ADDA (amino acid)

Short description: Amino acid in toxins made by cyanobacteria

ADDA

Names
Preferred IUPAC name

(2S,3S,4E,6E,8S,9S)-3-Amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid

Other names

(all-S,all-E)-3-Amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid

Identifiers

CAS Number

* 126456-06-2

3D model (JSmol)

* Interactive image

ChemSpider |

* 20137047

PubChem CID

* 14205264

InChI

* InChI=1S/C20H29NO3/c1-14(10-11-18(21)16(3)20(22)23)12-15(2)19(24-4)13-17-8-6-5-7-9-17/h5-12,15-16,18-19H,13,21H2,1-4H3,(H,22,23)/b11-10+,14-12+/t15-,16-,18-,19-/m0/s1

Key: HJVCHYDYCYBBQX-HLTLHRPFSA-N

* InChI=1/C20H29NO3/c1-14(10-11-18(21)16(3)20(22)23)12-15(2)19(24-4)13-17-8-6-5-7-9-17/h5-12,15-16,18-19H,13,21H2,1-4H3,(H,22,23)/b11-10+,14-12+/t15-,16-,18-,19-/m0/s1

Key: HJVCHYDYCYBBQX-HLTLHRPFBY

SMILES

* OC([C@@H](C)[C@@H](N)/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC1=CC=CC=C1)=O

Properties

Chemical formula

| C20H29NO3
Molar mass | 331.456 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Tracking categories (test):

* SizeSet

ADDA ((all-S,all-E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid) is a non-proteinogenic amino acid found in toxins made by cyanobacteria. Toxins which include this amino acid include microcystins[1] and nodularins.

Along with leucine and arginine, it is found in microcystin-LR, an extremely toxic compound produced by cyanobacteria. In order to treat a water supply contaminated with microcystin-LR, chlorination can be used to oxidize the double bonds of ADDA in order to initiate the chemical breakdown of this compound.[2]

## References

1. ↑ Rudolph-Böhner, Sabine; Mierke, Dale F.; Moroder, Luis (1994). "Molecular structure of the cyanobacterial tumor-promoting microcystins". FEBS Letters 349 (3): 319–323. doi:10.1016/0014-5793(94)00680-6. PMID 8050589.
2. ↑ "ADDA". https://www.acs.org/molecule-of-the-week/archive/a/adda.html.

* v
* t
* e

Non-proteinogenic amino acids

Plant cell wall|

* Hydroxyproline

bacterial cell wall|

* Lanthionine
* Norleucine
* Diaminopimelic acid

neurotransmitters|

* gamma-Aminobutyric acid (GABA)
* Quisqualic acid (toxic)

human toxins|

* ADDA (amino acid)
* Canavanine
* thialysine
* Azetidine-2-carboxylic acid
* Quisqualic acid

Medical/Health|

| Beta-peptides|

* β-Alanine
* β-Leucine

|

Antibiotic|

* 2-Aminoisobutyric acid (AIB)
* Enduracididine

|

clotting factors|

* Carboxyglutamic acid

|

Other|

* 4-Aminobenzoic acid (PABA)
* Aminolevulinic acid (metabolism)
* Canaline (insectiside)
* Penicillamine (chelation)
* Norleucine (Alzheimers)
* Dihydroxyphenylglycine (DHPG)
* Sarcosine
* Norvaline
* Homocysteine (heart)
* Hydroxyproline (collagen)
* Hypusine

|

Abiotic amino acids|

* List of abiotic amino acids

Engineered amino acids|

* Expanded genetic code

Intermediates|

| Mitochondria citric acid cycle|

* Ornithine
* Citrulline

|

* Aminolevulinic acid (5-ALA)
* Cystine

* Amino acids types: Encoded (proteins)
* Essential
* Non-proteinogenic
* Ketogenic
* Glucogenic
* Imino acids
* D-amino acids
* Dehydroamino acids

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