(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-4H-chromen-4-one

Identification

Name
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-2,3-dihydro-4H-chromen-4-one
Accession Number
DB08517
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
3O38P61299
CAS number
Not Available
Weight
Average: 286.2794
Monoisotopic: 286.084123558
Chemical Formula
C16H14O5
InChI Key
DJOJDHGQRNZXQQ-AWEZNQCLSA-N
InChI
InChI=1S/C16H14O5/c1-20-11-6-12(18)16-13(19)8-14(21-15(16)7-11)9-2-4-10(17)5-3-9/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1
IUPAC Name
(2S)-5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-3,4-dihydro-2H-1-benzopyran-4-one
SMILES
[H][C@]1(CC(=O)C2=C(O1)C=C(OC)C=C2O)C1=CC=C(O)C=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZNot AvailableHelicobacter pylori
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
Human Metabolome Database
HMDB0030090
KEGG Compound
C09833
PubChem Compound
73571
PubChem Substance
99444988
ChemSpider
66249
BindingDB
50312648
ChEBI
28927
ChEMBL
CHEMBL448297
HET
SAK
PDB Entries
3d04

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 Solubility0.0883 mg/mLALOGPS
logP2.86ALOGPS
logP2.98ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area75.99 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.77 m3·mol-1ChemAxon
Polarizability29.41 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9766
Blood Brain Barrier+0.5181
Caco-2 permeable+0.8947
P-glycoprotein substrateSubstrate0.6554
P-glycoprotein inhibitor INon-inhibitor0.8472
P-glycoprotein inhibitor IINon-inhibitor0.6215
Renal organic cation transporterNon-inhibitor0.8624
CYP450 2C9 substrateNon-substrate0.7155
CYP450 2D6 substrateNon-substrate0.8555
CYP450 3A4 substrateNon-substrate0.5552
CYP450 1A2 substrateInhibitor0.9497
CYP450 2C9 inhibitorInhibitor0.955
CYP450 2D6 inhibitorInhibitor0.5
CYP450 2C19 inhibitorInhibitor0.96
CYP450 3A4 inhibitorInhibitor0.5657
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7541
Ames testNon AMES toxic0.5285
CarcinogenicityNon-carcinogens0.9356
BiodegradationNot ready biodegradable0.8698
Rat acute toxicity3.3571 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9589
hERG inhibition (predictor II)Non-inhibitor0.8793
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
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0gdr-1950300000-a48312953ffcce6caa36
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-056r-2951400000-d20272b440111f7a94e8
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 7-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
O-methylated flavonoids
Direct Parent
7-O-methylated flavonoids
Alternative Parents
Flavanones / 5-hydroxyflavonoids / 4'-hydroxyflavonoids / Chromones / Aryl alkyl ketones / Anisoles / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives
show 4 more
Substituents
7-methoxyflavonoid-skeleton / Flavanone / 4'-hydroxyflavonoid / 5-hydroxyflavonoid / Hydroxyflavonoid / Flavan / Chromone / Benzopyran / Chromane / 1-benzopyran
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monomethoxyflavanone, dihydroxyflavanone, flavonoid phytoalexin (CHEBI:28927) / flavanones (C09833) / Flavanones (LMPK12140571)

Targets

Kind
Protein
Organism
Helicobacter pylori
Pharmacological action
Unknown
General Function
3-hydroxyoctanoyl-[acyl-carrier-protein] dehydratase activity
Specific Function
Involved in unsaturated fatty acids biosynthesis. Catalyzes the dehydration of short chain beta-hydroxyacyl-ACPs and long chain saturated and unsaturated beta-hydroxyacyl-ACPs.Involved in unsaturat...
Gene Name
fabZ
Uniprot ID
Q5G940
Uniprot Name
3-hydroxyacyl-[acyl-carrier-protein] dehydratase FabZ
Molecular Weight
18184.08 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 September 15, 2010 15:32 / Updated on November 02, 2018 06:50