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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:50:40 UTC

Update Date

2022-03-07 02:55:01 UTC

HMDB ID

HMDB0036677

Secondary Accession Numbers

HMDB36677

Metabolite Identification

Common Name

Strigol

Description

Strigol is found in corn. Strigol is a constituent of the root of Gossypium hirsutum (cotton) 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

HMDB0036677
     RDKit          3D
Strigol
 47 50  0  0  0  0  0  0  0  0999 V2000
    7.0122   -0.6199    1.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9709    0.0369    0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7368    0.3366    1.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0704    0.9712    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0119    0.1613   -0.3321 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2569    0.5866   -1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9416    0.3136   -1.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0022    0.6836   -2.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196    1.6620   -3.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0315   -0.2400   -2.4027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046   -0.9429   -1.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538   -0.5375   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8730    0.5705    0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117    0.6014    0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -0.3975   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839    1.5450    0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171    2.8461    0.4485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1733    1.3235   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132   -0.0802   -0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5144   -1.1191   -0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6640   -2.3016   -1.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7246   -1.5758    1.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406    1.0134   -0.8679 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2048    0.4494   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2649    0.3431   -1.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3915   -1.5077    1.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5524   -0.8458    2.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8712    0.0931    1.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2681    0.1441    2.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677    1.9794    0.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6890    1.1251   -2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9395   -2.0391   -1.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762    0.2790    1.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0022    1.6220    0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385   -1.1982    0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1725    1.4573    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0724    2.9130   -0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0653    1.9048   -1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0631    1.7989    0.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853   -0.1937   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4899   -0.3788   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8742   -1.9363   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546   -2.9266   -1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5221   -2.9271   -0.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5552   -0.9489    1.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1078   -2.6192    1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316   -1.4251    1.9325 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
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  4 23  1  0
 23 24  1  0
 24 25  2  0
 24  2  1  0
 15  7  1  0
 15 11  1  0
 20 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  6 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
M  END


  Mrv0541 05061309162D          

 25 28  0  0  0  0            999 V2000
   -0.5907   -1.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7774    3.5330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7625    3.2252    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
    0.4691   -0.6341    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
    0.1988   -1.4135    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
    4.1288    1.3827    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
    4.9322    1.1953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2940   -0.6504    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
    0.8565   -1.9115    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
    4.4534    2.7743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1716    0.4058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8403   -2.7364    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
    1.7920    0.0074    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5334   -1.4399    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
  5  4  1  0  0  0  0
  9  1  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 12  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  4  1  0  0  0  0
 13 11  1  0  0  0  0
 14  6  1  0  0  0  0
 15 11  2  0  0  0  0
 16 10  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 12  1  0  0  0  0
 19  2  1  0  0  0  0
 19  3  1  0  0  0  0
 19  5  1  0  0  0  0
 19 15  1  0  0  0  0
 20 13  1  0  0  0  0
 21 17  2  0  0  0  0
 22 18  2  0  0  0  0
 23  8  1  0  0  0  0
 23 14  1  0  0  0  0
 24 14  1  0  0  0  0
 24 17  1  0  0  0  0
 25 16  1  0  0  0  0
 25 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036677

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC(O\C=C2/C3CC4=C(C3OC2=O)C(C)(C)CCC4O)OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C19H22O6/c1-9-6-14(24-17(9)21)23-8-12-10-7-11-13(20)4-5-19(2,3)15(11)16(10)25-18(12)22/h6,8,10,13-14,16,20H,4-5,7H2,1-3H3/b12-8+

> <INCHI_KEY>
VOFXXOPWCBSPAA-XYOKQWHBSA-N

> <FORMULA>
C19H22O6

> <MOLECULAR_WEIGHT>
346.3744

> <EXACT_MASS>
346.141638436

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.74850255104129

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.345845678333333

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.294090818315109

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.4931786246586

> <JCHEM_PKA_STRONGEST_BASIC>
-2.978819564005555

> <JCHEM_POLAR_SURFACE_AREA>
82.06

> <JCHEM_REFRACTIVITY>
88.8658

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036677
     RDKit          3D
Strigol
 47 50  0  0  0  0  0  0  0  0999 V2000
    7.0122   -0.6199    1.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9709    0.0369    0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7368    0.3366    1.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0704    0.9712    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0119    0.1613   -0.3321 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2569    0.5866   -1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9416    0.3136   -1.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0022    0.6836   -2.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196    1.6620   -3.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0315   -0.2400   -2.4027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046   -0.9429   -1.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538   -0.5375   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8730    0.5705    0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117    0.6014    0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -0.3975   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839    1.5450    0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171    2.8461    0.4485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1733    1.3235   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132   -0.0802   -0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5144   -1.1191   -0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6640   -2.3016   -1.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7246   -1.5758    1.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406    1.0134   -0.8679 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2048    0.4494   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2649    0.3431   -1.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3915   -1.5077    1.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5524   -0.8458    2.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8712    0.0931    1.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2681    0.1441    2.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677    1.9794    0.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6890    1.1251   -2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9395   -2.0391   -1.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762    0.2790    1.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0022    1.6220    0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385   -1.1982    0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1725    1.4573    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0724    2.9130   -0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0653    1.9048   -1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0631    1.7989    0.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853   -0.1937   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4899   -0.3788   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8742   -1.9363   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546   -2.9266   -1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5221   -2.9271   -0.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5552   -0.9489    1.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1078   -2.6192    1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316   -1.4251    1.9325 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
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  4 23  1  0
 23 24  1  0
 24 25  2  0
 24  2  1  0
 15  7  1  0
 15 11  1  0
 20 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  6 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  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      -1.103  -3.086   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.918   6.595   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.023   6.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.260   3.355   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.813   4.829   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.876  -1.184   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       0.371  -2.639   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.216   2.630   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       3.676   2.661   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.207   2.231   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.415  -1.214   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       1.599  -3.568   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  C   UNK     0       8.313   5.179   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       9.654   0.757   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.569  -5.108   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.774   4.639   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       3.345   0.014   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       2.862  -2.688   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       4.493   5.015   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2   19                                                            
CONECT    3   19                                                            
CONECT    4    5   13                                                       
CONECT    5    4   19                                                       
CONECT    6    9   14                                                       
CONECT    7   10   11                                                       
CONECT    8   12   23                                                       
CONECT    9    1    6   17                                                  
CONECT   10    7   12   16                                                  
CONECT   11    7   13   15                                                  
CONECT   12    8   10   18                                                  
CONECT   13    4   11   20                                                  
CONECT   14    6   23   24                                                  
CONECT   15   11   16   19                                                  
CONECT   16   10   15   25                                                  
CONECT   17    9   21   24                                                  
CONECT   18   12   22   25                                                  
CONECT   19    2    3    5   15                                             
CONECT   20   13                                                            
CONECT   21   17                                                            
CONECT   22   18                                                            
CONECT   23    8   14                                                       
CONECT   24   14   17                                                       
CONECT   25   16   18                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0036677
HETATM    1  C1  UNL     1       7.012  -0.620   1.849  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.971   0.037   0.987  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.737   0.337   1.297  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.070   0.971   0.149  1.00  0.00           C  
HETATM    5  O1  UNL     1       3.012   0.161  -0.332  1.00  0.00           O  
HETATM    6  C5  UNL     1       2.257   0.587  -1.416  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.942   0.314  -1.418  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.002   0.684  -2.471  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.120   1.662  -3.284  1.00  0.00           O  
HETATM   10  O3  UNL     1      -1.032  -0.240  -2.403  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.005  -0.943  -1.177  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.154  -0.538  -0.340  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.873   0.571   0.319  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.412   0.601   0.573  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.166  -0.397  -0.396  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.984   1.545   0.681  1.00  0.00           C  
HETATM   17  O4  UNL     1      -2.517   2.846   0.448  1.00  0.00           O  
HETATM   18  C14 UNL     1      -4.173   1.324  -0.186  1.00  0.00           C  
HETATM   19  C15 UNL     1      -4.513  -0.080  -0.519  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.514  -1.119  -0.123  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.664  -2.302  -1.081  1.00  0.00           C  
HETATM   22  C18 UNL     1      -3.725  -1.576   1.311  1.00  0.00           C  
HETATM   23  O5  UNL     1       5.041   1.013  -0.868  1.00  0.00           O  
HETATM   24  C19 UNL     1       6.205   0.449  -0.378  1.00  0.00           C  
HETATM   25  O6  UNL     1       7.265   0.343  -1.066  1.00  0.00           O  
HETATM   26  H1  UNL     1       7.391  -1.508   1.300  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.552  -0.846   2.810  1.00  0.00           H  
HETATM   28  H3  UNL     1       7.871   0.093   1.988  1.00  0.00           H  
HETATM   29  H4  UNL     1       4.268   0.144   2.268  1.00  0.00           H  
HETATM   30  H5  UNL     1       3.668   1.979   0.390  1.00  0.00           H  
HETATM   31  H6  UNL     1       2.689   1.125  -2.251  1.00  0.00           H  
HETATM   32  H7  UNL     1      -0.940  -2.039  -1.321  1.00  0.00           H  
HETATM   33  H8  UNL     1      -0.276   0.279   1.642  1.00  0.00           H  
HETATM   34  H9  UNL     1      -0.002   1.622   0.426  1.00  0.00           H  
HETATM   35  H10 UNL     1       0.738  -1.198   0.114  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.172   1.457   1.754  1.00  0.00           H  
HETATM   37  H12 UNL     1      -2.072   2.913  -0.439  1.00  0.00           H  
HETATM   38  H13 UNL     1      -4.065   1.905  -1.149  1.00  0.00           H  
HETATM   39  H14 UNL     1      -5.063   1.799   0.312  1.00  0.00           H  
HETATM   40  H15 UNL     1      -4.685  -0.194  -1.631  1.00  0.00           H  
HETATM   41  H16 UNL     1      -5.490  -0.379  -0.039  1.00  0.00           H  
HETATM   42  H17 UNL     1      -3.874  -1.936  -2.107  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.755  -2.927  -1.041  1.00  0.00           H  
HETATM   44  H19 UNL     1      -4.522  -2.927  -0.769  1.00  0.00           H  
HETATM   45  H20 UNL     1      -4.555  -0.949   1.739  1.00  0.00           H  
HETATM   46  H21 UNL     1      -4.108  -2.619   1.348  1.00  0.00           H  
HETATM   47  H22 UNL     1      -2.832  -1.425   1.933  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3    3   24
CONECT    3    4   29
CONECT    4    5   23   30
CONECT    5    6
CONECT    6    7    7   31
CONECT    7    8   15
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   15   32
CONECT   12   13   13   20
CONECT   13   14   16
CONECT   14   15   33   34
CONECT   15   35
CONECT   16   17   18   36
CONECT   17   37
CONECT   18   19   38   39
CONECT   19   20   40   41
CONECT   20   21   22
CONECT   21   42   43   44
CONECT   22   45   46   47
CONECT   23   24
CONECT   24   25   25
END

HMDB0036677
     RDKit          3D
Strigol
 47 50  0  0  0  0  0  0  0  0999 V2000
    7.0122   -0.6199    1.8486 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9709    0.0369    0.9866 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7368    0.3366    1.2973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0704    0.9712    0.1491 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0119    0.1613   -0.3321 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2569    0.5866   -1.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9416    0.3136   -1.4183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0022    0.6836   -2.4710 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196    1.6620   -3.2840 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0315   -0.2400   -2.4027 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0046   -0.9429   -1.1774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1538   -0.5375   -0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8730    0.5705    0.3188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4117    0.6014    0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1659   -0.3975   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839    1.5450    0.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5171    2.8461    0.4485 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1733    1.3235   -0.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5132   -0.0802   -0.5190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5144   -1.1191   -0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6640   -2.3016   -1.0813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7246   -1.5758    1.3107 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0406    1.0134   -0.8679 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2048    0.4494   -0.3784 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2649    0.3431   -1.0659 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3915   -1.5077    1.3000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5524   -0.8458    2.8099 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8712    0.0931    1.9879 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2681    0.1441    2.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6677    1.9794    0.3899 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6890    1.1251   -2.2506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9395   -2.0391   -1.3214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2762    0.2790    1.6420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0022    1.6220    0.4264 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7385   -1.1982    0.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1725    1.4573    1.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0724    2.9130   -0.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0653    1.9048   -1.1494 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0631    1.7989    0.3117 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6853   -0.1937   -1.6312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4899   -0.3788   -0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8742   -1.9363   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7546   -2.9266   -1.0410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5221   -2.9271   -0.7688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5552   -0.9489    1.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1078   -2.6192    1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8316   -1.4251    1.9325 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
 13 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
  4 23  1  0
 23 24  1  0
 24 25  2  0
 24  2  1  0
 15  7  1  0
 15 11  1  0
 20 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  6 31  1  0
 11 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 18 39  1  0
 19 40  1  0
 19 41  1  0
 21 42  1  0
 21 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 22 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₆

Average Molecular Weight

346.3744

Monoisotopic Molecular Weight

346.141638436

IUPAC Name

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

Traditional Name

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

CAS Registry Number

11017-56-4

SMILES

CC1=CC(O\C=C2/C3CC4=C(C3OC2=O)C(C)(C)CCC4O)OC1=O

InChI Identifier

InChI=1S/C19H22O6/c1-9-6-14(24-17(9)21)23-8-12-10-7-11-13(20)4-5-19(2,3)15(11)16(10)25-18(12)22/h6,8,10,13-14,16,20H,4-5,7H2,1-3H3/b12-8+

InChI Key

VOFXXOPWCBSPAA-XYOKQWHBSA-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
Cyclic alcohol
Dihydrofuran
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Secondary alcohol
Organoheterocyclic compound
Oxacycle
Acetal
Carboxylic acid derivative
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036677)
Cell membrane (HMDB: HMDB0036677)

Cellular substructure

Extracellular (HMDB: HMDB0036677)
Membrane (HMDB: HMDB0036677)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036677)

Source

Endogenous

Endogenous (HMDB: HMDB0036677)

Plant

Poaceae (HMDB: HMDB0036677)

Animal

Animal (HMDB: HMDB0036677)

Exogenous

Food

Food (HMDB: HMDB0036677)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)
Millet (FooDB: FOOD00126)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036677)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036677)

Cellular process

Cell signaling (HMDB: HMDB0036677)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036677)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036677)

Nutrient

Nutrient (HMDB: HMDB0036677)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036677)

Emulsifier (HMDB: HMDB0036677)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	200 - 202 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1030 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	0.15 g/L	ALOGPS
logP	2.7	ALOGPS
logP	2.35	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	14.49	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	82.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	88.87 m³·mol⁻¹	ChemAxon
Polarizability	35.75 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	179.161	31661259
DarkChem	[M-H]-	176.99	31661259
DeepCCS	[M+H]+	183.821	30932474
DeepCCS	[M-H]-	181.463	30932474
DeepCCS	[M-2H]-	214.689	30932474
DeepCCS	[M+Na]+	189.917	30932474
AllCCS	[M+H]+	182.3	32859911
AllCCS	[M+H-H2O]+	179.4	32859911
AllCCS	[M+NH4]+	184.9	32859911
AllCCS	[M+Na]+	185.7	32859911
AllCCS	[M-H]-	184.2	32859911
AllCCS	[M+Na-2H]-	184.1	32859911
AllCCS	[M+HCOO]-	184.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Strigol	CC1=CC(O\C=C2/C3CC4=C(C3OC2=O)C(C)(C)CCC4O)OC1=O	3805.5	Standard polar	33892256
Strigol	CC1=CC(O\C=C2/C3CC4=C(C3OC2=O)C(C)(C)CCC4O)OC1=O	2807.7	Standard non polar	33892256
Strigol	CC1=CC(O\C=C2/C3CC4=C(C3OC2=O)C(C)(C)CCC4O)OC1=O	3045.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Strigol,1TMS,isomer #1	CC1=CC(O/C=C2/C(=O)OC3C4=C(CC23)C(O[Si](C)(C)C)CCC4(C)C)OC1=O	2909.2	Semi standard non polar	33892256
Strigol,1TBDMS,isomer #1	CC1=CC(O/C=C2/C(=O)OC3C4=C(CC23)C(O[Si](C)(C)C(C)(C)C)CCC4(C)C)OC1=O	3137.3	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 - Strigol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00c0-7917000000-c0057daae2e7c874b90a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Strigol GC-MS (1 TMS) - 70eV, Positive	splash10-00fr-9244200000-ea91ba2a278779dc849d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Strigol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Strigol 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 - Strigol 10V, Positive-QTOF	splash10-00u2-1295000000-b27ff052d04808ffb3ff	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Strigol 20V, Positive-QTOF	splash10-00ls-6491000000-1fe6cdcbd2cec7df2160	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Strigol 40V, Positive-QTOF	splash10-02tc-9520000000-1a9e096810e8c5e669ee	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Strigol 10V, Negative-QTOF	splash10-0f6t-2159000000-c4409ae4848631837cb7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Strigol 20V, Negative-QTOF	splash10-0292-9574000000-e66c2ec23770c4486e42	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Strigol 40V, Negative-QTOF	splash10-00nv-9420000000-f78813134b3e762d31c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Strigol 10V, Negative-QTOF	splash10-0002-1019000000-a8d5688541376baeb4eb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Strigol 20V, Negative-QTOF	splash10-0002-0092000000-d25362fce19fc458d453	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Strigol 40V, Negative-QTOF	splash10-0007-4091000000-647c2b505e9199765bd6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Strigol 10V, Positive-QTOF	splash10-005a-0069000000-187c0334896aca653bcb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Strigol 20V, Positive-QTOF	splash10-0f9t-3169000000-58b9ea6da97cef2e9f6f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Strigol 40V, Positive-QTOF	splash10-00g0-1940000000-968ab2b91ea9a8facfe3	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

6391814

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1856381

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 Strigol (HMDB0036677)

MOL for HMDB0036677 (Strigol)

3D MOL for HMDB0036677 (Strigol)

3D SDF for HMDB0036677 (Strigol)

3D-SDF for HMDB0036677 (Strigol)

PDB for HMDB0036677 (Strigol)

3D PDB for HMDB0036677 (Strigol)

SMILES for HMDB0036677 (Strigol)

INCHI for HMDB0036677 (Strigol)

Structure for HMDB0036677 (Strigol)

3D Structure for HMDB0036677 (Strigol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra