4-[(10s,14s,18s)-18-(2-Amino-2-Oxoethyl)-14-(1-Naphthylmethyl)-8,17,20-Trioxo-7,16,19-Triazaspiro[5.14]Icos-11-En-10-Yl]Benzylphosphonic Acid

Identification

Name
4-[(10s,14s,18s)-18-(2-Amino-2-Oxoethyl)-14-(1-Naphthylmethyl)-8,17,20-Trioxo-7,16,19-Triazaspiro[5.14]Icos-11-En-10-Yl]Benzylphosphonic Acid
Accession Number
DB03276  (EXPT01283)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 688.7496
Monoisotopic: 688.302586326
Chemical Formula
C37H45N4O7P
InChI Key
RHYFMOCFCFUTNH-GZNVFMSSSA-N
InChI
InChI=1S/C37H45N4O7P/c38-33(42)22-32-35(44)39-23-26(20-30-12-7-10-28-9-2-3-13-31(28)30)8-6-11-29(27-16-14-25(15-17-27)24-49(46,47)48)21-34(43)41-37(36(45)40-32)18-4-1-5-19-37/h2-3,6-7,9-17,26,29,32H,1,4-5,8,18-24H2,(H2,38,42)(H,39,44)(H,40,45)(H,41,43)(H2,46,47,48)/b11-6+/t26-,29-,32-/m0/s1
IUPAC Name
({4-[(10R,11E,14S,18S)-18-(carbamoylmethyl)-14-(naphthalen-1-ylmethyl)-8,17,20-trioxo-7,16,19-triazaspiro[5.14]icos-11-en-10-yl]phenyl}methyl)phosphonic acid
SMILES
NC(=O)C[[email protected]@H]1NC(=O)C2(CCCCC2)NC(=O)C[[email protected]](\C=C\C[[email protected]](CNC1=O)CC1=CC=CC2=CC=CC=C12)C1=CC=C(C=C1)CP(O)(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGrowth factor receptor-bound protein 2Not 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
PubChem Compound
657098
PubChem Substance
46506983
ChemSpider
571301
BindingDB
50102025
ChEMBL
CHEMBL291678
HET
DTF
PDB Entries
1x0n

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 Solubility0.000825 mg/mLALOGPS
logP2.54ALOGPS
logP2.58ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)-0.21ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area187.92 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity186.91 m3·mol-1ChemAxon
Polarizability71.18 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.5153
Blood Brain Barrier+0.5125
Caco-2 permeable-0.7111
P-glycoprotein substrateSubstrate0.8101
P-glycoprotein inhibitor INon-inhibitor0.7171
P-glycoprotein inhibitor IINon-inhibitor0.9847
Renal organic cation transporterNon-inhibitor0.9025
CYP450 2C9 substrateNon-substrate0.7725
CYP450 2D6 substrateNon-substrate0.7741
CYP450 3A4 substrateNon-substrate0.5326
CYP450 1A2 substrateNon-inhibitor0.8358
CYP450 2C9 inhibitorNon-inhibitor0.7779
CYP450 2D6 inhibitorNon-inhibitor0.8681
CYP450 2C19 inhibitorNon-inhibitor0.7619
CYP450 3A4 inhibitorNon-inhibitor0.717
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9298
Ames testNon AMES toxic0.5931
CarcinogenicityNon-carcinogens0.8296
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5698 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9012
hERG inhibition (predictor II)Inhibitor0.5119
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 cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Cyclic peptides
Alternative Parents
Dipeptides / Naphthalenes / Alpha amino acids and derivatives / Benzene and substituted derivatives / Organic phosphonic acids / Secondary carboxylic acid amides / Primary carboxylic acid amides / Lactams / Azacyclic compounds / Organopnictogen compounds
show 5 more
Substituents
Alpha-dipeptide / Cyclic alpha peptide / Alpha-amino acid or derivatives / Naphthalene / Monocyclic benzene moiety / Benzenoid / Organophosphonic acid / Organophosphonic acid derivative / Carboxamide group / Lactam
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Sh3/sh2 adaptor activity
Specific Function
Adapter protein that provides a critical link between cell surface growth factor receptors and the Ras signaling pathway.Isoform 2 does not bind to phosphorylated epidermal growth factor receptor (...
Gene Name
GRB2
Uniprot ID
P62993
Uniprot Name
Growth factor receptor-bound protein 2
Molecular Weight
25206.21 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]
  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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on December 01, 2017 15:10