NAV

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

Identification

Generic Name
Bishydroxy[2h-1-Benzopyran-2-One,1,2-Benzopyrone]
DrugBank Accession Number
DB04392
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 336.295
Monoisotopic: 336.063388116
Chemical Formula
C19H12O6
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UNAD(P)H dehydrogenase [quinone] 1Not AvailableHumans
UFMN-dependent NADH-azoreductaseNot AvailableEscherichia coli (strain K12)
UOxygen-insensitive NAD(P)H nitroreductaseNot 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

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 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
1,3-dicarbonyl compound / 3,4-dihydrocoumarin / Aromatic heteropolycyclic compound / Aryl alkyl ketone / Aryl ketone / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Chromone
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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

References

General References
Not Available
PubChem Compound
17753965
PubChem Substance
46508476
ChemSpider
16743957
ZINC
ZINC000012504328
PDBe Ligand
DTC
PDB Entries
1ooq / 2f1o / 2z9c / 4cet / 5fuq

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 Solubility0.0673 mg/mLALOGPS
logP2.37ALOGPS
logP2.69Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)9.83Chemaxon
pKa (Strongest Basic)-6.9Chemaxon
Physiological Charge0Chemaxon
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-MSsplash10-0ab9-2917000000-0d62c3671856b1fa2964
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0009000000-f27454164019e517cbce
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-0694000000-af2fedc1e7ecd2470348
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0079-0918000000-911cfa3f7ca81a698917
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052o-0692000000-c8d152e1a4ff2420c5b2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0901000000-ccc2361823d1e83f2633
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-8930000000-39a02623087c14630653
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]-169.47108
predicted
DeepCCS 1.0 (2019)
[M+H]+171.86665
predicted
DeepCCS 1.0 (2019)
[M+Na]+178.2527
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. NAD(P)H dehydrogenase [quinone] 1
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. [Article]
Details2. FMN-dependent NADH-azoreductase
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. [Article]
Details3. Oxygen-insensitive NAD(P)H nitroreductase
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. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52