NP-MRD: Showing NP-Card for beta-Caryophyllene alcohol (NP0044933)

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Record Information

Version

2.0

Created at

2022-03-10 18:51:22 UTC

Updated at

2022-03-10 22:18:31 UTC

NP-MRD ID

NP0044933

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Caryophyllene alcohol

Description

Beta-Caryophyllene alcohol, also known as caryolan-1-ol or caryophyllenol, belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H). Beta-Caryophyllene alcohol is a neutral compound. Beta-Caryophyllene alcohol is a naturally occurring organic compound derived from Caryophyllene. Beta-Caryophyllene alcohol has an earthy, moss, and spicy odor (http://Www.Thegoodscentscompany.Com/data/rw1014751.Html#toorgano). Beta-Caryophyllene alcohol has been detected in grapefruit juice, black pepper cornmint, and oils from bergamot, hinoki root (2.61%), Hinoki wood (1.49%), Hop and palmarosa ( http://Www.Thegoodscentscompany.Com/data/rw1014751.Html#tooccur). This could make beta-caryophyllene alcohol a potential biomarker for the consumption of these foods. Beta-Caryophyllene alcohol was a tertiary alcohol detected in cannabis (PMID: 6991645 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    3.3430    0.1756   -1.6424 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4999   -0.0339   -0.4296 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1584    0.3530    0.8848 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9571   -1.4760   -0.2797 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8634   -0.8205    0.4475 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0698    0.3365   -0.5387 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5332    1.5495    0.0765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8766    1.7358   -0.4118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8770    0.7999    0.1785 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8239    1.6787    1.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7388    0.1327   -0.8626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5168   -1.3356   -0.9962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0822   -1.7565   -0.8344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5139   -1.3152    0.4525 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5639   -2.3935    1.3711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3487   -0.2237    1.1043 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4837   -0.7252   -2.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9149    0.9888   -2.2584 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3441    0.5474   -1.3078 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1599    0.7763    0.6383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3508   -0.5238    1.5335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5871    1.1216    1.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6507   -2.1236    0.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6873   -1.8470   -1.2916 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1819   -0.4666    1.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6859    0.1586   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6204    1.6131    1.1769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1127    2.4384   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1511    2.8092   -0.3154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8481    1.5465   -1.5248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5169    1.0780    1.6072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1444    2.1992    1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2952    2.4587    0.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8219    0.2903   -0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5381    0.6784   -1.8298 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1687   -1.9449   -0.3406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8148   -1.6203   -2.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5432   -1.4504   -1.7424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0888   -2.8865   -0.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0356   -2.1465    2.1131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2157   -0.6692    1.6562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7507    0.2926    1.9078 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  2  1  0
  2  1  1  6
  2  3  1  0
  2  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
  6  5  1  0
 16  9  1  0
 14  5  1  0
  5 25  1  1
  4 23  1  0
  4 24  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  6 26  1  6
  7 27  1  0
  7 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 13 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END


  Mrv1652307312018372D          

 18 20  0  0  1  0            999 V2000
    4.1538    0.1065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4912    1.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0468    1.7674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2932   -0.3933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1233    1.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1555    0.4202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9216   -0.9278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3500    1.4087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1936   -0.5562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4178    0.2459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5309    0.4040    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3821   -0.4075    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3424    0.2552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5728    1.1318    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7465   -0.9335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0234   -1.7106    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7175    0.2663    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902   -1.2058    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  4  1  0  0  0  0
  8  5  1  0  0  0  0
 11  5  1  0  0  0  0
 12  9  1  0  0  0  0
 12 11  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  1  0  0  0  0
 14  3  1  1  0  0  0
 14  6  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 15 16  1  1  0  0  0
 11 17  1  6  0  0  0
 12 18  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044933

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@]12CC(C)(C)[C@]1([H])CC[C@@]1(C)CCC[C@]2(O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-13(2)9-12-11(13)5-8-14(3)6-4-7-15(12,16)10-14/h11-12,16H,4-10H2,1-3H3/t11-,12+,14-,15+/m1/s1

> <INCHI_KEY>
FUQAYSQLAOJBBC-OSRDXIQISA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
27.38834774171436

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecan-1-ol

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
3.427033741333333

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.18952770320995593

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
66.5019

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecan-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 31-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-JUL-20         0                                  
HETATM    1  C   UNK     0       7.754   0.199   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.517   1.991   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.087   3.299   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.547  -0.734   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.963   2.093   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.290   0.784   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.720  -1.732   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.520   2.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.961  -1.038   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.647   0.459   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.724   0.754   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.447  -0.761   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.239   0.476   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.069   2.113   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.260  -1.743   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.777  -3.193   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       3.206   0.497   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       4.835  -2.251   0.000  0.00  0.00           H+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    6    7                                                       
CONECT    5    8   11                                                       
CONECT    6    4   14                                                       
CONECT    7    4   15                                                       
CONECT    8    5   14                                                       
CONECT    9   12   13                                                       
CONECT   10   14   15                                                       
CONECT   11    5   12   13   17                                             
CONECT   12    9   11   15   18                                             
CONECT   13    1    2    9   11                                             
CONECT   14    3    6    8   10                                             
CONECT   15    7   10   12   16                                             
CONECT   16   15                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

(1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecan-1-ol

Traditional Name

(1S,2S,5R,8R)-4,4,8-trimethyltricyclo[6.3.1.0^{2,5}]dodecan-1-ol

CAS Registry Number

472-97-9

SMILES

[H][C@]12CC(C)(C)[C@]1([H])CC[C@@]1(C)CCC[C@]2(O)C1

InChI Identifier

InChI=1S/C15H26O/c1-13(2)9-12-11(13)5-8-14(3)6-4-7-15(12,16)10-14/h11-12,16H,4-10H2,1-3H3/t11-,12+,14-,15+/m1/s1

InChI Key

FUQAYSQLAOJBBC-OSRDXIQISA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cannabis sativa	NULL	Not Available
Cymbopogon martinii	Plant	KNApSAcK
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rhus coriaria	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Hydrocarbon derivative
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	3.52	ALOGPS
logP	3.43	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-0.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.5 m³·mol⁻¹	ChemAxon
Polarizability	27.39 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for beta-Caryophyllene alcohol (NP0044933)

MOL for NP0044933 (beta-Caryophyllene alcohol)

3D MOL for NP0044933 (beta-Caryophyllene alcohol)

3D SDF for NP0044933 (beta-Caryophyllene alcohol)

3D-SDF for NP0044933 (beta-Caryophyllene alcohol)

PDB for NP0044933 (beta-Caryophyllene alcohol)

3D PDB for NP0044933 (beta-Caryophyllene alcohol)

SMILES for NP0044933 (beta-Caryophyllene alcohol)

INCHI for NP0044933 (beta-Caryophyllene alcohol)

Structure for NP0044933 (beta-Caryophyllene alcohol)

3D Structure for NP0044933 (beta-Caryophyllene alcohol)