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Identification
Name9,10-Deepithio-9,10-Didehydroacanthifolicin
Accession NumberDB02169  (EXPT02429)
TypeSmall Molecule
GroupsExperimental
DescriptionA 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 Identifiers 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
SaltsNot Available
CategoriesNot Available
UNII1W21G5Q4N2
CAS number78111-17-8
WeightAverage: 805.0029
Monoisotopic: 804.465992262
Chemical FormulaC44H68O13
InChI KeyInChIKey=QNDVLZJODHBUFM-NHKYITFXSA-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-[(2R,5S,6S,8R)-8-[(2R,3E)-4-[(2S,4'aR,5S,6'R,8'S,8'aR)-8'-hydroxy-6'-[(1S,3S)-1-hydroxy-3-[(2R,3R,6R)-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
C[C@@H](C[[email protected]](O)[C@@H]1O[C@@H]2CC[C@]3(CC[[email protected]](O3)\C=C\[C@@H](C)[[email protected]]3CC(C)=C[C@]4(O[C@@H](C[C@@](C)(O)C(O)=O)CC[C@@H]4O)O3)O[C@@H]2[C@@H](O)C1=C)[C@@H]1O[C@]2(CCCCO2)CC[[email protected]]1C
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassAlpha hydroxy acids and derivatives
Direct ParentAlpha hydroxy acids and derivatives
Alternative Parents
Substituents
  • Pyran
  • Oxane
  • Alpha-hydroxy acid
  • Tertiary alcohol
  • Oxolane
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Acetal
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Polarizability88.85 Å3ChemAxon
Number of Rings7ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23