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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:51:39 UTC

Update Date

2022-03-07 02:55:01 UTC

HMDB ID

HMDB0036694

Secondary Accession Numbers

HMDB36694

Metabolite Identification

Common Name

15-Hydroxyleptocarpin

Description

15-Hydroxyleptocarpin, also known as ac-asp-ile-val-pro-cys-OH, belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. 15-Hydroxyleptocarpin is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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


  Mrv0541 05061309172D          

 27 29  0  0  0  0            999 V2000
    3.5024   -2.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6566   -1.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7485   -1.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3210   -0.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3153   -2.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599    1.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7057    1.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2747   -0.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7626    2.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8437   -1.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0553   -0.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0470    2.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5186    1.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1444    1.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8031    0.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1773    0.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6160    0.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5592   -0.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8552   -0.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618    0.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2910    3.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936    0.5809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7463   -0.6670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4888   -0.5654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9103    0.7862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0876   -0.1742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6489    0.2482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  5  2  0  0  0  0
 11  3  2  0  0  0  0
 12  6  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 16  7  1  0  0  0  0
 17 11  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20  4  1  0  0  0  0
 20  8  1  0  0  0  0
 20 16  1  0  0  0  0
 21  9  1  0  0  0  0
 22 13  1  0  0  0  0
 23 18  2  0  0  0  0
 24 19  2  0  0  0  0
 25 14  1  0  0  0  0
 25 19  1  0  0  0  0
 26 15  1  0  0  0  0
 26 18  1  0  0  0  0
 27 16  1  0  0  0  0
 27 20  1  0  0  0  0
M  END

HMDB0036694
     RDKit          3D
15-Hydroxyleptocarpin
 53 55  0  0  0  0  0  0  0  0999 V2000
    0.8173   -0.9614   -3.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4095    0.0377   -2.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6425    1.4527   -2.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107    1.9617   -3.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4229    2.1452   -2.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9947    1.3612   -1.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4219    1.2237   -1.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884    0.9307   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7215    0.8214   -0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4164    1.7899   -0.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8601    0.7174    0.9524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202    1.2460    1.7384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -0.7702    1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7439   -1.0494    2.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6572   -0.1331    2.4567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -1.4531    2.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3617   -2.2558    3.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0219   -1.6296    0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4322   -0.3189   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371   -0.2872   -0.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6588    0.5827    0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0821    1.3702    1.2620 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932    0.6658    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8953    1.6481    1.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7443   -0.1285   -0.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0381   -1.1497   -1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3661   -0.0260   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -1.9885   -3.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3729   -0.7592   -4.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6931    1.8138   -0.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7899    1.3687   -2.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1024   -0.1895   -0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8854    1.1033   -1.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3390    1.8673   -0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891    1.2720    1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342    2.2257    1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7834   -1.1118    1.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6581   -1.3796    0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238   -1.2902    3.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2783   -2.5546    3.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237   -1.6790    3.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260   -3.1948    2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7909   -2.0726   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8586   -2.3084    0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009    0.4728    0.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1958    2.4037    1.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881    1.1394    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5830    2.1731    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8367   -0.0182   -0.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4879   -1.8560   -0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8324   -1.7399   -1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -0.6694   -2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1542   -0.8196   -1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 19 27  1  0
 27  2  1  0
 27  6  1  0
 16 14  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
M  END


  Mrv0541 05061309172D          

 27 29  0  0  0  0            999 V2000
    3.5024   -2.0749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6566   -1.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7485   -1.0048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3210   -0.7055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3153   -2.2158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8599    1.8673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7057    1.5154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2747   -0.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7626    2.7825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8437   -1.5822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0553   -0.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0470    2.0081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5186    1.3746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1444    1.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8031    0.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1773    0.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6160    0.4594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5592   -0.8078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8552   -0.0370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4618    0.1074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2910    3.4161    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2936    0.5809    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7463   -0.6670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4888   -0.5654    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9103    0.7862    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0876   -0.1742    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6489    0.2482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  5  2  0  0  0  0
 11  3  2  0  0  0  0
 12  6  2  0  0  0  0
 12  9  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 16  7  1  0  0  0  0
 17 11  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20  4  1  0  0  0  0
 20  8  1  0  0  0  0
 20 16  1  0  0  0  0
 21  9  1  0  0  0  0
 22 13  1  0  0  0  0
 23 18  2  0  0  0  0
 24 19  2  0  0  0  0
 25 14  1  0  0  0  0
 25 19  1  0  0  0  0
 26 15  1  0  0  0  0
 26 18  1  0  0  0  0
 27 16  1  0  0  0  0
 27 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036694

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C(\C)C(=O)OC1CC2(C)OC2CC(O)\C(CO)=C/C2OC(=O)C(=C)C12

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O7/c1-5-10(2)18(23)26-15-8-20(4)16(27-20)7-13(22)12(9-21)6-14-17(15)11(3)19(24)25-14/h5-6,13-17,21-22H,3,7-9H2,1-2,4H3/b10-5-,12-6-

> <INCHI_KEY>
WRYLLOROOPMFIC-ZIIBAIFASA-N

> <FORMULA>
C20H26O7

> <MOLECULAR_WEIGHT>
378.4162

> <EXACT_MASS>
378.167853186

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
39.186172380504686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z)-8-hydroxy-9-(hydroxymethyl)-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2Z)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
0.56

> <JCHEM_LOGP>
1.125990337333334

> <ALOGPS_LOGS>
-2.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.36361935863475

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.213378118693682

> <JCHEM_PKA_STRONGEST_BASIC>
-2.766061259279562

> <JCHEM_POLAR_SURFACE_AREA>
105.59

> <JCHEM_REFRACTIVITY>
97.31039999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9Z)-8-hydroxy-9-(hydroxymethyl)-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2Z)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036694
     RDKit          3D
15-Hydroxyleptocarpin
 53 55  0  0  0  0  0  0  0  0999 V2000
    0.8173   -0.9614   -3.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4095    0.0377   -2.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6425    1.4527   -2.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107    1.9617   -3.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4229    2.1452   -2.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9947    1.3612   -1.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4219    1.2237   -1.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884    0.9307   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7215    0.8214   -0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4164    1.7899   -0.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8601    0.7174    0.9524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202    1.2460    1.7384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -0.7702    1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7439   -1.0494    2.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6572   -0.1331    2.4567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -1.4531    2.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3617   -2.2558    3.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0219   -1.6296    0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4322   -0.3189   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371   -0.2872   -0.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6588    0.5827    0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0821    1.3702    1.2620 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932    0.6658    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8953    1.6481    1.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7443   -0.1285   -0.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0381   -1.1497   -1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3661   -0.0260   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -1.9885   -3.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3729   -0.7592   -4.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6931    1.8138   -0.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7899    1.3687   -2.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1024   -0.1895   -0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8854    1.1033   -1.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3390    1.8673   -0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891    1.2720    1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342    2.2257    1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7834   -1.1118    1.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6581   -1.3796    0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238   -1.2902    3.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2783   -2.5546    3.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237   -1.6790    3.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260   -3.1948    2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7909   -2.0726   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8586   -2.3084    0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009    0.4728    0.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1958    2.4037    1.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881    1.1394    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5830    2.1731    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8367   -0.0182   -0.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4879   -1.8560   -0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8324   -1.7399   -1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -0.6694   -2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1542   -0.8196   -1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 19 27  1  0
 27  2  1  0
 27  6  1  0
 16 14  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.538  -3.873   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.559  -3.216   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.731  -1.876   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.199  -1.317   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.055  -4.136   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.938   3.486   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.917   2.829   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.979  -0.062   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.890   5.194   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.042  -2.953   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.303  -0.446   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.421   3.748   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.435   2.566   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      11.470   2.040   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.966   1.120   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.931   1.646   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.483   0.858   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.511  -1.508   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      12.796  -0.069   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.462   0.200   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.877   6.377   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       8.015   1.084   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.993  -1.245   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      13.979  -1.055   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      12.899   1.468   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       9.497  -0.325   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.945   0.463   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   20                                                            
CONECT    5    1   10                                                       
CONECT    6   12   14                                                       
CONECT    7   13   16                                                       
CONECT    8   15   20                                                       
CONECT    9   12   21                                                       
CONECT   10    2    5   18                                                  
CONECT   11    3   17   19                                                  
CONECT   12    6    9   13                                                  
CONECT   13    7   12   22                                                  
CONECT   14    6   17   25                                                  
CONECT   15    8   17   26                                                  
CONECT   16    7   20   27                                                  
CONECT   17   11   14   15                                                  
CONECT   18   10   23   26                                                  
CONECT   19   11   24   25                                                  
CONECT   20    4    8   16   27                                             
CONECT   21    9                                                            
CONECT   22   13                                                            
CONECT   23   18                                                            
CONECT   24   19                                                            
CONECT   25   14   19                                                       
CONECT   26   15   18                                                       
CONECT   27   16   20                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

COMPND    HMDB0036694
HETATM    1  C1  UNL     1       0.817  -0.961  -3.278  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.409   0.038  -2.522  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.643   1.453  -2.780  1.00  0.00           C  
HETATM    4  O1  UNL     1       1.611   1.962  -3.419  1.00  0.00           O  
HETATM    5  O2  UNL     1      -0.423   2.145  -2.178  1.00  0.00           O  
HETATM    6  C4  UNL     1      -0.995   1.361  -1.147  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.422   1.224  -1.388  1.00  0.00           C  
HETATM    8  C6  UNL     1      -3.288   0.931  -0.443  1.00  0.00           C  
HETATM    9  C7  UNL     1      -4.722   0.821  -0.835  1.00  0.00           C  
HETATM   10  O3  UNL     1      -5.416   1.790  -0.080  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.860   0.717   0.952  1.00  0.00           C  
HETATM   12  O4  UNL     1      -3.920   1.246   1.738  1.00  0.00           O  
HETATM   13  C9  UNL     1      -2.779  -0.770   1.315  1.00  0.00           C  
HETATM   14  C10 UNL     1      -1.744  -1.049   2.351  1.00  0.00           C  
HETATM   15  O5  UNL     1      -0.657  -0.133   2.457  1.00  0.00           O  
HETATM   16  C11 UNL     1      -0.451  -1.453   2.016  1.00  0.00           C  
HETATM   17  C12 UNL     1       0.362  -2.256   3.031  1.00  0.00           C  
HETATM   18  C13 UNL     1      -0.022  -1.630   0.611  1.00  0.00           C  
HETATM   19  C14 UNL     1       0.432  -0.319  -0.046  1.00  0.00           C  
HETATM   20  O6  UNL     1       1.837  -0.287  -0.234  1.00  0.00           O  
HETATM   21  C15 UNL     1       2.659   0.583   0.445  1.00  0.00           C  
HETATM   22  O7  UNL     1       2.082   1.370   1.262  1.00  0.00           O  
HETATM   23  C16 UNL     1       4.093   0.666   0.303  1.00  0.00           C  
HETATM   24  C17 UNL     1       4.895   1.648   1.087  1.00  0.00           C  
HETATM   25  C18 UNL     1       4.744  -0.128  -0.528  1.00  0.00           C  
HETATM   26  C19 UNL     1       4.038  -1.150  -1.361  1.00  0.00           C  
HETATM   27  C20 UNL     1      -0.366  -0.026  -1.264  1.00  0.00           C  
HETATM   28  H1  UNL     1       0.604  -1.988  -3.019  1.00  0.00           H  
HETATM   29  H2  UNL     1       1.373  -0.759  -4.170  1.00  0.00           H  
HETATM   30  H3  UNL     1      -0.693   1.814  -0.202  1.00  0.00           H  
HETATM   31  H4  UNL     1      -2.790   1.369  -2.398  1.00  0.00           H  
HETATM   32  H5  UNL     1      -5.102  -0.189  -0.585  1.00  0.00           H  
HETATM   33  H6  UNL     1      -4.885   1.103  -1.893  1.00  0.00           H  
HETATM   34  H7  UNL     1      -6.339   1.867  -0.441  1.00  0.00           H  
HETATM   35  H8  UNL     1      -1.989   1.272   1.272  1.00  0.00           H  
HETATM   36  H9  UNL     1      -3.834   2.226   1.826  1.00  0.00           H  
HETATM   37  H10 UNL     1      -3.783  -1.112   1.713  1.00  0.00           H  
HETATM   38  H11 UNL     1      -2.658  -1.380   0.385  1.00  0.00           H  
HETATM   39  H12 UNL     1      -2.124  -1.290   3.389  1.00  0.00           H  
HETATM   40  H13 UNL     1      -0.278  -2.555   3.881  1.00  0.00           H  
HETATM   41  H14 UNL     1       1.224  -1.679   3.407  1.00  0.00           H  
HETATM   42  H15 UNL     1       0.726  -3.195   2.549  1.00  0.00           H  
HETATM   43  H16 UNL     1      -0.791  -2.073  -0.054  1.00  0.00           H  
HETATM   44  H17 UNL     1       0.859  -2.308   0.526  1.00  0.00           H  
HETATM   45  H18 UNL     1       0.201   0.473   0.726  1.00  0.00           H  
HETATM   46  H19 UNL     1       4.196   2.404   1.495  1.00  0.00           H  
HETATM   47  H20 UNL     1       5.488   1.139   1.878  1.00  0.00           H  
HETATM   48  H21 UNL     1       5.583   2.173   0.392  1.00  0.00           H  
HETATM   49  H22 UNL     1       5.837  -0.018  -0.593  1.00  0.00           H  
HETATM   50  H23 UNL     1       3.488  -1.856  -0.718  1.00  0.00           H  
HETATM   51  H24 UNL     1       4.832  -1.740  -1.898  1.00  0.00           H  
HETATM   52  H25 UNL     1       3.454  -0.669  -2.149  1.00  0.00           H  
HETATM   53  H26 UNL     1      -1.154  -0.820  -1.389  1.00  0.00           H  
CONECT    1    2    2   28   29
CONECT    2    3   27
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   27   30
CONECT    7    8    8   31
CONECT    8    9   11
CONECT    9   10   32   33
CONECT   10   34
CONECT   11   12   13   35
CONECT   12   36
CONECT   13   14   37   38
CONECT   14   15   16   39
CONECT   15   16
CONECT   16   17   18
CONECT   17   40   41   42
CONECT   18   19   43   44
CONECT   19   20   27   45
CONECT   20   21
CONECT   21   22   22   23
CONECT   23   24   25   25
CONECT   24   46   47   48
CONECT   25   26   49
CONECT   26   50   51   52
CONECT   27   53
END

HMDB0036694
     RDKit          3D
15-Hydroxyleptocarpin
 53 55  0  0  0  0  0  0  0  0999 V2000
    0.8173   -0.9614   -3.2782 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4095    0.0377   -2.5220 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6425    1.4527   -2.7799 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6107    1.9617   -3.4188 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4229    2.1452   -2.1779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9947    1.3612   -1.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4219    1.2237   -1.3879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2884    0.9307   -0.4435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7215    0.8214   -0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4164    1.7899   -0.0798 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8601    0.7174    0.9524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9202    1.2460    1.7384 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7789   -0.7702    1.3153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7439   -1.0494    2.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6572   -0.1331    2.4567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4511   -1.4531    2.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3617   -2.2558    3.0309 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0219   -1.6296    0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4322   -0.3189   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8371   -0.2872   -0.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6588    0.5827    0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0821    1.3702    1.2620 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0932    0.6658    0.3035 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8953    1.6481    1.0867 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7443   -0.1285   -0.5277 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0381   -1.1497   -1.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3661   -0.0260   -1.2639 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -1.9885   -3.0190 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3729   -0.7592   -4.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6931    1.8138   -0.2020 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7899    1.3687   -2.3976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1024   -0.1895   -0.5846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8854    1.1033   -1.8928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3390    1.8673   -0.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9891    1.2720    1.2724 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8342    2.2257    1.8260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7834   -1.1118    1.7128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6581   -1.3796    0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1238   -1.2902    3.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2783   -2.5546    3.8806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237   -1.6790    3.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7260   -3.1948    2.5494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7909   -2.0726   -0.0538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8586   -2.3084    0.5265 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2009    0.4728    0.7264 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1958    2.4037    1.4952 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881    1.1394    1.8776 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5830    2.1731    0.3920 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8367   -0.0182   -0.5926 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4879   -1.8560   -0.7179 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8324   -1.7399   -1.8980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539   -0.6694   -2.1485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1542   -0.8196   -1.3888 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 19 27  1  0
 27  2  1  0
 27  6  1  0
 16 14  1  0
  1 28  1  0
  1 29  1  0
  6 30  1  0
  7 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
 24 46  1  0
 24 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ac-asp-ile-val-pro-cys-OH	HMDB
(9Z)-8-Hydroxy-9-(hydroxymethyl)-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2Z)-2-methylbut-2-enoic acid	Generator

Chemical Formula

C₂₀H₂₆O₇

Average Molecular Weight

378.4162

Monoisotopic Molecular Weight

378.167853186

IUPAC Name

(9Z)-8-hydroxy-9-(hydroxymethyl)-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2Z)-2-methylbut-2-enoate

Traditional Name

(9Z)-8-hydroxy-9-(hydroxymethyl)-4-methyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2Z)-2-methylbut-2-enoate

CAS Registry Number

121541-07-9

SMILES

C\C=C(\C)C(=O)OC1CC2(C)OC2CC(O)\C(CO)=C/C2OC(=O)C(=C)C12

InChI Identifier

InChI=1S/C20H26O7/c1-5-10(2)18(23)26-15-8-20(4)16(27-20)7-13(22)12(9-21)6-14-17(15)11(3)19(24)25-14/h5-6,13-17,21-22H,3,7-9H2,1-2,4H3/b10-5-,12-6-

InChI Key

WRYLLOROOPMFIC-ZIIBAIFASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Germacranolides and derivatives

Alternative Parents

Substituents

Germacranolide
Sesquiterpenoid
Fatty acid ester
Dicarboxylic acid or derivatives
Gamma butyrolactone
Fatty acyl
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Lactone
Secondary alcohol
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Primary alcohol
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036694)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036694)

Source

Endogenous

Endogenous (HMDB: HMDB0036694)

Animal

Animal (HMDB: HMDB0036694)

Exogenous

Food

Food (HMDB: HMDB0036694)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036694)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036694)

Cellular process

Cell signaling (HMDB: HMDB0036694)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036694)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036694)

Nutrient

Nutrient (HMDB: HMDB0036694)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036694)

Emulsifier (HMDB: HMDB0036694)

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
Water Solubility	1.13 g/L	ALOGPS
logP	0.56	ALOGPS
logP	1.13	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	6.21	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	105.59 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.31 m³·mol⁻¹	ChemAxon
Polarizability	39.19 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	188.885	31661259
DarkChem	[M-H]-	183.822	31661259
DeepCCS	[M-2H]-	224.202	30932474
DeepCCS	[M+Na]+	199.43	30932474
AllCCS	[M+H]+	190.5	32859911
AllCCS	[M+H-H2O]+	187.9	32859911
AllCCS	[M+NH4]+	192.9	32859911
AllCCS	[M+Na]+	193.6	32859911
AllCCS	[M-H]-	190.5	32859911
AllCCS	[M+Na-2H]-	190.9	32859911
AllCCS	[M+HCOO]-	191.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
15-Hydroxyleptocarpin	C\C=C(\C)C(=O)OC1CC2(C)OC2CC(O)\C(CO)=C/C2OC(=O)C(=C)C12	3796.0	Standard polar	33892256
15-Hydroxyleptocarpin	C\C=C(\C)C(=O)OC1CC2(C)OC2CC(O)\C(CO)=C/C2OC(=O)C(=C)C12	2723.2	Standard non polar	33892256
15-Hydroxyleptocarpin	C\C=C(\C)C(=O)OC1CC2(C)OC2CC(O)\C(CO)=C/C2OC(=O)C(=C)C12	3013.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
15-Hydroxyleptocarpin,1TMS,isomer #1	C=C1C(=O)OC2/C=C(/CO)C(O[Si](C)(C)C)CC3OC3(C)CC(OC(=O)/C(C)=C\C)C12	2870.2	Semi standard non polar	33892256
15-Hydroxyleptocarpin,1TMS,isomer #2	C=C1C(=O)OC2/C=C(/CO[Si](C)(C)C)C(O)CC3OC3(C)CC(OC(=O)/C(C)=C\C)C12	2866.6	Semi standard non polar	33892256
15-Hydroxyleptocarpin,2TMS,isomer #1	C=C1C(=O)OC2/C=C(/CO[Si](C)(C)C)C(O[Si](C)(C)C)CC3OC3(C)CC(OC(=O)/C(C)=C\C)C12	2853.2	Semi standard non polar	33892256
15-Hydroxyleptocarpin,1TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/CO)C(O[Si](C)(C)C(C)(C)C)CC3OC3(C)CC(OC(=O)/C(C)=C\C)C12	3093.1	Semi standard non polar	33892256
15-Hydroxyleptocarpin,1TBDMS,isomer #2	C=C1C(=O)OC2/C=C(/CO[Si](C)(C)C(C)(C)C)C(O)CC3OC3(C)CC(OC(=O)/C(C)=C\C)C12	3087.2	Semi standard non polar	33892256
15-Hydroxyleptocarpin,2TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)CC3OC3(C)CC(OC(=O)/C(C)=C\C)C12	3292.8	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 - 15-Hydroxyleptocarpin GC-MS (Non-derivatized) - 70eV, Positive	splash10-08gi-9016000000-5752f1cf79eedb04063d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15-Hydroxyleptocarpin GC-MS (2 TMS) - 70eV, Positive	splash10-053r-9000200000-e0c138046840f2796903	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 15-Hydroxyleptocarpin 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 - 15-Hydroxyleptocarpin 10V, Positive-QTOF	splash10-03fr-1029000000-857ffdbdaa774edc7aed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Hydroxyleptocarpin 20V, Positive-QTOF	splash10-03gl-8098000000-6c08f6f01132f42c0b49	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Hydroxyleptocarpin 40V, Positive-QTOF	splash10-0f89-9030000000-15e616ecf947e3e91b12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Hydroxyleptocarpin 10V, Negative-QTOF	splash10-004i-0019000000-874c1c071f657adc28dc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Hydroxyleptocarpin 20V, Negative-QTOF	splash10-054k-3029000000-db8b5fb9159fe3e43bbb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Hydroxyleptocarpin 40V, Negative-QTOF	splash10-0kub-9451000000-68c25aa907ed9b916423	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Hydroxyleptocarpin 10V, Positive-QTOF	splash10-03fr-0090000000-228079ec4b617d63fc84	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Hydroxyleptocarpin 20V, Positive-QTOF	splash10-03fr-0095000000-d7c1706be51199e0f302	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Hydroxyleptocarpin 40V, Positive-QTOF	splash10-0cdi-7096000000-b7e5dcda965de797294c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Hydroxyleptocarpin 10V, Negative-QTOF	splash10-004j-3092000000-a5bc58ede1e71ba98565	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Hydroxyleptocarpin 20V, Negative-QTOF	splash10-002b-9080000000-7ba7d2890b883f9964c1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 15-Hydroxyleptocarpin 40V, Negative-QTOF	splash10-01t9-2090000000-f60675acb39357993c8f	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

FDB015627

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

131752040

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 15-Hydroxyleptocarpin (HMDB0036694)

MOL for HMDB0036694 (15-Hydroxyleptocarpin)

3D MOL for HMDB0036694 (15-Hydroxyleptocarpin)

3D SDF for HMDB0036694 (15-Hydroxyleptocarpin)

3D-SDF for HMDB0036694 (15-Hydroxyleptocarpin)

PDB for HMDB0036694 (15-Hydroxyleptocarpin)

3D PDB for HMDB0036694 (15-Hydroxyleptocarpin)

SMILES for HMDB0036694 (15-Hydroxyleptocarpin)

INCHI for HMDB0036694 (15-Hydroxyleptocarpin)

Structure for HMDB0036694 (15-Hydroxyleptocarpin)

3D Structure for HMDB0036694 (15-Hydroxyleptocarpin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra