DAMGO TFA - Moligand™, ≥99% , CAS No.950492-85-0

CAS: 950492-85-0 Cat. No.: D650262 Molecular Weight: 627.61

GRADE & PURITY Moligand™, ≥99%

Synonyms

HB2409 | H-Tyr-D-Ala-Gly-N(Me)Phe-Gly-ol | Tyr-D-Ala-Gly-N(CH3)Phe-Gly-ol | (2S)-2-[[2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]-methylamino]-N-(2-hydroxyethyl)-3-phenylpropanamide | 158: PN: US20030176421 PAGE: 54

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

DAMGO TFA is a μ-opioid receptor ( μ-OPR ) selective agonist with a K d of 3.46 nM for native μ-OPR.

In Vitro

DAMGO (1-10 μM) TFA significantly reduces the activation of neuronal Akt and ERK1/2 by CXCL12 and inhibits CXCL12-promoted neuronal survival, but does not down-regulate CXCR4 protein expression. DAMGO (1 μM) TFA effectively inhibits the prostaglandin E 2 (PGE 2) induced increase in a tetrodotoxin-resistant voltage-gated Na + current (TTX-R I Na ), i.e. PGE 2 (1 μM) can increase the TTX-R I Na peak by 103 % compared to 24.9 % with the addition of DAMGO. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

DAMGO (i.v., 0.5-2 mg/kg) TFA can produce significant anti-injury effects on injured paws of male Sprague-Dawley rats weighing 200-225 g in a dose-dependent manner, producing an effective and long-lasting analgesic effect. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

Sequence: Tyr- {d-Ala}-Gly-{Me-Phe}-Gly-ol

Specifications

Synonyms

HB2409 | H-Tyr-D-Ala-Gly-N(Me)Phe-Gly-ol | Tyr-D-Ala-Gly-N(CH3)Phe-Gly-ol | (2S)-2-[[2-[[(2R)-2-[[(2S)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]propanoyl]amino]acetyl]-methylamino]-N-(2-hydroxyethyl)-3-phenylpropanamide | 158: PN: US20030176421 PAGE: 54

Specifications & Purity

Moligand™, ≥99%

Biochemical and Physiological Mechanisms

DAMGO TFA is a μ-opioid receptor ( μ-OPR ) selective agonist with a K d of 3.46 nM for native μ-OPR.

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Action Type

AGONIST

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CC(C(=O)NCC(=O)N(C)C(CC1=CC=CC=C1)C(=O)NCCO)NC(=O)C(CC2=CC=C(C=C2)O)N
• IUPAC Name: (2S)-2-amino-N-[(2R)-1-[[2-[[(2S)-1-(2-hydroxyethylamino)-1-oxo-3-phenylpropan-2-yl]-methylamino]-2-oxoethyl]amino]-1-oxopropan-2-yl]-3-(4-hydroxyphenyl)propanamide
• InChIKey: HPZJMUBDEAMBFI-WTNAPCKOSA-N
• INCHI: 1S/C26H35N5O6/c1-17(30-25(36)21(27)14-19-8-10-20(33)11-9-19)24(35)29-16-23(34)31(2)22(26(37)28-12-13-32)15-18-6-4-3-5-7-18/h3-11,17,21-22,32-33H,12-16,27H2,1-2H3,(H,28,37)(H,29,35)(H,30,36)/t17-,21+,22+/m1/s1
• Isomeric SMILES: C[C@H](C(=O)NCC(=O)N(C)[C@@H](CC1=CC=CC=C1)C(=O)NCCO)NC(=O)[C@H](CC2=CC=C(C=C2)O)N
• Alternate CAS: 78123-71-4
• MeSH Entry Terms: 2 Ala 4 MePhe 5 Gly Enkephalin;2-Ala-4-MePhe-5-Gly-Enkephalin;Ala(2)-MePhe(4)-Gly-ol(5) Enkephalin;D Ala2 NMe Phe4 Gly ol Enkephalin;D-Ala(2)-MePhe(4)-Gly-ol(5) Enkephalin;D-Ala2-NMe-Phe4-Gly-ol Enkephalin;DAGO;DAGOL;DAMGE;DAMGO;Enkephalin, Ala(2)-MePhe(4
• Molecular Weight: 627.61
• Reaxy-Rn: 25226561
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25226561&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 Peptides
          • Level6 Oligopeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Oligopeptides
• Alternative Parents: Tyrosine and derivatives Phenylalanine and derivatives N-acyl-alpha amino acids and derivatives Alpha amino acid amides Alanine and derivatives Amphetamines and derivatives N-acylethanolamines 1-hydroxy-2-unsubstituted benzenoids Aralkylamines Fatty amides Tertiary carboxylic acid amides Secondary carboxylic acid amides Primary alcohols Organopnictogen compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Alpha-oligopeptide - Tyrosine or derivatives - Phenylalanine or derivatives - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Alanine or derivatives - N-substituted-alpha-amino acid - Alpha-amino acid or derivatives - Amphetamine or derivatives - N-acylethanolamine - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Aralkylamine - Fatty acyl - Benzenoid - Monocyclic benzene moiety - Fatty amide - Tertiary carboxylic acid amide - Secondary carboxylic acid amide - Amino acid or derivatives - Carboxamide group - Alkanolamine - Primary amine - Primary aliphatic amine - Organic oxide - Hydrocarbon derivative - Carbonyl group - Organonitrogen compound - Organopnictogen compound - Organooxygen compound - Amine - Organic oxygen compound - Alcohol - Primary alcohol - Organic nitrogen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
• External Descriptors: peptide

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)

CCKBR Tclin Gastrin/cholecystokinin type B receptor (2 Activities)

Discover Target: CCKBR

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

OPRD1 Tclin Delta-type opioid receptor (3 Activities)

Discover Target: OPRD1

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

OPRM1 Tclin Mu-type opioid receptor (92 Activities)

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

CNR1 Tclin Cannabinoid CB1 receptor (20913 Activities)

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

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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

OPRM1 Tclin Mu opioid receptor (19785 Activities)

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

OPRD1 Tclin Delta opioid receptor (15096 Activities)

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OPRK1 Tclin Kappa opioid receptor (16155 Activities)

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OPRL1 Tchem Nociceptin receptor (3823 Activities)

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

TACR1 Tclin Neurokinin 1 receptor (6273 Activities)

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

CCKBR Tclin Cholecystokinin B receptor (3550 Activities)

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

MIA PaCa-2 (5949 Activities)

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KISS1R Tchem Metastin receptor (613 Activities)

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QRFPR Tchem Pyroglutamylated RFamide peptide receptor (276 Activities)

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SLCO1A2 Tchem Solute carrier organic anion transporter family member 1A2 (104 Activities)

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

OPRD1 Tclin Opioid receptors; mu & delta (1530 Activities)

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

OPRK1 Tclin Opioid receptors; delta & kappa (935 Activities)

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

OPRK1 Tclin Opioid receptors; mu/kappa/delta (568 Activities)

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UMSCC1 (87 Activities)

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Associated Targets(non-human)

Sigmar1 Sigma opioid receptor (160 Activities)

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Adcy2 Adenylate cyclase type II (26 Activities)

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Abcb1b P-glycoprotein 1 (174 Activities)

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Cavia porcellus (23802 Activities)

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Mus musculus (284745 Activities)

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Rattus norvegicus (775804 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Oprm1 Opioid receptors; mu and delta (70 Activities)

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Tmem97 Sigma intracellular receptor 2 (922 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: H2O : 125 mg/mL (199.17 mM; Need ultrasonic)
• Sensitivity: Moisture sensitive
• Molecular Weight: 513.600 g/mol
• XLogP3: 0.200
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 13
• Exact Mass: 513.259 Da
• Monoisotopic Mass: 513.259 Da
• Topological Polar Surface Area: 174.000 Ų
• Heavy Atom Count: 37
• Formal Charge: 0
• Complexity: 752.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• 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