NAV

N-[(2S,3S)-4-[2-[(5S)-3a,4,5,6,7,7a-Hexahydro-1,3-benzodioxol-5-yl]ethyl-[3-(1,3-dioxoisoindol-2-yl)propanoyl]amino]-3-hydroxy-1-phenylbutan-2-yl]-3,5-dimethoxy-4-phenylmethoxybenzamide

Identification

Generic Name
N-[(2S,3S)-4-[2-[(5S)-3a,4,5,6,7,7a-Hexahydro-1,3-benzodioxol-5-yl]ethyl-[3-(1,3-dioxoisoindol-2-yl)propanoyl]amino]-3-hydroxy-1-phenylbutan-2-yl]-3,5-dimethoxy-4-phenylmethoxybenzamide
DrugBank Accession Number
DB03063
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 805.9112
Monoisotopic: 805.357444867
Chemical Formula
C46H51N3O10
Synonyms
Not Available
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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
UPlasmepsin-2Not AvailablePlasmodium falciparum
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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
PJQGNNQTZMYXOB-HAMMGQCISA-N
InChI
InChI=1S/C46H51N3O10/c1-55-40-25-33(26-41(56-2)43(40)57-28-32-13-7-4-8-14-32)44(52)47-36(23-30-11-5-3-6-12-30)37(50)27-48(21-19-31-17-18-38-39(24-31)59-29-58-38)42(51)20-22-49-45(53)34-15-9-10-16-35(34)46(49)54/h3-16,25-26,31,36-39,50H,17-24,27-29H2,1-2H3,(H,47,52)/t31-,36-,37-,38?,39?/m0/s1
IUPAC Name
N-[(2S,3S)-3-{[4-(benzyloxy)-3,5-dimethoxyphenyl]formamido}-2-hydroxy-4-phenylbutyl]-3-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-N-{2-[(5S)-hexahydro-2H-1,3-benzodioxol-5-yl]ethyl}propanamide
SMILES
COC1=CC(=CC(OC)=C1OCC1=CC=CC=C1)C(=O)N[C@@H](CC1=CC=CC=C1)[C@@H](O)CN(CC[C@@H]1CCC2OCOC2C1)C(=O)CCN1C(=O)C2=CC=CC=C2C1=O

References

General References
Not Available
PubChem Compound
131704228
PubChem Substance
46505048
ChemSpider
64873364
PDBe Ligand
EH5
PDB Entries
1lf3

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 Solubility0.000988 mg/mLALOGPS
logP4.85ALOGPS
logP5.09Chemaxon
logS-5.9ALOGPS
pKa (Strongest Acidic)13.98Chemaxon
pKa (Strongest Basic)-0.74Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area153.17 Å2Chemaxon
Rotatable Bond Count18Chemaxon
Refractivity219.47 m3·mol-1Chemaxon
Polarizability87.18 Å3Chemaxon
Number of Rings7Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.6371
Blood Brain Barrier-0.9048
Caco-2 permeable-0.7272
P-glycoprotein substrateSubstrate0.827
P-glycoprotein inhibitor INon-inhibitor0.6707
P-glycoprotein inhibitor IINon-inhibitor0.6852
Renal organic cation transporterNon-inhibitor0.7938
CYP450 2C9 substrateNon-substrate0.8514
CYP450 2D6 substrateNon-substrate0.8045
CYP450 3A4 substrateSubstrate0.6993
CYP450 1A2 substrateNon-inhibitor0.8737
CYP450 2C9 inhibitorNon-inhibitor0.8451
CYP450 2D6 inhibitorNon-inhibitor0.7624
CYP450 2C19 inhibitorNon-inhibitor0.7084
CYP450 3A4 inhibitorInhibitor0.8493
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8289
Ames testNon AMES toxic0.732
CarcinogenicityNon-carcinogens0.9249
BiodegradationNot ready biodegradable0.8848
Rat acute toxicity2.3166 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.939
hERG inhibition (predictor II)Inhibitor0.6941
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/MSsplash10-0a4u-3458152390-b7d471e693ff9bdc84ca
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ue9-0101093350-8b2da3753be64ac9167a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-3102320940-59210444ccd14b434e11
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uyj-0214183930-c3c1fcd0b5f06bfeaa57
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ar3-4901021520-a7a1d766825d76aa6ac6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ow-4802292620-bba2147167f1cd9f59ff
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-253.46275
predicted
DeepCCS 1.0 (2019)
[M+H]+255.35817
predicted
DeepCCS 1.0 (2019)
[M+Na]+261.42053
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Plasmepsin-2
Kind
Protein
Organism
Plasmodium falciparum
Pharmacological action
Unknown
General Function
Aspartic-type endopeptidase activity
Specific Function
Not Available
Gene Name
Not Available
Uniprot ID
P46925
Uniprot Name
Plasmepsin-2
Molecular Weight
51489.41 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