beta-Caryophyllene

  • GreenMolBD CID : 74
  • Molecular Formula : C15H24
  • Molecular Weight : 204.357
  • Exact Molecular Mass : 204.188
  • IUPAC Name : (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
  • 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-/m1/s1
  • InChI Key : NPNUFJAVOOONJE-GFUGXAQUSA-N
  • Canonical SMILES : CC1=CCCC(=C)C2CC(C2CC1)(C)C
  • Isomeric SMILES : C/C/1=C\CCC(=C)C2CC(C2CC1)(C)C
  • Cross Reference  Pubchem

1. Classification

1.1. Description

This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

1.2. Taxonomy Tree

1.3. Alternative Parent

Polycyclic hydrocarbons; Branched unsaturated hydrocarbons; Cyclic olefins; Unsaturated aliphatic hydrocarbons;

1.4. Molecular Framework

Aliphatic homopolycyclic compounds

1.5. Substituents

Caryophyllane sesquiterpenoid; Sesquiterpenoid; Branched unsaturated hydrocarbon; Polycyclic hydrocarbon; Cyclic olefin; Unsaturated aliphatic hydrocarbon; Unsaturated hydrocarbon; Olefin; Hydrocarbon; Aliphatic homopolycyclic compound

2. Physical Properties

SlogP TPSA HBD HBA nHA nRB nAA nAB SMR vdw_vol vdw_area Density
4.7252 0 0 0 15 0 0 0 6.6743 340.738 241.092 0.599748

3. Quantum Information

Heat of Formation Dipole Moment Electronegativity Homo Lumo Hardness
-36.86945 0.38 -4.14 -9.2965 1.01627 5.156

4. Compound Reactivity

DLP nRFG nLMR
7 0 5

5. Topkat Properties

WOE Prediction Ames Prediction DTP Prediction Rat Oral LD50 (g/kg body weight) Rat Inhalational LC50 (mg/m3/h) Chronic LOAEL (g/kg body weight) Skin Irritancy Skin Sensitization Ocular Irritancy Aerobic Biodegradability Prediction Fathead Minnow LC50 (g/l) Daphnia EC50 (mg/l)
Carcinogen Non-Mutagen Toxic 0.85618 19918.8 0.0146385 Moderate Weak None Degradable 0.000154858 0.260178

6. Drug-Likeliness Test

Lipinski's rule of five Jorgensen's rule of three Goshe filter Veber filter PAINS1 PAINS2 PAINS3
Yes Yes Yes Yes Yes Yes Yes

7. Synonyms

Name
BETA-CARYOPHYLLENE
Caryophyllene
(-)-beta-caryophyllene
87-44-5
L-Caryophyllene
trans-Caryophyllene
(-)-trans-Caryophyllene
.beta.-Caryophyllen
.beta.-Caryophyllene
(E)-beta-caryophyllene
.beta.-(E)-Caryophyllene
CHEBI:10357
NPNUFJAVOOONJE-GFUGXAQUSA-N
(E)-Caryophyllene
MFCD00075925
ST072181
trans-beta-caryophyllene
UNII-BHW853AU9H
b-caryophyllene
(-)-Caryophyllene
(1S,9R)-6,10,10-trimethyl-2-methylenebicyclo[7.2.0]undec-5-ene
C15H24
(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene
(E)-beta-caryophylene
E-.beta.-caryophyllene
BHW853AU9H
.beta.-Caryophyllene, (-)
NSC11906
Caryophyllene B
(1R,4E,9S)-4,11,11-trimethyl-8-methylene-bicyclo[7.2.0]undec-4-ene
Beta-Caryophylene
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R-(1R*,4E,9S*)]-
Caryophyllene, (E)
AC1NQYK7
(-)-(E)-Caryophyllene
DSSTox_CID_4739
.beta.-trans-Caryophyllene
trans-.beta.-Caryophyllene
DSSTox_RID_77517
DSSTox_GSID_24739
AC1Q2A41
CHEMBL445740
DTXSID8024739
Bicyclo(7.2.0)undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)-
Bicyclo[7.2.0]undec-4-ene, 8-methylene-4,11,11-trimethyl-, (E)-(1R,9S)-(-)-
MolPort-001-793-250
ZINC8234282
Tox21_301497
(1R,4E,9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
AKOS024283988
LMPR0103120001
beta-Caryophyllene, >=80%, FCC, FG
CAS-87-44-5
NCGC00142620-01
NCGC00255159-01
DR000334
OR355343
(-)-trans-Caryophyllene, analytical standard
V0915
C09629
W-109317
(-)-trans-Caryophyllene, >=98.5% (sum of enantiomers, GC)
trans-(1R,9S)-4,11,11-trimethyl-8-methylenebicyclo[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-, (E)-(1R,9S)-(-)-
Bicyclo[7.2.0]undec-4-ene, 4,11,11-trimethyl-8-methylene-, [1R- (1R*,4E,9S*)]-
E-Caryophyllene
beta-E-Caryphyllene
Tincturoid
beta-cariofillene
beta-caryophillene
E-beta-caryophyllene
beta-(e)-caryophyllene
beta-trans-caryophyllene
8007-38-3
HY-N1415
CS-0016839

8. Compound in Different Plants

Compound Name Plant Name Compound in Plant Parts Ref
beta-Caryophyllene
Abelmoschus esculentus (L.) Moench Pod 3
Abelmoschus moschatus (L.) Medic. Seed 5
Ageratum conyzoides L Leaf; Aerial; Seed 1 , 2 , 15 , 16 , 17
Amoora rohituka (Roxb.) Wight & Arn. Leaf; Fruit 1
Anisomeles indica (L.) Kuntze. Leaf 3
Annona reticulata L. Leaf 10
Apium graveolens Seed 3
Corchorus olitorius L. Leaf 10
Coriandrum sativum Linn. Seed 2
Curculigo orchioides Leaf 10
Curcuma amada Rhizome 1 , 15
Curcuma aromatica Salisb. Rhizome; Leaf 4 , 8
Curcuma caesia Roxb. Rhizome 1
Curcuma longa L. Leaf 10
Cyperus rotundus L Tuber 5 , 11 , 6 , 7
Ficus carica L. Leaf 10
Ficus religiosa Leaf 10
Garcinia mangostana Leaf 10
Globba marantina I. Rhizome 1
Helianthus annuus Flower 8
Jasminum sambac L. Flower 6
Juglans regia Leaf 13 , 14 , 17
Kaempferia parviflora Rhizome 5
Lactuca sativa L. Leaf 10
Lantana camara L Leaf; Aerial; Leaf and Flower; Seed 1 , 2 , 3 , 4
Leucas aspera Leaf; Flower; Aerial 1 , 2 , 3
Lippia nodiflora (L.) Pod 2
Litchi chinensis Fruit 10
Lycopersicon lycopersicum Leaf 10
Magnolia grandiflora Flower; Leaf 15 , 16
Mangifera indica Fruit Pulp 6
Mentha arvensis Leaf; Shoot Stem; Shoot Leaf; Stolon Stem; Stolon Leaf 1 , 2 , 3 , 12 , 14 , 18
Michelia champaca Leaf 10
Musa paradisiaca Leaf 10
Olea europea Leaf 2 , 4
Phoenix dactylifera Leaf 10
Phyllanthus embelica Leaf 10
Piper betel Leaf 10
Piper nigrum Leaf 10
Punica granatum Leaf 10
Rauvolfia serpentine Leaf 10
Rheum emodi Leaf 10
Ricinus communis Leaf 15 , 5
Rosa damascena Flower; Petal 4 , 7 , 12 , 15
Ruellia tuberosa Leaf 10
Semicarpus anacardium Leaf 1
Zanthoxylum rhetsa Seed Coat; Seed 3 , 5

9. Targets

ID Target Name Gene Symbol Organism Protein Crystal Complex Activity Values Reference
Potency (nM) Ki (nM) IC50 (nM) Kd (nM) EC50 (nM) kon (M-1-s-1) koff (s-1) Biological Assay DOI Article PMID PubChem AID
57 estrogen receptor 1 ESR1 Homo sapiens 69.1666 743075
115 lysine methyltransferase 2A KMT2A Homo sapiens 39.8107 1766
116 menin 1 MEN1 Homo sapiens 39.8107 1766

10. Chemical Vendors

SID Source Name Source URL Source Detail Registry ID Source Record URL
354264512MedChemexpress MCESource URLSource DetailHY-N1415Source Record URL
316408770abcr GmbHSource URLSource DetailAB139270Source Record URL
124573757TimTecSource URLSource DetailST072181Source Record URL
87565865TCI (Tokyo Chemical Industry)Source URLSource DetailC0796Source Record URL
316962825ParchemSource URLSource Detail13357Source Record URL
162250004Chembase.cnSource URLSource Detail155866Source Record URL
355035883MuseChemSource URLSource DetailR058895Source Record URL
255382631BiosynthSource URLSource DetailW-109317Source Record URL
57647960Sigma-AldrichSource URLSource Detail22075_SIGMASource Record URL
329766500Sigma-AldrichSource URLSource Detail75541_SIALSource Record URL
24900952Sigma-AldrichSource URLSource DetailW225207_ALDRICHSource Record URL
310269412Glentham Life Sciences Ltd.Source URLSource DetailGL4922Source Record URL
254786069Boc SciencesSource URLSource Detail87-44-5Source Record URL
241202854AKos Consulting & SolutionsSource URLSource DetailAKOS024283988Source Record URL
29203925R&D ChemicalsSource URLSource Detail5014Source Record URL
113855250ABI ChemSource URLSource DetailAC1NQYK7Source Record URL
117394432ABI ChemSource URLSource DetailAC1Q2A41Source Record URL
354273069AbaChemSceneSource URLSource DetailCS-0016839Source Record URL
354323290iChemical Technology USA IncSource URLSource DetailEBD2205174Source Record URL
3631174121717 CheMall CorporationSource URLSource DetailBG04219530Source Record URL
3605829221717 CheMall CorporationSource URLSource DetailBG07395763Source Record URL
347757339Alfa ChemistrySource URLSource Detail87-44-5Source Record URL
252347044AHH Chemical co.,ltdSource URLSource DetailMT-48973Source Record URL
88836234MolPortSource URLSource DetailMolPort-001-793-250Source Record URL
342585616Acorn PharmaTech Product ListSource URLSource DetailACN-052268Source Record URL
258476809ZINCSource URLSource DetailZINC8234282Source Record URL
347746247Yuhao ChemicalSource URLSource DetailLQ0208Source Record URL
57358200NovoSeekSource URLSource Detail5281515Source Record URL
310106346Aurora Fine Chemicals LLCSource URLSource DetailA17.878.629Source Record URL
162188183AK Scientific, Inc. (AKSCI)Source URLSource DetailV0915Source Record URL