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N-[(2-AMINO-6-METHYLPYRIMIDIN-4-YL)METHYL]-3-{[(E)-(2-OXODIHYDROFURAN-3(2H)-YLIDENE)METHYL]AMINO}BENZENESULFONAMIDE

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Identification

Generic Name
N-[(2-AMINO-6-METHYLPYRIMIDIN-4-YL)METHYL]-3-{[(E)-(2-OXODIHYDROFURAN-3(2H)-YLIDENE)METHYL]AMINO}BENZENESULFONAMIDE
DrugBank Accession Number
DB07325
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 389.429
Monoisotopic: 389.115774811
Chemical Formula
C17H19N5O4S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHeat shock protein HSP 90-alphaNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminobenzenesulfonamides. These are organic compounds containing a benzenesulfonamide moiety with an amine group attached to the benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Benzenesulfonamides
Direct Parent
Aminobenzenesulfonamides
Alternative Parents
Benzenesulfonyl compounds / Aniline and substituted anilines / Aminopyrimidines and derivatives / Secondary alkylarylamines / Gamma butyrolactones / Organosulfonamides / Vinylogous amides / Aminosulfonyl compounds / Tetrahydrofurans / Enoate esters
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Substituents
Allylamine / Alpha,beta-unsaturated carboxylic ester / Amine / Amino acid or derivatives / Aminobenzenesulfonamide / Aminopyrimidine / Aminosulfonyl compound / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle
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Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
VCOKUBHAJVTVNG-FMIVXFBMSA-N
InChI
InChI=1S/C17H19N5O4S/c1-11-7-14(22-17(18)21-11)10-20-27(24,25)15-4-2-3-13(8-15)19-9-12-5-6-26-16(12)23/h2-4,7-9,19-20H,5-6,10H2,1H3,(H2,18,21,22)/b12-9+
IUPAC Name
N-[(2-amino-6-methylpyrimidin-4-yl)methyl]-3-({[(3E)-2-oxooxolan-3-ylidene]methyl}amino)benzene-1-sulfonamide
SMILES
CC1=NC(N)=NC(CNS(=O)(=O)C2=CC(N\C=C3/CCOC3=O)=CC=C2)=C1

References

General References
Not Available
PubChem Compound
17755582
PubChem Substance
99443796
ChemSpider
22376453
ZINC
ZINC000036966118
PDBe Ligand
A94
PDB Entries
2qg0

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.15 mg/mLALOGPS
logP0.55ALOGPS
logP0.37Chemaxon
logS-3.4ALOGPS
pKa (Strongest Acidic)9.69Chemaxon
pKa (Strongest Basic)4.02Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area136.3 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity101.7 m3·mol-1Chemaxon
Polarizability39.63 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9753
Blood Brain Barrier-0.6497
Caco-2 permeable-0.6529
P-glycoprotein substrateSubstrate0.5289
P-glycoprotein inhibitor INon-inhibitor0.6546
P-glycoprotein inhibitor IINon-inhibitor0.9524
Renal organic cation transporterNon-inhibitor0.6695
CYP450 2C9 substrateNon-substrate0.7412
CYP450 2D6 substrateNon-substrate0.8231
CYP450 3A4 substrateNon-substrate0.5286
CYP450 1A2 substrateNon-inhibitor0.7593
CYP450 2C9 inhibitorNon-inhibitor0.5963
CYP450 2D6 inhibitorNon-inhibitor0.8286
CYP450 2C19 inhibitorNon-inhibitor0.6101
CYP450 3A4 inhibitorNon-inhibitor0.7046
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5386
Ames testNon AMES toxic0.6127
CarcinogenicityNon-carcinogens0.857
BiodegradationNot ready biodegradable0.9964
Rat acute toxicity2.4128 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6625
hERG inhibition (predictor II)Non-inhibitor0.7504
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0009000000-8ec301fe11081669066b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-8136aa68ba1c2014b1ec
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f76-0029000000-47352c7f2b938c7e84ab
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0219000000-843278b59d3fc77caf2f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-052u-1912000000-0843f735e524b402333c
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-2519000000-450d9bb87d959cc80f85
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-188.85065
predicted
DeepCCS 1.0 (2019)
[M+H]+191.20865
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.39784
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Heat shock protein HSP 90-alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Molecular chaperone that promotes the maturation, structural maintenance and proper regulation of specific target proteins involved for instance in cell cycle control and signal transduction. Undergoes a functional cycle that is linked to its ATPase activity which is essential for its chaperone activity. This cycle probably induces conformational changes in the client proteins, thereby causing their activation. Interacts dynamically with various co-chaperones that modulate its substrate recognition, ATPase cycle and chaperone function (PubMed:11274138, PubMed:12526792, PubMed:15577939, PubMed:15937123, PubMed:27353360, PubMed:29127155). Engages with a range of client protein classes via its interaction with various co-chaperone proteins or complexes, that act as adapters, simultaneously able to interact with the specific client and the central chaperone itself (PubMed:29127155). Recruitment of ATP and co-chaperone followed by client protein forms a functional chaperone. After the completion of the chaperoning process, properly folded client protein and co-chaperone leave HSP90 in an ADP-bound partially open conformation and finally, ADP is released from HSP90 which acquires an open conformation for the next cycle (PubMed:26991466, PubMed:27295069). Plays a critical role in mitochondrial import, delivers preproteins to the mitochondrial import receptor TOMM70 (PubMed:12526792). Apart from its chaperone activity, it also plays a role in the regulation of the transcription machinery. HSP90 and its co-chaperones modulate transcription at least at three different levels (PubMed:25973397). In the first place, they alter the steady-state levels of certain transcription factors in response to various physiological cues (PubMed:25973397). Second, they modulate the activity of certain epigenetic modifiers, such as histone deacetylases or DNA methyl transferases, and thereby respond to the change in the environment (PubMed:25973397). Third, they participate in the eviction of histones from the promoter region of certain genes and thereby turn on gene expression (PubMed:25973397). Binds bacterial lipopolysaccharide (LPS) and mediates LPS-induced inflammatory response, including TNF secretion by monocytes (PubMed:11276205). Antagonizes STUB1-mediated inhibition of TGF-beta signaling via inhibition of STUB1-mediated SMAD3 ubiquitination and degradation (PubMed:24613385). Mediates the association of TOMM70 with IRF3 or TBK1 in mitochondrial outer membrane which promotes host antiviral response (PubMed:20628368, PubMed:25609812)
Specific Function
Atp binding
Gene Name
HSP90AA1
Uniprot ID
P07900
Uniprot Name
Heat shock protein HSP 90-alpha
Molecular Weight
84659.015 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:20 / Updated at June 12, 2020 16:52