(4aS)-5-[(2,4-diaminopteridin-6-yl)methyl]-4a,5-dihydro-2H-dibenzo[b,f]azepin-8-ol

Identification

Name
(4aS)-5-[(2,4-diaminopteridin-6-yl)methyl]-4a,5-dihydro-2H-dibenzo[b,f]azepin-8-ol
Accession Number
DB08448
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: 385.4219
Monoisotopic: 385.165108265
Chemical Formula
C21H19N7O
InChI Key
PCBWLKUEKANDCL-INIZCTEOSA-N
InChI
InChI=1S/C21H19N7O/c22-19-18-20(27-21(23)26-19)24-10-14(25-18)11-28-16-4-2-1-3-12(16)5-6-13-9-15(29)7-8-17(13)28/h2-10,16,29H,1,11H2,(H4,22,23,24,26,27)/t16-/m0/s1
IUPAC Name
(1S)-2-[(2,4-diaminopteridin-6-yl)methyl]-2-azatricyclo[9.4.0.0³,⁸]pentadeca-3,5,7,9,11,14-hexaen-6-ol
SMILES
[H][[email protected]]12C=CCC=C1C=CC1=CC(O)=CC=C1N2CC1=NC2=C(N)N=C(N)N=C2N=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UDihydrofolate reductaseNot 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
46937152
PubChem Substance
99444919
ChemSpider
25058626
HET
Q22
PDB Entries
3d80

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 Solubility0.188 mg/mLALOGPS
logP2.44ALOGPS
logP2.33ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)10.16ChemAxon
pKa (Strongest Basic)3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area127.07 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity117.42 m3·mol-1ChemAxon
Polarizability39.75 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9885
Blood Brain Barrier+0.9074
Caco-2 permeable+0.5094
P-glycoprotein substrateSubstrate0.7045
P-glycoprotein inhibitor INon-inhibitor0.8064
P-glycoprotein inhibitor IIInhibitor0.5052
Renal organic cation transporterInhibitor0.5136
CYP450 2C9 substrateNon-substrate0.8844
CYP450 2D6 substrateNon-substrate0.7647
CYP450 3A4 substrateNon-substrate0.5337
CYP450 1A2 substrateNon-inhibitor0.5229
CYP450 2C9 inhibitorNon-inhibitor0.693
CYP450 2D6 inhibitorNon-inhibitor0.698
CYP450 2C19 inhibitorNon-inhibitor0.7394
CYP450 3A4 inhibitorNon-inhibitor0.6254
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5903
Ames testAMES toxic0.5092
CarcinogenicityNon-carcinogens0.9268
BiodegradationNot ready biodegradable0.9941
Rat acute toxicity2.5366 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6917
hERG inhibition (predictor II)Non-inhibitor0.5676
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 benzazepines. These are organic compounds containing a benzene ring fused to an azepine ring (unsaturated seven-membered heterocycle with one nitrogen atom replacing a carbon atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzazepines
Sub Class
Not Available
Direct Parent
Benzazepines
Alternative Parents
Pteridines and derivatives / Dialkylarylamines / Azepines / Aralkylamines / Aminopyrimidines and derivatives / 1-hydroxy-2-unsubstituted benzenoids / Pyrazines / Imidolactams / Heteroaromatic compounds / Azacyclic compounds
show 4 more
Substituents
Benzazepine / Pteridine / Dialkylarylamine / Tertiary aliphatic/aromatic amine / Aminopyrimidine / 1-hydroxy-2-unsubstituted benzenoid / Azepine / Aralkylamine / Pyrazine / Imidolactam
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Nadph binding
Specific Function
Key enzyme in folate metabolism. Contributes to the de novo mitochondrial thymidylate biosynthesis pathway. Catalyzes an essential reaction for de novo glycine and purine synthesis, and for DNA pre...
Gene Name
DHFR
Uniprot ID
P00374
Uniprot Name
Dihydrofolate reductase
Molecular Weight
21452.61 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]

Drug created on September 15, 2010 15:31 / Updated on December 01, 2017 16:05