NP-MRD: Showing NP-Card for Bourbonene (NP0046815)

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Record Information

Version

2.0

Created at

2022-03-17 20:29:58 UTC

Updated at

2022-03-17 20:29:58 UTC

NP-MRD ID

NP0046815

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bourbonene

Description

Bourbonene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, bourbonene is considered to be an isoprenoid lipid molecule. Bourbonene is found in Achillea abrotanoides, Agastache rugosa, Ageratum conyzoides, Ajuga chamaepitys, Aloysia citrodora, Aloysia triphylla, Ambrosia trifida, Anthemis aciphylla, Anthemis aciphylla BOISS.var.discoidea BOISS, Aristolochia elegans, Artemisia arborescens, Aster scaber, Austrobaileya scandens, Austromyrtus dulcis, Bellis perennis, Betonica macrantha, Boswellia sacra, Bouchardatia neurococca, Bupleurum gibraltaricum, Calamintha nepeta subsp. glandulosa , Cantinoa mutabilis, Chromolaena odorata, Cistus albidus, Cistus creticus, Cleistopholis patens, Clinopodium serpyllifolium, Clinopodium suaveolens, Commiphora gurreh, Commiphora holtziana, Commiphora kataf, Commiphora myrrha, Cryptomeria japonica, Cyclotrichium niveum, Daphne papyracea, Daucus carota, Dendropanax trifidus, Eremanthus arboreus, Erigeron philadelphicus, Acca sellowiana, Geranium bourbon, Guatteriopsis blepharophylla, Hedyosmum costaricense, Heracleum dissectum, Mesosphaerum suaveolens, Hyssopus officinalis, Lallemantia peltata, Lavandula angustifolia , Lavandula canarien-sis, Lavandula dentata , Leonotis leonurus, Lepidozia vitrea, Liquidambar styraciflua, Lonicera japonica, Marrubium parviflorum, Melissa officinalis, Mentha arvensis L. , Mentha piperita, Mentha piperita L. , Mentha verticillata, Micromeria cristata, Micromeria maderensis, Micromeria myrtifolia, Micromeria sinaica, Morina persica, Mosla cavaleriei, Nepeta nuda, Nepeta racemosa, Ocimum basilicum, Ocimum gratissimum , Origanum adanense, Origanum laevigatum, Origanum vulgare , Pelargonium citronellum, Pelargonium endlicherianum, Pelargonium vitifolium, Perilla frutescens, Peucedanum paniculatum L., Phagnalon sordidum, Phyla dulcis, Pinus halepensis , Pinus mugo subsp. Mugo , Pinus sylvestris , Piper arboreum , Piper auritum, Piper fimbriulatum, Piper marginatum, Platostoma africanum, Pycnanthemum floridanum, Quercus coccifera , Renealmia floribunda, Rhanterium epapposum, Salvia absconditiflora, Salvia caespitosa, Salvia cuspidata, Salvia officinalis, Rosmarinus officinalis , Salvia sclarea, Salvia vermifolia, Satureja spicigera, Senecio vulgaris , Sideritis athoa, Sideritis chamaedryfolia, Sideritis montana, Sideritis tragoriganum, Solanum stuckertii, Solanum tuberosum, Solidago canadensis, Stachys aegyptiaca, Stachys recta, Stevia rebaudiana, Tessaria fastigiata, Teucrium asiaticum, Teucrium kotschyanum, Teucrium montanum, Teucrium polium, Thymus broussonetti, Thymus citriodorus, Thymus longicaulis, Thymus maroccanus, Thymus praecos, Thymus vulgaris , Thymus zygioides, Toona ciliata, Turnera diffusa , Uvaria chamae, Vitex agnus-castus and Vitex negundo. Bourbonene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007302D          

 18 20  0  0  0  0            999 V2000
    3.2301   -0.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8711   -0.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4809   -0.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7109    1.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2259    1.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6531    1.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682    1.9178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -0.2017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2259    0.5829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1682    0.5829    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3836    2.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3836    1.6629    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3836    0.8379    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3836    0.0128    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586    2.4879    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586    1.6629    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5586    0.8379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5586    0.0128    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  2  0  0  0  0
  9  4  1  0  0  0  0
 10  6  1  0  0  0  0
 12 11  1  1  0  0  0
 13 10  1  0  0  0  0
 12  7  1  0  0  0  0
 12 13  1  0  0  0  0
 16  5  1  0  0  0  0
 12 16  1  0  0  0  0
 17  9  1  0  0  0  0
 13 17  1  0  0  0  0
 17 16  1  0  0  0  0
 13 14  1  1  0  0  0
 17 18  1  6  0  0  0
 16 15  1  6  0  0  0
 10  8  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0046815

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CCC(=C)[C@]1([H])[C@@]1([H])[C@@H](CC[C@@]21C)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)13(12)14(11)15/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12+,13-,14+,15-/m0/s1

> <INCHI_KEY>
YIRAHEODBQONHI-ZQNQSHIBSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.842163815465245

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,6S,7R,8S)-1-methyl-5-methylidene-8-(propan-2-yl)tricyclo[5.3.0.0^{2,6}]decane

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
4.1460638329999995

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
64.69539999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,6S,7R,8S)-8-isopropyl-1-methyl-5-methylidenetricyclo[5.3.0.0^{2,6}]decane

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0       6.030  -0.696   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.493  -1.521   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.898  -0.377   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.327   2.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.422   3.580   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.952   2.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.047   3.580   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.523  -0.377   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.422   1.088   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.047   1.088   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.583   4.644   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.583   3.104   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.583   1.564   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       2.583   0.024   0.000  0.00  0.00           H+0
HETATM   15  H   UNK     0       1.043   4.644   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       1.043   3.104   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.043   1.564   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       1.043   0.024   0.000  0.00  0.00           H+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4    5    9                                                       
CONECT    5    4   16                                                       
CONECT    6    7   10                                                       
CONECT    7    6   12                                                       
CONECT    8    1    2   10                                                  
CONECT    9    3    4   17                                                  
CONECT   10    6   13    8                                                  
CONECT   11   12                                                            
CONECT   12   11    7   13   16                                             
CONECT   13   10   12   17   14                                             
CONECT   14   13                                                            
CONECT   15   16                                                            
CONECT   16    5   12   17   15                                             
CONECT   17    9   13   16   18                                             
CONECT   18   17                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Value	Source
(-)-beta-Bourbonene	PhytoBank
(-)-β-Bourbonene	PhytoBank
beta-Bourbonene	PhytoBank

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(1S,2R,6S,7R,8S)-1-methyl-5-methylidene-8-(propan-2-yl)tricyclo[5.3.0.0^{2,6}]decane

Traditional Name

(1S,2R,6S,7R,8S)-8-isopropyl-1-methyl-5-methylidenetricyclo[5.3.0.0^{2,6}]decane

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(=C)[C@]1([H])[C@@]1([H])[C@@H](CC[C@@]21C)C(C)C

InChI Identifier

InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)13(12)14(11)15/h9,11-14H,3,5-8H2,1-2,4H3/t11-,12+,13-,14+,15-/m0/s1

InChI Key

YIRAHEODBQONHI-ZQNQSHIBSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Achillea abrotanoides	LOTUS Database	35616633
Agastache rugosa	LOTUS Database	35616633
Ageratum conyzoides	LOTUS Database	35616633
Ajuga chamaepitys	LOTUS Database	35616633
Aloysia citrodora	LOTUS Database	35616633
Aloysia triphylla	LOTUS Database	35616633
Ambrosia trifida	Plant	KNApSAcK
Anthemis aciphylla	LOTUS Database	35616633
Anthemis aciphylla BOISS.var.discoidea BOISS	Plant	KNApSAcK
Aristolochia elegans	LOTUS Database	35616633
Artemisia arborescens	LOTUS Database	35616633
Aster scaber	LOTUS Database	35616633
Austrobaileya scandens	LOTUS Database	35616633
Austromyrtus dulcis	LOTUS Database	35616633
Bellis perennis	LOTUS Database	35616633
Betonica macrantha	LOTUS Database	35616633
Boswellia sacra	LOTUS Database	35616633
Bouchardatia neurococca	LOTUS Database	35616633
Bupleurum gibraltaricum	LOTUS Database	35616633
Calamintha nepeta subsp. glandulosa	Plant	KNApSAcK
Cantinoa mutabilis	LOTUS Database	35616633
Chromolaena odorata	LOTUS Database	35616633
Cistus albidus	Plant	KNApSAcK
Cistus creticus	LOTUS Database	35616633
Cleistopholis patens	LOTUS Database	35616633
Clinopodium serpyllifolium	LOTUS Database	35616633
Clinopodium suaveolens	LOTUS Database	35616633
Commiphora gurreh	LOTUS Database	35616633
Commiphora holtziana	Plant	KNApSAcK
Commiphora kataf	LOTUS Database	35616633
Commiphora myrrha	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Cyclotrichium niveum	LOTUS Database	35616633
Daphne papyracea	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Dendropanax trifidus	LOTUS Database	35616633
Eremanthus arboreus	LOTUS Database	35616633
Erigeron philadelphicus	LOTUS Database	35616633
Feijoa sellowiana	Plant	KNApSAcK
Geranium bourbon	Plant	KNApSAcK
Guatteriopsis blepharophylla	Plant	KNApSAcK
Hedyosmum costaricense	LOTUS Database	35616633
Heracleum dissectum	LOTUS Database	35616633
Hyptis suaveolens	LOTUS Database	35616633
Hyssopus officinalis L.	LOTUS Database	35616633
Lallemantia peltata	LOTUS Database	35616633
Lavandula angustifolia	Plant	KNApSAcK
Lavandula canarien-sis	Plant	KNApSAcK
Lavandula dentata	Plant	KNApSAcK
Leonotis leonurus	LOTUS Database	35616633
Lepidozia vitrea	Plant	KNApSAcK
Liquidambar styraciflua	LOTUS Database	35616633
Lonicera japonica	LOTUS Database	35616633
Marrubium parviflorum	LOTUS Database	35616633
Melissa officinalis	LOTUS Database	35616633
Mentha aquatica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha arvensis	Plant	KNApSAcK
Mentha piperita	LOTUS Database	35616633
Mentha piperita L.	Plant	KNApSAcK
Mentha verticillata	LOTUS Database	35616633
Micromeria cristata	LOTUS Database	35616633
Micromeria maderensis	LOTUS Database	35616633
Micromeria myrtifolia	LOTUS Database	35616633
Micromeria sinaica	LOTUS Database	35616633
Morina persica	LOTUS Database	35616633
Mosla cavaleriei	LOTUS Database	35616633
Nepeta nuda	LOTUS Database	35616633
Nepeta racemosa	LOTUS Database	35616633
Ocimum basilicum	LOTUS Database	35616633
Ocimum gratissimum	Plant	KNApSAcK
Origanum adanense	LOTUS Database	35616633
Origanum laevigatum	LOTUS Database	35616633
Origanum vulgare	Plant	KNApSAcK
Pelargonium citronellum	LOTUS Database	35616633
Pelargonium endlicherianum	LOTUS Database	35616633
Pelargonium vitifolium	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Peucedanum paniculatum L.	Plant	KNApSAcK
Phagnalon sordidum	Plant	KNApSAcK
Phyla dulcis	LOTUS Database	35616633
Pinus halepensis	Plant	KNApSAcK
Pinus mugo subsp. Mugo	Plant	KNApSAcK
Pinus sylvestris	Plant	KNApSAcK
Piper arboreum	Plant	KNApSAcK
Piper auritum	LOTUS Database	35616633
Piper fimbriulatum	Plant	KNApSAcK
Piper marginatum	LOTUS Database	35616633
Platostoma africanum	LOTUS Database	35616633
Pycnanthemum floridanum	LOTUS Database	35616633
Quercus coccifera	Plant	KNApSAcK
Renealmia floribunda	LOTUS Database	35616633
Rhanterium epapposum	LOTUS Database	35616633
Salvia absconditiflora	LOTUS Database	35616633
Salvia caespitosa	LOTUS Database	35616633
Salvia cuspidata	LOTUS Database	35616633
Salvia officinalis	LOTUS Database	35616633
Salvia rosmarinus	Plant	KNApSAcK
Salvia sclarea	LOTUS Database	35616633
Salvia vermifolia	LOTUS Database	35616633
Satureja spicigera	LOTUS Database	35616633
Senecio vulgaris	Plant	KNApSAcK
Sideritis athoa	LOTUS Database	35616633
Sideritis chamaedrifolia	LOTUS Database	35616633
Sideritis montana	LOTUS Database	35616633
Sideritis tragoriganum	LOTUS Database	35616633
Solanum stuckertii	LOTUS Database	35616633
Solanum tuberosum	LOTUS Database	35616633
Solidago canadensis	LOTUS Database	35616633
Stachys aegyptiaca	LOTUS Database	35616633
Stachys recta	LOTUS Database	35616633
Stevia rebaudiana	LOTUS Database	35616633
Tessaria fastigiata	LOTUS Database	35616633
Teucrium asiaticum	LOTUS Database	35616633
Teucrium kotschyanum	LOTUS Database	35616633
Teucrium montanum	LOTUS Database	35616633
Teucrium polium	LOTUS Database	35616633
Thymus broussonetti	Plant	KNApSAcK
Thymus citriodorus	LOTUS Database	35616633
Thymus longicaulis	LOTUS Database	35616633
Thymus maroccanus	Plant	KNApSAcK
Thymus praecos	Plant	KNApSAcK
Thymus vulgaris	Plant	KNApSAcK
Thymus zygioides	LOTUS Database	35616633
Toona ciliata	LOTUS Database	35616633
Turnera diffusa	Plant	KNApSAcK
Uvaria chamae	LOTUS Database	35616633
Vitex agnus-castus	LOTUS Database	35616633
Vitex negundo	LOTUS Database	35616633
Vitis	FooDB	PHYTOHUB

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Bourbonane sesquiterpenoid
Sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Bourbonane sesquiterpenoids (LMPR0103870001 )

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	3.47	ALOGPS
logP	4.15	ChemAxon
logS	-4.9	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	64.7 m³·mol⁻¹	ChemAxon
Polarizability	25.84 Å³	ChemAxon
Number of Rings	3	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

FDB006026

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

62566

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Bourbonene (NP0046815)

MOL for NP0046815 (Bourbonene)

3D MOL for NP0046815 (Bourbonene)

3D SDF for NP0046815 (Bourbonene)

3D-SDF for NP0046815 (Bourbonene)

PDB for NP0046815 (Bourbonene)

3D PDB for NP0046815 (Bourbonene)

SMILES for NP0046815 (Bourbonene)

INCHI for NP0046815 (Bourbonene)

Structure for NP0046815 (Bourbonene)

3D Structure for NP0046815 (Bourbonene)