NP-MRD: Showing NP-Card for 7-Isopropyl-1,4-dimethylazulene (NP0048560)

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Record Information

Version

2.0

Created at

2022-03-17 20:58:23 UTC

Updated at

2025-02-11 15:44:31 UTC

NP-MRD ID

NP0048560

Natural Product DOI

https://doi.org/10.57994/1241

Secondary Accession Numbers

None

Natural Product Identification

Common Name

7-Isopropyl-1,4-dimethylazulene

Description

7-Isopropyl-1,4-dimethylazulene, also known as 1,4-dimethyl-7-isopropylazulene or guaiazulene, belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Thus, 7-isopropyl-1,4-dimethylazulene is considered to be an isoprenoid lipid molecule. 7-Isopropyl-1,4-dimethylazulene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 7-Isopropyl-1,4-dimethylazulene has been detected, but not quantified in, several different foods, such as fats and oils, figs, german camomiles, and tea. 7-Isopropyl-1,4-dimethylazulene is found in Aristolochia elegans, Artemisia thuscula, Calicogorgia granulosa, Cedrela odorata, Cinnamomum parthenoxylon, Guaiacum officinale , Guaiacum sanctum, Halocarpus kirkii, Juniperus excelsa, Mastigophora diclados, Matricaria chamomilla , Micromeria juliana, Mikania cordifolia, Santolina corsica, Thymus broussonetti, Thymus maroccanus, Thymus praecos and Valeriana officinalis. This could make 7-isopropyl-1,4-dimethylazulene a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061309162D          

 15 16  0  0  0  0            999 V2000
    3.4036    3.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5208    3.0665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2027    0.0699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7017    3.2532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    1.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4717    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5485    1.8011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    1.1337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    2.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7050    3.1894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3863    0.8742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9566    2.4686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1906    2.5444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    1.3886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413    2.2136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  2  0  0  0  0
  8  6  2  0  0  0  0
 10  1  1  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  5  1  0  0  0  0
 12  4  1  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  2  0  0  0  0
 15  9  1  0  0  0  0
 15 12  2  0  0  0  0
 15 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048560

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1=CC2=C(C)C=CC2=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3

> <INCHI_KEY>
FWKQNCXZGNBPFD-UHFFFAOYSA-N

> <FORMULA>
C15H18

> <MOLECULAR_WEIGHT>
198.3034

> <EXACT_MASS>
198.140850576

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.033583274767327

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4-dimethyl-7-(propan-2-yl)azulene

> <ALOGPS_LOGP>
4.99

> <JCHEM_LOGP>
5.234574501999999

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
66.78140000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.40e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
azulon

> <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       6.353   7.387   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.439   5.724   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.112   0.130   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.310   6.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.956   1.975   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.881   3.362   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.624   3.362   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.786   2.116   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.454   5.092   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.916   5.954   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.454   1.632   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.786   4.608   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.956   4.750   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.250   2.592   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.250   4.132   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    7   11                                                       
CONECT    6    8   12                                                       
CONECT    7    5   13                                                       
CONECT    8    6   14                                                       
CONECT    9   13   15                                                       
CONECT   10    1    2   13                                                  
CONECT   11    3    5   14                                                  
CONECT   12    4    6   15                                                  
CONECT   13    7    9   10                                                  
CONECT   14    8   11   15                                                  
CONECT   15    9   12   14                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
1,4-Dimethyl-7-(1-methylethyl)azulene	ChEBI
1,4-Dimethyl-7-isopropylazulene	ChEBI
3,8-Dimethyl-5-(2-propyl)azulene	ChEBI
Guaiazulene	Kegg
Azunol	Kegg
1, 4-Dimethyl-7-isopropylazulene	HMDB
1,3,5,7,9-Guaiapentaene	HMDB
1,4-Dimethyl-7-(1-methyl)-azulene (azulon)	HMDB
1,4-Dimethyl-7-(1-methylethyl)-azulene	HMDB
1,4-Dimethyl-7-(1-methylethyl)azulene, 9ci	HMDB
1,4-Dimethyl-7-(propan-2-yl)azulene	HMDB
1,4-Dimethyl-7-isopropyl-azulene	HMDB
7-Isopropyl- 1,4-dimethylazulene	HMDB
7-Isopropyl-1,4-dimethyl-azulene	HMDB
AZ-8 beris	HMDB
Azulen-beris	HMDB
Azulene, 7-isopropyl-1,4-dimethyl- (8ci)	HMDB
Azulol	HMDB
Azulon	HMDB
Cuteazul	HMDB
Eucazulen	HMDB
Eucazulene	HMDB
Guajazulene	HMDB
Guiazulene	HMDB
Gurjunazulen	HMDB
Hepatoprotectant	HMDB
Kessazulen	HMDB
Kessazulene	HMDB
Purazulen	HMDB
S-Guaiazulene	HMDB
Silazulon	HMDB
Uroazulen	HMDB
Vaumigan	HMDB
Vetivazulen	HMDB
7-Isopropyl-1,4-dimethylazulene	ChEBI

Chemical Formula

C₁₅H₁₈

Average Mass

198.3034 Da

Monoisotopic Mass

198.14085 Da

IUPAC Name

1,4-dimethyl-7-(propan-2-yl)azulene

Traditional Name

azulon

CAS Registry Number

489-84-9

SMILES

CC(C)C1=CC2=C(C)C=CC2=C(C)C=C1

InChI Identifier

InChI=1S/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3

InChI Key

FWKQNCXZGNBPFD-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-04	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-04	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Aristolochia elegans	LOTUS Database	35616633
Artemisia thuscula	LOTUS Database	35616633
Calicogorgia granulosa	LOTUS Database	35616633
Cedrela odorata	LOTUS Database	35616633
Cinnamomum parthenoxylon	LOTUS Database	35616633
Ficus carica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Guaiacum officinale	Plant	KNApSAcK
Guaiacum sanctum	Plant	KNApSAcK
Halocarpus kirkii	LOTUS Database	35616633
Juniperus excelsa	LOTUS Database	35616633
Mastigophora diclados	LOTUS Database	35616633
Matricaria chamomilla	Plant	KNApSAcK
Matricaria recutita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Micromeria juliana	LOTUS Database	35616633
Mikania cordifolia	LOTUS Database	35616633
Santolina corsica	LOTUS Database	35616633
Thymus broussonetti	Plant	KNApSAcK
Thymus maroccanus	Plant	KNApSAcK
Thymus praecos	Plant	KNApSAcK
Valeriana officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Substituents

Guaiane sesquiterpenoid
Azulene
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

sesquiterpene (CHEBI:5550 )
Guaiane sesquiterpenoids (C09675 )
Eudesmanes (C09675 )
Guaiane sesquiterpenoids (LMPR0103410006 )

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	4.99	ALOGPS
logP	5.23	ChemAxon
logS	-3.2	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	66.78 m³·mol⁻¹	ChemAxon
Polarizability	25.03 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon