NP-MRD: Showing NP-Card for 2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol (NP0246792)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 08:22:30 UTC

Updated at

2022-09-07 08:22:30 UTC

NP-MRD ID

NP0246792

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol

Description

Patchouli alcohol, also known as patchoulol, 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 ). Patchoulol is also used in the synthesis of the chemotherapy drug Taxol. 2. The discrepancy had resulted from an unanticipated skeletal rearrangement that had occurred in the Büchi synthesis when patchoulene was treated with peroxy acid, an operation that by accident generated the correct architecture of the natural product. The (−)-optical isomer is one of the organic compounds responsible for the typical patchouli scent. Patchouli alcohol is an extremely weak basic (essentially neutral) compound (based on its pKa). Patchouli oil is an important material in perfumery. After several years of careful study Büchi and co-workers proposed the structure of patchouli alcohol to correspond to 1, based on degradation studies from his earlier work, verified later by synthesis of material which corresponded to the natural authentic sample of patchouli alcohol. They had undertaken an X-ray analysis of the patchouli alcohol diester of chromic acid, with the objective of determining the Cr-O-C angles. A serendipitous finding by Dunitz and co-workers revealed a contradictory structure. During early structural investigation the presence of a saturated tricyclic tertiary alcohol was established. Patchoulol or patchouli alcohol (C15H26O) is a sesquiterpene alcohol found in patchouli. 1. Instead they proposed together with Büchi the novel structure. Patchouli alcohol was first isolated in 1869 by Gal and its chemical composition later correctly formulated as C15H26O by Montgolfier. 2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol is found in Nardostachys jatamansi, Pogostemon cablin and Valeriana fauriei. Contains embedded [2.2.2]Propellane motif.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 44  0  0  0  0  0  0  0  0999 V2000
    2.9982    0.5268    1.5707 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5496    0.0262    1.4416 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4916   -1.3710    0.9818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8807   -1.6472   -0.3287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1419   -0.6742   -0.8035 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3184   -0.9129   -2.1886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4206   -0.6674   -0.0669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5424   -0.9512   -1.0768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5654   -1.6462    1.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7439    0.7165    0.5026 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8439    1.6393   -0.7065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4771    1.7564   -1.2883 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4938    0.7125   -0.7379 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7147    0.8143   -1.6131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7349    1.0198    0.6937 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6287    1.2450    1.3615 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0599    1.6148    1.5637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4146    0.1065    2.5273 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6418    0.0519    0.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1657    0.0584    2.5072 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0003   -2.0500    1.7420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5526   -1.7668    0.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4773   -2.7042   -0.3475 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835   -1.6890   -1.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4553   -1.8743   -2.3682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2519   -0.6217   -2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6027   -2.0771   -1.1237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5026   -0.5707   -0.7279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2143   -1.1618    1.9888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6743   -1.7918    1.2104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1566   -2.6369    0.8695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6675    0.6449    1.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6150    1.2724   -1.4031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2063    2.6321   -0.3215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5628    1.5146   -2.3872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0496    2.7489   -1.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0681    1.8471   -1.5756 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3639    0.5951   -2.6612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5299    0.1516   -1.3485 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2713    2.0043    0.7445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218    2.3274    1.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6292    0.7875    2.3886 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  6
  5  7  1  0
  7  8  1  0
  7  9  1  0
  7 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
 15  2  1  0
 13  5  1  0
 16 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  1
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  6 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  1
 11 33  1  0
 11 34  1  0
 12 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  6
 16 41  1  0
 16 42  1  0
M  END


  Mrv0541 04121521062D          

 16 18  0  0  0  0            999 V2000
    0.1444   -1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8062   -0.9504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6866   -0.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4080    0.3600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1616   -0.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7534    0.4717    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7311   -1.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8485   -0.2762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3273   -0.5226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3024   -1.0366    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3684   -0.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5705    0.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -0.5902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1966   -0.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6229   -1.3253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5121   -1.6884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  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  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  2 15  1  0  0  0  0
 15 16  1  0  0  0  0
 10 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0246792

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(O)C(C)(C)C3CCC2(C)C1C3

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

> <INCHI_KEY>
GGHMUJBZYLPWFD-UHFFFAOYSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
26.749243402991738

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol

> <ALOGPS_LOGP>
4.19

> <JCHEM_LOGP>
3.5033453626666664

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.2907522675014106

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
66.21849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.30e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       0.270  -2.694   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.505  -1.774   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.282  -0.179   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.628   0.672   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.035  -0.193   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.140   0.880   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.098  -2.040   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.317  -0.515   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.211  -0.975   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.164  -1.935   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.288  -0.251   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.798   0.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.644  -1.102   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.234  -0.483   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.029  -2.474   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.689  -3.152   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   13                                             
CONECT    6    5                                                            
CONECT    7    5    8    9   10                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    7   11   16                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12    5   14   15                                             
CONECT   14   13                                                            
CONECT   15   13    2   16                                                  
CONECT   16   15   10                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
Patchoulol	MeSH
Patchouli alcohol	MeSH

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol

Traditional Name

2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol

CAS Registry Number

Not Available

SMILES

CC1CCC2(O)C(C)(C)C3CCC2(C)C1C3

InChI Identifier

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

InChI Key

GGHMUJBZYLPWFD-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Nardostachys jatamansi	LOTUS Database	35616633
Pogostemon cablin	LOTUS Database	35616633
Valeriana fauriei	LOTUS Database	35616633

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

a sesquiterpenoid (CPD-11399 )

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	4.19	ALOGPS
logP	3.5	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	0.29	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	66.22 m³·mol⁻¹	ChemAxon
Polarizability	26.75 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

Patchoulol

METLIN ID

Not Available

PubChem Compound

521903

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol (NP0246792)

MOL for NP0246792 (2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol)

3D MOL for NP0246792 (2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol)

3D SDF for NP0246792 (2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol)

3D-SDF for NP0246792 (2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol)

PDB for NP0246792 (2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol)

3D PDB for NP0246792 (2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol)

SMILES for NP0246792 (2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol)

INCHI for NP0246792 (2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol)

Structure for NP0246792 (2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol)

3D Structure for NP0246792 (2,2,6,8-tetramethyltricyclo[5.3.1.0³,⁸]undecan-3-ol)