NP-MRD: Showing NP-Card for (5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran (NP0298270)

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Record Information

Version

2.0

Created at

2022-09-10 09:23:24 UTC

Updated at

2022-09-10 09:23:24 UTC

NP-MRD ID

NP0298270

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Curzerene belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. (5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran is found in Commiphora myrrha and Commiphora wightii. (5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran was first documented in 2022 (PMID: 35158383). Based on a literature review a small amount of articles have been published on Curzerene (PMID: 35048517) (PMID: 35893636) (PMID: 35658209) (PMID: 36016561).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 37  0  0  0  0  0  0  0  0999 V2000
   -3.0877   -0.8461    0.6992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4856   -1.0704   -0.4475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -0.8315   -0.5573 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6729   -0.7378   -2.0146 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3027   -2.0647    0.0178 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1063   -1.7607    0.2587 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1056   -2.5831    0.5219 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2244   -1.9419    0.6781 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9955   -0.5928    0.5149 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9593    0.5176    0.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6372   -0.4945    0.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8405    0.7096   -0.0142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6321    0.3503    0.2436 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3878    1.5839    0.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3489    1.7315   -0.8188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0492    2.7696    0.9261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5813   -0.4930    1.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1688   -1.0043    0.8418 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0168   -1.4205   -1.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5320    0.3020   -2.3639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4321   -1.2716   -2.6251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2937   -1.2554   -2.1836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7926   -2.2861    1.0014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3936   -2.9133   -0.6850 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1679   -2.4059    0.8989 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9821    0.1307    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7004    1.3205   -0.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951    0.9788    1.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1143    1.4875    0.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9718    1.1237   -1.0185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6532    0.0803    1.3318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8684    2.6988   -0.8744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6795    0.9766   -1.5150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541    3.4276    0.3380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9791    3.3269    1.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554    2.4578    1.8500 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  0
  3  2  1  6
  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  1
 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


  Mrv1652309102211232D          

 16 17  0  0  1  0            999 V2000
    1.8219   -0.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3522    0.3352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8825    1.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  3  2  1  6  0  0  0
  3  4  1  1  0  0  0
  3  5  1  0  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  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
  6 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0298270

> <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+/m0/s1

> <INCHI_KEY>
HICAMHOOTMOHPA-DZGCQCFKSA-N

> <FORMULA>
C15H20O

> <MOLECULAR_WEIGHT>
216.324

> <EXACT_MASS>
216.151415264

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
25.973626264880522

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
4.241868537

> <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>
68.2708

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0       3.401  -0.554   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.391   0.626   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.381   2.340   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.744   5.553   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5   13                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    6   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12    3   14                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
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

Not Available

Traditional Name

Not Available

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+/m0/s1

InChI Key

HICAMHOOTMOHPA-DZGCQCFKSA-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
Commiphora myrrha	LOTUS Database	35616633
Commiphora wightii	LOTUS Database	35616633

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

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

57257199

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Curzerene

METLIN ID

Not Available

PubChem Compound

12305300

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 ]
Poudel DK, Ojha PK, Rokaya A, Satyal R, Satyal P, Setzer WN: Analysis of Volatile Constituents in Curcuma Species, viz. C. aeruginosa, C. zedoaria, and C. longa, from Nepal. Plants (Basel). 2022 Jul 26;11(15):1932. doi: 10.3390/plants11151932. [PubMed:35893636 ]
Zohmachhuana A, Malsawmdawngliana, Lalnunmawia F, Mathipi V, Lalrinzuali K, Kumar NS: Curcuma aeruginosa Roxb. exhibits cytotoxicity in A-549 and HeLa cells by inducing apoptosis through caspase-dependent pathways. Biomed Pharmacother. 2022 Jun;150:113039. doi: 10.1016/j.biopha.2022.113039. Epub 2022 May 12. [PubMed:35658209 ]
Fei C, Ji D, Tong H, Li Y, Su L, Qin Y, Bian Z, Zhang W, Mao C, Li L, Lu T: Therapeutic mechanism of Curcuma aromatica Salisb. rhizome against coronary heart disease based on integrated network pharmacology, pharmacological evaluation and lipidomics. Front Pharmacol. 2022 Aug 9;13:950749. doi: 10.3389/fphar.2022.950749. eCollection 2022. [PubMed:36016561 ]
LOTUS database [Link]

Showing NP-Card for (5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran (NP0298270)

MOL for NP0298270 ((5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran)

3D MOL for NP0298270 ((5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran)

3D SDF for NP0298270 ((5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran)

3D-SDF for NP0298270 ((5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran)

PDB for NP0298270 ((5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran)

3D PDB for NP0298270 ((5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran)

SMILES for NP0298270 ((5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran)

INCHI for NP0298270 ((5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran)

Structure for NP0298270 ((5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran)

3D Structure for NP0298270 ((5s,6s)-6-ethenyl-3,6-dimethyl-5-(prop-1-en-2-yl)-5,7-dihydro-4h-1-benzofuran)