Showing metabocard for Perilla alcohol (MMDBc0047743)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 15:40:36 UTC
Update Date2024-09-28 01:57:56 UTC
Metabolite IDMMDBc0047743
Metabolite Identification
Common NamePerilla alcohol
DescriptionPerillyl alcohol is a monoterpene isolated from the essential oils of lavendin, peppermint, spearmint, cherries, celery seeds, and several other plants. In animal studies it has been shown to regress pancreatic, mammary, and liver tumors, to exhibit possible application as a chemopreventative agent for colon, skin, and lung cancer, and as a chemotherapeutic agent for neuroblastoma, and prostate and colon cancer.(PMID:9855569 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f920a15ad08>

Perillyl alcohol
  Mrv1652305271900252D          

 11 11  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f920a15ad08>

HMDB0003634
     RDKit          3D
Perillyl alcohol
 27 27  0  0  0  0  0  0  0  0999 V2000
   -2.8500   -1.3720   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2746   -0.2303    0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192    0.9322    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -0.0665    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1166   -1.3899    0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3642   -1.2424    0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264   -0.1040   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4073   -0.0140   -0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7366    1.0452    0.8097 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1950    1.0707   -0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878    0.9900   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -2.2978   -0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -1.4656   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959    1.8843    0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464    0.7090    1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9494    0.9990   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6469    0.2633    1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070   -1.8134   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -2.0880    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9402   -2.0644    0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8666    0.1570   -1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.9257    0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093    0.9414    0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6045    1.9707   -0.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782    1.2693   -1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650    1.9735   -0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7653    0.8686   -1.6077 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  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 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
 10 25  1  0
 11 26  1  0
 11 27  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007f920a15ad08>

Perillyl alcohol
  Mrv1652305271900252D          

 11 11  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
  4 11  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0047743

> <DATABASE_NAME>
MIME

> <SMILES>
CC(=C)C1CCC(CO)=CC1

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3

> <INCHI_KEY>
NDTYTMIUWGWIMO-UHFFFAOYSA-N

> <FORMULA>
C10H16O

> <MOLECULAR_WEIGHT>
152.237

> <EXACT_MASS>
152.120115135

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
18.186695411456675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
1.9390414949999997

> <ALOGPS_LOGS>
-1.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.85657008950134

> <JCHEM_PKA_STRONGEST_BASIC>
-1.986736242852114

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
48.254999999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-perillylalcohol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007f920a15ad08>

HMDB0003634
     RDKit          3D
Perillyl alcohol
 27 27  0  0  0  0  0  0  0  0999 V2000
   -2.8500   -1.3720   -0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2746   -0.2303    0.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2192    0.9322    0.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125   -0.0665    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1166   -1.3899    0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3642   -1.2424    0.2245 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9264   -0.1040   -0.1533 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4073   -0.0140   -0.0674 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7366    1.0452    0.8097 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1950    1.0707   -0.6495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2878    0.9900   -0.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3116   -2.2978   -0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9284   -1.4656   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6959    1.8843    0.4131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7464    0.7090    1.3244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9494    0.9990   -0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6469    0.2633    1.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4070   -1.8134   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4172   -2.0880    0.9610 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9402   -2.0644    0.5757 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8666    0.1570   -1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.9257    0.3422 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093    0.9414    0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6045    1.9707   -0.1026 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782    1.2693   -1.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650    1.9735   -0.2178 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7653    0.8686   -1.6077 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  2  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 11  4  1  0
  1 12  1  0
  1 13  1  0
  3 14  1  0
  3 15  1  0
  3 16  1  0
  4 17  1  0
  5 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
 10 25  1  0
 11 26  1  0
 11 27  1  0
M  END
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PDB for #<Metabolite:0x00007f920a15ad08>

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Perillyl alcohol                                  
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   11                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11                                                       
CONECT   11   10    4                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for #<Metabolite:0x00007f920a15ad08>

COMPND    HMDB0003634
HETATM    1  C1  UNL     1      -2.850  -1.372  -0.214  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.275  -0.230   0.150  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.219   0.932   0.368  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.812  -0.067   0.338  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.117  -1.390   0.160  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.364  -1.242   0.225  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.926  -0.104  -0.153  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.407  -0.014  -0.067  1.00  0.00           C  
HETATM    9  O1  UNL     1       3.737   1.045   0.810  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.195   1.071  -0.650  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.288   0.990  -0.592  1.00  0.00           C  
HETATM   12  H1  UNL     1      -2.312  -2.298  -0.408  1.00  0.00           H  
HETATM   13  H2  UNL     1      -3.928  -1.466  -0.347  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.696   1.884   0.413  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.746   0.709   1.324  1.00  0.00           H  
HETATM   16  H5  UNL     1      -3.949   0.999  -0.485  1.00  0.00           H  
HETATM   17  H6  UNL     1      -0.647   0.263   1.388  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.407  -1.813  -0.815  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.417  -2.088   0.961  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.940  -2.064   0.576  1.00  0.00           H  
HETATM   21  H10 UNL     1       3.867   0.157  -1.062  1.00  0.00           H  
HETATM   22  H11 UNL     1       3.866  -0.926   0.342  1.00  0.00           H  
HETATM   23  H12 UNL     1       4.709   0.941   0.986  1.00  0.00           H  
HETATM   24  H13 UNL     1       1.605   1.971  -0.103  1.00  0.00           H  
HETATM   25  H14 UNL     1       1.478   1.269  -1.725  1.00  0.00           H  
HETATM   26  H15 UNL     1      -0.665   1.973  -0.218  1.00  0.00           H  
HETATM   27  H16 UNL     1      -0.765   0.869  -1.608  1.00  0.00           H  
CONECT    1    2    2   12   13
CONECT    2    3    4
CONECT    3   14   15   16
CONECT    4    5   11   17
CONECT    5    6   18   19
CONECT    6    7    7   20
CONECT    7    8   10
CONECT    8    9   21   22
CONECT    9   23
CONECT   10   11   24   25
CONECT   11   26   27
END
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SMILES for #<Metabolite:0x00007f920a15ad08>

CC(=C)C1CCC(CO)=CC1
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INCHI for #<Metabolite:0x00007f920a15ad08>

InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
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Synonyms
ValueSource
1-Hydroxymethyl-4-isopropenyl-1-cyclohexeneChEBI
1-PerillalcoholChEBI
4-(1-Methylethenyl)-1-cyclohexene-1-methanolChEBI
4-Isopropenyl-1-cyclohexene carbinolChEBI
4-Isopropenylcyclohex-1-en-1-ylmethanolChEBI
Dihydrocuminyl alcoholnChEBI
IsocarveolChEBI
p-Mentha-1,8-dien-7-olChEBI
Perilla alcoholChEBI
PerillolChEBI
(-)-Perillyl alcoholHMDB
(S)-(-)-Perillyl alcoholHMDB
1,8-p-Menthadien-7-olHMDB
4-Isopropenyl-cyclohex-1-ene-1-methanolHMDB
Dihydrocuminic alcoholHMDB
Dihydrocuminyl alcoholHMDB
Hydrocumin alcoholHMDB
Iso-carveolHMDB
Para-mentha-1,8-dien-7-olHMDB
Perill alcoholHMDB
Perillic alcoholHMDB
Cyclohex-1-ene-1-methanol, 4(1-methylethenyl)HMDB
Perilla alcohol, (S)-isomerHMDB
Perilla alcohol, (R)-isomerHMDB
(-)-p-Mentha-1,8-dien-7-olHMDB
(S)-Perillyl alcoholHMDB
Molecular FormulaC10H16O
Average Mass152.237
Monoisotopic Mass152.120115135
IUPAC Name[4-(prop-1-en-2-yl)cyclohex-1-en-1-yl]methanol
Traditional Name(-)-perillylalcohol
CAS Registry NumberNot Available
SMILES
CC(=C)C1CCC(CO)=CC1
InChI Identifier
InChI=1S/C10H16O/c1-8(2)10-5-3-9(7-11)4-6-10/h3,10-11H,1,4-7H2,2H3
InChI KeyNDTYTMIUWGWIMO-UHFFFAOYSA-N