5-Isopentyl-6-methyl-2-
(methylsulfanyl)-4-pyrimidinol
PubChem CID: 135488643
Structure:
Find Similar Structures
Molecular Formula: C11H18N2OS
AC1LCBJA
5-Isopentyl-6-methyl-2-(methylsulfanyl)-4-pyrimidinol
CTK7B5232
Chemical Names:
5-isopentyl-6-methyl-2-methylsulfanyl-3H-pyrimidin-4-one
BLSHRKCRICUPQW-UHFFFAOYSA-N
More...
Molecular Weight: 226.338 g/mol
Modify:
2019-06-08
Dates:
Create:
2019-01-15
1Structures
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1.12D Structure
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Chemical Structure Depiction
1.23D Conformer
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Interactive Chemical Structure Model
2Names and Identifiers
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2.1Computed Descriptors
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2.1.1IUPAC Name
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4-methyl-5-(3-methylbutyl)-2-methylsulfanyl-1H-pyrimidin-6-one
2.1.2InChI
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InChI=1S/C11H18N2OS/c1-7(2)5-6-9-8(3)12-11(15-4)13-10(9)14/h7H,5-6H2,1-
4H3,(H,12,13,14)
2.1.3InChI Key
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BLSHRKCRICUPQW-UHFFFAOYSA-N
2.1.4Canonical SMILES
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CC1=C(C(=O)NC(=N1)SC)CCC(C)C
2.2Molecular Formula
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C11H18N2OS
2.3Synonyms
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2.3.1Depositor-Supplied Synonyms
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AC1LCBJA
5-Isopentyl-6-methyl-2-(methylsulfanyl)-4-pyrimidinol
CTK7B5232
5-isopentyl-6-methyl-2-methylsulfanyl-3H-pyrimidin-4-one
BLSHRKCRICUPQW-UHFFFAOYSA-N
SBB096994
100051-32-9
6-methyl-5-(3-methylbutyl)-2-methylthiopyrimidin-4-ol
4-HYDROXY-6-METHYL-5-(3-METHYLBUTYL)-2-METHYLTHIOPYRIMIDINE
6-methyl-5-(3-methylbutyl)-2-methylsulfanyl-1H-pyrimidin-4-one
3Chemical and Physical Properties
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3.1Computed Properties
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Property Name Property Value
Molecular Weight 226.338 g/mol
XLogP3-AA 2.7
Hydrogen Bond Donor Count 1
Property Name Property Value
Hydrogen Bond Acceptor Count 3
Rotatable Bond Count 4
Exact Mass 226.114 g/mol
Monoisotopic Mass 226.114 g/mol
Topological Polar Surface Area 66.8 A^2
Heavy Atom Count 15
Formal Charge 0
Complexity 319
Isotope Atom Count 0
Defined Atom Stereocenter Count 0
Undefined Atom Stereocenter Count 0
Defined Bond Stereocenter Count 0
Undefined Bond Stereocenter Count 0
Covalently-Bonded Unit Count 1
Compound Is Canonicalized Yes
4Spectral Information
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4.1Mass Spectrometry
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4.1.1GC-MS
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NIST
297962
Number
Library Main library
Total Peaks 117
m/z Top
170
Peak
m/z 2nd
169
Highest
m/z 3rd
96
Highest
Thumbnail
5Related Records
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5.1Substances
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5.1.1Related Substances
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Same 9 Records
5.1.2Substances by Category
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5 CategoriesExpanded View
6Chemical Vendors
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Showing 1 Substance per VendorView All
View in Entrez
TimTec
PubChem SID: 143465840
Purchasable Chemical: SBB096994 (URL not provided...)
Chemhere
PubChem SID: 315426356
Purchasable Chemical: Achem476645 (URL not provided...)
ChemTik
PubChem SID: 162990146
Purchasable Chemical: CTK7B5232
7Information Sources
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Filter by Source
1. NIST
5-Isopentyl-6-methyl-2-(methylsulfanyl)-4-pyrimidinol
[Link]
2. PubChem
[Link]
1-Aminocyclopentanecarboxylic acid
Name 1-aminocyclopentanecarboxylic acid
A non-proteinogenic α-amino acid that is cyclopentane
substituted at position 1 by amino and carboxy groups. (Asam
Definition α-amino non-proteinogenik yang digantikan oleh
siklopentana pada posisi 1 oleh gugus amino dan
karboksi.)
Cycloleucine is a non-proteinogenic amino acid. It could be classified as a cyclic derivate of norleucine,
having two hydrogen atoms less. Leading structure is a cyclopentane-ring. The α-carbon atom is not a
stereocenter. Cycloleucine is a non-metabolisable amino acid and is a specific and reversible inhibitor of
nucleic acid methylation, and as such is widely used in biochemical [Link] 2007, a research study
performed on primary rat hepatocytes had shown that cycloleucine can lower S-Adenosyl_methionine
(SAM) levels in control hepatocytes by inhibiting the conversion of 5'-methylthioadenosine to SAM
through the methionine salvage pathway. Cycloleucine treatment in conjunction with higher levels of
cytochrome P450 2E1 (CYP2E1) and lower SAM levels in pyrazole hepatocytes had shown an increased
amount of cell apoptosis when compared to control hepatocytes.
(Sikoleusin adalah asam amino non-proteinogenik. Ini dapat diklasifikasikan
sebagai turunan siklik dari norleusin, memiliki dua atom hidrogen lebih sedikit.
Struktur utama adalah cincin-siklopentana. Atom α-karbon bukanlah stereocenter.
Cycloleucine adalah asam amino non-metabolisable dan merupakan inhibitor
spesifik dan reversibel dari metilasi asam nukleat, dan dengan demikian banyak
digunakan dalam percobaan biokimia. Pada tahun 2007, sebuah penelitian yang
dilakukan pada hepatosit tikus primer telah menunjukkan bahwa cycloleucine dapat
menurunkan S-Adenosyl_methionine (SAM) tingkat dalam hepatosit kontrol dengan
menghambat konversi 5'-methylthioadenosine menjadi SAM melalui jalur
penyelamatan metionin. Pengobatan sikoleusin bersama dengan tingkat sitokrom
P450 2E1 (CYP2E1) yang lebih tinggi dan kadar SAM yang lebih rendah dalam
hepatosit pirazol telah menunjukkan peningkatan jumlah apoptosis sel bila
dibandingkan dengan kontrol hepatosit.)
Formula C6H11NO2
Net Charge 0
Average Mass 129.15700
Monoisotopic Mass 129.07898
InChI InChI=1S/C6H11NO2/c7-6(5(8)9)3-1-2-4-6/h1-4,7H2,(H,8,9)
InChIKey NILQLFBWTXNUOE-UHFFFAOYSA-N
SMILES NC1(CCCC1)C(O)=O
Carroll N, Hughes L, McEntee G, Parle-McDermott A (2012)
Investigation of the molecular response to folate metabolism inhibition.
The Journal of nutritional biochemistry 23, 1531-1536 [PubMed:22402366]
[show Abstract]
Kowalczyk W, Prahl A, Dawidowska O, Derdowska I, Sobolewski D, Hartrodt B, Neubert K, Slaninová J,
Lammek B (2005)
The influence of 1-aminocyclopentane-1-carboxylic acid at position 2 or 3 of AVP and its analogues on their
pharmacological properties.
Journal of peptide science : an official publication of the European Peptide Society 11, 584-588
[PubMed:15747318]
[show Abstract]
Ramsey RB, Fischer VW (1978)
Effect of 1-aminocyclopentane-1-carboxylic acid (cycloleucine) on developing rat central nervous system
phospholipids.
Journal of neurochemistry 30, 447-457 [PubMed:624950]
Manz HJ, Robertson DM, Haas RA, Meyers N (1976)
Cycloleucine uptake in the brainstem of thiamine-deficient rats.
Acta neuropathologica 36, 47-56 [PubMed:970113]
[show Abstract]
Nixon RA, Suva M, Wolf MK (1976)
Neurotoxicity of a non-metabolizable amino acid, 1-aminocyclopentane-1-carboxylic acid: antagonism by amino
acids in cultures of cerebellum.
Journal of neurochemistry 27, 245-251 [PubMed:956827]
Rosenthale ME, Gluckman MI (1968)
Immunopharmacologic activity of 1-aminocyclopentane-1-carboxylic acid.
Experientia 24, 1229-1230 [PubMed:5703023]
Cutler RW, Lorenzo AV (1968)
Transport of 1-aminocyclopentanecarboxylic acid from feline cerebrospinal fluid.
Science (New York, N.Y.) 161, 1363-1364 [PubMed:5673450]
[show Abstract]
Brown RR (1967)
Aminoaciduria resulting from cycloleucine administration in man.
Science (New York, N.Y.) 157, 432-434 [PubMed:6028026]
[show Abstract]
STERLING WR, HENDERSON JF (1963)
Studies of the mechanism of action 1-aminocyclopentane-1-carboxylic acid.
Biochemical pharmacology 12, 303-316 [PubMed:13983935]
STERLING WR, HENDERSON JF, MANDEL HG, SMITH PK (1962)
The metabolism of 1-aminocyclopentane-1-carboxylic acid in normal and neoplastic tissues.
Biochemical pharmacology 11, 135-145 [PubMed:13916973]
CONNORS TA, ELSON LA, HADDOW A, ROSS WC (1960)
The pharmacology and tumour growth inhibitory activity of 1-aminocyclopentane-1-carboxylic acid and related
compounds.
Biochemical pharmacology 5, 108-129 [PubMed:13880910]