NP-MRD: Showing NP-Card for junenol (NP0250246)

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Record Information

Version

2.0

Created at

2022-09-07 13:01:40 UTC

Updated at

2022-09-07 13:01:40 UTC

NP-MRD ID

NP0250246

Secondary Accession Numbers

None

Natural Product Identification

Common Name

junenol

Description

Junenol belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. junenol is found in Acritopappus confertus, Ageratum fastigiatum, Asarum canadense, Baccharis dracunculifolia, Hypericum perforatum, Piper kadsura, Silphium perfoliatum and Solidago canadensis. junenol was first documented in 2010 (PMID: 21299136). Based on a literature review a small amount of articles have been published on Junenol (PMID: 36008872) (PMID: 35910617) (PMID: 28278643) (PMID: 27231873).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -1.5798    2.3828   -1.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8394    1.5253   -0.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784    1.4171    0.3820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0956    0.2984    1.3841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5502   -0.9777    0.8347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2911   -0.7982    0.0178 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6808   -1.0236   -1.4407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2629   -1.8466    0.3742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1128   -1.4903   -0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4971   -0.1419    0.4030 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9441    0.2043    0.1926 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7921   -0.8009    0.9053 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3370    0.2777   -1.2439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5716    0.8612   -0.2893 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9330    2.1654    0.0204 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7978    0.5974    0.2400 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.3679    3.0407   -1.5724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6123    2.4636   -1.7046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9921    1.2705   -0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2983    2.3645    0.9790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5655    0.6312    2.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1452    0.0931    1.7180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3363   -1.5223    0.2565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2890   -1.6421    1.6809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3658   -1.8966   -1.4520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2305   -0.1659   -1.8532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7953   -1.3088   -2.0438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2675   -1.9837    1.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5606   -2.7839   -0.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7963   -2.3010    0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1202   -1.4455   -1.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741   -0.0464    1.4889 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1191    1.1913    0.6676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3814   -1.0617    1.9062 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7865   -0.3080    1.1124 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9971   -1.6942    0.2798 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6773   -0.7312   -1.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1937    0.9933   -1.3691 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5403    0.5805   -1.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5830    0.6438   -1.3611 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2034    2.2085    0.9545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7575    0.7600    1.3525 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 11  1  0
 11 13  1  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  6
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 16  1  0
 16 14  1  0
 14 15  1  0
 14 10  1  0
 16  6  1  0
 12 34  1  0
 12 35  1  0
 12 36  1  0
 11 33  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 10 32  1  1
  9 30  1  0
  9 31  1  0
  8 28  1  0
  8 29  1  0
  7 25  1  0
  7 26  1  0
  7 27  1  0
  5 23  1  0
  5 24  1  0
  4 21  1  0
  4 22  1  0
  3 19  1  0
  3 20  1  0
  1 17  1  0
  1 18  1  0
 16 42  1  1
 14 40  1  6
 15 41  1  0
M  END


  Mrv1652309072215012D          

 16 17  0  0  1  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  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
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16  2  1  1  0  0  0
  6 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0250246

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1CC[C@@]2(C)CCCC(=C)[C@@H]2[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-10(2)12-7-9-15(4)8-5-6-11(3)13(15)14(12)16/h10,12-14,16H,3,5-9H2,1-2,4H3/t12-,13+,14-,15+/m0/s1

> <INCHI_KEY>
MSJJKJCIFIGTJY-LJISPDSOSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
27.462845406821607

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4aR,8aS)-4a-methyl-8-methylidene-2-(propan-2-yl)-decahydronaphthalen-1-ol

> <JCHEM_LOGP>
3.694077806

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.18777520874662368

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
68.1179

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4aR,8aS)-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   16                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   10   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

(1S,2S,4aR,8aS)-4a-methyl-8-methylidene-2-(propan-2-yl)-decahydronaphthalen-1-ol

Traditional Name

(1S,2S,4aR,8aS)-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-ol

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1CC[C@@]2(C)CCCC(=C)[C@@H]2[C@H]1O

InChI Identifier

InChI=1S/C15H26O/c1-10(2)12-7-9-15(4)8-5-6-11(3)13(15)14(12)16/h10,12-14,16H,3,5-9H2,1-2,4H3/t12-,13+,14-,15+/m0/s1

InChI Key

MSJJKJCIFIGTJY-LJISPDSOSA-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
Acritopappus confertus	LOTUS Database	35616633
Ageratum fastigiatum	LOTUS Database	35616633
Asarum canadense	LOTUS Database	35616633
Baccharis dracunculifolia	LOTUS Database	35616633
Hypericum perforatum	LOTUS Database	35616633
Piper kadsura	LOTUS Database	35616633
Silphium perfoliatum	LOTUS Database	35616633
Solidago canadensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	3.69	ChemAxon
pKa (Strongest Basic)	-0.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.12 m³·mol⁻¹	ChemAxon
Polarizability	27.46 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

C00012805

Chemspider ID

4954519

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6452077

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Carneiro LJ, Bastos JK, Veneziani RCS, Santos MFC, Ambrosio SR: A reliable validated high-performance liquid chromatography-photodiode array detection method for quantification of terpenes in Copaifera pubiflora, Copaifera trapezifolia, and Copaifera langsdorffii oleoresins. Nat Prod Res. 2022 Aug 25:1-6. doi: 10.1080/14786419.2022.2116701. [PubMed:36008872 ]
Getahun MN, Ngiela J, Makwatta JO, Ahuya P, Simon TK, Kamau SK, Torto B, Masiga D: Metabolites From Trypanosome-Infected Cattle as Sensitive Biomarkers for Animal Trypanosomosis. Front Microbiol. 2022 Jul 14;13:922760. doi: 10.3389/fmicb.2022.922760. eCollection 2022. [PubMed:35910617 ]
Jani NA, Sirat HM, Ahmad F, Mohamad Ali NA, Jamil M: Chemical profiling and biological properties of Neolitsea kedahense Gamble essential oils. Nat Prod Res. 2017 Dec;31(23):2793-2796. doi: 10.1080/14786419.2017.1294172. Epub 2017 Feb 24. [PubMed:28278643 ]
Gou JB, Li ZQ, Li CF, Chen FF, Lv SY, Zhang YS: Molecular cloning and functional analysis of a 10-epi-junenol synthase from Inula hupehensis. Plant Physiol Biochem. 2016 Sep;106:288-94. doi: 10.1016/j.plaphy.2016.05.023. Epub 2016 May 18. [PubMed:27231873 ]
Judzentiene A, Budiene J, Butkiene R, Kupcinskiene E, Laffont-Schwob I, Masotti V: Caryophyllene oxide-rich essential oils of Lithuanian Artemisia campestris ssp. campestris and their toxicity. Nat Prod Commun. 2010 Dec;5(12):1981-4. [PubMed:21299136 ]
LOTUS database [Link]

Showing NP-Card for junenol (NP0250246)

MOL for NP0250246 (junenol)

3D MOL for NP0250246 (junenol)

3D SDF for NP0250246 (junenol)

3D-SDF for NP0250246 (junenol)

PDB for NP0250246 (junenol)

3D PDB for NP0250246 (junenol)

SMILES for NP0250246 (junenol)

INCHI for NP0250246 (junenol)

Structure for NP0250246 (junenol)

3D Structure for NP0250246 (junenol)