Caryophyllene oxide






Names

    • BDBM50241720
    • CHEMBL508894
    • 4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.0~4,6~]dodecane
    • Epoxycaryophyllene
    • (1R-(1R*,4R*,6R*,10S*))-4,12,12-Trimethyl-9-methylene-5-oxatricyclo(8.2.0.04,6)dodecane
    • NVEQFIOZRFFVFW-RGCMKSIDSA-N
    • CARYOPHYLLENE 4.BETA.,5.ALPHA.-OXIDE
    • MFCD00134216
    • CARYOPHYLLENE 4.BETA.,5.ALPHA.-EPOXIDE
    • beta-Caryophyllene oxide
    • 5-OXATRICYCLO(8.20.0(4,6))DODECANE, 4,12,12-TRIMETHYL-9-METHYLENE-, (1R,4R,6R,10S)-
    • UNII-S2XU9K448U
    • Caryophyllene oxide
    • W-108611
    • 4,12,12-trimethyl-9-methylene-
    • (-)Carophyllene oxide
    • Caryophyllene oxide (Standard)
    • (1R,4R,6R,10S)- 4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.]dodecane (caryophyllene oxide) 5-Oxatricyclo(8.2.0.0(4,6))dodecane
    • (1R,4R,6R,10S)- 5-Oxatricyclo[8.2.0.0(4,6)-]dodecane
    • (-)-Caryophyllene oxide
    • EINECS 214-519-7
    • SR-05000002236
    • CARYOPHYLLENE, EPOXIDE
    • 5-Oxatricyclo(8.2.0.0(sup 4,6))dodecane, 4,12,12-trimethyl-9-methylene-, (1R,4R,6R,10S)-
    • CARYOPHYLLENE 4beta,5alpha-EPOXIDE
    • CARYOPHYLLENEOXIDE
    • (-)-5-Oxatricyclo[8.2.0.0(4,6)]dodecane,4,12,12-trimethyl-9-methylene-
    • (1R,4R,6R,10S)-4,12,12-Trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane
    • Caryophyllene Oxide 90001
    • 4,12,12-Trimethyl-9-methylene-5-oxatricyclo(8.2.0.04,6)dodecane, (1R,4R,6R,10S)-
    • [1R-(1R*,4R*,6R*,10S*)]-4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane
    • ambar crystal
    • (-)-Caryophyllene oxide, analytical reference material
    • AKOS030241571
    • HY-N3544
    • b-Caryophyllene Epoxide
    • 4beta,5alpha-EPOXYCARYOPHYLLENE
    • (-)-BETA-CARYOPHYLLENE EPOXIDE [HSDB]
    • trans-caryophyllene oxide
    • beta-Caryophyllene epoxide
    • (1R,4R,6R,10S)-4,12,12-TRIMETHYL-9-METHYLIDENE-5-OXATRICYCLO[8.2.0.0?,?]DODECANE
    • (-)-Epoxydihydrocaryophyllene
    • (1R,4R,5R,9S)-4,5-epoxycaryophyllan-8(13)-ene
    • 5-Oxatricyclo(8.2.0.0(4,6))dodecane, 4,12,12-trimethyl-9-methylene-, (1R,4R,6R,10S)-
    • BETA-CARYOPHYLLENE EPOXIDE, (-)-
    • FEMA NO. 4085
    • CARYOPHYLLENE 4beta,5alpha-OXIDE
    • 5-OXATRICYCLO(8.2.0.04,6)DODECANE, 4,12,12-TRIMETHYL-9-METHYLENE-, (1R-(1R*,4R*,6R*,10S*))-
    • HSDB 5466
    • s3983
    • E80731
    • ?-caryophyllene oxide
    • (-)-Caryophyllene oxide, >=99.0% (sum of enantiomers, GC)
    • SR-05000002236-2
    • 5-Oxatricyclo(8.2.0.04,6)dodecane, 4,12,12-trimethyl-9-methylene-, (1R,4R,6R,10S)-
    • SCHEMBL127077
    • (-)-Epoxycaryophyllene
    • S2XU9K448U
    • [1R-(1R*,4R*,6R*,10S*)]- (-)-Epoxydihydrocaryophyllene (-)-<<beta>>-Caryophyllene epoxide (-)-<<beta>>-Caryophyllene oxide 4,11,11-Trimethyl-8-methylene-5-oxatricyclo(8.2.0.0(4,6))dodecane
    • .BETA.-CARYOPHYLLENE OXIDE [FHFI]
    • 4-12,12-TRIMETHYL-9-METHYLENE-5-OXATRICYLO (8.2.0.04,6) DODECANE
    • Caryophylene oxide
    • Q27136294
    • (1R,4R,6R,10S)-9-Methylene-4,12,12-trimethyl-5-oxatricyclo[8.2.0.04,6]dodecane
    • bcp oxide
    • CCG-208462
    • DTXSID4051586
    • (-)-Caryophyllene oxide, 95%
    • 4.BETA.,5.ALPHA.-EPOXYCARYOPHYLLENE
    • .beta.-Caryophyllene oxide
    • HY-N3544R
    • trimethyl(methylene)[?]
    • DTXCID8030138
    • AS-58060
    • (1R,4R,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.04,6]dodecane
    • 1139-30-6
    • (-)-.beta.-Caryophyllene epoxide
    • [1R-(1R*,4R*,6R*,10S*)]- Caryophylene oxide Caryophyllene epoxide Caryophyllene oxyde Epoxycaryophyllene [1R-(1R*,4R*,6R*,10S*)]-4,12,12-trimethyl-9-methylene-5-oxatricyclo[8.2.0.04,6]dodecane <<beta>>-Caryophyllene epoxide <<beta>>-Caryophyllene oxide
    • (1R,4R,6R,10S)-9-Methylene-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0(4,6])dodecane
    • CHEBI:67818
    • epoxide
    • Caryophyllene Oxide 1000 microg/mL in Isopropanol
    • (-)-BETA-CARYOPHYLLENE EPOXIDE
    • C16908
    • 4,11,11-Trimethyl-8-methylene-5-oxatricyclo(8.2.0.0(4,6))dodecane
    • CAS-1139-30-6
    • Tox21_303807
    • NCGC00357089-01
    • CS-0023810
    • 5-OXATRICYCLO(8.2.0.0(4,6))DODECANE, 4,12,12-TRIMETHYL-9-METHYLENE-, (1R-(1R*,4R*,6R*,10S*))-

Attributes

  • Canonical SMILES

    C[C@@]12CC[C@@H]3[C@H](CC3(C)C)C(=C)CC[C@H]1O2

  • InChI

    InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13-,15-/m1/s1

  • Molecule Class: Terpenoids
  • TPSA: 12.53
  • #RotBonds: 0
  • MW: 220.35599999999994
  • HBD: 0
  • HBA: 1
  • logP: 3.9364000000000035
  • Chemical Formula: C15H24O


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) -4.94
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.22
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -3.02

    Distribution Blood-Brain Barrier (Central Nervous System) -2.77
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.16
    Plasma Protein Binding 33.55
    Steady State Volume of Distribution 1.48

    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Non-Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor 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 17.5
    Organic Cation Transporter 2 Inhibitor
    Half-Life of Drug Half-Life < 3hs

    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 1.8
    Biodegradation Safe
    Carcinogenesis Safe
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Toxic
    Maximum Tolerated Dose 0.32
    Liver Injury II Safe
    hERG Blockers Safe
    Daphnia Maga 4.77
    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 1.39
    Rat (Acute) 1.41
    Rat (Chronic Oral) 1.23
    Fathead Minnow 3.94
    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 274.99
    Hydration Free Energy -1.68
    Log(D) at pH=7.4 3.84
    Log(P) 4.56
    Log S -4.34
    Log(Vapor Pressure) -1.66
    Melting Point 39.08
    pKa Acid 9.44
    pKa Basic 6.65