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Details

Stereochemistry ABSOLUTE
Molecular Formula C20H22O7
Molecular Weight 374.3845
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of WIKSTROMOL

SMILES

COC1=C(O)C=CC(C[C@@H]2COC(=O)[C@@]2(O)CC3=CC(OC)=C(O)C=C3)=C1

InChI

InChIKey=ZITBJWXLODLDRH-JLTOFOAXSA-N
InChI=1S/C20H22O7/c1-25-17-8-12(3-5-15(17)21)7-14-11-27-19(23)20(14,24)10-13-4-6-16(22)18(9-13)26-2/h3-6,8-9,14,21-22,24H,7,10-11H2,1-2H3/t14-,20-/m1/s1

HIDE SMILES / InChI

Molecular Formula C20H22O7
Molecular Weight 374.3845
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Wikstromol is the enantiomer of nortrachelogenin, isolated from Trachelospermum asiaticum var. intermedium and Pinus palustris. Wikstromol exhibited acetylcholinesterase (AChE) inhibitory. It has been found to be active against P-388 lymphocytic leukemia growth implanted in mice. The reason for this is at present unclear, although it is possible that wikstromol is either metabolized to an active antileukemic agent by the host or else serves as a biological response modifier.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
PubMed

PubMed

TitleDatePubMed
(+)-Nortrachelogenin, A New Pharmacologically Active Lignan From Wikstroemia indica.
1979 Mar
(+)Nortrachelogenin, a new pharmacologically active lignan from Wikstroemia indica.
1979 Mar-Apr
(+)-Nortrachelogenin, a new pharmacologically active lignan from Wikstroemia indica.
1979 Mar-Apr
Antitumor agents. 49 tricin, kaempferol-3-O-beta-D-glucopyranoside and (+)-nortrachelogenin, antileukemic principles from Wikstroemia indica.
1981 Sep-Oct
Stereoselectivity questions in the synthesis of wikstromol.
1990 Nov-Dec
Antifungal, antimitotic and anti-HIV-1 agents from the roots of Wikstroemia indica.
2000 Aug
Enantioselective synthesis of (-)-wikstromol using a new approach via malic acid.
2001 Apr 6
Patents

Sample Use Guides

Mice: 60 or 100 mg/30 mg of thiopental
Route of Administration: Unknown
Wikstromol demonstrated moderate activity against HIV-1 in vitro with IC(50)s ranger from 4.02 to 5.74 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:38:28 GMT 2023
Edited
by admin
on Sat Dec 16 08:38:28 GMT 2023
Record UNII
5HG1T9G09U
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
WIKSTROMOL
Common Name English
2(3H)-FURANONE, DIHYDRO-3-HYDROXY-3,4-BIS((4-HYDROXY-3-METHOXYPHENYL)METHYL)-, (3R,4R)-
Systematic Name English
(+)-NORTRACHELOGENIN
Common Name English
(3R-CIS)-DIHYDRO-3,4-BIS((4-HYDROXY-3-METHOXYPHENYL)METHYL)-3-HYDROXY-2(3H)-FURANONE
Systematic Name English
Code System Code Type Description
FDA UNII
5HG1T9G09U
Created by admin on Sat Dec 16 08:38:28 GMT 2023 , Edited by admin on Sat Dec 16 08:38:28 GMT 2023
PRIMARY
CAS
61521-74-2
Created by admin on Sat Dec 16 08:38:28 GMT 2023 , Edited by admin on Sat Dec 16 08:38:28 GMT 2023
PRIMARY
PUBCHEM
479756
Created by admin on Sat Dec 16 08:38:28 GMT 2023 , Edited by admin on Sat Dec 16 08:38:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID70977093
Created by admin on Sat Dec 16 08:38:28 GMT 2023 , Edited by admin on Sat Dec 16 08:38:28 GMT 2023
PRIMARY