(R)-CPP , CAS No.126453-07-4

CAS: 126453-07-4 Cat. No.: C274632 Molecular Weight: 252.21

Synonyms

DTXSID501208909 | STL555719 | BDBM50050704 | SCHEMBL3863705 | UNII-A3QV2VT7SN | SCHEMBL1557957 | 3-((R)-Carboxylpiperazin-4-yl)-propyl-1-phosphonic acid | CPP, (-)- | 7RC | AKOS000119712 | Tocris-0247 | Tocris-0173 | (2R)-4-(3-Phosphonopropyl)-2-piperazin

Storage

Room temperature,Desiccated

Shipped In

Normal

Overview

Store at Room Temperature. Store under desiccating conditions. The product can be stored for up to 12 months.

Specifications

Synonyms

DTXSID501208909 | STL555719 | BDBM50050704 | SCHEMBL3863705 | UNII-A3QV2VT7SN | SCHEMBL1557957 | 3-((R)-Carboxylpiperazin-4-yl)-propyl-1-phosphonic acid | CPP, (-)- | 7RC | AKOS000119712 | Tocris-0247 | Tocris-0173 | (2R)-4-(3-Phosphonopropyl)-2-piperazin

Biochemical and Physiological Mechanisms

Highly potent, competitive NMDA antagonist; more active enantiomer of ( RS )-CPP. (K i values are 0.04, 0.3, 0.6 and 2.0 μM at NR1/NR2A, NR1/NR2B, NR1/NR2C and NR1/NR2D, respectively).

Storage

Room temperature, Desiccated

Shipped In

Normal

Action Type

ANTAGONIST

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. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Names and Identifiers

• Canonical Smiles: C1CN(CC(N1)C(=O)O)CCCP(=O)(O)O
• IUPAC Name: (2R)-4-(3-phosphonopropyl)piperazine-2-carboxylic acid
• InChIKey: CUVGUPIVTLGRGI-SSDOTTSWSA-N
• INCHI: 1S/C8H17N2O5P/c11-8(12)7-6-10(4-2-9-7)3-1-5-16(13,14)15/h7,9H,1-6H2,(H,11,12)(H2,13,14,15)/t7-/m1/s1
• Isomeric SMILES: C1CN(C[C@@H](N1)C(=O)O)CCCP(=O)(O)O
• Molecular Weight: 252.21
• Reaxy-Rn: 4234994
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4234994&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 Alpha amino acids
              • Level8 D-alpha-amino acids

• 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 - Alpha amino acids
• Direct Parent: D-alpha-amino acids
• Alternative Parents: Piperazine carboxylic acids N-alkylpiperazines Organic phosphonic acids Trialkylamines Amino acids Monocarboxylic acids and derivatives Dialkylamines Carboxylic acids Azacyclic compounds Organophosphorus compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: D-alpha-amino acid - Piperazine-2-carboxylic acid - N-alkylpiperazine - 1,4-diazinane - Piperazine - Organophosphonic acid - Organophosphonic acid derivative - Amino acid - Tertiary amine - Tertiary aliphatic amine - Carboxylic acid - Secondary aliphatic amine - Monocarboxylic acid or derivatives - Azacycle - Secondary amine - Organoheterocyclic compound - Organonitrogen compound - Organic oxide - Organic oxygen compound - Carbonyl group - Organooxygen compound - Organophosphorus compound - Hydrocarbon derivative - Amine - Organic nitrogen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as d-alpha-amino acids. These are alpha amino acids which have the D-configuration of the alpha-carbon atom.
• External Descriptors: Not available

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)

CHRM1 Tclin Muscarinic acetylcholine receptor M1 (12690 Activities)

Discover Target: CHRM1

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

THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

Discover Target: THRB

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

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

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

ALOX15 Tchem Arachidonate 15-lipoxygenase (7108 Activities)

Discover Target: ALOX15

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

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

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

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

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

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

Discover Target: CYP2C19

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

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

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

HSD17B10 Tchem Endoplasmic reticulum-associated amyloid beta-peptide-binding protein (20669 Activities)

Discover Target: HSD17B10

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

GRIN1 Tclin Glutamate [NMDA] receptor (933 Activities)

Discover Target: GRIN1

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

Associated Targets(non-human)

Grin1 Glutamate NMDA receptor (6467 Activities)

Discover Target: Grin1

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

Gria2 Glutamate receptor ionotropic, AMPA (2103 Activities)

Discover Target: Gria2

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)

Discover Target: Grin1

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 1 ml water to give specified mM/ml concentration
• Molecular Weight: 252.200 g/mol
• XLogP3: -6.800
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 252.088 Da
• Monoisotopic Mass: 252.088 Da
• Topological Polar Surface Area: 110.000 Ų
• Heavy Atom Count: 16
• Formal Charge: 0
• Complexity: 292.000
• 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. Yiqiao Pei, Ye Zhang, Fang Tian, Yanrong Zhao, Xuguang Zhang, Steve W. Cui, Huali Wang, Jianbo Zhang, Hao Wang.  (2025)  Enhanced Bioavailability of Ferric Pyrophosphate Delivery System Constructed with β-Glucan and Casein Phosphopeptide.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:40600440] [10.1021/acs.jafc.4c13286]