3,4-dihydroxy-9,10-secoandrosta-1(10),2,4-triene-9,17-dione

Identification

Name
3,4-dihydroxy-9,10-secoandrosta-1(10),2,4-triene-9,17-dione
Accession Number
DB08542
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: 316.3915
Monoisotopic: 316.167459256
Chemical Formula
C19H24O4
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UIron-dependent extradiol dioxygenaseNot AvailableMycobacterium 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
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
KEGG Compound
C04793
PubChem Compound
440483
PubChem Substance
99445013
ChemSpider
389410
ChEBI
15896
HET
SDT
PDB Entries
2zi8

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 Solubility0.0306 mg/mLALOGPS
logP3.17ALOGPS
logP4.15ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.44ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity88.19 m3·mol-1ChemAxon
Polarizability34.68 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.962
Blood Brain Barrier+0.7847
Caco-2 permeable+0.5804
P-glycoprotein substrateSubstrate0.7897
P-glycoprotein inhibitor INon-inhibitor0.9333
P-glycoprotein inhibitor IINon-inhibitor0.7947
Renal organic cation transporterNon-inhibitor0.8566
CYP450 2C9 substrateNon-substrate0.7855
CYP450 2D6 substrateNon-substrate0.8582
CYP450 3A4 substrateSubstrate0.7282
CYP450 1A2 substrateInhibitor0.5084
CYP450 2C9 inhibitorNon-inhibitor0.9293
CYP450 2D6 inhibitorNon-inhibitor0.9454
CYP450 2C19 inhibitorNon-inhibitor0.8942
CYP450 3A4 inhibitorNon-inhibitor0.8099
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9218
Ames testNon AMES toxic0.8248
CarcinogenicityNon-carcinogens0.9284
BiodegradationNot ready biodegradable0.9908
Rat acute toxicity2.0618 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9516
hERG inhibition (predictor II)Inhibitor0.6414
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 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 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
P-cresol / M-cresol / Catechol / 1-hydroxy-4-unsubstituted benzenoid / 1-hydroxy-2-unsubstituted benzenoid / Toluene / Monocyclic benzene moiety / Cyclic ketone / Ketone / Organic oxygen compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
seco-androstane (CHEBI:15896) / C19 steroids (androgens) and derivatives (C04793) / C19 steroids (androgens) and derivatives (LMST02020062)

Targets

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
  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