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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H14O3
Molecular Weight 278.3026
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIHYDROTANSHINONE I

SMILES

Cc1cccc2c1ccc3c2C(=O)C(=O)C4=C3OC[C@]4([H])C

InChI

InChIKey=HARGZZNYNSYSGJ-JTQLQIEISA-N
InChI=1S/C18H14O3/c1-9-4-3-5-12-11(9)6-7-13-15(12)17(20)16(19)14-10(2)8-21-18(13)14/h3-7,10H,8H2,1-2H3/t10-/m0/s1

HIDE SMILES / InChI

Molecular Formula C18H14O3
Molecular Weight 278.3026
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Dihydrotanshinone I (DHI), a diterpenoid first isolated from the roots of Salvia miltiorrhiza, is a relatively high affinity inhibitor of human AChE. Dihydrotanshinone I (10 and 25 mg/kg) significantly attenuates atherosclerotic plaque formation, alteres serum lipid profile, decreases oxidative stress and shrinks necrotic core areas in ApoE-/- mice. Dihydrotanshinone I dramatically inhibits the enhanced expression of LOX-1, NOX4, and NF-κB in aorta. Dihydrotanshinone I treatment can improve cardiac function, reduce infarct size, ameliorate the variations in myocardial zymogram and histopathological disorders, decrease 20-HETE generation, and regulate apoptosis-related protein in myocardial ischemia-reperfusion rats.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.6 µM [Ki]
0.72 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Structures of human acetylcholinesterase bound to dihydrotanshinone I and territrem B show peripheral site flexibility.
2013 Nov 14
Dihydrotanshinone I Attenuates Atherosclerosis in ApoE-Deficient Mice: Role of NOX4/NF-κB Mediated Lectin-Like Oxidized LDL Receptor-1 (LOX-1) of the Endothelium.
2016
The cardioprotection of dihydrotanshinone I against myocardial ischemia-reperfusion injury via inhibition of arachidonic acid ω-hydroxylase.
2016 Dec
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: Mice were dosed daily via intragastric gavage
Mice: Dihydrotanshinone I (10 and 25 mg/kg) significantly attenuates atherosclerotic plaque formation, alteres serum lipid profile, decreases oxidative stress and shrinks necrotic core areas in ApoE-/- mice.
Route of Administration: Intragastric
In lipopolysaccharide (LPS)-stimulated human umbilical vein endothelial cells (HUVECs), Dihydrotanshinone I (10 nM) decreased lectin-like ox-LDL receptor-1 (LOX-1) and NADPH oxidase 4 (NOX4) expression, reactive oxygen species (ROS) production, NF-κB nuclear translocation, ox-LDL endocytosis and monocytes adhesion.
Substance Class Chemical
Created
by admin
on Sat Jun 26 12:14:06 UTC 2021
Edited
by admin
on Sat Jun 26 12:14:06 UTC 2021
Record UNII
562G9360V6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIHYDROTANSHINONE I
Common Name English
DIHYDROTANSHINONE (CONSTITUENT OF CHINESE SALVIA) [DSC]
Common Name English
DIHYDROTANSHINONE I, (-)-
Common Name English
PHENANTHRO(1,2-B)FURAN-10,11-DIONE, 1,2-DIHYDRO-1,6-DIMETHYL-, (1R)-
Systematic Name English
(-)-DIHYDROTANSHINONE I
Systematic Name English
Code System Code Type Description
HSDB
8105
Created by admin on Sat Jun 26 12:14:06 UTC 2021 , Edited by admin on Sat Jun 26 12:14:06 UTC 2021
PRIMARY
CAS
87205-99-0
Created by admin on Sat Jun 26 12:14:06 UTC 2021 , Edited by admin on Sat Jun 26 12:14:06 UTC 2021
PRIMARY
PUBCHEM
11425923
Created by admin on Sat Jun 26 12:14:06 UTC 2021 , Edited by admin on Sat Jun 26 12:14:06 UTC 2021
PRIMARY
EPA CompTox
87205-99-0
Created by admin on Sat Jun 26 12:14:06 UTC 2021 , Edited by admin on Sat Jun 26 12:14:06 UTC 2021
PRIMARY
FDA UNII
562G9360V6
Created by admin on Sat Jun 26 12:14:06 UTC 2021 , Edited by admin on Sat Jun 26 12:14:06 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT