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D-Arginine

HCID 71070
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
157-06-2
Standard SMILES
NC(N)=NCCC[C@@H](N)C(=O)O
InChIKey
ODKSFYDXXFIFQN-SCSAIBSYSA-N
Molecular formula
C6H14N4O2
Average molar mass
174.2 g/mol
Monoisotopic mass
174.1116757

Overview

D-arginine is a D-alpha-amino acid that is the D-isomer of arginine. It has a role as an EC 4.1.1.19 (arginine decarboxylase) inhibitor and a mouse metabolite. It is a D-alpha-amino acid and an arginine. It is a conjugate base of a D-argininium(1+). It is a conjugate acid of a D-argininate. It is an enantiomer of a L-arginine.

Names & identifiers

Preferred name
D-Arginine
IUPAC
(2R)-2-amino-5-(diaminomethylideneamino)pentanoic acid
English name
D(-)-Arginine
Molecular formula
C6H14N4O2
Molecular weight
174.2

Names & synonyms

D-Arginine157-06-2D-Arginin(R)-2-amino-5-guanidinopentanoic acidArginine, d-D-2-Amino-5-guanidinovaleric acid(2R)-2-amino-5-carbamimidamidopentanoic acid(-)-D-Arginine hydrateEINECS 205-866-5(2R)-2-amino-5-(diaminomethylideneamino)pentanoic acid(2R)-2-amino-5-guanidinopentanoic acidR54Z304Z7C
Show more names
D-ARGH-D-ARG-OHD-Arg-OHD-(-)-ARGININEH-D-ArginineR-(-)-ARGININED-Arginine,98%
(2R)-2-amino-5-[(diaminomethylidene)amino]pentanoic acidCHEBI:15816DTXSID40883354(2R)-2-amino-5-(carbamimidamido)pentanoic acid(2R)-2-amino-5-((diaminomethylidene)amino)pentanoic acidRefChem:582678DTXCID601022891InChI=1/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m1/s

Database identifiers

CAS
157-06-2
PubChem CID
71070
DTXSID

Properties

Computed structural properties

XLogP
-4.2
Topological polar surface area
128 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
4
Rotatable bonds
5
Heavy atoms
12
Formal charge
0
Complexity
176

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift
Physical DescriptionSolid

Physicochemical properties

Melting point
226 °C · 226 °C (dec.) (lit.)
alpha
-28.5 · -28.5 º (c=8, 6 N HCl)
Boiling point
305.18 °C · 305.18°C (rough estimate)
Density
1.2297 · 1.2297 (rough estimate)
refractive index
-23 ° · -23 ° (C=8, 6mol/L HCl)
storage temp.
Keep in dark place,Inert atmosphere,Room temperature
solubility
Aqueous Acid (Slightly), Water (Slightly)
form
Solid
pka
2.49 · 2.49±0.24(Predicted)
color
White to Off-White
Water Solubility
SOLUBLE

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 82.6% (38 of 46) of all reports.

Warning

H319 (17.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 46 reports by companies from 4 notifications to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesEye Irrit. 2A (17.4%)

Safety data

F
9
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
CF1934220
hs_code
29252000
risk_code
36-36/37/38-20/21/22
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi,Xn
safety_code
26-36
hazard_class
IRRITANT
Storage Class
11 - Combustible Solids
Hazard statements
H319
Precautionary statements
P264-P280i-P337+P313-P305+P351+P338

Chemistry & industry

Pharmacology

Tissue LocationsEpidermis
Cellular LocationsPeroxisome
Metabolite PathwaysD-Arginine and D-Ornithine Metabolism

Uses & manufacturing

General Manufacturing InformationD-Arginine: ACTIVE
Applications · 3 items

DescriptionD-arginine is the D-form of arginine, which is a kind of amino acids. It can be reacted with hydrogen peroxide for non-enzymatic synthesis of nitric oxide. It has certain pharmacological activities. For example, its derivative, 1-deamino-8-D-arginine vasopressin is useful for the management of haemophilia and von Willebrand’s disease. It also has the potential to inhibit the proliferation of certain cancer cells. In biological research, D-arginine is frequently used in the studies of L-arginine/nitric oxide pathway as an inactive form of L-arginine.

UsesArginine is an essential amino acid found in food and plant sources, and many biological systems. D-Arginine is extensively used in studies on L-arginine/nitric oxide pathway as an inactive form of L-arginine, even in man. D-Arginine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). D-Arginine can be found in human epidermis and platelet tissues. Within the cell, D-arginine is primarily located in the peroxisome. D-Arginine specifically can inhibit arginine decarboxylase enzymes and also functions as a metabolite.

Uses1-Deamino-8-D-arginine vasopressin makes a new pharmacological approach to the management of haemophilia and von Willebrand's disease. A novel nonenzymatic pathway for the generation of nitric oxide is by the reaction of hydrogen peroxide and d- or l-arginine.

Upstream & downstream products

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
DTXSID40883354
ChEMBL
CHEMBL212301
ChEBI
CHEBI:15816
UNII
R54Z304Z7C
EC Number
205-866-5
Nikkaji
J9.186C
Specific Heat Capacity
1.33 J/ · Cp(crystal): 1.33 J/(g·K), at 25℃
Sensitive
Air Sensitive
BRN
1725412 · 1725412
Major Application
peptide synthesis
InChI
1S/C6H14N4O2/c7-4(5(11)12)2-1-3-10-6(8)9/h4H,1-3,7H2,(H,11,12)(H4,8,9,10)/t4-/m1/s1
InChIKey
ODKSFYDXXFIFQN-SCSAIBSYSA-N
SMILES
N[C@H](CCCNC(N)=N)C(O)=O
LogP
-0.999 · -0.999 (est)
CAS DataBase Reference
157 · 157-06-2(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
54 Z304Z7C · R54Z304Z7C
EPA Substance Registry System
D-Arginine (157-06-2)
UNSPSC Code
12352209 · 12352209
NACRES
32 · NA.32
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
319 · H319
Precautionary statements
264 · P264-P280i-P337+P313-P305+P351+P338
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi,Xn
Risk Statements
36 · 36-36/37/38-20/21/22
Safety Statements
26 · 26-36
WGK Germany
3 · 3
RTECS
1934220 · CF1934220
F
9 · 9
TSCA
TSCA listed
HazardClass
IRRITANT
HS Code
29252000 · 29252000
Storage Class
11 · 11 - Combustible Solids

Upstream raw materials

O-methylisoureaD-Ornithine monohydrochloride

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
杭州倍生元生物科技有限公司15068777134 15068777134 · [email protected]
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
韶远科技(上海)有限公司4000665055 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]
Syntechem Co.,Ltd[email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
武汉易泰科技有限公司上海分公司18930552037 · [email protected]
宁波亿诺化学品有限公司86-574-27787657 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
阿法埃莎(中国)化学有限公司400-6106006 · [email protected]
安耐吉化学&3A(安徽泽升科技股份有限公司)400-0056266 · [email protected]
新乡市翌诚生物科技有限公司0373-5799336 18237327559 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海柯维化学技术有限公司021-64609169 18901607656 · [email protected]
南京欣丰康生物科技有限公司025-84683399 13952017251 · [email protected]
上海星酶生物科技有限公司18112588827 · [email protected]
上海景颜化工科技有限公司13817811078 · [email protected]
嘉兴市艾森化工有限公司0573-85285100 18627885956 · [email protected]
Pure Chemistry Scientific Inc.001-857-928-2050 or 1-888-588-9418 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
张家港市思普生化有限公司512-0512-58992291,58992287 18606280718 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
孝感深远化工有限公司15527621225; 15527621225 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
大赛璐药物手性技术(上海)有限公司021-50460086-9 15921403865 · [email protected]
南京红杉生物科技有限公司158-05183379 15805183379 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
天津希恩思生化科技有限公司400 638 7771 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
百盛HK进出口有限公司+86-18068513926
河南多贝化工有限公司0370-2785118 17550508557 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
江苏艾康生物医药研发有限公司025-66113011 13913916777 · [email protected]
TCI AMERICA800-4238616 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
TCI Europe320-37350700 · [email protected]
上海贤鼎生物科技有限公司4009209199 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
越林试剂021-62960152 · [email protected]
泰州天鸿生化科技有限公司0523-86132544 15366717810 · [email protected]
南京德尔诺医药科技有限公司02585057128;025-86957866 13952093866 · [email protected]
上海陶素生化科技有限公司021-33632979 · [email protected]
Additional notes · 1 item

DefinitionChEBI: D-arginine is a D-alpha-amino acid that is the D-isomer of arginine. It has a role as an EC 4.1.1.19 (arginine decarboxylase) inhibitor and a mouse metabolite. It is a D-alpha-amino acid and an arginine. It is a conjugate base of a D-argininium(1+). It is a conjugate acid of a D-argininate. It is an enantiomer of a L-arginine.