Showing metabocard for trans-3-hexen-1-ol (MMDBc0033456)

Plant
Xenobiotic
Record Information
Version2.0
StatusDetected and Quantified
Creation Date2021-11-19 04:49:23 UTC
Update Date2025-10-07 16:07:59 UTC
Metabolite IDMMDBc0033456
Metabolite Identification
Common Nametrans-3-hexen-1-ol
Descriptiontrans-3-hexen-1-ol is a linear alcohol classified within the chemical class of aliphatic alcohols. Its chemical structure features a six-carbon chain with a hydroxyl group (-OH) located at the terminal position, specifically at the first carbon, and a double bond between the third and fourth carbons, which contributes to its reactivity and sensory properties. This compound is involved in various biochemical pathways, including the synthesis of pheromones, as evidenced by its use in a novel asymmetric synthesis of (-)-dehydro-exo-brevicomin, a sex pheromone in house mice (PMID:34328158 ). Additionally, trans-3-hexen-1-ol has been correlated with environmental factors, such as cold nights prior to harvest, which influence its concentration in plants (PMID:29424428 ). Its presence is also noted in the volatile profiles of various fruits and plants, contributing to their aroma, as seen in kiwi distillates (PMID:22321168 ) and in the cashew water phase, where it imparts green grass and fruity notes (PMID:21681760 ). Furthermore, studies indicate a greater antennal response to its cis isomer compared to trans-3-hexen-1-ol itself, highlighting its significance in ecological interactions (PMID:25598579 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007f9a9ac7f0d8>


  Mrv1652307301919572D          

  7  6  0  0  0  0            999 V2000
    2.2613   -0.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5468    0.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -0.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179    0.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5966   -0.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    0.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256   -0.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x00007f9a9ac7f0d8>

HMDB0302264
     RDKit          3D
Hex-trans-3-en-1-ol
 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.5508    0.7139   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1974   -0.5853    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7709   -0.9333    0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132   -0.1866   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6228   -0.6510   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4705    0.2915    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    1.5712    0.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6070    0.6451   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6241    1.5254    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432    1.0698   -1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -0.6371    1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7227   -1.4159   -0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5118   -1.8965    0.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0118    0.7657   -0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1045   -0.7169   -1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6844   -1.6697    0.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.3639    1.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716   -0.1540    0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.8998    0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
M  END
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3D SDF for #<Metabolite:0x00007f9a9ac7f0d8>


  Mrv1652307301919572D          

  7  6  0  0  0  0            999 V2000
    2.2613   -0.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5468    0.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8323   -0.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1179    0.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5966   -0.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3111    0.0316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0256   -0.3809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033456

> <DATABASE_NAME>
MIME

> <SMILES>
CC\C=C\CCO

> <INCHI_IDENTIFIER>
InChI=1S/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3+

> <INCHI_KEY>
UFLHIIWVXFIJGU-ONEGZZNKSA-N

> <FORMULA>
C6H12O

> <MOLECULAR_WEIGHT>
100.1589

> <EXACT_MASS>
100.088815006

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
12.460237000487005

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3E)-hex-3-en-1-ol

> <JCHEM_LOGP>
1.3325376193333331

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.791790810402865

> <JCHEM_PKA_STRONGEST_BASIC>
-2.015070699529785

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
32.4535

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-hexene-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for #<Metabolite:0x00007f9a9ac7f0d8>

HMDB0302264
     RDKit          3D
Hex-trans-3-en-1-ol
 19 18  0  0  0  0  0  0  0  0999 V2000
   -2.5508    0.7139   -0.5221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1974   -0.5853    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7709   -0.9333    0.0890 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2132   -0.1866   -0.3496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6228   -0.6510   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4705    0.2915    0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    1.5712    0.0396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6070    0.6451   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6241    1.5254    0.2610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432    1.0698   -1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5775   -0.6371    1.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7227   -1.4159   -0.4973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5118   -1.8965    0.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0118    0.7657   -0.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1045   -0.7169   -1.2647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6844   -1.6697    0.1746 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0198    0.3639    1.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4716   -0.1540    0.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4382    1.8998    0.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  2 12  1  0
  3 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
M  END
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PDB for #<Metabolite:0x00007f9a9ac7f0d8>

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       4.221  -0.711   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.887   0.059   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.554  -0.711   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.220   0.059   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.114  -0.711   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.447   0.059   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -3.781  -0.711   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for #<Metabolite:0x00007f9a9ac7f0d8>

COMPND    HMDB0302264
HETATM    1  C1  UNL     1      -2.551   0.714  -0.522  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.197  -0.585   0.055  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.771  -0.933   0.089  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.213  -0.187  -0.350  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.623  -0.651  -0.259  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.470   0.291   0.577  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.492   1.571   0.040  1.00  0.00           O  
HETATM    8  H1  UNL     1      -3.607   0.645  -0.922  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.624   1.525   0.261  1.00  0.00           H  
HETATM   10  H3  UNL     1      -1.943   1.070  -1.360  1.00  0.00           H  
HETATM   11  H4  UNL     1      -2.578  -0.637   1.102  1.00  0.00           H  
HETATM   12  H5  UNL     1      -2.723  -1.416  -0.497  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.512  -1.897   0.517  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.012   0.766  -0.775  1.00  0.00           H  
HETATM   15  H8  UNL     1       2.105  -0.717  -1.265  1.00  0.00           H  
HETATM   16  H9  UNL     1       1.684  -1.670   0.175  1.00  0.00           H  
HETATM   17  H10 UNL     1       2.020   0.364   1.604  1.00  0.00           H  
HETATM   18  H11 UNL     1       3.472  -0.154   0.681  1.00  0.00           H  
HETATM   19  H12 UNL     1       3.438   1.900   0.123  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3   11   12
CONECT    3    4    4   13
CONECT    4    5   14
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7   19
END
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SMILES for #<Metabolite:0x00007f9a9ac7f0d8>

CC\C=C\CCO
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INCHI for #<Metabolite:0x00007f9a9ac7f0d8>

InChI=1S/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3+
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Synonyms
ValueSource
(3E)-3-Hexen-1-olChEBI
(3E)-Hexen-1-olChEBI
(3E)-HexenolChEBI
(e)-3-Hexen-1-olChEBI
(e)-3-HexenolChEBI
trans-3-HexenolChEBI
trans-Hex-3-en-1-olChEBI
3-Hexen-1-ol, (e)-isomerMeSH
cis-3-HexenolMeSH
cis-3-Hexen-1-olMeSH
3-Hexen-1-olMeSH
3-Hexen-1-ol, (Z)-isomerMeSH
Molecular FormulaC6H12O
Average Mass100.1589
Monoisotopic Mass100.088815006
IUPAC Name(3E)-hex-3-en-1-ol
Traditional Name3-hexene-1-ol
CAS Registry Number928-97-2
SMILES
CC\C=C\CCO
InChI Identifier
InChI=1S/C6H12O/c1-2-3-4-5-6-7/h3-4,7H,2,5-6H2,1H3/b4-3+
InChI KeyUFLHIIWVXFIJGU-ONEGZZNKSA-N