β-Sitosterol






Names

    • Beta-Sitosterol (purity>98%)
    • SKF 14463
    • SITOSTEROL, BETA
    • (3S,8S,9S,10R,13R,14S,17R)-17-[(1R,4R)-4-ethyl-1,5-dimethyl-hexyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
    • A840577
    • sitosterin
    • BETA-SITOSTEROL (CONSTITUENT OF STINGING NETTLE) [DSC]
    • Nimbosterol
    • beta Sitosterol
    • 24.alpha.-Ethylcholesterol
    • 5-Stigmasten-3beta-ol
    • NS00078818
    • BSPBio_001049
    • NCGC00142598-03
    • Betaprost
    • alpha-Dihydrofucosterol
    • 22,23-Dihydrostigmasterol
    • SITOSTEROL, BETA-
    • 24.BETA.-ETHYL-.DELTA.(SUP 5)-CHOLESTEN-3.BETA.-OL
    • 5-cholesten-24-ethyl-3-ol
    • BETA-SITOSTEROL [USP-RS]
    • Sitosterol beta
    • BIDD:ER0636
    • Harzol
    • .alpha.-Phytosterol
    • ACon1_000287
    • beta -Sitosterol
    • .beta.-Sitosterin
    • .beta.-Sitosterol
    • ss--Sitosterol
    • Stigmast-5-en-3b-ol
    • s2273
    • (3beta)-Stigmast-5-en-3-ol
    • beta-Sitosterol, analytical standard, from soybean, >=40%
    • .beta.Sitosterin
    • 22,23-dihydro-Stigmasterol
    • AB00513984
    • .BETA.-SITOSTEROL [MI]
    • Q63409374
    • HY-N0171R
    • Beta-sitosterol, European Pharmacopoeia (EP) Reference Standard
    • 1ST40101
    • NSC-821067
    • MFCD00003631
    • (24R)-Stigmast-5-en-3b-ol
    • NSC18173
    • NCGC00142598-08
    • -Sitosterol (purity>98%);22,23-Dihydrostigmasterol (purity>98%)
    • BDBM50218197
    • LMST01040129
    • (3S,8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
    • (-)-b-Sitosterol
    • BIDD:PXR0121
    • BETA-SITOSTEROL, inverted exclamation markY 98% (HPLC)
    • NSC 8096
    • Prestwick3_000985
    • Cupreol
    • .BETA.-SITOSTEROL (CONSTITUENT OF PYGEUM) [DSC]
    • beta-Sitosterol, certified reference material, 100 mug/mL in chloroform
    • BETA-SITOSTEROL (CONSTITUENT OF SAW PALMETTO) [DSC]
    • a-Dihydrofucosterol
    • 14-((1S,4R)-4-ethyl-1,5-dimethylhexyl)(1S,5S,10S,11S,2R,14R,15R)-2,15-dimethyl tetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-7-en-5-ol
    • HMS2098E11
    • BETA SITOSTEROL [VANDF]
    • Stigmast-5-en-3-ol, (3beta)-
    • NSC-8096
    • AA-504/07226009
    • Sitosterol, .beta.
    • SPBio_002950
    • CAS-83-46-5
    • beta-Sitosterol, >=70%
    • Harzol (TN)
    • MEGxp0_001710
    • beta-Sitosterol, primary pharmaceutical reference standard
    • SR-05000002307-2
    • 83-46-5
    • Beta-sistosterol
    • SR-05000002307
    • BETA-SITOSTEROL (CONSTITUENT OF SAW PALMETTO)
    • .DELTA.(SUP 5)-STIGMASTEN-3.BETA.-OL
    • Triastonal
    • 24a-Ethylcholesterol
    • 17-(5-ethyl-6-methyl-heptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
    • NCGC00095716-01
    • BETA-SITOSTEROL, 40% (HPLC)
    • BRD-K79402892-001-06-7
    • BETA-SITOSTEROL
    • NCI60_041777
    • SCHEMBL16105
    • (3.BETA.)-STIGMAST-5-EN-3-OL
    • SITOSTEROL (MART.)
    • Azuprostat
    • SITOSTEROL [MART.]
    • a-Phytosterol
    • DB14038
    • I2-sitosterol
    • (-)-beta-Sitosterol
    • D5-Stigmasten-3b-ol
    • Sitosterol
    • beta-SITOSTEROL (CONSTITUENT OF ECHINACEA ANGUSTIFOLIA ROOT, ECHINACEA PALLIDA ROOT, ECHINACEA PURPUREA ROOT AND ECHINACEA PURPUREA AERIAL PARTS)
    • HMS1571E11
    • Stigmasterol,23-dihydro-
    • Q-200712
    • CCRIS 5529
    • Stigmast-5-en-3beta-ol
    • CHEMBL221542
    • S347WMO6M4
    • UNII-S347WMO6M4
    • CHEBI:27693
    • Beta-sitosterol [WHO-DD]
    • Beta-Sitosterol (Standard)
    • 3 beta-stigmast-5-en-3-ol
    • S0040
    • Quebrachol
    • NSC-18173
    • 24-Ethylcholest-5-en-3.beta.-ol
    • Cupreol , Beta-Sitosterol , |A-Sitosterol , Azuprostat , SKF 14463 , 22,23-Dihydrostigmasterol , Betaprost
    • (3S,8S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
    • beta-Phytosterol
    • SMP1_000274
    • beta-Sitosterol, from soybean, >=96%
    • Corn sterilized quantitative extract (beta sitosterol)
    • SR-05000002307-3
    • β-Sitosterol
    • EINECS 201-480-6
    • DTXSID5022481
    • b-Sitosterin
    • C01753
    • (24R)-Ethylcholest-5-en-3beta-ol
    • Prestwick0_000985
    • BPBio1_001155
    • Cinchol
    • Rhamnol
    • (3S,9S,10R,13R,14S,17R)-17-((2R,5R)-5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
    • NSC 18173
    • (24R)-Ethylcholest-5-en-3b-ol
    • 24beta-ETHYL-delta(SUP 5)-CHOLESTEN-3beta-OL
    • 76772-70-8
    • NSC821067
    • AT37227
    • alpha-Dihydrofucosterol, 22,23-Dihydrostigmasterol
    • 24alpha-Ethylcholesterol
    • Stigmasterol, 22,23-dihydro-
    • AKOS005267194
    • Prestwick2_000985
    • beta-SITOSTEROL (CONSTITUENT OF PYGEUM)
    • AI3-26020
    • NSC49083
    • alpha-Phytosterol
    • Angelicin (steroid)
    • .alpha.-Dihydrofucosterol
    • NCGC00142598-02
    • CCG-208334
    • B-Sitosterol
    • NSC8096
    • DTXCID802481
    • Stigmast-5-en-3.beta.-ol
    • Prostasal
    • Stigmast-5-en-3-ol, (3b)-
    • beta-Sitosterol, synthetic, >=95%
    • BETA-SITOSTEROL (CONSTITUENT OF STINGING NETTLE)
    • Prestwick1_000985
    • (3-beta)-Stigmast-5-en-3-ol
    • BETA-SITOSTEROL (USP-RS)
    • beta-Sitosterol, United States Pharmacopeia (USP) Reference Standard
    • AC-24183
    • NSC-49083
    • beta-Sitosterin
    • .beta.Sitosterol
    • CHEBI:176889
    • Delta5-Stigmasten-3b-ol
    • alpha.Dihydrofucosterol
    • Stigmast-5-en-3-ol, (3.beta.)-
    • Sobatum
    • (24R)-Stigmast-5-en-3beta-ol
    • delta5-Stigmasten-3-beta-ol
    • Beta-Sitosterol-2
    • Sito-Lande
    • b-Sitosterol (Synthetic)
    • Stigmast-5-en-3-beta-ol
    • beta-Sitosterol, analytical standard
    • Tox21_111514
    • 24-alpha-Ethylcholesterol
    • delta(SUP 5)-STIGMASTEN-3beta-OL
    • D08518

Attributes

  • Canonical SMILES

    CC[C@H](CC[C@@H](C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(C)C

  • InChI

    InChI=1S/C29H50O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h10,19-21,23-27,30H,7-9,11-18H2,1-6H3/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

  • Molecule Class: Terpenoids
  • TPSA: 20.23
  • #RotBonds: 6
  • MW: 414.71800000000025
  • HBD: 1
  • HBA: 1
  • logP: 8.02480000000001
  • Chemical Formula: C29H50O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862

External Databases


References

  • Chemical composition and antioxidant activity of the essential oil of Tabernaemontana catharinensis A. DC. leaves. Nat Prod Res, 2013 (PMID 22273350).
  • Chromatographic analysis and antioxidant capacity of Tabernaemontana catharinensis. Nat Prod Commun, 2014 (PMID 24660464).
  • HPLC analysis and antimicrobial, antimycobacterial and antiviral activities of Tabernaemontana catharinensis A. DC Journal of Applied Biomedicine, 2015 (DOI).

Compound-Protein Relationships


Compound Activities

    • Antimycobacterial
    • Antiviral
    • Antiherpes
    • Antimicrobial
    • Antiherpetic
    • Antioxidant
    • Cytotoxicity

Predicted NMR Spectral Data


Predicted MS Fragmentation Pattern

    N.B.: It is recommended to zoom in on a specific area of an MS plot before hovering on a peak.

Predicted ADMET Properties

    Property Model Name Predicted Value
    Absorption Caco-2 (logPaap) -4.96
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.44
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.91
    Distribution Blood-Brain Barrier (Central Nervous System) -2.12
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.76
    Plasma Protein Binding 83.49
    Steady State Volume of Distribution 1.62
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Non-Inhibitor
    CYP 2C19 substrate Substrate
    CYP 2C9 Inhibitor Non-Inhibitor
    CYP 2C9 Substrate Non-Substrate
    CYP 2D6 Inhibitor Non-Inhibitor
    CYP 2D6 Substrate Non-Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 10.95
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.02
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 2.07
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 6.22
    Micronucleos Safe
    NR-AhR Safe
    NR-AR Toxic
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Safe
    NR-PPAR-gamma Safe
    NR-TR Safe
    T. Pyriformis -33.89
    Rat (Acute) 2.19
    Rat (Chronic Oral) 1.92
    Fathead Minnow 3.92
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 407.0
    Hydration Free Energy -3.84
    Log(D) at pH=7.4 6.64
    Log(P) 8.99
    Log S -6.92
    Log(Vapor Pressure) -7.25
    Melting Point 142.71
    pKa Acid 13.6
    pKa Basic 8.5