NP-MRD: Showing NP-Card for alpha-Bisabolol oxide B (NP0049052)

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Record Information

Version

2.0

Created at

2022-03-17 21:06:21 UTC

Updated at

2022-03-17 21:06:22 UTC

NP-MRD ID

NP0049052

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Bisabolol oxide B

Description

Alpha-Bisabolol oxide B, also known as α-bisabolol oxide b, belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. Alpha-Bisabolol oxide B is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, alpha-Bisabolol oxide B has been detected, but not quantified in, several different foods, such as fats and oils, german camomiles, herbs and spices, roman camomiles, and tea. alpha-Bisabolol oxide B is found in Chamaemalum nobile, Chamomilla rectita, Chamomilla recutina, Cinnamodendron corticosum, Ganoderma lucidum , Laggera pterodonta, Matricaria chamomilla , Melaleuca leucadendra L. , Saussurea involucrata and Stellaria pallida. This could make alpha-bisabolol oxide b a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310172D          

 17 18  0  0  0  0            999 V2000
    5.0380    2.8876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4475   -2.1692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999   -1.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2778    1.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6790    2.4460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7409    1.4899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1270    1.8329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1889    0.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2424   -0.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4973   -0.0497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4860    2.2745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3819    1.0483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4174   -0.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9324   -1.5018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8299    0.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2650   -1.0169    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1624   -0.0497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  1  1  0  0  0  0
 11  5  2  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14 13  1  0  0  0  0
 15  4  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049052

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CCC(CC1)C1(C)CCC(O1)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O2/c1-11-5-7-12(8-6-11)15(4)10-9-13(17-15)14(2,3)16/h5,12-13,16H,6-10H2,1-4H3

> <INCHI_KEY>
RKBAYVATPNYHLW-UHFFFAOYSA-N

> <FORMULA>
C15H26O2

> <MOLECULAR_WEIGHT>
238.3657

> <EXACT_MASS>
238.193280076

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.853804684098368

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[5-methyl-5-(4-methylcyclohex-3-en-1-yl)oxolan-2-yl]propan-2-ol

> <ALOGPS_LOGP>
3.56

> <JCHEM_LOGP>
2.9332302743333334

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.325328778261419

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0939011923884543

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
71.025

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.35e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[5-methyl-5-(4-methylcyclohex-3-en-1-yl)oxolan-2-yl]propan-2-ol

> <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       9.404   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.702  -4.049   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.853  -3.709   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.252   1.957   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.867   4.566   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.850   2.781   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.837   3.421   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.819   1.637   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.052  -1.557   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.528  -0.093   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.374   4.246   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.313   1.957   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.512  -1.557   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.607  -2.803   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.282   0.812   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.361  -1.898   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.036  -0.093   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    7   11                                                       
CONECT    6    8   11                                                       
CONECT    7    5   12                                                       
CONECT    8    6   12                                                       
CONECT    9   10   13                                                       
CONECT   10    9   15                                                       
CONECT   11    1    5    6                                                  
CONECT   12    7    8   15                                                  
CONECT   13    9   14   17                                                  
CONECT   14    2    3   13   16                                             
CONECT   15    4   10   12   17                                             
CONECT   16   14                                                            
CONECT   17   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
a-Bisabolol oxide b	Generator
Α-bisabolol oxide b	Generator
(-)-alpha-Bisabolol oxide b	HMDB
(-)-Bisabolol oxide b	HMDB
Bisabolol oxide b	HMDB
Bisabolol oxide II	HMDB
Bisabololoxide b	MeSH

Chemical Formula

C₁₅H₂₆O₂

Average Mass

238.3657 Da

Monoisotopic Mass

238.19328 Da

IUPAC Name

2-[5-methyl-5-(4-methylcyclohex-3-en-1-yl)oxolan-2-yl]propan-2-ol

Traditional Name

2-[5-methyl-5-(4-methylcyclohex-3-en-1-yl)oxolan-2-yl]propan-2-ol

CAS Registry Number

26184-88-3

SMILES

CC1=CCC(CC1)C1(C)CCC(O1)C(C)(C)O

InChI Identifier

InChI=1S/C15H26O2/c1-11-5-7-12(8-6-11)15(4)10-9-13(17-15)14(2,3)16/h5,12-13,16H,6-10H2,1-4H3

InChI Key

RKBAYVATPNYHLW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Chamaemalum nobile	-	KNApSAcK
Chamaemelum nobile	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Chamomilla rectita	Plant	KNApSAcK
Chamomilla recutina	Plant	KNApSAcK
Cinnamodendron corticosum	LOTUS Database	35616633
Ganoderma lucidum	Fungi	KNApSAcK
Laggera pterodonta	LOTUS Database	35616633
Matricaria chamomilla	Plant	KNApSAcK
Matricaria recutita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Melaleuca leucadendra L.	Plant	KNApSAcK
Saussurea involucrata	LOTUS Database	35616633
Stellaria pallida	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Tertiary alcohol
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

oxolanes (CHEBI:80720 )

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	3.56	ALOGPS
logP	2.93	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	14.33	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.02 m³·mol⁻¹	ChemAxon
Polarizability	28.85 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