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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:38:29 UTC

Update Date

2022-03-07 02:54:13 UTC

HMDB ID

HMDB0034738

Secondary Accession Numbers

HMDB34738

Metabolite Identification

Common Name

Isotrichodermin

Description

Isotrichodermin 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. Isotrichodermin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0034738
     RDKit          3D
Isotrichodermin
 45 48  0  0  0  0  0  0  0  0999 V2000
    4.8353    2.3031   -1.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1147    1.0088   -0.8801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7719   -0.0316   -1.1552 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795    0.9362   -0.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -0.3355   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484   -0.5164    1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2765   -1.1547    0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0394   -2.1413    1.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8094   -0.0739    0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0485    0.5546    2.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595   -0.8149    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    0.0941    0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9690    1.2946   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1232    2.0647   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    1.6499   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997    0.9726   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014    0.5875   -1.3140 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.5033   -1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3527   -1.6877   -0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0372   -2.8822   -1.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -2.8018   -0.5726 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1497    3.1706   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4540    2.2311   -1.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5709    2.3917   -0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151   -1.1605   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6310    0.4229    1.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2878   -1.2489    1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1648   -3.1992    1.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7770   -1.9714    2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9587   -2.0715    2.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5399   -0.1154    2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0851    0.8615    2.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6262    1.4891    1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1882   -1.7801    0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8765   -1.0090   -0.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1273   -0.4798    0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070    0.3575    1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8997    2.1281   -0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6224    1.5379   -1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8149    3.0998   -1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5811    2.5496   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    1.7851    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -0.8477   -2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6055   -3.6422   -0.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0492   -3.0219   -2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18  5  1  0
 21 19  1  0
 19  7  1  0
 16  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
M  END


  Mrv0541 05061308022D          

 21 24  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
    0.4790   -3.2531    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
    0.9168   -1.3542    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
   -0.3081   -3.0061    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
   -0.9156   -3.5643    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
   -0.4878   -2.2009    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
    1.0605    0.2678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9900    0.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  8  1  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  2  0  0  0  0
  9  2  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12 10  1  0  0  0  0
 13  4  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 14 13  1  0  0  0  0
 15  7  1  0  0  0  0
 15 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  2  0  0  0  0
 17  7  1  0  0  0  0
 17 15  1  0  0  0  0
 18  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 19 12  1  0  0  0  0
 14 20  1  0  0  0  0
 13 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034738

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)CCC21C

> <INCHI_IDENTIFIER>
InChI=1S/C17H24O4/c1-10-5-6-15(3)13(7-10)21-14-12(20-11(2)18)8-16(15,4)17(14)9-19-17/h7,12-14H,5-6,8-9H2,1-4H3

> <INCHI_KEY>
OZXJPPYWZVBMGW-UHFFFAOYSA-N

> <FORMULA>
C17H24O4

> <MOLECULAR_WEIGHT>
292.3701

> <EXACT_MASS>
292.167459256

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.76327896613377

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <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'-yl acetate

> <ALOGPS_LOGP>
2.16

> <JCHEM_LOGP>
2.135641498666665

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9304289390245315

> <JCHEM_POLAR_SURFACE_AREA>
48.06

> <JCHEM_REFRACTIVITY>
76.966

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.19e-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'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034738
     RDKit          3D
Isotrichodermin
 45 48  0  0  0  0  0  0  0  0999 V2000
    4.8353    2.3031   -1.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1147    1.0088   -0.8801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7719   -0.0316   -1.1552 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795    0.9362   -0.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -0.3355   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484   -0.5164    1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2765   -1.1547    0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0394   -2.1413    1.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8094   -0.0739    0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0485    0.5546    2.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595   -0.8149    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    0.0941    0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9690    1.2946   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1232    2.0647   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    1.6499   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997    0.9726   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014    0.5875   -1.3140 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.5033   -1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3527   -1.6877   -0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0372   -2.8822   -1.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -2.8018   -0.5726 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1497    3.1706   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4540    2.2311   -1.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5709    2.3917   -0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151   -1.1605   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6310    0.4229    1.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2878   -1.2489    1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1648   -3.1992    1.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7770   -1.9714    2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9587   -2.0715    2.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5399   -0.1154    2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0851    0.8615    2.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6262    1.4891    1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1882   -1.7801    0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8765   -1.0090   -0.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1273   -0.4798    0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070    0.3575    1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8997    2.1281   -0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6224    1.5379   -1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8149    3.0998   -1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5811    2.5496   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    1.7851    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -0.8477   -2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6055   -3.6422   -0.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0492   -3.0219   -2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18  5  1  0
 21 19  1  0
 19  7  1  0
 16  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  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       0.894  -6.072   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.345  -0.574   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.901  -0.037   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.415  -3.074   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.711  -2.528   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.390   0.570   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.601  -2.092   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.575  -5.611   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      -1.709  -6.653   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      -0.911  -4.108   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       3.008  -1.737   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.980   0.500   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.715   0.522   0.000  0.00  0.00           C+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    4    8                                                       
CONECT    4    3   13                                                       
CONECT    5    8   11                                                       
CONECT    6   10   14                                                       
CONECT    7   15   17                                                       
CONECT    8    1    3    5                                                  
CONECT    9    2   16   18                                                  
CONECT   10    6   12   18                                                  
CONECT   11    5   13   19                                                  
CONECT   12   10   15   19                                                  
CONECT   13    4   11   14   21                                             
CONECT   14    6   13   15   20                                             
CONECT   15    7   12   14   17                                             
CONECT   16    9                                                            
CONECT   17    7   15                                                       
CONECT   18    9   10                                                       
CONECT   19   11   12                                                       
CONECT   20   14                                                            
CONECT   21   13                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0034738
HETATM    1  C1  UNL     1       4.835   2.303  -1.014  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.115   1.009  -0.880  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.772  -0.032  -1.155  1.00  0.00           O  
HETATM    4  O2  UNL     1       2.780   0.936  -0.472  1.00  0.00           O  
HETATM    5  C3  UNL     1       2.218  -0.336  -0.386  1.00  0.00           C  
HETATM    6  C4  UNL     1       1.648  -0.516   1.003  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.277  -1.155   0.845  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.039  -2.141   1.917  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.809  -0.074   0.792  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.048   0.555   2.126  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.060  -0.815   0.298  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.241   0.094   0.400  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.969   1.295  -0.426  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.123   2.065  -0.951  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.746   1.650  -0.676  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.500   0.973  -0.215  1.00  0.00           C  
HETATM   17  O3  UNL     1       0.201   0.588  -1.314  1.00  0.00           O  
HETATM   18  C15 UNL     1       0.985  -0.503  -1.250  1.00  0.00           C  
HETATM   19  C16 UNL     1       0.353  -1.688  -0.536  1.00  0.00           C  
HETATM   20  C17 UNL     1       0.037  -2.882  -1.091  1.00  0.00           C  
HETATM   21  O4  UNL     1       1.339  -2.802  -0.573  1.00  0.00           O  
HETATM   22  H1  UNL     1       4.150   3.171  -1.025  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.454   2.231  -1.943  1.00  0.00           H  
HETATM   24  H3  UNL     1       5.571   2.392  -0.164  1.00  0.00           H  
HETATM   25  H4  UNL     1       2.915  -1.160  -0.659  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.631   0.423   1.550  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.288  -1.249   1.531  1.00  0.00           H  
HETATM   28  H7  UNL     1       0.165  -3.199   1.622  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.777  -1.971   2.751  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.959  -2.072   2.401  1.00  0.00           H  
HETATM   31  H10 UNL     1      -1.540  -0.115   2.856  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.085   0.861   2.561  1.00  0.00           H  
HETATM   33  H12 UNL     1      -1.626   1.489   1.953  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.188  -1.780   0.799  1.00  0.00           H  
HETATM   35  H14 UNL     1      -1.877  -1.009  -0.779  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.127  -0.480   0.012  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.507   0.358   1.444  1.00  0.00           H  
HETATM   38  H17 UNL     1      -4.900   2.128  -0.142  1.00  0.00           H  
HETATM   39  H18 UNL     1      -4.622   1.538  -1.799  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.815   3.100  -1.222  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.581   2.550  -1.295  1.00  0.00           H  
HETATM   42  H21 UNL     1       0.101   1.785   0.294  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.229  -0.848  -2.275  1.00  0.00           H  
HETATM   44  H23 UNL     1      -0.605  -3.642  -0.607  1.00  0.00           H  
HETATM   45  H24 UNL     1       0.049  -3.022  -2.208  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   18   25
CONECT    6    7   26   27
CONECT    7    8    9   19
CONECT    8   28   29   30
CONECT    9   10   11   16
CONECT   10   31   32   33
CONECT   11   12   34   35
CONECT   12   13   36   37
CONECT   13   14   15   15
CONECT   14   38   39   40
CONECT   15   16   41
CONECT   16   17   42
CONECT   17   18
CONECT   18   19   43
CONECT   19   20   21
CONECT   20   21   44   45
END

HMDB0034738
     RDKit          3D
Isotrichodermin
 45 48  0  0  0  0  0  0  0  0999 V2000
    4.8353    2.3031   -1.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1147    1.0088   -0.8801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7719   -0.0316   -1.1552 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7795    0.9362   -0.4720 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2177   -0.3355   -0.3859 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6484   -0.5164    1.0035 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2765   -1.1547    0.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0394   -2.1413    1.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8094   -0.0739    0.7923 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0485    0.5546    2.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0595   -0.8149    0.2980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2410    0.0941    0.4002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9690    1.2946   -0.4263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1232    2.0647   -0.9512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7457    1.6499   -0.6756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4997    0.9726   -0.2150 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2014    0.5875   -1.3140 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9845   -0.5033   -1.2498 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3527   -1.6877   -0.5355 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0372   -2.8822   -1.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3393   -2.8018   -0.5726 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1497    3.1706   -1.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4540    2.2311   -1.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5709    2.3917   -0.1640 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151   -1.1605   -0.6586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6310    0.4229    1.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2878   -1.2489    1.5314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1648   -3.1992    1.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7770   -1.9714    2.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9587   -2.0715    2.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5399   -0.1154    2.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0851    0.8615    2.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6262    1.4891    1.9533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1882   -1.7801    0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8765   -1.0090   -0.7791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1273   -0.4798    0.0120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5070    0.3575    1.4439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8997    2.1281   -0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6224    1.5379   -1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8149    3.0998   -1.2219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5811    2.5496   -1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1014    1.7851    0.2939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2287   -0.8477   -2.2754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6055   -3.6422   -0.6075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0492   -3.0219   -2.2080 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 18  5  1  0
 21 19  1  0
 19  7  1  0
 16  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 14 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12,13-Epoxy-acetate(3alpha)-tichothec-9-en-3-ol	HMDB
12,13-Epoxy-trichothec-9-ene-3-ol acetate	HMDB
1',2',5'-Trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetic acid	Generator
Isotrichodermin	MeSH

Chemical Formula

C₁₇H₂₄O₄

Average Molecular Weight

292.3701

Monoisotopic Molecular Weight

292.167459256

IUPAC Name

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

Traditional Name

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

CAS Registry Number

91423-90-4

SMILES

CC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)CCC21C

InChI Identifier

InChI=1S/C17H24O4/c1-10-5-6-15(3)13(7-10)21-14-12(20-11(2)18)8-16(15,4)17(14)9-19-17/h7,12-14H,5-6,8-9H2,1-4H3

InChI Key

OZXJPPYWZVBMGW-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
Carboxylic acid ester
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0034738)

Cellular substructure

Extracellular (HMDB: HMDB0034738)
Cytoplasm (HMDB: HMDB0034738)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034738)

Source

Endogenous

Endogenous (HMDB: HMDB0034738)

Animal

Animal (HMDB: HMDB0034738)

Exogenous

Food

Food (HMDB: HMDB0034738)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0034738)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0034738)

Cellular process

Cell signaling (HMDB: HMDB0034738)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0034738)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0034738)

Nutrient

Nutrient (HMDB: HMDB0034738)

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	0.12 g/L	ALOGPS
logP	2.16	ALOGPS
logP	2.14	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	48.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.97 m³·mol⁻¹	ChemAxon
Polarizability	31.76 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]+	168.924	31661259
DarkChem	[M-H]-	164.123	31661259
DeepCCS	[M-2H]-	198.927	30932474
DeepCCS	[M+Na]+	174.269	30932474
AllCCS	[M+H]+	171.1	32859911
AllCCS	[M+H-H2O]+	167.9	32859911
AllCCS	[M+NH4]+	174.1	32859911
AllCCS	[M+Na]+	175.0	32859911
AllCCS	[M-H]-	177.1	32859911
AllCCS	[M+Na-2H]-	177.1	32859911
AllCCS	[M+HCOO]-	177.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isotrichodermin	CC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)CCC21C	2997.9	Standard polar	33892256
Isotrichodermin	CC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)CCC21C	1945.0	Standard non polar	33892256
Isotrichodermin	CC(=O)OC1CC2(C)C3(CO3)C1OC1C=C(C)CCC21C	2060.8	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 - Isotrichodermin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-3890000000-b63210e2a4ef1521c745	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isotrichodermin 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 - Isotrichodermin 10V, Positive-QTOF	splash10-0006-0190000000-288514832dc58420d613	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrichodermin 20V, Positive-QTOF	splash10-0f7x-2970000000-68774e6875007edb3308	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrichodermin 40V, Positive-QTOF	splash10-0a4i-7910000000-424d83738d0ac5087690	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrichodermin 10V, Negative-QTOF	splash10-0006-2190000000-af2ee29fea20b34492f5	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrichodermin 20V, Negative-QTOF	splash10-052e-2190000000-5b8f8e7350dcb7e3b7a1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrichodermin 40V, Negative-QTOF	splash10-0a4l-5910000000-9f84bec163abe24468bf	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrichodermin 10V, Positive-QTOF	splash10-0006-0090000000-a2b536561579ef1661d1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrichodermin 20V, Positive-QTOF	splash10-000x-0090000000-245aaffd0711e1434dd0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrichodermin 40V, Positive-QTOF	splash10-0596-6190000000-ce9dcdcfe902bd55ee9b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrichodermin 10V, Negative-QTOF	splash10-0007-0090000000-a7894183665121fad96c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrichodermin 20V, Negative-QTOF	splash10-0a4j-8090000000-c81e27de83898aaf7d30	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isotrichodermin 40V, Negative-QTOF	splash10-0a4i-9140000000-fb8a6ec5edeb6ebc224f	2021-09-24	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

FDB013280

KNApSAcK ID

C00012645

Chemspider ID

11399530

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14733836

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 ]
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Showing metabocard for Isotrichodermin (HMDB0034738)

MOL for HMDB0034738 (Isotrichodermin)

3D MOL for HMDB0034738 (Isotrichodermin)

3D SDF for HMDB0034738 (Isotrichodermin)

3D-SDF for HMDB0034738 (Isotrichodermin)

PDB for HMDB0034738 (Isotrichodermin)

3D PDB for HMDB0034738 (Isotrichodermin)

SMILES for HMDB0034738 (Isotrichodermin)

INCHI for HMDB0034738 (Isotrichodermin)

Structure for HMDB0034738 (Isotrichodermin)

3D Structure for HMDB0034738 (Isotrichodermin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra