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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 21:39:16 UTC

Update Date

2021-09-26 23:16:34 UTC

HMDB ID

HMDB0259176

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Trichoderonin

Description

Trichodermin 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. Trichodermin is an extremely weak basic (essentially neutral) compound (based on its pKa). Trichodermin is a potentially toxic compound. This compound has been identified in human blood as reported by (PMID: 31557052 ). Trichoderonin is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Trichoderonin is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0259176
     RDKit          3D
Trichoderonin
 45 48  0  0  0  0  0  0  0  0999 V2000
   -2.7718    2.9205    2.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8255    1.7462    1.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878    1.0617    1.0543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7301    1.3503    0.4104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8206    0.2487   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5954    0.5579   -1.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709   -0.4830   -2.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6794    0.0584   -2.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655    0.6021   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2908    0.9839   -0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926    0.8999    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3202    1.2964    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2199    0.4196    1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    0.0893    1.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -0.4402    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213   -1.6326   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8846   -0.8902   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3824   -1.7676    1.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8565   -1.6064   -1.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393   -2.9238   -1.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376   -2.1013   -1.7101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7067    3.8783    1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    2.8057    2.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7176    2.9719    2.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549   -0.2049   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5140    0.4061   -2.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    1.5664   -2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6852   -0.7110   -3.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    1.5302   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.3520   -1.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865    0.3744    0.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7437    1.6831   -0.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301    2.0499    1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632   -0.5268    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4160    1.1426    2.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1735    0.9855    1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5325   -0.7276    2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010   -2.0234   -1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2562   -2.4756    0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4883   -1.3965   -0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3604   -2.2095    0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5244   -1.1525    1.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6924   -2.6034    1.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1573   -3.6371   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9042   -3.4677   -2.5762 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
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 17  5  1  0
 21 19  1  0
 19  7  1  0
 15  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
  7 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
M  END


  Mrv0541 02241212312D          

 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
    3.5364   -1.1209    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
    2.1275   -1.3591    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
    2.6257   -0.0198    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
    1.0605   -0.5572    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
    0.1197   -1.6427    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
    0.4999   -0.1173    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
    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
    1.3576   -1.8128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1928   -2.6211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8104   -3.1681    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4103   -2.8825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8444    0.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7057    0.2288    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
  3  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
  2  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 14  1  0  0  0  0
 11 15  1  0  0  0  0
  4 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
  8 20  1  0  0  0  0
  5 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0259176

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OC1CC2OC3C=C(C)CCC3(C)C1(C)C21CO1

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

> <INCHI_KEY>
HNEGCRMUYSKRRR-UHFFFAOYSA-N

> <FORMULA>
C17H24O4

> <MOLECULAR_WEIGHT>
292.3701

> <EXACT_MASS>
292.167459256

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.6359718282186

> <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-11'-yl acetate

> <ALOGPS_LOGP>
2.15

> <JCHEM_LOGP>
1.9069400326666648

> <ALOGPS_LOGS>
-3.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9215609741474178

> <JCHEM_POLAR_SURFACE_AREA>
48.06

> <JCHEM_REFRACTIVITY>
77.0764

> <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-11'-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0259176
     RDKit          3D
Trichoderonin
 45 48  0  0  0  0  0  0  0  0999 V2000
   -2.7718    2.9205    2.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8255    1.7462    1.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878    1.0617    1.0543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7301    1.3503    0.4104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8206    0.2487   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5954    0.5579   -1.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709   -0.4830   -2.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6794    0.0584   -2.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655    0.6021   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2908    0.9839   -0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926    0.8999    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3202    1.2964    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2199    0.4196    1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    0.0893    1.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -0.4402    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213   -1.6326   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8846   -0.8902   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3824   -1.7676    1.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8565   -1.6064   -1.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393   -2.9238   -1.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376   -2.1013   -1.7101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7067    3.8783    1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    2.8057    2.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7176    2.9719    2.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549   -0.2049   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5140    0.4061   -2.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    1.5664   -2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6852   -0.7110   -3.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    1.5302   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.3520   -1.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865    0.3744    0.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7437    1.6831   -0.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301    2.0499    1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632   -0.5268    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4160    1.1426    2.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1735    0.9855    1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5325   -0.7276    2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010   -2.0234   -1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2562   -2.4756    0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4883   -1.3965   -0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3604   -2.2095    0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5244   -1.1525    1.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6924   -2.6034    1.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1573   -3.6371   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9042   -3.4677   -2.5762 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
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 17  5  1  0
 21 19  1  0
 19  7  1  0
 15  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
  7 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 42  1  0
 18 43  1  0
 20 44  1  0
 20 45  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       8.045  -2.629   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.601  -2.092   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.415  -3.074   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.715  -1.018   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.901  -0.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.345  -0.574   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.980  -1.040   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.381  -2.363   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       1.194  -1.737   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.933  -0.219   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.390   0.570   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       0.955   1.321   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.008  -1.737   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.534  -3.384   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.227  -4.893   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.379  -5.914   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       0.766  -5.381   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.576   0.446   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.184   0.427   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   15                                                  
CONECT    5    4    6    8   21                                             
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    5    9   12   20                                             
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   15                                                  
CONECT   12   11    8   13   14                                             
CONECT   13   12   14                                                       
CONECT   14   13   12                                                       
CONECT   15   11    4                                                       
CONECT   16    9   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20    8                                                            
CONECT   21    5                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   48    0
END

COMPND    HMDB0259176
HETATM    1  C1  UNL     1      -2.772   2.921   2.086  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.825   1.746   1.170  1.00  0.00           C  
HETATM    3  O1  UNL     1      -3.888   1.062   1.054  1.00  0.00           O  
HETATM    4  O2  UNL     1      -1.730   1.350   0.410  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.821   0.249  -0.432  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.595   0.558  -1.893  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.571  -0.483  -2.370  1.00  0.00           C  
HETATM    8  O3  UNL     1       0.679   0.058  -2.169  1.00  0.00           O  
HETATM    9  C6  UNL     1       0.865   0.602  -0.923  1.00  0.00           C  
HETATM   10  C7  UNL     1       2.291   0.984  -0.734  1.00  0.00           C  
HETATM   11  C8  UNL     1       2.893   0.900   0.447  1.00  0.00           C  
HETATM   12  C9  UNL     1       4.320   1.296   0.576  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.220   0.420   1.684  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.778   0.089   1.508  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.543  -0.440   0.138  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.421  -1.633  -0.152  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.885  -0.890  -0.093  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.382  -1.768   1.005  1.00  0.00           C  
HETATM   19  C16 UNL     1      -0.856  -1.606  -1.450  1.00  0.00           C  
HETATM   20  C17 UNL     1      -1.139  -2.924  -1.640  1.00  0.00           C  
HETATM   21  O4  UNL     1      -2.238  -2.101  -1.710  1.00  0.00           O  
HETATM   22  H1  UNL     1      -2.707   3.878   1.496  1.00  0.00           H  
HETATM   23  H2  UNL     1      -1.914   2.806   2.771  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.718   2.972   2.637  1.00  0.00           H  
HETATM   25  H4  UNL     1      -2.855  -0.205  -0.375  1.00  0.00           H  
HETATM   26  H5  UNL     1      -2.514   0.406  -2.514  1.00  0.00           H  
HETATM   27  H6  UNL     1      -1.241   1.566  -2.096  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.685  -0.711  -3.432  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.283   1.530  -0.750  1.00  0.00           H  
HETATM   30  H9  UNL     1       2.890   1.352  -1.586  1.00  0.00           H  
HETATM   31  H10 UNL     1       4.886   0.374   0.851  1.00  0.00           H  
HETATM   32  H11 UNL     1       4.744   1.683  -0.361  1.00  0.00           H  
HETATM   33  H12 UNL     1       4.430   2.050   1.407  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.763  -0.527   1.973  1.00  0.00           H  
HETATM   35  H14 UNL     1       2.416   1.143   2.502  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.173   0.985   1.705  1.00  0.00           H  
HETATM   37  H16 UNL     1       0.532  -0.728   2.231  1.00  0.00           H  
HETATM   38  H17 UNL     1       1.101  -2.023  -1.157  1.00  0.00           H  
HETATM   39  H18 UNL     1       1.256  -2.476   0.548  1.00  0.00           H  
HETATM   40  H19 UNL     1       2.488  -1.396  -0.271  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.360  -2.210   0.689  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.524  -1.153   1.900  1.00  0.00           H  
HETATM   43  H22 UNL     1      -0.692  -2.603   1.130  1.00  0.00           H  
HETATM   44  H23 UNL     1      -1.157  -3.637  -0.765  1.00  0.00           H  
HETATM   45  H24 UNL     1      -0.904  -3.468  -2.576  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   17   25
CONECT    6    7   26   27
CONECT    7    8   19   28
CONECT    8    9
CONECT    9   10   15   29
CONECT   10   11   11   30
CONECT   11   12   13
CONECT   12   31   32   33
CONECT   13   14   34   35
CONECT   14   15   36   37
CONECT   15   16   17
CONECT   16   38   39   40
CONECT   17   18   19
CONECT   18   41   42   43
CONECT   19   20   21
CONECT   20   21   44   45
END

HMDB0259176
     RDKit          3D
Trichoderonin
 45 48  0  0  0  0  0  0  0  0999 V2000
   -2.7718    2.9205    2.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8255    1.7462    1.1702 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8878    1.0617    1.0543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7301    1.3503    0.4104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8206    0.2487   -0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5954    0.5579   -1.8926 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5709   -0.4830   -2.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6794    0.0584   -2.1692 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8655    0.6021   -0.9231 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2908    0.9839   -0.7337 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926    0.8999    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3202    1.2964    0.5755 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2199    0.4196    1.6840 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7775    0.0893    1.5083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5430   -0.4402    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213   -1.6326   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8846   -0.8902   -0.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3824   -1.7676    1.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8565   -1.6064   -1.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1393   -2.9238   -1.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376   -2.1013   -1.7101 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7067    3.8783    1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9137    2.8057    2.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7176    2.9719    2.6369 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8549   -0.2049   -0.3752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5140    0.4061   -2.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2413    1.5664   -2.0955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6852   -0.7110   -3.4322 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    1.5302   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8900    1.3520   -1.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8865    0.3744    0.8505 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7437    1.6831   -0.3612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301    2.0499    1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7632   -0.5268    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4160    1.1426    2.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1735    0.9855    1.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5325   -0.7276    2.2307 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1010   -2.0234   -1.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2562   -2.4756    0.5477 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4883   -1.3965   -0.2707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3604   -2.2095    0.6887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5244   -1.1525    1.8998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6924   -2.6034    1.1303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1573   -3.6371   -0.7651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9042   -3.4677   -2.5762 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
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 17  5  1  0
 21 19  1  0
 19  7  1  0
 15  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
  7 28  1  0
  9 29  1  0
 10 30  1  0
 12 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 18 41  1  0
 18 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
Trichodermol	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-11'-yl acetate

Traditional Name

1',2',5'-trimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-11'-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2OC3C=C(C)CCC3(C)C1(C)C21CO1

InChI Identifier

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

InChI Key

HNEGCRMUYSKRRR-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

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Process

Not Available

Role

Not Available

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
logP	2.15	ALOGPS
logP	1.91	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	77.08 m³·mol⁻¹	ChemAxon
Polarizability	31.64 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
DeepCCS	[M-2H]-	201.602	30932474
DeepCCS	[M+Na]+	176.881	30932474
AllCCS	[M+H]+	170.9	32859911
AllCCS	[M+H-H2O]+	167.6	32859911
AllCCS	[M+NH4]+	173.9	32859911
AllCCS	[M+Na]+	174.7	32859911
AllCCS	[M-H]-	177.0	32859911
AllCCS	[M+Na-2H]-	177.0	32859911
AllCCS	[M+HCOO]-	177.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Trichoderonin	CC(=O)OC1CC2OC3C=C(C)CCC3(C)C1(C)C21CO1	2949.4	Standard polar	33892256
Trichoderonin	CC(=O)OC1CC2OC3C=C(C)CCC3(C)C1(C)C21CO1	1971.7	Standard non polar	33892256
Trichoderonin	CC(=O)OC1CC2OC3C=C(C)CCC3(C)C1(C)C21CO1	2062.7	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 - Trichoderonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2970000000-eed052e1ad5d601256a4	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Trichoderonin 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 - Trichoderonin 10V, Positive-QTOF	splash10-0006-0190000000-959ecccd584a31a018ac	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichoderonin 20V, Positive-QTOF	splash10-0a59-2950000000-7b831f76b824f29e5282	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichoderonin 40V, Positive-QTOF	splash10-0pvi-9720000000-8a7bb7f34bceff896be0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichoderonin 10V, Negative-QTOF	splash10-0006-0190000000-983bdfe9a78390587e4c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichoderonin 20V, Negative-QTOF	splash10-0005-2190000000-5d436f0311464454c2f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Trichoderonin 40V, Negative-QTOF	splash10-05i3-2900000000-e33a061318e1f56487ea	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Trichodermin

METLIN ID

Not Available

PubChem Compound

3704473

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Trichoderonin (HMDB0259176)

MOL for HMDB0259176 (Trichoderonin)

3D MOL for HMDB0259176 (Trichoderonin)

3D SDF for HMDB0259176 (Trichoderonin)

3D-SDF for HMDB0259176 (Trichoderonin)

PDB for HMDB0259176 (Trichoderonin)

3D PDB for HMDB0259176 (Trichoderonin)

SMILES for HMDB0259176 (Trichoderonin)

INCHI for HMDB0259176 (Trichoderonin)

Structure for HMDB0259176 (Trichoderonin)

3D Structure for HMDB0259176 (Trichoderonin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra