Allosamidin

Identification

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Name
Allosamidin
Accession Number
DB04628
Type
Small Molecule
Groups
Experimental
Description

Allosamidin exhibits extremely potent inhibitory activity against chitinases from a number of sources, particularly from Candida albicans, and can be utilized as potent antifungal agent.

Structure
Thumb
Synonyms
Not Available
External IDs
A-82516 / A82516
Categories
UNII
Not Available
CAS number
103782-08-7
Weight
Average: 622.6194
Monoisotopic: 622.269752072
Chemical Formula
C25H42N4O14
InChI Key
MDWNFWDBQGOKNZ-XYUDZHFQSA-N
InChI
InChI=1S/C25H42N4O14/c1-8(33)26-14-17(36)16(35)11(6-31)39-23(14)42-22-12(7-32)40-24(15(19(22)38)27-9(2)34)41-21-10(5-30)20-13(18(21)37)28-25(43-20)29(3)4/h10-24,30-32,35-38H,5-7H2,1-4H3,(H,26,33)(H,27,34)/t10-,11+,12+,13+,14+,15+,16+,17-,18+,19-,20-,21+,22+,23-,24-/m0/s1
IUPAC Name
N-[(2R,3R,4S,5S,6R)-2-{[(3aR,4R,5R,6S,6aS)-2-(dimethylamino)-4-hydroxy-6-(hydroxymethyl)-3aH,4H,5H,6H,6aH-cyclopenta[d][1,3]oxazol-5-yl]oxy}-5-{[(2S,3R,4S,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-hydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
SMILES
CN(C)C1=N[C@@H]2[C@@H](O)[C@H](O[C@@H]3O[C@H](CO)[C@@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@@H](O)[C@H]4NC(C)=O)[C@@H](O)[C@H]3NC(C)=O)[C@@H](CO)[C@@H]2O1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UChitinase BNot AvailableSerratia marcescens
UChitinase ANot AvailableSerratia marcescens
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
KEGG Compound
C05346
PubChem Compound
119339
PubChem Substance
46506500
ChemSpider
106593
BindingDB
50331851
ChEMBL
CHEMBL1230997
HET
AO3
PDB Entries
1x6n / 4r5e / 6hm1

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 Solubility39.4 mg/mLALOGPS
logP-2.3ALOGPS
logP-5.8ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)11.81ChemAxon
pKa (Strongest Basic)6.81ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area261.56 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity138.71 m3·mol-1ChemAxon
Polarizability60.6 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8498
Blood Brain Barrier-0.9733
Caco-2 permeable-0.7417
P-glycoprotein substrateSubstrate0.6274
P-glycoprotein inhibitor INon-inhibitor0.5458
P-glycoprotein inhibitor IINon-inhibitor0.6126
Renal organic cation transporterNon-inhibitor0.8891
CYP450 2C9 substrateNon-substrate0.7213
CYP450 2D6 substrateNon-substrate0.8347
CYP450 3A4 substrateSubstrate0.6245
CYP450 1A2 substrateNon-inhibitor0.8156
CYP450 2C9 inhibitorNon-inhibitor0.8799
CYP450 2D6 inhibitorNon-inhibitor0.8943
CYP450 2C19 inhibitorNon-inhibitor0.8487
CYP450 3A4 inhibitorNon-inhibitor0.8214
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9228
Ames testNon AMES toxic0.6865
CarcinogenicityNon-carcinogens0.9044
BiodegradationNot ready biodegradable0.9726
Rat acute toxicity2.3879 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9536
hERG inhibition (predictor II)Non-inhibitor0.5713
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 n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbohydrates and carbohydrate conjugates
Direct Parent
N-acyl-alpha-hexosamines
Alternative Parents
Disaccharides / O-glycosyl compounds / Oxanes / Oxazolines / Acetamides / Secondary alcohols / Isoureas / Secondary carboxylic acid amides / Cyclic alcohols and derivatives / Acetals
show 9 more
Substituents
N-acyl-alpha-hexosamine / Disaccharide / Glycosyl compound / O-glycosyl compound / Oxane / Cyclic alcohol / Oxazoline / Acetamide / Secondary carboxylic acid amide / Secondary alcohol
show 19 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
N-acyl-hexosamine (CHEBI:40808)

Targets

Kind
Protein
Organism
Serratia marcescens
Pharmacological action
Unknown
General Function
Chitinase activity
Specific Function
Not Available
Gene Name
chiB
Uniprot ID
P11797
Uniprot Name
Chitinase B
Molecular Weight
55463.97 Da
References
  1. Cederkvist FH, Saua SF, Karlsen V, Sakuda S, Eijsink VG, Sorlie M: Thermodynamic analysis of allosamidin binding to a family 18 chitinase. Biochemistry. 2007 Oct 30;46(43):12347-54. Epub 2007 Oct 4. [PubMed:17915946]
  2. Vaaje-Kolstad G, Houston DR, Rao FV, Peter MG, Synstad B, van Aalten DM, Eijsink VG: Structure of the D142N mutant of the family 18 chitinase ChiB from Serratia marcescens and its complex with allosamidin. Biochim Biophys Acta. 2004 Jan 14;1696(1):103-11. [PubMed:14726210]
Kind
Protein
Organism
Serratia marcescens
Pharmacological action
Unknown
General Function
Chitinase activity
Specific Function
Not Available
Gene Name
chiA
Uniprot ID
P07254
Uniprot Name
Chitinase A
Molecular Weight
60978.56 Da

Drug created on September 11, 2007 11:49 / Updated on June 04, 2019 06:09