Curcumenol






Names

    • s3874
    • Curcumenol
    • 6H-3a,6-Epoxyazulen-6-ol, 1,2,3,4,5,8a-hexahydro-3,8-dimethyl-5-(1-methylethylidene)-, (3S-(3-alpha,3a-alpha,6-alpha,8a-beta))-
    • (1S,2S,5S,8R)-2,6-dimethyl-9-propan-2-ylidene-11-oxatricyclo(6.2.1.01,5)undec-6-en-8-ol
    • Curcumenol6H-3a,6-Epoxyazulen-6-ol, 1,2,3,4,5,8a-hexahydro-3,8-dimethyl-5-(1-methylethylidene)-, (3S-(3-alpha,3a-alpha,6-alpha,8a-beta))-; 6H-3a,6-Epoxyazulen-6-ol,1,2,3,4,5,8a-hexahydro-3,8-dimethyl-5-(1-methylethylidene)-, (3S,3aS,6R,8aS)-; (1S,2S,5S,8R)-2,6-Dimethyl-9-propan-2-ylidene-11-oxatricyclo[6.2.1.01,5]undec-6-en-8-ol
    • 2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0^{1,5}]undec-6-en-8-ol
    • AS-76068
    • (1S,2S,5S,8R)-2,6-DIMETHYL-9-(PROPAN-2-YLIDENE)-11-OXATRICYCLO[6.2.1.0(1),?]UNDEC-6-EN-8-OL
    • CCG-266822
    • 19431-84-6
    • AKOS030529143
    • 9-isopropylidene-2,6-dimethyl-11-oxatricyclo(6.2.1.0^1,5^)undec-6-en-8-ol
    • BRN 3094585
    • 5,8-Epoxy-9-dien-8-.alpha.-ol-5-.beta.-guiaia-7(11)
    • DTXCID9031779
    • 1ST161454
    • HMS3885G10
    • 2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo(6.2.1.0^(1,5))undec-6-en-8-ol
    • CS-0019588
    • 5,8-Epoxy-9-dien-8-alpha-ol-5-beta-guiaia-7(11)
    • (+)-Curcumenol
    • 3,8-Dimethyl-5-(1-methylethylidene)-,(3S,3aS,6R,8aS)-
    • 6H-3a,6-Epoxyazulen-6-ol,1,2,3,4,5,8a-hexahydro-3,8-dimethyl-5-(1-methylethylidene)-, (3S,3aS,6R,8aS)-
    • DTXSID0058011
    • Q-100237
    • 5-beta-Guiaia-7(11),9-dien-8-alpha-ol, 5,8-epoxy-
    • AC-34181
    • 9-isopropylidene-2,6-dimethyl-11-oxatricyclo[6.2.1.0^1,5^]undec-6-en-8-ol
    • (1S,2S,5S,8R)-2,6-Dimethyl-9-propan-2-ylidene-11-oxatricyclo[6.2.1.01,5]undec-6-en-8-ol
    • HY-N2259

Attributes

  • Canonical SMILES

    C[C@H]1CC[C@@H]2[C@]13CC(=C(C)C)[C@](O3)(C=C2C)O

  • InChI

    InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h7,11-12,16H,5-6,8H2,1-4H3/t11-,12-,14-,15+/m0/s1

  • Molecule Class: Terpenoids
  • TPSA: 29.46
  • #RotBonds: 0
  • MW: 234.33899999999997
  • HBD: 1
  • HBA: 2
  • logP: 3.176500000000002
  • Chemical Formula: C15H22O2


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) -4.86
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.24
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.51
    Distribution Blood-Brain Barrier (Central Nervous System) -2.71
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.4
    Plasma Protein Binding 38.53
    Steady State Volume of Distribution 1.74
    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor 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 Substrate
    CYP 3A4 Inhibitor Non-Inhibitor
    CYP 3A4 Substrate Non-Substrate
    OATP1B1 Non-Inhibitor
    OATP1B3 Non-Inhibitor
    Excretion Clearance 12.88
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs
    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 0.89
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Safe
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Safe
    Maximum Tolerated Dose -0.64
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 4.33
    Micronucleos Safe
    NR-AhR Safe
    NR-AR Safe
    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 -0.17
    Rat (Acute) 1.91
    Rat (Chronic Oral) 1.09
    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 295.01
    Hydration Free Energy -5.01
    Log(D) at pH=7.4 2.76
    Log(P) 3.49
    Log S -2.78
    Log(Vapor Pressure) -3.78
    Melting Point 133.4
    pKa Acid 9.47
    pKa Basic 6.51