NP-MRD: Showing NP-Card for (1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol (NP0323857)

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Record Information

Version

2.0

Created at

2022-09-12 03:33:20 UTC

Updated at

2022-09-12 03:33:20 UTC

NP-MRD ID

NP0323857

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol

Description

(1R,4S,5R)-4-Thujanol, also known as (1R,4S,5R)-form or sabinene hydrate, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other (1R,4S,5R)-4-Thujanol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, (1R,4S,5R)-4-Thujanol has been detected, but not quantified in, herbs and spices. (1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol is found in Abies sibirica, Anthriscus nitida, Croton sarcopetalus, Cryptomeria japonica, Larix laricina, Melaleuca alternifolia, Ocimum gratissimum, Origanum dictamnus, Picea koraiensis, Picea schrenkiana, Pinus densiflora, Polygala senega and Rhododendron mucronulatum. This could make (1R,4S,5R)-4-thujanol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    1.5474    1.5102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1771    2.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932    2.7304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596    1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7413    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596   -1.2135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2495   -2.5838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1586   -1.9635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4330   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8660    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9177    0.9001    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3937    0.6379    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1575    2.8805    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7872    3.4906    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5635    3.3405    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831    4.1007    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7386    2.0325    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1586    1.9635    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7058    2.0858    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8560   -1.0037    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8560    1.0037    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6394   -3.9542    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5352   -3.3564    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1850   -2.1453    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3415   -3.4523    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3396   -2.0357    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0796    0.8816    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8302   -1.1491    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  2  1  1
  4 11  1  0
 11 10  1  0
 10  7  1  0
  7  8  1  0
  7  9  1  1
  7  6  1  0
  6  5  1  0
 10  4  1  0
  5  4  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  3 17  1  0
  3 18  1  0
 11 28  1  0
 11 29  1  0
 10 27  1  6
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  6 21  1  0
  6 22  1  0
  5 19  1  0
  5 20  1  0
M  END

View in JSmol

Synonyms

Value	Source
(1R,4S,5R)-Form	HMDB
Sabinene hydrate	HMDB

Chemical Formula

C₁₀H₁₈O

Average Mass

154.2493 Da

Monoisotopic Mass

154.13577 Da

IUPAC Name

(1R,2S,5R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hexan-2-ol

Traditional Name

(1R,2S,5R)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol

CAS Registry Number

Not Available

SMILES

CC(C)[C@@]12C[C@H]1[C@@](C)(O)CC2

InChI Identifier

InChI=1S/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3/t8-,9-,10?/m0/s1

InChI Key

KXSDPILWMGFJMM-XMCUXHSSSA-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
Abies sibirica	LOTUS Database	35616633
Anthriscus nitida	LOTUS Database	35616633
Croton sarcopetalus	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Larix laricina	LOTUS Database	35616633
Melaleuca alternifolia	LOTUS Database	35616633
Ocimum gratissimum	LOTUS Database	35616633
Origanum dictamnus	LOTUS Database	35616633
Picea koraiensis	LOTUS Database	35616633
Picea schrenkiana	LOTUS Database	35616633
Pinus densiflora	LOTUS Database	35616633
Polygala senega	LOTUS Database	35616633
Rhododendron mucronulatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Not Available

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	2.12	ALOGPS
logP	1.89	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	19.13	ChemAxon
pKa (Strongest Basic)	-0.99	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	1	ChemAxon
Refractivity	45.55 m³·mol⁻¹	ChemAxon
Polarizability	25.81 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0036112

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014959

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

12315154

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol (NP0323857)

MOL for NP0323857 ((1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)

3D MOL for NP0323857 ((1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)

3D SDF for NP0323857 ((1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)

3D-SDF for NP0323857 ((1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)

PDB for NP0323857 ((1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)

3D PDB for NP0323857 ((1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)

SMILES for NP0323857 ((1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)

INCHI for NP0323857 ((1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)

Structure for NP0323857 ((1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)

3D Structure for NP0323857 ((1r,2s)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol)