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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:46:54 UTC

Update Date

2022-03-07 02:54:37 UTC

HMDB ID

HMDB0035760

Secondary Accession Numbers

HMDB35760

Metabolite Identification

Common Name

3-Hydroxytrichothecene

Description

3-Hydroxytrichothecene, also known as isotrichodermol, belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain. 3-Hydroxytrichothecene is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0035760
     RDKit          3D
3-Hydroxytrichothecene
 40 43  0  0  0  0  0  0  0  0999 V2000
    4.2932    0.3720    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.1567    0.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0427    1.2050    0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5900    1.0301    0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0340    0.9930    1.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3582    1.0326    1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9736   -0.2742    1.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3376    0.0088    2.0418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8115   -1.2193    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2539   -0.4067   -0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404   -0.7793   -1.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454   -0.3300   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8632   -0.4976   -1.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8490   -1.3602    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268   -1.2254    0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7555    0.9789   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3679    1.9024   -0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2166    1.0507   -0.2250 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5679    1.4444    0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6888   -0.0912   -0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7727   -0.1479    1.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    2.2000    0.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1046    1.8376   -0.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    1.9033    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -0.6281    2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4108    0.9620    2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567   -2.1237    0.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8376   -1.5511    0.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4333   -0.0925   -2.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9410   -0.5433   -1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084   -1.8299   -2.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -0.9982   -1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457    0.4379   -2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2680   -1.2318   -2.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6222   -2.4017    0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237   -1.1349    1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476   -1.5075    1.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8803   -1.9167   -0.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3367    1.7825   -2.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3521    2.9933   -0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 15  2  1  0
 18 16  1  0
 12  4  1  0
 16  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
M  END


  Mrv0541 05061308422D          

 18 21  0  0  0  0            999 V2000
    4.3097   -1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0003    0.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1096    0.3274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3989   -0.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6257   -0.0198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9007   -1.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7400   -1.2658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2087    0.3051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5364   -1.1209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1197   -1.6427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1275   -1.3591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6396   -0.9304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9900   -0.5456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0605   -0.5572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4999   -0.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4878   -2.2009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5114    0.7076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6113   -0.9304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13  2  1  0  0  0  0
 13  5  1  0  0  0  0
 13 11  1  0  0  0  0
 14  3  1  0  0  0  0
 14  7  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 10  1  0  0  0  0
 17  8  1  0  0  0  0
 17 15  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035760

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC2OC3C(O)CC(C)(C33CO3)C2(C)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-9-4-5-13(2)11(6-9)18-12-10(16)7-14(13,3)15(12)8-17-15/h6,10-12,16H,4-5,7-8H2,1-3H3

> <INCHI_KEY>
ICJDGHMOMSQSLB-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
27.53986057205481

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-ol

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
1.6945160883333326

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.07711742105063

> <JCHEM_PKA_STRONGEST_BASIC>
-3.202468840032454

> <JCHEM_POLAR_SURFACE_AREA>
41.989999999999995

> <JCHEM_REFRACTIVITY>
67.81450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035760
     RDKit          3D
3-Hydroxytrichothecene
 40 43  0  0  0  0  0  0  0  0999 V2000
    4.2932    0.3720    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.1567    0.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0427    1.2050    0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5900    1.0301    0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0340    0.9930    1.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3582    1.0326    1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9736   -0.2742    1.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3376    0.0088    2.0418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8115   -1.2193    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2539   -0.4067   -0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404   -0.7793   -1.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454   -0.3300   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8632   -0.4976   -1.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8490   -1.3602    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268   -1.2254    0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7555    0.9789   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3679    1.9024   -0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2166    1.0507   -0.2250 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5679    1.4444    0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6888   -0.0912   -0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7727   -0.1479    1.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    2.2000    0.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1046    1.8376   -0.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    1.9033    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -0.6281    2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4108    0.9620    2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567   -2.1237    0.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8376   -1.5511    0.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4333   -0.0925   -2.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9410   -0.5433   -1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084   -1.8299   -2.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -0.9982   -1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457    0.4379   -2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2680   -1.2318   -2.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6222   -2.4017    0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237   -1.1349    1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476   -1.5075    1.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8803   -1.9167   -0.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3367    1.7825   -2.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3521    2.9933   -0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 15  2  1  0
 18 16  1  0
 12  4  1  0
 16  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.045  -2.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.734   0.482   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.071   0.611   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.345  -0.574   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.901  -0.037   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.415  -3.074   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.381  -2.363   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.390   0.570   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.601  -2.092   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.223  -3.066   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.194  -1.737   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.715  -1.018   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.980  -1.040   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.933  -0.219   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.911  -4.108   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.955   1.321   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.008  -1.737   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    5    9                                                       
CONECT    5    4   13                                                       
CONECT    6    9   11                                                       
CONECT    7   10   14                                                       
CONECT    8   15   17                                                       
CONECT    9    1    4    6                                                  
CONECT   10    7   12   16                                                  
CONECT   11    6   13   18                                                  
CONECT   12   10   15   18                                                  
CONECT   13    2    5   11   14                                             
CONECT   14    3    7   13   15                                             
CONECT   15    8   12   14   17                                             
CONECT   16   10                                                            
CONECT   17    8   15                                                       
CONECT   18   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   42    0
END

COMPND    HMDB0035760
HETATM    1  C1  UNL     1       4.293   0.372   0.355  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.817   0.157   0.354  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.043   1.205   0.158  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.590   1.030   0.151  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.034   0.993   1.430  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.358   1.033   1.341  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.974  -0.274   1.838  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.338   0.009   2.042  1.00  0.00           O  
HETATM    9  C7  UNL     1      -1.811  -1.219   0.668  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.254  -0.407  -0.482  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.840  -0.779  -1.799  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.245  -0.330  -0.471  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.863  -0.498  -1.817  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.849  -1.360   0.488  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.327  -1.225   0.574  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.755   0.979  -0.095  1.00  0.00           C  
HETATM   17  C15 UNL     1      -2.368   1.902  -0.899  1.00  0.00           C  
HETATM   18  O3  UNL     1      -3.217   1.051  -0.225  1.00  0.00           O  
HETATM   19  H1  UNL     1       4.568   1.444   0.343  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.689  -0.091  -0.580  1.00  0.00           H  
HETATM   21  H3  UNL     1       4.773  -0.148   1.220  1.00  0.00           H  
HETATM   22  H4  UNL     1       2.492   2.200   0.002  1.00  0.00           H  
HETATM   23  H5  UNL     1       0.105   1.838  -0.467  1.00  0.00           H  
HETATM   24  H6  UNL     1      -1.705   1.903   1.893  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.542  -0.628   2.766  1.00  0.00           H  
HETATM   26  H8  UNL     1      -3.411   0.962   2.341  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.257  -2.124   0.891  1.00  0.00           H  
HETATM   28  H10 UNL     1      -2.838  -1.551   0.333  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.433  -0.092  -2.563  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.941  -0.543  -1.749  1.00  0.00           H  
HETATM   31  H13 UNL     1      -1.708  -1.830  -2.076  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.864  -0.998  -1.683  1.00  0.00           H  
HETATM   33  H15 UNL     1       1.046   0.438  -2.354  1.00  0.00           H  
HETATM   34  H16 UNL     1       0.268  -1.232  -2.418  1.00  0.00           H  
HETATM   35  H17 UNL     1       0.622  -2.402   0.150  1.00  0.00           H  
HETATM   36  H18 UNL     1       0.424  -1.135   1.487  1.00  0.00           H  
HETATM   37  H19 UNL     1       2.648  -1.508   1.613  1.00  0.00           H  
HETATM   38  H20 UNL     1       2.880  -1.917  -0.099  1.00  0.00           H  
HETATM   39  H21 UNL     1      -2.337   1.783  -2.022  1.00  0.00           H  
HETATM   40  H22 UNL     1      -2.352   2.993  -0.640  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3   15
CONECT    3    4   22
CONECT    4    5   12   23
CONECT    5    6
CONECT    6    7   16   24
CONECT    7    8    9   25
CONECT    8   26
CONECT    9   10   27   28
CONECT   10   11   12   16
CONECT   11   29   30   31
CONECT   12   13   14
CONECT   13   32   33   34
CONECT   14   15   35   36
CONECT   15   37   38
CONECT   16   17   18
CONECT   17   18   39   40
END

HMDB0035760
     RDKit          3D
3-Hydroxytrichothecene
 40 43  0  0  0  0  0  0  0  0999 V2000
    4.2932    0.3720    0.3548 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8173    0.1567    0.3540 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0427    1.2050    0.1584 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5900    1.0301    0.1514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0340    0.9930    1.4301 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3582    1.0326    1.3407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9736   -0.2742    1.8375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3376    0.0088    2.0418 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8115   -1.2193    0.6678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2539   -0.4067   -0.4820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8404   -0.7793   -1.7991 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2454   -0.3300   -0.4706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8632   -0.4976   -1.8173 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8490   -1.3602    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3268   -1.2254    0.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7555    0.9789   -0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3679    1.9024   -0.8990 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2166    1.0507   -0.2250 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5679    1.4444    0.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6888   -0.0912   -0.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7727   -0.1479    1.2198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4922    2.2000    0.0025 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1046    1.8376   -0.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7052    1.9033    1.8931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5419   -0.6281    2.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4108    0.9620    2.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2567   -2.1237    0.8914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8376   -1.5511    0.3327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4333   -0.0925   -2.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9410   -0.5433   -1.7491 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7084   -1.8299   -2.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -0.9982   -1.6828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0457    0.4379   -2.3541 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2680   -1.2318   -2.4176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6222   -2.4017    0.1499 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4237   -1.1349    1.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6476   -1.5075    1.6134 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8803   -1.9167   -0.0987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3367    1.7825   -2.0221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3521    2.9933   -0.6405 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 10 16  1  0
 16 17  1  0
 17 18  1  0
 15  2  1  0
 18 16  1  0
 12  4  1  0
 16  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 17 39  1  0
 17 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12,13-Epoxy-(3alpha)-trichothec-9-en-3-ol	HMDB
12,13-Epoxy-trichothec-9-en-3alpha-ol	HMDB
Isotrichodermol	HMDB

Chemical Formula

C₁₅H₂₂O₃

Average Molecular Weight

250.3334

Monoisotopic Molecular Weight

250.15689457

IUPAC Name

1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-ol

Traditional Name

1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-ol

CAS Registry Number

104155-10-4

SMILES

CC1=CC2OC3C(O)CC(C)(C33CO3)C2(C)CC1

InChI Identifier

InChI=1S/C15H22O3/c1-9-4-5-13(2)11(6-9)18-12-10(16)7-14(13,3)15(12)8-17-15/h6,10-12,16H,4-5,7-8H2,1-3H3

InChI Key

ICJDGHMOMSQSLB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as trichothecenes. These are sesquiterpene mycotoxins structurally characterized by the presence of an epoxide ring and a benzopyran derivative with a variant number of hydroxyl, acetyl, or other substituents. The most important structural features causing the biological activities of trichothecenes are the 12,13-epoxy ring, the presence of hydroxyl or acetyl groups at appropriate positions on the trichothecene nucleus and the structure and position of the side-chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Trichothecenes

Alternative Parents

Substituents

Trichothecene skeleton
Oxepane
Oxane
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0035760)

Cellular substructure

Extracellular (HMDB: HMDB0035760)
Cytoplasm (HMDB: HMDB0035760)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035760)

Source

Endogenous

Endogenous (HMDB: HMDB0035760)

Animal

Animal (HMDB: HMDB0035760)

Exogenous

Food

Food (HMDB: HMDB0035760)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0035760)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0035760)

Cellular process

Cell signaling (HMDB: HMDB0035760)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0035760)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0035760)

Nutrient

Nutrient (HMDB: HMDB0035760)

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	0.95 g/L	ALOGPS
logP	1.6	ALOGPS
logP	1.69	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	14.08	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	41.99 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.81 m³·mol⁻¹	ChemAxon
Polarizability	27.54 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	160.219	31661259
DarkChem	[M-H]-	153.914	31661259
DeepCCS	[M-2H]-	196.818	30932474
DeepCCS	[M+Na]+	172.383	30932474
AllCCS	[M+H]+	160.5	32859911
AllCCS	[M+H-H2O]+	156.9	32859911
AllCCS	[M+NH4]+	163.9	32859911
AllCCS	[M+Na]+	164.9	32859911
AllCCS	[M-H]-	167.0	32859911
AllCCS	[M+Na-2H]-	166.9	32859911
AllCCS	[M+HCOO]-	166.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxytrichothecene	CC1=CC2OC3C(O)CC(C)(C33CO3)C2(C)CC1	2907.7	Standard polar	33892256
3-Hydroxytrichothecene	CC1=CC2OC3C(O)CC(C)(C33CO3)C2(C)CC1	1864.4	Standard non polar	33892256
3-Hydroxytrichothecene	CC1=CC2OC3C(O)CC(C)(C33CO3)C2(C)CC1	1873.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxytrichothecene,1TMS,isomer #1	CC1=CC2OC3C(O[Si](C)(C)C)CC(C)(C2(C)CC1)C31CO1	1983.5	Semi standard non polar	33892256
3-Hydroxytrichothecene,1TBDMS,isomer #1	CC1=CC2OC3C(O[Si](C)(C)C(C)(C)C)CC(C)(C2(C)CC1)C31CO1	2254.2	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 - 3-Hydroxytrichothecene GC-MS (Non-derivatized) - 70eV, Positive	splash10-05uf-5970000000-fde9c9e09cc660be7c1d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxytrichothecene GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-3943000000-47370dcabcc6aa80c2dd	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxytrichothecene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxytrichothecene 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 - 3-Hydroxytrichothecene 10V, Positive-QTOF	splash10-0udi-0190000000-19c3c23ec879ba29b91e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytrichothecene 20V, Positive-QTOF	splash10-0f6x-3960000000-48ff2eaea85bb194ba93	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytrichothecene 40V, Positive-QTOF	splash10-0gb9-9510000000-3f72f71b30bd49df4330	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytrichothecene 10V, Negative-QTOF	splash10-0002-0190000000-afc49c0e2a118a943c0b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytrichothecene 20V, Negative-QTOF	splash10-0002-0290000000-7098821015f449c46f6f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytrichothecene 40V, Negative-QTOF	splash10-0a5c-4900000000-fb04cd77ebf968383863	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytrichothecene 10V, Negative-QTOF	splash10-0002-0090000000-0dd1e5565d33dd37f20a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytrichothecene 20V, Negative-QTOF	splash10-0002-0190000000-ce2e11bb3a3bc62ce6f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytrichothecene 40V, Negative-QTOF	splash10-00r2-0090000000-6c9002c730116691e0f5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytrichothecene 10V, Positive-QTOF	splash10-0udi-0090000000-34de332e5087c8fb7170	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytrichothecene 20V, Positive-QTOF	splash10-0udi-0490000000-908df11176477be84328	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxytrichothecene 40V, Positive-QTOF	splash10-0pb9-2590000000-f8f76be2cd5c75c48a31	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB014496

KNApSAcK ID

C00012644

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13857027

PDB ID

Not Available

ChEBI ID

Not Available

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for 3-Hydroxytrichothecene (HMDB0035760)

MOL for HMDB0035760 (3-Hydroxytrichothecene)

3D MOL for HMDB0035760 (3-Hydroxytrichothecene)

3D SDF for HMDB0035760 (3-Hydroxytrichothecene)

3D-SDF for HMDB0035760 (3-Hydroxytrichothecene)

PDB for HMDB0035760 (3-Hydroxytrichothecene)

3D PDB for HMDB0035760 (3-Hydroxytrichothecene)

SMILES for HMDB0035760 (3-Hydroxytrichothecene)

INCHI for HMDB0035760 (3-Hydroxytrichothecene)

Structure for HMDB0035760 (3-Hydroxytrichothecene)

3D Structure for HMDB0035760 (3-Hydroxytrichothecene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra