P. aeruginosa Metabolome Database: 3-methyladenine (PAMDB120576)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB120576

Identification

Name:

3-methyladenine

Description:

A methyladenine that is adenine substituted with a methyl group at position N-3.

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

3-methyl-3H-adenine
3-METHYL-3H-PURIN-6-YLAMINE
3-Methyladenine
6-amino-3-methylpurine

Chemical Formula:

C₆H₇N₅

Average Molecular Weight:

149.155

Monoisotopic Molecular Weight:

149.07014

InChI Key:

FSASIHFSFGAIJM-UHFFFAOYSA-N

InChI:

InChI=1S/C6H7N5/c1-11-3-10-5(7)4-6(11)9-2-8-4/h2-3H,7H2,1H3

CAS number:

5142-23-4

IUPAC Name:

3-methyl-3H-purin-6-amine

Traditional IUPAC Name:

3-methyladenine

SMILES:

CN1(C2(=NC=NC(=C(N)N=C1)2))

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of chemical entities known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Organoheterocyclic compounds

Sub Class

Imidazopyrimidines

Direct Parent

6-aminopurines

Alternative Parents

Substituents

6-aminopurine
Aminopyrimidine
Primary aromatic amine
Pyrimidine
Imidolactam
Azole
Imidazole
Heteroaromatic compound
Azacycle
Primary amine
Organonitrogen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyladenine (CHEBI:38635 )
a purine base (3-Methyl-Adenines )

Physical Properties

State:

Solid

Charge:

Melting point:

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
Water Solubility	1.81 mg/mL	ALOGPS
logP	-1.1	ALOGPS
logP	-0.31	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	17.3	ChemAxon
pKa (Strongest Basic)	3.03	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	69.62 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	41.5 m³·mol^-1	ChemAxon
Polarizability	14.48 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:

Not Available

Reactions:

DNA-with-Alkylated-Adenines + Water → DNA-containing-aPurinic-Sites + 3-methyladenine

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-0a4i-4980000000-d3e94e4150e2b870d9b2	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-0a4i-3890000000-235f39119df7c967e9ba	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)	splash10-0a4i-2980000000-251ceed13f156eff1fc4	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS)	splash10-0ab9-9760000000-e3d1a7f774e6bfb718ae	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0udi-0900000000-b32577a48ebafc94ae9a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0udi-1900000000-485f684fffa023d0050e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-0udi-4900000000-6b3b3dd2f2f2d875bf14	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-0a59-9800000000-fe6c9700b9c081b8697a	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0udi-1900000000-b4a28f0f1bd551992615	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive	splash10-0udi-0900000000-8db506e73a05ea922d94	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive	splash10-0udi-0900000000-f67b128eb2b6ac7139b4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-0900000000-53161ff2cee1a6ff34d7	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0udi-0900000000-1ab536fe3bbb9bdfde76	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0giv-9600000000-a22dc2c9e956ce0b2b86	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-31965d8430668c1cef72	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006t-2900000000-1c6ebd899170870682a9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pc0-5900000000-23b69a04a094c620fe7f	View in MoNA
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

Tavazzi B, Lazzarino G, Leone P, Amorini AM, Bellia F, Janson CG, Di Pietro V, Ceccarelli L, Donzelli S, Francis JS, Giardina B (2005)Simultaneous high performance liquid chromatographic separation of purines, pyrimidines, N-acetylated amino acids, and dicarboxylic acids for the chemical diagnosis of inborn errors of metabolism. Clinical biochemistry 38, Pubmed: 16139832
Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Analytical chemistry 84, Pubmed: 22770225
Li M, Yang X, Wang H, Xu E, Xi Z (2014)Inhibition of androgen induces autophagy in benign prostate epithelial cells. International journal of urology : official journal of the Japanese Urological Association 21, Pubmed: 23819759
Huang YT, Cheng CC, Lin TC, Chiu TH, Lai PC (2014)Therapeutic potential of sepantronium bromide YM155 in gemcitabine-resistant human urothelial carcinoma cells. Oncology reports 31, Pubmed: 24297644
Pickard RD, Spencer BH, McFarland AJ, Bernaitis N, Davey AK, Perkins AV, Chess-Williams R, McDermott CM, Forbes A, Christie D, Anoopkumar-Dukie S (2015)Paradoxical effects of the autophagy inhibitor 3-methyladenine on docetaxel-induced toxicity in PC-3 and LNCaP prostate cancer cells. Naunyn-Schmiedeberg's archives of pharmacology 388, Pubmed: 25708950
Tran AT, Ramalinga M, Kedir H, Clarke R, Kumar D (2015)Autophagy inhibitor 3-methyladenine potentiates apoptosis induced by dietary tocotrienols in breast cancer cells. European journal of nutrition 54, Pubmed: 24830781

Synthesis Reference:

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

Links

External Links:

Resource	Link
METABOLIGHTS	MTBLC38635
HMDB	HMDB11600
DRUGBANK	DB04104
CHEBI	38635

3-methyladenine (PAMDB120576)

Structure for 3-methyladenine (PAMDB120576)