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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 01:25:04 UTC

Update Date

2023-02-21 17:30:03 UTC

HMDB ID

HMDB0060497

Secondary Accession Numbers

HMDB60497

Metabolite Identification

Common Name

Naphthalene-1,2-diol

Description

Naphthalene-1,2-diol, also known as 1,2-naphthalenediol or 1,2-naphthohydroquinone, 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. Naphthalene-1,2-diol is an extremely weak basic (essentially neutral) compound (based on its pKa). Naphthalene-1,2-diol exists in all living organisms, ranging from bacteria to humans. These are hydroxylated naphthalenes.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: D1N                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.694  -1.972   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.360  -2.742   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.360  -4.282   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.973  -5.052   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.307  -4.282   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.307  -2.742   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.973  -1.972   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.973  -0.432   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.641  -1.972   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.974  -2.742   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.974  -4.282   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.641  -5.052   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7    9                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12    5   11                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Dihydroxynaphthalene	ChEBI
1,2-Naphthalenediol	ChEBI
1,2-Naphthohydroquinone	ChEBI
beta-Naphthohydroquinone	ChEBI
b-Naphthohydroquinone	Generator
Β-naphthohydroquinone	Generator
1,2-Dihydroxynaphthalene monohydrate	HMDB

Chemical Formula

C₁₀H₈O₂

Average Molecular Weight

160.1693

Monoisotopic Molecular Weight

160.0524295

IUPAC Name

naphthalene-1,2-diol

Traditional Name

1,2-dihydroxynaphthalene

CAS Registry Number

Not Available

SMILES

OC1=CC=C2C=CC=CC2=C1O

InChI Identifier

InChI=1S/C10H8O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,11-12H

InChI Key

NXPPAOGUKPJVDI-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
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthalenediol (CHEBI:17435 )
a small molecule (NAPHTHALENE-12-DIOL )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060497)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.71 g/L	ALOGPS
logP	2.06	ALOGPS
logP	2.36	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.04	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	46.47 m³·mol⁻¹	ChemAxon
Polarizability	16.4 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.321	31661259
DarkChem	[M-H]-	130.891	31661259
DeepCCS	[M+H]+	130.697	30932474
DeepCCS	[M-H]-	128.144	30932474
DeepCCS	[M-2H]-	164.281	30932474
DeepCCS	[M+Na]+	139.34	30932474
AllCCS	[M+H]+	133.3	32859911
AllCCS	[M+H-H2O]+	128.6	32859911
AllCCS	[M+NH4]+	137.6	32859911
AllCCS	[M+Na]+	138.9	32859911
AllCCS	[M-H]-	131.1	32859911
AllCCS	[M+Na-2H]-	131.6	32859911
AllCCS	[M+HCOO]-	132.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Naphthalene-1,2-diol	OC1=CC=C2C=CC=CC2=C1O	3045.4	Standard polar	33892256
Naphthalene-1,2-diol	OC1=CC=C2C=CC=CC2=C1O	1593.7	Standard non polar	33892256
Naphthalene-1,2-diol	OC1=CC=C2C=CC=CC2=C1O	1734.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Naphthalene-1,2-diol,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C=CC=CC2=C1O	1745.9	Semi standard non polar	33892256
Naphthalene-1,2-diol,1TMS,isomer #2	C[Si](C)(C)OC1=C(O)C=CC2=CC=CC=C12	1729.6	Semi standard non polar	33892256
Naphthalene-1,2-diol,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C2C=CC=CC2=C1O[Si](C)(C)C	1773.1	Semi standard non polar	33892256
Naphthalene-1,2-diol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC=CC2=C1O	1995.1	Semi standard non polar	33892256
Naphthalene-1,2-diol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=C(O)C=CC2=CC=CC=C12	1986.5	Semi standard non polar	33892256
Naphthalene-1,2-diol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C2C=CC=CC2=C1O[Si](C)(C)C(C)(C)C	2288.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Naphthalene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	splash10-01q9-0900000000-0f956a12d0643c144a3c	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naphthalene-1,2-diol GC-MS (2 TMS) - 70eV, Positive	splash10-0fl9-4290000000-a8b5d5f699983fa20c23	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Naphthalene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthalene-1,2-diol 10V, Positive-QTOF	splash10-03di-0900000000-43ad7fe3948f81593f24	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthalene-1,2-diol 20V, Positive-QTOF	splash10-03di-0900000000-3f891b94d5d45e2c9ae1	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthalene-1,2-diol 40V, Positive-QTOF	splash10-0udl-3900000000-4f2b9a1e61aa434bea1b	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthalene-1,2-diol 10V, Negative-QTOF	splash10-0a4i-0900000000-4f24626a6d139a7f3bac	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthalene-1,2-diol 20V, Negative-QTOF	splash10-0a4i-0900000000-738df9d80c446d325a10	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Naphthalene-1,2-diol 40V, Negative-QTOF	splash10-0pb9-1900000000-a2f5a34fc929cd184790	2017-07-26	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB07610

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C03012

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11318

PDB ID

Not Available

ChEBI ID

17435

Food Biomarker Ontology

Not Available

VMH ID

12NPTHLDL

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Magrane M: UniProt Knowledgebase: a hub of integrated protein data. Database (Oxford). 2011 Mar 29;2011:bar009. doi: 10.1093/database/bar009. Print 2011. [PubMed:21447597 ]
Brunk E, Sahoo S, Zielinski DC, Altunkaya A, Drager A, Mih N, Gatto F, Nilsson A, Preciat Gonzalez GA, Aurich MK, Prlic A, Sastry A, Danielsdottir AD, Heinken A, Noronha A, Rose PW, Burley SK, Fleming RMT, Nielsen J, Thiele I, Palsson BO: Recon3D enables a three-dimensional view of gene variation in human metabolism. Nat Biotechnol. 2018 Mar;36(3):272-281. doi: 10.1038/nbt.4072. Epub 2018 Feb 19. [PubMed:29457794 ]

Enzymes

Enzyme Details

1. Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase

General function:: Involved in catalytic activity
Specific function:: Not Available
Gene Name:: DHDH
Uniprot ID:: Q9UQ10
Molecular weight:: 36381.705

Reactions

1,2-Dihydronaphthalene-1,2-diol + NADP → Naphthalene-1,2-diol + NADPH + Hydrogen Ion	details

Showing metabocard for Naphthalene-1,2-diol (HMDB0060497)

MOL for HMDB0060497 (Naphthalene-1,2-diol)

3D MOL for HMDB0060497 (Naphthalene-1,2-diol)

3D SDF for HMDB0060497 (Naphthalene-1,2-diol)

3D-SDF for HMDB0060497 (Naphthalene-1,2-diol)

PDB for HMDB0060497 (Naphthalene-1,2-diol)

3D PDB for HMDB0060497 (Naphthalene-1,2-diol)

SMILES for HMDB0060497 (Naphthalene-1,2-diol)

INCHI for HMDB0060497 (Naphthalene-1,2-diol)

Structure for HMDB0060497 (Naphthalene-1,2-diol)

3D Structure for HMDB0060497 (Naphthalene-1,2-diol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions