Stigmasterol






Names

    • AS-15473
    • .beta.-Stigmasterol
    • Stigmasta-5,22-dien-3.beta.-ol
    • GUINEA-PIG-ANTI-STIFFNESS FACTOR
    • s2361
    • 24aFH-stigmasta-5,22t-dien-3b-ol
    • Serposterol
    • STIGMASTEROL (CONSTITUENT OF SAW PALMETTO) [DSC]
    • Stigmasta-5,22-dien-3-ol, (3beta)-
    • MFCD00003630
    • STIGMASTEROL (CONSTITUENT OF SAW PALMETTO)
    • 1ST7509
    • (3S,8S,9S,10R,13R,14S,17R)-17-[(E,1R,4S)-4-ethyl-1,5-dimethyl-hex-2-enyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
    • Delta5-Stigmasterol
    • b-stigmasterol
    • Stigmasterol
    • CCRIS 7476
    • Stigmasta-5,22E-dien-3beta-ol
    • CHEMBL400247
    • stigmasta-5,22t-dien-3b-ol
    • NSC 8095
    • Stigmasterol, certified reference material, 10 mg/mL in chloroform
    • GLXC-13540
    • Delta5,22-Stigmastadien-3beta-ol
    • 5,22-Cholestadien-24-ethyl-3beta-ol
    • 24x-24-ethylcholest-5,22-dien-3b-ol
    • STIGMASTEROL (CONSTITUENT OF PYGEUM)
    • 99WUK5D0Y8
    • BRD-K41422683-001-02-2
    • STIGMASTEROL
    • (24S)-5,22-stigmastadien-3b-ol
    • STIGMASTEROL [MI]
    • STL570256
    • 83-48-7
    • C05442
    • Wulzen anti-stiffness factor
    • (24S)-Stigmast-5,22-dien-3beta-ol
    • NSC-8095
    • STIMASTEROL
    • stigmasta-5,22-dien-3-b-ol
    • HY-N0131
    • 3beta-HYDROXY-24-ETHYL-delta(SUP 5,22)-CHOLESTADIENE
    • beta-Stigmasterol
    • 3beta-Hydroxy-24-ethyl-5,22-cholestadiene
    • (24x)-ethylcholesta-5,22-dien-3b-ol
    • 5,22-Cholestadien-24beta-ethyl-3beta-ol
    • CHEBI:28824
    • 5,22-Stigmastadien-3beta-ol
    • (24aFH)-stigmasta-5,22t-dien-3b-ol
    • (24S)-5,22-Stigmastadien-3beta-ol
    • (24xH)-stigmasta-5,22t-dien-3b-ol
    • (3beta,22E)-Stigmasta-5,22-dien-3-ol
    • (3b,22E)-stigmasta-5,22-dien-3-ol
    • (3S,8S,9S,10R,13R,14S,17R)-17-[(E,2R,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
    • AKOS022168193
    • Stigmasta-5,22-dien-3-ol
    • (3.beta.,22E)-Stigmasta-5,22-dien-3-ol
    • SCHEMBL23999
    • Q-201746
    • 17-(4-ethyl-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
    • LMST01040123
    • CS-7746
    • (22E)-stigmasta-5,22-dien-3beta-ol
    • (24S)-24-Ethylcholesta-5,22-dien-3beta-ol
    • STIGMASTEROL [WHO-DD]
    • EINECS 201-482-7
    • D5-Stigmasterol
    • Stigmasta-5,22-dien-3beta-ol
    • (3S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-ethyl-6-methylhept-3-en-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
    • UNII-99WUK5D0Y8
    • .delta.5,22-Stigmastadien-3.beta.-ol
    • Stigmasterin
    • 24-Ethyl-5,22-cholestadien-3beta-ol
    • NCGC00142599-03
    • STIGMASTEROL [HSDB]
    • BDBM50376364
    • HB4095
    • 3.BETA.-HYDROXY-24-ETHYL-.DELTA.(SUP 5,22)-CHOLESTADIENE
    • Stigmasta-5,22-dien-3-ol, (3b,22E)-
    • HSDB 7683
    • Stigmasta-5,22-dien-3-beta-ol
    • .DELTA.5-STIGMASTEROL
    • DTXSID801015733
    • DTXCID601473919
    • STIGMASTEROL (CONSTITUENT OF PYGEUM) [DSC]
    • Q425004
    • Stigmasterol, ~95%
    • rac-(24xH)-stigmasta-5,22t-dien-3b-ol
    • 24-Ethyl-5,22-cholestadien-3.beta.-ol
    • 14-((2E)(4S,1R)-4-ethyl-1,5-dimethylhex-2-enyl)(1S,5S,10S,11S,2R,14R,15R)-2,15 -dimethyltetracyclo[8.7.0.0<2,7>.0<11,15>]heptadec-7-en-5-ol
    • Stigmasta-5,22-dien-3-ol, (3beta,22E)-

Attributes

  • Canonical SMILES

    CC[C@H](/C=C/[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/C29H48O/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/h8-10,19-21,23-27,30H,7,11-18H2,1-6H3/b9-8+/t20-,21-,23+,24+,25-,26+,27+,28+,29-/m1/s1

  • Molecule Class: Minor compounds
  • TPSA: 20.23
  • #RotBonds: 5
  • MW: 412.7020000000002
  • HBD: 1
  • HBA: 1
  • logP: 7.8008000000000095
  • Chemical Formula: C29H48O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862
    T. inconspicua Cameroon 761075 NHC61026
    T. ventricosa Kenya 761103 AM2017/04

External Databases


References

  • A New Antimicrobial Phenylpropanol from the Leaves of Tabernaemontana inconspicua Stapf. (Apocynaceae) Inhibits Pathogenic Gram-Negative Bacteria. Antibiotics (Basel), 2022 (PMID 35052998).
  • Antileishmanial and cytotoxic activity of secondary metabolites from Taberneamontana ventricosa and two aloe species. Nat Prod Res, 2022 (PMID 33459049).
  • 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
    • Antileishmanial
    • 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) -4.95
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.52
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.92
    Distribution Blood-Brain Barrier (Central Nervous System) -1.9
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.86
    Plasma Protein Binding 82.85
    Steady State Volume of Distribution 1.72
    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 7.91
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.24
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 1.75
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 6.29
    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 Toxic
    T. Pyriformis -33.77
    Rat (Acute) 2.38
    Rat (Chronic Oral) 1.92
    Fathead Minnow 4.04
    Respiratory Disease Toxic
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Toxic
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 408.59
    Hydration Free Energy -3.84
    Log(D) at pH=7.4 6.53
    Log(P) 8.75
    Log S -6.97
    Log(Vapor Pressure) -7.1
    Melting Point 144.19
    pKa Acid 13.14
    pKa Basic 7.95