NAV

9,10-Deepithio-9,10-Didehydroacanthifolicin

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
Similar Structures
Weight
Average: 805.0029
Monoisotopic: 804.465992262
Chemical Formula
C44H68O13
Synonyms
Not Available
External IDs
  • NSC-677083
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USerine/threonine-protein phosphatase PP1-gamma catalytic subunitNot 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

Adverse Effects
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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
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

Clinical Trials
PhaseStatusPurposeConditionsCount

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/MSsplash10-000i-0010000920-7eafda82aea87f5fd5dc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0001100590-646f0d007977187c6f16
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0400013920-1ce83a2ba5f2c8e39df0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2020101790-871e05f609e140479a34
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4j-0607944220-599bd2af21615e82c78e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-1040013390-6426ee0d663d1708f908
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-334.9128349
predicted
DarkChem Lite v0.1.0
[M-H]-239.14482
predicted
DeepCCS 1.0 (2019)
[M+H]+240.86855
predicted
DeepCCS 1.0 (2019)
[M+Na]+247.1975
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Serine/threonine-protein phosphatase PP1-gamma catalytic subunit
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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52