(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
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Identification
- Generic 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
- DrugBank Accession Number
- DB07788
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 362.3738
Monoisotopic: 362.136553058 - Chemical Formula
- C19H22O7
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UMitogen-activated protein kinase 1 Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 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
- 1,2-diol / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Alcohol / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Benzenoid / Carbonyl group / Carboxylic acid derivative show 17 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
- 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,5Z,8S,9S,11E)-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[C@]([H])(C)C\C([H])=C([H])/C(=O)[C@@]([H])(O)[C@@]([H])(O)C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 46882177
- PubChem Substance
- 99444259
- ChemSpider
- 24677359
- ChEMBL
- CHEMBL1079087
- ZINC
- ZINC000102051776
- PDBe Ligand
- FRR
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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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
Property Value Source Water Solubility 0.33 mg/mL ALOGPS logP 1.75 ALOGPS logP 2.57 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 9.59 Chemaxon pKa (Strongest Basic) -3.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 113.29 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 96.77 m3·mol-1 Chemaxon Polarizability 36.66 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9408 Blood Brain Barrier - 0.7072 Caco-2 permeable - 0.5676 P-glycoprotein substrate Substrate 0.7018 P-glycoprotein inhibitor I Non-inhibitor 0.7143 P-glycoprotein inhibitor II Non-inhibitor 0.9384 Renal organic cation transporter Non-inhibitor 0.9655 CYP450 2C9 substrate Non-substrate 0.8318 CYP450 2D6 substrate Non-substrate 0.8731 CYP450 3A4 substrate Non-substrate 0.5717 CYP450 1A2 substrate Non-inhibitor 0.7269 CYP450 2C9 inhibitor Non-inhibitor 0.9444 CYP450 2D6 inhibitor Non-inhibitor 0.9243 CYP450 2C19 inhibitor Non-inhibitor 0.9238 CYP450 3A4 inhibitor Non-inhibitor 0.8181 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9803 Ames test AMES toxic 0.5418 Carcinogenicity Non-carcinogens 0.9594 Biodegradation Ready biodegradable 0.5766 Rat acute toxicity 2.5633 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.979 hERG inhibition (predictor II) Non-inhibitor 0.9259
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0002-0009000000-1ffab4f760f407d4d47e Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004j-0009000000-956c51a521018aa7b03a Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004j-0009000000-fe0754677e045a93f7bb Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-03di-0009000000-53c2d3fb4209d48a9987 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0029000000-cf0f2d61c502f7c1fcd3 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01t9-0009000000-0956aaac90c44298e281 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0029000000-534dd0e466f0aec3104a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 182.33638 predictedDeepCCS 1.0 (2019) [M+H]+ 184.62675 predictedDeepCCS 1.0 (2019) [M+Na]+ 190.37895 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsMitogen-activated protein kinase 1
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General 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 cascade. They participate also in a signaling cascade initiated by activated KIT and KITLG/SCF. Depending on the cellular context, the MAPK/ERK cascade mediates diverse biological functions such as cell growth, adhesion, survival and differentiation through the regulation of transcription, translation, cytoskeletal rearrangements. The MAPK/ERK cascade also plays a role in initiation and regulation of meiosis, mitosis, and postmitotic functions in differentiated cells by phosphorylating a number of transcription factors. About 160 substrates have already been discovered for ERKs. Many of these substrates are localized in the nucleus, and seem to participate in the regulation of transcription upon stimulation. However, other substrates are found in the cytosol as well as in other cellular organelles, and those are responsible for processes such as translation, mitosis and apoptosis. Moreover, the MAPK/ERK cascade is also involved in the regulation of the endosomal dynamics, including lysosome processing and endosome cycling through the perinuclear recycling compartment (PNRC); as well as in the fragmentation of the Golgi apparatus during mitosis. The substrates include transcription factors (such as ATF2, BCL6, ELK1, ERF, FOS, HSF4 or SPZ1), cytoskeletal elements (such as CANX, CTTN, GJA1, MAP2, MAPT, PXN, SORBS3 or STMN1), regulators of apoptosis (such as BAD, BTG2, CASP9, DAPK1, IER3, MCL1 or PPARG), regulators of translation (such as EIF4EBP1 and FXR1) and a variety of other signaling-related molecules (like ARHGEF2, DCC, FRS2 or GRB10). Protein kinases (such as RAF1, RPS6KA1/RSK1, RPS6KA3/RSK2, RPS6KA2/RSK3, RPS6KA6/RSK4, SYK, MKNK1/MNK1, MKNK2/MNK2, RPS6KA5/MSK1, RPS6KA4/MSK2, MAPKAPK3 or MAPKAPK5) and phosphatases (such as DUSP1, DUSP4, DUSP6 or DUSP16) are other substrates which enable the propagation the MAPK/ERK signal to additional cytosolic and nuclear targets, thereby extending the specificity of the cascade. Mediates phosphorylation of TPR in response to EGF stimulation. May play a role in the spindle assembly checkpoint. Phosphorylates PML and promotes its interaction with PIN1, leading to PML degradation. Phosphorylates CDK2AP2 (By similarity)
- Specific Function
- ATP binding
- Gene Name
- MAPK1
- Uniprot ID
- P28482
- Uniprot Name
- Mitogen-activated protein kinase 1
- Molecular Weight
- 41389.265 Da
References
- 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 21:25 / Updated at June 12, 2020 16:52