Identification
Name9,10-Deepithio-9,10-Didehydroacanthifolicin
Accession NumberDB02169  (EXPT02429)
TypeSmall Molecule
GroupsExperimental
Description

A specific inhibitor of phosphoserine/threonine protein phosphatase 1 and 2a. It is also a potent tumor promoter. (Thromb Res 1992;67(4):345-54 & Cancer Res 1993;53(2):239-41)

Structure
Thumb
SynonymsNot Available
External IDs NSC-677083
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
CategoriesNot Available
UNII1W21G5Q4N2
CAS number78111-17-8
WeightAverage: 805.0029
Monoisotopic: 804.465992262
Chemical FormulaC44H68O13
InChI KeyQNDVLZJODHBUFM-WFXQOWMNSA-N
InChI
InChI=1S/C44H68O13/c1-25-21-34(55-44(23-25)35(46)12-11-31(54-44)24-41(6,50)40(48)49)26(2)9-10-30-14-18-43(53-30)19-15-33-39(57-43)36(47)29(5)38(52-33)32(45)22-28(4)37-27(3)13-17-42(56-37)16-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2,1-4,6H3,(H,48,49)/b10-9+/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37+,38+,39-,41-,42+,43-,44-/m1/s1
IUPAC Name
(2R)-3-[(2S,5R,6R,8S)-8-[(2R,3E)-4-[(2R,4'aR,5R,6'S,8'R,8'aS)-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2S,3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-7'-methylidene-hexahydro-3'H-spiro[oxolane-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl]-5-hydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-hydroxy-2-methylpropanoic acid
SMILES
[H]\C(=C(\[H])[C@@]1([H])CC[C@@]2(CC[C@@]3([H])O[C@@]([H])(C(=C)[C@@]([H])(O)[C@]3([H])O2)[C@@]([H])(O)C[C@]([H])(C)[C@@]2([H])O[C@@]3(CCCCO3)CC[C@@]2([H])C)O1)[C@@]([H])(C)[C@]1([H])CC(C)=C[C@@]2(O[C@]([H])(C[C@@](C)(O)C(O)=O)CC[C@@]2([H])O)O1
Pharmacology
IndicationNot Available
Structured Indications Not Available
PharmacodynamicsNot Available
Mechanism of action
TargetKindPharmacological actionActionsOrganismUniProt ID
Serine/threonine-protein phosphatase PP1-gamma catalytic subunitProteinunknownNot AvailableHumanP36873 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00442 mg/mLALOGPS
logP2.73ALOGPS
logP5.13ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)3.76ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area182.83 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity210.78 m3·mol-1ChemAxon
Polarizability88.64 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.774
Blood Brain Barrier+0.7501
Caco-2 permeable-0.7499
P-glycoprotein substrateSubstrate0.8476
P-glycoprotein inhibitor INon-inhibitor0.5804
P-glycoprotein inhibitor IINon-inhibitor0.8289
Renal organic cation transporterNon-inhibitor0.8043
CYP450 2C9 substrateNon-substrate0.8816
CYP450 2D6 substrateNon-substrate0.893
CYP450 3A4 substrateSubstrate0.7343
CYP450 1A2 substrateNon-inhibitor0.8688
CYP450 2C9 inhibitorNon-inhibitor0.902
CYP450 2D6 inhibitorNon-inhibitor0.9508
CYP450 2C19 inhibitorNon-inhibitor0.8976
CYP450 3A4 inhibitorNon-inhibitor0.816
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9621
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.971
BiodegradationNot ready biodegradable0.9771
Rat acute toxicity3.6260 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9472
hERG inhibition (predictor II)Non-inhibitor0.5103
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentKetals
Alternative ParentsPyrans / Oxanes / Alpha hydroxy acids and derivatives / Tertiary alcohols / Oxolanes / Secondary alcohols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Dialkyl ethers / Carboxylic acids
SubstituentsKetal / Alpha-hydroxy acid / Hydroxy acid / Oxane / Pyran / Oxolane / Tertiary alcohol / Secondary alcohol / Organoheterocyclic compound / Oxacycle
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptorspolycyclic ether (CHEBI:44658 )

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Protein serine/threonine phosphatase activity
Specific Function:
Protein phosphatase that associates with over 200 regulatory proteins to form highly specific holoenzymes which dephosphorylate hundreds of biological targets. Protein phosphatase 1 (PP1) is essential for cell division, and participates in the regulation of glycogen metabolism, muscle contractility and protein synthesis. Dephosphorylates RPS6KB1. Involved in regulation of ionic conductances and...
Gene Name:
PPP1CC
Uniprot ID:
P36873
Molecular Weight:
36983.4 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 July 18, 2017 17:06