N-Acetyl-L-tryptophan - ≥98% , CAS No.1218-34-4

CAS: 1218-34-4 Cat. No.: A111003 Molecular Weight: 246.26 Beilstein Registry Number: 22(3/4)6781 EC Number: 214-935-9

GRADE & PURITY ≥98%

Synonyms

Acetyltryptophan, L- | (S)-2-Acetamido-3-(1H-indol-3-yl)propanoic acid | KBio2_006575 | Ac-Trp-OH | N-Acetyl-L-tryptophan, Pharmaceutical Secondary Standard; Certified Reference Material | SPBio_001535 | KBio2_001439 | A-1820 | L-ACETYLTRYPTOPHAN | Spectr

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

 Product Description：

N-Acetyl-L-tryptophan is an endogenous metabolite.

Specifications

Synonyms

Acetyltryptophan, L- | (S)-2-Acetamido-3-(1H-indol-3-yl)propanoic acid | KBio2_006575 | Ac-Trp-OH | N-Acetyl-L-tryptophan, Pharmaceutical Secondary Standard; Certified Reference Material | SPBio_001535 | KBio2_001439 | A-1820 | L-ACETYLTRYPTOPHAN | Spectr

Specifications & Purity

≥98%

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

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

Action Type

INHIBITOR

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504759931
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504759931
• Canonical Smiles: CC(=O)NC(CC1=CNC2=CC=CC=C21)C(=O)O
• IUPAC Name: (2S)-2-acetamido-3-(1H-indol-3-yl)propanoic acid
• InChIKey: DZTHIGRZJZPRDV-LBPRGKRZSA-N
• INCHI: 1S/C13H14N2O3/c1-8(16)15-12(13(17)18)6-9-7-14-11-5-3-2-4-10(9)11/h2-5,7,12,14H,6H2,1H3,(H,15,16)(H,17,18)/t12-/m0/s1
• Isomeric SMILES: CC(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)O
• WGK Germany: 2
• RTECS: YN6160000
• Molecular Weight: 246.26
• Beilstein: 22(3/4)6781
• Reaxy-Rn: 487262
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=487262&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 N-acyl-alpha amino acids and derivatives
              • Level8 N-acyl-alpha amino acids
                • Level9 N-acyl-L-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 - N-acyl-alpha amino acids and derivatives - N-acyl-alpha amino acids
• Direct Parent: N-acyl-L-alpha-amino acids
• Alternative Parents: Indolyl carboxylic acids and derivatives 3-alkylindoles Substituted pyrroles Benzenoids Heteroaromatic compounds Acetamides Secondary carboxylic acid amides Monocarboxylic acids and derivatives Carboxylic acids Azacyclic compounds Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: N-acyl-l-alpha-amino acid - Indolyl carboxylic acid derivative - 3-alkylindole - Indole - Indole or derivatives - Substituted pyrrole - Benzenoid - Acetamide - Heteroaromatic compound - Pyrrole - Carboxamide group - Secondary carboxylic acid amide - Azacycle - Organoheterocyclic compound - Carboxylic acid - Monocarboxylic acid or derivatives - Hydrocarbon derivative - Organonitrogen compound - Organooxygen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organic oxide - Carbonyl group - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
• External Descriptors: N-acetyl-L-amino acid - L-tryptophan derivative

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)

MMP3 Tchem Matrix metalloproteinase 3 (3433 Activities)

Discover Target: MMP3

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

IDO1 Tchem Indoleamine 2,3-dioxygenase (6650 Activities)

Discover Target: IDO1

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

KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

Discover Target: KDM4E

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

SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

Discover Target: SLCO1B1

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

SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

Discover Target: SLCO1B3

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

SLC16A10 SLC16A10 protein (28 Activities)

Discover Target: SLC16A10

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

Associated Targets(non-human)

Cruzipain (33337 Activities)

Explore this target

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: ≥45.1 mg/mL in DMSO; ≥17.3 mg/mL in EtOH; insoluble in H2O
• Sensitivity: light & air sensitive
• Specific Rotation[α]: 26 ° (C=1, 1mol/L NaOH)
• Melt Point(°C): 186°C
• Molecular Weight: 246.260 g/mol
• XLogP3: 1.100
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 246.1 Da
• Monoisotopic Mass: 246.1 Da
• Topological Polar Surface Area: 82.200 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 332.000
• 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. Xiuzhen Qiu, Weimao Chen, Yiling Luo, Yulin Wang, Yanlian Wang, Huishi Guo.  (2019)  Highly sensitive α-amanitin sensor based on molecularly imprinted photonic crystals.  ANALYTICA CHIMICA ACTA,      [PMID:31735207] [10.1016/j.aca.2019.09.066]

2. Qici Wu, Qilei Zhang, Shiwen Xu, Chengtong Ge, Shanjing Yao, Dongqiang Lin.  (2017)  Preparation and evaluation of mixed-mode resins with tryptophan analogues as functional ligands for human serum albumin separation.  CHINESE JOURNAL OF CHEMICAL ENGINEERING,      [PMID:] [10.1016/j.cjche.2016.12.010]

3. Yuting Li, Xiaotong Li, Jinshun Ye, Zhenzhao Weng, Xiaozhen Liu, Fengyuan Liu, Jingkun Yan, Lin Li.  (2024)  Reactivity of amino acid residues towards 4-methylbenzoquinone: Effect on the site-specificity of quinone-protein reaction.  LWT-FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.lwt.2024.116217]