(9S,10S)-9-(S-glutathionyl)-10-hydroxy-9,10-dihydrophenanthrene

Identification

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Name
(9S,10S)-9-(S-glutathionyl)-10-hydroxy-9,10-dihydrophenanthrene
Accession Number
DB04187  (EXPT01642)
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: 501.552
Monoisotopic: 501.156970923
Chemical Formula
C24H27N3O7S
InChI Key
JNNIZILNBMPOAC-GPHNJDIKSA-N
InChI
InChI=1S/C24H27N3O7S/c25-17(24(33)34)9-10-19(28)27-18(23(32)26-11-20(29)30)12-35-22-16-8-4-2-6-14(16)13-5-1-3-7-15(13)21(22)31/h1-8,17-18,21-22,31H,9-12,25H2,(H,26,32)(H,27,28)(H,29,30)(H,33,34)/t17-,18-,21-,22-/m0/s1
IUPAC Name
(2S)-2-amino-4-{[(1R)-1-[(carboxymethyl)carbamoyl]-2-{[(9S,10S)-10-hydroxy-9,10-dihydrophenanthren-9-yl]sulfanyl}ethyl]carbamoyl}butanoic acid
SMILES
[H]N([H])[C@@H](CCC(=O)N([H])[C@@H](CS[C@]1([H])[C@@H](O)C2=CC=CC=C2C2=CC=CC=C12)C(=O)N([H])CC(O)=O)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGlutathione S-transferase Mu 1Not AvailableHumans
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
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

References

General References
Not Available
External Links
PubChem Compound
444461
PubChem Substance
46506704
ChemSpider
392389
ZINC
ZINC000012501153
HET
GPS
PDB Entries
1b4p / 2gst / 6gsu / 6gsv / 6gsw / 6gsx

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 Solubility0.031 mg/mLALOGPS
logP-1.3ALOGPS
logP-2.2ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)1.8ChemAxon
pKa (Strongest Basic)9.31ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area179.05 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity127.88 m3·mol-1ChemAxon
Polarizability50.09 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5581
Blood Brain Barrier-0.7238
Caco-2 permeable-0.7699
P-glycoprotein substrateSubstrate0.6612
P-glycoprotein inhibitor INon-inhibitor0.8874
P-glycoprotein inhibitor IINon-inhibitor0.9713
Renal organic cation transporterNon-inhibitor0.8288
CYP450 2C9 substrateNon-substrate0.8189
CYP450 2D6 substrateNon-substrate0.7762
CYP450 3A4 substrateNon-substrate0.5905
CYP450 1A2 substrateNon-inhibitor0.7181
CYP450 2C9 inhibitorNon-inhibitor0.861
CYP450 2D6 inhibitorNon-inhibitor0.8462
CYP450 2C19 inhibitorNon-inhibitor0.6701
CYP450 3A4 inhibitorNon-inhibitor0.5654
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8486
Ames testNon AMES toxic0.6452
CarcinogenicityNon-carcinogens0.9264
BiodegradationNot ready biodegradable0.9321
Rat acute toxicity2.2178 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9867
hERG inhibition (predictor II)Non-inhibitor0.5416
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 oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Gamma-glutamyl peptides / Glutamine and derivatives / Hydrophenanthrenes / N-acyl-alpha amino acids / Alpha amino acid amides / Cysteine and derivatives / L-alpha-amino acids / Naphthalenes / Dicarboxylic acids and derivatives / N-acyl amines
show 11 more
Substituents
Alpha-oligopeptide / Gamma-glutamyl alpha peptide / Glutamine or derivatives / Hydrophenanthrene / Phenanthrene / N-acyl-alpha amino acid or derivatives / N-acyl-alpha-amino acid / Cysteine or derivatives / Alpha-amino acid amide / N-substituted-alpha-amino acid
show 32 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Protein homodimerization activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTM1
Uniprot ID
P09488
Uniprot Name
Glutathione S-transferase Mu 1
Molecular Weight
25711.555 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. 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 June 13, 2005 07:24 / Updated on February 06, 2020 11:55