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Showing metabocard for Cuminyl alcohol (HMDB0031817)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:45:39 UTC
Update Date2023-02-21 17:21:19 UTC
HMDB IDHMDB0031817
Secondary Accession Numbers
  • HMDB31817
Metabolite Identification
Common NameCuminyl alcohol
DescriptionCuminol or Cuminyl alcohol, also known as p-cumin-7-ol or 4-Isopropylbenzyl alcohol, belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. 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-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Cuminol is an extremely weak basic (essentially neutral) compound (based on its pKa). Cuminol is an alcohol derivative of p-Cymene. It exists as a clear, colorless liquid that is poorly soluble in water. Cuminol can be used as a food additive or as a cosmetic fragrance. It has a cumin, caraway or spicy, herbal aroma and a similar spicy, herbal or peppery taste. Cuminol is found naturally in a number of plants, spices and foods including cumin seed and cumin oils, caraway eucalyptus oils, thyme, sunflowers, tuermeric, guava fruit and other spices and essential oils. Cumin, a widely used spice, is known to have anti-diabetic properties and two of its phytochemicals: cuminol and cuminaldehyde appear to be among the most active components. Cuminol is a potent insulinotrophic molecule that can enhance insulin secretion by up to 4-fold (in rat islet cells) (PMID:23507295 ). It also exhibits strong beta-cell protective action (PMID:23507295 ).
Structure
Data?1677000079
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031817 (Cuminyl alcohol)

Cuminaldehyde metabolite 5
  Mrv1652303202019012D          

 11 11  0  0  0  0            999 V2000
    0.4195   -2.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -3.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4195   -1.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0094   -2.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -1.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0094   -1.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7239   -3.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4384   -2.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7240   -3.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340   -1.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8485   -1.8880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
Download

3D MOL for HMDB0031817 (Cuminyl alcohol)

HMDB0031817
     RDKit          3D
Cuminyl alcohol
 25 25  0  0  0  0  0  0  0  0999 V2000
    2.7156    1.2079    0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1199   -0.0980   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6217   -1.2619    0.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6468   -0.0249   -0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2033   -0.1685   -1.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5531   -0.0947   -0.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570    0.1226    0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5180    0.2136    0.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1835    0.0420   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2238    0.2696    1.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1294    0.1947    1.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8240    1.2072    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3450    1.9849   -0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3850    1.5392    1.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3382   -0.2750   -1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4402   -1.1400    1.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0895   -2.1736    0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7026   -1.4388    0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2337   -0.3408   -2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506   -0.2073   -1.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7522    1.2138    0.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7646   -0.5785    1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2552   -0.9503   -0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6022    0.4434    2.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7719    0.3134    2.0295 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
 11  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
  5 19  1  0
  6 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
M  END
Download

3D SDF for HMDB0031817 (Cuminyl alcohol)

Cuminaldehyde metabolite 5
  Mrv1652303202019012D          

 11 11  0  0  0  0            999 V2000
    0.4195   -2.7130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -3.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4195   -1.8879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0094   -2.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2949   -1.4755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0094   -1.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7239   -3.1254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4384   -2.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7240   -3.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1340   -1.4754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8485   -1.8880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031817

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=CC=C(CO)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-6,8,11H,7H2,1-2H3

> <INCHI_KEY>
OIGWAXDAPKFNCQ-UHFFFAOYSA-N

> <FORMULA>
C10H14O

> <MOLECULAR_WEIGHT>
150.221

> <EXACT_MASS>
150.104465071

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.98170487902889

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[4-(propan-2-yl)phenyl]methanol

> <ALOGPS_LOGP>
2.63

> <JCHEM_LOGP>
2.4509051993333335

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.049780525298221

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7770259982345573

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
47.0647

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cuminol

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for HMDB0031817 (Cuminyl alcohol)

HMDB0031817
     RDKit          3D
Cuminyl alcohol
 25 25  0  0  0  0  0  0  0  0999 V2000
    2.7156    1.2079    0.1455 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1199   -0.0980   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6217   -1.2619    0.5433 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6468   -0.0249   -0.1025 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2033   -0.1685   -1.1668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5531   -0.0947   -0.9760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570    0.1226    0.2772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5180    0.2136    0.5530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1835    0.0420   -0.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2238    0.2696    1.3588 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1294    0.1947    1.1621 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8240    1.2072    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3450    1.9849   -0.5550 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3850    1.5392    1.1612 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3382   -0.2750   -1.3195 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4402   -1.1400    1.6244 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0895   -2.1736    0.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7026   -1.4388    0.3996 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2337   -0.3408   -2.1530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2506   -0.2073   -1.8164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7522    1.2138    0.9854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7646   -0.5785    1.2759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2552   -0.9503   -0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6022    0.4434    2.3659 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7719    0.3134    2.0295 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  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  2  0
 11  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
  5 19  1  0
  6 20  1  0
  8 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 11 25  1  0
M  END
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PDB for HMDB0031817 (Cuminyl alcohol)

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Cuminaldehyde metabolite 5                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       0.783  -5.064   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.550  -5.834   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.783  -3.524   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.884  -5.064   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.550  -2.754   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.884  -3.524   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.218  -5.834   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.552  -5.064   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.218  -7.374   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.117  -2.754   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.451  -3.524   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5   10                                                  
CONECT    4    2    6    7                                                  
CONECT    5    3    6                                                       
CONECT    6    4    5                                                       
CONECT    7    4    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0031817 (Cuminyl alcohol)

COMPND    HMDB0031817
HETATM    1  C1  UNL     1       2.716   1.208   0.146  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.120  -0.098  -0.264  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.622  -1.262   0.543  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.647  -0.025  -0.103  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.203  -0.169  -1.167  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.553  -0.095  -0.976  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.057   0.123   0.277  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.518   0.214   0.553  1.00  0.00           C  
HETATM    9  O1  UNL     1      -4.183   0.042  -0.652  1.00  0.00           O  
HETATM   10  C9  UNL     1      -1.224   0.270   1.359  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.129   0.195   1.162  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.824   1.207   0.101  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.345   1.985  -0.555  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.385   1.539   1.161  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.338  -0.275  -1.319  1.00  0.00           H  
HETATM   16  H5  UNL     1       2.440  -1.140   1.624  1.00  0.00           H  
HETATM   17  H6  UNL     1       2.090  -2.174   0.146  1.00  0.00           H  
HETATM   18  H7  UNL     1       3.703  -1.439   0.400  1.00  0.00           H  
HETATM   19  H8  UNL     1       0.234  -0.341  -2.153  1.00  0.00           H  
HETATM   20  H9  UNL     1      -2.251  -0.207  -1.816  1.00  0.00           H  
HETATM   21  H10 UNL     1      -3.752   1.214   0.985  1.00  0.00           H  
HETATM   22  H11 UNL     1      -3.765  -0.578   1.276  1.00  0.00           H  
HETATM   23  H12 UNL     1      -4.255  -0.950  -0.787  1.00  0.00           H  
HETATM   24  H13 UNL     1      -1.602   0.443   2.366  1.00  0.00           H  
HETATM   25  H14 UNL     1       0.772   0.313   2.030  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4   15
CONECT    3   16   17   18
CONECT    4    5    5   11
CONECT    5    6   19
CONECT    6    7    7   20
CONECT    7    8   10
CONECT    8    9   21   22
CONECT    9   23
CONECT   10   11   11   24
CONECT   11   25
END
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SMILES for HMDB0031817 (Cuminyl alcohol)

CC(C)C1=CC=C(CO)C=C1
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INCHI for HMDB0031817 (Cuminyl alcohol)

InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-6,8,11H,7H2,1-2H3
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View in JSmolView Stereo Labels
Synonyms
Chemical FormulaC10H14O
Average Molecular Weight150.221
Monoisotopic Molecular Weight150.104465071
IUPAC Name[4-(propan-2-yl)phenyl]methanol
Traditional Namecuminol
CAS Registry Number536-60-7
SMILES
CC(C)C1=CC=C(CO)C=C1
InChI Identifier
InChI=1S/C10H14O/c1-8(2)10-5-3-9(7-11)4-6-10/h3-6,8,11H,7H2,1-2H3
InChI KeyOIGWAXDAPKFNCQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAromatic monoterpenoids
Alternative Parents
Substituents
  • Monocyclic monoterpenoid
  • Aromatic monoterpenoid
  • P-cymene
  • Phenylpropane
  • Cumene
  • Benzyl alcohol
  • Benzenoid
  • Monocyclic benzene moiety
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point28 °CNot Available
Boiling Point135.00 to 136.00 °C. @ 26.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP2.370The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB008492
KNApSAcK IDC00032864
Chemspider ID21105932
KEGG Compound IDC06576
BioCyc IDCPD-1002
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound325
PDB IDNot Available
ChEBI ID27628
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1016451
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  6. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.