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Showing metabocard for alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol (HMDB0303866)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 05:14:39 UTC
Update Date2021-09-24 05:14:39 UTC
HMDB IDHMDB0303866
Secondary Accession NumbersNone
Metabolite Identification
Common Namealpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol
DescriptionFenchol or 1,3,3-Trimethylbicyclo[2.2.1]heptan-2-ol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Fenchol is a naturally occurring bicyclic monoterpenoid and an isomer of Borneol. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in the plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclation reactions to yield a diverse number of cyclic arrangements. Fenchol is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a colorless or white solid with a characteristic scent found in basil and Aster. Fenchol is used extensively in perfumery.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0303866 (alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol)

  Mrv1652309272007432D          

 11 12  0  0  0  0            999 V2000
 9999.5809 9998.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0085 9999.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.869510000.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.105510000.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.575310001.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.579310001.0706    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.864810000.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8648 9999.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5793 9999.4206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.2938 9999.8330    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.293810000.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  6 11  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
 10 11  1  0  0  0  0
  1  9  1  0  0  0  0
 10  2  1  1  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
  6  3  1  6  0  0  0
  9  3  1  6  0  0  0
M  END
Download

3D MOL for HMDB0303866 (alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol)

HMDB0303866
     RDKit          3D
alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol
 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.3232   -0.7629   -0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1263    0.0738    0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5954    1.4143    0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1959    0.2412   -1.0745 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1887    1.5473   -1.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1130   -0.2127   -0.5181 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1683   -0.5058   -1.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660    0.6337    0.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137    0.2905    1.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3274   -0.6804    1.1679 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6379   -1.4563    0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1881   -0.4259    0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387   -0.6588   -1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1646   -1.8463    0.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8998    1.4197    1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093    1.7152    0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583    2.2271    0.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257   -0.4912   -1.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517    1.5075   -2.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9943   -1.5005   -1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1557   -0.5202   -0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2333    0.3027   -2.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    0.3013    0.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    1.7099    0.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1413   -0.2158    2.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1247    1.2047    2.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8975   -1.3076    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1138   -2.1609   -0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4969   -1.8437    0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10  2  1  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  6
  5 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  1
 11 28  1  0
 11 29  1  0
M  END
Download

3D SDF for HMDB0303866 (alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol)

  Mrv1652309272007432D          

 11 12  0  0  0  0            999 V2000
 9999.5809 9998.5959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0085 9999.4209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.869510000.2457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.105510000.5139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.575310001.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.579310001.0706    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.864810000.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.8648 9999.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.5793 9999.4206    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.2938 9999.8330    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.293810000.6581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0  0  0  0
  6 11  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
 10 11  1  0  0  0  0
  1  9  1  0  0  0  0
 10  2  1  1  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
  6  3  1  6  0  0  0
  9  3  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0303866

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)[C@@H]2CC[C@@](C)(C2)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1

> <INCHI_KEY>
IAIHUHQCLTYTSF-MRTMQBJTSA-N

> <FORMULA>
C10H18O

> <MOLECULAR_WEIGHT>
154.253

> <EXACT_MASS>
154.1357652

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
18.5178324248877

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.1453653443333334

> <ALOGPS_LOGS>
-2.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5162855018399258

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
45.1603

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
((endo)-(+-))-fenchol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0303866 (alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol)

HMDB0303866
     RDKit          3D
alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol
 29 30  0  0  0  0  0  0  0  0999 V2000
   -2.3232   -0.7629   -0.2200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1263    0.0738    0.1259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5954    1.4143    0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1959    0.2412   -1.0745 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1887    1.5473   -1.5352 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1130   -0.2127   -0.5181 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1683   -0.5058   -1.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5660    0.6337    0.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6137    0.2905    1.8083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3274   -0.6804    1.1679 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.6379   -1.4563    0.2550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1881   -0.4259    0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387   -0.6588   -1.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1646   -1.8463    0.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8998    1.4197    1.6691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5093    1.7152    0.0251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8583    2.2271    0.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257   -0.4912   -1.8258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517    1.5075   -2.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9943   -1.5005   -1.9564 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1557   -0.5202   -0.9627 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2333    0.3027   -2.2337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5750    0.3013    0.9443 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5565    1.7099    0.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1413   -0.2158    2.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1247    1.2047    2.1961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8975   -1.3076    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1138   -2.1609   -0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4969   -1.8437    0.8003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10  2  1  0
 11  6  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  3 15  1  0
  3 16  1  0
  3 17  1  0
  4 18  1  6
  5 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  1
 11 28  1  0
 11 29  1  0
M  END
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PDB for HMDB0303866 (alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol)

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  C   UNK     0    8665.8848664.046   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8668.5498665.586   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0    8666.4238667.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8668.7308667.626   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8667.7418669.343   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8665.8818668.665   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8664.5488667.895   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.5488666.355   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8665.8818665.585   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8667.2158666.355   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8667.2158667.895   0.000  0.00  0.00           C+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    6    9                                                       
CONECT    4   11                                                            
CONECT    5   11                                                            
CONECT    6    7   11    3                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    1    3                                             
CONECT   10    9   11    2                                                  
CONECT   11    6   10    4    5                                             
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END
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3D PDB for HMDB0303866 (alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol)

COMPND    HMDB0303866
HETATM    1  C1  UNL     1      -2.323  -0.763  -0.220  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.126   0.074   0.126  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.595   1.414   0.604  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.196   0.241  -1.075  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.189   1.547  -1.535  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.113  -0.213  -0.518  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.168  -0.506  -1.499  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.566   0.634   0.661  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.614   0.291   1.808  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.327  -0.680   1.168  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.638  -1.456   0.255  1.00  0.00           C  
HETATM   12  H1  UNL     1      -3.188  -0.426   0.402  1.00  0.00           H  
HETATM   13  H2  UNL     1      -2.639  -0.659  -1.276  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.165  -1.846   0.038  1.00  0.00           H  
HETATM   15  H4  UNL     1      -1.900   1.420   1.669  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.509   1.715   0.025  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.858   2.227   0.437  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.526  -0.491  -1.826  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.052   1.508  -2.533  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.994  -1.501  -1.956  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.156  -0.520  -0.963  1.00  0.00           H  
HETATM   22  H11 UNL     1       2.233   0.303  -2.234  1.00  0.00           H  
HETATM   23  H12 UNL     1       2.575   0.301   0.944  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.557   1.710   0.433  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.141  -0.216   2.632  1.00  0.00           H  
HETATM   26  H15 UNL     1       0.125   1.205   2.196  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.897  -1.308   1.822  1.00  0.00           H  
HETATM   28  H17 UNL     1       0.114  -2.161  -0.386  1.00  0.00           H  
HETATM   29  H18 UNL     1       1.497  -1.844   0.800  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   10
CONECT    3   15   16   17
CONECT    4    5    6   18
CONECT    5   19
CONECT    6    7    8   11
CONECT    7   20   21   22
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   11   27
CONECT   11   28   29
END
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SMILES for HMDB0303866 (alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol)

CC1(C)[C@@H]2CC[C@@](C)(C2)[C@@H]1O
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INCHI for HMDB0303866 (alpha-fenchyl alcoholalpha-1,3,3-trimethyl-norbornan-2-ol)

InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H18O
Average Molecular Weight154.253
Monoisotopic Molecular Weight154.1357652
IUPAC Name(1S,2S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-ol
Traditional Name((endo)-(+-))-fenchol
CAS Registry NumberNot Available
SMILES
CC1(C)[C@@H]2CC[C@@](C)(C2)[C@@H]1O
InChI Identifier
InChI=1S/C10H18O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7-8,11H,4-6H2,1-3H3/t7-,8-,10+/m1/s1
InChI KeyIAIHUHQCLTYTSF-MRTMQBJTSA-N
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Fenchane monoterpenoid
  • Bicyclic monoterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029688
KNApSAcK IDC00052452
Chemspider ID388777
KEGG Compound IDC02344
BioCyc IDCPD-685
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15405
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1054341
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available