NP-MRD: Showing NP-Card for 1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate (NP0142461)

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Record Information

Version

2.0

Created at

2022-09-01 21:00:44 UTC

Updated at

2022-09-01 21:00:44 UTC

NP-MRD ID

NP0142461

Secondary Accession Numbers

None

Natural Product Identification

Common Name

1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate

Description

Bornyl butyrate, also known as fema 3907, 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 butyrate is an extremely weak basic (essentially neutral) compound (based on its pKa). Bornyl butyrate is a herbal and woody tasting compound. 1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate is found in Aloysia triphylla. Outside of the human body,.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    5.8869   -0.3485    0.0998 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5524    0.3654    0.1568 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4296   -0.5667   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1553    0.1552   -0.1481 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1395    1.3698    0.1827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9310   -0.4697   -0.4460 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2237    0.2839   -0.3595 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9643    0.3793   -1.7015 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4209    0.1033   -1.3931 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5752   -1.3818   -1.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7201   -1.6535    0.0067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2914   -0.3154    0.5250 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0209   -0.2409    1.9684 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4774    0.5503    0.0759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7486    0.1786    0.7377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1832    2.0105    0.2158 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2275   -0.3582   -0.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7178   -1.3807    0.4895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6468    0.1561    0.7451 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6078    1.1983   -0.5664 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3326    0.7433    1.1826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5947   -0.8395   -1.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4269   -1.4823    0.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0215    1.3096   -0.0575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709   -0.4908   -2.2976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922    1.3332   -2.2012 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1289    0.5972   -2.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1669   -1.8715   -2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6055   -1.7150   -1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8091   -2.2211   -0.2942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3535   -2.1942    0.7091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9416   -0.0078    2.5291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1941    0.4647    2.1579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6999   -1.2547    2.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5854    0.3763    0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8467   -0.8520    1.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9429    0.8421    1.6020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1063    2.5861    0.4505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7926    2.4163   -0.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4652    2.2250    1.0564 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  1  0
 14 16  1  0
 12  7  1  0
 14  9  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  1
  8 25  1  0
  8 26  1  0
  9 27  1  6
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END


  Mrv0541 05061310192D          

 16 17  0  0  0  0            999 V2000
    5.5112   -1.8035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2526    0.2537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6436    0.3570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3626   -0.1549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7231   -2.0476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1177   -1.4871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6411   -2.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -1.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9362   -1.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3297   -1.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1470   -2.5357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243   -1.1707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  7  1  0  0  0  0
 10  9  1  0  0  0  0
 11  9  1  0  0  0  0
 12  6  1  0  0  0  0
 13  2  1  0  0  0  0
 13  3  1  0  0  0  0
 13 10  1  0  0  0  0
 14  4  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  2  0  0  0  0
 16 11  1  0  0  0  0
 16 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0142461

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)OC1CC2CCC1(C)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O2/c1-5-6-12(15)16-11-9-10-7-8-14(11,4)13(10,2)3/h10-11H,5-9H2,1-4H3

> <INCHI_KEY>
VIPNQHBVIDJXJE-UHFFFAOYSA-N

> <FORMULA>
C14H24O2

> <MOLECULAR_WEIGHT>
224.3392

> <EXACT_MASS>
224.177630012

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.512142826252422

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate

> <ALOGPS_LOGP>
4.35

> <JCHEM_LOGP>
3.575687806666666

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.042658082820992

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
63.69370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.40e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate

> <JCHEM_VEBER_RULE>
1

$$$$

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      10.288  -3.367   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.472   0.474   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.068   0.666   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.544  -0.289   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.816  -3.822   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.686  -2.776   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.252  -3.846   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.934  -2.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.063  -3.808   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.700  -3.117   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.614  -2.641   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.215  -3.232   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.831  -0.250   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.129  -1.772   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.874  -4.733   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.085  -2.185   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   13                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    1    6                                                       
CONECT    6    5   12                                                       
CONECT    7    8   10                                                       
CONECT    8    7   14                                                       
CONECT    9   10   11                                                       
CONECT   10    7    9   13                                                  
CONECT   11    9   14   16                                                  
CONECT   12    6   15   16                                                  
CONECT   13    2    3   10   14                                             
CONECT   14    4    8   11   13                                             
CONECT   15   12                                                            
CONECT   16   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
Bornyl butyric acid	Generator
1,7,7-Trimethylbicyclo[2.2.1]hept-2-yl butyrate	HMDB
Borneol, butyrate	HMDB
Bornyl butanoate	HMDB
Bornyl ester OF N-butanoic acid	HMDB
Butyric acid, 2-bornyl ester	HMDB
Butyric acid, 2-bornyl ester (8ci)	HMDB
endo-Bornyl butyrate	HMDB
FEMA 3907	HMDB
1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl butanoic acid	Generator

Chemical Formula

C₁₄H₂₄O₂

Average Mass

224.3392 Da

Monoisotopic Mass

224.17763 Da

IUPAC Name

1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate

Traditional Name

1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)OC1CC2CCC1(C)C2(C)C

InChI Identifier

InChI=1S/C14H24O2/c1-5-6-12(15)16-11-9-10-7-8-14(11,4)13(10,2)3/h10-11H,5-9H2,1-4H3

InChI Key

VIPNQHBVIDJXJE-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
Aloysia triphylla	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

Bicyclic monoterpenoid
Bornane monoterpenoid
Fatty acid ester
Fatty acyl
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	4.35	ALOGPS
logP	3.58	ChemAxon
logS	-4	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	4	ChemAxon
Refractivity	63.69 m³·mol⁻¹	ChemAxon
Polarizability	26.51 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

HMDB0038246

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017538

KNApSAcK ID

Not Available

Chemspider ID

88370

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

97897

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate (NP0142461)

MOL for NP0142461 (1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate)

3D MOL for NP0142461 (1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate)

3D SDF for NP0142461 (1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate)

3D-SDF for NP0142461 (1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate)

PDB for NP0142461 (1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate)

3D PDB for NP0142461 (1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate)

SMILES for NP0142461 (1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate)

INCHI for NP0142461 (1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate)

Structure for NP0142461 (1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate)

3D Structure for NP0142461 (1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl butanoate)