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

Details

Stereochemistry ABSOLUTE
Molecular Formula C26H40O8
Molecular Weight 480.591
Optical Activity UNSPECIFIED
Defined Stereocenters 9 / 9
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NEOANDROGRAPHOLIDE

SMILES

[H][C@]12CCC(=C)[C@@H](CCC3=CCOC3=O)[C@]1(C)CCC[C@@]2(C)CO[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O

InChI

InChIKey=YGCYRQKJYWQXHG-RDNQFMDVSA-N
InChI=1S/C26H40O8/c1-15-5-8-19-25(2,14-33-24-22(30)21(29)20(28)18(13-27)34-24)10-4-11-26(19,3)17(15)7-6-16-9-12-32-23(16)31/h9,17-22,24,27-30H,1,4-8,10-14H2,2-3H3/t17-,18-,19-,20-,21+,22-,24-,25+,26+/m1/s1

HIDE SMILES / InChI

Molecular Formula C26H40O8
Molecular Weight 480.591
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 9 / 9
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Neoandrographolide, one of the principal diterpene lactones, isolated from a medicinal herb Andrographis paniculata Nees. Andrographis paniculata (Burm. f.) Wall. ex Nees (Acanthaceae), also known as “kalmegh” in India, is a widely distributed plant in Asia. In many traditional formulations, the aerial parts have been used as anti-inflammatory and antipyretic drugs for the treatment of a variety of chronic and infectious diseases. Neoandrographolide possesses significant anti-inflammatory effects, which implies that it would be one of the major contributing components to participate in the anti-inflammatory effect of A. paniculata. and a potential candidate for further clinical trial.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct

PubMed

Sample Use Guides

In Vivo Use Guide
Ear Edema was induced in BALB/c mice by topical application of dimethyl benzene (50 mkl). Neoandrographolide was administered orally (50, 100 and 150 mg/kg) 1 hour before the application of dimethyl benzene.
Route of Administration: Oral
In Vitro Use Guide
Stimulation of RAW 264.7 macrophages with phorbol-12-myristate-13-acetate (PMA) resulted in detectable respiratory bursts measured by a luminol-enchanced method. neoandrographolide from 7.5 to 150 mkM, showed a dose dependent suppression of the respiratory burst effect on macrophages
Substance Class Chemical
Record UNII
XBY0Z806J2
Record Status Validated (UNII)
Record Version