Daminozide
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Basic Info
| Common Name | Daminozide(F05052) |
| 2D Structure | |
| Description | Daminozide — also known as Alar, Kylar, B-NINE, DMASA, SADH, or B 995 — is a plant growth regulator, a chemical sprayed on fruit to regulate their growth, make their harvest easier, and keep apples from falling off the trees before they are ripe. This makes sure they are red and firm for storage. Alar was first approved for use in the U.S. in 1963, it was primarily used on apples until 1989 when it was voluntarily withdrawn by the manufacturer after the U.S. Environmental Protection Agency proposed banning it based on unacceptably high cancer risks to consumers. |
| FRCD ID | F05052 |
| CAS Number | 1596-84-5 |
| PubChem CID | 15331 |
| Formula | C6H12N2O3 |
| IUPAC Name | 4-(2,2-dimethylhydrazinyl)-4-oxobutanoic acid |
| InChI Key | NOQGZXFMHARMLW-UHFFFAOYSA-N |
| InChI | InChI=1S/C6H12N2O3/c1-8(2)7-5(9)3-4-6(10)11/h3-4H2,1-2H3,(H,7,9)(H,10,11) |
| Canonical SMILES | CN(C)NC(=O)CCC(=O)O |
| Isomeric SMILES | CN(C)NC(=O)CCC(=O)O |
| Synonyms |
N-(Dimethylamino)succinamic acid
Daminozide
1596-84-5
Kylar
ALAR
DMASA
Aminozide
SADH
Succinic acid 2,2-dimethylhydrazide
B-Nine
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Lipids and lipid-like molecules |
| Class | Fatty Acyls |
| Subclass | Fatty acids and conjugates |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Straight chain fatty acids |
| Alternative Parents | |
| Molecular Framework | Aliphatic acyclic compounds |
| Substituents | Straight chain fatty acid - Carboxylic acid hydrazide - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic acyclic compound |
| Description | This compound belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 160.173 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 4 |
| Complexity | 156 |
| Monoisotopic Mass | 160.085 |
| Exact Mass | 160.085 |
| XLogP | -3.1 |
| Formal Charge | 0 |
| Heavy Atom Count | 11 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| 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+ | 0.9380 |
| Human Intestinal Absorption | HIA+ | 0.8057 |
| Caco-2 Permeability | Caco2- | 0.6546 |
| P-glycoprotein Substrate | Non-substrate | 0.6920 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.8595 |
| Non-inhibitor | 0.9575 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9543 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8460 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8078 |
| CYP450 2D6 Substrate | Non-substrate | 0.8240 |
| CYP450 3A4 Substrate | Non-substrate | 0.5596 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9114 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9107 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9530 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9400 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.9351 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9962 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9817 |
| Non-inhibitor | 0.9466 | |
| AMES Toxicity | Non AMES toxic | 0.9133 |
| Carcinogens | Non-carcinogens | 0.7069 |
| Fish Toxicity | Low FHMT | 0.6231 |
| Tetrahymena Pyriformis Toxicity | Low TPT | 0.8633 |
| Honey Bee Toxicity | Low HBT | 0.8746 |
| Biodegradation | Not ready biodegradable | 0.7021 |
| Acute Oral Toxicity | IV | 0.6196 |
| Carcinogenicity (Three-class) | Warning | 0.5210 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -0.2626 | LogS |
| Caco-2 Permeability | 0.3336 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.3110 | LD50, mol/kg |
| Fish Toxicity | 2.0223 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | -0.8079 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Oil fruits | 0402000 | European Union | 0.1* | 26/04/2017 | |
| Fat | 1015020 | European Union | 0.06* | 26/04/2017 | |
| Brassica vegetables (excluding brassica roots and brassica baby leaf crops) | 0240000 | European Union | 0.06* | 26/04/2017 | |
| (a) flowering brassica | 0241000 | European Union | 0.06* | 26/04/2017 | |
| Hemp seeds | 0401140 | European Union | 0.1* | 26/04/2017 | |
| Citrus fruits | 0110000 | European Union | 0.06* | 26/04/2017 | |
| Grapefruits (Natsudaidais, Shaddocks/pomelos, Sweeties/oroblancos, Tangelolos, Tangelos (except minneolas)/Ugli®, Other hybrids of Citrus paradisi, not elsewhere mentioned,) | 0110010 | European Union | 0.06* | 26/04/2017 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.06* | 26/04/2017 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.06* | 26/04/2017 | |
| Limes (Indian sweet limes/Palestine sweet limes, Kaffir limes, Sweet limes/mosambis, Tahiti limes, Limequats,) | 0110040 | European Union | 0.06* | 26/04/2017 | |
| Mandarins (Calamondins, Clementines, Cleopatra mandarins, Minneolas, Satsumas/clausellinas, Tangerines/dancy mandarins, Tangors, Other hybrids of Citrus reticulata, not elsewhere mentioned,) | 0110050 | European Union | 0.06* | 26/04/2017 | |
| Others (2) | 0110990 | European Union | 0.06* | 26/04/2017 | |
| Tree nuts | 0120000 | European Union | 0.1* | 26/04/2017 | |
| Almonds (Apricot kernels, Bitter almonds, Canarium nuts/galip nuts, Pili nuts, Okari nuts,) | 0120010 | European Union | 0.1* | 26/04/2017 | |
| Brazil nuts | 0120020 | European Union | 0.1* | 26/04/2017 | |
| Cashew nuts | 0120030 | European Union | 0.1* | 26/04/2017 | |
| Chestnuts | 0120040 | European Union | 0.1* | 26/04/2017 | |
| Coconuts (Areca nuts/betel nuts,) | 0120050 | European Union | 0.1* | 26/04/2017 | |
| Hazelnuts/cobnuts (Acorns, Filberts,) | 0120060 | European Union | 0.1* | 26/04/2017 | |
| Macadamias | 0120070 | European Union | 0.1* | 26/04/2017 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Rapid determination of polar pesticides and plant growth regulators in fruits andvegetables by liquid chromatography/tandem mass spectrometry. | J Environ Sci Health B | 2018 May 22:1-10 | 29787687 |
| Multi-residue analysis of pesticides, plant hormones, veterinary drugs and mycotoxins using HILIC chromatography - MS/MS in various food matrices. | Anal Chim Acta | 2016 Oct 26 | 27720116 |
| Rapid detection of pesticides not amenable to multi-residue methods by flowinjection-tandem mass spectrometry. | Anal Bioanal Chem | 2014 Nov | 24518902 |
| Feasibility of using terahertz spectroscopy to detect seven different pesticides in wheat flour. | J Food Prot | 2014 Dec | 25474054 |
| Quartz crystal microbalance for the determination of daminozide using molecularlyimprinted polymers as recognition element. | Biosens Bioelectron | 2007 Jan 15 | 16621501 |
| Categorizing mistaken false positives in regulation of human and environmental health. | Risk Anal | 2007 Feb | 17362413 |
| Determination of daminozide residues in apple pulp using HPLC-DAD-UV. | J Agric Food Chem | 2001 Aug | 11513626 |
| Determination of daminozide in apples and apple leaves by liquidchromatography--mass spectrometry. | J Chromatogr A | 1999 Feb 12 | 10074699 |
| Postharvest-applied agrochemicals and their residues in fresh fruits andvegetables. | J Assoc Off Anal Chem | 1991 Sep-Oct | 1783584 |
| Modified gas chromatographic/mass spectrometric method for determination ofdaminozide in high protein food products. | J Assoc Off Anal Chem | 1991 Jul-Aug | 1917816 |
| Improved gas chromatographic method for determination of daminozide by alkalinehydrolysis and 2-nitrobenzaldehyde derivatization and survey results ofdaminozide in agricultural products. | J Assoc Off Anal Chem | 1990 Jul-Aug | 2211471 |
| Determination of daminozide in apples by gas chromatography/chemical ionizationmass spectrometry. | J Assoc Off Anal Chem | 1989 Nov-Dec | 2592322 |
| Pesticides and food safety. | Regul Toxicol Pharmacol | 1989 Apr | 2655038 |
Targets
- Gene Name:
- CCL2
- Uniprot ID:
- P13500
- Molecular Weight:
- 11024.87 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Urokinase plasminogen activator receptor activity
- Specific Function:
- Acts as a receptor for urokinase plasminogen activator. Plays a role in localizing and promoting plasmin formation. Mediates the proteolysis-independent signal transduction activation effects of U-PA. It is subject to negative-feedback regulation by U-PA which cleaves it into an inactive form.
- Gene Name:
- PLAUR
- Uniprot ID:
- Q03405
- Molecular Weight:
- 36977.62 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]