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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:50:36 UTC

Update Date

2022-03-07 02:54:16 UTC

HMDB ID

HMDB0034915

Secondary Accession Numbers

HMDB34915

Metabolite Identification

Common Name

Calonectrin

Description

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

Structure

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

HMDB0034915
     RDKit          3D
Calonectrin
 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.5007   -1.4283    1.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5925   -1.2137    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1260   -0.6732   -0.2054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3034   -1.5675    0.7744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -1.5084   -0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968   -0.2763   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    0.6673   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1120    1.7501   -0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9417    1.6852    1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9665    2.3268    1.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9073    1.0748    1.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986    0.4448    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8898    1.4728    0.1669 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135    1.1016   -0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -0.1248   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182   -0.0427    1.0129 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3565   -0.0477    1.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8441    0.0389    2.7527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -0.1279    0.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6763   -1.2683   -0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5451   -0.7126   -1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0846   -1.6999   -2.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2195    0.4885   -2.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2471    0.3369   -3.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0429    1.0718   -3.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1778   -0.5725    2.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8415   -1.5521    2.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0732   -2.3510    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5181   -2.3044    0.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833   -2.0275   -1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538    0.1005   -1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9261    1.1987   -2.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6808    2.7493   -0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2063    1.8747   -0.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6374    3.3993    2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752    2.2933    1.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8982    1.8975    2.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    1.0420    2.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015   -0.2244    1.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4584    1.9444   -1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4606   -0.1907   -1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0096   -0.9611    3.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8201    0.5641    2.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724    0.6795    3.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920   -2.0120   -1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3959   -1.8367    0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7937   -1.7690   -3.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0823   -2.7081   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9040   -1.4297   -2.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585    0.9975   -3.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3788   -0.5694   -3.6814 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
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 12  6  1  0
 23 14  1  0
 21  6  1  0
 25 23  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 24 50  1  0
 24 51  1  0
M  END


  Mrv0541 05061308082D          

 25 28  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
    2.4787    2.2701    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
    1.0212    0.2979    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
    0.7989   -1.2953    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
   -0.2939    0.1073    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
    1.9501    1.6367    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
    1.1194   -0.5867    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
    0.4999   -0.1173    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1372    1.7778    0.0000 O   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
    2.2343    0.8623    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2975    0.6825    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
    1.4934   -0.8715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 11  1  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  2  0  0  0  0
 12  2  1  0  0  0  0
 13  3  1  0  0  0  0
 14  8  1  0  0  0  0
 15  7  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  0  0  0  0
 17  8  1  0  0  0  0
 18  6  1  0  0  0  0
 18  9  1  0  0  0  0
 18 15  1  0  0  0  0
 18 17  1  0  0  0  0
 19 10  1  0  0  0  0
 19 16  1  0  0  0  0
 19 17  1  0  0  0  0
 20 12  2  0  0  0  0
 21 13  2  0  0  0  0
 22  9  1  0  0  0  0
 22 12  1  0  0  0  0
 23 10  1  0  0  0  0
 23 19  1  0  0  0  0
 24 13  1  0  0  0  0
 24 14  1  0  0  0  0
 25 15  1  0  0  0  0
 25 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034915

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)OCC12CCC(C)=CC1OC1C(CC2(C)C11CO1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O6/c1-11-5-6-18(9-22-12(2)20)15(7-11)25-16-14(24-13(3)21)8-17(18,4)19(16)10-23-19/h7,14-16H,5-6,8-10H2,1-4H3

> <INCHI_KEY>
IGDIDZAQDRAJRB-UHFFFAOYSA-N

> <FORMULA>
C19H26O6

> <MOLECULAR_WEIGHT>
350.4061

> <EXACT_MASS>
350.172938564

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
36.56895474380029

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
1.295995752333333

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.930401673270809

> <JCHEM_POLAR_SURFACE_AREA>
74.36000000000001

> <JCHEM_REFRACTIVITY>
87.89219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034915
     RDKit          3D
Calonectrin
 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.5007   -1.4283    1.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5925   -1.2137    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1260   -0.6732   -0.2054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3034   -1.5675    0.7744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -1.5084   -0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968   -0.2763   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    0.6673   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1120    1.7501   -0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9417    1.6852    1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9665    2.3268    1.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9073    1.0748    1.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986    0.4448    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8898    1.4728    0.1669 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135    1.1016   -0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -0.1248   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182   -0.0427    1.0129 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3565   -0.0477    1.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8441    0.0389    2.7527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -0.1279    0.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6763   -1.2683   -0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5451   -0.7126   -1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0846   -1.6999   -2.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2195    0.4885   -2.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2471    0.3369   -3.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0429    1.0718   -3.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1778   -0.5725    2.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8415   -1.5521    2.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0732   -2.3510    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5181   -2.3044    0.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833   -2.0275   -1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538    0.1005   -1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9261    1.1987   -2.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6808    2.7493   -0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2063    1.8747   -0.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6374    3.3993    2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752    2.2933    1.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8982    1.8975    2.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    1.0420    2.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015   -0.2244    1.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4584    1.9444   -1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4606   -0.1907   -1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0096   -0.9611    3.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8201    0.5641    2.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724    0.6795    3.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920   -2.0120   -1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3959   -1.8367    0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7937   -1.7690   -3.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0823   -2.7081   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9040   -1.4297   -2.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585    0.9975   -3.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3788   -0.5694   -3.6814 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
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 12  6  1  0
 23 14  1  0
 21  6  1  0
 25 23  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 24 50  1  0
 24 51  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       4.627   4.238   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.894  -6.072   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.906   0.556   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.345  -0.574   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       5.415  -3.074   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.491  -2.418   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.184   0.427   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.549   0.200   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.601  -2.092   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.640   3.055   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.575  -5.611   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.223  -3.066   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.971  -2.537   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.194  -1.737   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.090  -1.095   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.715  -1.018   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.933  -0.219   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.123   3.319   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.709  -6.653   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.171   1.610   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.555   1.274   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.911  -4.108   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.788  -1.627   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   17                                                            
CONECT    5    6   11                                                       
CONECT    6    5   18                                                       
CONECT    7   11   15                                                       
CONECT    8   14   17                                                       
CONECT    9   18   22                                                       
CONECT   10   19   23                                                       
CONECT   11    1    5    7                                                  
CONECT   12    2   20   22                                                  
CONECT   13    3   21   24                                                  
CONECT   14    8   16   24                                                  
CONECT   15    7   18   25                                                  
CONECT   16   14   19   25                                                  
CONECT   17    4    8   18   19                                             
CONECT   18    6    9   15   17                                             
CONECT   19   10   16   17   23                                             
CONECT   20   12                                                            
CONECT   21   13                                                            
CONECT   22    9   12                                                       
CONECT   23   10   19                                                       
CONECT   24   13   14                                                       
CONECT   25   15   16                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0034915
HETATM    1  C1  UNL     1      -4.501  -1.428   1.986  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.593  -1.214   0.792  1.00  0.00           C  
HETATM    3  O1  UNL     1      -4.126  -0.673  -0.205  1.00  0.00           O  
HETATM    4  O2  UNL     1      -2.303  -1.568   0.774  1.00  0.00           O  
HETATM    5  C3  UNL     1      -1.272  -1.508  -0.077  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.597  -0.276  -0.514  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.479   0.667  -1.236  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.112   1.750  -0.441  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.942   1.685   1.012  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.967   2.327   1.904  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.907   1.075   1.540  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.099   0.445   0.641  1.00  0.00           C  
HETATM   13  O3  UNL     1       0.890   1.473   0.167  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.813   1.102  -0.767  1.00  0.00           C  
HETATM   15  C12 UNL     1       2.624  -0.125  -0.313  1.00  0.00           C  
HETATM   16  O4  UNL     1       3.018  -0.043   1.013  1.00  0.00           O  
HETATM   17  C13 UNL     1       4.356  -0.048   1.333  1.00  0.00           C  
HETATM   18  C14 UNL     1       4.844   0.039   2.753  1.00  0.00           C  
HETATM   19  O5  UNL     1       5.195  -0.128   0.400  1.00  0.00           O  
HETATM   20  C15 UNL     1       1.676  -1.268  -0.608  1.00  0.00           C  
HETATM   21  C16 UNL     1       0.545  -0.713  -1.446  1.00  0.00           C  
HETATM   22  C17 UNL     1       0.085  -1.700  -2.472  1.00  0.00           C  
HETATM   23  C18 UNL     1       1.220   0.489  -2.015  1.00  0.00           C  
HETATM   24  C19 UNL     1       2.247   0.337  -3.101  1.00  0.00           C  
HETATM   25  O6  UNL     1       1.043   1.072  -3.190  1.00  0.00           O  
HETATM   26  H1  UNL     1      -5.178  -0.573   2.046  1.00  0.00           H  
HETATM   27  H2  UNL     1      -3.842  -1.552   2.872  1.00  0.00           H  
HETATM   28  H3  UNL     1      -5.073  -2.351   1.760  1.00  0.00           H  
HETATM   29  H4  UNL     1      -0.518  -2.304   0.272  1.00  0.00           H  
HETATM   30  H5  UNL     1      -1.583  -2.028  -1.081  1.00  0.00           H  
HETATM   31  H6  UNL     1      -2.254   0.100  -1.791  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.926   1.199  -2.075  1.00  0.00           H  
HETATM   33  H8  UNL     1      -1.681   2.749  -0.754  1.00  0.00           H  
HETATM   34  H9  UNL     1      -3.206   1.875  -0.675  1.00  0.00           H  
HETATM   35  H10 UNL     1      -2.637   3.399   2.013  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.975   2.293   1.474  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.898   1.898   2.921  1.00  0.00           H  
HETATM   38  H13 UNL     1      -0.806   1.042   2.633  1.00  0.00           H  
HETATM   39  H14 UNL     1       0.701  -0.224   1.246  1.00  0.00           H  
HETATM   40  H15 UNL     1       2.458   1.944  -1.009  1.00  0.00           H  
HETATM   41  H16 UNL     1       3.461  -0.191  -1.036  1.00  0.00           H  
HETATM   42  H17 UNL     1       5.010  -0.961   3.190  1.00  0.00           H  
HETATM   43  H18 UNL     1       5.820   0.564   2.704  1.00  0.00           H  
HETATM   44  H19 UNL     1       4.172   0.679   3.359  1.00  0.00           H  
HETATM   45  H20 UNL     1       2.192  -2.012  -1.293  1.00  0.00           H  
HETATM   46  H21 UNL     1       1.396  -1.837   0.265  1.00  0.00           H  
HETATM   47  H22 UNL     1       0.794  -1.769  -3.319  1.00  0.00           H  
HETATM   48  H23 UNL     1       0.082  -2.708  -2.008  1.00  0.00           H  
HETATM   49  H24 UNL     1      -0.904  -1.430  -2.889  1.00  0.00           H  
HETATM   50  H25 UNL     1       3.158   0.997  -3.072  1.00  0.00           H  
HETATM   51  H26 UNL     1       2.379  -0.569  -3.681  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3    4
CONECT    4    5
CONECT    5    6   29   30
CONECT    6    7   12   21
CONECT    7    8   31   32
CONECT    8    9   33   34
CONECT    9   10   11   11
CONECT   10   35   36   37
CONECT   11   12   38
CONECT   12   13   39
CONECT   13   14
CONECT   14   15   23   40
CONECT   15   16   20   41
CONECT   16   17
CONECT   17   18   19   19
CONECT   18   42   43   44
CONECT   20   21   45   46
CONECT   21   22   23
CONECT   22   47   48   49
CONECT   23   24   25
CONECT   24   25   50   51
END

HMDB0034915
     RDKit          3D
Calonectrin
 51 54  0  0  0  0  0  0  0  0999 V2000
   -4.5007   -1.4283    1.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5925   -1.2137    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1260   -0.6732   -0.2054 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3034   -1.5675    0.7744 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717   -1.5084   -0.0773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968   -0.2763   -0.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792    0.6673   -1.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1120    1.7501   -0.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9417    1.6852    1.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9665    2.3268    1.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9073    1.0748    1.5402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0986    0.4448    0.6409 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8898    1.4728    0.1669 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8135    1.1016   -0.7672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6241   -0.1248   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182   -0.0427    1.0129 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3565   -0.0477    1.3327 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8441    0.0389    2.7527 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1955   -0.1279    0.3999 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6763   -1.2683   -0.6082 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5451   -0.7126   -1.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0846   -1.6999   -2.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2195    0.4885   -2.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2471    0.3369   -3.1015 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0429    1.0718   -3.1900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1778   -0.5725    2.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8415   -1.5521    2.8718 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0732   -2.3510    1.7596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5181   -2.3044    0.2723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5833   -2.0275   -1.0813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2538    0.1005   -1.7912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9261    1.1987   -2.0755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6808    2.7493   -0.7539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2063    1.8747   -0.6746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6374    3.3993    2.0132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9752    2.2933    1.4742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8982    1.8975    2.9209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8060    1.0420    2.6333 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015   -0.2244    1.2464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4584    1.9444   -1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4606   -0.1907   -1.0358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0096   -0.9611    3.1904 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8201    0.5641    2.7041 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724    0.6795    3.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920   -2.0120   -1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3959   -1.8367    0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7937   -1.7690   -3.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0823   -2.7081   -2.0085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9040   -1.4297   -2.8887 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1585    0.9975   -3.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3788   -0.5694   -3.6814 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
  9 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 24 25  1  0
 12  6  1  0
 23 14  1  0
 21  6  1  0
 25 23  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  5 29  1  0
  5 30  1  0
  7 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
 10 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 12 39  1  0
 14 40  1  0
 15 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 20 45  1  0
 20 46  1  0
 22 47  1  0
 22 48  1  0
 22 49  1  0
 24 50  1  0
 24 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Calonectrin	HMDB
(3-alpha)-12,13-Epoxytrichothec-9-ene-3,15-diol diacetate	HMDB
[10'-(Acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-yl]methyl acetic acid	Generator

Chemical Formula

C₁₉H₂₆O₆

Average Molecular Weight

350.4061

Monoisotopic Molecular Weight

350.172938564

IUPAC Name

10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate

Traditional Name

10'-(acetyloxy)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-2'-ylmethyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OCC12CCC(C)=CC1OC1C(CC2(C)C11CO1)OC(C)=O

InChI Identifier

InChI=1S/C19H26O6/c1-11-5-6-18(9-22-12(2)20)15(7-11)25-16-14(24-13(3)21)8-17(18,4)19(16)10-23-19/h7,14-16H,5-6,8-10H2,1-4H3

InChI Key

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

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0034915)

Cellular substructure

Extracellular (HMDB: HMDB0034915)
Cytoplasm (HMDB: HMDB0034915)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034915)

Source

Endogenous

Endogenous (HMDB: HMDB0034915)

Animal

Animal (HMDB: HMDB0034915)

Exogenous

Food

Food (HMDB: HMDB0034915)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0034915)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0034915)

Cellular process

Cell signaling (HMDB: HMDB0034915)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0034915)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0034915)

Nutrient

Nutrient (HMDB: HMDB0034915)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	83 - 85 °C	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	0.063 g/L	ALOGPS
logP	1.6	ALOGPS
logP	1.3	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	74.36 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	87.89 m³·mol⁻¹	ChemAxon
Polarizability	36.57 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]+	183.465	31661259
DarkChem	[M-H]-	177.134	31661259
DeepCCS	[M-2H]-	208.351	30932474
DeepCCS	[M+Na]+	183.578	30932474
AllCCS	[M+H]+	183.1	32859911
AllCCS	[M+H-H2O]+	180.4	32859911
AllCCS	[M+NH4]+	185.6	32859911
AllCCS	[M+Na]+	186.3	32859911
AllCCS	[M-H]-	187.5	32859911
AllCCS	[M+Na-2H]-	187.7	32859911
AllCCS	[M+HCOO]-	188.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Calonectrin	CC(=O)OCC12CCC(C)=CC1OC1C(CC2(C)C11CO1)OC(C)=O	3598.0	Standard polar	33892256
Calonectrin	CC(=O)OCC12CCC(C)=CC1OC1C(CC2(C)C11CO1)OC(C)=O	2221.6	Standard non polar	33892256
Calonectrin	CC(=O)OCC12CCC(C)=CC1OC1C(CC2(C)C11CO1)OC(C)=O	2392.1	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 - Calonectrin GC-MS (Non-derivatized) - 70eV, Positive	splash10-00no-5982000000-afa7bb31148659b03f39	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Calonectrin 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 - Calonectrin 10V, Positive-QTOF	splash10-0k96-1079000000-a854005a4ce642e7af7f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calonectrin 20V, Positive-QTOF	splash10-0006-1593000000-26cc5fd68f78e4b0df66	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calonectrin 40V, Positive-QTOF	splash10-0005-6491000000-0d6f8f4554ed3cbb98d6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calonectrin 10V, Negative-QTOF	splash10-052b-2019000000-d4eac27ff76c4bace7e6	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calonectrin 20V, Negative-QTOF	splash10-0a4i-9447000000-eb55ba2988e9f5da6c86	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calonectrin 40V, Negative-QTOF	splash10-052f-5900000000-f204688001cd628fa71e	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calonectrin 10V, Negative-QTOF	splash10-052b-1039000000-07759321ead4c2e7e99c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calonectrin 20V, Negative-QTOF	splash10-0a4i-9031000000-24f6b3d0dcfc50a41eeb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calonectrin 40V, Negative-QTOF	splash10-0a4i-9234000000-eefbcfe8f80e34bb4e85	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calonectrin 10V, Positive-QTOF	splash10-0006-0092000000-504de686a60a99b20714	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calonectrin 20V, Positive-QTOF	splash10-000f-1091000000-65cda9f72013c23ae7dd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Calonectrin 40V, Positive-QTOF	splash10-002f-9272000000-83d0f62e0515f2eaf7fe	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

FDB013498

KNApSAcK ID

C00012631

Chemspider ID

468927

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

538469

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 Calonectrin (HMDB0034915)

MOL for HMDB0034915 (Calonectrin)

3D MOL for HMDB0034915 (Calonectrin)

3D SDF for HMDB0034915 (Calonectrin)

3D-SDF for HMDB0034915 (Calonectrin)

PDB for HMDB0034915 (Calonectrin)

3D PDB for HMDB0034915 (Calonectrin)

SMILES for HMDB0034915 (Calonectrin)

INCHI for HMDB0034915 (Calonectrin)

Structure for HMDB0034915 (Calonectrin)

3D Structure for HMDB0034915 (Calonectrin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra