polar	2025-10-24	2320.74
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_6	C[Si](C)(C)OC1=CC(O)=CC2=CC(O)=CC(O[Si](C)(C)C)=C12	standard polar	2025-10-24	2313.27
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_7	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(O[Si](C)(C)C)=CC(O)=CC2=C1	standard polar	2025-10-24	1729.21
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_8	C[Si](C)(C)OC1=CC(O)=C2C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=CC2=C1	standard polar	2025-10-24	1880.82
Gas Chromatography	naphthalene-1,3,6,8-tetrol_TMS_9	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(O[Si](C)(C)C)=CC(O[Si](C)(C)C)=CC2=C1	standard polar	2025-10-24	2455.91

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species
Eukaryota/Fungi	Ascomycota	4
Bacteria	Actinobacteria	1
Bacteria/Eubacteria	Actinobacteria	2

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for naphthalene-1,3,6,8-tetrol (MMDBc0054603)

MOL for #<Metabolite:0x00007f9ac424cc80>

3D MOL for #<Metabolite:0x00007f9ac424cc80>

3D SDF for #<Metabolite:0x00007f9ac424cc80>

3D-SDF for #<Metabolite:0x00007f9ac424cc80>

PDB for #<Metabolite:0x00007f9ac424cc80>

3D PDB for #<Metabolite:0x00007f9ac424cc80>

SMILES for #<Metabolite:0x00007f9ac424cc80>

INCHI for #<Metabolite:0x00007f9ac424cc80>

Structure for #<Metabolite:0x00007f9ac424cc80>

3D Structure for #<Metabolite:0x00007f9ac424cc80>