NP-MRD: Showing NP-Card for (+)-Axenol (NP0064637)

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Record Information

Version

2.0

Created at

2022-04-28 08:50:11 UTC

Updated at

2022-04-28 08:50:11 UTC

NP-MRD ID

NP0064637

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+)-Axenol

Description

(-)-Gleenol, also known as gleenol, belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. (+)-Axenol is found in Cryptomeria japonica, Dictyota dichotoma, Eurypon sp., Juniperus oxycedrus, Pelargonium endlicherianum and Taonia atomaria. (+)-Axenol was first documented in 2007 (PMID: 17978520). The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (-)-Gleenol is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 30704081).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -3.8947    0.6089   -1.9837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8912    0.0993   -0.9798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6082    0.4013   -0.8930 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9382   -0.3001    0.2303 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9775   -1.3493    0.6369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2842   -0.8579    0.0786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7411    0.6211    1.4035 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0907    2.0477    0.9688 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6713    0.6602    1.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6246    0.9347    0.7501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4114    0.0100   -0.4014 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6909   -0.6250   -0.8904 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6953    0.4063   -1.3550 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3624   -1.4668    0.1603 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3164   -0.9966   -0.1882 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6524   -1.9846    0.7159 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1460   -0.1927   -2.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7689    0.9488   -1.3839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4982    1.5163   -2.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1528    1.1060   -1.6122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0715   -1.3760    1.7575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7681   -2.3321    0.2066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9043   -0.3784    0.8765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8674   -1.6972   -0.3981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4213    0.3757    2.2449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2018    2.0857    0.8916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8094    2.6991    1.8414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697    2.3124    0.0463 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9647   -0.2286    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7596    1.5328    2.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4536    2.0186    0.4838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6423    0.9044    1.1800 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0524    0.6512   -1.2633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4943   -1.2862   -1.7594 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2680    0.8498   -0.5354 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2379    1.1519   -2.0357 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4425   -0.1521   -1.9868 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008   -0.9919    1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4269   -1.5900   -0.1629 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9433   -2.4966    0.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1325   -1.4924   -1.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381   -2.1474    1.3992 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  1  0
 12 11  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  0
  7  4  1  0
  4  5  1  1
  5  6  1  0
  6  2  1  0
  2  1  1  0
  2  3  2  0
  4 15  1  0
 15 16  1  0
 15 11  1  0
  4  3  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 12 34  1  6
 14 38  1  0
 14 39  1  0
 14 40  1  0
 11 33  1  6
 10 31  1  0
 10 32  1  0
  9 29  1  0
  9 30  1  0
  7 25  1  1
  8 26  1  0
  8 27  1  0
  8 28  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
 15 41  1  6
 16 42  1  0
M  END


  Mrv1652309272006432D          

 16 17  0  0  0  0            999 V2000
 9999.471010000.2645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4607 9997.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5123 9999.9610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7976 9999.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.512310000.7868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9499 9999.5502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7220 9999.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.7509 9998.4499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9499 9998.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.3805 9999.7794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0549 9999.5502    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.2300 9999.5502    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9997.8175 9998.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2300 9998.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0549 9998.1213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.4675 9998.8357    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  7 10  1  0  0  0  0
 11 12  1  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 12  3  1  1  0  0  0
 15  2  1  6  0  0  0
 11  1  1  1  0  0  0
 16  9  1  1  0  0  0
 16  6  1  6  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0064637

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)[C@@H]1CC[C@@H](C)[C@]2(CCC(C)=C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-10(2)13-6-5-12(4)15(14(13)16)8-7-11(3)9-15/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13+,14-,15-/m1/s1

> <INCHI_KEY>
MYLXGCVCCZCOHU-LXTVHRRPSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
27.66718106879889

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S,6R,7S,10R)-2,10-dimethyl-7-(propan-2-yl)spiro[4.5]dec-1-en-6-ol

> <ALOGPS_LOGP>
3.72

> <JCHEM_LOGP>
3.714097865666666

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.09930837830726347

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
69.11339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.12e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S,6R,7S,10R)-7-isopropyl-2,10-dimethylspiro[4.5]dec-1-en-6-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8665.6798667.160   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8665.6608661.816   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8662.0238666.594   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8660.6898665.827   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8662.0238668.135   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8666.5738665.827   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8668.0148665.326   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.0688663.773   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.5738663.273   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8669.2448666.255   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.9038665.827   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8663.3638665.827   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8662.5938664.493   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8663.3638663.160   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.9038663.160   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8665.6738664.493   0.000  0.00  0.00           C+0
CONECT    1   11                                                            
CONECT    2   15                                                            
CONECT    3    4    5   12                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6   16    7                                                       
CONECT    7   10    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9   16    8                                                       
CONECT   10    7                                                            
CONECT   11   12   16    1                                                  
CONECT   12   11   13    3                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16    2                                                  
CONECT   16   11   15    9    6                                             
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
Gleenol	MeSH
(-)-Gleenol	PhytoBank
Axenol	PhytoBank

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

(5S,6R,7S,10R)-2,10-dimethyl-7-(propan-2-yl)spiro[4.5]dec-1-en-6-ol

Traditional Name

(5S,6R,7S,10R)-7-isopropyl-2,10-dimethylspiro[4.5]dec-1-en-6-ol

CAS Registry Number

Not Available

SMILES

CC(C)[C@@H]1CC[C@@H](C)[C@]2(CCC(C)=C2)[C@@H]1O

InChI Identifier

InChI=1S/C15H26O/c1-10(2)13-6-5-12(4)15(14(13)16)8-7-11(3)9-15/h9-10,12-14,16H,5-8H2,1-4H3/t12-,13+,14-,15-/m1/s1

InChI Key

MYLXGCVCCZCOHU-LXTVHRRPSA-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
Cryptomeria japonica	LOTUS Database	35616633
Dictyota dichotoma	LOTUS Database	35616633
Eurypon sp.	-	KNApSAcK
Juniperus oxycedrus	LOTUS Database	35616633
Pelargonium endlicherianum	LOTUS Database	35616633
Taonia atomaria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	3.72	ALOGPS
logP	3.71	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-0.099	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	69.11 m³·mol⁻¹	ChemAxon
Polarizability	27.67 Å³	ChemAxon
Number of Rings	2	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

4934457

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6429080

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Jerkovic I, Kranjac M, Marijanovic Z, Roje M, Jokic S: Chemical Diversity of Headspace and Volatile Oil Composition of Two Brown Algae (Taonia atomaria and Padina pavonica) from the Adriatic Sea. Molecules. 2019 Jan 30;24(3). pii: molecules24030495. doi: 10.3390/molecules24030495. [PubMed:30704081 ]
Nakazaki A, Era T, Kobayashi S: Total synthesis of (+/-)-gleenol and (+/-)-axenol via a functionalized spiro[4.5]decane. Chem Pharm Bull (Tokyo). 2007 Nov;55(11):1606-9. doi: 10.1248/cpb.55.1606. [PubMed:17978520 ]

Showing NP-Card for (+)-Axenol (NP0064637)

MOL for NP0064637 ((+)-Axenol)

3D MOL for NP0064637 ((+)-Axenol)

3D SDF for NP0064637 ((+)-Axenol)

3D-SDF for NP0064637 ((+)-Axenol)

PDB for NP0064637 ((+)-Axenol)

3D PDB for NP0064637 ((+)-Axenol)

SMILES for NP0064637 ((+)-Axenol)

INCHI for NP0064637 ((+)-Axenol)

Structure for NP0064637 ((+)-Axenol)

3D Structure for NP0064637 ((+)-Axenol)