Friedeline






Names

    • (-)-Friedelin
    • 24,25,26-trinoroleanan-3-one, 5,9,13-trimethyl-, (4beta,5beta,8alpha,9beta,10alpha,13alpha,14beta)-
    • SR-05000002227
    • 559-74-0
    • Friedelin
    • D:A-Friedooleanan-3-one (VAN) (8CI)(9CI)
    • C08626
    • 24,25,26-TRINOROLEANAN-3-ONE, 5,9,13-TRIMETHYL-, (4.BETA.,5.BETA.,8.ALPHA.,9.BETA.,10.ALPHA.,13.ALPHA.,14.BETA.)-
    • (4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-4,4a,6b,8a,11,11,12b,14a-octamethylicosahydropicen-3(2H)-one
    • friedelanone
    • Friedelin (Standard)
    • CHEMBL485998
    • Friedelan-3-one
    • DTXSID101015732
    • D:A-Friedooleanan-3-one
    • 3-OXOFRIEDELANE
    • Fridelin
    • HY-N4110
    • CHEBI:5171
    • AK21264UAD
    • Friedelin, technical grade
    • 24,25,26-Trinoroleanan-3-one, 5,9,13-trimethyl-,(4b,5b,8a,9b,10a,13a,14b)-
    • DTXCID901473918
    • 3(2H)-PICENONE, EICOSAHYDRO-4,4A,6B,8A,11,11,12B,14A-OCTAMETHYL-, (4R-(4.ALPHA.,4A.ALPHA.,6A.BETA.,6B.ALPHA.,8A.ALPHA.,12A.ALPHA.,12B.BETA.,14A.ALPHA.,14B.BETA.))-
    • EINECS 209-205-1
    • CCG-208470
    • SR-05000002227-3
    • SCHEMBL193053
    • Friedeline
    • (4R,4aS,6aS,6aS,6bR,8aR,12aR,14aS,14bS)-4,4a,6a,6b,8a,11,11,14a-octamethyl-2,4,5,6,6a,7,8,9,10,12,12a,13,14,14b-tetradecahydro-1H-picen-3-one
    • D:A-Friedooleanan-3-one (VAN) (8CI)
    • Friedelin, analytical standard
    • UNII-AK21264UAD
    • BDBM50241943
    • NS00043099
    • Q15410972
    • CS-0032118
    • HY-N4110R
    • D:A-Friedooleanan-3-one (VAN)
    • SR-05000002227-2
    • MS-27536
    • 3(2H)-Picenone, eicosahydro-4,4a,6b,8a,11,11,12b,14a-octamethyl-, (4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS)-
    • AKOS015897124
    • MFCD00017296
    • FRIEDELIN [MI]
    • NSC-55141
    • 3(2H)-PICENONE, EICOSAHYDRO-4,4A,6B,8A,11,11,12B,14A-OCTAMETHYL-, (4R-(4ALPHA,4AALPHA,6ABETA,6BALPHA,8AALPHA,12AALPHA,12BBETA,14AALPHA,14BBETA))-
    • NSC 55141
    • OFMXGFHWLZPCFL-SVRPQWSVSA-N

Attributes

  • Canonical SMILES

    C[C@H]1C(=O)CC[C@@H]2[C@@]1(CC[C@H]3[C@]2(CC[C@@]4([C@@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C)C)C)C)C

  • InChI

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

  • Molecule Class: Terpenoids
  • TPSA: 17.07
  • #RotBonds: 0
  • MW: 426.72900000000027
  • HBD: 0
  • HBA: 1
  • logP: 8.457000000000006
  • Chemical Formula: C30H50O


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).

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

    Property Model Name Predicted Value
    Absorption Caco-2 (logPaap) -4.76
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.5
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.39
    Distribution Blood-Brain Barrier (Central Nervous System) -2.29
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 2.09
    Plasma Protein Binding 88.78
    Steady State Volume of Distribution 1.8
    Metabolism Breast Cancer Resistance Protein Inhibitor
    CYP 1A2 Inhibitor Non-Inhibitor
    CYP 1A2 substrate 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 11.68
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.66
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Toxic
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose 1.64
    Liver Injury II Toxic
    hERG Blockers Toxic
    Daphnia Maga 6.09
    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 -32.23
    Rat (Acute) 2.11
    Rat (Chronic Oral) 1.46
    Fathead Minnow 3.92
    Respiratory Disease Safe
    Skin Sensitisation Toxic
    SR-ATAD5 Safe
    SR-ARE Safe
    SR-HSE Safe
    SR-MMP Safe
    SR-p53 Safe
    General Properties Boiling Point 428.42
    Hydration Free Energy -3.66
    Log(D) at pH=7.4 7.35
    Log(P) 7.53
    Log S -6.91
    Log(Vapor Pressure) -7.95
    Melting Point 249.13
    pKa Acid 12.32
    pKa Basic 7.59