NP-MRD: Showing NP-Card for (1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene (NP0153254)

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Record Information

Version

2.0

Created at

2022-09-02 09:52:54 UTC

Updated at

2022-09-02 09:52:55 UTC

NP-MRD ID

NP0153254

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene

Description

Patchoulene belongs to the class of organic compounds known as polycyclic hydrocarbons. These are polycyclic organic compounds made up only of carbon and hydrogen atoms. (1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene was first documented in 2022 (PMID: 35883828). Based on a literature review a small amount of articles have been published on Patchoulene (PMID: 35398448) (PMID: 35910745) (PMID: 35546067) (PMID: 35279582).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          2D

 39 41  0  0  0  0  0  0  0  0999 V2000
    2.3907    1.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2760    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0323   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3943   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062   -2.6807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4086   -3.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7789   -4.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7826   -3.1798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1470   -1.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5736   -1.2902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8351   -3.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3342   -3.2733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0439   -4.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5054    2.0074    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3944   -0.1110    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5304    2.2324    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3907   -1.0037    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    2.5838    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5922    2.1163    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5321    0.7762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3442    2.2172    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5010   -3.9528    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0969   -2.1188    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0798   -5.1027    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8761   -5.4925    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9924   -5.1762    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7863   -4.2945    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9961   -2.2982    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0002   -0.8266    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2874    0.1823    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2076   -2.6496    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8333   -3.3256    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9204   -1.8926    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8227   -4.6915    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2527   -6.1917    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5054   -5.0439    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6532   -5.2683    0.0000 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  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 13 15  1  0
  6  2  1  0
 13  8  1  0
 11  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  6
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  1
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  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


  Mrv1652309022211522D          

 15 17  0  0  1  0            999 V2000
    3.5131    2.3019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1676    1.5528    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5706    0.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0105    0.2271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2614    0.5726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3584    1.3919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7784    1.9786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9581    1.8909    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5152    1.1949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7832    0.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5603    0.1377    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6480   -0.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0401    0.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8649    0.9568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7017    1.4319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  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  2  0  0  0  0
  2  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
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
  5 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
  8 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153254

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CCC2=C1C[C@@H]1CC[C@]2(C)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-10-5-6-13-12(10)9-11-7-8-15(13,4)14(11,2)3/h10-11H,5-9H2,1-4H3/t10-,11+,15+/m1/s1

> <INCHI_KEY>
CSKINCSXMLCMAR-ZETOZRRWSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
74.31525511938452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,5R,8S)-1,5,11,11-tetramethyltricyclo[6.2.1.0^{2,6}]undec-2(6)-ene

> <ALOGPS_LOGP>
5.68

> <JCHEM_LOGP>
4.057500361666667

> <ALOGPS_LOGS>
-4.23

> <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

> <ALOGPS_SOLUBILITY>
1.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,8S)-1,5,11,11-tetramethyltricyclo[6.2.1.0^{2,6}]undec-2(6)-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       6.558   4.297   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.913   2.898   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.665   1.555   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.620   0.424   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.221   1.069   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.402   2.598   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.320   3.693   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.788   3.530   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.962   2.231   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.462   0.774   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.913   0.257   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.076  -1.274   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.941   1.753   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.481   1.786   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.176   2.673   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    5   12   13                                             
CONECT   12   11                                                            
CONECT   13   11    8   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

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@H]1CCC2=C1C[C@@H]1CC[C@]2(C)C1(C)C

InChI Identifier

InChI=1S/C15H24/c1-10-5-6-13-12(10)9-11-7-8-15(13,4)14(11,2)3/h10-11H,5-9H2,1-4H3/t10-,11+,15+/m1/s1

InChI Key

CSKINCSXMLCMAR-ZETOZRRWSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as polycyclic hydrocarbons. These are polycyclic organic compounds made up only of carbon and hydrogen atoms.

Kingdom

Organic compounds

Super Class

Hydrocarbons

Class

Polycyclic hydrocarbons

Sub Class

Not Available

Direct Parent

Polycyclic hydrocarbons

Alternative Parents

Substituents

Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
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	5.68	ALOGPS
logS	-4.2	ALOGPS

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00021285

Chemspider ID

30772330

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

91746471

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Minchan-Herrera P, Ybanez-Julca RO, Quispe-Diaz IM, Venegas-Casanova EA, Jara-Aguilar R, Salas F, Zevallos-Escobar L, Yanez O, Pino-Rios R, Calderon PB, Benites J: Valeriana pilosa Roots Essential Oil: Chemical Composition, Antioxidant Activities, and Molecular Docking Studies on Enzymes Involved in Redox Biological Processes. Antioxidants (Basel). 2022 Jul 7;11(7):1337. doi: 10.3390/antiox11071337. [PubMed:35883828 ]
Api AM, Belsito D, Botelho D, Bruze M, Burton GA Jr, Buschmann J, Cancellieri MA, Dagli ML, Date M, Dekant W, Deodhar C, Fryer AD, Jones L, Joshi K, Kumar M, Lapczynski A, Lavelle M, Lee I, Liebler DC, Moustakas H, Na M, Penning TM, Ritacco G, Romine J, Sadekar N, Schultz TW, Selechnik D, Siddiqi F, Sipes IG, Sullivan G, Thakkar Y, Tokura Y: Update to RIFM fragrance ingredient safety assessment, beta-patchoulene, CAS Registry Number 514-51-2. Food Chem Toxicol. 2022 May;163 Suppl 1:112997. doi: 10.1016/j.fct.2022.112997. Epub 2022 Apr 8. [PubMed:35398448 ]
Peng X, Ang S, Zhang Y, Fan F, Wu M, Liang P, Wen Y, Gan L, Zhang K, Li D, Yue J: Chemical Constituents With Antiproliferative Activity From Pogostemon cablin (Blanco) Benth. Front Chem. 2022 Jul 15;10:938851. doi: 10.3389/fchem.2022.938851. eCollection 2022. [PubMed:35910745 ]
Tu H, Wang W, Feng Y, Zhang L, Zhou H, Cheng C, Ji L, Cai Q, Feng Y: beta-Patchoulene represses hypoxia-induced proliferation and epithelial-mesenchymal transition of liver cancer cells. Bioengineered. 2022 May;13(5):11907-11922. doi: 10.1080/21655979.2022.2065945. [PubMed:35546067 ]
Tao T, Ye B, Xu Y, Wang Y, Zhu Y, Tian Y: beta-Patchoulene Preconditioning Protects Mice Against Hepatic Ischemia-Reperfusion Injury by Regulating Nrf2/HO-1 Signaling Pathway. J Surg Res. 2022 Jul;275:161-171. doi: 10.1016/j.jss.2022.02.001. Epub 2022 Mar 10. [PubMed:35279582 ]
LOTUS database [Link]

Showing NP-Card for (1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene (NP0153254)

MOL for NP0153254 ((1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene)

3D MOL for NP0153254 ((1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene)

3D SDF for NP0153254 ((1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene)

3D-SDF for NP0153254 ((1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene)

PDB for NP0153254 ((1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene)

3D PDB for NP0153254 ((1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene)

SMILES for NP0153254 ((1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene)

INCHI for NP0153254 ((1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene)

Structure for NP0153254 ((1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene)

3D Structure for NP0153254 ((1r,5r,8s)-1,5,11,11-tetramethyltricyclo[6.2.1.0²,⁶]undec-2(6)-ene)