NP-MRD: Showing NP-Card for 9-hydroxybisabolol oxide (NP0043724)

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Record Information

Version

1.0

Created at

2021-06-21 01:03:14 UTC

Updated at

2021-06-30 00:19:34 UTC

NP-MRD ID

NP0043724

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-hydroxybisabolol oxide

Provided By

JEOL Database JEOL Logo

Description

(3S,6S)-6-[(1S,4R)-4-hydroxy-4-methylcyclohex-2-en-1-yl]-2,2,6-trimethyloxan-3-ol belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. 9-hydroxybisabolol oxide is found in Matricaria chamomilla. It was first documented in 2013 (Avonto, C., et al.). Based on a literature review very few articles have been published on (3S,6S)-6-[(1S,4R)-4-hydroxy-4-methylcyclohex-2-en-1-yl]-2,2,6-trimethyloxan-3-ol.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306222119242D          

 19 20  0  0  1  0            999 V2000
   -1.0606   -0.4390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -0.8515    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3683   -1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3683   -2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -2.5015    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1842   -3.1335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764   -3.1335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -2.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0606   -1.2640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3461   -0.0265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4663   -0.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1586   -0.1697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6889    0.4623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4067    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9370    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5943    1.3808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8764    2.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1202    1.7933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0640    0.7488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  6  0  0  0
  5  7  1  1  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  2  9  1  0  0  0  0
  2 10  1  1  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 10 19  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0043724

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@](C)(O)C=C1)[C@]1(C)CC[C@H](O)C(C)(C)O1

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O3/c1-13(2)12(16)7-10-15(4,18-13)11-5-8-14(3,17)9-6-11/h5,8,11-12,16-17H,6-7,9-10H2,1-4H3/t11-,12+,14+,15+/m1/s1

> <INCHI_KEY>
FUFCOMVTKVHPIF-DHMWGJHJSA-N

> <FORMULA>
C15H26O3

> <MOLECULAR_WEIGHT>
254.37

> <EXACT_MASS>
254.188194697

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
28.522424937759713

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,6S)-6-[(1S,4R)-4-hydroxy-4-methylcyclohex-2-en-1-yl]-2,2,6-trimethyloxan-3-ol

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
1.7396346039999995

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.17106673740012

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.00557613945264

> <JCHEM_PKA_STRONGEST_BASIC>
-1.411110066176923

> <JCHEM_POLAR_SURFACE_AREA>
49.69

> <JCHEM_REFRACTIVITY>
72.89670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.99e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,6S)-6-[(1S,4R)-4-hydroxy-4-methylcyclohex-2-en-1-yl]-2,2,6-trimethyloxan-3-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  H   UNK     0      -1.980  -0.819   0.000  0.00  0.00           H+0
HETATM    2  C   UNK     0      -0.646  -1.589   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.688  -2.359   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.688  -3.899   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.646  -4.669   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.344  -5.849   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -1.636  -5.849   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.980  -3.899   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.980  -2.359   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.646  -0.049   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.870  -0.317   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.163  -0.317   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.153   0.863   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.626   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.616   3.490   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -1.109   2.577   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.636   4.025   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.224   3.347   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.119   1.398   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    9   10                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9                                                       
CONECT    9    8    2                                                       
CONECT   10    2   11   12   19                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   10                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O₃

Average Mass

254.3700 Da

Monoisotopic Mass

254.18819 Da

IUPAC Name

(3S,6S)-6-[(1S,4R)-4-hydroxy-4-methylcyclohex-2-en-1-yl]-2,2,6-trimethyloxan-3-ol

Traditional Name

(3S,6S)-6-[(1S,4R)-4-hydroxy-4-methylcyclohex-2-en-1-yl]-2,2,6-trimethyloxan-3-ol

CAS Registry Number

Not Available

SMILES

[H]O[C@@]1([H])C([H])([H])C([H])([H])[C@@](OC1(C([H])([H])[H])C([H])([H])[H])(C([H])([H])[H])[C@]1([H])C([H])=C([H])[C@@](O[H])(C([H])([H])[H])C([H])([H])C1([H])[H]

InChI Identifier

InChI=1S/C15H26O3/c1-13(2)12(16)7-10-15(4,18-13)11-5-8-14(3,17)9-6-11/h5,8,11-12,16-17H,6-7,9-10H2,1-4H3/t11-,12+,14+,15+/m1/s1

InChI Key

FUFCOMVTKVHPIF-DHMWGJHJSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Matricaria chamomilla	JEOL database	Avonto, C., et al, J. Nat. Prod. 76, 1848 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Oxanes

Sub Class

Not Available

Direct Parent

Oxanes

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic heteromonocyclic 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	2.17	ALOGPS
logP	1.74	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	14.01	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.69 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	72.9 m³·mol⁻¹	ChemAxon
Polarizability	28.52 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	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

30829894

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

72702446

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Avonto, C., et al. (2013). Avonto, C., et al, J. Nat. Prod. 76, 1848 (2013). J. Nat. Prod..

Showing NP-Card for 9-hydroxybisabolol oxide (NP0043724)

MOL for NP0043724 (9-hydroxybisabolol oxide)

3D MOL for NP0043724 (9-hydroxybisabolol oxide)

3D SDF for NP0043724 (9-hydroxybisabolol oxide)

3D-SDF for NP0043724 (9-hydroxybisabolol oxide)

PDB for NP0043724 (9-hydroxybisabolol oxide)

3D PDB for NP0043724 (9-hydroxybisabolol oxide)

SMILES for NP0043724 (9-hydroxybisabolol oxide)

INCHI for NP0043724 (9-hydroxybisabolol oxide)

Structure for NP0043724 (9-hydroxybisabolol oxide)

3D Structure for NP0043724 (9-hydroxybisabolol oxide)