NP-MRD: Showing NP-Card for Dihydrojasmone (NP0085440)

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Record Information

Version

2.0

Created at

2022-04-29 05:58:02 UTC

Updated at

2022-04-29 05:58:03 UTC

NP-MRD ID

NP0085440

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dihydrojasmone

Description

Dihydrojasmone, also known as fema 3763 or jasmone,dihydro, belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. Dihydrojasmone is an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydrojasmone is an aroma compound with the chemical formula C11H18O. Dihydrojasmone is a fresh, herbal, and jasmin tasting compound. Outside of the human body, Dihydrojasmone has been detected, but not quantified in, citrus. This could make dihydrojasmone a potential biomarker for the consumption of these foods. Dihydrojasmone belongs to the family of ketones. It has a fruity, jasmine odor with woody and herbal undertones. Dihydrojasmone is found in Citrus bergamia . Dihydrojasmone was first documented in 1969 (PMID: 12262299). Perfumery uses include natural green, woody, lavender and bergamot (PMID: 17340535) (PMID: 11701026) (PMID: 874613).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 30  0  0  0  0  0  0  0  0999 V2000
    3.1886    1.1877    0.7390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1026    0.1859    1.1361 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8256   -0.7423   -0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3558   -0.0071   -1.2431 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0946    0.7628   -1.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0795   -0.0352   -0.7207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8031    0.1633    0.3667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6383    1.1784    1.4414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9017   -0.8344    0.3983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5758   -1.8796   -0.6267 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6107   -1.1520   -1.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2755   -1.4009   -2.6807 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9533    0.6923    0.1324 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7221    2.0541    0.2213 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6391    1.5478    1.6824 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5212   -0.3827    1.9947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2021    0.6986    1.4656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7801   -1.2642   -0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0481   -1.4666    0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1630    0.7553   -1.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3371   -0.6425   -2.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1128    1.2882   -2.0450 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2959    1.5844   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2501    0.6984    2.3685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0339    2.0462    1.1279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6698    1.5926    1.6313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9400   -1.2917    1.3970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8884   -0.3957    0.1641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0028   -2.6954   -0.1351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4467   -2.2456   -1.1845 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 11  6  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.255   5.265   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.651   3.903   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.589   6.035   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.923   5.265   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.256   6.035   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.590   5.265   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.361   6.553   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.591   7.887   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.331   5.409   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.924   6.035   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.085   7.567   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.940   8.597   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    9                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5   10                                                       
CONECT    7    8    9                                                       
CONECT    8    7   11                                                       
CONECT    9    2    7   10                                                  
CONECT   10    6    9   11                                                  
CONECT   11    8   10   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol

Synonyms

Value	Source
2-Amyl-3-methyl-2-cyclopenten-1-one	HMDB
2-N-Pentyl-3-methyl-2-cyclopenten-1-one	HMDB
2-Pentyl-3-methyl-2-cyclopenten-1-one	HMDB
3-Methyl-2-(N-pentanyl)-2-cyclopenten-1-one	HMDB
3-Methyl-2-pentyl-2-cyclopenten-1-one	HMDB
3-Methyl-2-pentyl-cyclopent-2-enone	HMDB
3-Methyl-2-pentylcyclopent-2-en-1-one	HMDB
3-Methyl-2-pentylcyclopent-2-enone	HMDB
Dihydro-jasmone	HMDB
FEMA 3763	HMDB
Jasmone,dihydro	HMDB
Tetrahydropyrethrone	HMDB

Chemical Formula

C₁₁H₁₈O

Average Mass

166.2600 Da

Monoisotopic Mass

166.13577 Da

IUPAC Name

3-methyl-2-pentylcyclopent-2-en-1-one

Traditional Name

3-methyl-2-pentylcyclopent-2-en-1-one

CAS Registry Number

Not Available

SMILES

CCCCCC1=C(C)CCC1=O

InChI Identifier

InChI=1S/C11H18O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h3-8H2,1-2H3

InChI Key

YCIXWYOBMVNGTB-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, 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
Citrus bergamia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	3.55	ALOGPS
logP	3.46	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	51.78 m³·mol⁻¹	ChemAxon
Polarizability	20.66 Å³	ChemAxon
Number of Rings	1	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

HMDB0031565

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008180

KNApSAcK ID

Not Available

Chemspider ID

56166

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Dihydrojasmone

METLIN ID

Not Available

PubChem Compound

62378

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Nakashita Y, Hesse M: Conversion of nitroheptane to dihydrojasmone. Planta Med. 1985 Aug;51(4):349-50. doi: 10.1055/s-2007-969513. [PubMed:17340535 ]
Trost BM, Pinkerton AB: A three-component coupling approach to cyclopentanoids. J Org Chem. 2001 Nov 16;66(23):7714-22. doi: 10.1021/jo010593b. [PubMed:11701026 ]
Katsure J, Matsui M: Synthetic studies on cyclopentane derivatives. Pt. 1. Alternative routes to dl-prostaglandin-B1 and dihydrojasmone. Agric Biol Chem. 1969;33(7):1078-86. [PubMed:12262299 ]
Bakuzis P, Bakuzis ML: Synthesis of 2-alkylcyclopentenones. Jasmone, dihydrojasmone, and a prostaglandin precursor. J Org Chem. 1977 Jul 8;42(14):2362-5. doi: 10.1021/jo00434a003. [PubMed:874613 ]

Showing NP-Card for Dihydrojasmone (NP0085440)

MOL for NP0085440 (Dihydrojasmone)

3D MOL for NP0085440 (Dihydrojasmone)

3D SDF for NP0085440 (Dihydrojasmone)

3D-SDF for NP0085440 (Dihydrojasmone)

PDB for NP0085440 (Dihydrojasmone)

3D PDB for NP0085440 (Dihydrojasmone)

SMILES for NP0085440 (Dihydrojasmone)

INCHI for NP0085440 (Dihydrojasmone)

Structure for NP0085440 (Dihydrojasmone)

3D Structure for NP0085440 (Dihydrojasmone)