NAV

(4aS,4bR,10bS,12aS)-12a-methyl-1,3-dioxo-2-(pyridin-3-ylmethyl)-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho[2,1-f]isoquinolin-8-yl sulfamate

Identification

Generic Name
(4aS,4bR,10bS,12aS)-12a-methyl-1,3-dioxo-2-(pyridin-3-ylmethyl)-1,2,3,4,4a,4b,5,6,10b,11,12,12a-dodecahydronaphtho[2,1-f]isoquinolin-8-yl sulfamate
DrugBank Accession Number
DB08418
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 469.553
Monoisotopic: 469.167141679
Chemical Formula
C24H27N3O5S
Synonyms
Not Available
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCarbonic anhydrase 2Not 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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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 phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Phenanthrenes and derivatives
Sub Class
Not Available
Direct Parent
Phenanthrenes and derivatives
Alternative Parents
Isoquinolones and derivatives / Tetralins / Piperidinediones / Delta lactams / Pyridines and derivatives / N-substituted carboxylic acid imides / Organic sulfuric acids and derivatives / Heteroaromatic compounds / Dicarboximides / Azacyclic compounds
show 5 more
Substituents
Aromatic heteropolycyclic compound / Azacycle / Carbonyl group / Carboxylic acid derivative / Carboxylic acid imide / Carboxylic acid imide, n-substituted / Delta-lactam / Dicarboximide / Heteroaromatic compound / Hydrocarbon derivative
show 16 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
LSJKARAMQNGZDF-YOEKFXIASA-N
InChI
InChI=1S/C24H27N3O5S/c1-24-9-8-19-18-7-5-17(32-33(25,30)31)11-16(18)4-6-20(19)21(24)12-22(28)27(23(24)29)14-15-3-2-10-26-13-15/h2-3,5,7,10-11,13,19-21H,4,6,8-9,12,14H2,1H3,(H2,25,30,31)/t19-,20-,21+,24+/m1/s1
IUPAC Name
(4aS,4bR,10bS,12aS)-12a-methyl-1,3-dioxo-2-[(pyridin-3-yl)methyl]-1H,2H,3H,4H,4aH,4bH,5H,6H,10bH,11H,12H,12aH-naphtho[2,1-f]isoquinolin-8-yl sulfamate
SMILES
[H][C@]12CC[C@]3(C)C(=O)N(CC4=CC=CN=C4)C(=O)C[C@@]3([H])[C@]1([H])CCC1=C2C=CC(OS(N)(=O)=O)=C1

References

General References
Not Available
PubChem Compound
9912519
PubChem Substance
99444889
ChemSpider
8088170
BindingDB
50121192
ChEMBL
CHEMBL1235380
ZINC
ZINC000003988972
PDBe Ligand
POF
PDB Entries
3c7p

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 Solubility0.0287 mg/mLALOGPS
logP2.65ALOGPS
logP2.4Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)10.85Chemaxon
pKa (Strongest Basic)4.81Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area119.66 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity121.2 m3·mol-1Chemaxon
Polarizability49.15 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9794
Caco-2 permeable-0.6225
P-glycoprotein substrateSubstrate0.5489
P-glycoprotein inhibitor INon-inhibitor0.508
P-glycoprotein inhibitor IINon-inhibitor0.7992
Renal organic cation transporterNon-inhibitor0.6765
CYP450 2C9 substrateNon-substrate0.8745
CYP450 2D6 substrateNon-substrate0.7849
CYP450 3A4 substrateSubstrate0.6322
CYP450 1A2 substrateNon-inhibitor0.7506
CYP450 2C9 inhibitorNon-inhibitor0.7402
CYP450 2D6 inhibitorNon-inhibitor0.8541
CYP450 2C19 inhibitorNon-inhibitor0.7292
CYP450 3A4 inhibitorNon-inhibitor0.7296
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7053
Ames testNon AMES toxic0.5589
CarcinogenicityNon-carcinogens0.5741
BiodegradationNot ready biodegradable0.988
Rat acute toxicity2.5850 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7208
hERG inhibition (predictor II)Inhibitor0.5054
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/MSsplash10-00di-0000900000-5298e9867ca733d330d3
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-2000900000-5893a9c38a210fed37c6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-007c-0009200000-c1a814ce31d8e7403330
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-9000500000-47e011c1293acc8066bc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0g4l-2289300000-8d9dd1682a6be5023435
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014j-9604600000-8e15ae585dc7662e4aec
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]-208.50694
predicted
DeepCCS 1.0 (2019)
[M+H]+210.40237
predicted
DeepCCS 1.0 (2019)
[M+Na]+216.52003
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Carbonic anhydrase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
Gene Name
CA2
Uniprot ID
P00918
Uniprot Name
Carbonic anhydrase 2
Molecular Weight
29245.895 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