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이노신

Inosine

HCID 135398641
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인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
58-63-9
표준 SMILES
O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
InChIKey
UGQMRVRMYYASKQ-KQYNXXCUSA-N
분자식
C10H12N4O5
평균 분자량
268.23 g/mol
단동위원소 질량
268.0807695

개요

Inosine is a purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N9-glycosidic bond. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a human metabolite. It is a purines D-ribonucleoside and a member of inosines. It is functionally related to a hypoxanthine and a ribofuranose.

이름 및 식별자

우선 이름
Inosine
IUPAC
9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-purin-6-one
현지명
이노신
영어명
Inosine
분자식
C10H12N4O5
분자량
268.23

이름 및 동의어

inosine58-63-9HypoxanthosineRibonosineOxiaminAtorelHypoxanthine ribosideTrophicardylSelferHypoxanthine D-riboside9-beta-D-RibofuranosylhypoxanthineHypoxanthine ribonucleoside
이름 더 보기
이노신HXRRIBOXINEnosinelnosine(-)-Inosinebeta-InosineInosine-13C3(2R,3R,4S,5R)-2-(6-hydroxy-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diolIno
Hypoxanthine nucleosideInosinaInosinumInotinINO 495DTXSID20459935A614L51CTNSC-20262

데이터베이스 식별자

CAS
58-63-9
PubChem CID
135398641
DTXSID
DTXSID2045993
ChEMBL
CHEMBL1556
ChEBI
CHEBI:17596
UNII

물성

구조 계산 물성

XLogP
-1.3
극성 표면적
129 Ų
수소 결합 공여자 수
4
수소 결합 수용자 수
7
회전 가능 결합 수
2
무거운 원자 수
19
형식 전하
0
복잡도
405

실험 및 물리화학적 성질

Chemical ClassesBiological Agents -> Nucleic Acids and Derivatives
DrugsPharmaceuticals -> Listed in ZINC15
SpringerMaterials PropertiesCrystal structure
LogP · 2건

-2.10

-1.81

Solubility · 2건

15.8 mg/mL

>40.2 [ug/mL] (The mean of the results at pH 7.4)

Melting Point218 °C
Physical Description · 2건

White crystalline solid; [Sigma-Aldrich MSDS]

Solid

Collision Cross Section · 5건

161.7 Ų [M-H]- [CCS Type: DT; Method: stepped-field]

170.8 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

153 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine]

170.7 Ų [M+Na]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

172.1 Ų [M+Na]+

물리화학적 성질

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 3건

This chemical does not meet GHS hazard criteria for 91.3% (21 of 23) of all reports.

Not Classified

Aggregated GHS information provided per 23 reports by companies from 3 notifications to the ECHA C&L Inventory.

유해성 정보

Regulatory Information · 3건

Chemical: Inosine

REACH registered substance: Inosine (EC: 200-390-4)

Inosine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Inosine: Environment tier I assessment
Hazards SummaryCauses changes in thymus weight, normocytic anemia, and changes in blood serum composition in 93-day oral studies of rats; [RTECS] May cause irritation; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesNot Classified

안전 데이터

wgk
2
tsca
TSCA listed
rtecs
NM7460000
독성
LD50 oral in rat: > 10gm/kg
HS 번호
29389090
risk_code
36/37/38
hazard_code
Xi
safety_code
24/25-36-26
기존화학 물질
KE-30339
F 고인화성물질
10
스토리지 클래스
11 - Combustible Solids

화학 및 산업

약리 정보

ATC Code · 6건

S - Sensory organs

D - Dermatologicals

G - Genito urinary system and sex hormones

QG - Genito urinary system and sex hormones

QD - Dermatologicals

QS - Sensory organs

PharmacodynamicsInosine may have neuroprotective, cardioprotective, anti-inflammatory and immunomodulatory activities.
Mechanism of Action · 1건

Inosine has been found to have potent axon-promoting effects in vivo following unilateral transection of the corticospinal tract of rats. The mechanism of this action is unclear. Possibilities include serving as an agonist of a nerve growth factor-activated protein kinase (N-Kinase), conversion to cyclic nucleotides that enable advancing nerve endings to overcome the inhibitory effects of myelin, stimulation of differentiation in rat sympathetic neurons, augmentation of nerve growth factor-induced neuritogenesis and promotion of the survival of astrocytes, among others. The mechanism of inosine's possible cardioprotective effect is similarly unclear. Inosine has been reported to have a positive inotropic effect and also to have mild coronary vasodilation activity. Exogenous inosine may contribute to the high-energy phosphate pool of cardiac muscle cells and favorably affect bioenergetics generally. Inosine has also been reported to enhance the myocardial uptake of carbohydrates relative to free fatty acids as well as glycolysis. In cell culture studies, inosine has been found to inhibit the production, in immunostimulated macrophages and spleen cells, of the proinflammatory cytokines, tumor necrosis factor (TNF)-alpha, interleukin (IL)-1, interleukin (IL)-12, macrophage-inflammatory protein-1 alpha and interferon (IFN)-gamma. It also suppressed proinflammatory cytokine production and mortality in a mouse endotoxemic model. These actions might account for the possible immunomodulatory, anti-inflammatory and anti-ischemic actions of inosine.

Metabolism/Metabolites · 1건

In the liver, inosine may be catabolized by a series of reactions culminating in the production of uric acid and also may be metabolized to adenine- and guanine-containing nucleotides. Inosine not metabolized in the liver is transported via the systemic circulation and distributed to various tissues of the body, where it is metabolized in similar fashion as in the liver. Uric acid, the purine end-product of inosine catabolism, is excreted in the urine.

관련 반응

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화합물 노트

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이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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5A614L51CT
EC Number
163-621-7、200-390-4
Nikkaji
J1.388I
녹는점
222 · 222-226 °C (dec.) (lit.)
끓는 점
226 C · 226 C (dec.)
밀도
1.3846 · 1.3846 (rough estimate)
굴절률
-52 ° · -52 ° (C=1, H2O)
저장 조건
Keep in dark place,Sealed in dry,Room Temperature
용해도
2 O: · H2O: 0.5 M, 투명, 무색
산도 계수 (pKa)
13.24 · 13.24±0.70(Predicted)
물리적 상태
결정성 분말
색상
하얀색
수소이온지수(pH)
1.2 · 1.2;8.8
냄새
냄새 없는
수용성
2.1 g/100mL · 2.1g/100mL(20℃)
Merck
14 · 14,4975
BRN
624889 · 624889
안정성
흡습성
화장품 원료 기능
피부 보호피부 컨디셔닝
InChI
1S/C10H12N4O5/c15-1-4-6(16)7(17)10(19-4)14-3-13-5-8(14)11-2-12-9(5)18/h2-4,6-7,10,15-17H,1H2,(H,11,12,18)/t4-,6-,7-,10-/m1/s1
InChIKey
UGQMRVRMYYASKQ-PKJMTWSGSA-N
SMILES
OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3C(=O)NC=Nc23
LogP
-1.97 · -1.970 (est)
NIST
Inosine(58-63-9)
EPA
Inosine (58-63-9)

화학적 성질

White crystalline powder

Absorption, Distribution and ExcretionIngested inosine is absorbed from the small intestine.
Tissue LocationsBrain
Cellular LocationsCytoplasm
Metabolite PathwaysAdenine phosphoribosyltransferase deficiency (APRT)

용도 및 제조

Uses · 2건

A cellular activator found in meat, meat extracts, and sugar beets; [Merck Index] A purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules. (Dorland, 28th ed) [ChemIDplus]

Use (kg; approx.) in Germany (2009): >10

General Manufacturing InformationInosine: ACTIVE
응용 분야 · 3건

출처Inosine is a synthetic

용도Inosine has been used:as a medium supplement in nucleotide rescue experiments in pancreatic cancer cell lines.as a component in holidic (synthetic) medium and in larval two-choice preference assay.as a reference standard in mass spectroscopy.

일반 설명Inosine is a non-canonical nucleotide majorly present as monophosphate. It has ability to base pair with deoxythymidine, deoxyadenosine and deoxyguanosine. Incorporation of inosine in place of guanine modulates translational events. Inosine has antioxidant, anti-inflammatory and neuroprotective functionality. Inosine is prescribed as a therapeutic supplement for nerve injury, inflammation and oxidative stress. It modulates biological processes through adenosine receptors. Its enhances neurite outgrowth in depressive disorders via adenosine receptors. Inosine is also used for treating sepsis in infections.

상·하류 제품 정보

상류 원료

Acid off백금분5′-이노신산이나트륨염화나트륨5′-구아닐산이나트륨한천트리스붕산염EDTA완충액,10X,DNASE,RNASE및프로테아제없음,PH8.3,분자생물학용BEEF EXTRACTInosinic AcidYeast extractcorn syrup황산아데노신아질산바륨일수화물

하류 제품

디디아이리바비린beta-D-Ribofuranose 1,2,3,5-tetraacetateDL-트립토판Calcium 5'-ribonucleotide2-(6-ethylaminopurin-9-yl)-5-(hydroxymethyl)oxol5"-O-(4,4"-디메톡시트리틸)-이노신6-Chloropurine ribonucleosideN6-사이클로헥실라데노신

추가 설명

정의ChEBI: A purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N9-glycosidic bond.