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Lanosterol information


Lanosterol
Ball-and-stick model of lanosterol
Names
IUPAC name
Lanosta-8,24-dien-3β-ol
Systematic IUPAC name
(1R,3aR,5aR,7S,9aS,11aR)-3a,6,6,9a,11a-Pentamethyl-1-[(2R)-6-methylhept-5-en-2-yl]-2,3,3a,4,5,5a,6,7,8,9,9a,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol
Identifiers
CAS Number
  • 79-63-0 checkY
3D model (JSmol)
  • Interactive image
Beilstein Reference
2226449
ChEBI
  • CHEBI:16521 checkY
ChEMBL
  • ChEMBL225111 checkY
ChemSpider
  • 216175 checkY
DrugBank
  • DB03696
ECHA InfoCard 100.001.105 Edit this at Wikidata
EC Number
  • 201-214-9
IUPHAR/BPS
  • 2746
KEGG
  • C01724
MeSH Lanosterol
PubChem CID
  • 246983
UNII
  • 1J05Z83K3M checkY
CompTox Dashboard (EPA)
  • DTXSID1040744 Edit this at Wikidata
InChI
  • InChI=1S/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1 checkY
    Key: CAHGCLMLTWQZNJ-BQNIITSRSA-N checkY
  • InChI=1/C30H50O/c1-20(2)10-9-11-21(3)22-14-18-30(8)24-12-13-25-27(4,5)26(31)16-17-28(25,6)23(24)15-19-29(22,30)7/h10,21-22,25-26,31H,9,11-19H2,1-8H3/t21-,22-,25+,26+,28-,29-,30+/m1/s1
    Key: CAHGCLMLTWQZNJ-BQNIITSRBP
SMILES
  • C[C@H](CCC=C(C)C)[C@H]1CC[C@]2(C)C1CCC3=C2CC[C@H]4C(C)(C)[C@@H](O)CC[C@]34C
Properties
Chemical formula
C30H50O
Molar mass 426.71 g/mol
Melting point 138 to 140 °C (280 to 284 °F; 411 to 413 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Lanosterol is a tetracyclic triterpenoid and is the compound from which all animal and fungal steroids are derived. By contrast, plant steroids are produced via cycloartenol.[1]

  1. ^ Schaller, Hubert (May 2003). "The role of sterols in plant growth and development". Progress in Lipid Research. 42 (3): 163–175. doi:10.1016/S0163-7827(02)00047-4. PMID 12689617.

and 25 Related for: Lanosterol information

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Lanosterol

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Lanosterol is a tetracyclic triterpenoid and is the compound from which all animal and fungal steroids are derived. By contrast, plant steroids are produced...

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Lanosterol synthase

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cation and finally to lanosterol. Lanosterol is a key four-ringed intermediate in cholesterol biosynthesis. In humans, lanosterol synthase is encoded by...

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Steroid

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are manufactured in cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization...

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Terbinafine

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the conversion of squalene to lanosterol. In fungi, lanosterol is then converted to ergosterol; in humans, lanosterol becomes cholesterol. However, as...

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Isoprene

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(vitamin E), dolichols, and squalene. Heme A has an isoprenoid tail, and lanosterol, the sterol precursor in animals, is derived from squalene and hence from...

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Oxidosqualene cyclase

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cycloartenol Lanosterol synthase (LAS), found in all animals and fungi, and occasionally in plants, which produces primarily lanosterol Sterols and triterpenes...

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Prochloraz

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Similarly to other azole fungicides, prochloraz is an inhibitor of the enzyme lanosterol 14α-demethylase (CYP51A1), which is necessary for the production of ergosterol...

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Ergosterol

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synthesis of ergosterol from lanosterol by interfering with 14α-demethylase. Ergosterol is a smaller molecule than lanosterol; it is synthesized by combining...

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Cytochrome P450

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Synthase 1), and CYP51A1, lanosterol 14-α-demethylase, sometimes unofficially abbreviated to LDM according to its substrate (Lanosterol) and activity (DeMethylation)...

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Antifungal

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Rimocidin Azole antifungals inhibit conversion of lanosterol to ergosterol by inhibition of lanosterol 14α-demethylase. These compounds have a five-membered...

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Cycloartenol

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the steroids of fungi and animals, which are, instead, produced from lanosterol. The biosynthesis of cycloartenol starts from the triterpenoid squalene...

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Steroidogenesis inhibitor

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from lanosterol. Ergosterol is absent in animals but is an essential component of the cell membranes of many fungi and protozoa, and so lanosterol 14α-demethylase...

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Althaea officinalis

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along with the known phytoconstituents lauric acid, β-sitosterol and lanosterol. Marshmallows are used in gardening as ornamental plants. The leaves,...

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Karl Barry Sharpless

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Barry (1968). Studies of the mechanism of action of 2,3-oxidosqualene-lanosterol cyclase: featuring enzymic cyclization of modified squalene oxides (Ph...

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Sorbitol

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Diethylpropanediol Ethylene glycol Trialcohols Glycerol Sterols Cholesterol Ergosterol Lanosterol β-Sitosterol Stigmasterol Fluoroalcohols 1,3-Difluoro-2-propanol 2,2,2-Trifluoroethanol...

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Fluconazole

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binding, while still allowing binding of the enzyme's natural substrate, lanosterol. Development of resistance to one azole in this way will confer resistance...

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Triterpene

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cucurbitane core, although in practice they are biosynthesised from either lanosterol (animals and fungi) or cycloartenol (plants) via the cyclization of squalene...

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Limonene

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Tocopherols Cholesterol Testosterone Cholecalciferol Ecdysones Other Betulin Lanosterol Saponins Serratenediol Squalane Acids Oleanolic acid Ursolic acid Betulinic...

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Cholesterol

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steps. This is followed by 19 additional steps to convert the resulting lanosterol into cholesterol. A human male weighing 68 kg (150 lb) normally synthesizes...

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Squalene

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3-oxidosqualene. It then undergoes an enzyme-catalysed cyclisation to produce lanosterol, which can be elaborated into other steroids such as cholesterol and ergosterol...

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Lipid

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squalene and then folded up and formed into a set of rings to make lanosterol. Lanosterol can then be converted into other steroids such as cholesterol and...

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Clotrimazole

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component of the fungal cell membrane, by inhibiting the P450 enzyme lanosterol 14-alpha demethylase. Clotrimazole may slow fungal growth or result in...

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Itraconazole

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inhibits the fungal-mediated synthesis of ergosterol, via inhibition of lanosterol 14α-demethylase. Because of its ability to inhibit cytochrome P450 3A4...

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Terconazole

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the cytochrome P450 enzyme lanosterol of fungi, also known as CYP3A4. The gene ERG11 controls lanosterol creation. Lanosterol is found within the yeast...

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Inonotus obliquus

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Cultivated chaga developed a reduced number of phytosterols, particularly lanosterol, an intermediate in the synthesis of ergosterol and lanostane-type triterpenes...

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