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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:06:47 UTC

Update Date

2022-03-07 02:56:16 UTC

HMDB ID

HMDB0039607

Secondary Accession Numbers

HMDB39607

Metabolite Identification

Common Name

Sorgolactone

Description

Sorgolactone is found in cereals and cereal products. Sorgolactone is isolated from the roots of Sorghum bicolor (sorghum) (genuine host plant for Striga species) Strigolactones are plant hormones that have been implicated in inhibition of shoot branching. Strigolactones are carotenoid-derived and trigger germination of parasitic plant seeds (for example striga from which they gained their name) and stimulate symbiotic mycorrhizal fungi. Strigolactones contain a labile ether bond that is easily hydrolysed in the rhizosphere meaning that there is a large concentration gradient between areas near the root and those further away.

Structure

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

HMDB0039607
     RDKit          3D
Sorgolactone
 43 46  0  0  0  0  0  0  0  0999 V2000
    7.5316    0.8534    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2422    0.1635    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2896   -0.2169    1.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2224   -0.8450    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0717    0.0105    0.3389 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -0.4345   -0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751    0.0804   -0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4692    1.1000    0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2662    1.5617    1.8430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656    1.4614    0.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400    0.9520   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7131    0.3889   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -0.7568    0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110   -1.3127    0.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8507   -1.4212   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0517   -0.2088   -0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0609    0.8846   -0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5573    2.0071    0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959   -1.2831    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5126   -0.2815   -0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6174   -0.8078   -1.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8504   -0.1959   -1.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5598    0.0361   -2.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3446    1.9527    0.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2398    0.7773   -0.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9384    0.4391    1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2818   -0.0915    2.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9636   -1.8694    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9754   -1.1875   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2528    1.6768   -1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1374   -0.6308    1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6372   -2.3389    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8040   -1.7618    0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5429   -2.3004   -0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0657    0.2173   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1505   -0.5323   -2.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    1.3285   -1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6116    1.7688    0.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0016    2.0683    1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617    2.9875   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275   -1.3631    1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2338   -2.2531   -0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4338   -0.6227   -1.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 19  1  0
 19 20  1  0
  4 21  1  0
 21 22  1  0
 22 23  2  0
 22  2  1  0
 20  7  1  0
 20 11  1  0
 17 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
M  END

  Mrv0541 05061311162D          

 23 26  0  0  0  0            999 V2000
    4.2139    3.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7300   -0.7904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4962    1.7974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2568    2.5869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9322    1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6701    0.2284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4519    0.9110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4713    0.7675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4534    2.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9405   -0.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1288    1.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7942    1.4090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9693    1.4253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1547    0.2122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8894    2.1722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0645    2.1885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2827   -1.0490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7299    2.2148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2990   -1.8738    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505    2.4851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6527    0.8699    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3941   -0.5773    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4068    2.6864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  0  0  0  0
  9  1  1  0  0  0  0
  9  4  1  0  0  0  0
 10  2  1  0  0  0  0
 10  6  2  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  7  1  0  0  0  0
 13  8  2  0  0  0  0
 13 12  1  0  0  0  0
 14  6  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 16 15  1  0  0  0  0
 17 10  1  0  0  0  0
 18 13  1  0  0  0  0
 19 17  2  0  0  0  0
 20 18  2  0  0  0  0
 21  8  1  0  0  0  0
 21 14  1  0  0  0  0
 22 14  1  0  0  0  0
 22 17  1  0  0  0  0
 23 16  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039607

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCCC2=C1C1OC(=O)\C(=C/OC3OC(=O)C(C)=C3)C1C2

> <INCHI_IDENTIFIER>
InChI=1S/C18H20O5/c1-9-4-3-5-11-7-12-13(18(20)23-16(12)15(9)11)8-21-14-6-10(2)17(19)22-14/h6,8-9,12,14,16H,3-5,7H2,1-2H3/b13-8-

> <INCHI_KEY>
KHSREFIWULNDAB-JYRVWZFOSA-N

> <FORMULA>
C18H20O5

> <MOLECULAR_WEIGHT>
316.3484

> <EXACT_MASS>
316.13107375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
33.59114712216118

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-methyl-5-{[(3Z)-8-methyl-2-oxo-2H,3H,3aH,4H,5H,6H,7H,8H,8bH-indeno[1,2-b]furan-3-ylidene]methoxy}-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
3.276609625333333

> <ALOGPS_LOGS>
-3.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.198836742274235

> <JCHEM_PKA_STRONGEST_BASIC>
-4.94057346629833

> <JCHEM_POLAR_SURFACE_AREA>
61.83000000000001

> <JCHEM_REFRACTIVITY>
82.87519999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.76e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-methyl-5-{[(3Z)-8-methyl-2-oxo-3aH,4H,5H,6H,7H,8H,8bH-indeno[1,2-b]furan-3-ylidene]methoxy}-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039607
     RDKit          3D
Sorgolactone
 43 46  0  0  0  0  0  0  0  0999 V2000
    7.5316    0.8534    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2422    0.1635    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2896   -0.2169    1.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2224   -0.8450    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0717    0.0105    0.3389 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -0.4345   -0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751    0.0804   -0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4692    1.1000    0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2662    1.5617    1.8430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656    1.4614    0.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400    0.9520   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7131    0.3889   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -0.7568    0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110   -1.3127    0.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8507   -1.4212   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0517   -0.2088   -0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0609    0.8846   -0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5573    2.0071    0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959   -1.2831    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5126   -0.2815   -0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6174   -0.8078   -1.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8504   -0.1959   -1.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5598    0.0361   -2.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3446    1.9527    0.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2398    0.7773   -0.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9384    0.4391    1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2818   -0.0915    2.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9636   -1.8694    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9754   -1.1875   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2528    1.6768   -1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1374   -0.6308    1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6372   -2.3389    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8040   -1.7618    0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5429   -2.3004   -0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0657    0.2173   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1505   -0.5323   -2.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    1.3285   -1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6116    1.7688    0.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0016    2.0683    1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617    2.9875   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275   -1.3631    1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2338   -2.2531   -0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4338   -0.6227   -1.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 19  1  0
 19 20  1  0
  4 21  1  0
 21 22  1  0
 22 23  2  0
 22  2  1  0
 20  7  1  0
 20 11  1  0
 17 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  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       7.866   6.652   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.229  -1.475   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.260   3.355   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.813   4.829   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.207   2.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.251   0.426   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.444   1.701   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.746   1.433   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.313   5.179   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.756  -1.029   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.707   2.581   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.216   2.630   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.676   2.661   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.289   0.396   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.260   4.055   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.720   4.085   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.528  -1.958   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.229   4.134   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.558  -3.498   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.774   4.639   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.218   1.624   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       0.736  -1.078   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.493   5.015   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3    4    5                                                       
CONECT    4    3    9                                                       
CONECT    5    3   11                                                       
CONECT    6   10   14                                                       
CONECT    7   11   12                                                       
CONECT    8   13   21                                                       
CONECT    9    1    4   15                                                  
CONECT   10    2    6   17                                                  
CONECT   11    5    7   15                                                  
CONECT   12    7   13   16                                                  
CONECT   13    8   12   18                                                  
CONECT   14    6   21   22                                                  
CONECT   15    9   11   16                                                  
CONECT   16   12   15   23                                                  
CONECT   17   10   19   22                                                  
CONECT   18   13   20   23                                                  
CONECT   19   17                                                            
CONECT   20   18                                                            
CONECT   21    8   14                                                       
CONECT   22   14   17                                                       
CONECT   23   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0039607
HETATM    1  C1  UNL     1       7.532   0.853   0.537  1.00  0.00           C  
HETATM    2  C2  UNL     1       6.242   0.163   0.192  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.290  -0.217   1.013  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.222  -0.845   0.251  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.072   0.010   0.339  1.00  0.00           O  
HETATM    6  C5  UNL     1       1.940  -0.434  -0.338  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.775   0.080  -0.026  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.469   1.100   0.972  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.266   1.562   1.843  1.00  0.00           O  
HETATM   10  O3  UNL     1      -0.866   1.461   0.777  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.340   0.952  -0.448  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.713   0.389  -0.340  1.00  0.00           C  
HETATM   13  C10 UNL     1      -2.585  -0.757   0.306  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.811  -1.313   0.940  1.00  0.00           C  
HETATM   15  C12 UNL     1      -4.851  -1.421  -0.142  1.00  0.00           C  
HETATM   16  C13 UNL     1      -5.052  -0.209  -0.963  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.061   0.885  -0.807  1.00  0.00           C  
HETATM   18  C15 UNL     1      -4.557   2.007   0.072  1.00  0.00           C  
HETATM   19  C16 UNL     1      -1.196  -1.283   0.265  1.00  0.00           C  
HETATM   20  C17 UNL     1      -0.513  -0.281  -0.647  1.00  0.00           C  
HETATM   21  O4  UNL     1       4.617  -0.808  -1.091  1.00  0.00           O  
HETATM   22  C18 UNL     1       5.850  -0.196  -1.159  1.00  0.00           C  
HETATM   23  O5  UNL     1       6.560   0.036  -2.197  1.00  0.00           O  
HETATM   24  H1  UNL     1       7.345   1.953   0.695  1.00  0.00           H  
HETATM   25  H2  UNL     1       8.240   0.777  -0.301  1.00  0.00           H  
HETATM   26  H3  UNL     1       7.938   0.439   1.462  1.00  0.00           H  
HETATM   27  H4  UNL     1       5.282  -0.092   2.089  1.00  0.00           H  
HETATM   28  H5  UNL     1       3.964  -1.869   0.597  1.00  0.00           H  
HETATM   29  H6  UNL     1       1.975  -1.187  -1.111  1.00  0.00           H  
HETATM   30  H7  UNL     1      -1.253   1.677  -1.280  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.137  -0.631   1.735  1.00  0.00           H  
HETATM   32  H9  UNL     1      -3.637  -2.339   1.325  1.00  0.00           H  
HETATM   33  H10 UNL     1      -5.804  -1.762   0.353  1.00  0.00           H  
HETATM   34  H11 UNL     1      -4.543  -2.300  -0.781  1.00  0.00           H  
HETATM   35  H12 UNL     1      -6.066   0.217  -0.707  1.00  0.00           H  
HETATM   36  H13 UNL     1      -5.151  -0.532  -2.041  1.00  0.00           H  
HETATM   37  H14 UNL     1      -3.874   1.329  -1.815  1.00  0.00           H  
HETATM   38  H15 UNL     1      -5.612   1.769   0.327  1.00  0.00           H  
HETATM   39  H16 UNL     1      -4.002   2.068   1.029  1.00  0.00           H  
HETATM   40  H17 UNL     1      -4.562   2.988  -0.451  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.727  -1.363   1.245  1.00  0.00           H  
HETATM   42  H19 UNL     1      -1.234  -2.253  -0.290  1.00  0.00           H  
HETATM   43  H20 UNL     1      -0.434  -0.623  -1.676  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    3   22
CONECT    3    4   27
CONECT    4    5   21   28
CONECT    5    6
CONECT    6    7    7   29
CONECT    7    8   20
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   20   30
CONECT   12   13   13   17
CONECT   13   14   19
CONECT   14   15   31   32
CONECT   15   16   33   34
CONECT   16   17   35   36
CONECT   17   18   37
CONECT   18   38   39   40
CONECT   19   20   41   42
CONECT   20   43
CONECT   21   22
CONECT   22   23   23
END

HMDB0039607
     RDKit          3D
Sorgolactone
 43 46  0  0  0  0  0  0  0  0999 V2000
    7.5316    0.8534    0.5373 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2422    0.1635    0.1918 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2896   -0.2169    1.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2224   -0.8450    0.2511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0717    0.0105    0.3389 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -0.4345   -0.3379 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7751    0.0804   -0.0261 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4692    1.1000    0.9722 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2662    1.5617    1.8430 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8656    1.4614    0.7772 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3400    0.9520   -0.4479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7131    0.3889   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5855   -0.7568    0.3059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8110   -1.3127    0.9401 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8507   -1.4212   -0.1425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0517   -0.2088   -0.9635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0609    0.8846   -0.8074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5573    2.0071    0.0722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1959   -1.2831    0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5126   -0.2815   -0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6174   -0.8078   -1.0908 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8504   -0.1959   -1.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5598    0.0361   -2.1965 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3446    1.9527    0.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2398    0.7773   -0.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9384    0.4391    1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2818   -0.0915    2.0890 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9636   -1.8694    0.5973 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9754   -1.1875   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2528    1.6768   -1.2800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1374   -0.6308    1.7353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6372   -2.3389    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8040   -1.7618    0.3529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5429   -2.3004   -0.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0657    0.2173   -0.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1505   -0.5323   -2.0409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8740    1.3285   -1.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6116    1.7688    0.3273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0016    2.0683    1.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5617    2.9875   -0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7275   -1.3631    1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2338   -2.2531   -0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4338   -0.6227   -1.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 19  1  0
 19 20  1  0
  4 21  1  0
 21 22  1  0
 22 23  2  0
 22  2  1  0
 20  7  1  0
 20 11  1  0
 17 12  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  4 28  1  0
  6 29  1  0
 11 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₈H₂₀O₅

Average Molecular Weight

316.3484

Monoisotopic Molecular Weight

316.13107375

IUPAC Name

3-methyl-5-{[(3Z)-8-methyl-2-oxo-2H,3H,3aH,4H,5H,6H,7H,8H,8bH-indeno[1,2-b]furan-3-ylidene]methoxy}-2,5-dihydrofuran-2-one

Traditional Name

3-methyl-5-{[(3Z)-8-methyl-2-oxo-3aH,4H,5H,6H,7H,8H,8bH-indeno[1,2-b]furan-3-ylidene]methoxy}-5H-furan-2-one

CAS Registry Number

141262-39-7

SMILES

CC1CCCC2=C1C1OC(=O)\C(=C/OC3OC(=O)C(C)=C3)C1C2

InChI Identifier

InChI=1S/C18H20O5/c1-9-4-3-5-11-7-12-13(18(20)23-16(12)15(9)11)8-21-14-6-10(2)17(19)22-14/h6,8-9,12,14,16H,3-5,7H2,1-2H3/b13-8-

InChI Key

KHSREFIWULNDAB-JYRVWZFOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as strigolactones. These are terpene lactones structurally characterized by the presence of an indeno[1,2-b]furan and a 2,5-dihydrofuran-2-one linked together to form a 3-methyl-5-{8-methyl-2-oxo-indeno[1,2-b]furan-3-ylidene]methoxy}-2,5-dihydrofuran-2-one skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Strigolactones

Alternative Parents

Substituents

Strigolactone
2-furanone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Dihydrofuran
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Oxacycle
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
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: HMDB0039607)

Source

Endogenous

Endogenous (HMDB: HMDB0039607)

Plant

Poaceae (HMDB: HMDB0039607)

Animal

Animal (HMDB: HMDB0039607)

Exogenous

Food

Food (HMDB: HMDB0039607)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereal

Sorghum (FooDB: FOOD00177)

Cereals and cereal products (FooDB: FOOD00858)

Exogenous (HMDB: HMDB0039607)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0039607)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0039607)

Lipid metabolism pathway (HMDB: HMDB0039607)

Cellular process

Cell signaling (HMDB: HMDB0039607)

Biochemical process

Lipid transport (HMDB: HMDB0039607)

Role

Biological role

Energy source (HMDB: HMDB0039607)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039607)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	139 - 142 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	56.96 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.088 g/L	ALOGPS
logP	2.84	ALOGPS
logP	3.28	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	15.2	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	61.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.88 m³·mol⁻¹	ChemAxon
Polarizability	33.59 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
DarkChem	[M+H]+	173.02	31661259
DarkChem	[M-H]-	170.842	31661259
DeepCCS	[M+H]+	179.956	30932474
DeepCCS	[M-H]-	177.515	30932474
DeepCCS	[M-2H]-	211.95	30932474
DeepCCS	[M+Na]+	188.211	30932474
AllCCS	[M+H]+	175.6	32859911
AllCCS	[M+H-H2O]+	172.5	32859911
AllCCS	[M+NH4]+	178.6	32859911
AllCCS	[M+Na]+	179.4	32859911
AllCCS	[M-H]-	178.2	32859911
AllCCS	[M+Na-2H]-	178.0	32859911
AllCCS	[M+HCOO]-	177.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sorgolactone	CC1CCCC2=C1C1OC(=O)\C(=C/OC3OC(=O)C(C)=C3)C1C2	3517.7	Standard polar	33892256
Sorgolactone	CC1CCCC2=C1C1OC(=O)\C(=C/OC3OC(=O)C(C)=C3)C1C2	2644.7	Standard non polar	33892256
Sorgolactone	CC1CCCC2=C1C1OC(=O)\C(=C/OC3OC(=O)C(C)=C3)C1C2	2803.8	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 - Sorgolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fk9-7790000000-be3cc93ca40e046dc606	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sorgolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sorgolactone 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 - Sorgolactone 10V, Positive-QTOF	splash10-0uxu-1393000000-f5919a1eec109b201d5c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sorgolactone 20V, Positive-QTOF	splash10-0udi-8690000000-32e64c360041dac42003	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sorgolactone 40V, Positive-QTOF	splash10-00kf-9310000000-8a106779cf7ce5e88f81	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sorgolactone 10V, Negative-QTOF	splash10-014i-3296000000-3d3649a1f8a9f6899f80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sorgolactone 20V, Negative-QTOF	splash10-03y1-9871000000-5553b98954c347420696	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sorgolactone 40V, Negative-QTOF	splash10-000b-9410000000-59c100dcaa69de274e87	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sorgolactone 10V, Negative-QTOF	splash10-014i-0129000000-c6bcafcc571e7c92bebc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sorgolactone 20V, Negative-QTOF	splash10-014i-1191000000-8d98d394275ffde0f468	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sorgolactone 40V, Negative-QTOF	splash10-029i-7960000000-ae0e38fa02a3301d4016	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sorgolactone 10V, Positive-QTOF	splash10-014i-0039000000-fd450661b5cb073f6994	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sorgolactone 20V, Positive-QTOF	splash10-014j-4296000000-b6ddf7c157ae44be1986	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sorgolactone 40V, Positive-QTOF	splash10-003r-2950000000-43868db7aa53b7ecf072	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Strigolactone

METLIN ID

Not Available

PubChem Compound

131752688

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1878761

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 ]
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Showing metabocard for Sorgolactone (HMDB0039607)

MOL for HMDB0039607 (Sorgolactone)

3D MOL for HMDB0039607 (Sorgolactone)

3D SDF for HMDB0039607 (Sorgolactone)

3D-SDF for HMDB0039607 (Sorgolactone)

PDB for HMDB0039607 (Sorgolactone)

3D PDB for HMDB0039607 (Sorgolactone)

SMILES for HMDB0039607 (Sorgolactone)

INCHI for HMDB0039607 (Sorgolactone)

Structure for HMDB0039607 (Sorgolactone)

3D Structure for HMDB0039607 (Sorgolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra