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1,4:3,6-Dianhydro-2-O-(3-carbamimidoylphenyl)-5-O-(4-carbamimidoylphenyl)-D-glucitol

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Overview

Structure
DrugBank ID
DB04793
Type
Small Molecule
US Approved
NO
Other Approved
NO
Patents
0
Indicated Conditions
0
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
1,4:3,6-Dianhydro-2-O-(3-carbamimidoylphenyl)-5-O-(4-carbamimidoylphenyl)-D-glucitol
DrugBank Accession Number
DB04793
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 382.4131
Monoisotopic: 382.164105212
Chemical Formula
C20H22N4O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USerine protease 1Not 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
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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 isosorbides. These are organic polycyclic compounds containing an isosorbide(1,4-Dianhydrosorbitol) moiety, which consists of two -oxolan-3-ol rings.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Furofurans
Sub Class
Isosorbides
Direct Parent
Isosorbides
Alternative Parents
Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / Tetrahydrofurans / Oxacyclic compounds / Dialkyl ethers / Carboximidamides / Carboxamidines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Alkyl aryl ether / Amidine / Aromatic heteropolycyclic compound / Benzenoid / Carboximidamide / Carboxylic acid amidine / Dialkyl ether / Ether / Hydrocarbon derivative / Isosorbide
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DKBAWRNTUZFJKV-XMTFNYHQSA-N
InChI
InChI=1S/C20H22N4O4/c21-19(22)11-4-6-13(7-5-11)27-15-9-25-18-16(10-26-17(15)18)28-14-3-1-2-12(8-14)20(23)24/h1-8,15-18H,9-10H2,(H3,21,22)(H3,23,24)/t15-,16+,17-,18-/m1/s1
IUPAC Name
4-{[(3R,3aR,6S,6aR)-6-(3-carbamimidoylphenoxy)-hexahydrofuro[3,2-b]furan-3-yl]oxy}benzene-1-carboximidamide
SMILES
[H]N=C(N([H])[H])C1=CC=C(O[C@@H]2CO[C@]3([H])[C@H](CO[C@]23[H])OC2=CC=CC(=C2)C(=N[H])N([H])[H])C=C1

References

General References
Not Available
PubChem Compound
5326927
PubChem Substance
46504675
ChemSpider
4484210
ZINC
ZINC000003990709
PDBe Ligand
TL4
PDB Entries
1y5u

Clinical Trials

Clinical Trials
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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 Solubility0.0524 mg/mLALOGPS
logP0.35ALOGPS
logP1.1Chemaxon
logS-3.9ALOGPS
pKa (Strongest Basic)11.89Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area136.66 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity123.25 m3·mol-1Chemaxon
Polarizability40.17 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9752
Blood Brain Barrier+0.9268
Caco-2 permeable-0.6791
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.8734
P-glycoprotein inhibitor IINon-inhibitor0.9213
Renal organic cation transporterNon-inhibitor0.5291
CYP450 2C9 substrateNon-substrate0.8266
CYP450 2D6 substrateNon-substrate0.7745
CYP450 3A4 substrateNon-substrate0.6573
CYP450 1A2 substrateNon-inhibitor0.5182
CYP450 2C9 inhibitorNon-inhibitor0.742
CYP450 2D6 inhibitorNon-inhibitor0.6897
CYP450 2C19 inhibitorNon-inhibitor0.5681
CYP450 3A4 inhibitorNon-inhibitor0.8474
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5739
Ames testNon AMES toxic0.5458
CarcinogenicityNon-carcinogens0.8874
BiodegradationNot ready biodegradable0.9919
Rat acute toxicity2.3477 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9725
hERG inhibition (predictor II)Non-inhibitor0.8902
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/MSsplash10-00lr-0009000000-e53f819b61a756dd1436
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-01q9-0039000000-4c0fd26e8649e6474b58
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0019000000-5c34f6b4d275d6f1127f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000f-9732000000-711d06e2b08f9ffeffb4
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9621000000-18582aa30fe57523246a
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00xr-0915000000-bcd491beafd374d23abc
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]-181.0859
predicted
DeepCCS 1.0 (2019)
[M+H]+183.1273
predicted
DeepCCS 1.0 (2019)
[M+Na]+189.03981
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Serine protease 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form against all of these substrates
Specific Function
metal ion binding
Gene Name
PRSS1
Uniprot ID
P07477
Uniprot Name
Serine protease 1
Molecular Weight
26557.88 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 11, 2007 17:49 / Updated at June 12, 2020 16:52