NP-MRD: Showing NP-Card for 4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate (NP0215608)

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Record Information

Version

2.0

Created at

2022-09-05 15:16:56 UTC

Updated at

2022-09-05 15:16:56 UTC

NP-MRD ID

NP0215608

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate

Description

Terpinen-4-ol acetate belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate is found in Achillea abrotanoides, Caesulia axillaris, Chamaecyparis lawsoniana, Curcuma pierreana, Helichrysum italicum, Mesosphaerum suaveolens, Minthostachys andina, Persea americana, Thuja occidentalis and Vitex negundo. Based on a literature review very few articles have been published on terpinen-4-ol acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052217162D          

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M  END

     RDKit          2D

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M  END


  Mrv1652309052217162D          

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    1.9896   -1.9765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4861   -2.5652    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
  2  4  1  0  0  0  0
  4  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
  5 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  0  0  0  0
 17 20  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 12 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 24 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
  8 32  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0215608

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1C2CC(=C(C)C1C1(CC3CC(=C1C)C3(C)C)C1CC3CC(=C1C)C3(C)C)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O2/c1-16-22-11-20(29(22,5)6)12-24(16)32(15-21-13-25(18(32)3)30(21,7)8)27-17(2)23-14-26(31(23,9)10)28(27)34-19(4)33/h20-21,24,26-28H,11-15H2,1-10H3

> <INCHI_KEY>
BRGJFCICCOEPPB-UHFFFAOYSA-N

> <FORMULA>
C32H46O2

> <MOLECULAR_WEIGHT>
462.718

> <EXACT_MASS>
462.349780721

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.30851852679896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate

> <JCHEM_LOGP>
5.939703152

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.004650790710757

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
140.1466

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.074  -6.988   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.356  -5.626   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.183  -5.565   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -1.178  -4.323   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.412  -2.867   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.759  -3.868   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.702  -2.945   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.492  -1.841   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.322  -0.840   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.752  -0.175   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.130  -1.353   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.300  -0.352   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.111   0.627   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.364   2.146   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.825   3.124   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.803   2.129   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.520   1.065   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.331   0.086   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.400  -1.616   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.267   2.584   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.960   2.283   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.178   4.349   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.083  -1.679   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -3.623  -1.664   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.766  -0.454   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.598   1.003   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.058   0.989   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.614   2.596   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.380  -0.323   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.393   1.043   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.428  -1.746   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.211  -3.355   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.714  -3.690   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.774  -4.788   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9    5   12                                                  
CONECT   12   11   13   23   27                                             
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   20                                                  
CONECT   18   17   13   19                                                  
CONECT   19   18                                                            
CONECT   20   17   15   21   22                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   12   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   29                                                  
CONECT   27   26   12   28                                                  
CONECT   28   27                                                            
CONECT   29   26   24   30   31                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32    8    6   33   34                                             
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Value	Source
Terpinen-4-ol acetic acid	Generator

Chemical Formula

C₃₂H₄₆O₂

Average Mass

462.7180 Da

Monoisotopic Mass

462.34978 Da

IUPAC Name

4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate

Traditional Name

4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1C2CC(=C(C)C1C1(CC3CC(=C1C)C3(C)C)C1CC3CC(=C1C)C3(C)C)C2(C)C

InChI Identifier

InChI=1S/C32H46O2/c1-16-22-11-20(29(22,5)6)12-24(16)32(15-21-13-25(18(32)3)30(21,7)8)27-17(2)23-14-26(31(23,9)10)28(27)34-19(4)33/h20-21,24,26-28H,11-15H2,1-10H3

InChI Key

BRGJFCICCOEPPB-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, 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
Achillea abrotanoides	LOTUS Database	35616633
Caesulia axillaris	LOTUS Database	35616633
Chamaecyparis lawsoniana	LOTUS Database	35616633
Curcuma pierreana	LOTUS Database	35616633
Helichrysum italicum	LOTUS Database	35616633
Hyptis suaveolens	LOTUS Database	35616633
Minthostachys andina	LOTUS Database	35616633
Persea americana	LOTUS Database	35616633
Thuja occidentalis	LOTUS Database	35616633
Vitex negundo	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Pinane monoterpenoid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	5.94	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	140.15 m³·mol⁻¹	ChemAxon
Polarizability	55.31 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

68749986

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate (NP0215608)

MOL for NP0215608 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate)

3D MOL for NP0215608 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate)

3D SDF for NP0215608 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate)

3D-SDF for NP0215608 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate)

PDB for NP0215608 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate)

3D PDB for NP0215608 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate)

SMILES for NP0215608 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate)

INCHI for NP0215608 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate)

Structure for NP0215608 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate)

3D Structure for NP0215608 (4,6,6-trimethyl-3-(2,6,6-trimethyl-3-{2,6,6-trimethylbicyclo[3.1.1]hept-1-en-3-yl}bicyclo[3.1.1]hept-1-en-3-yl)bicyclo[3.1.1]hept-4-en-2-yl acetate)