Lupeol






Names

    • Triterpene lupeol
    • 1ST40145
    • (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
    • Lup-20(29)-en-3-ol, (3beta)-
    • 3.BETA.-HYDROXYLUP-20(29)-ENE
    • Lupenol
    • Lup-20(29)-en-3-ol, (3b)-
    • (3-beta)-Lup-20(29)-en-3-ol
    • MFCD00017351
    • 3beta-lup-20(29)-en-3-ol
    • DTXSID901025006
    • Lupeol
    • NCGC00168853-06
    • s3614
    • Fagarsterol
    • (+)-Lupeol
    • CHEMBL289191
    • Clerodol
    • EINECS 208-889-9
    • 545-47-1
    • CCG-268968
    • LUPEOL [MI]
    • BDBM50377927
    • O268W13H3O
    • DB12622
    • Lup-20(29)-en-3-ol, (3-beta)-
    • Q409366
    • C08628
    • Lupeol, >=94%
    • Lup-20(29)-en-3b-ol
    • Lup-20(29)-en-3-beta-ol
    • DS-3391
    • Fagarasterol
    • 3beta-HYDROXYLUP-20(29)-ENE
    • CHEBI:6570
    • HSDB 7687
    • NSC-90487
    • LUPEOL, (+)-
    • (3beta)-lup-20(29)-en-3-ol
    • LUPEOL [HSDB]
    • NSC90487
    • Monogynol B
    • (3-.BETA.)-LUP-20(29)-EN-3-OL
    • HY-N0790
    • LUP-20(29)-EN-3-OL, (3-.BETA.)-
    • Lup-20(29)-en-3.beta.-ol
    • AKOS016008524
    • .beta.-Viscol
    • L0321
    • NS00043298
    • beta-Viscol
    • Lup-20(29)-en-3beta-ol
    • Lup-20(29)-en-3-ol
    • Q-100615
    • farganasterol
    • LUP-20(29)-EN-3-.BETA.-OL
    • NCGC00168853-07
    • Lupeol, analytical standard
    • UNII-O268W13H3O
    • Lupeol (Standard)
    • 20(29)-Lupen-3beta-ol
    • NCI60_042005
    • HY-N0790R
    • (1R,3aR,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
    • NSC 90487
    • SCHEMBL148518
    • Lup-20(29)-en-3-ol, (3.beta.)-
    • CS-7563
    • LMPR0106130001

Attributes

  • Canonical SMILES

    CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]3CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O)C)C

  • InChI

    InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20-,21+,22-,23+,24-,25+,27+,28-,29+,30+/m0/s1

  • Molecule Class: Terpenoids
  • TPSA: 20.23
  • #RotBonds: 1
  • MW: 426.72900000000027
  • HBD: 1
  • HBA: 1
  • logP: 8.02480000000001
  • Chemical Formula: C30H50O


Species

    Species Place of Collection NCBI Taxonomy Voucher Specimen
    T. catharinensis Brazil 403124 UEC117862
    T. contorta Cameroon 761060 N43440/HNC
    T. inconspicua Cameroon 761075 NHC61026

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).
  • Chromatographic analysis and antioxidant capacity of Tabernaemontana catharinensis. Nat Prod Commun, 2014 (PMID 24660464).
  • Contortamide, a new anti-colon cancer cerebroside and other constituents from Tabernaemontana contorta Stapf (Apocynaceae). Nat Prod Res, 2021 (PMID 31274013).
  • HPLC analysis and antimicrobial, antimycobacterial and antiviral activities of Tabernaemontana catharinensis A. DC Journal of Applied Biomedicine, 2015 (DOI).

Compound-Protein Relationships


Compound Activities

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

Predicted NMR Spectral Data


Predicted MS Fragmentation Patternn


Predicted ADMET Properties

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -4.78
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.42
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.77
    Distribution Blood-Brain Barrier (Central Nervous System) -1.89
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.69
    Plasma Protein Binding 87.89
    Steady State Volume of Distribution 1.64
    Metabolism Breast Cancer Resistance Protein 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 11.9
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.56
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 1.93
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 5.97
    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 -43.61
    Rat (Acute) 2.29
    Rat (Chronic Oral) 1.41
    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 398.07
    Hydration Free Energy -3.23
    Log(D) at pH=7.4 7.78
    Log(P) 8.55
    Log S -7.17
    Log(Vapor Pressure) -8.0
    Melting Point 218.75
    pKa Acid 13.28
    pKa Basic 8.08