Lyngbyatoxin A
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Basic Info
| Common Name | Lyngbyatoxin A(F05229) |
| 2D Structure | |
| Description | Lyngbyatoxin A is a cyanotoxin produced by certain cyanobacteria species, notably <i>Moorea producens</i> (formerly classified as <i>Lyngbya majuscula</i>). It is used as a defensive secretion to protect this cyanobacteria from predation by fish, being a potent irritant and vesicant, as well as a carcinogen. Low concentrations more commonly encountered cause milder symptoms, known as seaweed dermatitis. The toxin is highly inflammatory and vesicatory. It is also a strong tumor promoter through activation of protein kinase C. |
| FRCD ID | F05229 |
| CAS Number | 70497-14-2 |
| PubChem CID | 3979 |
| Formula | C27H39N3O2 |
| IUPAC Name | None |
| InChI Key | KISDGNGREAJPQR-UHFFFAOYSA-N |
| InChI | InChI=1S/C27H39N3O2/c1-8-27(6,13-9-10-17(2)3)21-11-12-22-23-19(15-28-24(21)23)14-20(16-31)29-26(32)25(18(4)5)30(22)7/h8,10-12,15,18,20,25,28,31H,1,9,13-14,16H2,2-7H3,(H,29,32) |
| Canonical SMILES | CC(C)C1C(=O)NC(CC2=CNC3=C(C=CC(=C23)N1C)C(C)(CCC=C(C)C)C=C)CO |
| Isomeric SMILES | CC(C)C1C(=O)NC(CC2=CNC3=C(C=CC(=C23)N1C)C(C)(CCC=C(C)C)C=C)CO |
| Synonyms |
Lyngbyatoxin A, Micromonospora sp.
9-[1-Ethenyl-1,5-dimethyl-4-hexenyl]-1,2,4,5,6,8-hexahydro-5-(hydroxymethyl)-1-methyl-2-isopropyl-3H-pyrrolo[4,3,2-gh]-1,4-benzodiazonin-3-one
lyngbyatoxin a
GNF-Pf-3063
CHEBI:80050
AC1L1H55
CHEMBL581451
C15720
|
| Classifies |
Bacterial Toxin
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| 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 | Alpha amino acid amides |
| Alternative Parents | |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Alpha-amino acid amide - Aromatic monoterpenoid - Monoterpenoid - 3-alkylindole - Indole - Indole or derivatives - Tertiary aliphatic/aromatic amine - Dialkylarylamine - Benzenoid - Heteroaromatic compound - Pyrrole - Tertiary amine - Secondary carboxylic acid amide - Carboxamide group - Lactam - Organoheterocyclic compound - Azacycle - Alcohol - Organonitrogen compound - Hydrocarbon derivative - Organooxygen compound - Organic oxide - Organopnictogen compound - Primary alcohol - Carbonyl group - Organic oxygen compound - Amine - Organic nitrogen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 437.628 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 3 |
| Rotatable Bond Count | 7 |
| Complexity | 701 |
| Monoisotopic Mass | 437.304 |
| Exact Mass | 437.304 |
| XLogP | 6.2 |
| Formal Charge | 0 |
| Heavy Atom Count | 32 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 3 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.5279 |
| Human Intestinal Absorption | HIA+ | 0.9815 |
| Caco-2 Permeability | Caco2- | 0.6470 |
| P-glycoprotein Substrate | Substrate | 0.7932 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.6867 |
| Non-inhibitor | 0.5218 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8457 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.3931 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8300 |
| CYP450 2D6 Substrate | Non-substrate | 0.8032 |
| CYP450 3A4 Substrate | Substrate | 0.7146 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6133 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.6450 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8178 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.6856 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.6788 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.6268 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9888 |
| Non-inhibitor | 0.7894 | |
| AMES Toxicity | Non AMES toxic | 0.6889 |
| Carcinogens | Non-carcinogens | 0.9313 |
| Fish Toxicity | High FHMT | 0.9389 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8708 |
| Honey Bee Toxicity | Low HBT | 0.6498 |
| Biodegradation | Not ready biodegradable | 0.9937 |
| Acute Oral Toxicity | III | 0.5581 |
| Carcinogenicity (Three-class) | Non-required | 0.6359 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.8649 | LogS |
| Caco-2 Permeability | 0.6428 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 2.8501 | LD50, mol/kg |
| Fish Toxicity | 1.2250 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.3293 | pIGC50, ug/L |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| A new lyngbyatoxin from the Hawaiian cyanobacterium Moorea producens. | Mar Drugs | 2014 May 12 | 24824022 |
| Two new lyngbyatoxin derivatives from the Cyanobacterium, Moorea producens. | Mar Drugs | 2014 Dec 1 | 25470181 |
| Chemical defenses: from compounds to communities. | Biol Bull | 2007 Dec | 18083964 |
| The fate of Lyngbya majuscula toxins in three potential consumers. | J Chem Ecol | 2005 Jul | 16222795 |
| Comparison of the partition coefficient and skin penetration of a marine algal toxin (lyngbyatoxin A). | Food Chem Toxicol | 1992 Sep | 1427518 |
| Studies on environmental chemical carcinogenesis in Japan. | Science | 1986 Jul 18 | 3088728 |
Targets
- General Function:
- Protein homodimerization activity
- Specific Function:
- Key enzyme of polyamine biosynthesis that converts ornithine into putrescine, which is the precursor for the polyamines, spermidine and spermine.
- Gene Name:
- ODC1
- Uniprot ID:
- P11926
- Molecular Weight:
- 51147.73 Da
References
- Fujiki H, Mori M, Nakayasu M, Terada M, Sugimura T, Moore RE: Indole alkaloids: dihydroteleocidin B, teleocidin, and lyngbyatoxin A as members of a new class of tumor promoters. Proc Natl Acad Sci U S A. 1981 Jun;78(6):3872-6. [6791164 ]
References
- Jiang W, Zhou W, Uchida H, Kikumori M, Irie K, Watanabe R, Suzuki T, Sakamoto B, Kamio M, Nagai H: A new lyngbyatoxin from the Hawaiian cyanobacterium Moorea producens. Mar Drugs. 2014 May 12;12(5):2748-59. doi: 10.3390/md12052748. [24824022 ]