MiMeDB: Showing metabocard for (E)-2-epi-beta-caryophyllene (MMDBc0055009)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:39:47 UTC

Update Date

2022-08-12 20:09:11 UTC

Metabolite ID

MMDBc0055009

Metabolite Identification

Common Name

(E)-2-epi-beta-caryophyllene

Description

(E)-2-epi-beta-caryophyllene, also known as isocaryophyllene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on (E)-2-epi-beta-caryophyllene.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221392D          

 18 19  0  0  1  0            999 V2000
    3.3144    1.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4837    0.0072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6581    2.1303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4606    2.9772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3959    1.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6572    1.8253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6928    0.6111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6289    2.9858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8206    2.8207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5050    1.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9319    2.2184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3297    1.3500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3075    2.1747    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4828    2.1525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4245    2.1282    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0971    1.6529    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9389    2.9127    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 11  1  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 12  2  2  0  0  0  0
 12  7  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 13 17  1  1  0  0  0
 14 18  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0055009

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C1=C(C)/CC[C@]2([H])[C@@]([H])(CC2(C)C)C(=C)CC1

> <INCHI_IDENTIFIER>
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

> <INCHI_KEY>
NPNUFJAVOOONJE-QWAJQTJBSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.516536839456762

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4E,9R)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

> <JCHEM_LOGP>
4.519309391666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
67.4524

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,4E,9R)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0       6.187   3.120   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.636   0.013   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.228   3.977   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.726   5.557   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.206   1.946   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.693   3.407   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.893   1.141   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.774   5.573   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.265   5.265   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.809   2.479   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.339   4.141   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.370   1.367   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.349   2.520   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.307   4.059   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.768   4.018   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      10.126   3.973   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       5.781   3.085   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       3.619   5.437   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    6    7                                                       
CONECT    6    5   11   16                                                  
CONECT    7    5   12                                                       
CONECT    8    9   11                                                       
CONECT    9    8   14                                                       
CONECT   10   13   15                                                       
CONECT   11    1    6    8                                                  
CONECT   12    2    7   13                                                  
CONECT   13   10   12   14   17                                             
CONECT   14    9   13   15   18                                             
CONECT   15    3    4   10   14                                             
CONECT   16    6                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

Synonyms

Value	Source
2-Epi-(e)-beta-caryophyllene	ChEBI
9-Epi-(e)-caryophyllene	ChEBI
9-Epi-beta-caryophyllene	ChEBI
9-Epi-caryophyllene	ChEBI
2-Epi-(e)-b-caryophyllene	Generator
2-Epi-(e)-β-caryophyllene	Generator
9-Epi-b-caryophyllene	Generator
9-Epi-β-caryophyllene	Generator
(e)-2-Epi-b-caryophyllene	Generator
(e)-2-Epi-β-caryophyllene	Generator
Caryophyllene, (r,4Z,9S)-(+-)-isomer	MeSH
(e)-beta-Caryophyllene	MeSH
Caryophyllene, (R-(r,4Z,9S))-isomer	MeSH
Caryophyllene, (S-(r,4E,9S))-isomer	MeSH
Caryophyllene, (S-(r,4Z,9S))-isomer	MeSH
Isocaryophyllene	MeSH
trans-Caryophyllene	MeSH
beta-Caryophyllene	MeSH
Caryophyllene	MeSH
Caryophyllene, (R-(r*,4E,9S))-isomer	MeSH

Molecular Formula

C₁₅H₂₄

Average Mass

204.357

Monoisotopic Mass

204.187800773

IUPAC Name

(1R,4E,9R)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

Traditional Name

(1R,4E,9R)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

CAS Registry Number

Not Available

SMILES

[H]\C1=C(C)/CC[C@]2([H])[C@@]([H])(CC2(C)C)C(=C)CC1

InChI Identifier

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

InChI Key

NPNUFJAVOOONJE-QWAJQTJBSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

ortho-fused bicyclic hydrocarbon (CHEBI:68667 )
sesquiterpene (CHEBI:68667 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	4.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.45 m³·mol⁻¹	ChemAxon
Polarizability	25.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4934651

KEGG Compound ID

C20478

BioCyc ID

CPD-14799

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6429274

PDB ID

Not Available

ChEBI ID

68667

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (E)-2-epi-beta-caryophyllene (MMDBc0055009)

MOL for #<Metabolite:0x00007fdb07b25e50>

3D MOL for #<Metabolite:0x00007fdb07b25e50>

3D SDF for #<Metabolite:0x00007fdb07b25e50>

3D-SDF for #<Metabolite:0x00007fdb07b25e50>

PDB for #<Metabolite:0x00007fdb07b25e50>

3D PDB for #<Metabolite:0x00007fdb07b25e50>

SMILES for #<Metabolite:0x00007fdb07b25e50>

INCHI for #<Metabolite:0x00007fdb07b25e50>

Structure for #<Metabolite:0x00007fdb07b25e50>

3D Structure for #<Metabolite:0x00007fdb07b25e50>