NAV

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

Identification

Generic Name
(4aS)-5-[(2,4-diaminopteridin-6-yl)methyl]-4a,5-dihydro-2H-dibenzo[b,f]azepin-8-ol
DrugBank Accession Number
DB08448
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 385.4219
Monoisotopic: 385.165108265
Chemical Formula
C21H19N7O
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDihydrofolate reductaseNot 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 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
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Substituents
1-hydroxy-2-unsubstituted benzenoid / Amine / Aminopyrimidine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azepine / Benzazepine / Benzenoid / Dialkylarylamine
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Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
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[9.4.0.0^{3,8}]pentadeca-3,5,7,9,11,14-hexaen-6-ol
SMILES
[H][C@]12C=CCC=C1C=CC1=CC(O)=CC=C1N2CC1=NC2=C(N)N=C(N)N=C2N=C1

References

General References
Not Available
PubChem Compound
46937152
PubChem Substance
99444919
ChemSpider
25058626
ZINC
ZINC000039112944
PDBe Ligand
Q22
PDB Entries
3d80

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 Solubility0.188 mg/mLALOGPS
logP2.44ALOGPS
logP2.33Chemaxon
logS-3.3ALOGPS
pKa (Strongest Acidic)10.16Chemaxon
pKa (Strongest Basic)1.81Chemaxon
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/MSsplash10-000i-0109000000-5911f71df1950cf40bdc
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0009000000-f999bb69068162a4c19d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0209000000-4e3595d0531a5d854e82
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-02ai-0039000000-f45640dacb515b4654f7
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002u-0903000000-33538bc62fbfcb287366
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0296-2927000000-82b13efc3575a9ccaab9
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-188.2151
predicted
DeepCCS 1.0 (2019)
[M+H]+190.57309
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.82661
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Dihydrofolate reductase
Kind
Protein
Organism
Humans
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. [Article]

Drug created at September 15, 2010 21:31 / Updated at June 12, 2020 16:52