NP-MRD: Showing NP-Card for caryophyllane (NP0261623)

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Record Information

Version

2.0

Created at

2022-09-08 04:06:56 UTC

Updated at

2022-09-08 04:06:56 UTC

NP-MRD ID

NP0261623

Secondary Accession Numbers

None

Natural Product Identification

Common Name

caryophyllane

Description

Caryophyllane, also known as eremophilane or valerane, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. caryophyllane is found in Curcuma longa. caryophyllane was first documented in 2021 (PMID: 34771097). Based on a literature review a small amount of articles have been published on caryophyllane (PMID: 35745837) (PMID: 35458612) (PMID: 35408634) (PMID: 33673039).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 43 44  0  0  0  0  0  0  0  0999 V2000
   -1.0804   -3.0252    0.2073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1291   -1.8253    0.3051 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1810   -2.2992   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2844   -1.5008    0.3616 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4723   -0.2425   -0.4366 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1092    0.9231    0.4765 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4108    1.5491    0.9358 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3721    1.9252   -0.3462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0611    1.7289   -0.5296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7164    0.6164    0.2163 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7392   -0.6922   -0.4979 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2604   -0.7667   -0.3212 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2176    0.7121   -0.0075 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0227    1.1644    1.1566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5972    1.4808   -1.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6396   -3.0187   -0.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4846   -3.9817    0.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7280   -3.0982    1.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0526   -1.5921    1.3750 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1315   -2.0737   -1.3756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3282   -3.3839   -0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793   -2.1380    0.3959 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9675   -1.3107    1.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8608   -0.2173   -1.3595 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361   -0.2050   -0.7519 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5707    0.5844    1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2985    1.0442    0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4907    2.6187    0.6050 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5055    1.5623    2.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8768    1.9507   -1.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6171    2.9391    0.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6012    2.6776   -0.2323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3363    1.5987   -1.6154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4999    0.5442    1.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878   -0.7001   -1.5581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6033   -1.3484    0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7874   -1.0465   -1.2478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6195    0.8925    2.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1580    2.2805    1.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0604    0.7486    1.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2021    1.0002   -2.1830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7161    1.3778   -1.3433 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3919    2.5464   -1.2008 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  1  0
  2 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
 10 11  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  6 26  1  1
  5 24  1  0
  5 25  1  0
  4 22  1  0
  4 23  1  0
  3 20  1  0
  3 21  1  0
  2 19  1  1
  1 16  1  0
  1 17  1  0
  1 18  1  0
 11 35  1  6
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 15 42  1  0
 15 43  1  0
 10 34  1  1
  9 32  1  0
  9 33  1  0
  8 30  1  0
  8 31  1  0
M  END

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      10.617   4.194   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.437   3.204   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.964   1.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.437   0.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.104  -0.460   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.587  -0.193   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.817  -1.526   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.597   0.987   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.057   0.987   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.057   2.527   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.517   2.527   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.057   4.067   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.597   2.527   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.587   3.707   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.104   3.974   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14    2                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
2,6,10,10-Tetramethylbicyclo[7.2.0]undecane	ChEBI
Caryophyllane derivative	MeSH
Caryophyllane derivatives	MeSH
Sesquiterpene, polycyclic	MeSH
Valerane derivative	MeSH
Derivative, valerane	MeSH
Eremophilane derivatives	MeSH
Polycyclic sesquiterpene	MeSH
Sesquiterpenes, polycyclic	MeSH
Derivative, caryophyllane	MeSH
Derivative, eremophilane	MeSH
Derivatives, caryophyllane	MeSH
Derivatives, eremophilane	MeSH
Eremophilane	MeSH
Eremophilane derivative	MeSH
Eremophilanes	MeSH
Polycyclic sesquiterpenes	MeSH
Valerane	MeSH
Valerane derivatives	MeSH
Valeranes	MeSH
Caryophyllanes	MeSH
Derivatives, valerane	MeSH

Chemical Formula

C₁₅H₂₈

Average Mass

208.3890 Da

Monoisotopic Mass

208.21910 Da

IUPAC Name

2,6,10,10-tetramethylbicyclo[7.2.0]undecane

Traditional Name

caryophyllane

CAS Registry Number

Not Available

SMILES

CC1CCCC(C)C2CC(C)(C)C2CC1

InChI Identifier

InChI=1S/C15H28/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h11-14H,5-10H2,1-4H3

InChI Key

SITKOPDZOGHVLY-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Curcuma longa	LOTUS Database	35616633

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
Polycyclic hydrocarbon
Saturated hydrocarbon
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

sesquiterpene (CHEBI:36490 )
terpenoid fundamental parent (CHEBI:36490 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.27	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	66.82 m³·mol⁻¹	ChemAxon
Polarizability	27.59 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00012482

Chemspider ID

154252

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

177131

PDB ID

Not Available

ChEBI ID

36490

Good Scents ID

Not Available

References

General References

Di Giacomo S, Gulli M, Facchinetti R, Minacori M, Mancinelli R, Percaccio E, Scuderi C, Eufemi M, Di Sotto A: Sorafenib Chemosensitization by Caryophyllane Sesquiterpenes in Liver, Biliary, and Pancreatic Cancer Cells: The Role of STAT3/ABC Transporter Axis. Pharmaceutics. 2022 Jun 14;14(6):1264. doi: 10.3390/pharmaceutics14061264. [PubMed:35745837 ]
da Cruz ENS, Peixoto LS, da Costa JS, Mourao RHV, do Nascimento WMO, Maia JGS, Setzer WN, da Silva JK, Figueiredo PLB: Seasonal Variability of a Caryophyllane Chemotype Essential Oil of Eugenia patrisii Vahl Occurring in the Brazilian Amazon. Molecules. 2022 Apr 8;27(8):2417. doi: 10.3390/molecules27082417. [PubMed:35458612 ]
da Costa JS, Andrade WMS, de Figueiredo RO, Santos PVL, Freitas JJDS, Setzer WN, da Silva JKR, Maia JGS, Figueiredo PLB: Chemical Composition and Variability of the Volatile Components of Myrciaria Species Growing in the Amazon Region. Molecules. 2022 Mar 30;27(7):2234. doi: 10.3390/molecules27072234. [PubMed:35408634 ]
Di Giacomo S, Mariano A, Gulli M, Fraschetti C, Vitalone A, Filippi A, Mannina L, Scotto d'Abusco A, Di Sotto A: Role of Caryophyllane Sesquiterpenes in the Entourage Effect of Felina 32 Hemp Inflorescence Phytocomplex in Triple Negative MDA-MB-468 Breast Cancer Cells. Molecules. 2021 Nov 5;26(21):6688. doi: 10.3390/molecules26216688. [PubMed:34771097 ]
Silva RCE, Costa JSD, Figueiredo RO, Setzer WN, Silva JKRD, Maia JGS, Figueiredo PLB: Monoterpenes and Sesquiterpenes of Essential Oils from Psidium Species and Their Biological Properties. Molecules. 2021 Feb 12;26(4):965. doi: 10.3390/molecules26040965. [PubMed:33673039 ]
LOTUS database [Link]

Showing NP-Card for caryophyllane (NP0261623)

MOL for NP0261623 (caryophyllane)

3D MOL for NP0261623 (caryophyllane)

3D SDF for NP0261623 (caryophyllane)

3D-SDF for NP0261623 (caryophyllane)

PDB for NP0261623 (caryophyllane)

3D PDB for NP0261623 (caryophyllane)

SMILES for NP0261623 (caryophyllane)

INCHI for NP0261623 (caryophyllane)

Structure for NP0261623 (caryophyllane)

3D Structure for NP0261623 (caryophyllane)