β-Caryophyllene






Names

    • HY-N1415
    • .BETA.-CARYOPHYLLENE [FHFI]
    • beta-trans-caryophyllene
    • Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R,4E,9S)-
    • 87-44-5
    • BETA-CARYOPHYLLENE [FCC]
    • (beta)-Caryophyllene
    • Tincturoid
    • trans-Caryophyllene
    • NCGC00142620-01
    • cb2 receptor
    • (1R,4E,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
    • (-)-Caryophyllene
    • AI3-36121
    • DTXSID8024739
    • MFCD00075925
    • beta-Caryophyllene 2000 microg/mL in Acetonitrile
    • 11CAR7501
    • (-)-trans-Caryophyllene, analytical standard
    • E-.beta.-caryophyllene
    • g-Caryophyllene
    • clove terpenes
    • 2-Methylene-6,10,10-trimethylbicyclo(7.2.0)undec-5-ene
    • EINECS 201-746-1
    • FEMA No. 2252
    • 8-Methylene-4,11,11-(trimethyl)bicyclo[7.2.0]undec-4-ene
    • b-caryophyllene
    • Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]-
    • NS00079049
    • trans-(1R,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
    • beta-cariofillene
    • (E)-Caryophyllene
    • CARYOPHYLLENE [MI]
    • C09629
    • Bicyclo(7.2.0)undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)-
    • LMPR0103120001
    • beta-Caryophyllen
    • BICYCLO(7.2.0)UNDEC-4-ENE, 4,11,11-TRIMETHYL-8-METHYLENE-, (1R-(1R*,4E,9S*)-
    • Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-
    • |A-Caryophyllene (Standard)
    • 02 - Terpenes
    • (E)-beta-caryophyllene
    • (-)-I(2)-caryophyllene
    • (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
    • beta-caryophillene
    • Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, (E)-(1R,9S)-(-)-
    • Beta-Caryophylene
    • Copaiba
    • W-109317
    • ?-Caryophyllene
    • β-Caryophyllene
    • 4,11,11-Trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene, (1R-(1R*,4E,9S))-
    • clove terpene derivative
    • (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo(7.2.0)undec-4-ene
    • 8-Methylene-4,11,11-(trimethyl)bicyclo(7.2.0)undec-4-ene, (1R,4E,9S)-
    • Bicyclo(7.2.0)undec-4-ene, 4,11,11-trimethyl-8-methylene-, (1R-(1R*,4E,9S*))-
    • Caryophyllene
    • CAROPYLLENE
    • trans-beta-caryophyllene
    • caryophyllene beta natural
    • BDBM50529607
    • DTXCID304739
    • CHEBI:63191
    • (1S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undec-5-ene
    • BHW853AU9H
    • .beta.-Caryophyllen
    • (-)-(E)-Caryophyllene
    • NSC 11906
    • L-Caryophyllene
    • Bicyclo[7.2.0]undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)-
    • trans caryophyllene
    • (E)-beta-caryophylene
    • NSC-11906
    • CHEBI:10357
    • (-)-beta-caryophyllene
    • trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene
    • CAS-87-44-5
    • Q421614
    • E-beta-caryophyllene
    • .beta.-trans-Caryophyllene
    • caryophyllene 917
    • CHEMBL445740
    • (1R,4E,9S)-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene
    • s6058
    • (-)-trans-Caryophyllene, >=98.5% (sum of enantiomers, GC)
    • Caryophyllene hg
    • 1-CARYOPHYLLENE
    • P198906
    • .beta.-Caryophyllene, (-)
    • trans-(1R,9S)-4,11,11-trimethyl-8-methylenebicyclo(7.2.0)undec-4-ene
    • BRD-K26878113-001-01-6
    • GTPL13282
    • cariofileno
    • HY-N1415R
    • Caryophyllene, (E)
    • .beta.-Caryophyllene
    • beta-Caryophyllene, >=80%, FCC, FG
    • .beta.-(E)-Caryophyllene
    • NCGC00255159-01
    • (E)-beta-caryophyllene (BCP)
    • Caryophyllene B
    • trans-.beta.-Caryophyllene
    • BETA-CARYOPHYLLENE
    • CS-0016839
    • 8-Methylene-4,11,11-(trimethyl)bicyclo(7.2.0)undec-4-ene
    • CCRIS 8094
    • E-Caryophyllene
    • (1R,4E,9S)-4,11,11-TRIMETHYL-8-METHYLENEBICYCLO(7.2.0)UNDEC-4-ENE
    • (-)-trans-Caryophyllene
    • (-)-E-Caryophyllene
    • UNII-BHW853AU9H
    • beta-(e)-caryophyllene
    • Tox21_301497
    • 12 - Analysis of terpenes
    • Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R- (1R*,4E,9S*)]-
    • BICYCLO(7.2.0)UNDEC-4-ENE, 4,11,11-TRIMETHYL-8-METHYLENE-, (E)-(1R,9S)-(-)-
    • NSC11906
    • AKOS024283988

Attributes

  • Canonical SMILES

    C/C1=C\CCC([C@@H]2CC(C)(C)[C@H]2CC1)=C

  • InChI

    InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m0/s1

  • Molecule Class: Terpenoids
  • TPSA: 0.0
  • #RotBonds: 0
  • MW: 204.35699999999997
  • HBD: 0
  • HBA: 0
  • logP: 4.7252000000000045
  • Chemical Formula: C15H24


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) -4.45
    Human Oral Bioavailability 20% Bioavailable
    Human Intestinal Absorption Absorbed
    Madin-Darby Canine Kidney -4.12
    Human Oral Bioavailability 50% Bioavailable
    P-Glycoprotein Inhibitor Non-Inhibitor
    P-Glycoprotein Substrate Non-Substrate
    Skin Permeability -2.91

    Distribution Blood-Brain Barrier (Central Nervous System) -2.57
    Blood-Brain Barrier Penetrable
    Fraction Unbound (Human) 0.85
    Plasma Protein Binding 52.17
    Steady State Volume of Distribution 2.33

    Metabolism Breast Cancer Resistance Protein Non-Inhibitor
    CYP 1A2 Inhibitor Inhibitor
    CYP 1A2 substrate Substrate
    CYP 2C19 Inhibitor Inhibitor
    CYP 2C19 substrate Non-Substrate
    CYP 2C9 Inhibitor Inhibitor
    CYP 2C9 Substrate 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 13.27
    Organic Cation Transporter 2 Non-Inhibitor
    Half-Life of Drug Half-Life < 3hs

    Toxicity AMES Mutagenesis Safe
    Avian Safe
    Bee Toxic
    Bioconcentration Factor 2.27
    Biodegradation Safe
    Carcinogenesis Toxic
    Crustacean Toxic
    Liver Injury I Safe
    Eye Corrosion Safe
    Eye irritation Toxic
    Maximum Tolerated Dose -0.42
    Liver Injury II Toxic
    hERG Blockers Safe
    Daphnia Maga 5.01
    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 3.28
    Rat (Acute) 1.51
    Rat (Chronic Oral) 1.52
    Fathead Minnow 4.26
    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 259.87
    Hydration Free Energy 0.2
    Log(D) at pH=7.4 3.6
    Log(P) 6.15
    Log S -5.62
    Log(Vapor Pressure) -1.41
    Melting Point 25.29
    pKa Acid 12.68
    pKa Basic 8.66