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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:04:57 UTC

Update Date

2022-03-07 02:55:06 UTC

HMDB ID

HMDB0036900

Secondary Accession Numbers

HMDB36900

Metabolite Identification

Common Name

Gibberellin A66

Description

Gibberellin A66 (GA66) belongs to the class of organic compounds known as C20-gibberellin 20-carboxylic acids. These are C20-gibberellins with a carboxyl group at the 6-position. Gibberellin A66 is found in fats and oils. Gibberellin A66 is isolated from seeds of Helianthus annuus (sunflower).

Structure

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

  Mrv1652307232019292D          

 29 32  0  0  0  0            999 V2000
   -1.3586    1.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1402   -0.4366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0860    1.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    1.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1399    2.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453    0.9016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8606    1.6044    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4438    0.1776    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9956    0.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6202    0.2269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7876    0.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1144    0.1187    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424    1.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6440    0.6432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3958   -1.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2031   -1.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553   -1.8345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3561    1.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728    1.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0731    0.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3587   -0.5938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8325   -1.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8748   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6445   -0.1817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0724   -0.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6454   -0.8942    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -1.1123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5754   -2.0063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566   -0.5857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10  3  1  6  0  0  0
  7  3  1  6  0  0  0
  9 11  2  0  0  0  0
  2 10  1  0  0  0  0
  6 12  1  1  0  0  0
 14 13  1  6  0  0  0
  1 14  1  0  0  0  0
 14  6  1  0  0  0  0
  2 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 19  2  0  0  0  0
 13 18  1  0  0  0  0
  1 20  1  0  0  0  0
 21 24  1  0  0  0  0
 25 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  6  0  0  0
 24 26  1  1  0  0  0
 20 25  1  0  0  0  0
 14 24  1  0  0  0  0
 24  2  1  0  0  0  0
 23 27  1  0  0  0  0
 23 28  2  0  0  0  0
  8 29  1  1  0  0  0
M  END

HMDB0036900
     RDKit          3D
Gibberellin A66
 53 56  0  0  0  0  0  0  0  0999 V2000
    4.5608    1.5547    0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522    0.8609    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3074   -0.5770    0.5967 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1002   -1.3937   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6586   -1.8123   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -0.6345   -0.8583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7011   -0.9331   -0.5956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9549   -2.1328    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -2.2808    1.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914   -3.3602   -0.4886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4829   -1.0936   -1.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066   -1.3561   -1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4855   -0.2009   -0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6011    0.4230    0.3461 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0695    1.8989    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679   -0.0501    1.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9914   -0.8087    1.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3080    0.2491    2.8423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1944    0.3763   -0.0590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1509    0.8196    0.8903 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0021    2.2948    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4089    2.9591   -0.1185 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6120    2.9538    1.9335 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1390    0.2359    0.3041 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9566   -0.4815    1.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0983    1.2981   -0.1804 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1508    1.2966   -1.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4968    1.1295    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5483    2.5988    0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0935   -0.9544    1.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7121   -2.3177   -0.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4573   -0.8073   -1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6320   -2.2358   -1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -2.5676   -0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.0671   -1.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3700   -3.4560   -1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -1.9318   -2.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392   -0.1241   -2.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9364   -2.2430   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -1.5221   -2.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641    0.5362   -1.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4033   -0.5612   -0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6883    2.4228    1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875    2.3672   -0.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1928    1.7826    0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8906   -0.4851    3.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066    1.0880   -0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2030    0.4178    1.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4751    3.9329    2.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718   -1.4898    1.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543    0.1995    2.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8870    2.3095    0.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9377    1.8726   -1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  1
 16 17  2  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  0
 26  2  1  0
 25  3  1  0
 24  6  1  0
 19  7  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  1
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  6
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 18 46  1  0
 19 47  1  6
 20 48  1  1
 23 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  1
 27 53  1  0
M  END

  Mrv1652307232019292D          

 29 32  0  0  0  0            999 V2000
   -1.3586    1.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1402   -0.4366    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0860    1.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    1.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1399    2.0063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1453    0.9016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8606    1.6044    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4438    0.1776    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9956    0.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6202    0.2269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7876    0.5593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1144    0.1187    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6424    1.4716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6440    0.6432    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3958   -1.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2031   -1.3917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1553   -1.8345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3561    1.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0728    1.8827    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0731    0.6432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3587   -0.5938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8325   -1.2276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8748   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6445   -0.1817    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0724   -0.1817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6454   -0.8942    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6903   -1.1123    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5754   -2.0063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566   -0.5857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  9  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10  3  1  6  0  0  0
  7  3  1  6  0  0  0
  9 11  2  0  0  0  0
  2 10  1  0  0  0  0
  6 12  1  1  0  0  0
 14 13  1  6  0  0  0
  1 14  1  0  0  0  0
 14  6  1  0  0  0  0
  2 15  1  1  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 13 19  2  0  0  0  0
 13 18  1  0  0  0  0
  1 20  1  0  0  0  0
 21 24  1  0  0  0  0
 25 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  1  6  0  0  0
 24 26  1  1  0  0  0
 20 25  1  0  0  0  0
 14 24  1  0  0  0  0
 24  2  1  0  0  0  0
 23 27  1  0  0  0  0
 23 28  2  0  0  0  0
  8 29  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0036900

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CC[C@@H]3C[C@]1([C@H](O)C3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O7/c1-9-10-4-5-11-19(17(26)27)7-3-6-18(2,16(24)25)13(19)12(15(22)23)20(11,8-10)14(9)21/h10-14,21H,1,3-8H2,2H3,(H,22,23)(H,24,25)(H,26,27)/t10-,11+,12-,13-,14-,18-,19-,20-/m1/s1

> <INCHI_KEY>
GYALTOSSVLCVLA-BPKUSKMISA-N

> <FORMULA>
C20H26O7

> <MOLECULAR_WEIGHT>
378.421

> <EXACT_MASS>
378.167853177

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
53

> <JCHEM_AVERAGE_POLARIZABILITY>
37.75223006931302

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,3R,4R,8R,9R,12R,14R)-14-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylic acid

> <ALOGPS_LOGP>
0.55

> <JCHEM_LOGP>
1.7027956046666672

> <ALOGPS_LOGS>
-2.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-3

> <JCHEM_PKA>
4.211034392956492

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6701926419193476

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1867865693011916

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
92.0812

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.23e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3R,4R,8R,9R,12R,14R)-14-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036900
     RDKit          3D
Gibberellin A66
 53 56  0  0  0  0  0  0  0  0999 V2000
    4.5608    1.5547    0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522    0.8609    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3074   -0.5770    0.5967 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1002   -1.3937   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6586   -1.8123   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -0.6345   -0.8583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7011   -0.9331   -0.5956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9549   -2.1328    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -2.2808    1.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914   -3.3602   -0.4886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4829   -1.0936   -1.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066   -1.3561   -1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4855   -0.2009   -0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6011    0.4230    0.3461 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0695    1.8989    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679   -0.0501    1.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9914   -0.8087    1.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3080    0.2491    2.8423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1944    0.3763   -0.0590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1509    0.8196    0.8903 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0021    2.2948    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4089    2.9591   -0.1185 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6120    2.9538    1.9335 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1390    0.2359    0.3041 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9566   -0.4815    1.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0983    1.2981   -0.1804 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1508    1.2966   -1.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4968    1.1295    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5483    2.5988    0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0935   -0.9544    1.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7121   -2.3177   -0.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4573   -0.8073   -1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6320   -2.2358   -1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -2.5676   -0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.0671   -1.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3700   -3.4560   -1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -1.9318   -2.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392   -0.1241   -2.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9364   -2.2430   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -1.5221   -2.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641    0.5362   -1.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4033   -0.5612   -0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6883    2.4228    1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875    2.3672   -0.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1928    1.7826    0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8906   -0.4851    3.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066    1.0880   -0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2030    0.4178    1.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4751    3.9329    2.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718   -1.4898    1.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543    0.1995    2.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8870    2.3095    0.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9377    1.8726   -1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  1
 16 17  2  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  0
 26  2  1  0
 25  3  1  0
 24  6  1  0
 19  7  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  1
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  6
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 18 46  1  0
 19 47  1  6
 20 48  1  1
 23 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  1
 27 53  1  0
M  END

HEADER    PROTEIN                                 23-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUL-20         0                                  
HETATM    1  C   UNK     0      -2.536   1.971   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.262  -0.815   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.027   1.978   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.703   3.161   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.128   3.745   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.271   1.683   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.473   2.995   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.695   0.332   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.725   1.476   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.158   0.424   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.204   1.044   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0      -0.214   0.222   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0      -1.199   2.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.202   1.201   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.739  -2.279   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.246  -2.598   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.290  -3.424   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.531   3.520   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.136   3.514   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -3.870   1.201   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.536  -1.108   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.554  -2.292   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -3.500  -2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.203  -0.339   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.868  -0.339   0.000  0.00  0.00           C+0
HETATM   26  H   UNK     0      -1.205  -1.669   0.000  0.00  0.00           H+0
HETATM   27  O   UNK     0      -5.022  -2.076   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -2.941  -3.745   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       3.279  -1.093   0.000  0.00  0.00           O+0
CONECT    1   14   20                                                       
CONECT    2   10   15   24                                                  
CONECT    3   10    7                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   10   12   14                                             
CONECT    7    5    9    3                                                  
CONECT    8    9   10   29                                                  
CONECT    9    7    8   11                                                  
CONECT   10    6    8    3    2                                             
CONECT   11    9                                                            
CONECT   12    6                                                            
CONECT   13   14   19   18                                                  
CONECT   14   13    1    6   24                                             
CONECT   15    2   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   13                                                            
CONECT   19   13                                                            
CONECT   20    1   25                                                       
CONECT   21   24   25   22   23                                             
CONECT   22   21                                                            
CONECT   23   21   27   28                                                  
CONECT   24   21   26   14    2                                             
CONECT   25   21   20                                                       
CONECT   26   24                                                            
CONECT   27   23                                                            
CONECT   28   23                                                            
CONECT   29    8                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0036900
HETATM    1  C1  UNL     1       4.561   1.555   0.324  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.452   0.861   0.250  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.307  -0.577   0.597  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.100  -1.394  -0.658  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.659  -1.812  -0.868  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.741  -0.634  -0.858  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.701  -0.933  -0.596  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.955  -2.133   0.160  1.00  0.00           C  
HETATM    9  O1  UNL     1      -1.377  -2.281   1.317  1.00  0.00           O  
HETATM   10  O2  UNL     1      -0.691  -3.360  -0.489  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.483  -1.094  -1.918  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.907  -1.356  -1.438  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.485  -0.201  -0.710  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.601   0.423   0.346  1.00  0.00           C  
HETATM   15  C13 UNL     1      -3.069   1.899   0.347  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.968  -0.050   1.681  1.00  0.00           C  
HETATM   17  O3  UNL     1      -3.991  -0.809   1.795  1.00  0.00           O  
HETATM   18  O4  UNL     1      -2.308   0.249   2.842  1.00  0.00           O  
HETATM   19  C15 UNL     1      -1.194   0.376  -0.059  1.00  0.00           C  
HETATM   20  C16 UNL     1      -0.151   0.820   0.890  1.00  0.00           C  
HETATM   21  C17 UNL     1       0.002   2.295   0.862  1.00  0.00           C  
HETATM   22  O5  UNL     1      -0.409   2.959  -0.118  1.00  0.00           O  
HETATM   23  O6  UNL     1       0.612   2.954   1.934  1.00  0.00           O  
HETATM   24  C18 UNL     1       1.139   0.236   0.304  1.00  0.00           C  
HETATM   25  C19 UNL     1       1.957  -0.481   1.329  1.00  0.00           C  
HETATM   26  C20 UNL     1       2.098   1.298  -0.180  1.00  0.00           C  
HETATM   27  O7  UNL     1       2.151   1.297  -1.597  1.00  0.00           O  
HETATM   28  H1  UNL     1       5.497   1.130   0.655  1.00  0.00           H  
HETATM   29  H2  UNL     1       4.548   2.599   0.045  1.00  0.00           H  
HETATM   30  H3  UNL     1       4.094  -0.954   1.249  1.00  0.00           H  
HETATM   31  H4  UNL     1       3.712  -2.318  -0.577  1.00  0.00           H  
HETATM   32  H5  UNL     1       3.457  -0.807  -1.510  1.00  0.00           H  
HETATM   33  H6  UNL     1       1.632  -2.236  -1.913  1.00  0.00           H  
HETATM   34  H7  UNL     1       1.438  -2.568  -0.117  1.00  0.00           H  
HETATM   35  H8  UNL     1       0.839  -0.067  -1.808  1.00  0.00           H  
HETATM   36  H9  UNL     1      -0.370  -3.456  -1.418  1.00  0.00           H  
HETATM   37  H10 UNL     1      -1.142  -1.932  -2.515  1.00  0.00           H  
HETATM   38  H11 UNL     1      -1.439  -0.124  -2.423  1.00  0.00           H  
HETATM   39  H12 UNL     1      -2.936  -2.243  -0.802  1.00  0.00           H  
HETATM   40  H13 UNL     1      -3.506  -1.522  -2.353  1.00  0.00           H  
HETATM   41  H14 UNL     1      -3.864   0.536  -1.456  1.00  0.00           H  
HETATM   42  H15 UNL     1      -4.403  -0.561  -0.177  1.00  0.00           H  
HETATM   43  H16 UNL     1      -2.688   2.423   1.216  1.00  0.00           H  
HETATM   44  H17 UNL     1      -2.988   2.367  -0.627  1.00  0.00           H  
HETATM   45  H18 UNL     1      -4.193   1.783   0.505  1.00  0.00           H  
HETATM   46  H19 UNL     1      -1.891  -0.485   3.407  1.00  0.00           H  
HETATM   47  H20 UNL     1      -1.107   1.088  -0.945  1.00  0.00           H  
HETATM   48  H21 UNL     1      -0.203   0.418   1.911  1.00  0.00           H  
HETATM   49  H22 UNL     1       0.475   3.933   2.045  1.00  0.00           H  
HETATM   50  H23 UNL     1       1.672  -1.490   1.583  1.00  0.00           H  
HETATM   51  H24 UNL     1       2.054   0.199   2.209  1.00  0.00           H  
HETATM   52  H25 UNL     1       1.887   2.310   0.146  1.00  0.00           H  
HETATM   53  H26 UNL     1       2.938   1.873  -1.822  1.00  0.00           H  
CONECT    1    2    2   28   29
CONECT    2    3   26
CONECT    3    4   25   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7   24   35
CONECT    7    8   11   19
CONECT    8    9    9   10
CONECT   10   36
CONECT   11   12   37   38
CONECT   12   13   39   40
CONECT   13   14   41   42
CONECT   14   15   16   19
CONECT   15   43   44   45
CONECT   16   17   17   18
CONECT   18   46
CONECT   19   20   47
CONECT   20   21   24   48
CONECT   21   22   22   23
CONECT   23   49
CONECT   24   25   26
CONECT   25   50   51
CONECT   26   27   52
CONECT   27   53
END

HMDB0036900
     RDKit          3D
Gibberellin A66
 53 56  0  0  0  0  0  0  0  0999 V2000
    4.5608    1.5547    0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4522    0.8609    0.2501 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3074   -0.5770    0.5967 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1002   -1.3937   -0.6579 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6586   -1.8123   -0.8685 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7410   -0.6345   -0.8583 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7011   -0.9331   -0.5956 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9549   -2.1328    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -2.2808    1.3172 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6914   -3.3602   -0.4886 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4829   -1.0936   -1.9177 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9066   -1.3561   -1.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4855   -0.2009   -0.7102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6011    0.4230    0.3461 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0695    1.8989    0.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9679   -0.0501    1.6807 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9914   -0.8087    1.7954 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3080    0.2491    2.8423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1944    0.3763   -0.0590 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1509    0.8196    0.8903 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0021    2.2948    0.8618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4089    2.9591   -0.1185 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6120    2.9538    1.9335 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1390    0.2359    0.3041 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9566   -0.4815    1.3293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0983    1.2981   -0.1804 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1508    1.2966   -1.5968 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4968    1.1295    0.6545 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5483    2.5988    0.0453 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0935   -0.9544    1.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7121   -2.3177   -0.5765 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4573   -0.8073   -1.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6320   -2.2358   -1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375   -2.5676   -0.1171 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8388   -0.0671   -1.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3700   -3.4560   -1.4177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1419   -1.9318   -2.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4392   -0.1241   -2.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9364   -2.2430   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5063   -1.5221   -2.3528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8641    0.5362   -1.4559 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4033   -0.5612   -0.1768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6883    2.4228    1.2158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9875    2.3672   -0.6274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1928    1.7826    0.5054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8906   -0.4851    3.4069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1066    1.0880   -0.9445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2030    0.4178    1.9112 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4751    3.9329    2.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6718   -1.4898    1.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0543    0.1995    2.2091 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8870    2.3095    0.1462 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9377    1.8726   -1.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  8  9  2  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  1
 16 17  2  0
 16 18  1  0
 14 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 20 24  1  0
 24 25  1  1
 24 26  1  0
 26 27  1  0
 26  2  1  0
 25  3  1  0
 24  6  1  0
 19  7  1  0
  1 28  1  0
  1 29  1  0
  3 30  1  1
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  6
 10 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 15 43  1  0
 15 44  1  0
 15 45  1  0
 18 46  1  0
 19 47  1  6
 20 48  1  1
 23 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  1
 27 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1R,2S,3R,4R,8R,9R,12R,14R)-14-Hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0,.0,]pentadecane-2,4,8-tricarboxylate	HMDB
GA66	HMDB
Gibberellin A66	HMDB

Chemical Formula

C₂₀H₂₆O₇

Average Molecular Weight

378.421

Monoisotopic Molecular Weight

378.167853177

IUPAC Name

(1R,2S,3R,4R,8R,9R,12R,14R)-14-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylic acid

Traditional Name

(1R,2S,3R,4R,8R,9R,12R,14R)-14-hydroxy-4-methyl-13-methylidenetetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylic acid

CAS Registry Number

70980-48-2

SMILES

[H][C@@]12CC[C@@H]3C[C@]1([C@H](O)C3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C(O)=O

InChI Identifier

InChI=1S/C20H26O7/c1-9-10-4-5-11-19(17(26)27)7-3-6-18(2,16(24)25)13(19)12(15(22)23)20(11,8-10)14(9)21/h10-14,21H,1,3-8H2,2H3,(H,22,23)(H,24,25)(H,26,27)/t10-,11+,12-,13-,14-,18-,19-,20-/m1/s1

InChI Key

GYALTOSSVLCVLA-BPKUSKMISA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as c20-gibberellin 20-carboxylic acids. These are c20-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

C20-gibberellin 20-carboxylic acids

Alternative Parents

Substituents

Gibberellane-20-carboxylic acid
Gibberellane-6-carboxylic acid
Tricarboxylic acid or derivatives
Cyclic alcohol
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036900)

Source

Endogenous

Endogenous (HMDB: HMDB0036900)

Plant

Plant (HMDB: HMDB0036900)

Animal

Animal (HMDB: HMDB0036900)

Exogenous

Food

Food (HMDB: HMDB0036900)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0036900)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036900)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036900)

Lipid metabolism pathway (HMDB: HMDB0036900)

Cellular process

Cell signaling (HMDB: HMDB0036900)

Biochemical process

Lipid transport (HMDB: HMDB0036900)

Role

Biological role

Energy source (HMDB: HMDB0036900)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036900)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	2.23 g/L	ALOGPS
logP	0.55	ALOGPS
logP	1.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	3.67	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	92.08 m³·mol⁻¹	ChemAxon
Polarizability	37.75 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M-2H]-	215.821	30932474
DeepCCS	[M+Na]+	190.273	30932474
AllCCS	[M+H]+	185.8	32859911
AllCCS	[M+H-H2O]+	183.4	32859911
AllCCS	[M+NH4]+	188.1	32859911
AllCCS	[M+Na]+	188.8	32859911
AllCCS	[M-H]-	189.2	32859911
AllCCS	[M+Na-2H]-	189.2	32859911
AllCCS	[M+HCOO]-	189.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.42 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9991 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.67 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2034.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	195.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	149.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	166.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	212.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	404.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	521.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	134.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	900.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	436.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1376.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	282.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	382.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	331.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	181.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	191.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gibberellin A66	[H][C@@]12CC[C@@H]3C[C@]1([C@H](O)C3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C(O)=O	4302.3	Standard polar	33892256
Gibberellin A66	[H][C@@]12CC[C@@H]3C[C@]1([C@H](O)C3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C(O)=O	2622.8	Standard non polar	33892256
Gibberellin A66	[H][C@@]12CC[C@@H]3C[C@]1([C@H](O)C3=C)[C@@H](C(O)=O)[C@@]1([H])[C@]2(CCC[C@@]1(C)C(O)=O)C(O)=O	3070.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gibberellin A66,1TMS,isomer #1	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O[Si](C)(C)C	2900.0	Semi standard non polar	33892256
Gibberellin A66,1TMS,isomer #2	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O[Si](C)(C)C)[C@]3(C2)[C@@H]1O	2850.7	Semi standard non polar	33892256
Gibberellin A66,1TMS,isomer #3	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O	2867.6	Semi standard non polar	33892256
Gibberellin A66,1TMS,isomer #4	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O	2856.1	Semi standard non polar	33892256
Gibberellin A66,2TMS,isomer #1	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O[Si](C)(C)C	2855.5	Semi standard non polar	33892256
Gibberellin A66,2TMS,isomer #2	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O[Si](C)(C)C	2850.6	Semi standard non polar	33892256
Gibberellin A66,2TMS,isomer #3	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O[Si](C)(C)C)[C@]3(C2)[C@@H]1O[Si](C)(C)C	2844.7	Semi standard non polar	33892256
Gibberellin A66,2TMS,isomer #4	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O[Si](C)(C)C)[C@]3(C2)[C@@H]1O	2857.8	Semi standard non polar	33892256
Gibberellin A66,2TMS,isomer #5	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]4[C@H](C(=O)O[Si](C)(C)C)[C@]3(C2)[C@@H]1O	2866.6	Semi standard non polar	33892256
Gibberellin A66,2TMS,isomer #6	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O	2858.8	Semi standard non polar	33892256
Gibberellin A66,3TMS,isomer #1	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O[Si](C)(C)C	2865.6	Semi standard non polar	33892256
Gibberellin A66,3TMS,isomer #2	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O[Si](C)(C)C)[C@]3(C2)[C@@H]1O[Si](C)(C)C	2864.0	Semi standard non polar	33892256
Gibberellin A66,3TMS,isomer #3	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]4[C@H](C(=O)O[Si](C)(C)C)[C@]3(C2)[C@@H]1O[Si](C)(C)C	2858.1	Semi standard non polar	33892256
Gibberellin A66,3TMS,isomer #4	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]4[C@H](C(=O)O[Si](C)(C)C)[C@]3(C2)[C@@H]1O	2893.7	Semi standard non polar	33892256
Gibberellin A66,4TMS,isomer #1	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C)[C@H]4[C@H](C(=O)O[Si](C)(C)C)[C@]3(C2)[C@@H]1O[Si](C)(C)C	2907.1	Semi standard non polar	33892256
Gibberellin A66,1TBDMS,isomer #1	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3100.9	Semi standard non polar	33892256
Gibberellin A66,1TBDMS,isomer #2	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@]3(C2)[C@@H]1O	3087.3	Semi standard non polar	33892256
Gibberellin A66,1TBDMS,isomer #3	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O	3108.0	Semi standard non polar	33892256
Gibberellin A66,1TBDMS,isomer #4	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O	3100.6	Semi standard non polar	33892256
Gibberellin A66,2TBDMS,isomer #1	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3300.2	Semi standard non polar	33892256
Gibberellin A66,2TBDMS,isomer #2	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3294.9	Semi standard non polar	33892256
Gibberellin A66,2TBDMS,isomer #3	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@]3(C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3278.2	Semi standard non polar	33892256
Gibberellin A66,2TBDMS,isomer #4	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@]3(C2)[C@@H]1O	3306.2	Semi standard non polar	33892256
Gibberellin A66,2TBDMS,isomer #5	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]4[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@]3(C2)[C@@H]1O	3316.7	Semi standard non polar	33892256
Gibberellin A66,2TBDMS,isomer #6	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O	3320.7	Semi standard non polar	33892256
Gibberellin A66,3TBDMS,isomer #1	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]4[C@H](C(=O)O)[C@]3(C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3495.4	Semi standard non polar	33892256
Gibberellin A66,3TBDMS,isomer #2	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O)[C@H]4[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@]3(C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3495.6	Semi standard non polar	33892256
Gibberellin A66,3TBDMS,isomer #3	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]4[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@]3(C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3478.6	Semi standard non polar	33892256
Gibberellin A66,3TBDMS,isomer #4	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]4[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@]3(C2)[C@@H]1O	3516.6	Semi standard non polar	33892256
Gibberellin A66,4TBDMS,isomer #1	C=C1[C@@H]2CC[C@H]3[C@]4(C(=O)O[Si](C)(C)C(C)(C)C)CCC[C@@](C)(C(=O)O[Si](C)(C)C(C)(C)C)[C@H]4[C@H](C(=O)O[Si](C)(C)C(C)(C)C)[C@]3(C2)[C@@H]1O[Si](C)(C)C(C)(C)C	3696.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Gibberellin A66 GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gibberellin A66 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 - Gibberellin A66 10V, Positive-QTOF	splash10-004i-0009000000-dc3a9890d8177e3fc4fe	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gibberellin A66 20V, Positive-QTOF	splash10-004r-0029000000-39baf37771227fe0abf3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gibberellin A66 40V, Positive-QTOF	splash10-004j-0019000000-cf1d482c4adad51dd4e5	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gibberellin A66 10V, Negative-QTOF	splash10-003i-0079000000-247477f7e87703c0b0cd	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gibberellin A66 20V, Negative-QTOF	splash10-000i-0092000000-2ab39bcc62f5aafefc9c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gibberellin A66 40V, Negative-QTOF	splash10-00my-2329000000-cc91e1bdfb4e450892be	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB015862

KNApSAcK ID

C00000066

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

156908042

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 Gibberellin A66 (HMDB0036900)

MOL for HMDB0036900 (Gibberellin A66)

3D MOL for HMDB0036900 (Gibberellin A66)

3D SDF for HMDB0036900 (Gibberellin A66)

3D-SDF for HMDB0036900 (Gibberellin A66)

PDB for HMDB0036900 (Gibberellin A66)

3D PDB for HMDB0036900 (Gibberellin A66)

SMILES for HMDB0036900 (Gibberellin A66)

INCHI for HMDB0036900 (Gibberellin A66)

Structure for HMDB0036900 (Gibberellin A66)

3D Structure for HMDB0036900 (Gibberellin A66)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra