NP-MRD: Showing NP-Card for cyperene (NP0328414)

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Record Information

Version

2.0

Created at

2022-09-12 11:52:02 UTC

Updated at

2022-09-12 11:52:02 UTC

NP-MRD ID

NP0328414

Secondary Accession Numbers

None

Natural Product Identification

Common Name

cyperene

Description

Cyperene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, cyperene is considered to be an isoprenoid. cyperene is found in Aframomum melegueta, Anaphalis longifolia, Arctium lappa, Centrapalus pauciflorus, Cleistopholis patens, Commiphora africana, Copaifera langsdorffii, Critonia hebebotrya, Cyperus alopecuroides, Cyperus rotundus, Daniellia oliveri, Dimerostemma brasilianum, Ichthyothere terminalis, Piper auritum, Piper fimbriulatum, Psiadia altissima, Rhaponticum carthamoides, Rolandra fruticosa, Tanacetum longifolium and Xylopia aethiopica. cyperene was first documented in 2021 (PMID: 34402190). Based on a literature review a small amount of articles have been published on Cyperene (PMID: 35956539) (PMID: 34381841) (PMID: 33565887) (PMID: 33372995).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 41  0  0  0  0  0  0  0  0999 V2000
    3.2959   -0.4375   -1.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0862   -0.3367   -0.4672 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8701    0.0775   -0.7558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0031    0.6036   -1.8269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3112    0.9986   -1.1387 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1992   -0.2032   -1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4547   -1.4566   -0.8404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8908   -1.1728    0.5437 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3921   -2.4186    1.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0107   -0.0204    0.4842 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0233    0.0819    1.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1745   -0.7086    0.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8226    1.2317    0.2835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9272    1.3739    1.2722 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0683    2.4463    0.2546 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4982   -1.4759   -1.6327 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1814    0.0343   -0.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339    0.1199   -2.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3803    1.5694   -2.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1314   -0.1247   -2.6265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7691    1.8760   -1.5875 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4549   -0.3248   -2.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468   -0.1246   -0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2079   -2.2791   -0.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6528   -1.7226   -1.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8035   -0.8607    1.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3142   -3.0326    1.4496 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2279   -3.0634    0.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0137   -2.1539    2.1993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3677    1.1445    1.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7160   -0.2961    2.5538 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1460   -1.7752    1.1749 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1119   -0.3118    1.4482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9218    1.0957    0.9162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7178    0.8647    2.2442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9917    2.4699    1.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0943    2.2330   -0.0814 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1119    2.8982    1.2607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4056    3.1807   -0.4279 H   0  0  0  0  0  0  0  0  0  0  0  0
  9  8  1  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  2 12  1  0
 12 11  1  0
 10 11  1  1
 10 13  1  0
 13 14  1  0
 13 15  1  0
 10  8  1  0
 13  5  1  0
 10  3  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
  8 26  1  1
  7 24  1  0
  7 25  1  0
  6 22  1  0
  6 23  1  0
  5 21  1  6
  4 19  1  0
  4 20  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
 12 32  1  0
 12 33  1  0
 11 30  1  0
 11 31  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv1652309122213522D          

 15 17  0  0  1  0            999 V2000
    0.7005    1.1408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2485    0.5241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0731    0.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6811    1.2369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4511    0.8535    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1193    0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9754   -0.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1393   -0.7805    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9672   -1.5873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4528   -0.1959    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7856   -0.7146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706   -0.2870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9843    0.2720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3218   -0.4808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7516   -0.0309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  1  0  0  0
  8 10  1  0  0  0  0
 10  3  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 12  1  0  0  0  0
 10 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0328414

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@H]2CC3=C(C)CC[C@]13C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-10-7-8-15-11(2)5-6-12(9-13(10)15)14(15,3)4/h11-12H,5-9H2,1-4H3/t11-,12-,15+/m1/s1

> <INCHI_KEY>
RTBLDXVIGWSICW-JMSVASOKSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.565017630104045

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,7R,10R)-4,10,11,11-tetramethyltricyclo[5.3.1.0^{1,5}]undec-4-ene

> <JCHEM_LOGP>
4.057500361666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
65.42779999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,7R,10R)-4,10,11,11-tetramethyltricyclo[5.3.1.0^{1,5}]undec-4-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       1.308   2.129   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.330   0.978   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.870   1.129   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.005   2.309   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.442   1.593   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.689   0.568   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.421  -0.999   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.860  -1.457   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.539  -2.963   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.579  -0.366   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.333  -1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.998  -0.536   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.571   0.508   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.201  -0.897   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.003  -0.058   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8    3   11   13                                             
CONECT   11   10   12                                                       
CONECT   12   11    2                                                       
CONECT   13   10    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1R,7R,10R)-4,10,11,11-tetramethyltricyclo[5.3.1.0^{1,5}]undec-4-ene

Traditional Name

(1R,7R,10R)-4,10,11,11-tetramethyltricyclo[5.3.1.0^{1,5}]undec-4-ene

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@H]2CC3=C(C)CC[C@]13C2(C)C

InChI Identifier

InChI=1S/C15H24/c1-10-7-8-15-11(2)5-6-12(9-13(10)15)14(15,3)4/h11-12H,5-9H2,1-4H3/t11-,12-,15+/m1/s1

InChI Key

RTBLDXVIGWSICW-JMSVASOKSA-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
Aframomum melegueta	LOTUS Database	35616633
Anaphalis longifolia	LOTUS Database	35616633
Arctium lappa	LOTUS Database	35616633
Centrapalus pauciflorus	LOTUS Database	35616633
Cleistopholis patens	LOTUS Database	35616633
Commiphora africana	LOTUS Database	35616633
Copaifera langsdorffii	LOTUS Database	35616633
Critonia hebebotrya	LOTUS Database	35616633
Cyperus alopecuroides	LOTUS Database	35616633
Cyperus rotundus	LOTUS Database	35616633
Daniellia oliveri	LOTUS Database	35616633
Dimerostemma brasilianum	LOTUS Database	35616633
Ichthyothere terminalis	LOTUS Database	35616633
Piper auritum	LOTUS Database	35616633
Piper fimbriulatum	LOTUS Database	35616633
Psiadia altissima	LOTUS Database	35616633
Rhaponticum carthamoides	LOTUS Database	35616633
Rolandra fruticosa	LOTUS Database	35616633
Tanacetum longifolium	LOTUS Database	35616633
Xylopia aethiopica	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

Patchoulane 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

Patchoulane sesquiterpenoids (LMPR0103450002 )

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	4.06	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	65.43 m³·mol⁻¹	ChemAxon
Polarizability	25.57 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

C00021283

Chemspider ID

16737046

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12308843

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Todorova V, Ivanova S, Georgieva Y, Nalbantova V, Karcheva-Bahchevanska D, Benbassat N, Savova MS, Georgiev MI, Ivanov K: Chemical Composition and Histochemical Localization of Essential Oil from Wild and Cultivated Rhaponticum carthamoides Roots and Rhizomes. Plants (Basel). 2022 Aug 6;11(15). pii: plants11152061. doi: 10.3390/plants11152061. [PubMed:35956539 ]
Qu HJ, Lin KW, Li XL, Ou HY, Tan YF, Wang M, Wei N: Chemical Constituents and Anti-Gastric Ulcer Activity of Essential Oils of Alpinia officinarum (Zingiberaceae), Cyperus rotundus (Cyperaceae), and Their Herbal Pair. Chem Biodivers. 2021 Oct;18(10):e2100214. doi: 10.1002/cbdv.202100214. Epub 2021 Sep 7. [PubMed:34402190 ]
Ben Hassine D, Kammoun El Euch S, Rahmani R, Ghazouani N, Kane R, Abderrabba M, Bouajila J: Clove Buds Essential Oil: The Impact of Grinding on the Chemical Composition and Its Biological Activities Involved in Consumer's Health Security. Biomed Res Int. 2021 Aug 2;2021:9940591. doi: 10.1155/2021/9940591. eCollection 2021. [PubMed:34381841 ]
Kambire DA, Boti JB, Ouattara ZA, Thierry AY, Barat N, Bighelli A, Tomi F: Chemical composition of root and stem bark essential oils from Ivorian Isolona dewevrei: structural elucidation of a new natural germacrone. Nat Prod Res. 2022 Apr;36(8):2105-2111. doi: 10.1080/14786419.2020.1851219. Epub 2021 Feb 10. [PubMed:33565887 ]
Yu N, Chen Z, Yang J, Li R, Zou W: Integrated transcriptomic and metabolomic analyses reveal regulation of terpene biosynthesis in the stems of Sindora glabra. Tree Physiol. 2021 Jun 7;41(6):1087-1102. doi: 10.1093/treephys/tpaa168. [PubMed:33372995 ]
LOTUS database [Link]

Showing NP-Card for cyperene (NP0328414)

MOL for NP0328414 (cyperene)

3D MOL for NP0328414 (cyperene)

3D SDF for NP0328414 (cyperene)

3D-SDF for NP0328414 (cyperene)

PDB for NP0328414 (cyperene)

3D PDB for NP0328414 (cyperene)

SMILES for NP0328414 (cyperene)

INCHI for NP0328414 (cyperene)

Structure for NP0328414 (cyperene)

3D Structure for NP0328414 (cyperene)