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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:32:09 UTC

Update Date

2023-02-21 17:25:48 UTC

HMDB ID

HMDB0037296

Secondary Accession Numbers

HMDB37296

Metabolite Identification

Common Name

3-Acetyl-2,7-naphthyridine

Description

3-Acetyl-2,7-naphthyridine belongs to the class of organic compounds known as naphthyridines. Naphthyridines are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom. 3-Acetyl-2,7-naphthyridine has been detected, but not quantified in, several different foods, such as herbal tea, fats and oils, green tea, teas (Camellia sinensis), and red tea. This could make 3-acetyl-2,7-naphthyridine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Acetyl-2,7-naphthyridine.

Structure

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

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   12  N   UNK     0       6.668  -2.310   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    8                                                       
CONECT    3    2   11                                                       
CONECT    4    8   10                                                       
CONECT    5    9   11                                                       
CONECT    6    9   12                                                       
CONECT    7    1   10   13                                                  
CONECT    8    2    4    9                                                  
CONECT    9    5    6    8                                                  
CONECT   10    4    7   12                                                  
CONECT   11    3    5                                                       
CONECT   12    6   10                                                       
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,7-Naphthyridine-3-methylketone	MeSH
1-(2,7-Naphthyridin-3-yl)-ethanone	HMDB
1-(2,7-Naphthyridin-3-yl)ethanone, 9ci	HMDB
Naphthyridylmethylketone	HMDB
3-Acetyl-2,7-naphthyridine	MeSH

Chemical Formula

C₁₀H₈N₂O

Average Molecular Weight

172.1833

Monoisotopic Molecular Weight

172.063662888

IUPAC Name

1-(2,7-naphthyridin-3-yl)ethan-1-one

Traditional Name

1-(2,7-naphthyridin-3-yl)ethanone

CAS Registry Number

73607-00-8

SMILES

CC(=O)C1=CC2=CC=NC=C2C=N1

InChI Identifier

InChI=1S/C10H8N2O/c1-7(13)10-4-8-2-3-11-5-9(8)6-12-10/h2-6H,1H3

InChI Key

VBBXXOOMKKQNNS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthyridines. Naphthyridines are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazanaphthalenes

Sub Class

Naphthyridines

Direct Parent

Naphthyridines

Alternative Parents

Substituents

Naphthyridine
Aryl alkyl ketone
Aryl ketone
Pyridine
Heteroaromatic compound
Ketone
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037296)
Cytoplasm (HMDB: HMDB0037296)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037296)

Source

Exogenous

Exogenous (HMDB: HMDB0037296)

Food

Food (HMDB: HMDB0037296)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Endogenous

Plant

Plant (HMDB: HMDB0037296)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037296)

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	12530 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.64 g/L	ALOGPS
logP	0.98	ALOGPS
logP	0.47	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	14.91	ChemAxon
pKa (Strongest Basic)	4.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	42.85 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	48.23 m³·mol⁻¹	ChemAxon
Polarizability	17.61 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]+	139.009	31661259
DarkChem	[M-H]-	137.037	31661259
DeepCCS	[M+H]+	134.08	30932474
DeepCCS	[M-H]-	131.359	30932474
DeepCCS	[M-2H]-	167.602	30932474
DeepCCS	[M+Na]+	143.141	30932474
AllCCS	[M+H]+	135.8	32859911
AllCCS	[M+H-H2O]+	131.3	32859911
AllCCS	[M+NH4]+	140.1	32859911
AllCCS	[M+Na]+	141.3	32859911
AllCCS	[M-H]-	137.8	32859911
AllCCS	[M+Na-2H]-	138.3	32859911
AllCCS	[M+HCOO]-	138.8	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 × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	3.22 minutes	32390414
Predicted by Siyang on May 30, 2022	10.5997 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.18 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1124.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	385.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	34.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	231.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	97.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	318.9 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	242.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	341.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	658.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	40.2 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	841.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	235.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	354.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	707.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	524.9 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	229.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Acetyl-2,7-naphthyridine	CC(=O)C1=CC2=CC=NC=C2C=N1	2166.1	Standard polar	33892256
3-Acetyl-2,7-naphthyridine	CC(=O)C1=CC2=CC=NC=C2C=N1	1588.7	Standard non polar	33892256
3-Acetyl-2,7-naphthyridine	CC(=O)C1=CC2=CC=NC=C2C=N1	1612.4	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 - 3-Acetyl-2,7-naphthyridine GC-MS (Non-derivatized) - 70eV, Positive	splash10-059x-3900000000-a5c243d3eb72418f8520	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Acetyl-2,7-naphthyridine 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 - 3-Acetyl-2,7-naphthyridine 10V, Positive-QTOF	splash10-00di-0900000000-41cedb7d00e7b7eac843	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,7-naphthyridine 20V, Positive-QTOF	splash10-05fr-0900000000-0ac3e990c7c5e207d6d0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,7-naphthyridine 40V, Positive-QTOF	splash10-0a4i-0900000000-45039c2c9af2fac467aa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,7-naphthyridine 10V, Negative-QTOF	splash10-00di-0900000000-d8c9c01ec14da1e39852	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,7-naphthyridine 20V, Negative-QTOF	splash10-00di-0900000000-114ec2b9ccf8dde40d39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,7-naphthyridine 40V, Negative-QTOF	splash10-004i-0900000000-289b6c39e18fe799583e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,7-naphthyridine 10V, Negative-QTOF	splash10-00fr-0900000000-9336d9e8875928740d21	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,7-naphthyridine 20V, Negative-QTOF	splash10-004i-0900000000-4d63a8d640822047a23f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,7-naphthyridine 40V, Negative-QTOF	splash10-0fb9-1900000000-99f2d8e812f3055a04fc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,7-naphthyridine 10V, Positive-QTOF	splash10-00di-0900000000-95370f49b668a829b381	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,7-naphthyridine 20V, Positive-QTOF	splash10-00di-0900000000-f7eea75e709aa772f169	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Acetyl-2,7-naphthyridine 40V, Positive-QTOF	splash10-0ufr-1900000000-89d3977a916ba0276111	2021-09-24	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

Cytoplasm
Extracellular

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

FDB016315

KNApSAcK ID

C00054660

Chemspider ID

137230

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155795

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1859721

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 3-Acetyl-2,7-naphthyridine (HMDB0037296)

MOL for HMDB0037296 (3-Acetyl-2,7-naphthyridine)

3D MOL for HMDB0037296 (3-Acetyl-2,7-naphthyridine)

3D SDF for HMDB0037296 (3-Acetyl-2,7-naphthyridine)

3D-SDF for HMDB0037296 (3-Acetyl-2,7-naphthyridine)

PDB for HMDB0037296 (3-Acetyl-2,7-naphthyridine)

3D PDB for HMDB0037296 (3-Acetyl-2,7-naphthyridine)

SMILES for HMDB0037296 (3-Acetyl-2,7-naphthyridine)

INCHI for HMDB0037296 (3-Acetyl-2,7-naphthyridine)

Structure for HMDB0037296 (3-Acetyl-2,7-naphthyridine)

3D Structure for HMDB0037296 (3-Acetyl-2,7-naphthyridine)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra