NAV

(20S)-19,20,21,22-TETRAHYDRO-19-OXO-5H-18,20-ETHANO-12,14-ETHENO-6,10-METHENO-18H-BENZ[D]IMIDAZO[4,3-K][1,6,9,12]OXATRIAZA-CYCLOOCTADECOSINE-9-CARBONITRILE

Identification

Generic Name
(20S)-19,20,21,22-TETRAHYDRO-19-OXO-5H-18,20-ETHANO-12,14-ETHENO-6,10-METHENO-18H-BENZ[D]IMIDAZO[4,3-K][1,6,9,12]OXATRIAZA-CYCLOOCTADECOSINE-9-CARBONITRILE
DrugBank Accession Number
DB08674
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 435.4772
Monoisotopic: 435.169524941
Chemical Formula
C26H21N5O2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UProtein farnesyltransferase/geranylgeranyltransferase type-1 subunit alphaNot AvailableHumans
UProtein farnesyltransferase subunit betaNot 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.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as macrolactams. These are cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. They are nitrogen analogues (the a nitrogen atom replacing the o atom of the cyclic carboxylic acid group ) of the naturally occurring macrolides.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Macrolactams
Sub Class
Not Available
Direct Parent
Macrolactams
Alternative Parents
Diarylethers / Alpha amino acids and derivatives / Naphthalenes / Aralkylamines / Pyrrolidine-2-ones / N-substituted imidazoles / Tertiary carboxylic acid amides / Heteroaromatic compounds / Lactams / Oxacyclic compounds
show 7 more
Substituents
2-pyrrolidone / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azole / Benzenoid / Carbonitrile
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
USPFJPDEADLGIG-HSZRJFAPSA-N
InChI
InChI=1S/C26H21N5O2/c27-12-19-5-4-17-10-25(19)33-21-7-6-18-2-1-3-24(22(18)11-21)31-9-8-23(26(31)32)29-14-20-13-28-16-30(20)15-17/h1-7,10-11,13,16,23,29H,8-9,14-15H2/t23-/m1/s1
IUPAC Name
(5R)-30-oxo-19-oxa-2,6,10,12-tetraazahexacyclo[18.6.2.1^{2,5}.1^{14,18}.0^{8,12}.0^{23,27}]triaconta-1(27),8,10,14(29),15,17,20(28),21,23,25-decaene-17-carbonitrile
SMILES
[H][C@@]12CCN(C1=O)C1=C3C=C(OC4=C(C=CC(CN5C=NC=C5CN2)=C4)C#N)C=CC3=CC=C1

References

General References
Not Available
PubChem Compound
23646577
PubChem Substance
99445145
BindingDB
14010
ChEMBL
CHEMBL496879
ZINC
ZINC000003870365
PDBe Ligand
U49
PDB Entries
1ld8

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 Solubility0.1 mg/mLALOGPS
logP2.51ALOGPS
logP2.53Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)17.65Chemaxon
pKa (Strongest Basic)6.56Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area83.18 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity124.12 m3·mol-1Chemaxon
Polarizability44.65 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9311
Caco-2 permeable+0.5309
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.6346
P-glycoprotein inhibitor IINon-inhibitor0.6548
Renal organic cation transporterInhibitor0.5088
CYP450 2C9 substrateNon-substrate0.8042
CYP450 2D6 substrateNon-substrate0.6477
CYP450 3A4 substrateSubstrate0.5629
CYP450 1A2 substrateInhibitor0.8519
CYP450 2C9 inhibitorInhibitor0.6086
CYP450 2D6 inhibitorNon-inhibitor0.5606
CYP450 2C19 inhibitorInhibitor0.6215
CYP450 3A4 inhibitorNon-inhibitor0.5833
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8457
Ames testAMES toxic0.589
CarcinogenicityNon-carcinogens0.9081
BiodegradationNot ready biodegradable0.9959
Rat acute toxicity2.5284 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8296
hERG inhibition (predictor II)Inhibitor0.5
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 GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Targets

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Details1. Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Rab geranylgeranyltransferase activity
Specific Function
Essential subunit of both the farnesyltransferase and the geranylgeranyltransferase complex. Contributes to the transfer of a farnesyl or geranylgeranyl moiety from farnesyl or geranylgeranyl dipho...
Gene Name
FNTA
Uniprot ID
P49354
Uniprot Name
Protein farnesyltransferase/geranylgeranyltransferase type-1 subunit alpha
Molecular Weight
44408.32 Da
References
  1. 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. [Article]
Details2. Protein farnesyltransferase subunit beta
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Essential subunit of the farnesyltransferase complex. Catalyzes the transfer of a farnesyl moiety from farnesyl diphosphate to a cysteine at the fourth position from the C-terminus of several prote...
Gene Name
FNTB
Uniprot ID
P49356
Uniprot Name
Protein farnesyltransferase subunit beta
Molecular Weight
48773.2 Da
References
  1. 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. [Article]

Drug created at September 15, 2010 21:33 / Updated at June 12, 2020 16:52