Motuporin

Identification

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Name
Motuporin
Accession Number
DB04738
Type
Small Molecule
Groups
Experimental
Description

Motuporin is a toxin isolated from the marine sponge Thenonella swinhoie grey.

Structure
Thumb
Synonyms
  • (-)-Motuporin
  • Nodularin V
Categories
UNII
Not Available
CAS number
141672-08-4
Weight
Average: 767.921
Monoisotopic: 767.410543055
Chemical Formula
C40H57N5O10
InChI Key
GIRIHYQVGVTBIP-NJYUBDSESA-N
InChI
InChI=1S/C40H57N5O10/c1-10-30-37(49)44-34(40(53)54)26(7)36(48)43-33(22(2)3)38(50)41-28(25(6)35(47)42-29(39(51)52)18-19-32(46)45(30)8)17-16-23(4)20-24(5)31(55-9)21-27-14-12-11-13-15-27/h10-17,20,22,24-26,28-29,31,33-34H,18-19,21H2,1-9H3,(H,41,50)(H,42,47)(H,43,48)(H,44,49)(H,51,52)(H,53,54)/b17-16+,23-20+,30-10-/t24-,25-,26-,28-,29+,31-,33-,34+/m0/s1
IUPAC Name
(2Z,5R,6S,9S,12S,13S,16R)-2-ethylidene-12-[(1E,3E,5S,6S)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,6,13-trimethyl-3,7,10,14,19-pentaoxo-9-(propan-2-yl)-1,4,8,11,15-pentaazacyclononadecane-5,16-dicarboxylic acid
SMILES
[H]N1[C@H](CCC(=O)N(C)\C(=C/C)C(=O)N([H])[C@H]([C@H](C)C(=O)N([H])[C@@H](C(C)C)C(=O)N([H])[C@@H](\C=C\C(\C)=C\[C@H](C)[C@H](CC2=CC=CC=C2)OC)[C@H](C)C1=O)C(O)=O)C(O)=O

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
4369034
PubChem Substance
46508386
ChemSpider
3571791
BindingDB
50212842
ChEMBL
CHEMBL430145

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 Solubility0.00543 mg/mLALOGPS
logP2.32ALOGPS
logP2.57ChemAxon
logS-5.2ALOGPS
pKa (Strongest Acidic)3.43ChemAxon
pKa (Strongest Basic)-0.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area220.54 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity206.55 m3·mol-1ChemAxon
Polarizability81.15 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6637
Blood Brain Barrier-0.993
Caco-2 permeable-0.7568
P-glycoprotein substrateSubstrate0.8016
P-glycoprotein inhibitor IInhibitor0.7773
P-glycoprotein inhibitor IIInhibitor0.6649
Renal organic cation transporterNon-inhibitor0.9443
CYP450 2C9 substrateNon-substrate0.8144
CYP450 2D6 substrateNon-substrate0.8583
CYP450 3A4 substrateSubstrate0.6145
CYP450 1A2 substrateNon-inhibitor0.9169
CYP450 2C9 inhibitorNon-inhibitor0.8211
CYP450 2D6 inhibitorNon-inhibitor0.9045
CYP450 2C19 inhibitorNon-inhibitor0.8139
CYP450 3A4 inhibitorInhibitor0.6197
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9309
Ames testNon AMES toxic0.8932
CarcinogenicityNon-carcinogens0.9278
BiodegradationNot ready biodegradable0.9447
Rat acute toxicity2.9838 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9848
hERG inhibition (predictor II)Non-inhibitor0.688
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 oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Gamma-glutamyl peptides / Macrolactams / Beta amino acids and derivatives / Alpha amino acids and derivatives / Benzene and substituted derivatives / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Lactams / Azacyclic compounds
show 6 more
Substituents
Alpha-oligopeptide / Gamma-glutamyl alpha peptide / Macrolactam / Beta amino acid or derivatives / Alpha-amino acid or derivatives / Monocyclic benzene moiety / Dicarboxylic acid or derivatives / Benzenoid / Tertiary carboxylic acid amide / Carboxamide group
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

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. Maynes JT, Luu HA, Cherney MM, Andersen RJ, Williams D, Holmes CF, James MN: Crystal structures of protein phosphatase-1 bound to motuporin and dihydromicrocystin-LA: elucidation of the mechanism of enzyme inhibition by cyanobacterial toxins. J Mol Biol. 2006 Feb 10;356(1):111-20. Epub 2005 Nov 22. [PubMed:16343532]

Drug created on September 11, 2007 11:49 / Updated on June 04, 2019 06:10