Jump To Section:

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 00:53:34 UTC

Update Date

2023-02-21 17:29:52 UTC

HMDB ID

HMDB0060322

Secondary Accession Numbers

HMDB60322

Metabolite Identification

Common Name

1-Hydroxymethylnaphthalene

Description

1-Hydroxymethylnaphthalene, also known as 1-naphthalenemethanol or 1-menaphthyl alcohol, 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-Hydroxymethylnaphthalene is an extremely weak basic (essentially neutral) compound (based on its pKa). 1-Hydroxymethylnaphthalene exists in all living organisms, ranging from bacteria to humans. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Structure #1                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   1.540   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   3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   2.310   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  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    2    4                                                       
CONECT    2    1    7                                                       
CONECT    3    5    6                                                       
CONECT    4    1    9                                                       
CONECT    5    3    9                                                       
CONECT    6    3   10                                                       
CONECT    7    2   11                                                       
CONECT    8   10   12                                                       
CONECT    9    4    5   11                                                  
CONECT   10    6    8   11                                                  
CONECT   11    7    9   10                                                  
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-Menaphthyl alcohol	ChEBI
1-Naphthalenemethanol	ChEBI
1-Naphthylmethyl alcohol	ChEBI
Naphthalene-1-methanol	ChEBI
1-Naphthylmethanol	MeSH

Chemical Formula

C₁₁H₁₀O

Average Molecular Weight

158.1965

Monoisotopic Molecular Weight

158.073164942

IUPAC Name

naphthalen-1-ylmethanol

Traditional Name

1-naphthalenemethanol

CAS Registry Number

Not Available

SMILES

OCC1=CC=CC2=CC=CC=C12

InChI Identifier

InChI=1S/C11H10O/c12-8-10-6-3-5-9-4-1-2-7-11(9)10/h1-7,12H,8H2

InChI Key

PBLNHHSDYFYZNC-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
Organic oxygen compound
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthylmethanol (CHEBI:38137 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0060322)

Source

Exogenous

Exogenous (HMDB: HMDB0060322)

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	0.34 g/L	ALOGPS
logP	2.17	ALOGPS
logP	2.2	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	15.14	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	49.32 m³·mol⁻¹	ChemAxon
Polarizability	17.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	133.527	31661259
DarkChem	[M-H]-	131.545	31661259
DeepCCS	[M-2H]-	165.901	30932474
DeepCCS	[M+Na]+	141.294	30932474
AllCCS	[M+H]+	133.1	32859911
AllCCS	[M+H-H2O]+	128.5	32859911
AllCCS	[M+NH4]+	137.4	32859911
AllCCS	[M+Na]+	138.7	32859911
AllCCS	[M-H]-	133.4	32859911
AllCCS	[M+Na-2H]-	134.0	32859911
AllCCS	[M+HCOO]-	134.7	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 × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.89 minutes	32390414
Predicted by Siyang on May 30, 2022	13.958 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.58 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1-Hydroxymethylnaphthalene	OCC1=CC=CC2=CC=CC=C12	2574.8	Standard polar	33892256
1-Hydroxymethylnaphthalene	OCC1=CC=CC2=CC=CC=C12	1527.0	Standard non polar	33892256
1-Hydroxymethylnaphthalene	OCC1=CC=CC2=CC=CC=C12	1544.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1-Hydroxymethylnaphthalene,1TMS,isomer #1	C[Si](C)(C)OCC1=CC=CC2=CC=CC=C12	1636.9	Semi standard non polar	33892256
1-Hydroxymethylnaphthalene,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OCC1=CC=CC2=CC=CC=C12	1880.0	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-Hydroxymethylnaphthalene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-0900000000-caddae6141d4e9690170	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Hydroxymethylnaphthalene GC-MS (1 TMS) - 70eV, Positive	splash10-00dl-9840000000-b9db038f92c50a124270	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Hydroxymethylnaphthalene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1-Hydroxymethylnaphthalene 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 - 1-Hydroxymethylnaphthalene 10V, Positive-QTOF	splash10-0a4l-0900000000-bfef4ef24e92db18639c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxymethylnaphthalene 20V, Positive-QTOF	splash10-0006-0900000000-431cdda2ca3dfe4380f3	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxymethylnaphthalene 40V, Positive-QTOF	splash10-0006-1900000000-dd261bb129c3b52fa1c2	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxymethylnaphthalene 10V, Negative-QTOF	splash10-0a4i-0900000000-ca46d48ce67138a3e23f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxymethylnaphthalene 20V, Negative-QTOF	splash10-0a6r-0900000000-b57dbcfed0ed22e54a0f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxymethylnaphthalene 40V, Negative-QTOF	splash10-004i-0900000000-9248ee6ce8913e6a4a2c	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxymethylnaphthalene 10V, Positive-QTOF	splash10-0006-0900000000-da91f5f56d18f8981e9a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxymethylnaphthalene 20V, Positive-QTOF	splash10-0006-0900000000-bcc6eab2c454b5185760	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxymethylnaphthalene 40V, Positive-QTOF	splash10-004l-2900000000-10a862aca2e180e31976	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxymethylnaphthalene 10V, Negative-QTOF	splash10-056r-0900000000-d5b95fd826831404fdf6	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxymethylnaphthalene 20V, Negative-QTOF	splash10-004i-0900000000-fc2d9e3172581fde784a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1-Hydroxymethylnaphthalene 40V, Negative-QTOF	splash10-056r-0900000000-bbda57da86b43bb5a370	2021-10-12	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	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+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

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C14089

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20908

PDB ID

Not Available

ChEBI ID

38137

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. Alcohol dehydrogenase class-3

General function:: Involved in zinc ion binding
Specific function:: Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:: ADH5
Uniprot ID:: P11766
Molecular weight:: 39723.945

Reactions

1-Hydroxymethylnaphthalene + NAD → 1-Naphthaldehyde + NADH + Hydrogen Ion	details

Showing metabocard for 1-Hydroxymethylnaphthalene (HMDB0060322)

MOL for HMDB0060322 (1-Hydroxymethylnaphthalene)

3D MOL for HMDB0060322 (1-Hydroxymethylnaphthalene)

3D SDF for HMDB0060322 (1-Hydroxymethylnaphthalene)

3D-SDF for HMDB0060322 (1-Hydroxymethylnaphthalene)

PDB for HMDB0060322 (1-Hydroxymethylnaphthalene)

3D PDB for HMDB0060322 (1-Hydroxymethylnaphthalene)

SMILES for HMDB0060322 (1-Hydroxymethylnaphthalene)

INCHI for HMDB0060322 (1-Hydroxymethylnaphthalene)

Structure for HMDB0060322 (1-Hydroxymethylnaphthalene)

3D Structure for HMDB0060322 (1-Hydroxymethylnaphthalene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra

Enzymes

Reactions