D-Serine - Moligand™, ≥98.5% , Agonist of GluN1;Agonist of GluN2A;Agonist of GluN2B;Agonist of GluN2C;Agonist of GluN2D, CAS No.312-84-5, Agonist of GluN1;Agonist of GluN2A;Agonist of GluN2B;Agonist of GluN2C;Agonist of GluN2D

CAS: 312-84-5 Cat. No.: S105977 Molecular Weight: 105.09 Beilstein Registry Number: 1721403 EC Number: 206-229-4

GRADE & PURITY Moligand™, ≥98.5%

Synonyms

D-Ser | (R)-Serine | D-(+)-Serine;d-serine;D-2-Amino-3-hydroxypropionic acid; (R)-2-Amino-3-hydroxypropionic acid | N-(Butylaminocarbonyl)-4-hydroxymethylbenzenesulfonamide | A20674 | C00740 | s6224 | NCGC00094363-10 | NCGC00094363-07 | NCGC00261773-01 |

Storage

Room temperature

Shipped In

Normal

Overview

D-serine has been used as a substrate in D-amino acid oxidase (DAO) activity in human 1321N1 astrocytoma cells. It has also been used in intracerebroventricular administration in rat for the induction of antinociceptive effect.

D-serine has been used to prevent glycine-dependent desensitization of N-methyl D-aspartate receptor (NMDAR) and to study its effects on NMDARs to correct behavioral abnormalities in rats after partial sciatic nerve ligation (PSNL)

product description：

D-serine is an unusual amino acid expressed in the mammalian brain.D-serine is a dextro amino acid present in neurons, astrocytes, and microglia. It is synthesized from L-serine by the enzyme serine racemase. Racemase also catalyzes the breakdown of D-serine into ammonia and pyruvate. It is oxidized to hydroxypyruvate by D-amino acid oxidase.

application：

D-Serine is involved in the biosynthesis of purines, pyrimidines, and other amino acids. D-Serine also is an agonist of glycine site of the NMDA-type glutamate receptor. It also acts as Lacosamide intermediate.

Specifications

Synonyms

D-Ser | (R)-Serine | D-(+)-Serine;d-serine;D-2-Amino-3-hydroxypropionic acid; (R)-2-Amino-3-hydroxypropionic acid | N-(Butylaminocarbonyl)-4-hydroxymethylbenzenesulfonamide | A20674 | C00740 | s6224 | NCGC00094363-10 | NCGC00094363-07 | NCGC00261773-01 |

Specifications & Purity

Moligand™, ≥98.5%

Biochemical and Physiological Mechanisms

Agonist at the NMDA glycine binding site and the inhibitory post-synaptic glycine receptor.

Storage

Room temperature

Shipped In

Normal

Grade

Moligand™

Action Type

AGONIST

Mechanism of action

Agonist of GluN1;Agonist of GluN2A;Agonist of GluN2B;Agonist of GluN2C;Agonist of GluN2D

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Refer to SDS for further information Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98.5%

Names and Identifiers

• Pubchem Sid: 488184641
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488184641
• Canonical Smiles: C(C(C(=O)O)N)O
• IUPAC Name: (2R)-2-amino-3-hydroxypropanoic acid
• InChIKey: MTCFGRXMJLQNBG-UWTATZPHSA-N
• INCHI: 1S/C3H7NO3/c4-2(1-5)3(6)7/h2,5H,1,4H2,(H,6,7)/t2-/m1/s1
• Isomeric SMILES: C([C@H](C(=O)O)N)O
• WGK Germany: 3
• Molecular Weight: 105.09
• Beilstein: 1721403
• Reaxy-Rn: 1721402
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1721402&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Serine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Serine and derivatives
• Alternative Parents: D-alpha-amino acids Beta hydroxy acids and derivatives Amino acids Monocarboxylic acids and derivatives Carboxylic acids Primary alcohols Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Serine or derivatives - Alpha-amino acid - D-alpha-amino acid - Beta-hydroxy acid - Hydroxy acid - Amino acid - Carboxylic acid - Monocarboxylic acid or derivatives - Alcohol - Primary amine - Primary alcohol - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Primary aliphatic amine - Organic oxide - Organopnictogen compound - Carbonyl group - Organic oxygen compound - Amine - Organic nitrogen compound - Aliphatic acyclic compound
• Description: This compound belongs to the class of organic compounds known as serine and derivatives. These are compounds containing serine or a derivative thereof resulting from reaction of serine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Other amino acids

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

GRIN1 Tclin Glutamate receptor ionotropic, NMDA 1 (0 Activities)

Discover Target: GRIN1

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GRIN2A Tclin Glutamate receptor ionotropic, NMDA 2A (0 Activities)

Discover Target: GRIN2A

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GRIN2B Tclin Glutamate receptor ionotropic, NMDA 2B (0 Activities)

Discover Target: GRIN2B

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GRIN2C Tclin Glutamate receptor ionotropic, NMDA 2C (0 Activities)

Discover Target: GRIN2C

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GRIN2D Tclin Glutamate receptor ionotropic, NMDA 2D (0 Activities)

Discover Target: GRIN2D

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

GRIN1 Tclin Glutamate (NMDA) receptor subunit zeta 1 (122 Activities)

Discover Target: GRIN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC1A4 Tbio Neutral amino acid transporter A (18 Activities)

Discover Target: SLC1A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cortex (4 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

Discover Target: EHMT2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

Discover Target: TDP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LMNA Tbio Prelamin-A/C (36751 Activities)

Discover Target: LMNA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

BLM Tchem Bloom syndrome protein (4248 Activities)

Discover Target: BLM

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)

Discover Target: RGS4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC36A1 Tchem Proton-coupled amino acid transporter 1 (102 Activities)

Discover Target: SLC36A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GRIN1 Tclin Ionotropic glutamate receptor NMDA 1/2D (23 Activities)

Discover Target: GRIN1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

SLC1A5 Tchem Neutral amino acid transporter B(0) (65 Activities)

Discover Target: SLC1A5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Staphylococcus aureus (210822 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mus musculus (284745 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rattus norvegicus (775804 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pfk 6-phospho-1-fructokinase (7870 Activities)

Discover Target: pfk

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

Discover Target: Txnrd1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cerebellum (165 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Grin1 Glutamate NMDA receptor (6467 Activities)

Discover Target: Grin1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc16a10 Monocarboxylate transporter 10 (73 Activities)

Discover Target: Slc16a10

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Grin1 Glutamate NMDA receptor; Grin1/Grin2b (1028 Activities)

Discover Target: Grin1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Grin1 Glutamate NMDA receptor; Grin1/Grin2a (798 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Grin1 Glutamate NMDA receptor; Grin1/Grin2c (1127 Activities)

Discover Target: Grin1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc1a5 Amino acid transporter (271 Activities)

Discover Target: Slc1a5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Slc7a10 Asc-type amino acid transporter 1 (14 Activities)

Discover Target: Slc7a10

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (346 mg/ml at 20°C), and mineral acids. Insoluble in alcohol, ether, and benzene.
• Specific Rotation[α]: -15 ° (C=10, HCl(1+5))
• Melt Point(°C): 220°C
• Molecular Weight: 105.090 g/mol
• XLogP3: -3.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 105.043 Da
• Monoisotopic Mass: 105.043 Da
• Topological Polar Surface Area: 83.600 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 72.600
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yiyi Liu, Fangling Wu, Jiabin Wang, Ling Pu, Chuan-Fan Ding.  (2022)  Simultaneous chirality separation of amino acids and their derivative by natamycin based on mobility measurements.  ANALYTICA CHIMICA ACTA,      [PMID:36089312] [10.1016/j.aca.2022.340298]

2. Shutong Yang, Liancheng Gu, Fangling Wu, Xinhua Dai, Fuxing Xu, Qiaoyu Li, Xiang Fang, Shaoning Yu, Chuan-Fan Ding.  (2022)  The chirality determination of amino acids by forming complexes with cyclodextrins and metal ions using ion mobility spectrometry, and a DFT calculation.  TALANTA,      [PMID:35272154] [10.1016/j.talanta.2022.123363]

3. Chengyi Xie, Liancheng Gu, Qidi Wu, Lei Li, Chenlu Wang, Jiancheng Yu, Keqi Tang.  (2020)  Effective Chiral Discrimination of Amino Acids through Oligosaccharide Incorporation by Trapped Ion Mobility Spectrometry.  ANALYTICAL CHEMISTRY,      [PMID:33226780] [10.1021/acs.analchem.0c03461]

4. Yanni Miao, Qi Liu, Wei Wang, Li Liu, Li Wang.  (2017)  Enantioseparation of amino acids by micellar capillary electrophoresis using binary chiral selectors and determination of D-glutamic acid and D-aspartic acid in rice wine.  JOURNAL OF LIQUID CHROMATOGRAPHY & RELATED TECHNOLOGIES,      [PMID:] [10.1080/10826076.2017.1364263]

5. En Zhang, Peng-Yan Bai, De-Yun Cui, Wen-Chao Chu, Yong-Gang Hua, Qin Liu, Hai-Yang Yin, Yong-Jie Zhang, Shangshang Qin, Hong-Min Liu.  (2017)  Synthesis and bioactivities study of new antibacterial peptide mimics: The dialkyl cationic amphiphiles.  EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,      [PMID:29126736] [10.1016/j.ejmech.2017.10.044]

6. Fangqin Wang, Wenrong Cai, Lilan Tan, Junyao Li, Datong Wu, Yong Kong.  (2024)  A Liquid–Liquid Interfacial Strategy for Construction of Electroactive Chiral Covalent–Organic Frameworks with the Aim to Enlarge the Testing Scope of Chiral Electroanalysis.  ANALYTICAL CHEMISTRY,      [PMID:38335728] [10.1021/acs.analchem.3c05744]

7. Dongbo Wang, Jingting Sang, Mingyang Wang, Dawei Luo, Dandan Han, Bowen Zhang, Jingtao Wang, Junbo Gong.  (2024)  Direct crystallization resolution of chiral compounds assisted by chiral ionic liquids through conformational matching.  SEPARATION AND PURIFICATION TECHNOLOGY,      [PMID:] [10.1016/j.seppur.2024.130912]

8. Chen Chao, Ma Yinglin, Yao Kunda, Ji Qingmin, Liu Wei.  (2024)  Enantioselective adsorption on chiral ceramics with medium entropy.  Nature Communications,  15  (1): (1-11).  [PMID:39572550] [10.1038/s41467-024-54414-8]

9. Wenchan Deng, Chundan Ye, Wei Wang, Rongrong Huang, Cheng Guo, Yuanjiang Pan, Cuirong Sun.  (2024)  LC-MS analysis of chiral amino acids in human urine reveals D-amino acids as potential biomarkers for colorectal cancer.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:39121519] [10.1016/j.jchromb.2024.124270]

10. Lilan Tan, Wenrong Cai, Fangqin Wang, Junyao Li, Datong Wu, Yong Kong.  (2024)  Postsynthetic Modification Strategy for Constructing Electrochemiluminescence-Active Chiral Covalent Organic Frameworks Performing Efficient Enantioselective Sensing.  ANALYTICAL CHEMISTRY,      [PMID:38394220] [10.1021/acs.analchem.3c05887]