(1S)-1,2,3,4-TETRAHYDRO-BENZO[C]PHENANTHRENE-2,3,4-TRIOL

Identification

Name
(1S)-1,2,3,4-TETRAHYDRO-BENZO[C]PHENANTHRENE-2,3,4-TRIOL
Accession Number
DB07479
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: 280.3178
Monoisotopic: 280.109944378
Chemical Formula
C18H16O3
InChI Key
WCUHTHVUZQCBTI-KBAYOESNSA-N
InChI
InChI=1S/C18H16O3/c19-15-9-14-13(17(20)18(15)21)8-7-11-6-5-10-3-1-2-4-12(10)16(11)14/h1-8,15,17-21H,9H2/t15-,17-,18-/m1/s1
IUPAC Name
(4R,5R,6R)-tetracyclo[8.8.0.0²,⁷.0¹³,¹⁸]octadeca-1(10),2(7),8,11,13(18),14,16-heptaene-4,5,6-triol
SMILES
[H][[email protected]@]1(O)CC2=C(C=CC3=C2C2=C(C=CC=C2)C=C3)[[email protected]@]([H])(O)[[email protected]]1([H])O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDNA polymerase betaNot 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
5287834
PubChem Substance
99443950
ChemSpider
4450129
HET
BPI
PDB Entries
1hwv / 2i9g

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 Solubility0.0674 mg/mLALOGPS
logP1.95ALOGPS
logP2.02ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)12.88ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area60.69 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity80.68 m3·mol-1ChemAxon
Polarizability30.35 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9852
Blood Brain Barrier-0.5293
Caco-2 permeable-0.6268
P-glycoprotein substrateSubstrate0.5474
P-glycoprotein inhibitor INon-inhibitor0.8684
P-glycoprotein inhibitor IINon-inhibitor0.9925
Renal organic cation transporterNon-inhibitor0.9188
CYP450 2C9 substrateNon-substrate0.7949
CYP450 2D6 substrateNon-substrate0.8858
CYP450 3A4 substrateNon-substrate0.6252
CYP450 1A2 substrateNon-inhibitor0.5252
CYP450 2C9 inhibitorNon-inhibitor0.835
CYP450 2D6 inhibitorNon-inhibitor0.8486
CYP450 2C19 inhibitorNon-inhibitor0.7953
CYP450 3A4 inhibitorNon-inhibitor0.9243
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8621
Ames testAMES toxic0.8455
CarcinogenicityNon-carcinogens0.9393
BiodegradationNot ready biodegradable0.866
Rat acute toxicity2.0161 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9737
hERG inhibition (predictor II)Non-inhibitor0.7445
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 phenanthrols. These are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenanthrenes and derivatives
Sub Class
Phenanthrols
Direct Parent
Phenanthrols
Alternative Parents
Tetralins / Naphthalenes / Secondary alcohols / Polyols / Hydrocarbon derivatives
Substituents
Phenanthrol / Tetralin / Naphthalene / Secondary alcohol / Polyol / Organic oxygen compound / Hydrocarbon derivative / Organooxygen compound / Alcohol / Aromatic homopolycyclic compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Microtubule binding
Specific Function
Repair polymerase that plays a key role in base-excision repair. Has 5'-deoxyribose-5-phosphate lyase (dRP lyase) activity that removes the 5' sugar phosphate and also acts as a DNA polymerase that...
Gene Name
POLB
Uniprot ID
P06746
Uniprot Name
DNA polymerase beta
Molecular Weight
38177.34 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 15:22 / Updated on December 01, 2017 15:51