NP-MRD: Showing NP-Card for Strigol (NP0048569)

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Record Information

Version

2.0

Created at

2022-03-17 20:58:31 UTC

Updated at

2022-03-17 20:58:31 UTC

NP-MRD ID

NP0048569

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Strigol

Description

Strigol 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. Strigol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Strigol has been detected, but not quantified in, a few different foods, such as corns, fats and oils, and millets. Strigol is found in Gossypium hirsutum , Houttuynia cordata , Menispermum dauricum , Sorghum bicolor and Trifolium pratense. This could make strigol a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  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>
NP0048569

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₉H₂₂O₆

Average Mass

346.3744 Da

Monoisotopic Mass

346.14164 Da

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

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Gossypium hirsutum	Plant	KNApSAcK
Houttuynia cordata	Plant	KNApSAcK
Menispermum dauricum	Plant	KNApSAcK
Panicum miliaceum	FooDB	KNAPSACK
Sorghum bicolor	LOTUS Database	35616633
Trifolium pratense	LOTUS Database	35616633
Zea mays L.	FooDB	KNAPSACK

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

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0036677

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB015607

KNApSAcK ID

C00003486

Chemspider ID

Not Available

KEGG Compound ID

C09190

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

Good Scents ID

Not Available

References

General References

Showing NP-Card for Strigol (NP0048569)

MOL for NP0048569 (Strigol)

3D MOL for NP0048569 (Strigol)

3D SDF for NP0048569 (Strigol)

3D-SDF for NP0048569 (Strigol)

PDB for NP0048569 (Strigol)

3D PDB for NP0048569 (Strigol)

SMILES for NP0048569 (Strigol)

INCHI for NP0048569 (Strigol)

Structure for NP0048569 (Strigol)

3D Structure for NP0048569 (Strigol)