NP-MRD: Showing NP-Card for {1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid (NP0162277)

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Record Information

Version

2.0

Created at

2022-09-02 20:37:57 UTC

Updated at

2022-09-02 20:37:57 UTC

NP-MRD ID

NP0162277

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid

Description

Bornyl acetic acid belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. {1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid is found in Artemisia salsoloides, Elsholtzia blanda, Mentha longifolia, Micromeria croatica, Ocimum kilimandscharicum, Origanum vulgare, Plectranthus glabratus, Satureja cuneifolia, Tanacetum parthenium, Thymus broussonetii, Thymus citriodorus, Thymus longicaulis and Vitex agnus-castus. {1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid was first documented in 2004 (PMID: 15524301). Based on a literature review a small amount of articles have been published on bornyl acetic acid (PMID: 31877880) (PMID: 29668908) (PMID: 16496683).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
   -2.4949    0.0622    0.6387 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3275    0.2437   -0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4601    1.4806   -1.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1458   -1.0077   -1.1612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8688   -2.0327   -0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3440   -1.2632    1.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0239    0.0712    0.4314 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3153    1.1336    1.3975 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9960   -0.2551   -0.6157 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0976    0.6526   -0.9411 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9804    0.8698    0.2197 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1966    1.9808    0.7729 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6715   -0.2079    0.8123 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1380   -0.6152   -1.8478 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291   -1.0025    0.7028 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687    0.5884    0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3977    0.5263    1.6271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0639    2.2111   -0.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0898    1.2584   -1.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5594    1.9621   -1.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9772   -1.1963   -1.8036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0313   -2.6733   -0.4884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7219   -2.6715    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1570   -1.1000    1.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5552   -1.7277    1.5452 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1345    0.8210    2.0497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5847    1.2930    2.0332 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5010    2.0771    0.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4916   -1.2630   -0.3892 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130    1.6453   -1.3391 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7232    0.1968   -1.7504 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1793   -0.8724    0.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0189    0.2479   -2.5066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5855   -1.4334   -2.4320 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 11 12  2  0
  9 14  1  0
  7  2  1  0
 14  4  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  6
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  1
 10 30  1  0
 10 31  1  0
 13 32  1  0
 14 33  1  0
 14 34  1  0
M  END


  Mrv1652309022222372D          

 14 15  0  0  0  0            999 V2000
    0.2085   -0.1075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9988    0.1293    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2085    0.3661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050    0.9543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906    0.5418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4906   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2050   -1.5207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6340   -0.6957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3484   -0.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3484    0.5418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0629   -0.6957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9195    0.5418    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
  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
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  0  0  0  0
  4 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0162277

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C2CCC1(C)C(CC(O)=O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H20O2/c1-11(2)8-4-5-12(11,3)9(6-8)7-10(13)14/h8-9H,4-7H2,1-3H3,(H,13,14)

> <INCHI_KEY>
CRCRWSPYNRCZFN-UHFFFAOYSA-N

> <FORMULA>
C12H20O2

> <MOLECULAR_WEIGHT>
196.29

> <EXACT_MASS>
196.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
22.322518046679548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-{1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid

> <ALOGPS_LOGP>
3.88

> <JCHEM_LOGP>
2.6316149476666664

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.95391542935764

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
54.613800000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid

> <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       0.389  -0.201   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.864   0.241   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.389   0.683   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.249   1.781   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.916   1.011   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.916  -0.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.249  -1.299   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.249  -2.839   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.583  -0.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.917  -1.299   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.250  -0.529   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.250   1.011   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       7.584  -1.299   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       3.583   1.011   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    7                                             
CONECT    3    2                                                            
CONECT    4    2    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9    4                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
Bornyl acetate	Generator

Chemical Formula

C₁₂H₂₀O₂

Average Mass

196.2900 Da

Monoisotopic Mass

196.14633 Da

IUPAC Name

2-{1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid

Traditional Name

{1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid

CAS Registry Number

Not Available

SMILES

CC1(C)C2CCC1(C)C(CC(O)=O)C2

InChI Identifier

InChI=1S/C12H20O2/c1-11(2)8-4-5-12(11,3)9(6-8)7-10(13)14/h8-9H,4-7H2,1-3H3,(H,13,14)

InChI Key

CRCRWSPYNRCZFN-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
Artemisia salsoloides	LOTUS Database	35616633
Elsholtzia blanda	LOTUS Database	35616633
Mentha longifolia	LOTUS Database	35616633
Micromeria croatica	LOTUS Database	35616633
Ocimum kilimandscharicum	LOTUS Database	35616633
Origanum vulgare	LOTUS Database	35616633
Plectranthus glabratus	LOTUS Database	35616633
Satureja cuneifolia	LOTUS Database	35616633
Tanacetum parthenium	LOTUS Database	35616633
Thymus broussonetii	LOTUS Database	35616633
Thymus citriodorus	LOTUS Database	35616633
Thymus longicaulis	LOTUS Database	35616633
Vitex agnus-castus	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
Monocarboxylic acid or derivatives
Carboxylic acid
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	3.88	ALOGPS
logP	2.63	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	54.61 m³·mol⁻¹	ChemAxon
Polarizability	22.32 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

Not Available

Chemspider ID

15398383

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bornyl acetate

METLIN ID

Not Available

PubChem Compound

20327362

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Minervini F, Missaoui J, Celano G, Calasso M, Achour L, Saidane D, Gobbetti M, De Angelis M: Use of Autochthonous Lactobacilli to Increase the Safety of Zgougou. Microorganisms. 2019 Dec 22;8(1). pii: microorganisms8010029. doi: 10.3390/microorganisms8010029. [PubMed:31877880 ]
Kirkpatrick DM, Leach HL, Xu P, Dong K, Isaacs R, Gut LJ: Comparative Antennal and Behavioral Responses of Summer and Winter Morph Drosophila suzukii (Diptera: Drosophilidae) to Ecologically Relevant Volatiles. Environ Entomol. 2018 Jun 6;47(3):700-706. doi: 10.1093/ee/nvy046. [PubMed:29668908 ]
Lu HM, Liang YZ, Qian P: [Profile-effect on quality control of Houttuynia cordata injection]. Yao Xue Xue Bao. 2005 Dec;40(12):1147-50. [PubMed:16496683 ]
Wu X, Li X, Xiao F, Zhang Z, Xu Z, Wang H: [Studies on the analgesic and anti-inflammatory effect of bornyl acetate in volatile oil from Amomum villosum]. Zhong Yao Cai. 2004 Jun;27(6):438-9. [PubMed:15524301 ]
LOTUS database [Link]

Showing NP-Card for {1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid (NP0162277)

MOL for NP0162277 ({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid)

3D MOL for NP0162277 ({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid)

3D SDF for NP0162277 ({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid)

3D-SDF for NP0162277 ({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid)

PDB for NP0162277 ({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid)

3D PDB for NP0162277 ({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid)

SMILES for NP0162277 ({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid)

INCHI for NP0162277 ({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid)

Structure for NP0162277 ({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid)

3D Structure for NP0162277 ({1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl}acetic acid)