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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H24O2
Molecular Weight 236.3499
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CURCUMOL

SMILES

[H][C@@]12CC[C@H](C)[C@@]13C[C@@H](C(C)C)[C@@](O)(CC2=C)O3

InChI

InChIKey=QRMPRVXWPCLVNI-YYFQZIEXSA-N
InChI=1S/C15H24O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h9,11-13,16H,3,5-8H2,1-2,4H3/t11-,12-,13-,14-,15+/m0/s1

HIDE SMILES / InChI

Molecular Formula C15H24O2
Molecular Weight 236.3499
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27125675

Curcumol is one of the major components of the essential oil of Rhizome Curcumae with the structure of sesquiterpenoid hemiketal. It exhibits characteristics such as antitumor, ant proliferation, anti-inflammatory, anti-hepatic fibrosis, antioxidant, and antimicrobial activities with low cytotoxicity. Curcumol suppresses the Breast Cancer Cells, Colorectal Cancer Cell Line, lung adenocarcinoma cell lines and others. However, its effect and mechanisms against tumor metastasis are still unclear. Recently was discovered a preliminary mechanism the suppression of breast cancer cell metastasis by curcumol. This mechanism suggested the inhibition of MMP-9 via JNK1/2 and Akt (Ser473)-dependent NF-κB signaling pathways.

Originator

Curator's Comment: In 1965, for the first time, a Japanese scholar named Hiroshi Hikino isolated curcumol from the volatile oil of C. zedoaria Roscoe

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Curcumol Suppresses Breast Cancer Cell Metastasis by Inhibiting MMP-9 Via JNK1/2 and Akt-Dependent NF-κB Signaling Pathways.
2016 Jun

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
To explore the anti-cell proliferation mechanism of curcumol the changes of Jak2-STAT1/3 signal pathway-related molecules in synoviocytes were observed in vitro. In this study, the fibroblast-like synoviocytes (FLS) in patients with RA were collected and cultured. The following parameters were measured: cell proliferation (WST-1 assay in the presence of different concentrations of curcumol: 25, 50, 100, 200, 400, and 800 g/mL), cell cycles (fluorescence-activated cell sorting, FACS in the presence of different concentration of curcumol: 25, 50, 100 g/mL), STAT1 and STAT3 activities (electrophoretic mobility shift assay, EMSA), and the protein expressions of phosphorylated Jak2, STAT1, and STAT3 (Western blot). It was shown, that certain concentration of curcumol ranging from 25 g/mL to 100 g/mL could inhibit the RA-FLS proliferation and DNA synthesis induced by PDGF-BB in a dose-dependent manner in vitro. The fibroblast-like synoviocytes (FLS)
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:30:38 GMT 2023
Edited
by admin
on Sat Dec 16 02:30:38 GMT 2023
Record UNII
9190RTN07X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CURCUMOL
Common Name English
6H-3A,6-EPOXYAZULEN-6-OL, OCTAHYDRO-3-METHYL-8-METHYLENE-5-(1-METHYLETHYL)-, (3S,3AS,5S,6R,8AS)-
Common Name English
6H-3A,6-EPOXYAZULEN-6-OL, OCTAHYDRO-3-METHYL-8-METHYLENE-5-(1-METHYLETHYL)-, (3S-(3.ALPHA.,3A.ALPHA.,5.BETA.,6.BETA.,8A.BETA.))-
Common Name English
(-)-CURCUMOL
Common Name English
5.BETA.-GUAI-10(14)-EN-8-OL, 5,8-EPOXY-, (-)-
Common Name English
Code System Code Type Description
PUBCHEM
14240392
Created by admin on Sat Dec 16 02:30:38 GMT 2023 , Edited by admin on Sat Dec 16 02:30:38 GMT 2023
PRIMARY
FDA UNII
9190RTN07X
Created by admin on Sat Dec 16 02:30:38 GMT 2023 , Edited by admin on Sat Dec 16 02:30:38 GMT 2023
PRIMARY
CAS
4871-97-0
Created by admin on Sat Dec 16 02:30:38 GMT 2023 , Edited by admin on Sat Dec 16 02:30:38 GMT 2023
PRIMARY
EPA CompTox
DTXSID50964108
Created by admin on Sat Dec 16 02:30:38 GMT 2023 , Edited by admin on Sat Dec 16 02:30:38 GMT 2023
PRIMARY