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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-04-03 14:10:33 UTC

Update Date

2021-09-14 15:19:02 UTC

HMDB ID

HMDB0013688

Secondary Accession Numbers

HMDB13688

Metabolite Identification

Common Name

Nootkatol

Description

Nootkatol, also known as trans-nootkatol, belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. Based on a literature review a significant number of articles have been published on Nootkatol.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0013688
     RDKit          3D
Nootkatol
 40 41  0  0  0  0  0  0  0  0999 V2000
    3.2682    1.4161    0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9175    0.1636    0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6253   -0.7771    1.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8761   -0.3974   -0.3011 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5249    0.5095   -1.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3522    1.4059   -1.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5729    0.8695   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2746    1.6303    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2113    1.1429    1.6704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5053    1.4626    1.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9651   -0.2908    2.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7248   -1.1081    0.7752 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0117   -1.0899   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6115   -0.6319   -0.0896 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8231   -1.2350   -1.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7446   -1.0080    0.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310    1.7568    1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    2.1473    0.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936   -1.2966    0.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -1.5134    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0605   -0.2197    2.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3943   -1.2926   -0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128    1.1482   -1.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3949   -0.0677   -2.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7032    2.4248   -1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046    1.4817   -2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987    2.7144    0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9474    1.7448    2.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173    2.3591    0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8878   -0.6886    2.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580   -0.4112    2.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436   -2.1675    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3332   -2.1059   -0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682   -0.7088    0.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829   -0.4521   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7061   -1.9042   -1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -1.9115   -1.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838   -0.4481   -2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7768   -0.5523    1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8554   -2.0988    0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  6
 14 16  1  0
 16  4  1  0
 14  7  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  6
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  1
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  1
 13 33  1  0
 13 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
M  END

 
  Mrv0541 02271202162D          
 
 16 17  0  0  1  0            999 V2000
   14.4788  -14.3963    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4788  -15.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1800  -15.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8813  -15.2213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8813  -14.3963    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1800  -13.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7363  -13.9838    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.0350  -14.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0350  -15.2213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7363  -15.6338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3338  -15.6338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6238  -13.9838    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3250  -14.3963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6238  -13.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4788  -13.5713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7363  -13.1588    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
  1  6  1  0  0  0  0
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  2 10  2  0  0  0  0
  9 11  1  1  0  0  0
  5 12  1  6  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
  1 15  1  1  0  0  0
  7 16  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0013688

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1C[C@H](O)C=C2CC[C@H](C[C@@]12C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12,14,16H,1,5-7,9H2,2-4H3/t11-,12-,14+,15+/m1/s1

> <INCHI_KEY>
GFNWRKNVTHDNPV-UXOAXIEHSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.694554058333694

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-ol

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
3.2884983246666684

> <ALOGPS_LOGS>
-3.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.824686557402345

> <JCHEM_PKA_STRONGEST_BASIC>
-1.5632820997922146

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
68.9679

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydro-2H-naphthalen-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0013688
     RDKit          3D
Nootkatol
 40 41  0  0  0  0  0  0  0  0999 V2000
    3.2682    1.4161    0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9175    0.1636    0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6253   -0.7771    1.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8761   -0.3974   -0.3011 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5249    0.5095   -1.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3522    1.4059   -1.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5729    0.8695   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2746    1.6303    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2113    1.1429    1.6704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5053    1.4626    1.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9651   -0.2908    2.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7248   -1.1081    0.7752 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0117   -1.0899   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6115   -0.6319   -0.0896 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8231   -1.2350   -1.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7446   -1.0080    0.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310    1.7568    1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    2.1473    0.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936   -1.2966    0.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -1.5134    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0605   -0.2197    2.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3943   -1.2926   -0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128    1.1482   -1.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3949   -0.0677   -2.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7032    2.4248   -1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046    1.4817   -2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987    2.7144    0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9474    1.7448    2.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173    2.3591    0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8878   -0.6886    2.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580   -0.4112    2.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436   -2.1675    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3332   -2.1059   -0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682   -0.7088    0.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829   -0.4521   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7061   -1.9042   -1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -1.9115   -1.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838   -0.4481   -2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7768   -0.5523    1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8554   -2.0988    0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  6
 14 16  1  0
 16  4  1  0
 14  7  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  6
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  1
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  1
 13 33  1  0
 13 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0      27.027 -26.873   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      27.027 -28.413   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      28.336 -29.183   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.645 -28.413   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.645 -26.873   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      28.336 -26.103   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.641 -26.103   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      24.332 -26.873   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.332 -28.413   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.641 -29.183   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      23.023 -29.183   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      31.031 -26.103   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      32.340 -26.873   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      31.031 -24.563   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      27.027 -25.333   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      25.641 -24.563   0.000  0.00  0.00           C+0
CONECT    1    2    6    7   15                                             
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    1                                                       
CONECT    7    1    8   16                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    2                                                       
CONECT   11    9                                                            
CONECT   12    5   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1                                                            
CONECT   16    7                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0013688
HETATM    1  C1  UNL     1       3.268   1.416   0.643  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.918   0.164   0.612  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.625  -0.777   1.568  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.876  -0.397  -0.301  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.525   0.510  -1.424  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.352   1.406  -1.209  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.573   0.870  -0.164  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.275   1.630   0.611  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.211   1.143   1.670  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.505   1.463   1.351  1.00  0.00           O  
HETATM   11  C10 UNL     1      -1.965  -0.291   2.019  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.725  -1.108   0.775  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.012  -1.090  -0.016  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.611  -0.632  -0.090  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.823  -1.235  -1.481  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.745  -1.008   0.455  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.031   1.757   1.324  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.817   2.147   0.006  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.394  -1.297   0.933  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.850  -1.513   1.874  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.060  -0.220   2.397  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.394  -1.293  -0.807  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.413   1.148  -1.658  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.395  -0.068  -2.402  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.703   2.425  -1.010  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.205   1.482  -2.186  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.199   2.714   0.508  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.947   1.745   2.589  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.517   2.359   0.961  1.00  0.00           H  
HETATM   30  H14 UNL     1      -2.888  -0.689   2.490  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.158  -0.411   2.770  1.00  0.00           H  
HETATM   32  H16 UNL     1      -1.544  -2.168   1.059  1.00  0.00           H  
HETATM   33  H17 UNL     1      -3.333  -2.106  -0.346  1.00  0.00           H  
HETATM   34  H18 UNL     1      -3.868  -0.709   0.596  1.00  0.00           H  
HETATM   35  H19 UNL     1      -2.983  -0.452  -0.911  1.00  0.00           H  
HETATM   36  H20 UNL     1      -1.706  -1.904  -1.525  1.00  0.00           H  
HETATM   37  H21 UNL     1       0.034  -1.912  -1.739  1.00  0.00           H  
HETATM   38  H22 UNL     1      -0.984  -0.448  -2.246  1.00  0.00           H  
HETATM   39  H23 UNL     1       0.777  -0.552   1.490  1.00  0.00           H  
HETATM   40  H24 UNL     1       0.855  -2.099   0.603  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3    4
CONECT    3   19   20   21
CONECT    4    5   16   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8    8   14
CONECT    8    9   27
CONECT    9   10   11   28
CONECT   10   29
CONECT   11   12   30   31
CONECT   12   13   14   32
CONECT   13   33   34   35
CONECT   14   15   16
CONECT   15   36   37   38
CONECT   16   39   40
END

HMDB0013688
     RDKit          3D
Nootkatol
 40 41  0  0  0  0  0  0  0  0999 V2000
    3.2682    1.4161    0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9175    0.1636    0.6120 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6253   -0.7771    1.5678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8761   -0.3974   -0.3011 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5249    0.5095   -1.4240 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3522    1.4059   -1.2094 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5729    0.8695   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2746    1.6303    0.6111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2113    1.1429    1.6704 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.5053    1.4626    1.3510 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9651   -0.2908    2.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7248   -1.1081    0.7752 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0117   -1.0899   -0.0161 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6115   -0.6319   -0.0896 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8231   -1.2350   -1.4813 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7446   -1.0080    0.4554 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0310    1.7568    1.3241 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    2.1473    0.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936   -1.2966    0.9335 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8500   -1.5134    1.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0605   -0.2197    2.3973 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3943   -1.2926   -0.8071 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4128    1.1482   -1.6576 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3949   -0.0677   -2.4015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7032    2.4248   -1.0100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2046    1.4817   -2.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1987    2.7144    0.5081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9474    1.7448    2.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5173    2.3591    0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8878   -0.6886    2.4898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1580   -0.4112    2.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5436   -2.1675    1.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3332   -2.1059   -0.3464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8682   -0.7088    0.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9829   -0.4521   -0.9107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7061   -1.9042   -1.5252 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0336   -1.9115   -1.7387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9838   -0.4481   -2.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7768   -0.5523    1.4904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8554   -2.0988    0.6030 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  6
 14 16  1  0
 16  4  1  0
 14  7  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  6
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  9 28  1  1
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  1
 13 33  1  0
 13 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-trans-Nootkatol	ChEBI
2alpha-Hydroxy-4alpha,5alpha,7beta-eremophil-1(10),11-diene	ChEBI
2alpha-Hydroxyvalencene	ChEBI
4alpha,4Aalpha-dimethyl-6beta-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2alpha-ol	ChEBI
trans-Nootkatol	ChEBI
2a-Hydroxy-4a,5a,7b-eremophil-1(10),11-diene	Generator
2Α-hydroxy-4α,5α,7β-eremophil-1(10),11-diene	Generator
2a-Hydroxyvalencene	Generator
2Α-hydroxyvalencene	Generator
4a,4Aalpha-dimethyl-6b-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2a-ol	Generator
4Α,4aalpha-dimethyl-6β-(1-methylethenyl)-2,3,4,4a,5,6,7,8-octahydronaphthalene-2α-ol	Generator
Nootkatol, (2S-(2alpha,4alpha,4aalpha,6beta))-isomer	HMDB
b-Nootkatol	HMDB
Β-nootkatol	HMDB
Nootkatol	ChEBI

Chemical Formula

C₁₅H₂₄O

Average Molecular Weight

220.3505

Monoisotopic Molecular Weight

220.18271539

IUPAC Name

(2S,4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-ol

Traditional Name

(2S,4R,4aS,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydro-2H-naphthalen-2-ol

CAS Registry Number

53643-07-5

SMILES

C[C@@H]1C[C@H](O)C=C2CC[C@H](C[C@@]12C)C(C)=C

InChI Identifier

InChI=1S/C15H24O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12,14,16H,1,5-7,9H2,2-4H3/t11-,12-,14+,15+/m1/s1

InChI Key

GFNWRKNVTHDNPV-UXOAXIEHSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:81378 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0013688)

Source

Endogenous

Endogenous (HMDB: HMDB0013688)

Sweet orange (FooDB: FOOD00057)

Process

Not Available

Role

Biological role

Calcium antagonist (HMDB: HMDB0013688)

Industrial application

Vasodilator agent (HMDB: HMDB0013688)

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.078 g/L	ALOGPS
logP	4.08	ALOGPS
logP	3.29	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	17.82	ChemAxon
pKa (Strongest Basic)	-1.6	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	68.97 m³·mol⁻¹	ChemAxon
Polarizability	26.69 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	150.322	31661259
DarkChem	[M-H]-	150.334	31661259
DeepCCS	[M-2H]-	190.111	30932474
DeepCCS	[M+Na]+	165.269	30932474
AllCCS	[M+H]+	153.9	32859911
AllCCS	[M+H-H2O]+	150.1	32859911
AllCCS	[M+NH4]+	157.5	32859911
AllCCS	[M+Na]+	158.5	32859911
AllCCS	[M-H]-	160.5	32859911
AllCCS	[M+Na-2H]-	161.0	32859911
AllCCS	[M+HCOO]-	161.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nootkatol	C[C@@H]1C[C@H](O)C=C2CC[C@H](C[C@@]12C)C(C)=C	2376.2	Standard polar	33892256
Nootkatol	C[C@@H]1C[C@H](O)C=C2CC[C@H](C[C@@]12C)C(C)=C	1688.4	Standard non polar	33892256
Nootkatol	C[C@@H]1C[C@H](O)C=C2CC[C@H](C[C@@]12C)C(C)=C	1703.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nootkatol,1TMS,isomer #1	C=C(C)[C@@H]1CCC2=C[C@@H](O[Si](C)(C)C)C[C@@H](C)[C@]2(C)C1	1855.9	Semi standard non polar	33892256
Nootkatol,1TBDMS,isomer #1	C=C(C)[C@@H]1CCC2=C[C@@H](O[Si](C)(C)C(C)(C)C)C[C@@H](C)[C@]2(C)C1	2131.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nootkatol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0m2i-1920000000-36a53dc0cd76085f13c2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nootkatol GC-MS (1 TMS) - 70eV, Positive	splash10-00b9-3190000000-f6eac8d604a4f232394d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nootkatol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nootkatol 10V, Positive-QTOF	splash10-0uk9-0190000000-8ec95bc5726f9b21b807	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nootkatol 20V, Positive-QTOF	splash10-0w9r-3940000000-7a09938ffe5201609336	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nootkatol 40V, Positive-QTOF	splash10-0170-7900000000-ea440a51463123369b61	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nootkatol 10V, Negative-QTOF	splash10-014i-0090000000-50f7b73a74632bc5e170	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nootkatol 20V, Negative-QTOF	splash10-014i-0090000000-dfc27b7829643a3f9c8b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nootkatol 40V, Negative-QTOF	splash10-0ftr-1930000000-aaeb15fd7d4dbae8cb32	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nootkatol 10V, Positive-QTOF	splash10-024i-0970000000-d107739323e2ab89b8f3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nootkatol 20V, Positive-QTOF	splash10-08i0-1910000000-1bb2ae294deb25ebe725	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nootkatol 40V, Positive-QTOF	splash10-0006-9400000000-7f8a56fb1970f16513ed	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nootkatol 10V, Negative-QTOF	splash10-014i-0090000000-4af4c4ee1c4acef7e18b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nootkatol 20V, Negative-QTOF	splash10-014i-0090000000-8193001bf63f74c63975	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nootkatol 40V, Negative-QTOF	splash10-014i-0590000000-e26e4b6e21b359364bc6	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00052878

Chemspider ID

158847

KEGG Compound ID

C17915

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

182645

PDB ID

Not Available

ChEBI ID

81378

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Nootkatol (HMDB0013688)

MOL for HMDB0013688 (Nootkatol)

3D MOL for HMDB0013688 (Nootkatol)

3D SDF for HMDB0013688 (Nootkatol)

3D-SDF for HMDB0013688 (Nootkatol)

PDB for HMDB0013688 (Nootkatol)

3D PDB for HMDB0013688 (Nootkatol)

SMILES for HMDB0013688 (Nootkatol)

INCHI for HMDB0013688 (Nootkatol)

Structure for HMDB0013688 (Nootkatol)

3D Structure for HMDB0013688 (Nootkatol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra