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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:52:19 UTC

Update Date

2023-02-21 17:22:41 UTC

HMDB ID

HMDB0032861

Secondary Accession Numbers

HMDB32861

Metabolite Identification

Common Name

2-Methoxynaphthalene

Description

Arabinogalactan is found in soy bean. Emulsifier, stabiliser Approximately one of the three arabinosyl chains attached to the galactan chain contains succinyl groups. Although one succinyl group is most common, up to three succinyl groups per released arabinan fragment can be found on oligo-arabinans. However, arabinan fragments substituted with GalNH2 are not succinylated. Importantly, in the case of M. tuberculosis, and most likely in all slow growers, both positive charge (protonated GalNH2 as GalNH3+) and negative charge (succinyl) are present in the middle regions of the arabinan, specifically at O-2 of the inner 3,5- -D-Araf units. The succinyl residues are on the non-mycolylated chain. Recently a complete primary model of arabinogalactan has been proposed. Arabinogalactan is a biopolymer consisting of arabinose and galactose monosaccharides. Two classes of arabinogalctans are found in nature: plant arabinogalactan and microbial arabinogalactan. In plants, it is a major constituents of many gums, including gum arabic, gum gutti and so on. It occasionally attached to proteins and the resulted proteoglycan functions as signaling molecules betweens cells as well as glue to seal wounded part of plants. The microbial arabinogalactan is a major structural component of the mycobacterial cell wall. Both the arabinose and galactose are solely in the furanose configuration. The galactan portion of the microbial arabinogalactan is linear, consisting of approximately 30 units with alternating -(1-5) and -(1-6) glycosidic linkages. The arabinan chain, which consist of about 30 residues, are attached at three branch points within the galactan chain (believed to be at residues 8, 10 and 12).The arabinan portion of the polymer is a complex branched structure, usually capped with mycolic acids. The arabinan glycosidic linkages are -(1-3), -(1-5), and -(1-2). The non-reducing end of arabinogalactan is covalently attached to the mycolic acids of the outer membrane. The hydrophobicity of mycolic acids is a barrier to drug entry. Additionally, the mycolyl arabinogalactan peptidiglycan is responsible for aspects of disease pathogenesis and much of the antibody response in infections. The mycolyl substituents are selectively and equally distributed on the 5-hydroxyl functions of terminal- and the penultimate 2-linked Araf residues. The mycolyl residues are clustered in groups of four on the non reducing terminal pentaarabinosyl unit ( -Araf-(1 2)- -Araf)2-3,5- -Araf. Thus, the major part (66%) of the pentaarabinosyl units are substituted by mycolic acids, leaving the unsubstituted minor region (33%), that is available for interaction with the immune system.

Structure

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

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       2.694   1.924   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.694   3.464   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.078  -2.694   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.308  -3.464   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.694  -2.694   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.694  -1.154   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.308  -0.384   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.308   1.154   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.078   1.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.308   1.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.308  -0.384   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.078  -1.154   0.000  0.00  0.00           C+0
CONECT    1    2   10                                                       
CONECT    2    1                                                            
CONECT    3    4   12                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    1    9   11                                                  
CONECT   11   10   12                                                       
CONECT   12    3    7   11                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2-Methoxy-naphthalene	ChEMBL, HMDB
2-Naphthol methyl ether	HMDB
2-Naphthyl methyl ether	HMDB
b-Naphthyl methyl ether	HMDB
beta -Methoxynaphthalene	HMDB
beta -Naphthol methyl ether	HMDB
beta -Naphthyl methyl ether	HMDB
beta-Methoxynaphthalene	HMDB
beta-Naphthol mether ether	HMDB
beta-Naphthol methyl ether	HMDB
beta-Naphthyl methyl ether	HMDB
Jara jara	HMDB
Methyl 2-naphthyl ether	HMDB
Methyl beta -naphthyl ether	HMDB
Methyl beta-naphthyl ether	HMDB
Nerolin	HMDB
Nerolin yara yara	HMDB
Yara yara	HMDB
Yara-yara	HMDB
Yura yara	HMDB

Chemical Formula

C₁₁H₁₀O

Average Molecular Weight

158.1965

Monoisotopic Molecular Weight

158.073164942

IUPAC Name

2-methoxynaphthalene

Traditional Name

naphthalene, 2-methoxy-

CAS Registry Number

93-04-9

SMILES

COC1=CC2=C(C=CC=C2)C=C1

InChI Identifier

InChI=1S/C11H10O/c1-12-11-7-6-9-4-2-3-5-10(9)8-11/h2-8H,1H3

InChI Key

LUZDYPLAQQGJEA-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
Anisole
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB32861)
Cell membrane (HMDB: HMDB32861)

Route of exposure

Enteral

Ingestion (HMDB: HMDB32861)

Source

Exogenous

Exogenous (HMDB: HMDB32861)

Food

Food (HMDB: HMDB32861)

Soy

Soy bean (FooDB: FOOD00085)

Endogenous

Plant

Glycine Max (HMDB: HMDB32861)

Process

Not Available

Role

Biological role

Industrial application

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Immunological adjuvant (HMDB: HMDB32861)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	72 °C	Not Available
Boiling Point	274.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	75.88 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.47	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.065 g/L	ALOGPS
logP	3.37	ALOGPS
logP	2.81	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.97 m³·mol⁻¹	ChemAxon
Polarizability	17.62 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]+	134.852	31661259
DarkChem	[M-H]-	133.631	31661259
DeepCCS	[M+H]+	134.18	30932474
DeepCCS	[M-H]-	130.635	30932474
DeepCCS	[M-2H]-	168.0	30932474
DeepCCS	[M+Na]+	143.539	30932474
AllCCS	[M+H]+	131.7	32859911
AllCCS	[M+H-H2O]+	127.0	32859911
AllCCS	[M+NH4]+	136.1	32859911
AllCCS	[M+Na]+	137.4	32859911
AllCCS	[M-H]-	133.6	32859911
AllCCS	[M+Na-2H]-	134.1	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.	6.74 minutes	32390414
Predicted by Siyang on May 30, 2022	15.8061 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.79 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2053.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	581.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	225.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	360.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	303.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	676.8 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	789.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	129.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1179.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	632.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1568.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	502.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	576.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	460.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	56.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methoxynaphthalene	COC1=CC2=C(C=CC=C2)C=C1	2217.6	Standard polar	33892256
2-Methoxynaphthalene	COC1=CC2=C(C=CC=C2)C=C1	1422.6	Standard non polar	33892256
2-Methoxynaphthalene	COC1=CC2=C(C=CC=C2)C=C1	1456.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Methoxynaphthalene EI-B (Non-derivatized)	splash10-0aor-1900000000-1c20535f4a69bcfc204d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methoxynaphthalene EI-B (Non-derivatized)	splash10-0aor-2900000000-84b3e0628bd2f527ae1b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methoxynaphthalene EI-B (Non-derivatized)	splash10-0aor-1900000000-1c20535f4a69bcfc204d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methoxynaphthalene EI-B (Non-derivatized)	splash10-0aor-2900000000-84b3e0628bd2f527ae1b	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxynaphthalene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0900000000-ccf8c9adde7dafebe859	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methoxynaphthalene 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 - 2-Methoxynaphthalene 10V, Positive-QTOF	splash10-0a4i-0900000000-b1ad72aed00419e872cd	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxynaphthalene 20V, Positive-QTOF	splash10-0a4i-0900000000-6482b5288c37c635e9fa	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxynaphthalene 40V, Positive-QTOF	splash10-0fbc-0900000000-67946d6a51ce2f911531	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxynaphthalene 10V, Negative-QTOF	splash10-0a4i-0900000000-7f5929f25f4a347a587f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxynaphthalene 20V, Negative-QTOF	splash10-0a4i-0900000000-ad2ccbae645853cd88b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxynaphthalene 40V, Negative-QTOF	splash10-0006-0900000000-99f2122554947d468964	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxynaphthalene 10V, Negative-QTOF	splash10-0a4i-0900000000-8c3e029a7181e41a403f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxynaphthalene 20V, Negative-QTOF	splash10-0a4i-0900000000-8c3e029a7181e41a403f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxynaphthalene 40V, Negative-QTOF	splash10-004i-0900000000-6d505baa78133ad36986	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxynaphthalene 10V, Positive-QTOF	splash10-0a4i-0900000000-05067fadfe9b6e821555	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxynaphthalene 20V, Positive-QTOF	splash10-0a4i-0900000000-6a99e14fce415d83a770	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methoxynaphthalene 40V, Positive-QTOF	splash10-004i-3900000000-b02e217f39d8ec711ef4	2021-09-22	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

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

FDB020188

KNApSAcK ID

Not Available

Chemspider ID

6852

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Β-Naphthol methyl ether

METLIN ID

Not Available

PubChem Compound

7119

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1012112

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for 2-Methoxynaphthalene (HMDB0032861)

MOL for HMDB0032861 (2-Methoxynaphthalene)

3D MOL for HMDB0032861 (2-Methoxynaphthalene)

3D SDF for HMDB0032861 (2-Methoxynaphthalene)

3D-SDF for HMDB0032861 (2-Methoxynaphthalene)

PDB for HMDB0032861 (2-Methoxynaphthalene)

3D PDB for HMDB0032861 (2-Methoxynaphthalene)

SMILES for HMDB0032861 (2-Methoxynaphthalene)

INCHI for HMDB0032861 (2-Methoxynaphthalene)

Structure for HMDB0032861 (2-Methoxynaphthalene)

3D Structure for HMDB0032861 (2-Methoxynaphthalene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra