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Details

Stereochemistry ABSOLUTE
Molecular Formula C13H18O2
Molecular Weight 206.2808
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 3
Charge 0

SHOW SMILES / InChI
Structure of AUREONITOL

SMILES

C\C=C\C=C\[C@H]1CO[C@@H](\C=C\C=C)[C@@H]1O

InChI

InChIKey=DTLKTHCXEMHTIQ-DBCNHVMASA-N
InChI=1S/C13H18O2/c1-3-5-7-8-11-10-15-12(13(11)14)9-6-4-2/h3-9,11-14H,2,10H2,1H3/b5-3+,8-7+,9-6+/t11-,12-,13+/m0/s1

HIDE SMILES / InChI

Molecular Formula C13H18O2
Molecular Weight 206.2808
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 3
Optical Activity UNSPECIFIED

Aureonitol is a fungi-derived natural product, which is inhibited influenza A and B virus replication. This compound was more effective against influenza A(H3N2), with an EC50 of 100 nM. Aureonitol inhibited influenza hemagglutination and, consequently, significantly impaired virus adsorption. Molecular modeling studies revealed that aureonitol docked in the sialic acid binding site of hemagglutinin, forming hydrogen bonds with highly conserved residues

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibitory effects of rolipram on partially purified phosphodiesterase 4 from rat brains.
1998 Jun
Aureonitol, a Fungi-Derived Tetrahydrofuran, Inhibits Influenza Replication by Targeting Its Surface Glycoprotein Hemagglutinin.
2015

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Aureonitol inhibited influenza replication 24 h after infection with the A(H3N2) subtype in a dose-dependent fashion, with EC50 values of 30, 100 and 183 nM at MOIs of 0.01, 0.05 and 0.01, respectively . At 48 h after infection, aureonitol's potency was slightly reduced, as the obtained EC50 values were 48, 121 and 201 nM for MOIs of 0.01, 0.05 and 0.1, respectively. For comparison, at 24 post-infection OST presented EC50 values of 12, 30 and 49 nM for MOIs of 0.01, 0.05 and 0.1, respectively. At 48 h after infection, the EC50 concentration for OST also increased slightly to 28, 38 and 56 nM for MOIs of 0.01, 0.05 and 0.1, respectively.
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:19:13 GMT 2023
Edited
by admin
on Sat Dec 16 11:19:13 GMT 2023
Record UNII
23F04FI61S
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AUREONITOL
Common Name English
(-)-AUREONITOL
Systematic Name English
3-FURANOL, 2-(1,3-BUTADIEN-1-YL)TETRAHYDRO-4-(1,3-PENTADIEN-1-YL)-, (2S,3R,4S)-
Systematic Name English
Code System Code Type Description
CAS
71774-51-1
Created by admin on Sat Dec 16 11:19:13 GMT 2023 , Edited by admin on Sat Dec 16 11:19:13 GMT 2023
PRIMARY
EPA CompTox
DTXSID601038840
Created by admin on Sat Dec 16 11:19:13 GMT 2023 , Edited by admin on Sat Dec 16 11:19:13 GMT 2023
PRIMARY
PUBCHEM
25064137
Created by admin on Sat Dec 16 11:19:13 GMT 2023 , Edited by admin on Sat Dec 16 11:19:13 GMT 2023
PRIMARY
FDA UNII
23F04FI61S
Created by admin on Sat Dec 16 11:19:13 GMT 2023 , Edited by admin on Sat Dec 16 11:19:13 GMT 2023
PRIMARY