L-TRYPTOPHAN
General Information
| Mainterm | L-TRYPTOPHAN |
| Doc Type | ASP |
| CAS Reg.No.(or other ID) | 73-22-3 |
| Regnum |
172.320 |
From www.fda.gov
Computed Descriptors
Download SDF| 2D Structure | |
| CID | 6305 |
| IUPAC Name | (2S)-2-amino-3-(1H-indol-3-yl)propanoic acid |
| InChI | InChI=1S/C11H12N2O2/c12-9(11(14)15)5-7-6-13-10-4-2-1-3-8(7)10/h1-4,6,9,13H,5,12H2,(H,14,15)/t9-/m0/s1 |
| InChI Key | QIVBCDIJIAJPQS-VIFPVBQESA-N |
| Canonical SMILES | C1=CC=C2C(=C1)C(=CN2)CC(C(=O)O)N |
| Molecular Formula | C11H12N2O2 |
| Wikipedia | L-Tryptophan |
From Pubchem
Computed Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 204.229 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 3 |
| Complexity | 245.0 |
| CACTVS Substructure Key Fingerprint | A A A D c c B z M A A A A A A A A A A A A A A A A A A A A W A A A A A w A A A A A A A A A F g B 8 A A A H g A Q C A A A D C j B n g Q 8 y P L J k g C o A z T 3 T A C C g C A x A i A I 2 a G 4 Z J g K I P L A k Z G E Y A h k k A D I y A e Y 2 f K O g A A A A A A C A A A A A A A A A A Q A A A A A A A A A A A = = |
| Topological Polar Surface Area | 79.1 |
| Monoisotopic Mass | 204.09 |
| Exact Mass | 204.09 |
| Compound Is Canonicalized | True |
| Formal Charge | 0 |
| Heavy Atom Count | 15 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
From Pubchem
Food Additives Biosynthesis/Degradation
ADMET Predicted Profile --- Classification
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9510 |
| Human Intestinal Absorption | HIA+ | 0.9840 |
| Caco-2 Permeability | Caco2- | 0.5943 |
| P-glycoprotein Substrate | Non-substrate | 0.5988 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9951 |
| Non-inhibitor | 0.9779 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8805 |
| Distribution | ||
| Subcellular localization | Lysosome | 0.3925 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8463 |
| CYP450 2D6 Substrate | Non-substrate | 0.7897 |
| CYP450 3A4 Substrate | Non-substrate | 0.7841 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9531 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9481 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9307 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9644 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9432 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9542 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9864 |
| Non-inhibitor | 0.9402 | |
| AMES Toxicity | Non AMES toxic | 0.9284 |
| Carcinogens | Non-carcinogens | 0.9310 |
| Fish Toxicity | High FHMT | 0.6819 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.6688 |
| Honey Bee Toxicity | Low HBT | 0.6838 |
| Biodegradation | Not ready biodegradable | 0.8348 |
| Acute Oral Toxicity | IV | 0.6272 |
| Carcinogenicity (Three-class) | Non-required | 0.7121 |
From admetSAR
ADMET Predicted Profile --- Regression
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -1.2926 | LogS |
| Caco-2 Permeability | 0.1091 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.1785 | LD50, mol/kg |
| Fish Toxicity | 2.1566 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.3419 | pIGC50, ug/L |
From admetSAR
Toxicity Profile
| Route of Exposure | None |
|---|---|
| Mechanism of Toxicity | A number of important side reactions occur during the catabolism of tryptophan on the pathway to acetoacetate. The first enzyme of the catabolic pathway is an iron porphyrin oxygenase that opens the indole ring. The latter enzyme is highly inducible, its concentration rising almost 10-fold on a diet high in tryptophan. Kynurenine is the first key branch point intermediate in the pathway. Kynurenine undergoes deamniation in a standard transamination reaction yielding kynurenic acid. Kynurenic acid and metabolites have been shown to act as antiexcitotoxics and anticonvulsives. A second side branch reaction produces anthranilic acid plus alanine. Another equivalent of alanine is produced further along the main catabolic pathway, and it is the production of these alanine residues that allows tryptophan to be classified among the glucogenic and ketogenic amino acids. The second important branch point converts kynurenine into 2-amino-3-carboxymuconic semialdehyde, which has two fates. The main flow of carbon elements from this intermediate is to glutarate. An important side reaction in liver is a transamination and several rearrangements to produce limited amounts of nicotinic acid, which leads to production of a small amount of NAD<sup>+</sup> and NADP<sup>+</sup>. |
| Metabolism | Hepatic. |
| Toxicity Values | None |
| Lethal Dose | None |
| Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
| Minimum Risk Level | None |
| Health Effects | None |
| Treatment | None |
| Reference |
|
From T3DB
Taxonomic Classification
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Indoles and derivatives |
| Subclass | Indolyl carboxylic acids and derivatives |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Indolyl carboxylic acids and derivatives |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Indolyl carboxylic acid derivative - Alpha-amino acid - Alpha-amino acid or derivatives - L-alpha-amino acid - 3-alkylindole - Indole - Aralkylamine - Benzenoid - Substituted pyrrole - Heteroaromatic compound - Pyrrole - Amino acid or derivatives - Amino acid - Carboxylic acid derivative - Carboxylic acid - Monocarboxylic acid or derivatives - Azacycle - Amine - Primary aliphatic amine - Hydrocarbon derivative - Organic oxide - Organic oxygen compound - Organic nitrogen compound - Carbonyl group - Organonitrogen compound - Organooxygen compound - Primary amine - Organopnictogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. These are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. |
From ClassyFire
Targets
- General Function:
- Tryptophan-trna ligase activity
- Specific Function:
- Isoform 1, isoform 2 and T1-TrpRS have aminoacylation activity while T2-TrpRS lacks it. Isoform 2, T1-TrpRS and T2-TrpRS possess angiostatic activity whereas isoform 1 lacks it. T2-TrpRS inhibits fluid shear stress-activated responses of endothelial cells. Regulates ERK, Akt, and eNOS activation pathways that are associated with angiogenesis, cytoskeletal reorganization and shear stress-responsive gene expression.
- Gene Name:
- WARS
- Uniprot ID:
- P23381
- Molecular Weight:
- 53164.91 Da
References
- Yang XL, Otero FJ, Ewalt KL, Liu J, Swairjo MA, Kohrer C, RajBhandary UL, Skene RJ, McRee DE, Schimmel P: Two conformations of a crystalline human tRNA synthetase-tRNA complex: implications for protein synthesis. EMBO J. 2006 Jun 21;25(12):2919-29. Epub 2006 May 25. [16724112 ]
- General Function:
- Tryptophan-trna ligase activity
- Gene Name:
- WARS2
- Uniprot ID:
- Q9UGM6
- Molecular Weight:
- 40146.265 Da
References
- Charriere F, Helgadottir S, Horn EK, Soll D, Schneider A: Dual targeting of a single tRNA(Trp) requires two different tryptophanyl-tRNA synthetases in Trypanosoma brucei. Proc Natl Acad Sci U S A. 2006 May 2;103(18):6847-52. Epub 2006 Apr 24. [16636268 ]
- General Function:
- Pyrophosphatase activity
- Specific Function:
- This isozyme may play a role in skeletal mineralization.
- Gene Name:
- ALPL
- Uniprot ID:
- P05186
- Molecular Weight:
- 57304.435 Da
References
- Lanier M, Sergienko E, Simao AM, Su Y, Chung T, Millan JL, Cashman JR: Design and synthesis of selective inhibitors of placental alkaline phosphatase. Bioorg Med Chem. 2010 Jan 15;18(2):573-9. doi: 10.1016/j.bmc.2009.12.012. Epub 2009 Dec 11. [20031422 ]
- General Function:
- Zinc ion binding
- Gene Name:
- ALPI
- Uniprot ID:
- P09923
- Molecular Weight:
- 56811.695 Da
References
- Lanier M, Sergienko E, Simao AM, Su Y, Chung T, Millan JL, Cashman JR: Design and synthesis of selective inhibitors of placental alkaline phosphatase. Bioorg Med Chem. 2010 Jan 15;18(2):573-9. doi: 10.1016/j.bmc.2009.12.012. Epub 2009 Dec 11. [20031422 ]
- General Function:
- Phospholipase a2 activator activity
- Specific Function:
- Involved in the maintenance of ubiquitin levels.
- Gene Name:
- PLAA
- Uniprot ID:
- Q9Y263
- Molecular Weight:
- 87156.21 Da
References
- Lanier M, Sergienko E, Simao AM, Su Y, Chung T, Millan JL, Cashman JR: Design and synthesis of selective inhibitors of placental alkaline phosphatase. Bioorg Med Chem. 2010 Jan 15;18(2):573-9. doi: 10.1016/j.bmc.2009.12.012. Epub 2009 Dec 11. [20031422 ]
- General Function:
- Tryptophan 2,3-dioxygenase activity
- Specific Function:
- Incorporates oxygen into the indole moiety of tryptophan. Has a broad specificity towards tryptamine and derivatives including D- and L-tryptophan, 5-hydroxytryptophan and serotonin (By similarity).
- Gene Name:
- TDO2
- Uniprot ID:
- P48775
- Molecular Weight:
- 47871.215 Da
References
- Dolusic E, Larrieu P, Moineaux L, Stroobant V, Pilotte L, Colau D, Pochet L, Van den Eynde B, Masereel B, Wouters J, Frederick R: Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators. J Med Chem. 2011 Aug 11;54(15):5320-34. doi: 10.1021/jm2006782. Epub 2011 Jul 18. [21726069 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Can degrade fibronectin, laminin, gelatins of type I, III, IV, and V; collagens III, IV, X, and IX, and cartilage proteoglycans. Activates procollagenase.
- Gene Name:
- MMP3
- Uniprot ID:
- P08254
- Molecular Weight:
- 53976.84 Da
References
- Ye QZ, Johnson LL, Nordan I, Hupe D, Hupe L: A recombinant human stromelysin catalytic domain identifying tryptophan derivatives as human stromelysin inhibitors. J Med Chem. 1994 Jan 7;37(1):206-9. [8289198 ]
- General Function:
- Tryptophan-trna ligase activity
- Gene Name:
- trpS
- Uniprot ID:
- P00953
- Molecular Weight:
- 37192.385 Da
From T3DB