MiMeDB: Showing metabocard for 3-o-acetylbotcineric acid (MMDBc0008296)

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:11:38 UTC

Update Date

2025-10-07 16:05:26 UTC

Metabolite ID

MMDBc0008296

Metabolite Identification

Common Name

3-o-acetylbotcineric acid

Description

3-O-acetylbotcineric acid is a secondary metabolite belonging to the class of organic acids. It is produced by the fungus Botrytis cinerea, a well-known plant pathogen. This compound has garnered attention in the field of phytochemistry due to its potential biological activities. Research indicates that 3-O-acetylbotcineric acid, alongside another metabolite, 2-epi-botcinin A, was isolated from Botrytis cinerea (PMID:17928694 ). In studies assessing antifungal properties, 3-O-acetylbotcineric acid demonstrated an MIC value of 100 microM against Magnaporthe grisea, a significant pathogen responsible for rice blast disease, indicating its potential role in plant defense mechanisms (PMID:17928694 ). The structural features of 3-O-acetylbotcineric acid, particularly the acetyl group, may contribute to its bioactivity, although further studies are necessary to elucidate its precise mechanisms of action and potential applications in agriculture or medicine. Overall, this metabolite represents an interesting subject for further exploration in the context of natural product chemistry and its implications for crop protection.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305152103112D          

 42 42  0  0  1  0            999 V2000
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8057    6.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    6.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    4.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5236    5.8685    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3683    6.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7111    5.7252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0539    5.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0862    5.4387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717    4.4613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8663    5.3798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808    6.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9933    6.5005    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    5.0933    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 13 12  2  0  0  0  0
 14  2  1  1  0  0  0
 15  3  1  6  0  0  0
 16  4  1  1  0  0  0
 17  5  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 20 16  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 15  1  0  0  0  0
 24  6  1  6  0  0  0
 24 21  1  0  0  0  0
 24 22  1  1  0  0  0
 25 17  2  0  0  0  0
 18 26  1  6  0  0  0
 27 19  2  0  0  0  0
 21 28  1  6  0  0  0
 29 23  2  0  0  0  0
 30 23  1  0  0  0  0
 31 17  1  0  0  0  0
 22 31  1  1  0  0  0
 32 19  1  0  0  0  0
 20 32  1  1  0  0  0
 33 16  1  0  0  0  0
 33 24  1  0  0  0  0
 34 12  1  0  0  0  0
 35 13  1  0  0  0  0
 14 36  1  6  0  0  0
 15 37  1  1  0  0  0
 16 38  1  6  0  0  0
 18 39  1  6  0  0  0
 20 40  1  1  0  0  0
 21 41  1  1  0  0  0
 22 42  1  1  0  0  0
M  END


  Mrv1652305152103112D          

 42 42  0  0  1  0            999 V2000
   -2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8057    6.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1620    6.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    4.8067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5236    5.8685    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0000    4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3683    6.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.1250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4289    4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7111    5.7252    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0539    5.2365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0862    5.4387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7717    4.4613    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8663    5.3798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1808    6.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9933    6.5005    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2414    5.0933    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 13 12  2  0  0  0  0
 14  2  1  1  0  0  0
 15  3  1  6  0  0  0
 16  4  1  1  0  0  0
 17  5  1  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 20 16  1  0  0  0  0
 21 14  1  0  0  0  0
 22 15  1  0  0  0  0
 23 15  1  0  0  0  0
 24  6  1  6  0  0  0
 24 21  1  0  0  0  0
 24 22  1  1  0  0  0
 25 17  2  0  0  0  0
 18 26  1  6  0  0  0
 27 19  2  0  0  0  0
 21 28  1  6  0  0  0
 29 23  2  0  0  0  0
 30 23  1  0  0  0  0
 31 17  1  0  0  0  0
 22 31  1  1  0  0  0
 32 19  1  0  0  0  0
 20 32  1  1  0  0  0
 33 16  1  0  0  0  0
 33 24  1  0  0  0  0
 34 12  1  0  0  0  0
 35 13  1  0  0  0  0
 14 36  1  6  0  0  0
 15 37  1  1  0  0  0
 16 38  1  6  0  0  0
 18 39  1  6  0  0  0
 20 40  1  1  0  0  0
 21 41  1  1  0  0  0
 22 42  1  1  0  0  0
M  END
> <DATABASE_ID>
MMDBc0008296

> <DATABASE_NAME>
MIME

> <SMILES>
[H]C(=C([H])[C@@]([H])(O)CCCCCC)C(=O)O[C@@]1([H])[C@]([H])(C)O[C@](C)([C@@]([H])(OC(C)=O)[C@@]([H])(C)C(O)=O)[C@@]([H])(O)[C@]1([H])C

> <INCHI_IDENTIFIER>
InChI=1S/C24H40O9/c1-7-8-9-10-11-18(26)12-13-19(27)32-20-14(2)21(28)24(6,33-16(20)4)22(31-17(5)25)15(3)23(29)30/h12-16,18,20-22,26,28H,7-11H2,1-6H3,(H,29,30)/b13-12+/t14-,15-,16+,18+,20-,21+,22+,24+/m1/s1

> <INCHI_KEY>
OEOZRSNZAPXESQ-XLWGWGPTSA-N

> <FORMULA>
C24H40O9

> <MOLECULAR_WEIGHT>
472.575

> <EXACT_MASS>
472.267232868

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
50.72541717061265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-3-(acetyloxy)-3-[(2S,3S,4S,5R,6S)-3-hydroxy-5-{[(2E,4S)-4-hydroxydec-2-enoyl]oxy}-2,4,6-trimethyloxan-2-yl]-2-methylpropanoic acid

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
3.3113171286666665

> <ALOGPS_LOGS>
-3.75

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.60792844343861

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.050060124663926

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8715617686902073

> <JCHEM_POLAR_SURFACE_AREA>
139.59

> <JCHEM_REFRACTIVITY>
120.04419999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.35e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3S)-3-(acetyloxy)-3-[(2S,3S,4S,5R,6S)-3-hydroxy-5-{[(2E,4S)-4-hydroxydec-2-enoyl]oxy}-2,4,6-trimethyloxan-2-yl]-2-methylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-MAY-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-MAY-21         0                                  
HETATM    1  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.237  12.402   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.302  12.779   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.184   8.973   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667   3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.711  10.955   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000   9.240   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.688  11.599   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.194  10.687   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -5.701   9.775   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.161  10.152   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.334   0.770   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -4.001   6.930   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -5.174   8.328   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -7.217  10.042   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -2.204  11.867   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -1.334  10.010   0.000  0.00  0.00           O+0
HETATM   34  H   UNK     0       1.334   2.310   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.000   6.160   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.667   6.160   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      -3.721  12.134   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.334   8.470   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.334   3.850   0.000  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.334   8.470   0.000  0.00  0.00           H+0
HETATM   41  H   UNK     0      -4.001   8.470   0.000  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.184   9.507   0.000  0.00  0.00           H+0
CONECT    1    7                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4   16                                                            
CONECT    5   17                                                            
CONECT    6   24                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   18                                                       
CONECT   12   13   18   34                                                  
CONECT   13   12   19   35                                                  
CONECT   14    2   20   21   36                                             
CONECT   15    3   22   23   37                                             
CONECT   16    4   20   33   38                                             
CONECT   17    5   25   31                                                  
CONECT   18   11   12   26   39                                             
CONECT   19   13   27   32                                                  
CONECT   20   14   16   32   40                                             
CONECT   21   14   24   28   41                                             
CONECT   22   15   24   31   42                                             
CONECT   23   15   29   30                                                  
CONECT   24    6   21   22   33                                             
CONECT   25   17                                                            
CONECT   26   18                                                            
CONECT   27   19                                                            
CONECT   28   21                                                            
CONECT   29   23                                                            
CONECT   30   23                                                            
CONECT   31   17   22                                                       
CONECT   32   19   20                                                       
CONECT   33   16   24                                                       
CONECT   34   12                                                            
CONECT   35   13                                                            
CONECT   36   14                                                            
CONECT   37   15                                                            
CONECT   38   16                                                            
CONECT   39   18                                                            
CONECT   40   20                                                            
CONECT   41   21                                                            
CONECT   42   22                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   84    0
END

Synonyms

Value	Source
3-O-Acetylbotcinerate	Generator

Molecular Formula

C₂₄H₄₀O₉

Average Mass

472.575

Monoisotopic Mass

472.267232868

IUPAC Name

(2R,3S)-3-(acetyloxy)-3-[(2S,3S,4S,5R,6S)-3-hydroxy-5-{[(2E,4S)-4-hydroxydec-2-enoyl]oxy}-2,4,6-trimethyloxan-2-yl]-2-methylpropanoic acid

Traditional Name

(2R,3S)-3-(acetyloxy)-3-[(2S,3S,4S,5R,6S)-3-hydroxy-5-{[(2E,4S)-4-hydroxydec-2-enoyl]oxy}-2,4,6-trimethyloxan-2-yl]-2-methylpropanoic acid

CAS Registry Number

Not Available

SMILES

[H]C(=C([H])[C@@]([H])(O)CCCCCC)C(=O)O[C@@]1([H])[C@]([H])(C)O[C@](C)([C@@]([H])(OC(C)=O)[C@@]([H])(C)C(O)=O)[C@@]([H])(O)[C@]1([H])C

InChI Identifier

InChI=1S/C24H40O9/c1-7-8-9-10-11-18(26)12-13-19(27)32-20-14(2)21(28)24(6,33-16(20)4)22(31-17(5)25)15(3)23(29)30/h12-16,18,20-22,26,28H,7-11H2,1-6H3,(H,29,30)/b13-12+/t14-,15-,16+,18+,20-,21+,22+,24+/m1/s1

InChI Key

OEOZRSNZAPXESQ-XLWGWGPTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Fatty alcohol
Tricarboxylic acid or derivatives
Fatty acid ester
Oxane
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Dialkyl ether
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organic oxygen compound
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.084 g/L	ALOGPS
logP	3.31	ALOGPS
logP	3.31	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	4.05	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	139.59 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	120.04 m³·mol⁻¹	ChemAxon
Polarizability	50.73 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-10	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-10	View Spectrum
MS	Mass Spectrum (Electron Ionization)	Not Available	2022-08-06	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	298.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	66.9
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	556.8
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	578.5
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	603.4
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	159.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	2594.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	172.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	374.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	394.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	110.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	147.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	155.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	11.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	184.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	113.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	423.5
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	1593.3
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	1108.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	3-o-acetylbotcineric acid_TMS_1	CCCCCC[C@@H](C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O)[C@@H](O)[C@@H]1C)O[Si](C)(C)C	standard non polar	2025-10-23	939.521
Gas Chromatography	3-o-acetylbotcineric acid_TMS_2	CCCCCC[C@H](O)C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1C	standard non polar	2025-10-23	1845.18
Gas Chromatography	3-o-acetylbotcineric acid_TMS_3	CCCCCC[C@H](O)C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1C	standard non polar	2025-10-23	1478.46
Gas Chromatography	3-o-acetylbotcineric acid_TMS_4	CCCCCC[C@@H](C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1C)O[Si](C)(C)C	standard non polar	2025-10-23	1405.9
Gas Chromatography	3-o-acetylbotcineric acid_TMS_5	CCCCCC[C@@H](C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1C)O[Si](C)(C)C	standard non polar	2025-10-23	2679.93
Gas Chromatography	3-o-acetylbotcineric acid_TMS_6	CCCCCC[C@H](O)C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1C	standard non polar	2025-10-23	1936.19
Gas Chromatography	3-o-acetylbotcineric acid_TMS_7	CCCCCC[C@@H](C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1C)O[Si](C)(C)C	standard non polar	2025-10-23	3221.97
Gas Chromatography	3-o-acetylbotcineric acid_TMS_1	CCCCCC[C@@H](C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O)[C@@H](O)[C@@H]1C)O[Si](C)(C)C	standard polar	2025-10-23	1844.16
Gas Chromatography	3-o-acetylbotcineric acid_TMS_2	CCCCCC[C@H](O)C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1C	standard polar	2025-10-23	894.975
Gas Chromatography	3-o-acetylbotcineric acid_TMS_3	CCCCCC[C@H](O)C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1C	standard polar	2025-10-23	1578.46
Gas Chromatography	3-o-acetylbotcineric acid_TMS_4	CCCCCC[C@@H](C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O[Si](C)(C)C)[C@@H](O)[C@@H]1C)O[Si](C)(C)C	standard polar	2025-10-23	2301.08
Gas Chromatography	3-o-acetylbotcineric acid_TMS_5	CCCCCC[C@@H](C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O)[C@@H](O[Si](C)(C)C)[C@@H]1C)O[Si](C)(C)C	standard polar	2025-10-23	1828.81
Gas Chromatography	3-o-acetylbotcineric acid_TMS_6	CCCCCC[C@H](O)C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1C	standard polar	2025-10-23	1611.71
Gas Chromatography	3-o-acetylbotcineric acid_TMS_7	CCCCCC[C@@H](C=CC(=O)O[C@H]1[C@H](C)O[C@](C)([C@@H](OC(C)=O)[C@@H](C)C(=O)O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1C)O[Si](C)(C)C	standard polar	2025-10-23	2582.34

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78437166

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101437998

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 3-o-acetylbotcineric acid (MMDBc0008296)

MOL for #<Metabolite:0x00007f9af3fa34e0>

3D MOL for #<Metabolite:0x00007f9af3fa34e0>

3D SDF for #<Metabolite:0x00007f9af3fa34e0>

3D-SDF for #<Metabolite:0x00007f9af3fa34e0>

PDB for #<Metabolite:0x00007f9af3fa34e0>

3D PDB for #<Metabolite:0x00007f9af3fa34e0>

SMILES for #<Metabolite:0x00007f9af3fa34e0>

INCHI for #<Metabolite:0x00007f9af3fa34e0>

Structure for #<Metabolite:0x00007f9af3fa34e0>

3D Structure for #<Metabolite:0x00007f9af3fa34e0>