Calyculin A

Identification

Name
Calyculin A
Accession Number
DB02860  (EXPT01080)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (-)-calyculin A
Categories
UNII
7D07U14TK3
CAS number
101932-71-2
Weight
Average: 1009.185
Monoisotopic: 1008.543604922
Chemical Formula
C50H81N4O15P
InChI Key
FKAWLXNLHHIHLA-YCBIHMBMSA-N
InChI
InChI=1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45+,46-,50+/m0/s1
IUPAC Name
{[(2R,3R,5R,7S,8S,9R)-2-[(1S,3S,4S,5R,6R,7E,9E,11E,13Z)-14-cyano-3,5-dihydroxy-1-methoxy-4,6,8,9,13-pentamethyltetradeca-7,9,11,13-tetraen-1-yl]-7-[(2E)-3-{2-[(2S)-4-[(2S,3S,4S)-4-(dimethylamino)-2,3-dihydroxy-5-methoxypentanamido]butan-2-yl]-1,3-oxazol-4-yl}prop-2-en-1-yl]-9-hydroxy-4,4,8-trimethyl-1,6-dioxaspiro[4.5]decan-3-yl]oxy}phosphonic acid
SMILES

Pharmacology

Indication
Not Available
Structured Indications
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
C05370
PubChem Compound
5311365
PubChem Substance
46506773
ChemSpider
4470862
BindingDB
50110681
ChEMBL
CHEMBL430266
HET
CYU

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 Solubility0.249 mg/mLALOGPS
logP3.65ALOGPS
logP1.77ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)1.15ChemAxon
pKa (Strongest Basic)8.22ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area286.99 Å2ChemAxon
Rotatable Bond Count26ChemAxon
Refractivity267.1 m3·mol-1ChemAxon
Polarizability107.46 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9434
Blood Brain Barrier-0.9771
Caco-2 permeable-0.6726
P-glycoprotein substrateSubstrate0.8079
P-glycoprotein inhibitor IInhibitor0.66
P-glycoprotein inhibitor IINon-inhibitor0.9619
Renal organic cation transporterNon-inhibitor0.9254
CYP450 2C9 substrateNon-substrate0.8241
CYP450 2D6 substrateNon-substrate0.8143
CYP450 3A4 substrateSubstrate0.6457
CYP450 1A2 substrateNon-inhibitor0.7723
CYP450 2C9 inhibitorNon-inhibitor0.8017
CYP450 2D6 inhibitorNon-inhibitor0.887
CYP450 2C19 inhibitorNon-inhibitor0.7683
CYP450 3A4 inhibitorNon-inhibitor0.897
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9696
Ames testNon AMES toxic0.5987
CarcinogenicityNon-carcinogens0.9067
BiodegradationNot ready biodegradable0.8264
Rat acute toxicity2.7759 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8202
hERG inhibition (predictor II)Non-inhibitor0.74
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 aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Prenol lipids
Sub Class
Monoterpenoids
Direct Parent
Aromatic monoterpenoids
Alternative Parents
Pentoses / 2,4-disubstituted oxazoles / Ketals / Monoalkyl phosphates / N-acyl amines / Oxanes / Tetrahydrofurans / Heteroaromatic compounds / 1,3-aminoalcohols / 1,2-aminoalcohols
show 12 more
Substituents
Pentose monosaccharide / Aromatic monoterpenoid / 2,4-disubstituted 1,3-oxazole / Ketal / Monoalkyl phosphate / Phosphoric acid ester / Oxane / Alkyl phosphate / Organic phosphoric acid derivative / Fatty acyl
show 35 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monoterpenoid (CHEBI:41791)

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]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:20