NP-MRD: Showing NP-Card for alpha-Caryophyllene alcohol (NP0044997)

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Record Information

Version

2.0

Created at

2022-03-10 18:52:28 UTC

Updated at

2022-03-10 22:17:59 UTC

NP-MRD ID

NP0044997

Secondary Accession Numbers

None

Natural Product Identification

Common Name

alpha-Caryophyllene alcohol

Description

Alpha-Caryophyllene alcohol also called alpha-Caryophyllenol is a derivative of alpha-Caryophyllene. It belongs to the class of organic compounds known as sesquiterpenoids. It is formally classified as a polycyclic hydrocarbon although it is biochemically a bicyclic sesquiterpenoid as it is synthesized via multiple isoprene units. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-Caryophyllene alcohol exists as a white, crystalline powder. It is a neutral, hydrophobic molecule that is insoluble in water. Alpha-Caryophyllene is an approved food additive and has a woody, spicy or earthy aroma. It is a naturally occurring substance found in a number of foods or plants including black pepper, allspice and guava fruit. It was first synthesized by E.J. Corey in 1964 ( https://Doi.Org/10.1021/Ja00952a036). Alpha-Caryophyllene alcohol is one of more than 140 terpenoids that are found in cannabis plants (PMID: 6991645 ) And the combination of these terpenoids produces the skunky, fruity odor characteristic of C. Savita.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    2.8485   -0.8794   -0.7622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047    0.2989   -0.0234 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4302    1.1606    0.4652 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2971    1.0664   -0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1469    0.0718   -0.9137 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2838   -0.8072    0.3132 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4106   -0.1706    1.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0328   -0.7467    1.0035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9890   -1.0035    2.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447   -1.7809    0.3295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9687   -1.5967   -1.1614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1775   -0.1714   -1.5870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1918    0.7195   -0.8196 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2377    2.1369   -1.2744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6172    0.6074    0.6478 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1390    1.6317    1.4176 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7070   -1.7839   -0.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2859   -1.0516   -1.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9113   -0.8126   -0.9970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9717    1.5454   -0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0909    2.0014    1.1004 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1239    0.5051    1.0307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0129    1.9618   -0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6754    1.3328   -1.8390 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2907   -0.5432   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302   -1.8248    0.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9149   -0.8919    1.7700 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0215    0.7230    1.6360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0407   -1.0567    2.8790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4854   -0.1267    2.9797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6113   -1.8799    2.7283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9446   -1.7185    0.7609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4513   -2.7745    0.5189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8595   -2.1747   -1.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0963   -2.0642   -1.6729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2090    0.1492   -1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8939   -0.1021   -2.6695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4947    2.8153   -0.4091 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3048    2.5156   -1.6894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1073    2.2536   -1.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7232    0.4833    0.6812 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9193    1.9821    1.9546 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  1
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15 16  1  0
  7  2  1  0
 15  8  1  0
 13  5  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
  4 23  1  0
  4 24  1  0
  5 25  1  6
  6 26  1  6
  7 27  1  0
  7 28  1  0
  9 29  1  0
  9 30  1  0
  9 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
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  6
 16 42  1  0
M  END


  Mrv1652303192001303D          

 16 18  0  0  0  0            999 V2000
    2.9817    0.4942    1.7298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2776    0.1201   -0.6626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5021   -2.5337   -0.8365 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0341    2.3214   -1.1609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1689   -0.2660    0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2525   -1.4398    0.5844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4874    1.0594    0.4523 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4459   -1.0587    0.4866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2461    1.3166    0.1095 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0374   -0.6664    0.7562 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0709    0.8273    0.6044 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2355   -0.1790   -1.2257 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2634    0.2268    0.4567 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9593   -1.2504   -0.2174 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2086    1.0676   -0.3681 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3958   -0.1466   -2.2923 O   0  0  0  0  0  0  0  0  0  0  0  0
  1 13  1  0  0  0  0
  2 13  1  0  0  0  0
 14  3  1  6  0  0  0
 15  4  1  6  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6 14  1  0  0  0  0
  7 15  1  0  0  0  0
 10  8  1  6  0  0  0
  8 13  1  0  0  0  0
 11  9  1  6  0  0  0
  9 13  1  0  0  0  0
 10 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 12 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044997

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(C)C[C@H]2[C@@H](C1)[C@]1(C)CCC[C@@]2(C)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-13(2)8-10-11(9-13)15(4)7-5-6-14(10,3)12(15)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14+,15-

> <INCHI_KEY>
MJYUBUQHKCAJQR-LYOXDTQASA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
27.134744368894847

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,6R,7S,11R)-1,4,4,7-tetramethyltricyclo[5.3.1.0^{2,6}]undecan-11-ol

> <ALOGPS_LOGP>
3.47

> <JCHEM_LOGP>
3.4448620843333337

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.29908490970630897

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
66.1324

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.02e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6R,7S,11R)-1,4,4,7-tetramethyltricyclo[5.3.1.0^{2,6}]undecan-11-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-MAR-20         0                                  
HETATM    1  C   UNK     0       2.982   0.494   1.730  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.278   0.120  -0.663  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.502  -2.534  -0.837  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.034   2.321  -1.161  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.169  -0.266   0.466  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.252  -1.440   0.584  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.487   1.059   0.452  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.446  -1.059   0.487  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.246   1.317   0.110  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.037  -0.666   0.756  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.071   0.827   0.604  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.236  -0.179  -1.226  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.263   0.227   0.457  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.959  -1.250  -0.217  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.209   1.068  -0.368  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.396  -0.147  -2.292  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    6    7                                                       
CONECT    6    5   14                                                       
CONECT    7    5   15                                                       
CONECT    8   10   13                                                       
CONECT    9   11   13                                                       
CONECT   10    8   11   14                                                  
CONECT   11    9   10   15                                                  
CONECT   12   14   15   16                                                  
CONECT   13    1    2    8    9                                             
CONECT   14    3    6   10   12                                             
CONECT   15    4    7   11   12                                             
CONECT   16   12                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

(1R,2S,6R,7S,11R)-1,4,4,7-tetramethyltricyclo[5.3.1.0^{2,6}]undecan-11-ol

Traditional Name

(1R,2S,6R,7S,11R)-1,4,4,7-tetramethyltricyclo[5.3.1.0^{2,6}]undecan-11-ol

CAS Registry Number

4586-22-5

SMILES

CC1(C)C[C@H]2[C@@H](C1)[C@]1(C)CCC[C@@]2(C)[C@@H]1O

InChI Identifier

InChI=1S/C15H26O/c1-13(2)8-10-11(9-13)15(4)7-5-6-14(10,3)12(15)16/h10-12,16H,5-9H2,1-4H3/t10-,11+,12-,14+,15-

InChI Key

MJYUBUQHKCAJQR-LYOXDTQASA-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
Cedrus atlantica	Plant	KNApSAcK
Litsea monopetala	Plant	KNApSAcK
Pimenta dioica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic alcohols and derivatives. These are organic compounds containing an aliphatic ring substituted with at least one hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Cyclic alcohols and derivatives

Alternative Parents

Substituents

Cyclic alcohol
Secondary 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	3.47	ALOGPS
logP	3.44	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	-0.3	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	66.13 m³·mol⁻¹	ChemAxon
Polarizability	27.13 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 alpha-Caryophyllene alcohol (NP0044997)

MOL for NP0044997 (alpha-Caryophyllene alcohol)

3D MOL for NP0044997 (alpha-Caryophyllene alcohol)

3D SDF for NP0044997 (alpha-Caryophyllene alcohol)

3D-SDF for NP0044997 (alpha-Caryophyllene alcohol)

PDB for NP0044997 (alpha-Caryophyllene alcohol)

3D PDB for NP0044997 (alpha-Caryophyllene alcohol)

SMILES for NP0044997 (alpha-Caryophyllene alcohol)

INCHI for NP0044997 (alpha-Caryophyllene alcohol)

Structure for NP0044997 (alpha-Caryophyllene alcohol)

3D Structure for NP0044997 (alpha-Caryophyllene alcohol)