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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 06:34:37 UTC

Update Date

2021-09-24 06:34:37 UTC

HMDB ID

HMDB0304030

Secondary Accession Numbers

None

Metabolite Identification

Common Name

16alpha, 17-epoxy gibberellin A9

Description

16alpha, 17-epoxy gibberellin a9 is also known as 16α, 17-epoxy ga9. 16alpha, 17-epoxy gibberellin a9 is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 16alpha, 17-epoxy gibberellin a9 can be found in a number of food items such as mugwort, natal plum, radish, and prickly pear, which makes 16alpha, 17-epoxy gibberellin a9 a potential biomarker for the consumption of these food products.

Structure

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

  Mrv1533007131514082D          

 28 33  0  0  1  0            999 V2000
    2.6075   -1.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6772   -0.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6661    1.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8117    1.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8655   -0.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3549    0.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4872    0.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6828   -0.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1946    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1182    1.1601    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4550    1.0713    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3328   -0.2786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5695    0.0538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4870   -1.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6059   -0.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0456   -0.7451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9322    0.3224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3899    0.3412    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6558    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2659   -1.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8622   -1.6278    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.1404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9496   -0.2648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8774    0.7320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8659    1.5087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779    1.1308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5298   -0.4678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3916    0.1231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 13 12  1  0  0  0  0
 12 14  1  1  0  0  0
 16  1  1  1  0  0  0
 16  5  1  0  0  0  0
 16 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17  7  1  6  0  0  0
 17  8  1  0  0  0  0
 17 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18  8  1  0  0  0  0
 18  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  2  0  0  0  0
 21 14  1  0  0  0  0
 22 15  2  0  0  0  0
 23  9  1  0  0  0  0
 18 23  1  6  0  0  0
 24 15  1  0  0  0  0
 24 19  1  0  0  0  0
 10 25  1  6  0  0  0
 11 26  1  1  0  0  0
 12 27  1  6  0  0  0
 13 28  1  1  0  0  0
M  CHG  1  21  -1
M  END

HMDB0304030
     RDKit          3D
16alpha, 17-epoxy gibberellin A9
 47 52  0  0  0  0  0  0  0  0999 V2000
   -3.2488    2.2433   -0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6258    0.8971   -0.2027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2537   -0.0329    0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873   -1.4466    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5838   -1.6222    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0287   -0.6095   -0.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8350   -0.4823   -1.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9470    0.2961   -1.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0121    0.4729   -2.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864    0.8259   -0.2898 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2845    0.8130    0.8377 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0700    2.2155    1.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919    3.1834    0.4768 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101    2.5324    2.3272 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9254    0.0818    0.2559 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5956   -0.8499    1.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9192   -1.0889    0.4332 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5832   -1.8284   -0.8390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904   -1.9525   -1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4209   -0.6210   -1.0049 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3227    0.3213    0.1559 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6190    0.7858    0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0718    0.8419    1.3322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    1.0236   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3506    2.1347   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7896    3.0167   -0.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1826    2.5572    0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6492   -0.0157    1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2885    0.2032    1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6028   -1.5413   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612   -2.1793    0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2085   -1.5326    1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176   -2.6152   -0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092    1.5030   -1.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6328    0.3196    1.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8362   -0.3226    2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609   -1.8345    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5751   -1.6371    1.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -2.8243   -0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9863   -1.2142   -1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9872   -2.3148   -2.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208   -2.7240   -0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245   -0.0242   -1.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    1.7802   -0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4815    0.0955   -0.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0301    1.9735    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9955    1.1965   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
  8  2  1  0
 20 15  1  0
 21 23  1  1
 10  2  1  0
 15 24  1  6
 20  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
 10 34  1  6
 11 35  1  1
 16 36  1  0
 16 37  1  0
 17 38  1  1
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  6
 22 44  1  0
 22 45  1  0
 24 46  1  0
 24 47  1  0
M  CHG  1  14  -1
M  END

  Mrv1533007131514082D          

 28 33  0  0  1  0            999 V2000
    2.6075   -1.4442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6772   -0.2973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6661    1.8938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8117    1.8639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8655   -0.8365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3549    0.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4872    0.7639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6828   -0.1732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1946    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1182    1.1601    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4550    1.0713    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3328   -0.2786    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5695    0.0538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4870   -1.0891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6059   -0.0471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0456   -0.7451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9322    0.3224    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3899    0.3412    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6558    1.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2659   -1.3608    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8622   -1.6278    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.1404    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9496   -0.2648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8774    0.7320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8659    1.5087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2779    1.1308    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5298   -0.4678    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3916    0.1231    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  2  1  0  0  0  0
  6  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 13 12  1  0  0  0  0
 12 14  1  1  0  0  0
 16  1  1  1  0  0  0
 16  5  1  0  0  0  0
 16 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17  7  1  6  0  0  0
 17  8  1  0  0  0  0
 17 11  1  0  0  0  0
 17 12  1  0  0  0  0
 18  8  1  0  0  0  0
 18  9  1  0  0  0  0
 18 10  1  0  0  0  0
 19  6  1  0  0  0  0
 19 11  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  2  0  0  0  0
 21 14  1  0  0  0  0
 22 15  2  0  0  0  0
 23  9  1  0  0  0  0
 18 23  1  6  0  0  0
 24 15  1  0  0  0  0
 24 19  1  0  0  0  0
 10 25  1  6  0  0  0
 11 26  1  1  0  0  0
 12 27  1  6  0  0  0
 13 28  1  1  0  0  0
M  CHG  1  21  -1
M  END
> <DATABASE_ID>
HMDB0304030

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12C[C@@]3(C[C@]11CO1)[C@@]([H])(CC2)C12CCC[C@](C)(C(=O)O1)[C@@]2([H])[C@]3([H])C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O5/c1-16-5-2-6-19(24-15(16)22)11-4-3-10-7-17(11,8-18(10)9-23-18)12(13(16)19)14(20)21/h10-13H,2-9H2,1H3,(H,20,21)/p-1/t10-,11-,12-,13-,16+,17-,18+,19?/m1/s1

> <INCHI_KEY>
PXYCXLNQKAEBRB-XAGBHBTISA-M

> <FORMULA>
C19H23O5

> <MOLECULAR_WEIGHT>
331.389

> <EXACT_MASS>
331.155097421

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
34.30331540888692

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2'R,5'R,8'R,9'S,10'R,11'S)-11'-methyl-16'-oxo-15'-oxaspiro[oxirane-2,6'-pentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane]-9'-carboxylate

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
1.9383630439999993

> <ALOGPS_LOGS>
-3.71

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.225505659842585

> <JCHEM_PKA_STRONGEST_BASIC>
-4.204175914594416

> <JCHEM_POLAR_SURFACE_AREA>
78.96

> <JCHEM_REFRACTIVITY>
93.33859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2'R,5'R,8'R,9'S,10'R,11'S)-11'-methyl-16'-oxo-15'-oxaspiro[oxirane-2,6'-pentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane]-9'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0304030
     RDKit          3D
16alpha, 17-epoxy gibberellin A9
 47 52  0  0  0  0  0  0  0  0999 V2000
   -3.2488    2.2433   -0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6258    0.8971   -0.2027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2537   -0.0329    0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873   -1.4466    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5838   -1.6222    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0287   -0.6095   -0.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8350   -0.4823   -1.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9470    0.2961   -1.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0121    0.4729   -2.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864    0.8259   -0.2898 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2845    0.8130    0.8377 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0700    2.2155    1.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919    3.1834    0.4768 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101    2.5324    2.3272 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9254    0.0818    0.2559 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5956   -0.8499    1.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9192   -1.0889    0.4332 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5832   -1.8284   -0.8390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904   -1.9525   -1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4209   -0.6210   -1.0049 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3227    0.3213    0.1559 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6190    0.7858    0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0718    0.8419    1.3322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    1.0236   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3506    2.1347   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7896    3.0167   -0.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1826    2.5572    0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6492   -0.0157    1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2885    0.2032    1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6028   -1.5413   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612   -2.1793    0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2085   -1.5326    1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176   -2.6152   -0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092    1.5030   -1.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6328    0.3196    1.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8362   -0.3226    2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609   -1.8345    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5751   -1.6371    1.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -2.8243   -0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9863   -1.2142   -1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9872   -2.3148   -2.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208   -2.7240   -0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245   -0.0242   -1.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    1.7802   -0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4815    0.0955   -0.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0301    1.9735    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9955    1.1965   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
  8  2  1  0
 20 15  1  0
 21 23  1  1
 10  2  1  0
 15 24  1  6
 20  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
 10 34  1  6
 11 35  1  1
 16 36  1  0
 16 37  1  0
 17 38  1  1
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  6
 22 44  1  0
 22 45  1  0
 24 46  1  0
 24 47  1  0
M  CHG  1  14  -1
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       4.867  -2.696   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.731  -0.555   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.577   3.535   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.982   3.479   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.216  -1.561   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.129   1.059   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.243   1.426   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.608  -0.323   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.430   0.976   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.421   2.165   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.316   2.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.088  -0.520   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.663   0.101   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.376  -2.033   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.864  -0.088   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.685  -1.391   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.207   0.602   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      11.928   0.637   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.824   1.877   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.830  -2.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       7.209  -3.039   0.000  0.00  0.00           O-1
HETATM   22  O   UNK     0       3.334  -0.262   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      12.973  -0.494   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       5.371   1.366   0.000  0.00  0.00           O+0
HETATM   25  H   UNK     0      12.816   2.816   0.000  0.00  0.00           H+0
HETATM   26  H   UNK     0       9.852   2.111   0.000  0.00  0.00           H+0
HETATM   27  H   UNK     0       6.589  -0.873   0.000  0.00  0.00           H+0
HETATM   28  H   UNK     0       8.198   0.230   0.000  0.00  0.00           H+0
CONECT    1   16                                                            
CONECT    2    5    6                                                       
CONECT    3    4   10                                                       
CONECT    4    3   11                                                       
CONECT    5    2   16                                                       
CONECT    6    2   19                                                       
CONECT    7   10   17                                                       
CONECT    8   17   18                                                       
CONECT    9   18   23                                                       
CONECT   10    3    7   18   25                                             
CONECT   11    4   17   19   26                                             
CONECT   12   13   14   17   27                                             
CONECT   13   12   16   19   28                                             
CONECT   14   12   20   21                                                  
CONECT   15   16   22   24                                                  
CONECT   16    1    5   13   15                                             
CONECT   17    7    8   11   12                                             
CONECT   18    8    9   10   23                                             
CONECT   19    6   11   13   24                                             
CONECT   20   14                                                            
CONECT   21   14                                                            
CONECT   22   15                                                            
CONECT   23    9   18                                                       
CONECT   24   15   19                                                       
CONECT   25   10                                                            
CONECT   26   11                                                            
CONECT   27   12                                                            
CONECT   28   13                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   66    0
END

COMPND    HMDB0304030
HETATM    1  C1  UNL     1      -3.249   2.243  -0.083  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.626   0.897  -0.203  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.254  -0.033   0.803  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.087  -1.447   0.231  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.584  -1.622   0.120  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.029  -0.610  -0.843  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.835  -0.482  -1.966  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.947   0.296  -1.563  1.00  0.00           C  
HETATM    9  O2  UNL     1      -4.012   0.473  -2.194  1.00  0.00           O  
HETATM   10  C8  UNL     1      -1.186   0.826  -0.290  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.285   0.813   0.838  1.00  0.00           C  
HETATM   12  C10 UNL     1       0.070   2.215   1.196  1.00  0.00           C  
HETATM   13  O3  UNL     1      -0.292   3.183   0.477  1.00  0.00           O  
HETATM   14  O4  UNL     1       0.810   2.532   2.327  1.00  0.00           O1-
HETATM   15  C11 UNL     1       0.925   0.082   0.256  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.596  -0.850   1.186  1.00  0.00           C  
HETATM   17  C13 UNL     1       2.919  -1.089   0.433  1.00  0.00           C  
HETATM   18  C14 UNL     1       2.583  -1.828  -0.839  1.00  0.00           C  
HETATM   19  C15 UNL     1       1.090  -1.952  -1.070  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.421  -0.621  -1.005  1.00  0.00           C  
HETATM   21  C17 UNL     1       3.323   0.321   0.156  1.00  0.00           C  
HETATM   22  C18 UNL     1       4.619   0.786   0.065  1.00  0.00           C  
HETATM   23  O5  UNL     1       4.072   0.842   1.332  1.00  0.00           O  
HETATM   24  C19 UNL     1       2.041   1.024  -0.129  1.00  0.00           C  
HETATM   25  H1  UNL     1      -4.351   2.135  -0.281  1.00  0.00           H  
HETATM   26  H2  UNL     1      -2.790   3.017  -0.716  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.183   2.557   0.983  1.00  0.00           H  
HETATM   28  H4  UNL     1      -2.649  -0.016   1.741  1.00  0.00           H  
HETATM   29  H5  UNL     1      -4.288   0.203   1.031  1.00  0.00           H  
HETATM   30  H6  UNL     1      -3.603  -1.541  -0.731  1.00  0.00           H  
HETATM   31  H7  UNL     1      -3.461  -2.179   0.983  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.209  -1.533   1.146  1.00  0.00           H  
HETATM   33  H9  UNL     1      -1.418  -2.615  -0.329  1.00  0.00           H  
HETATM   34  H10 UNL     1      -0.809   1.503  -1.080  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.633   0.320   1.764  1.00  0.00           H  
HETATM   36  H12 UNL     1       1.836  -0.323   2.121  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.161  -1.834   1.312  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.575  -1.637   1.108  1.00  0.00           H  
HETATM   39  H15 UNL     1       3.059  -2.824  -0.885  1.00  0.00           H  
HETATM   40  H16 UNL     1       2.986  -1.214  -1.686  1.00  0.00           H  
HETATM   41  H17 UNL     1       0.987  -2.315  -2.136  1.00  0.00           H  
HETATM   42  H18 UNL     1       0.621  -2.724  -0.442  1.00  0.00           H  
HETATM   43  H19 UNL     1       0.724  -0.024  -1.868  1.00  0.00           H  
HETATM   44  H20 UNL     1       4.852   1.780  -0.417  1.00  0.00           H  
HETATM   45  H21 UNL     1       5.481   0.095  -0.028  1.00  0.00           H  
HETATM   46  H22 UNL     1       2.030   1.973   0.417  1.00  0.00           H  
HETATM   47  H23 UNL     1       1.995   1.196  -1.244  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3    8   10
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7   10   20
CONECT    7    8
CONECT    8    9    9
CONECT   10   11   34
CONECT   11   12   15   35
CONECT   12   13   13   14
CONECT   15   16   20   24
CONECT   16   17   36   37
CONECT   17   18   21   38
CONECT   18   19   39   40
CONECT   19   20   41   42
CONECT   20   43
CONECT   21   22   23   24
CONECT   22   23   44   45
CONECT   24   46   47
END

HMDB0304030
     RDKit          3D
16alpha, 17-epoxy gibberellin A9
 47 52  0  0  0  0  0  0  0  0999 V2000
   -3.2488    2.2433   -0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6258    0.8971   -0.2027 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2537   -0.0329    0.8031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0873   -1.4466    0.2310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5838   -1.6222    0.1204 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0287   -0.6095   -0.8427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8350   -0.4823   -1.9658 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9470    0.2961   -1.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0121    0.4729   -2.1944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1864    0.8259   -0.2898 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2845    0.8130    0.8377 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0700    2.2155    1.1955 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2919    3.1834    0.4768 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8101    2.5324    2.3272 O   0  0  0  0  0  1  0  0  0  0  0  0
    0.9254    0.0818    0.2559 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5956   -0.8499    1.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9192   -1.0889    0.4332 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5832   -1.8284   -0.8390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0904   -1.9525   -1.0702 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4209   -0.6210   -1.0049 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3227    0.3213    0.1559 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.6190    0.7858    0.0647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0718    0.8419    1.3322 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    1.0236   -0.1289 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3506    2.1347   -0.2805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7896    3.0167   -0.7155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1826    2.5572    0.9835 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6492   -0.0157    1.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2885    0.2032    1.0314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6028   -1.5413   -0.7306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4612   -2.1793    0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2085   -1.5326    1.1459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4176   -2.6152   -0.3295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8092    1.5030   -1.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6328    0.3196    1.7641 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8362   -0.3226    2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1609   -1.8345    1.3120 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5751   -1.6371    1.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0589   -2.8243   -0.8849 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9863   -1.2142   -1.6861 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9872   -2.3148   -2.1358 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6208   -2.7240   -0.4416 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7245   -0.0242   -1.8682 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8518    1.7802   -0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4815    0.0955   -0.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0301    1.9735    0.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9955    1.1965   -1.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 11 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 17 21  1  0
 21 22  1  0
 22 23  1  0
 21 24  1  0
  8  2  1  0
 20 15  1  0
 21 23  1  1
 10  2  1  0
 15 24  1  6
 20  6  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
 10 34  1  6
 11 35  1  1
 16 36  1  0
 16 37  1  0
 17 38  1  1
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  6
 22 44  1  0
 22 45  1  0
 24 46  1  0
 24 47  1  0
M  CHG  1  14  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
16a, 17-Epoxy gibberellin a9	Generator
16Α, 17-epoxy gibberellin a9	Generator
16α, 17-epoxy ga9	HMDB

Chemical Formula

C₁₉H₂₃O₅

Average Molecular Weight

331.389

Monoisotopic Molecular Weight

331.155097421

IUPAC Name

(2R,2'R,5'R,8'R,9'S,10'R,11'S)-11'-methyl-16'-oxo-15'-oxaspiro[oxirane-2,6'-pentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane]-9'-carboxylate

Traditional Name

(2R,2'R,5'R,8'R,9'S,10'R,11'S)-11'-methyl-16'-oxo-15'-oxaspiro[oxirane-2,6'-pentacyclo[9.3.2.1⁵,⁸.0¹,¹⁰.0²,⁸]heptadecane]-9'-carboxylate

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@]3(C[C@]11CO1)[C@@]([H])(CC2)C12CCC[C@](C)(C(=O)O1)[C@@]2([H])[C@]3([H])C([O-])=O

InChI Identifier

InChI=1S/C19H24O5/c1-16-5-2-6-19(24-15(16)22)11-4-3-10-7-17(11,8-18(10)9-23-18)12(13(16)19)14(20)21/h10-13H,2-9H2,1H3,(H,20,21)/p-1/t10-,11-,12-,13-,16+,17-,18+,19?/m1/s1

InChI Key

PXYCXLNQKAEBRB-XAGBHBTISA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c19-gibberellin 6-carboxylic acids. These are c19-gibberellins with a carboxyl group at the 6-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

C19-gibberellin 6-carboxylic acids

Alternative Parents

Substituents

20-norgibberellane-6-carboxylic acid
Diterpene lactone
Caprolactone
Oxepane
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxacycle
Oxirane
Ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Organic anion
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

Not Available

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	2.43	ALOGPS
logP	1.94	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	4.23	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.96 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	93.34 m³·mol⁻¹	ChemAxon
Polarizability	34.3 Å³	ChemAxon
Number of Rings	6	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
AllCCS	[M+H]+	175.587	32859911
AllCCS	[M+H-H2O]+	172.817	32859911
AllCCS	[M+Na]+	178.878	32859911
AllCCS	[M+NH4]+	178.145	32859911
AllCCS	[M-H]-	182.473	32859911
AllCCS	[M+Na-2H]-	181.84	32859911
AllCCS	[M+HCOO]-	181.285	32859911
DeepCCS	[M-2H]-	197.304	30932474
DeepCCS	[M+Na]+	171.946	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16alpha, 17-epoxy gibberellin A9 10V, Negative-QTOF	splash10-0019-0098000000-8a2312d909aedee0a577	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16alpha, 17-epoxy gibberellin A9 20V, Negative-QTOF	splash10-000i-0092000000-0080ecd8722dd7dc228c	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 16alpha, 17-epoxy gibberellin A9 40V, Negative-QTOF	splash10-000f-0090000000-874d08c8d92f5e2aff00	2019-02-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB030275

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46173298

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

Not Available

Showing metabocard for 16alpha, 17-epoxy gibberellin A9 (HMDB0304030)

MOL for HMDB0304030 (16alpha, 17-epoxy gibberellin A9)

3D MOL for HMDB0304030 (16alpha, 17-epoxy gibberellin A9)

3D SDF for HMDB0304030 (16alpha, 17-epoxy gibberellin A9)

3D-SDF for HMDB0304030 (16alpha, 17-epoxy gibberellin A9)

PDB for HMDB0304030 (16alpha, 17-epoxy gibberellin A9)

3D PDB for HMDB0304030 (16alpha, 17-epoxy gibberellin A9)

SMILES for HMDB0304030 (16alpha, 17-epoxy gibberellin A9)

INCHI for HMDB0304030 (16alpha, 17-epoxy gibberellin A9)

Structure for HMDB0304030 (16alpha, 17-epoxy gibberellin A9)

3D Structure for HMDB0304030 (16alpha, 17-epoxy gibberellin A9)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra