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Friedelin

Friedelin structure

Friedelin 

structure
  • CAS No:

    559-74-0

  • Formula:

    C30H50O

  • Chemical Name:

    Friedelin

  • Synonyms:

    24,25,26-Trinoroleanan-3-one,5,9,13-trimethyl-,(4β,5β,8α,9β,10α,13α,14β)-;D:A-Friedooleanan-3-one;Friedelin;(4β,5β,8α,9β,10α,13α,14β)-5,9,13-Trimethyl-24,25,26-trinoroleanan-3-one;(-)-Friedelin;Friedelan-3-one;Friedeline;Friedelanone;3(2H)-Picenone,eicosahydro-4,4a,6b,8a,11,11,12b,14a-octamethyl-,[4R-(4α,4aα,6aβ,6bα,8aα,12aα,12bβ,14aα,14bβ)]-;3(2H)-Picenone,eicosahydro-4,4a,6b,8a,11,11,12b,14a-octamethyl-,(4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-;NSC 55141;3-Oxofriedelane

  • Categories:

    Natural Products  >  Terpenes

Description

Friedelin is isolated from isolated from the leaves of Maytenus ilicifolia(Mart). Friedelin is a noncompetitive inhibitor of CYP3A4 with IC50 and Kivalues of 10.79  μM and 6.16  μM, respectively. Friedelin is also a competitive inhibitor of CYP2E1 with IC50 and Ki values of 22.54  μM and 18.02 μM, respectively[1].


Friedelin is a pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork. It has a role as an anti-inflammatory drug, a non-narcotic analgesic, an antipyretic and a plant metabolite. It is a pentacyclic triterpenoid and a cyclic terpene ketone.

Friedelin Basic Attributes

426.72

426.72

209-205-1

AK21264UAD

Characteristics

17.1

10.87

1.0±0.1 g/cm3

263 °C

477.2±13.0 °C at 760 mmHg

233.9±12.1 °C

1.503

2-8°C

D -27.8° (chloroform)

Safety Information

NONH for all modes of transport

3

Drug Information

friedelanone

Computed Properties

Molecular Weight:426.7
XLogP3:9.8
Hydrogen Bond Acceptor Count:1
Exact Mass:426.386166214
Monoisotopic Mass:426.386166214
Topological Polar Surface Area:17.1
Heavy Atom Count:31
Complexity:781
Defined Atom Stereocenter Count:9
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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