Bishydroxy[2h-1-Benzopyran-2-One,1,2-Benzopyrone]

Identification

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Name
Bishydroxy[2h-1-Benzopyran-2-One,1,2-Benzopyrone]
Accession Number
DB04392  (EXPT01281)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 336.295
Monoisotopic: 336.063388116
Chemical Formula
C19H12O6
InChI Key
HIZKPJUTKKJDGA-BETUJISGSA-N
InChI
InChI=1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,12-13H,9H2/t12-,13+
IUPAC Name
(3R)-3-{[(3S)-2,4-dioxo-3,4-dihydro-2H-1-benzopyran-3-yl]methyl}-3,4-dihydro-2H-1-benzopyran-2,4-dione
SMILES
[H][C@@]1(C[C@@]2([H])C(=O)OC3=C(C=CC=C3)C2=O)C(=O)OC2=CC=CC=C2C1=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UOxygen-insensitive NAD(P)H nitroreductaseNot AvailableEscherichia coli (strain K12)
UNAD(P)H dehydrogenase [quinone] 1Not AvailableHumans
UFMN-dependent NADH-azoreductaseNot AvailableEscherichia coli (strain K12)
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
17753965
PubChem Substance
46508476
ChemSpider
16743957
HET
DTC
PDB Entries
1ooq / 2f1o / 2z9c / 4cet / 5fuq

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.0673 mg/mLALOGPS
logP2.37ALOGPS
logP2.69ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)2.06ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area86.74 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity85.33 m3·mol-1ChemAxon
Polarizability32.8 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9636
Blood Brain Barrier+0.9662
Caco-2 permeable+0.6911
P-glycoprotein substrateNon-substrate0.6244
P-glycoprotein inhibitor INon-inhibitor0.7482
P-glycoprotein inhibitor IINon-inhibitor0.7794
Renal organic cation transporterNon-inhibitor0.8766
CYP450 2C9 substrateNon-substrate0.8183
CYP450 2D6 substrateNon-substrate0.8655
CYP450 3A4 substrateNon-substrate0.7398
CYP450 1A2 substrateInhibitor0.5225
CYP450 2C9 inhibitorInhibitor0.8705
CYP450 2D6 inhibitorNon-inhibitor0.9369
CYP450 2C19 inhibitorNon-inhibitor0.6001
CYP450 3A4 inhibitorNon-inhibitor0.7138
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7063
Ames testNon AMES toxic0.9558
CarcinogenicityNon-carcinogens0.9442
BiodegradationNot ready biodegradable0.7144
Rat acute toxicity2.7494 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8798
hERG inhibition (predictor II)Non-inhibitor0.9664
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as chromones. These are compounds containing a benzopyran-4-one moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzopyrans
Sub Class
1-benzopyrans
Direct Parent
Chromones
Alternative Parents
3,4-dihydrocoumarins / Aryl alkyl ketones / Dicarboxylic acids and derivatives / Benzenoids / 1,3-dicarbonyl compounds / Lactones / Carboxylic acid esters / Oxacyclic compounds / Organic oxides / Hydrocarbon derivatives
Substituents
3,4-dihydrocoumarin / Chromone / Aryl alkyl ketone / Aryl ketone / Dicarboxylic acid or derivatives / 1,3-dicarbonyl compound / Benzenoid / Carboxylic acid ester / Ketone / Lactone
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Nad(p)h nitroreductase activity
Specific Function
Reduction of a variety of nitroaromatic compounds using NADH (and to lesser extent NADPH) as source of reducing equivalents; two electrons are transferred. Capable of reducing nitrofurazone, quinon...
Gene Name
nfsB
Uniprot ID
P38489
Uniprot Name
Oxygen-insensitive NAD(P)H nitroreductase
Molecular Weight
23904.99 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. 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. [PubMed:10592235]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Superoxide dismutase activity
Specific Function
The enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vit...
Gene Name
NQO1
Uniprot ID
P15559
Uniprot Name
NAD(P)H dehydrogenase [quinone] 1
Molecular Weight
30867.405 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. [PubMed:10592235]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Unknown
General Function
Oxidoreductase activity, acting on nad(p)h, quinone or similar compound as acceptor
Specific Function
Catalyzes the reductive cleavage of azo bond in aromatic azo compounds to the corresponding amines. Requires NADH, but not NADPH, as an electron donor for its activity. The enzyme can reduce ethyl ...
Gene Name
azoR
Uniprot ID
P41407
Uniprot Name
FMN-dependent NADH-azoreductase
Molecular Weight
21657.47 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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 06:05