ECMDB: 2-Naphthaldehyde (ECMDB20047) (M2MDB000896)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (4)XML

Proteins (755)

Record Information

Version

2.0

Creation Date

2012-05-31 14:24:40 -0600

Update Date

2015-06-03 17:19:12 -0600

Secondary Accession Numbers

ECMDB20047

Identification

Name:

2-Naphthaldehyde

Description

2-naphthaldehyde is a member of the chemical class known as Naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Formylnaphthalene
2-Naphthalenecarboxaldehyde
2-Naphthalenecarboxaldehyde (9CI)
b-Formylnaphthalene
b-Naphthaldehyde
b-Naphthylaldehyde
b-Naphthylcarboxaldehyde
Beta-Formylnaphthalene
Beta-Naphthaldehyde
Beta-Naphthylaldehyde
Beta-Naphthylcarboxaldehyde
N206_ALDRICH
NAPHTHALENE-2-CARBONITRILE
β-Formylnaphthalene
β-Naphthaldehyde
β-Naphthylaldehyde
β-Naphthylcarboxaldehyde

Chemical Formula:

C₁₁H₈O

Weight:

Average: 156.1806
Monoisotopic: 156.057514878

InChI Key:

PJKVFARRVXDXAD-UHFFFAOYSA-N

InChI:

InChI=1S/C11H8O/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-8H

CAS number:

66-99-9

IUPAC Name:

naphthalene-2-carbaldehyde

Traditional IUPAC Name:

2-naphthaldehyde

SMILES:

O=CC1=CC2=CC=CC=C2C=C1

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
Aryl-aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aldehyde
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

naphthaldehyde (CHEBI:52368 )

Physical Properties

State:

Solid

Charge:

Melting point:

62 °C

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.079 g/L	ALOGPS
logP	3	ALOGPS
logP	2.68	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	49.09 m³·mol⁻¹	ChemAxon
Polarizability	16.83 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Cytoplasm

Reactions:

(2-Naphthyl)methanol + NAD <> 2-Naphthaldehyde + NADH + Hydrogen ion
(2-Naphthyl)methanol + NAD > 2-Naphthaldehyde + Hydrogen ion + NADH

SMPDB Pathways:

Collection of Reactions without pathways

PW001891

KEGG Pathways:

Microbial metabolism in diverse environments ec01120
Naphthalene degradation ec00626

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-0900000000-06c638e5fed22972adaa	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-d4001d81b371dc587846	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-0900000000-10d1a64a1302bb784dd5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-066r-3900000000-f68aa9c96fdd352b0e6e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-e4c4ff203b034768d30d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-e4c4ff203b034768d30d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-0900000000-c40c461869cd95a91ad3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-4c681a926812e6a7acca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-0900000000-fec0205cf2a86e12856a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-0900000000-cedd03a28deddaec9c31	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-056r-0900000000-7b7e888c814ee9f36646	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-ec6816397577a7beb93f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-0900000000-2abb25dc3c5134b0434e	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	52368
HMDB ID	HMDB0060349
Pubchem Compound ID	6201
Kegg ID	C14099
ChemSpider ID	5966
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Aldehyde-alcohol dehydrogenase

General function:: Involved in oxidoreductase activity
Specific function:: This enzyme has three activities:ADH, ACDH, and PFL- deactivase. In aerobic conditions it acts as a hydrogen peroxide scavenger. The PFL deactivase activity catalyzes the quenching of the pyruvate-formate-lyase catalyst in an iron, NAD, and CoA dependent reaction
Gene Name:: adhE
Uniprot ID:: P0A9Q7
Molecular weight:: 96126

Reactions

An alcohol + NAD(+) = an aldehyde or ketone + NADH.
Acetaldehyde + CoA + NAD(+) = acetyl-CoA + NADH.

Protein Details

2. S-(hydroxymethyl)glutathione dehydrogenase

General function:: Involved in zinc ion binding
Specific function:: Has high formaldehyde dehydrogenase activity in the presence of glutathione and catalyzes the oxidation of normal alcohols in a reaction that is not GSH-dependent. In addition, hemithiolacetals other than those formed from GSH, including omega-thiol fatty acids, also are substrates
Gene Name:: frmA
Uniprot ID:: P25437
Molecular weight:: 39359

Reactions

S-(hydroxymethyl)glutathione + NAD(P)(+) = S-formylglutathione + NAD(P)H.
An alcohol + NAD(+) = an aldehyde or ketone + NADH.

Protein Details

3. Alcohol dehydrogenase, propanol-preferring

General function:: Involved in zinc ion binding
Specific function:: Preferred specificity is towards 1-propanol
Gene Name:: adhP
Uniprot ID:: P39451
Molecular weight:: 35379

Reactions

An alcohol + NAD(+) = an aldehyde or ketone + NADH.

Protein Details

4. predicted Fe-containing alcohol dehydrogenase, Pfam00465 family

General function:: Not Available
Specific function:: Not Available
Gene Name:: yiaY
Uniprot ID:: P37686
Molecular weight:: Not Available

2-Naphthaldehyde (ECMDB20047) (M2MDB000896)

Structure for #<Compound:0xb0c07690>

Enzymes

Reactions

Reactions

Reactions