3,4-dihydroxy-9,10-secoandrosta-1(10),2,4-triene-9,17-dione
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Identification
- Generic Name
- 3,4-dihydroxy-9,10-secoandrosta-1(10),2,4-triene-9,17-dione
- DrugBank Accession Number
- DB08542
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 316.3915
Monoisotopic: 316.167459256 - Chemical Formula
- C19H24O4
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UIron-dependent extradiol dioxygenase Not Available Mycobacterium tuberculosis - 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 catechols. These are compounds containing a 1,2-benzenediol moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Phenols
- Sub Class
- Benzenediols
- Direct Parent
- Catechols
- Alternative Parents
- Para cresols / Meta cresols / Toluenes / 1-hydroxy-4-unsubstituted benzenoids / 1-hydroxy-2-unsubstituted benzenoids / Cyclic ketones / Organic oxides / Hydrocarbon derivatives
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / Aromatic homopolycyclic compound / Carbonyl group / Catechol / Cyclic ketone / Hydrocarbon derivative / Ketone / M-cresol / Monocyclic benzene moiety
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- seco-androstane (CHEBI:15896) / C19 steroids (androgens) and derivatives (C04793) / C19 steroids (androgens) and derivatives (LMST02020062)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- YUHVBHDSVLKFNI-NJSLBKSFSA-N
- InChI
- InChI=1S/C19H24O4/c1-11-3-7-16(21)18(23)12(11)4-5-13-14-6-8-17(22)19(14,2)10-9-15(13)20/h3,7,13-14,21,23H,4-6,8-10H2,1-2H3/t13-,14-,19-/m0/s1
- IUPAC Name
- (3aS,4S,7aS)-4-[2-(2,3-dihydroxy-6-methylphenyl)ethyl]-7a-methyl-octahydro-1H-indene-1,5-dione
- SMILES
- [H][C@@]12CCC(=O)[C@@]1(C)CCC(=O)[C@@]2([H])CCC1=C(O)C(O)=CC=C1C
References
- General References
- Not Available
- External Links
- PDB Entries
- 2zi8
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 0.0306 mg/mL ALOGPS logP 3.17 ALOGPS logP 4.15 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 9.44 Chemaxon pKa (Strongest Basic) -6.3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 74.6 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 88.19 m3·mol-1 Chemaxon Polarizability 34.68 Å3 Chemaxon Number of Rings 3 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 + 0.962 Blood Brain Barrier + 0.7847 Caco-2 permeable + 0.5804 P-glycoprotein substrate Substrate 0.7897 P-glycoprotein inhibitor I Non-inhibitor 0.9333 P-glycoprotein inhibitor II Non-inhibitor 0.7947 Renal organic cation transporter Non-inhibitor 0.8566 CYP450 2C9 substrate Non-substrate 0.7855 CYP450 2D6 substrate Non-substrate 0.8582 CYP450 3A4 substrate Substrate 0.7282 CYP450 1A2 substrate Inhibitor 0.5084 CYP450 2C9 inhibitor Non-inhibitor 0.9293 CYP450 2D6 inhibitor Non-inhibitor 0.9454 CYP450 2C19 inhibitor Non-inhibitor 0.8942 CYP450 3A4 inhibitor Non-inhibitor 0.8099 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9218 Ames test Non AMES toxic 0.8248 Carcinogenicity Non-carcinogens 0.9284 Biodegradation Not ready biodegradable 0.9908 Rat acute toxicity 2.0618 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9516 hERG inhibition (predictor II) Inhibitor 0.6414
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-000t-0391000000-6679687601cef5a7ae17 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0039000000-70f72bda1ec3501e1219 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0390000000-95bee9c8ea8c7dd6638e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-014j-0964000000-284a890263699e644369 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0970-1950000000-848df71a376e6f725faa Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-074i-0910000000-2d486a36610c6244c5b6 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]- 178.44151 predictedDeepCCS 1.0 (2019) [M+H]+ 180.83708 predictedDeepCCS 1.0 (2019) [M+Na]+ 186.74959 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsIron-dependent extradiol dioxygenase
- Kind
- Protein
- Organism
- Mycobacterium tuberculosis
- Pharmacological action
- Unknown
- General Function
- Catalyzes the meta-cleavage of 3,4-dihydroxy-9,10-seconandrost-1,3,5(10)-triene-9,17-dione (3,4-DHSA) to produce 4,5-9,10-diseco-3-hydroxy-5,9,17-trioxoandrosta-1(10),2-diene-4-oic acid (4,9-DSHA).
- Specific Function
- 3,4-dihydroxy-9,10-secoandrosta-1,3,5(10)-triene-9,17-dione 4,5-dioxygenase activity
- Gene Name
- hsaC
- Uniprot ID
- P9WNW7
- Uniprot Name
- Iron-dependent extradiol dioxygenase
- Molecular Weight
- 33581.985 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 21:32 / Updated at June 12, 2020 16:52