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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-05-17 00:54:31 UTC

Update Date

2022-03-07 03:17:43 UTC

HMDB ID

HMDB0060335

Secondary Accession Numbers

HMDB60335

Metabolite Identification

Common Name

1,2-Dihydronaphthalene-1,2-diol

Description

1,2-Dihydronaphthalene-1,2-diol, also known as 1,2-dihydroxy-1,2-dihydronaphthalene or naphthalene-1,2-dihydrodiol, belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings. 1,2-Dihydronaphthalene-1,2-diol exists in all living organisms, ranging from bacteria to humans. 1,2-Dihydronaphthalene-1,2-diol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 1,2-Dihydronaphthalene-1,2-diol.

Structure

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

HEADER    PROTEIN                                 16-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+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   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    7                                                       
CONECT    6    5    9                                                       
CONECT    7    3    5    8                                                  
CONECT    8    4    7   10                                                  
CONECT    9    6   10   11                                                  
CONECT   10    8    9   12                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
1,2-Dihydroxy-1,2-dihydronaphthalene	ChEBI
1,2-Dihydroxy-1,2-dihydronaphthalene, (cis)-(+-)-isomer	HMDB
Naphthalene-1,2-dihydrodiol	HMDB
trans-1,2-Dihydroxy-1,2-dihydronaphthalene	HMDB
1,2-Dihydroxy-1,2-dihydronaphthalene, (1S-trans)-isomer	HMDB
1,2-Dihydroxy-1,2-dihydronaphthalene, (cis)-isomer	HMDB
1,2-Dihydroxy-1,2-dihydronaphthalene, (trans)-isomer	HMDB
1,2-Dihydroxy-1,2-dihydronaphthalene, (trans)-(+-)-isomer	HMDB
1,2-Dihydroxy-1,2-dihydronaphthalene, (trans)-(-)-isomer	HMDB

Chemical Formula

C₁₀H₁₀O₂

Average Molecular Weight

162.1852

Monoisotopic Molecular Weight

162.068079564

IUPAC Name

1,2-dihydronaphthalene-1,2-diol

Traditional Name

naphthalene-1,2-dihydrodiol

CAS Registry Number

Not Available

SMILES

OC1C=CC2=CC=CC=C2C1O

InChI Identifier

InChI=1S/C10H10O2/c11-9-6-5-7-3-1-2-4-8(7)10(9)12/h1-6,9-12H

InChI Key

QPUHWUSUBHNZCG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Naphthalenes

Sub Class

Not Available

Direct Parent

Naphthalenes

Alternative Parents

Substituents

Naphthalene
Secondary alcohol
1,2-diol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthalenediols (CHEBI:28516 )
a small molecule (CIS-12-DIHYDRONAPHTHALENE-12-DIOL )

Ontology

Not Available

Exogenous (HMDB: HMDB0060335)

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	22.5 g/L	ALOGPS
logP	0.63	ALOGPS
logP	1	ChemAxon
logS	-0.86	ALOGPS
pKa (Strongest Acidic)	13.2	ChemAxon
pKa (Strongest Basic)	-3.4	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	47.38 m³·mol⁻¹	ChemAxon
Polarizability	16.84 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]+	136.233	31661259
DarkChem	[M-H]-	130.011	31661259
DeepCCS	[M+H]+	131.81	30932474
DeepCCS	[M-H]-	129.154	30932474
DeepCCS	[M-2H]-	165.712	30932474
DeepCCS	[M+Na]+	140.884	30932474
AllCCS	[M+H]+	136.9	32859911
AllCCS	[M+H-H2O]+	132.3	32859911
AllCCS	[M+NH4]+	141.2	32859911
AllCCS	[M+Na]+	142.4	32859911
AllCCS	[M-H]-	134.4	32859911
AllCCS	[M+Na-2H]-	135.0	32859911
AllCCS	[M+HCOO]-	135.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	3.95 minutes	32390414
Predicted by Siyang on May 30, 2022	9.7751 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.19 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2-Dihydronaphthalene-1,2-diol	OC1C=CC2=CC=CC=C2C1O	2805.0	Standard polar	33892256
1,2-Dihydronaphthalene-1,2-diol	OC1C=CC2=CC=CC=C2C1O	1572.9	Standard non polar	33892256
1,2-Dihydronaphthalene-1,2-diol	OC1C=CC2=CC=CC=C2C1O	1597.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,2-Dihydronaphthalene-1,2-diol,1TMS,isomer #1	C[Si](C)(C)OC1C=CC2=CC=CC=C2C1O	1615.5	Semi standard non polar	33892256
1,2-Dihydronaphthalene-1,2-diol,1TMS,isomer #2	C[Si](C)(C)OC1C2=CC=CC=C2C=CC1O	1587.8	Semi standard non polar	33892256
1,2-Dihydronaphthalene-1,2-diol,2TMS,isomer #1	C[Si](C)(C)OC1C=CC2=CC=CC=C2C1O[Si](C)(C)C	1621.1	Semi standard non polar	33892256
1,2-Dihydronaphthalene-1,2-diol,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC2=CC=CC=C2C1O	1864.5	Semi standard non polar	33892256
1,2-Dihydronaphthalene-1,2-diol,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C2=CC=CC=C2C=CC1O	1837.6	Semi standard non polar	33892256
1,2-Dihydronaphthalene-1,2-diol,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C=CC2=CC=CC=C2C1O[Si](C)(C)C(C)(C)C	2097.7	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 - 1,2-Dihydronaphthalene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fsi-0900000000-30816753a4b47bb8c7ca	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (2 TMS) - 70eV, Positive	splash10-00y3-7390000000-d91f46a72c7b1bdbc652	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-03	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 - 1,2-Dihydronaphthalene-1,2-diol 10V, Positive-QTOF	splash10-03di-0900000000-1d76de306a4e3266c712	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol 20V, Positive-QTOF	splash10-03e9-0900000000-d41bfc0f04e29afcef50	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol 40V, Positive-QTOF	splash10-0f6x-9500000000-e72884c251ba66205492	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol 10V, Negative-QTOF	splash10-03di-0900000000-b294d622ce5e72f2bc99	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol 20V, Negative-QTOF	splash10-03di-0900000000-368dc2351487ced1da90	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2-Dihydronaphthalene-1,2-diol 40V, Negative-QTOF	splash10-0w4l-1900000000-f0e470bae4e954754801	2017-10-06	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

355

KEGG Compound ID

C06205

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

362

PDB ID

Not Available

ChEBI ID

28516

Food Biomarker Ontology

Not Available

VMH ID

Not Available

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 ]

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

Enzyme Details

2. Epoxide hydrolase 1

General function:: Involved in catalytic activity
Specific function:: Biotransformation enzyme that catalyzes the hydrolysis of arene and aliphatic epoxides to less reactive and more water soluble dihydrodiols by the trans addition of water.
Gene Name:: EPHX1
Uniprot ID:: P07099
Molecular weight:: 52948.48

Reactions

Naphthalene epoxide + Water → 1,2-Dihydronaphthalene-1,2-diol	details
(1S,2R)-Naphthalene 1,2-oxide + Water → 1,2-Dihydronaphthalene-1,2-diol	details

Showing metabocard for 1,2-Dihydronaphthalene-1,2-diol (HMDB0060335)

MOL for HMDB0060335 (1,2-Dihydronaphthalene-1,2-diol)

3D MOL for HMDB0060335 (1,2-Dihydronaphthalene-1,2-diol)

3D SDF for HMDB0060335 (1,2-Dihydronaphthalene-1,2-diol)

3D-SDF for HMDB0060335 (1,2-Dihydronaphthalene-1,2-diol)

PDB for HMDB0060335 (1,2-Dihydronaphthalene-1,2-diol)

3D PDB for HMDB0060335 (1,2-Dihydronaphthalene-1,2-diol)

SMILES for HMDB0060335 (1,2-Dihydronaphthalene-1,2-diol)

INCHI for HMDB0060335 (1,2-Dihydronaphthalene-1,2-diol)

Structure for HMDB0060335 (1,2-Dihydronaphthalene-1,2-diol)

3D Structure for HMDB0060335 (1,2-Dihydronaphthalene-1,2-diol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

Reactions

Reactions