(3AS,4R,9BR)-4-(4-HYDROXYPHENYL)-6-(METHOXYMETHYL)-1,2,3,3A,4,9B-HEXAHYDROCYCLOPENTA[C]CHROMEN-8-OL
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Identification
- Generic Name
- (3AS,4R,9BR)-4-(4-HYDROXYPHENYL)-6-(METHOXYMETHYL)-1,2,3,3A,4,9B-HEXAHYDROCYCLOPENTA[C]CHROMEN-8-OL
- DrugBank Accession Number
- DB08020
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 326.3863
Monoisotopic: 326.151809192 - Chemical Formula
- C20H22O4
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UEstrogen receptor beta Not Available Humans UEstrogen receptor alpha 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 6-hydroxyflavonoids. These are flavonoids that bear one hydroxyl group at the C-6 position of the flavonoid skeleton.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Flavonoids
- Sub Class
- Hydroxyflavonoids
- Direct Parent
- 6-hydroxyflavonoids
- Alternative Parents
- 4'-hydroxyflavonoids / Flavans / 1-benzopyrans / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Oxacyclic compounds / Dialkyl ethers / Hydrocarbon derivatives
- Substituents
- 1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 4'-hydroxyflavonoid / 6-hydroxyflavonoid / Alkyl aryl ether / Aromatic heteropolycyclic compound / Benzenoid / Benzopyran / Chromane / Dialkyl ether
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- RHQLNMNKTIOREN-AOIWGVFYSA-N
- InChI
- InChI=1S/C20H22O4/c1-23-11-13-9-15(22)10-18-16-3-2-4-17(16)19(24-20(13)18)12-5-7-14(21)8-6-12/h5-10,16-17,19,21-22H,2-4,11H2,1H3/t16-,17+,19+/m1/s1
- IUPAC Name
- (2R,6S,7R)-7-(4-hydroxyphenyl)-10-(methoxymethyl)-8-oxatricyclo[7.4.0.0^{2,6}]trideca-1(9),10,12-trien-12-ol
- SMILES
- [H][C@@]12CCC[C@]1([H])[C@@]([H])(OC1=C2C=C(O)C=C1COC)C1=CC=C(O)C=C1
References
- General References
- Not Available
- External Links
- PubChem Compound
- 9927355
- PubChem Substance
- 99444491
- ChemSpider
- 8102988
- BindingDB
- 19987
- ChEMBL
- CHEMBL236086
- ZINC
- ZINC000006716343
- PDBe Ligand
- JJ3
- PDB Entries
- 2jj3 / 2qe4
Clinical Trials
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 0.0128 mg/mL ALOGPS logP 3.73 ALOGPS logP 3.99 Chemaxon logS -4.4 ALOGPS pKa (Strongest Acidic) 9.31 Chemaxon pKa (Strongest Basic) -4.1 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 58.92 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 92.06 m3·mol-1 Chemaxon Polarizability 35.46 Å3 Chemaxon Number of Rings 4 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 + 0.9859 Blood Brain Barrier + 0.8761 Caco-2 permeable + 0.6816 P-glycoprotein substrate Substrate 0.77 P-glycoprotein inhibitor I Non-inhibitor 0.8307 P-glycoprotein inhibitor II Inhibitor 0.8266 Renal organic cation transporter Non-inhibitor 0.7008 CYP450 2C9 substrate Non-substrate 0.7277 CYP450 2D6 substrate Non-substrate 0.7568 CYP450 3A4 substrate Substrate 0.5427 CYP450 1A2 substrate Inhibitor 0.8087 CYP450 2C9 inhibitor Inhibitor 0.7613 CYP450 2D6 inhibitor Non-inhibitor 0.5574 CYP450 2C19 inhibitor Inhibitor 0.8069 CYP450 3A4 inhibitor Inhibitor 0.6842 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8466 Ames test Non AMES toxic 0.6656 Carcinogenicity Non-carcinogens 0.9504 Biodegradation Not ready biodegradable 0.8722 Rat acute toxicity 2.7459 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7734 hERG inhibition (predictor II) Non-inhibitor 0.6178
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-004j-0049000000-b3b70d39ff8200eaa8b2 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-0039000000-8b630295ba8a94b41286 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-004i-0029000000-268aff9c89e31520365a Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-004j-0092000000-625f3ed7f67145927783 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-05i1-0693000000-8f21cb02a23a2dfc7dc9 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-055r-0391000000-977ed67712a4f04dc3ad 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]- 178.52704 predictedDeepCCS 1.0 (2019) [M+H]+ 180.92259 predictedDeepCCS 1.0 (2019) [M+Na]+ 186.83513 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsEstrogen receptor beta
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent m...
- Gene Name
- ESR2
- Uniprot ID
- Q92731
- Uniprot Name
- Estrogen receptor beta
- Molecular Weight
- 59215.765 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]
2. DetailsEstrogen receptor alpha
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 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 21:27 / Updated at June 12, 2020 16:52