NAV

Calyculin A

Identification

Generic Name
Calyculin A
DrugBank Accession Number
DB02860
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 1009.185
Monoisotopic: 1008.543604922
Chemical Formula
C50H81N4O15P
Synonyms
  • (-)-calyculin A
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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.
DrugInteraction
Integrate drug-drug
interactions in your software
ChloroprocaineThe risk or severity of adverse effects can be increased when Calyculin A is combined with Chloroprocaine.
LevothyroxineLevothyroxine may increase the vasoconstricting activities of Calyculin A.
LidocaineThe risk or severity of hypertension can be increased when Calyculin A is combined with Lidocaine.
LiothyronineLiothyronine may increase the vasoconstricting activities of Calyculin A.
LiotrixLiotrix may increase the vasoconstricting activities of Calyculin A.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
1,2-aminoalcohol / 1,3-aminoalcohol / 2,4-disubstituted 1,3-oxazole / Acetal / Alcohol / Alkyl phosphate / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Aromatic monoterpenoid
show 35 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monoterpenoid (CHEBI:41791)
Affected organisms
Not Available

Chemical Identifiers

UNII
7D07U14TK3
CAS number
101932-71-2
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
[H][C@@]1(O[C@]2(C[C@@H](O)[C@H](C)[C@H](C\C=C\C3=COC(=N3)[C@@H](C)CCNC(=O)[C@@H](O)[C@@H](O)[C@H](COC)N(C)C)O2)C(C)(C)[C@H]1OP(O)(O)=O)[C@H](C[C@H](O)[C@H](C)[C@H](O)[C@H](C)\C=C(/C)\C(\C)=C\C=C\C(\C)=C/C#N)OC

References

General References
Not Available
KEGG Compound
C05370
PubChem Compound
5311365
PubChem Substance
46506773
ChemSpider
4470862
BindingDB
50110681
ChEMBL
CHEMBL430266
PDBe Ligand
CYU
Wikipedia
Calyculin

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 Solubility0.249 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/MSsplash10-06u6-1220000029-036db6aab6b6a4707f69
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1100000009-f1b6e767dafe6675ec5c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1110000019-e4abcc07dfa2957a032d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-3300001193-4a2841f061f4b123015e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ap1-4940010022-b2b8ce6aa5901d06e881
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0159-3331000594-bda9151bbc949db9be61
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-307.68546
predicted
DeepCCS 1.0 (2019)
[M+H]+309.35333
predicted
DeepCCS 1.0 (2019)
[M+Na]+315.51016
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]

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