NP-MRD: Showing NP-Card for Curzerene (NP0058623)

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Record Information

Version

2.0

Created at

2022-04-28 03:57:52 UTC

Updated at

2022-04-28 03:57:52 UTC

NP-MRD ID

NP0058623

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Curzerene

Description

Curzerene belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Curzerene is found in Commiphora myrrha, Curcuma aeruginosa, Curcuma aromatica , Curcuma caesia, Curcuma spp., Curcuma wenyujin , Curcuma xanthorrhiza, Curcuma zedoari, Curcuma zedoaria , Lindera strychnifolia , Lindera strichynifolia and Piper nigrum . Curzerene was first documented in 2021 (PMID: 34531745). Based on a literature review a small amount of articles have been published on Curzerene (PMID: 35158383) (PMID: 35048517) (PMID: 35043299) (PMID: 34923374).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
   -1.9078   -1.7559   -1.4658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2196   -0.8188   -0.5746 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054   -0.3484    0.4413 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0178    0.2473    1.5839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5308   -1.5615    0.9589 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8062   -1.8391    0.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4311   -2.9268    0.1199 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6277   -2.6637   -0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7886   -1.2920   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9431   -0.4827   -0.8181 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229   -0.7729    0.1116 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0887    0.5685    0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3172    0.6513   -0.2061 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7549    2.0544   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0410    2.9934    0.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0762    2.4467   -0.6203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9079   -2.1646   -1.4348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6007   -2.1074   -2.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2166   -0.4031   -0.5964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874   -0.5209    2.3646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0541    0.5290    1.2365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5199    1.1090    2.0272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1595   -2.4937    0.8194 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4183   -1.5168    2.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3997   -3.3651   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7849   -1.1092   -1.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2143    0.1732    0.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6279    0.1861   -1.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6861    1.3297   -0.2149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0651    0.8437    1.4225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2344    0.3558   -1.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9379    2.8249    0.9538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4283    3.9958    0.5749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4653    1.7372   -1.3726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9667    3.4240   -1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7944    2.6721    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 14  1  0
 14 15  2  3
 14 13  1  0
 13 12  1  0
 12 11  1  0
 11  6  2  0
  6  5  1  0
  5  3  1  0
  3  4  1  1
  3  2  1  0
  2  1  2  3
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  3 13  1  0
  9 11  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 15 32  1  0
 15 33  1  0
 13 31  1  6
 12 29  1  0
 12 30  1  0
  5 23  1  0
  5 24  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  2 19  1  0
  1 17  1  0
  1 18  1  0
  8 25  1  0
 10 26  1  0
 10 27  1  0
 10 28  1  0
M  END


  Mrv1652304282205572D          

 16 17  0  0  1  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2534   -0.0288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6408   -0.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8661   -0.6996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0396    1.8646    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  6  9  1  6  0  0  0
  5 10  1  6  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
 13 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0058623

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@H]1CC2=C(C[C@]1(C)C=C)OC=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O/c1-6-15(5)8-14-12(11(4)9-16-14)7-13(15)10(2)3/h6,9,13H,1-2,7-8H2,3-5H3/t13-,15+/m1/s1

> <INCHI_KEY>
HICAMHOOTMOHPA-HIFRSBDPSA-N

> <FORMULA>
C15H20O

> <MOLECULAR_WEIGHT>
216.324

> <EXACT_MASS>
216.151415264

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.638899904467607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5R,6R)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-4,5,6,7-tetrahydro-1-benzofuran

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
4.241868537

> <ALOGPS_LOGS>
-4.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6447066716068446

> <JCHEM_POLAR_SURFACE_AREA>
13.14

> <JCHEM_REFRACTIVITY>
68.27080000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5R,6R)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4H-1-benzofuran

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.206  -0.054   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.929  -1.413   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.483  -1.306   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.465   2.016   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.465  -0.476   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.941   3.481   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   15                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    1    7    9                                             
CONECT    7    6    8                                                       
CONECT    8    7                                                            
CONECT    9    6                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    3   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14    2                                                       
CONECT   16   13                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O

Average Mass

216.3240 Da

Monoisotopic Mass

216.15142 Da

IUPAC Name

(5R,6R)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-4,5,6,7-tetrahydro-1-benzofuran

Traditional Name

(5R,6R)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4H-1-benzofuran

CAS Registry Number

Not Available

SMILES

CC(=C)[C@H]1CC2=C(C[C@]1(C)C=C)OC=C2C

InChI Identifier

InChI=1S/C15H20O/c1-6-15(5)8-14-12(11(4)9-16-14)7-13(15)10(2)3/h6,9,13H,1-2,7-8H2,3-5H3/t13-,15+/m1/s1

InChI Key

HICAMHOOTMOHPA-HIFRSBDPSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Commiphora myrrha	LOTUS Database	35616633
Curcuma aeruginosa	LOTUS Database	35616633
Curcuma aromatica	Plant	KNApSAcK
Curcuma caesia	LOTUS Database	35616633
Curcuma spp.	Plant	KNApSAcK
Curcuma wenyujin	Plant	KNApSAcK
Curcuma xanthorrhiza	LOTUS Database	35616633
Curcuma zedoari	Plant	KNApSAcK
Curcuma zedoaria	Plant	KNApSAcK
Lindera aggregata	Plant	KNApSAcK
Lindera strichynifolia	Plant	KNApSAcK
Piper nigrum L.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

Menthofuran monoterpenoid
Bicyclic monoterpenoid
Aromatic monoterpenoid
Benzofuran
Heteroaromatic compound
Furan
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	4.35	ALOGPS
logP	4.24	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	13.14 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	68.27 m³·mol⁻¹	ChemAxon
Polarizability	25.64 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00012040

Chemspider ID

32741492

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Curzerene

METLIN ID

Not Available

PubChem Compound

12305301

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Dougnon G, Ito M: Molecular Descriptors and QSAR Models for Sedative Activity of Sesquiterpenes Administered to Mice via Inhalation. Planta Med. 2022 Feb 14. doi: 10.1055/a-1770-7581. [PubMed:35158383 ]
Cheng B, Hong X, Wang L, Cao Y, Qin D, Zhou H, Gao D: Curzerene suppresses progression of human glioblastoma through inhibition of glutathione S-transferase A4. CNS Neurosci Ther. 2022 May;28(5):690-702. doi: 10.1111/cns.13800. Epub 2022 Jan 20. [PubMed:35048517 ]
de Castro Oliveira JA, Ferreira LS, Garcia IP, de Lima Santos H, Ferreira GS, Rocha JPM, Nunes SA, de Carvalho AA, Pinto JEBP, Bertolucci SKV: Eugenia uniflora, Melaleuca armillaris, and Schinus molle essential oils to manage larvae of the filarial vector Culex quinquefasciatus (Diptera: Culicidae). Environ Sci Pollut Res Int. 2022 May;29(23):34749-34758. doi: 10.1007/s11356-021-18024-x. Epub 2022 Jan 18. [PubMed:35043299 ]
Notarstefano V, Pisani M, Bramucci M, Quassinti L, Maggi F, Vaccari L, Parlapiano M, Giorgini E, Astolfi P: A vibrational in vitro approach to evaluate the potential of monoolein nanoparticles as isofuranodiene carrier in MDA-MB 231 breast cancer cell line: New insights from Infrared and Raman microspectroscopies. Spectrochim Acta A Mol Biomol Spectrosc. 2022 Mar 15;269:120735. doi: 10.1016/j.saa.2021.120735. Epub 2021 Dec 11. [PubMed:34923374 ]
Gu J, Sun R, Wang Q, Liu F, Tang D, Chang X: Standardized Astragalus Mongholicus Bunge-Curcuma Aromatica Salisb. Extract Efficiently Suppresses Colon Cancer Progression Through Gut Microbiota Modification in CT26-Bearing Mice. Front Pharmacol. 2021 Aug 31;12:714322. doi: 10.3389/fphar.2021.714322. eCollection 2021. [PubMed:34531745 ]

Showing NP-Card for Curzerene (NP0058623)

MOL for NP0058623 (Curzerene)

3D MOL for NP0058623 (Curzerene)

3D SDF for NP0058623 (Curzerene)

3D-SDF for NP0058623 (Curzerene)

PDB for NP0058623 (Curzerene)

3D PDB for NP0058623 (Curzerene)

SMILES for NP0058623 (Curzerene)

INCHI for NP0058623 (Curzerene)

Structure for NP0058623 (Curzerene)

3D Structure for NP0058623 (Curzerene)