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Identification
Name(20S)-19,20,22,23-TETRAHYDRO-19-OXO-5H,21H-18,20-ETHANO-12,14-ETHENO-6,10-METHENOBENZ[D]IMIDAZO[4,3-L][1,6,9,13]OXATRIAZACYCLONOADECOSINE-9-CARBONITRILE
Accession NumberDB08676
TypeSmall Molecule
GroupsExperimental
DescriptionNot Available
Structure
Thumb
SynonymsNot Available
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
UNIINot Available
CAS numberNot Available
WeightAverage: 453.5356
Monoisotopic: 453.216475133
Chemical FormulaC27H27N5O2
InChI KeyInChIKey=GBEQWWUQNVMGMR-PSUQPPDWSA-N
InChI
InChI=1S/C27H27N5O2/c28-14-20-5-4-18-12-26(20)34-22-7-6-19-2-1-3-25(23(19)13-22)32-11-9-24(27(32)33)30-10-8-21-15-29-17-31(21)16-18/h1-4,6-7,13,15,17,20,24,26,30H,5,8-12,16H2/t20-,24+,26+/m1/s1
IUPAC Name
(5S,18R,19S)-31-oxo-20-oxa-2,6,11,13-tetraazahexacyclo[19.6.2.1²,⁵.1¹⁵,¹⁹.0⁹,¹³.0²⁴,²⁸]hentriaconta-1(27),9,11,15,21,23,25,28-octaene-18-carbonitrile
SMILES
[H][C@]12CCN(C1=O)C1=CC=CC3=CC=C(O[C@@]4([H])CC(CN5C=NC=C5CCN2)=CC[C@]4([H])C#N)C=C13
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassMacrolactams
Sub ClassNot Available
Direct ParentMacrolactams
Alternative Parents
Substituents
  • Macrolactam
  • Naphthalene
  • Alpha-amino acid or derivatives
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • 2-pyrrolidone
  • Pyrrolidone
  • N-substituted imidazole
  • Heteroaromatic compound
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Imidazole
  • Azole
  • Tertiary amine
  • Lactam
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Nitrile
  • Carbonitrile
  • Ether
  • Secondary aliphatic amine
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9247
Caco-2 permeable+0.5389
P-glycoprotein substrateSubstrate0.5842
P-glycoprotein inhibitor IInhibitor0.5
P-glycoprotein inhibitor IINon-inhibitor0.7926
Renal organic cation transporterInhibitor0.5326
CYP450 2C9 substrateNon-substrate0.8502
CYP450 2D6 substrateNon-substrate0.7377
CYP450 3A4 substrateSubstrate0.6391
CYP450 1A2 substrateInhibitor0.5888
CYP450 2C9 inhibitorInhibitor0.5905
CYP450 2D6 inhibitorNon-inhibitor0.7424
CYP450 2C19 inhibitorInhibitor0.5249
CYP450 3A4 inhibitorNon-inhibitor0.68
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7791
Ames testNon AMES toxic0.5258
CarcinogenicityNon-carcinogens0.9084
BiodegradationNot ready biodegradable0.9939
Rat acute toxicity2.6690 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6561
hERG inhibition (predictor II)Non-inhibitor0.5678
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.116 mg/mLALOGPS
logP2.43ALOGPS
logP1.68ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)17.66ChemAxon
pKa (Strongest Basic)7.61ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.18 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity129.92 m3·mol-1ChemAxon
Polarizability49.25 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 diphosphate to a cysteine at the fourth position from the C-terminus of several proteins having the C-terminal sequence Cys-aliphatic-aliphatic-X. May positively regulate neuromuscular junction development...
Gene Name:
FNTA
Uniprot ID:
P49354
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. [PubMed:10592235 ]
Kind
Protein
Organism
Human
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 proteins having the C-terminal sequence Cys-aliphatic-aliphatic-X.
Gene Name:
FNTB
Uniprot ID:
P49356
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. [PubMed:10592235 ]
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Drug created on September 15, 2010 15:33 / Updated on September 16, 2013 18:10