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Details

Stereochemistry ACHIRAL
Molecular Formula C20H20NO4
Molecular Weight 338.3771
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of JATRORRHIZINE

SMILES

COC1=CC2=C(CC[N+]3=CC4=C(C=CC(OC)=C4OC)C=C23)C=C1O

InChI

InChIKey=MXTLAHSTUOXGQF-UHFFFAOYSA-O
InChI=1S/C20H19NO4/c1-23-18-5-4-12-8-16-14-10-19(24-2)17(22)9-13(14)6-7-21(16)11-15(12)20(18)25-3/h4-5,8-11H,6-7H2,1-3H3/p+1

HIDE SMILES / InChI

Molecular Formula C20H19NO4
Molecular Weight 337.3692
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Jatrorrhizine is an active component of the traditional Chinese herb Coptis chinensis, which has been used to prevent and treat metabolic disorders. It is also found plants such as Enantia chlorantha, Thalictrum lucidumm, Thalictrum revolutum. Jatrorrhizine possesses antifungal, antibacterial activity. It has low toxicity and was studied in mouse models of obesity and hypercholesterolemia. The mechanism of action of Jatrorrhizine is not fully elucidated. The compound blocks alpha-1 and alpha-2 adrenoreceptors, monoamine oxidase A and B.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.0 µM [IC50]
62.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
In the model of hyperlipidemia, jatrorrhizine was administered by intragastric injections at up to 100 mg/kg body weight.
Route of Administration: Intragastric
In Vitro Use Guide
Antifungal activity of jatrorrhizine was tested on dermatophytes and yeast strains isolated from superficial human lesions. The solution of jatrorrhizine was added to Sabouraud 2% dextrose agar. 5 μl of the suspension of each active growing test fungus was inoculated on the surface of testing and control agar plates and incubated for 15 days at 25 ± 1 °C. Two days after the fungi started growth on control plates the minimal inhibitory concentration was determined as the lowest tested concentration that inhibited visible growth of the test fungi.
Substance Class Chemical
Record UNII
091S1F8V5Q
Record Status Validated (UNII)
Record Version