T3DB: Daminozide

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation Targets (2)XML

Targets (2)

Record Information

Version

2.0

Creation Date

2013-04-25 07:56:50 UTC

Update Date

2014-12-24 20:26:33 UTC

Accession Number

T3D3821

Identification

Common Name

Daminozide

Class

Small Molecule

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Alar was first approved for use in the U.S. in 1963, it was primarily used on apples until 1989 when it was voluntarily withdrawn by the manufacturer after the U.S. Environmental Protection Agency proposed banning it based on unacceptably high cancer risks to consumers.

Compound Type

Amide
Hydrazine
Industrial/Workplace Toxin
Organic Compound
Pesticide
Plant Growth Regulator
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
N-(Dimethylamino)succinamic acid

Chemical Formula

C₆H₁₂N₂O₃

Average Molecular Mass

160.171 g/mol

Monoisotopic Mass

160.085 g/mol

CAS Registry Number

1596-84-5

IUPAC Name

3-(N',N'-dimethylhydrazinecarbonyl)propanoic acid

Traditional Name

daminozide

SMILES

CN(C)NC(=O)CCC(O)=O

InChI Identifier

InChI=1S/C6H12N2O3/c1-8(2)7-5(9)3-4-6(10)11/h3-4H2,1-2H3,(H,7,9)(H,10,11)

InChI Key

InChIKey=NOQGZXFMHARMLW-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as straight chain fatty acids. These are fatty acids with a straight aliphatic chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Straight chain fatty acids

Alternative Parents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

straight-chain fatty acid (CHEBI:4312 )
Pesticides (C10996 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available
LogP	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	33.9 g/L	ALOGPS
logP	-2.4	ALOGPS
logP	-1.3	ChemAxon
logS	-0.67	ALOGPS
pKa (Strongest Acidic)	4.5	ChemAxon
pKa (Strongest Basic)	2.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	69.64 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	38.45 m³·mol⁻¹	ChemAxon
Polarizability	15.93 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2020-08-04	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 10V, positive	splash10-03di-0900000000-d6f240d17c5245b67c8b	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 20V, positive	splash10-0006-1900000000-04e4a466d12896051550	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 30V, positive	splash10-0006-9200000000-d6cdef6b72ee4f579798	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 40V, positive	splash10-0006-9000000000-ef09b385cfcc52c6c974	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 50V, positive	splash10-0006-9000000000-473eb50c90d24b0d9473	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive	splash10-0006-0900000000-d4c8585ef82a77274880	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-0006-0900000000-f46d521980add5a18b80	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 30V, positive	splash10-0006-0900000000-8b37ae244fcb4f7ecf46	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive	splash10-0006-1900000000-526f8b2152e05d275610	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 10V, negative	splash10-0a4i-0900000000-f9911011475a9c4d8cec	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 20V, negative	splash10-0007-5900000000-4459cd92b0b878efdbf9	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 30V, negative	splash10-0007-9100000000-dcbb6cb3a15e20d759c9	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 40V, negative	splash10-0006-9000000000-724c2141659d50722a65	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ 50V, negative	splash10-0006-9000000000-becb9070a0b026afd99c	2020-08-04	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0900000000-f46d521980add5a18b80	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0006-0900000000-8b37ae244fcb4f7ecf46	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0900000000-d4c8585ef82a77274880	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01ox-0900000000-f02058ff651be72786fc	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0296-5900000000-57ed363e679720f21848	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05di-9100000000-d59a5f871622481a3a4c	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-1900000000-59fbd2e0fa8a23a6e5fd	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4l-9500000000-82d89da0a19635fbe87b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-303a2ac8ee27062a8c2b	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-8900000000-280c40121d0f531d1f4c	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01qc-9200000000-8cb365608df1ffe0738c	2021-10-12	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0a4i-9100000000-eeaa9443ca9163b93152	2014-10-20	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not listed by IARC.

Uses/Sources

This is a man-made compound that is used as a pesticide.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

Not Available

BioCyc ID

Not Available

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Not Available

References

Synthesis Reference

Not Available

MSDS

T3D3821.pdf

General References

Not Available

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Targets

Target Details

1. C-C motif chemokine 2

General Function:: Not Available
Specific Function:: Not Available
Gene Name:: CCL2
Uniprot ID:: P13500
Molecular Weight:: 11024.87 Da

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.48 uM	BSK_SAg_MCP1_up	BioSeek

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 ]

Target Details

2. Urokinase plasminogen activator surface receptor

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

Binding/Activity Constants

Type	Value	Assay Type	Assay Source
AC50	1.48 uM	BSK_3C_uPAR_down	BioSeek
AC50	1.48 uM	BSK_BE3C_uPAR_up	BioSeek

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 ]

Daminozide (T3D3821)

Structure for T3D3821: Daminozide

Targets

Binding/Activity Constants

References

Binding/Activity Constants

References