U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C13H20O3
Molecular Weight 224.2961
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of VOMIFOLIOL, (+)-

SMILES

C[C@@H](O)\C=C\[C@@]1(O)C(C)=CC(=O)CC1(C)C

InChI

InChIKey=KPQMCAKZRXOZLB-KOIHBYQTSA-N
InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+/t10-,13-/m1/s1

HIDE SMILES / InChI

Molecular Formula C13H20O3
Molecular Weight 224.2961
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including Nat. Prod. Lett. 1999, 14, 77−81 | http://www.tandfonline.com/doi/abs/10.1080/10575639908045437

4-Hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-2-cyclohexen-1-one, (4S,3R)-(E)-(±)- (Blumenol A) is a major secondary metabolite initially isolated from the leaves of Annona glabra L. (Annonaceae), commonly known as pond apple, which is a tropical tree distributed mainly in the Americas and in Southeast Asia, and used in traditional medicine as an insecticide and a parasiticide. Blumenol A was reported to display inhibitory activity against a panel of human solid tumor cell lines

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Metabolites from carnivorous fungus Arthrobotrys entomopaga and their functional roles in fungal predatory ability.
2013-05-01
[Vomifoliol: terpene alcohol isolated from leaves of Rauwolfia vomitoria Afz].
1969-03
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
Vomifoliol was dissolved in 80% EtOH to a final concentration of 2 mg/mL. 5 μL of extract was impregnated into sterile Whatman No. 1 filter paper discs (6 mm diameter) and dried under a stream of sterile air. The bacterial pathogen N. gonorrhoeae (ATCC 49226 from ATCC as Kwik-STK™ plus microorganism) with viable counts reaching 10^8 CFU/mL was then streaked with sterile swabs onto Petri dishes containing chocolate (GC) agar base medium (CMO367, Oxoid Ltd., England) supplemented with 2% (w/v) hemoglobin and 1% (v/v) Vitox and the plates dried for 5 min at room temperature. The procedure was done in triplicate. Ciprofloxacin (1 μg/disc) was used as a positive control, while H2O and 80% EtOH were used as negative and solvent controls, respectively. Discs were applied to the dry surface of a Petri dish containing GC agar base medium and bacteria.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:19:53 GMT 2025
Edited
by admin
on Mon Mar 31 21:19:53 GMT 2025
Record UNII
P86438KC5J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VOMIFOLIOL, (+)-
Common Name English
(+)-BLUMENOL A
Preferred Name English
2-CYCLOHEXEN-1-ONE, 4-HYDROXY-4-(3-HYDROXY-1-BUTENYL)-3,5,5-TRIMETHYL-, (+)-
Systematic Name English
(6S,7E,9R)-6,9-DIHYDROXY-4,7-MEGASTIGMADIEN-3-ONE
Common Name English
ROSEOSIDE AGLYCON
Common Name English
2-CYCLOHEXEN-1-ONE, 4-HYDROXY-4-((1E,3R)-3-HYDROXY-1-BUTENYL)-3,5,5-TRIMETHYL-, (4S)-
Systematic Name English
VOMIFOLIOL
Common Name English
(6S,9R)-6-HYDROXY-3-OXO-.ALPHA.-IONOL
Common Name English
2-CYCLOHEXEN-1-ONE, 4-HYDROXY-4-(3-HYDROXY-1-BUTENYL)-3,5,5-TRIMETHYL-, (S-(R*,S*-(E)))-
Common Name English
(6S,9R)-VOMIFOLIOL
Common Name English
2-CYCLOHEXEN-1-ONE, 4-HYDROXY-4-((1E,3R)-3-HYDROXY-1-BUTEN-1-YL)-3,5,5-TRIMETHYL-, (4S)-
Systematic Name English
(+)-VOMIFOLIOL
Common Name English
Code System Code Type Description
CAS
23526-45-6
Created by admin on Mon Mar 31 21:19:53 GMT 2025 , Edited by admin on Mon Mar 31 21:19:53 GMT 2025
PRIMARY
CHEBI
28258
Created by admin on Mon Mar 31 21:19:53 GMT 2025 , Edited by admin on Mon Mar 31 21:19:53 GMT 2025
PRIMARY
FDA UNII
P86438KC5J
Created by admin on Mon Mar 31 21:19:53 GMT 2025 , Edited by admin on Mon Mar 31 21:19:53 GMT 2025
PRIMARY
EPA CompTox
DTXSID601009964
Created by admin on Mon Mar 31 21:19:54 GMT 2025 , Edited by admin on Mon Mar 31 21:19:54 GMT 2025
PRIMARY
MESH
C525026
Created by admin on Mon Mar 31 21:19:53 GMT 2025 , Edited by admin on Mon Mar 31 21:19:53 GMT 2025
PRIMARY
CHEBI
49164
Created by admin on Mon Mar 31 21:19:53 GMT 2025 , Edited by admin on Mon Mar 31 21:19:53 GMT 2025
PRIMARY
PUBCHEM
5280462
Created by admin on Mon Mar 31 21:19:53 GMT 2025 , Edited by admin on Mon Mar 31 21:19:53 GMT 2025
PRIMARY