NP-MRD: Showing NP-Card for (-)-Bornyl acetate (NP0137113)

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Record Information

Version

2.0

Created at

2022-05-30 16:42:04 UTC

Updated at

2022-05-30 16:42:04 UTC

NP-MRD ID

NP0137113

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Bornyl acetate

Description

(-)-Bornyl acetate, also known as fema 2159, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other (-)-Bornyl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa) (-)-Bornyl acetate is a sweet, balsamic, and fresh tasting compound. Outside of the human body,. Isolated from Blumea balsamifera, Jasonia species, Salvia fruticosa, carrot, rosemary, sage and lavender oil.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    4.2407    0.2198    1.0295 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9857   -0.5709    0.8070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767   -1.7672    1.1756 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -0.0290    0.1830 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6793   -0.7573   -0.0378 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3835   -0.6759   -1.5274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7385    0.3217   -1.5956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3072    1.6812   -1.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1173    1.4684    0.4540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4626    0.0307    0.6216 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7817   -0.4162    1.9812 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5683   -0.1583   -0.3926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0031   -1.5712   -0.5438 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7362    0.7263   -0.2013 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0687   -0.4018    0.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1760    1.0841    0.3087 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3251    0.5787    2.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7288   -1.7820    0.3342 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2800   -0.3461   -2.0950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0029   -1.6312   -1.9231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2893    0.3618   -2.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6494    1.9955   -1.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1372    2.3820   -1.2381 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9643    1.6415    0.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6896    2.1659    1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7553   -1.5240    2.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0618   -0.0193    2.6969 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8200   -0.1185    2.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0050   -1.6820   -0.0798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1496   -1.7664   -1.6402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3472   -2.3131   -0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5461    1.6720    0.3134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1536    0.9890   -1.2073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5667    0.2115    0.3370 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 12 14  1  0
 10  5  1  0
 12  7  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  5 18  1  1
  6 19  1  0
  6 20  1  0
  7 21  1  6
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
M  END


  Mrv0541 11261206242D          

 14 15  0  0  0  0            999 V2000
    0.2062   -0.9208    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5082   -0.5083    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5082    0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062    0.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9207    0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9207   -0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2227   -0.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9372   -0.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516   -0.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9372    0.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2062   -1.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4198   -0.1240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2447   -0.1308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4052   -0.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
  1  6  1  0  0  0  0
  2  7  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
  1 11  1  1  0  0  0
  1 12  1  0  0  0  0
  4 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137113

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1CC2CC[C@@]1(C)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9?,10-,12-/m1/s1

> <INCHI_KEY>
KGEKLUUHTZCSIP-GTFYECCDSA-N

> <FORMULA>
C12H20O2

> <MOLECULAR_WEIGHT>
196.286

> <EXACT_MASS>
196.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.60156417334381

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate

> <ALOGPS_LOGP>
3.50

> <JCHEM_LOGP>
2.430583294666666

> <ALOGPS_LOGS>
-3.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0038392074467

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
54.465799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 26-NOV-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-NOV-12         0                                  
HETATM    1  C   UNK     0       0.385  -1.719   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.949  -0.949   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.949   0.591   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.385   1.361   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.719   0.591   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.719  -0.949   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.282  -1.719   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.616  -0.949   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.950  -1.719   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.616   0.591   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.385  -3.259   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.784  -0.231   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.323  -0.244   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.756  -0.219   0.000  0.00  0.00           C+0
CONECT    1    2    6   11   12                                             
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    1                                                            
CONECT   12    1    4   13   14                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
(-)-Bornyl acetic acid	Generator
(1S,2R,4S)-(-)-Bornyl acetate	HMDB
endo-(1S)-1,7,7-Trimethylbicyclo[2.2.1]hept-2-yl acetate	HMDB
FEMA 2159	HMDB
L-alpha-Bornyl acetate	HMDB
L-Born-2-yl acetate	HMDB
L-Bornyl acetate	HMDB
Levo-bornyl acetate	HMDB
(1S,2R)-1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl acetic acid	Generator

Chemical Formula

C₁₂H₂₀O₂

Average Mass

196.2860 Da

Monoisotopic Mass

196.14633 Da

IUPAC Name

(1S,2R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate

Traditional Name

(1S,2R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1CC2CC[C@@]1(C)C2(C)C

InChI Identifier

InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3/t9?,10-,12-/m1/s1

InChI Key

KGEKLUUHTZCSIP-GTFYECCDSA-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 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

Bicyclic monoterpenoid
Bornane 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	3.5	ALOGPS
logP	2.43	ChemAxon
logS	-3.5	ALOGPS
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	2	ChemAxon
Refractivity	54.47 m³·mol⁻¹	ChemAxon
Polarizability	22.6 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

HMDB0040397

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020129

KNApSAcK ID

Not Available

Chemspider ID

6207

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6448

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for (-)-Bornyl acetate (NP0137113)

MOL for NP0137113 ((-)-Bornyl acetate)

3D MOL for NP0137113 ((-)-Bornyl acetate)

3D SDF for NP0137113 ((-)-Bornyl acetate)

3D-SDF for NP0137113 ((-)-Bornyl acetate)

PDB for NP0137113 ((-)-Bornyl acetate)

3D PDB for NP0137113 ((-)-Bornyl acetate)

SMILES for NP0137113 ((-)-Bornyl acetate)

INCHI for NP0137113 ((-)-Bornyl acetate)

Structure for NP0137113 ((-)-Bornyl acetate)

3D Structure for NP0137113 ((-)-Bornyl acetate)