9,10-Deepithio-9,10-Didehydroacanthifolicin
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Identification
- Generic Name
- 9,10-Deepithio-9,10-Didehydroacanthifolicin
- DrugBank Accession Number
- DB02169
- Background
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)
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 805.0029
Monoisotopic: 804.465992262 - Chemical Formula
- C44H68O13
- Synonyms
- Not Available
- External IDs
- NSC-677083
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism USerine/threonine-protein phosphatase PP1-gamma catalytic subunit Not Available Humans - 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
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
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
Categories
- Drug Categories
- Not Available
- Chemical TaxonomyProvided by Classyfire
- 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
- Alcohol / Aliphatic heteropolycyclic compound / Alpha-hydroxy acid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Dialkyl ether / Hydrocarbon derivative / Hydroxy acid / Ketal show 9 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- polycyclic ether (CHEBI:44658)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 1W21G5Q4N2
- CAS number
- 78111-17-8
- 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
References
- General References
- Not Available
- External Links
- KEGG Compound
- C01945
- PubChem Compound
- 446512
- PubChem Substance
- 46504468
- ChemSpider
- 393845
- BindingDB
- 50110676
- ChEBI
- 44658
- ChEMBL
- CHEMBL280487
- ZINC
- ZINC000085601542
- PDBe Ligand
- OKA
- PDB Entries
- 1jk7 / 1u32 / 2ie4 / 4wri
Clinical Trials
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
Property Value Source Water Solubility 0.00442 mg/mL ALOGPS logP 2.73 ALOGPS logP 5.13 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 3.76 Chemaxon pKa (Strongest Basic) -3.2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 13 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 182.83 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 210.78 m3·mol-1 Chemaxon Polarizability 88.64 Å3 Chemaxon Number of Rings 7 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.774 Blood Brain Barrier + 0.7501 Caco-2 permeable - 0.7499 P-glycoprotein substrate Substrate 0.8476 P-glycoprotein inhibitor I Non-inhibitor 0.5804 P-glycoprotein inhibitor II Non-inhibitor 0.8289 Renal organic cation transporter Non-inhibitor 0.8043 CYP450 2C9 substrate Non-substrate 0.8816 CYP450 2D6 substrate Non-substrate 0.893 CYP450 3A4 substrate Substrate 0.7343 CYP450 1A2 substrate Non-inhibitor 0.8688 CYP450 2C9 inhibitor Non-inhibitor 0.902 CYP450 2D6 inhibitor Non-inhibitor 0.9508 CYP450 2C19 inhibitor Non-inhibitor 0.8976 CYP450 3A4 inhibitor Non-inhibitor 0.816 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9621 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.971 Biodegradation Not ready biodegradable 0.9771 Rat acute toxicity 3.6260 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9472 hERG inhibition (predictor II) Non-inhibitor 0.5103
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 334.9128349 predictedDarkChem Lite v0.1.0 [M-H]- 239.14482 predictedDeepCCS 1.0 (2019) [M+H]+ 240.86855 predictedDeepCCS 1.0 (2019) [M+Na]+ 247.1975 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- 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. [Article]
- 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. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52