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Amarogentin

Amarogentin structure

CAS No:
21018-84-8
Formula:
C29H30O13
Chemical Name:
Amarogentin
Synonyms:
1H,3H-Pyrano[3,4-c]pyran-1-one,5-ethenyl-4,4a,5,6-tetrahydro-6-[[2-O-[(3,3′,5-trihydroxy[1,1′-biphenyl]-2-yl)carbonyl]-β-D-glucopyranosyl]oxy]-,(4aS,5R,6S)-;Amarogentin;[1,1′-Biphenyl]-2-carboxylic acid,3,3′,5-trihydroxy-,2-ester with 5-ethenyl-6-(β-D-glucopyranosyloxy)-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one,[4aS-(4aα,5β,6α)]-;1H,3H-Pyrano[3,4-c]pyran,[1,1′-biphenyl]-2-carboxylic acid deriv.;(4aS,5R,6S)-5-Ethenyl-4,4a,5,6-tetrahydro-6-[[2-O-[(3,3′,5-trihydroxy[1,1′-biphenyl]-2-yl)carbonyl]-β-D-glucopyranosyl]oxy]-1H,3H-pyrano[3,4-c]pyran-1-one;1H,3H-Pyrano[3,4-c]pyran-1-one,5-ethenyl-4,4a,5,6-tetrahydro-6-[[2-O-[(3,3′,5-trihydroxy[1,1′-biphenyl]-2-yl)carbonyl]-β-D-glucopyranosyl]oxy]-,[4aS-(4aα,5β,6α)]-;1397-87-1
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Amarogentin is a secoiridoid glycoside that is mainly extracted from Swertia and Gentiana roots. Amarogentin exhibits many biological effects, including anti-oxidative, anti-tumour, and anti-diabetic activities. Amarogentin exerts hepatoprotective and immunomodulatory effects. Amarogentin promotes apoptosis, arrests G2/M cell cycle and downregulates of PI3K/Akt/mTOR signalling pathways. Amarogentin exerts beneficial vasculo-metabolic effect by activating AMPK[1][2][3].

Amarogentin is a secoiridoid glycoside that consists of (4aS,5R,6R)-5-ethenyl-6-hydroxy-4,4a,5,6-tetrahydro-1H,3H-pyrano[3,4-c]pyran-1-one having a 2-O-[(3,3',5-trihydroxybiphenyl-2-yl)carbonyl]-beta-D-glucopyranosyl group attached at position 6 via a glycosidic linkage. It has a role as an EC 5.99.1.2 (DNA topoisomerase) inhibitor and a metabolite. It is a secoiridoid glycoside and a monosaccharide derivative.

Amarogentin Basic Attributes

Molecular Weight：

586.54

Exact Mass：

586.54

UNII：

5L82GT5I0W

Characteristics

PSA：

201.67000

XLogP3：

2.79

Density：

1.6±0.1 g/cm3

Melting Point：

178-180 °C

Boiling Point：

928.5±65.0 °C at 760 mmHg

Flash Point：

306.9±27.8 °C

Refractive Index：

1.693

Specific rotation：

D20 -116.6° (methanol)

Drug Information

MeSH Entry Terms：

amarogentin

Computed Properties

Molecular Weight:586.5
XLogP3:2.4
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:13
Rotatable Bond Count:8
Exact Mass:586.16864101
Monoisotopic Mass:586.16864101
Topological Polar Surface Area:202
Heavy Atom Count:42
Complexity:1020
Defined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Amarogentin

CAS No.: 21018-84-8

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