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Identification
NameCalyculin A
Accession NumberDB02860  (EXPT01080)
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
Synonyms
(-)-calyculin A
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
Categories
UNII7D07U14TK3
CAS number101932-71-2
WeightAverage: 1009.185
Monoisotopic: 1008.543604922
Chemical FormulaC50H81N4O15P
InChI KeyFKAWLXNLHHIHLA-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
[H][C@@]1(O[C@]2(C[C@@H](O)[[email protected]](C)[[email protected]](C\C=C\C3=COC(=N3)[C@@H](C)CCNC(=O)[C@@H](O)[C@@H](O)[[email protected]](COC)N(C)C)O2)C(C)(C)[[email protected]]1OP(O)(O)=O)[[email protected]](C[[email protected]](O)[[email protected]](C)[[email protected]](O)[[email protected]](C)\C=C(/C)\C(\C)=C\C=C\C(\C)=C/C#N)OC
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
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
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • 1,3-aminoalcohol
  • Oxolane
  • Azole
  • Heteroaromatic compound
  • Oxazole
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxamide group
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Nitrile
  • Carbonitrile
  • Azacycle
  • Oxacycle
  • Acetal
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic nitrogen compound
  • Carbonyl group
  • Organic oxide
  • Cyanide
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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-0.9434
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 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 ]
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Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23