9,10-Deepithio-9,10-Didehydroacanthifolicin

Identification

Name
9,10-Deepithio-9,10-Didehydroacanthifolicin
Accession Number
DB02169  (EXPT02429)
Type
Small Molecule
Groups
Experimental
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
Synonyms
Not Available
External IDs
NSC-677083
Categories
Not Available
UNII
1W21G5Q4N2
CAS number
78111-17-8
Weight
Average: 805.0029
Monoisotopic: 804.465992262
Chemical Formula
C44H68O13
InChI Key
QNDVLZJODHBUFM-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

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
USerine/threonine-protein phosphatase PP1-gamma catalytic subunitNot 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
KEGG Compound
C01945
PubChem Compound
446512
PubChem Substance
46504468
ChemSpider
393845
BindingDB
50110676
ChEBI
44658
ChEMBL
CHEMBL280487
HET
OKA
PDB Entries
1jk7 / 1u32 / 2ie4 / 4wri

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 Solubility0.00442 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
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 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.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Ethers
Direct Parent
Ketals
Alternative Parents
Pyrans / Oxanes / Alpha hydroxy acids and derivatives / Tetrahydrofurans / Tertiary alcohols / Secondary alcohols / Oxacyclic compounds / Monocarboxylic acids and derivatives / Dialkyl ethers / Carboxylic acids
show 3 more
Substituents
Ketal / Alpha-hydroxy acid / Hydroxy acid / Oxane / Pyran / Tertiary alcohol / Tetrahydrofuran / Secondary alcohol / Organoheterocyclic compound / Oxacycle
show 9 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
polycyclic 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 essent...
Gene Name
PPP1CC
Uniprot ID
P36873
Uniprot Name
Serine/threonine-protein phosphatase PP1-gamma catalytic subunit
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 November 02, 2018 05:13