NP-MRD: Showing NP-Card for lsobornyl acetate (NP0045150)

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Record Information

Version

2.0

Created at

2022-03-10 18:58:49 UTC

Updated at

2022-03-10 22:21:35 UTC

NP-MRD ID

NP0045150

Secondary Accession Numbers

None

Natural Product Identification

Common Name

lsobornyl acetate

Description

Isobornyl acetate, also known as pichtosin, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Isobornyl acetate has been detected in the oils of valerian root (PMID: 1438515 ) And in the essential oil of Thyme obtained by steam distillation (https://Doi.Org/10.1016/J.Fitote.2007.11.004). It is also a volatile component of cannabis plant samples (PMID: 26657499 ).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652303192001472D          

 14 15  0  0  0  0            999 V2000
   -3.1152    0.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9294   -1.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3847   -0.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2352    0.8974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7018    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169    0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902    0.4595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2169   -0.6674    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0527   -0.2549    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5678   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5678    0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8777    1.1740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8777   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  2 11  1  0  0  0  0
  3 11  1  0  0  0  0
 12  4  1  6  0  0  0
  5  6  1  0  0  0  0
  9  5  1  6  0  0  0
  6 12  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
  8 13  2  0  0  0  0
  8 14  1  0  0  0  0
  9 11  1  0  0  0  0
 10 12  1  0  0  0  0
 10 14  1  6  0  0  0
 11 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045150

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1C[C@H]2CC[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-JFGNBEQYSA-N

> <FORMULA>
C12H20O2

> <MOLECULAR_WEIGHT>
196.29

> <EXACT_MASS>
196.146329884

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
11.028464538980348

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,4R)-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>
54.46580000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.01e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0      -5.815   0.858   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.735  -2.154   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.585  -0.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.306   1.675   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.310   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.405   1.246   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.060  -1.722   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.275   0.858   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.405  -1.246   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.965  -0.476   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.060  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.060   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.505   2.192   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -3.505  -0.476   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    6    9                                                       
CONECT    6    5   12                                                       
CONECT    7    9   10                                                       
CONECT    8    1   13   14                                                  
CONECT    9    5    7   11                                                  
CONECT   10    7   12   14                                                  
CONECT   11    2    3    9   12                                             
CONECT   12    4    6   10   11                                             
CONECT   13    8                                                            
CONECT   14    8   10                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

View in JSmol

Synonyms

Value	Source
Isobornyl acetic acid	Generator
Pichtosin	MeSH

Chemical Formula

C₁₂H₂₀O₂

Average Mass

196.2900 Da

Monoisotopic Mass

196.14633 Da

IUPAC Name

(1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate

Traditional Name

(1S,2S,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-yl acetate

CAS Registry Number

125-12-2

SMILES

CC(=O)O[C@H]1C[C@H]2CC[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-JFGNBEQYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cannabis sativa	NULL	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	11.03 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

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

247573

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Buchbauer G, Jager W, Jirovetz L, Meyer F, Dietrich H: [Effects of valerian root oil, borneol, isoborneol, bornyl acetate and isobornyl acetate on the motility of laboratory animals (mice) after inhalation]. Pharmazie. 1992 Aug;47(8):620-2. [PubMed:1438515 ]

Showing NP-Card for lsobornyl acetate (NP0045150)

MOL for NP0045150 (lsobornyl acetate)

3D MOL for NP0045150 (lsobornyl acetate)

3D SDF for NP0045150 (lsobornyl acetate)

3D-SDF for NP0045150 (lsobornyl acetate)

PDB for NP0045150 (lsobornyl acetate)

3D PDB for NP0045150 (lsobornyl acetate)

SMILES for NP0045150 (lsobornyl acetate)

INCHI for NP0045150 (lsobornyl acetate)

Structure for NP0045150 (lsobornyl acetate)

3D Structure for NP0045150 (lsobornyl acetate)