(3R,5Z,8S,9S,11E)-8,9,16-TRIHYDROXY-14-METHOXY-3-METHYL-3,4,9,10-TETRAHYDRO-1H-2-BENZOXACYCLOTETRADECINE-1,7(8H)-DIONE

Identification

Name
(3R,5Z,8S,9S,11E)-8,9,16-TRIHYDROXY-14-METHOXY-3-METHYL-3,4,9,10-TETRAHYDRO-1H-2-BENZOXACYCLOTETRADECINE-1,7(8H)-DIONE
Accession Number
DB07788
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: 362.3738
Monoisotopic: 362.136553058
Chemical Formula
C19H22O7
InChI Key
NEQZWEXWOFPKOT-QHSZRYGNSA-N
InChI
InChI=1S/C19H22O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3-4,6-7,9-11,15,18,21-23H,5,8H2,1-2H3/b6-4+,7-3-/t11-,15+,18-/m1/s1
IUPAC Name
(3R,8S,9S)-8,9,16-trihydroxy-14-methoxy-3-methyl-3,4,7,8,9,10-hexahydro-1H-2-benzoxacyclotetradecine-1,7-dione
SMILES
[H]\C1=C([H])/C2=CC(OC)=CC(O)=C2C(=O)O[[email protected]]([H])(C)C\C([H])=C([H])/C(=O)[[email protected]@]([H])(O)[[email protected]@]([H])(O)C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMitogen-activated protein kinase 1Not AvailableHuman
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
46882177
PubChem Substance
99444259
ChemSpider
24677359
ChEMBL
CHEMBL1079087
HET
FRR

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 Solubility0.33 mg/mLALOGPS
logP1.75ALOGPS
logP2.57ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.59ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity96.77 m3·mol-1ChemAxon
Polarizability36.66 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9408
Blood Brain Barrier-0.7072
Caco-2 permeable-0.5676
P-glycoprotein substrateSubstrate0.7018
P-glycoprotein inhibitor INon-inhibitor0.7143
P-glycoprotein inhibitor IINon-inhibitor0.9384
Renal organic cation transporterNon-inhibitor0.9655
CYP450 2C9 substrateNon-substrate0.8318
CYP450 2D6 substrateNon-substrate0.8731
CYP450 3A4 substrateNon-substrate0.5717
CYP450 1A2 substrateNon-inhibitor0.7269
CYP450 2C9 inhibitorNon-inhibitor0.9444
CYP450 2D6 inhibitorNon-inhibitor0.9243
CYP450 2C19 inhibitorNon-inhibitor0.9238
CYP450 3A4 inhibitorNon-inhibitor0.8181
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9803
Ames testAMES toxic0.5418
CarcinogenicityNon-carcinogens0.9594
BiodegradationReady biodegradable0.5766
Rat acute toxicity2.5633 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.979
hERG inhibition (predictor II)Non-inhibitor0.9259
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 zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Macrolides and analogues
Sub Class
Zearalenones
Direct Parent
Zearalenones
Alternative Parents
Anisoles / Alkyl aryl ethers / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Vinylogous acids / Secondary alcohols / Lactones / Cyclic ketones / Carboxylic acid esters / 1,2-diols
show 3 more
Substituents
Zearalenone-skeleton / Anisole / Phenol ether / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Phenol / Benzenoid / Vinylogous acid / Cyclic ketone
show 17 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Rna polymerase ii carboxy-terminal domain kinase activity
Specific Function
Serine/threonine kinase which acts as an essential component of the MAP kinase signal transduction pathway. MAPK1/ERK2 and MAPK3/ERK1 are the 2 MAPKs which play an important role in the MAPK/ERK ca...
Gene Name
MAPK1
Uniprot ID
P28482
Uniprot Name
Mitogen-activated protein kinase 1
Molecular Weight
41389.265 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 15:25 / Updated on December 01, 2017 15:55