4-{[1-METHYL-2,4-DIOXO-6-(3-PHENYLPROP-1-YN-1-YL)-1,4-DIHYDROQUINAZOLIN-3(2H)-YL]METHYL}BENZOIC ACID

Identification

Generic Name
4-{[1-METHYL-2,4-DIOXO-6-(3-PHENYLPROP-1-YN-1-YL)-1,4-DIHYDROQUINAZOLIN-3(2H)-YL]METHYL}BENZOIC ACID
DrugBank Accession Number
DB07827
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 424.448
Monoisotopic: 424.142307138
Chemical Formula
C26H20N2O4
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCollagenase 3Not 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 quinazolines. These are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazanaphthalenes
Sub Class
Benzodiazines
Direct Parent
Quinazolines
Alternative Parents
Benzoic acids / Benzoyl derivatives / Pyrimidones / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds
show 5 more
Substituents
Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzoic acid / Benzoic acid or derivatives / Benzoyl / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
FLTYDFYSVZBKOB-UHFFFAOYSA-N
InChI
InChI=1S/C26H20N2O4/c1-27-23-15-12-19(9-5-8-18-6-3-2-4-7-18)16-22(23)24(29)28(26(27)32)17-20-10-13-21(14-11-20)25(30)31/h2-4,6-7,10-16H,8,17H2,1H3,(H,30,31)
IUPAC Name
4-{[1-methyl-2,4-dioxo-6-(3-phenylprop-1-yn-1-yl)-1,2,3,4-tetrahydroquinazolin-3-yl]methyl}benzoic acid
SMILES
CN1C(=O)N(CC2=CC=C(C=C2)C(O)=O)C(=O)C2=C1C=CC(=C2)C#CCC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
10224181
PubChem Substance
99444298
ChemSpider
8399672
BindingDB
50265079
ChEMBL
CHEMBL496942
ZINC
ZINC000003815953
PDBe Ligand
GG1
PDB Entries
2ozr

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.00413 mg/mLALOGPS
logP3.79ALOGPS
logP4.78Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)4.07Chemaxon
pKa (Strongest Basic)-7.4Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area77.92 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity119.03 m3·mol-1Chemaxon
Polarizability45.68 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6527
Blood Brain Barrier+0.9017
Caco-2 permeable+0.5192
P-glycoprotein substrateNon-substrate0.6688
P-glycoprotein inhibitor INon-inhibitor0.9274
P-glycoprotein inhibitor IINon-inhibitor0.8321
Renal organic cation transporterNon-inhibitor0.8328
CYP450 2C9 substrateNon-substrate0.6656
CYP450 2D6 substrateNon-substrate0.8699
CYP450 3A4 substrateNon-substrate0.5611
CYP450 1A2 substrateNon-inhibitor0.8305
CYP450 2C9 inhibitorNon-inhibitor0.5072
CYP450 2D6 inhibitorNon-inhibitor0.9386
CYP450 2C19 inhibitorNon-inhibitor0.5713
CYP450 3A4 inhibitorNon-inhibitor0.8854
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7361
Ames testNon AMES toxic0.7285
CarcinogenicityNon-carcinogens0.9021
BiodegradationNot ready biodegradable0.8093
Rat acute toxicity2.4255 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9543
hERG inhibition (predictor II)Non-inhibitor0.8786
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/MSsplash10-056r-0000900000-fc279175ccc788c41e45
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00fs-0379500000-4abae33533031855e207
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-2102900000-a944d2591183c52ed3f6
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0019000000-ae76ac0cb0a28d9ff395
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kf-9843300000-fde2777931fbe79090b6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-015a-0492000000-9ae6a081610c3c9bc203
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]-191.22221
predicted
DeepCCS 1.0 (2019)
[M+H]+193.61778
predicted
DeepCCS 1.0 (2019)
[M+Na]+199.5303
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Collagenase 3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Plays a role in the degradation of extracellular matrix proteins including fibrillar collagen, fibronectin, TNC and ACAN. Cleaves triple helical collagens, including type I, type II and type III co...
Gene Name
MMP13
Uniprot ID
P45452
Uniprot Name
Collagenase 3
Molecular Weight
53819.32 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 21:26 / Updated at June 12, 2020 16:52