Betulin






Names

    • Betulinic alcohol
    • BDBM23207
    • Lup-20(30)-ene-3beta ,28-diol
    • AI3-62999
    • CCG-208619
    • (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-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
    • Lup-20(29)-ene-3,28-diol, (3beta)-
    • CHEMBL23236
    • (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3 a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol
    • Lup-20(29)-ene-3 ,28-diol
    • NCGC00168803-01
    • BETULIN [MI]
    • MFCD00016802
    • lup-20(29)-ene-3 beta,28-diol
    • (3.beta.)-Lup-20(29)-ene-3,28-diol
    • C08618
    • NCGC00168803-04
    • NSC-692218
    • NS00018049
    • Betulin
    • NSC 4644
    • (1R,2R,5S,8R,9R,10R,13R,14R,17S,19R)-5-(hydroxymethyl)-1,2,14,18,18-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0^{2,10}.0^{5,9}.0^{14,19}]henicosan-17-ol
    • B0803
    • Lup-20(29)-ene-3beta ,28-diol
    • GS-3254
    • (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(Hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol
    • Trochol
    • (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-(hydroxymethyl)-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
    • BPBio1_001165
    • s4754
    • AB00513988
    • EX-A3354
    • DTXSID101019934
    • Betulol
    • Lup-20(30)-ene-3beta,28-diol
    • 6W70HN7X7O
    • MEGxp0_001726
    • BRD-K64874225-001-04-7
    • Lup-20(29)-ene-3,28-diol, (3.beta.)-
    • UNII-6W70HN7X7O
    • Lup-20(29)-ene-3,28-diol, (3beta )-
    • Betulin (Standard)
    • (+)-betulin
    • CP BETULIN
    • HY-N0083
    • Lup-20(29)-ene-3beta,28-diol
    • NSC692218
    • SR-05000002167-3
    • NSC4644
    • Betulin, 23
    • Lup-20(29)-ene-3.beta.,28-diol
    • (3beta)-lup-20(29)-ene-3,28-diol
    • NCGC00168803-02
    • ORISTRACT BTL
    • CHEBI:3086
    • Betulinol (obsol.)
    • Betulin, >=98%
    • EINECS 207-475-5
    • BSPBio_001059
    • 473-98-3
    • SR-05000002167
    • HMS2098E21
    • Betulin, analytical standard
    • LMPR0106140005
    • ACon1_000091
    • BRD-K64874225-001-01-3
    • NSC-4644
    • CS-6156
    • Betuline
    • AKOS005267212
    • Lup-20(29)-ene-3b,28-diol
    • Prestwick3_000990
    • Lup-20(30)-ene-3.beta.,28-diol
    • Q419726
    • Q-100501
    • Betulinol
    • SCHEMBL131739
    • HY-N0083R
    • SR-05000002167-2

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)CO

  • InChI

    InChI=1S/C30H50O2/c1-19(2)20-10-15-30(18-31)17-16-28(6)21(25(20)30)8-9-23-27(5)13-12-24(32)26(3,4)22(27)11-14-29(23,28)7/h20-25,31-32H,1,8-18H2,2-7H3/t20-,21+,22-,23+,24-,25+,27-,28+,29+,30+/m0/s1

  • Molecule Class: Terpenoids
  • TPSA: 40.46
  • #RotBonds: 2
  • MW: 442.7280000000003
  • HBD: 2
  • HBA: 2
  • logP: 6.997200000000009
  • Chemical Formula: C30H50O2


Species

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

External Databases


References

  • Chromatographic analysis and antioxidant capacity of Tabernaemontana catharinensis. Nat Prod Commun, 2014 (PMID 24660464).

Compound-Protein Relationships


Compound Activities

    • Antioxidant

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

    Category Property Name Predicted Value
    Absorption Caco-2 (logPaap) -4.83
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.45
    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) -1.7
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 1.48
    Plasma Protein Binding 84.98
    Steady State Volume of Distribution 1.46
    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 12.14
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor -0.26
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 1.63
    Liver Injury II Safe
    hERG Blockers Toxic
    Daphnia Maga 5.55
    Micronucleos Safe
    NR-AhR Safe
    NR-AR Toxic
    NR-AR-LBD Safe
    NR-Aromatase Safe
    NR-ER Safe
    NR-ER-LBD Safe
    NR-GR Toxic
    NR-PPAR-gamma Safe
    NR-TR Toxic
    T. Pyriformis -77.6
    Rat (Acute) 2.46
    Rat (Chronic Oral) 1.49
    Fathead Minnow 3.91
    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 409.02
    Hydration Free Energy -2.59
    Log(D) at pH=7.4 6.89
    Log(P) 7.33
    Log S -6.7
    Log(Vapor Pressure) -8.94
    Melting Point 234.37
    pKa Acid 12.59
    pKa Basic 7.78