(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

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
Accession Number
DB08418
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: 469.553
Monoisotopic: 469.167141679
Chemical Formula
C24H27N3O5S
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
(1R,2S,7S,10S)-7-methyl-4,6-dioxo-5-(pyridin-3-ylmethyl)-5-azatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-11(16),12,14-trien-14-yl sulfamate
SMILES
[H][[email protected]]12CC[[email protected]]3(C)C(=O)N(CC4=CC=CN=C4)C(=O)C[[email protected]@]3([H])[[email protected]]1([H])CCC1=C2C=CC(OS(N)(=O)=O)=C1

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCarbonic anhydrase 2Not 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
9912519
PubChem Substance
99444889
ChemSpider
8088170
ChEMBL
CHEMBL1235380
HET
POF
PDB Entries
3c7p

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 Solubility0.0287 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
Polarizability49.05 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/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 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
Phenanthrene / Isoquinolone / Tetralin / Piperidinedione / Delta-lactam / Piperidinone / Carboxylic acid imide, n-substituted / Piperidine / Pyridine / Carboxylic acid imide
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on September 15, 2010 15:31 / Updated on December 01, 2017 16:04