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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:51:31 UTC

Update Date

2022-03-07 02:55:01 UTC

HMDB ID

HMDB0036692

Secondary Accession Numbers

HMDB36692

Metabolite Identification

Common Name

Heliangin

Description

Heliangin 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. Based on a literature review a significant number of articles have been published on Heliangin.

Structure

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


  Mrv0541 05061309172D          

 26 28  0  0  0  0            999 V2000
    4.5998   -2.9902    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
    4.7626    2.7825    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
    4.8437   -1.5822    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
    6.0553   -0.2390    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
    4.2341    2.1490    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
  6  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  6  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  4  2  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 16  8  1  0  0  0  0
 17 12  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 12  1  0  0  0  0
 20  5  1  0  0  0  0
 20  9  1  0  0  0  0
 20 16  1  0  0  0  0
 21 13  1  0  0  0  0
 22 18  2  0  0  0  0
 23 19  2  0  0  0  0
 24 14  1  0  0  0  0
 24 19  1  0  0  0  0
 25 15  1  0  0  0  0
 25 18  1  0  0  0  0
 26 16  1  0  0  0  0
 26 20  1  0  0  0  0
M  END

HMDB0036692
     RDKit          3D
Heliangin
 52 54  0  0  0  0  0  0  0  0999 V2000
   -0.1689    3.9051   -0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9771    2.8970   -0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971    2.8421   -1.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7155    3.8543   -2.2476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6368    1.5078   -1.7314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683    0.7621   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5834   -0.6544   -1.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586   -1.3255   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594   -2.8373   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4330   -0.6346    0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6270   -1.4113    0.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9941   -0.7248    1.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7141   -1.4597    1.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2570   -1.1749    3.2239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860   -0.8816    1.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7464   -1.7667    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    0.5632    1.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1414    1.1433    0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549    0.5878    0.0111 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    1.0200   -0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7599    2.1320    0.2772 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5123    0.2191   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1839   -1.1235   -1.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625    0.6538   -0.9648 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7694   -0.1907   -1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0066    1.5368   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    3.8935   -0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    4.8347   -1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897    1.0750   -2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730   -1.2572   -1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370   -3.2044   -0.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -3.1437   -1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2191   -3.2410   -0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7619    0.3522   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2968   -1.0209    0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7616   -1.2629    2.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9648    0.2986    2.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -2.5679    1.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -1.2158    2.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508   -2.0502    0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -2.6940    2.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0029    1.1825    2.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    0.7276    2.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545    2.1378    0.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7568   -1.8633   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072   -1.3123   -1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5065   -1.2551   -2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0032    1.6440   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7598    0.0457   -2.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5409   -1.2681   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7612    0.0675   -1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8790    1.6580    0.5011 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
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 18 26  1  0
 26  2  1  0
 26  6  1  0
 15 13  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
M  END


  Mrv0541 05061309172D          

 26 28  0  0  0  0            999 V2000
    4.5998   -2.9902    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
    4.7626    2.7825    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
    4.8437   -1.5822    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
    6.0553   -0.2390    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
    4.2341    2.1490    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
  6  1  1  0  0  0  0
 10  2  1  0  0  0  0
 10  6  2  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  4  2  0  0  0  0
 13  8  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 15  9  1  0  0  0  0
 16  8  1  0  0  0  0
 17 12  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 12  1  0  0  0  0
 20  5  1  0  0  0  0
 20  9  1  0  0  0  0
 20 16  1  0  0  0  0
 21 13  1  0  0  0  0
 22 18  2  0  0  0  0
 23 19  2  0  0  0  0
 24 14  1  0  0  0  0
 24 19  1  0  0  0  0
 25 15  1  0  0  0  0
 25 18  1  0  0  0  0
 26 16  1  0  0  0  0
 26 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036692

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O6/c1-6-10(2)18(22)25-15-9-20(5)16(26-20)8-13(21)11(3)7-14-17(15)12(4)19(23)24-14/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6+,11-7-

> <INCHI_KEY>
DZTWAOVNNLDWNH-QZTBCQRESA-N

> <FORMULA>
C20H26O6

> <MOLECULAR_WEIGHT>
362.4168

> <EXACT_MASS>
362.172938564

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
38.3612117426274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.45

> <JCHEM_LOGP>
2.406761494000001

> <ALOGPS_LOGS>
-3.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.528233765096555

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.216148242525895

> <JCHEM_PKA_STRONGEST_BASIC>
-3.006825452782963

> <JCHEM_POLAR_SURFACE_AREA>
85.36

> <JCHEM_REFRACTIVITY>
95.53569999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.96e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036692
     RDKit          3D
Heliangin
 52 54  0  0  0  0  0  0  0  0999 V2000
   -0.1689    3.9051   -0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9771    2.8970   -0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971    2.8421   -1.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7155    3.8543   -2.2476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6368    1.5078   -1.7314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683    0.7621   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5834   -0.6544   -1.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586   -1.3255   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594   -2.8373   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4330   -0.6346    0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6270   -1.4113    0.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9941   -0.7248    1.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7141   -1.4597    1.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2570   -1.1749    3.2239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860   -0.8816    1.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7464   -1.7667    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    0.5632    1.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1414    1.1433    0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549    0.5878    0.0111 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    1.0200   -0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7599    2.1320    0.2772 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5123    0.2191   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1839   -1.1235   -1.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625    0.6538   -0.9648 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7694   -0.1907   -1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0066    1.5368   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    3.8935   -0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    4.8347   -1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897    1.0750   -2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730   -1.2572   -1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370   -3.2044   -0.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -3.1437   -1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2191   -3.2410   -0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7619    0.3522   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2968   -1.0209    0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7616   -1.2629    2.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9648    0.2986    2.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -2.5679    1.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -1.2158    2.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508   -2.0502    0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -2.6940    2.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0029    1.1825    2.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    0.7276    2.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545    2.1378    0.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7568   -1.8633   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072   -1.3123   -1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5065   -1.2551   -2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0032    1.6440   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7598    0.0457   -2.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5409   -1.2681   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7612    0.0675   -1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8790    1.6580    0.5011 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
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 18 26  1  0
 26  2  1  0
 26  6  1  0
 15 13  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.586  -5.582   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       8.890   5.194   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.731  -1.876   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.199  -1.317   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.055  -4.136   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.938   3.486   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.917   2.829   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.979  -0.062   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       9.421   3.748   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.303  -0.446   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       7.904   4.011   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.993  -1.245   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      13.979  -1.055   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      12.899   1.468   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       9.497  -0.325   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.945   0.463   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5   20                                                            
CONECT    6    1   10                                                       
CONECT    7   11   14                                                       
CONECT    8   13   16                                                       
CONECT    9   15   20                                                       
CONECT   10    2    6   18                                                  
CONECT   11    3    7   13                                                  
CONECT   12    4   17   19                                                  
CONECT   13    8   11   21                                                  
CONECT   14    7   17   24                                                  
CONECT   15    9   17   25                                                  
CONECT   16    8   20   26                                                  
CONECT   17   12   14   15                                                  
CONECT   18   10   22   25                                                  
CONECT   19   12   23   24                                                  
CONECT   20    5    9   16   26                                             
CONECT   21   13                                                            
CONECT   22   18                                                            
CONECT   23   19                                                            
CONECT   24   14   19                                                       
CONECT   25   15   18                                                       
CONECT   26   16   20                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0036692
HETATM    1  C1  UNL     1      -0.169   3.905  -0.708  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.977   2.897  -0.825  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.197   2.842  -1.681  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.715   3.854  -2.248  1.00  0.00           O  
HETATM    5  O2  UNL     1      -2.637   1.508  -1.731  1.00  0.00           O  
HETATM    6  C4  UNL     1      -1.468   0.762  -1.372  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.583  -0.654  -1.338  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.459  -1.326  -0.640  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.459  -2.837  -0.706  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.433  -0.635   0.202  1.00  0.00           C  
HETATM   11  O3  UNL     1      -4.627  -1.411   0.097  1.00  0.00           O  
HETATM   12  C9  UNL     1      -2.994  -0.725   1.659  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.714  -1.460   1.825  1.00  0.00           C  
HETATM   14  O4  UNL     1      -1.257  -1.175   3.224  1.00  0.00           O  
HETATM   15  C11 UNL     1      -0.486  -0.882   1.964  1.00  0.00           C  
HETATM   16  C12 UNL     1       0.746  -1.767   2.002  1.00  0.00           C  
HETATM   17  C13 UNL     1      -0.216   0.563   1.947  1.00  0.00           C  
HETATM   18  C14 UNL     1       0.141   1.143   0.580  1.00  0.00           C  
HETATM   19  O5  UNL     1       1.255   0.588   0.011  1.00  0.00           O  
HETATM   20  C15 UNL     1       2.505   1.020  -0.152  1.00  0.00           C  
HETATM   21  O6  UNL     1       2.760   2.132   0.277  1.00  0.00           O  
HETATM   22  C16 UNL     1       3.512   0.219  -0.803  1.00  0.00           C  
HETATM   23  C17 UNL     1       3.184  -1.124  -1.315  1.00  0.00           C  
HETATM   24  C18 UNL     1       4.763   0.654  -0.965  1.00  0.00           C  
HETATM   25  C19 UNL     1       5.769  -0.191  -1.635  1.00  0.00           C  
HETATM   26  C20 UNL     1      -1.007   1.537  -0.214  1.00  0.00           C  
HETATM   27  H1  UNL     1       0.699   3.894  -0.076  1.00  0.00           H  
HETATM   28  H2  UNL     1      -0.329   4.835  -1.254  1.00  0.00           H  
HETATM   29  H3  UNL     1      -0.790   1.075  -2.245  1.00  0.00           H  
HETATM   30  H4  UNL     1      -0.873  -1.257  -1.952  1.00  0.00           H  
HETATM   31  H5  UNL     1      -1.437  -3.204  -0.483  1.00  0.00           H  
HETATM   32  H6  UNL     1      -2.674  -3.144  -1.751  1.00  0.00           H  
HETATM   33  H7  UNL     1      -3.219  -3.241  -0.035  1.00  0.00           H  
HETATM   34  H8  UNL     1      -3.762   0.352  -0.096  1.00  0.00           H  
HETATM   35  H9  UNL     1      -5.297  -1.021   0.716  1.00  0.00           H  
HETATM   36  H10 UNL     1      -3.762  -1.263   2.259  1.00  0.00           H  
HETATM   37  H11 UNL     1      -2.965   0.299   2.138  1.00  0.00           H  
HETATM   38  H12 UNL     1      -1.826  -2.568   1.793  1.00  0.00           H  
HETATM   39  H13 UNL     1       1.614  -1.216   2.405  1.00  0.00           H  
HETATM   40  H14 UNL     1       0.951  -2.050   0.928  1.00  0.00           H  
HETATM   41  H15 UNL     1       0.617  -2.694   2.546  1.00  0.00           H  
HETATM   42  H16 UNL     1      -1.003   1.183   2.426  1.00  0.00           H  
HETATM   43  H17 UNL     1       0.708   0.728   2.577  1.00  0.00           H  
HETATM   44  H18 UNL     1       0.555   2.138   0.898  1.00  0.00           H  
HETATM   45  H19 UNL     1       3.757  -1.863  -0.691  1.00  0.00           H  
HETATM   46  H20 UNL     1       2.107  -1.312  -1.216  1.00  0.00           H  
HETATM   47  H21 UNL     1       3.507  -1.255  -2.373  1.00  0.00           H  
HETATM   48  H22 UNL     1       5.003   1.644  -0.587  1.00  0.00           H  
HETATM   49  H23 UNL     1       5.760   0.046  -2.724  1.00  0.00           H  
HETATM   50  H24 UNL     1       5.541  -1.268  -1.528  1.00  0.00           H  
HETATM   51  H25 UNL     1       6.761   0.068  -1.195  1.00  0.00           H  
HETATM   52  H26 UNL     1      -1.879   1.658   0.501  1.00  0.00           H  
CONECT    1    2    2   27   28
CONECT    2    3   26
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   26   29
CONECT    7    8    8   30
CONECT    8    9   10
CONECT    9   31   32   33
CONECT   10   11   12   34
CONECT   11   35
CONECT   12   13   36   37
CONECT   13   14   15   38
CONECT   14   15
CONECT   15   16   17
CONECT   16   39   40   41
CONECT   17   18   42   43
CONECT   18   19   26   44
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   23   24   24
CONECT   23   45   46   47
CONECT   24   25   48
CONECT   25   49   50   51
CONECT   26   52
END

HMDB0036692
     RDKit          3D
Heliangin
 52 54  0  0  0  0  0  0  0  0999 V2000
   -0.1689    3.9051   -0.7082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9771    2.8970   -0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1971    2.8421   -1.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7155    3.8543   -2.2476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6368    1.5078   -1.7314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683    0.7621   -1.3717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5834   -0.6544   -1.3376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586   -1.3255   -0.6401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4594   -2.8373   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4330   -0.6346    0.2019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6270   -1.4113    0.0973 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9941   -0.7248    1.6590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7141   -1.4597    1.8249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2570   -1.1749    3.2239 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4860   -0.8816    1.9636 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7464   -1.7667    2.0021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2158    0.5632    1.9469 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1414    1.1433    0.5802 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2549    0.5878    0.0111 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5045    1.0200   -0.1520 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7599    2.1320    0.2772 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5123    0.2191   -0.8027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1839   -1.1235   -1.3151 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625    0.6538   -0.9648 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7694   -0.1907   -1.6350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0066    1.5368   -0.2144 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6989    3.8935   -0.0758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    4.8347   -1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897    1.0750   -2.2448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8730   -1.2572   -1.9518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4370   -3.2044   -0.4834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6745   -3.1437   -1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2191   -3.2410   -0.0353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7619    0.3522   -0.0963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2968   -1.0209    0.7157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7616   -1.2629    2.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9648    0.2986    2.1380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8259   -2.5679    1.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6136   -1.2158    2.4048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9508   -2.0502    0.9278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -2.6940    2.5460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0029    1.1825    2.4258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7076    0.7276    2.5766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545    2.1378    0.8982 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7568   -1.8633   -0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1072   -1.3123   -1.2161 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5065   -1.2551   -2.3733 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0032    1.6440   -0.5865 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7598    0.0457   -2.7236 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5409   -1.2681   -1.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7612    0.0675   -1.1954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8790    1.6580    0.5011 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
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  2  0
 24 25  1  0
 18 26  1  0
 26  2  1  0
 26  6  1  0
 15 13  1  0
  1 27  1  0
  1 28  1  0
  6 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 12 37  1  0
 13 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  0
 23 45  1  0
 23 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 26 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Heliangine	HMDB
Leptocarpin	HMDB
(9Z)-8-Hydroxy-4,9-dimethyl-14-methylidene-13-oxo-5,12-dioxatricyclo[9.3.0.0⁴,⁶]tetradec-9-en-2-yl (2E)-2-methylbut-2-enoic acid	Generator
Heliangin	MeSH
Leptocarpin, (1ar-(1ar,3S,4Z,5ar,8ar,9R(e),10ar))-isomer	MeSH
Leptocarpin, (1ar-(1ar,3S,4Z,5as,8ar,9S,10ar))-isomer	MeSH

Chemical Formula

C₂₀H₂₆O₆

Average Molecular Weight

362.4168

Monoisotopic Molecular Weight

362.172938564

IUPAC Name

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

Traditional Name

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

CAS Registry Number

13323-48-3

SMILES

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

InChI Identifier

InChI=1S/C20H26O6/c1-6-10(2)18(22)25-15-9-20(5)16(26-20)8-13(21)11(3)7-14-17(15)12(4)19(23)24-14/h6-7,13-17,21H,4,8-9H2,1-3,5H3/b10-6+,11-7-

InChI Key

DZTWAOVNNLDWNH-QZTBCQRESA-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
Secondary alcohol
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036692)

Source

Endogenous

Endogenous (HMDB: HMDB0036692)

Plant

Plant (HMDB: HMDB0036692)

Animal

Animal (HMDB: HMDB0036692)

Exogenous

Food

Food (HMDB: HMDB0036692)

Vegetable

Tuber

Jerusalem artichoke (FooDB: FOOD00387)

Leaf vegetable

Spinach (FooDB: FOOD00178)

Root vegetable

Root vegetables (FooDB: FOOD00873)

Herb and spice

Oilseed crop

Sunflower (FooDB: FOOD00086)

Exogenous (HMDB: HMDB0036692)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036692)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036692)

Lipid metabolism pathway (HMDB: HMDB0036692)

Cellular process

Cell signaling (HMDB: HMDB0036692)

Biochemical process

Lipid transport (HMDB: HMDB0036692)

Role

Biological role

Energy source (HMDB: HMDB0036692)
Phytohormonal (HMDB: HMDB0036692)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036692)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	227 - 229 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.3 g/L	ALOGPS
logP	1.45	ALOGPS
logP	2.41	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	6.22	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	85.36 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	95.54 m³·mol⁻¹	ChemAxon
Polarizability	38.36 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]+	185.791	31661259
DarkChem	[M-H]-	182.261	31661259
DeepCCS	[M-2H]-	221.702	30932474
DeepCCS	[M+Na]+	196.93	30932474
AllCCS	[M+H]+	188.1	32859911
AllCCS	[M+H-H2O]+	185.4	32859911
AllCCS	[M+NH4]+	190.6	32859911
AllCCS	[M+Na]+	191.3	32859911
AllCCS	[M-H]-	189.8	32859911
AllCCS	[M+Na-2H]-	190.1	32859911
AllCCS	[M+HCOO]-	190.6	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.	7.13 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4594 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.69 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2674.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	196.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	142.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	152.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	64.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	457.3 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	475.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	104.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	981.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	446.0 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	1299.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	319.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	322.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	313.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	155.6 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	34.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Heliangin	C\C=C(/C)C(=O)OC1CC2(C)OC2CC(O)\C(C)=C/C2OC(=O)C(=C)C12	3848.6	Standard polar	33892256
Heliangin	C\C=C(/C)C(=O)OC1CC2(C)OC2CC(O)\C(C)=C/C2OC(=O)C(=C)C12	2541.1	Standard non polar	33892256
Heliangin	C\C=C(/C)C(=O)OC1CC2(C)OC2CC(O)\C(C)=C/C2OC(=O)C(=C)C12	2762.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Heliangin,1TMS,isomer #1	C=C1C(=O)OC2/C=C(/C)C(O[Si](C)(C)C)CC3OC3(C)CC(OC(=O)/C(C)=C/C)C12	2684.1	Semi standard non polar	33892256
Heliangin,1TBDMS,isomer #1	C=C1C(=O)OC2/C=C(/C)C(O[Si](C)(C)C(C)(C)C)CC3OC3(C)CC(OC(=O)/C(C)=C/C)C12	2905.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Heliangin GC-MS (Non-derivatized) - 70eV, Positive	splash10-053s-9014000000-d4115525398926b17407	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliangin GC-MS (1 TMS) - 70eV, Positive	splash10-053r-9001100000-6a89a281481d94379912	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Heliangin 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 - Heliangin 10V, Positive-QTOF	splash10-03dj-2039000000-785f137b68ea1b583520	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliangin 20V, Positive-QTOF	splash10-06us-9184000000-645c0c1af1c3e2495ce8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliangin 40V, Positive-QTOF	splash10-0f89-9120000000-35228986d558858a4334	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliangin 10V, Negative-QTOF	splash10-03di-0019000000-399bd5ed523ca36c8d99	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliangin 20V, Negative-QTOF	splash10-0901-5049000000-604186f0c012089dab02	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliangin 40V, Negative-QTOF	splash10-0f81-9550000000-3dfd2150bf626a73e577	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliangin 10V, Negative-QTOF	splash10-03di-2092000000-a2107e87fa08cd77bbc5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliangin 20V, Negative-QTOF	splash10-01ot-9060000000-90926566628c185acbff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliangin 40V, Negative-QTOF	splash10-03di-2090000000-7d965b00d72ca32904cf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliangin 10V, Positive-QTOF	splash10-03di-0090000000-be4f1c6baa4bb8ca15a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliangin 20V, Positive-QTOF	splash10-0002-0094000000-6fae0e8f2a70227265cd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Heliangin 40V, Positive-QTOF	splash10-052b-7098000000-677ea1d7babf76468eb6	2021-09-22	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

FDB015624

KNApSAcK ID

C00000235

Chemspider ID

28532736

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5838160

PDB ID

Not Available

ChEBI ID

5638

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1856511

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 Heliangin (HMDB0036692)

MOL for HMDB0036692 (Heliangin)

3D MOL for HMDB0036692 (Heliangin)

3D SDF for HMDB0036692 (Heliangin)

3D-SDF for HMDB0036692 (Heliangin)

PDB for HMDB0036692 (Heliangin)

3D PDB for HMDB0036692 (Heliangin)

SMILES for HMDB0036692 (Heliangin)

INCHI for HMDB0036692 (Heliangin)

Structure for HMDB0036692 (Heliangin)

3D Structure for HMDB0036692 (Heliangin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra