NP-MRD: Showing NP-Card for (3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate (NP0208116)

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Record Information

Version

2.0

Created at

2022-09-05 04:59:36 UTC

Updated at

2022-09-05 04:59:36 UTC

NP-MRD ID

NP0208116

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate

Description

(+)-Orobanchyl acetate, also known as 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. (3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate is found in Linum usitatissimum and Pisum sativum. (3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate was first documented in 2014 (PMID: 24974726). Based on a literature review a small amount of articles have been published on (+)-Orobanchyl acetate (PMID: 30280444) (PMID: 28851101) (PMID: 34961023) (PMID: 26252191).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052206592D          

 28 31  0  0  1  0            999 V2000
    0.7687   -4.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7849   -3.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5074   -3.0866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787   -3.0584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0950   -2.2336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7719   -1.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5324   -0.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2924   -0.9561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9502   -0.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270   -0.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4065   -0.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3876   -1.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856   -2.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650   -3.1372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629   -3.7950    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8235   -4.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -5.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5166   -5.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1581   -4.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9476   -4.7976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8878   -3.7787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5628   -1.7356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0964   -0.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4056    0.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205    0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8999   -0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1393   -1.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5753   -1.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 15 21  1  0  0  0  0
 22 12  1  6  0  0  0
  5 22  1  0  0  0  0
  8 22  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  6 28  1  0  0  0  0
M  END

     RDKit          3D

 52 55  0  0  0  0  0  0  0  0999 V2000
    0.1988    3.0952    3.2113 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2680    2.6911    1.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5227    3.6041    1.0374 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4332    1.3564    1.4869 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8775    1.0913    0.1960 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1813    0.3519    0.1627 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1856   -0.5266   -0.8343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9599   -0.3199   -1.6502 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0922    0.7742   -2.5344 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0591    1.5508   -2.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3697    2.5142   -3.2900 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9111    1.0464   -1.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1859    1.2737   -1.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8714    0.7270   -0.1546 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2903    0.7219   -0.2331 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9086    0.1378    0.9691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7059   -0.8408    0.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5237   -1.6885    1.5362 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6557   -0.9509   -0.8568 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3113   -1.8003   -1.5522 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7853    0.0168   -1.3040 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0126    0.2119   -0.6106 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3188   -1.4742   -0.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4193   -0.8065   -1.7747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8976   -2.7049   -1.7240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8467   -1.9232    0.3789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9816   -0.8481    1.3994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3716    0.4580    1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580    4.0909    3.1702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6932    3.0610    3.8862 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9094    2.3315    3.5836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0526    2.0282   -0.3985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5983   -1.2372   -2.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6836    1.9236   -1.9678 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6718    1.7753   -0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7632    0.4306    2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9620   -1.7460    2.4795 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7835   -2.6547    1.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4915   -1.1693    1.7629 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5203   -0.5755   -0.0549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9438   -0.0633   -2.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9104   -1.5634   -2.4356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2235   -0.4012   -1.1307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390   -3.3657   -1.1384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4726   -2.4402   -2.7172 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8310   -3.3019   -1.9301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2044   -2.7523    0.7869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8450   -2.4070    0.1933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0750   -0.6575    1.6002 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5635   -1.1851    2.3807 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1169    0.9922    1.9814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1072    1.1487    0.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5 22  1  0
 22  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 21  1  0
 21 19  1  0
 19 20  2  0
 19 17  1  0
 17 18  1  0
 17 16  2  0
  8  7  1  0
  7  6  2  0
  6 28  1  0
 28 27  1  0
 27 26  1  0
 26 23  1  0
 23 24  1  0
 23 25  1  0
  6  5  1  0
 12 22  1  0
 16 15  1  0
 23  7  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  5 32  1  6
 22 40  1  1
  8 33  1  6
 13 34  1  0
 15 35  1  6
 18 37  1  0
 18 38  1  0
 18 39  1  0
 16 36  1  0
 28 51  1  0
 28 52  1  0
 27 49  1  0
 27 50  1  0
 26 47  1  0
 26 48  1  0
 24 41  1  0
 24 42  1  0
 24 43  1  0
 25 44  1  0
 25 45  1  0
 25 46  1  0
M  END


  Mrv1652309052206592D          

 28 31  0  0  1  0            999 V2000
    0.7687   -4.3097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7849   -3.4849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5074   -3.0866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0787   -3.0584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0950   -2.2336    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7719   -1.7619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5324   -0.9724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2924   -0.9561    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9502   -0.4581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6270   -0.9298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4065   -0.6595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3876   -1.7193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8856   -2.3771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5650   -3.1372    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0629   -3.7950    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8235   -4.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -5.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5166   -5.8810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1581   -4.5581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9476   -4.7976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8878   -3.7787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5628   -1.7356    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0964   -0.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4056    0.0806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4205    0.3884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8999   -0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1393   -1.3472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5753   -1.9493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 15 14  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 15 21  1  0  0  0  0
 22 12  1  6  0  0  0
  5 22  1  0  0  0  0
  8 22  1  0  0  0  0
  7 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
  6 28  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0208116

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@H]1[C@H]2[C@H](OC(=O)\C2=C\O[C@@H]2OC(=O)C(C)=C2)C2=C1CCCC2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O7/c1-10-8-14(27-19(10)23)25-9-13-15-17(26-11(2)22)12-6-5-7-21(3,4)16(12)18(15)28-20(13)24/h8-9,14-15,17-18H,5-7H2,1-4H3/b13-9+/t14-,15+,17-,18+/m1/s1

> <INCHI_KEY>
DLRIUVHQJRZTMZ-CQMYTRALSA-N

> <FORMULA>
C21H24O7

> <MOLECULAR_WEIGHT>
388.416

> <EXACT_MASS>
388.152203113

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
38.644659033180545

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,3aS,4S,8bS)-8,8-dimethyl-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylidene)-2-oxo-2H,3H,3aH,4H,5H,6H,7H,8H,8bH-indeno[1,2-b]furan-4-yl acetate

> <JCHEM_LOGP>
2.828527815666665

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.0347968421381

> <JCHEM_PKA_STRONGEST_BASIC>
-4.937810266327797

> <JCHEM_POLAR_SURFACE_AREA>
88.13000000000001

> <JCHEM_REFRACTIVITY>
97.9185

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E,3aS,4S,8bS)-8,8-dimethyl-3-({[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxy}methylidene)-2-oxo-3aH,4H,5H,6H,7H,8bH-indeno[1,2-b]furan-4-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.435  -8.045   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.465  -6.505   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.814  -5.762   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.147  -5.709   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.177  -4.169   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.441  -3.289   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.994  -1.815   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.546  -1.785   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.774  -0.855   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.037  -1.736   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.492  -1.231   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.590  -3.209   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.520  -4.437   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.921  -5.856   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.851  -7.084   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.404  -8.558   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.667  -9.438   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.698 -10.978   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.895  -8.509   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -7.369  -8.955   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.391  -7.054   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -1.050  -3.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.047  -0.691   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.757   0.150   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.652   0.725   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.546  -1.041   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.993  -2.515   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.941  -3.639   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   22                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8   23                                                  
CONECT    8    7    9   22                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   22                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   21                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   15                                                       
CONECT   22   12    5    8                                                  
CONECT   23    7   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27    6                                                       
MASTER        0    0    0    0    0    0    0    0   28    0   62    0
END

View in JSmol

Synonyms

Value	Source
(+)-Orobanchyl acetic acid	Generator
(+)-Strigol	MeSH
Strigol	MeSH

Chemical Formula

C₂₁H₂₄O₇

Average Mass

388.4160 Da

Monoisotopic Mass

388.15220 Da

IUPAC Name

(3E,3aS,4S,8bS)-8,8-dimethyl-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylidene)-2-oxo-2H,3H,3aH,4H,5H,6H,7H,8H,8bH-indeno[1,2-b]furan-4-yl acetate

Traditional Name

(3E,3aS,4S,8bS)-8,8-dimethyl-3-({[(2R)-4-methyl-5-oxo-2H-furan-2-yl]oxy}methylidene)-2-oxo-3aH,4H,5H,6H,7H,8bH-indeno[1,2-b]furan-4-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@H]1[C@H]2[C@H](OC(=O)\C2=C\O[C@@H]2OC(=O)C(C)=C2)C2=C1CCCC2(C)C

InChI Identifier

InChI=1S/C21H24O7/c1-10-8-14(27-19(10)23)25-9-13-15-17(26-11(2)22)12-6-5-7-21(3,4)16(12)18(15)28-20(13)24/h8-9,14-15,17-18H,5-7H2,1-4H3/b13-9+/t14-,15+,17-,18+/m1/s1

InChI Key

DLRIUVHQJRZTMZ-CQMYTRALSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Linum usitatissimum	LOTUS Database	35616633
Pisum sativum	LOTUS Database	35616633

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
Tricarboxylic acid or derivatives
2-furanone
Gamma butyrolactone
Dihydrofuran
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Vinylogous ester
Lactone
Carboxylic acid ester
Acetal
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
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	2.83	ChemAxon
pKa (Strongest Acidic)	13.03	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	97.92 m³·mol⁻¹	ChemAxon
Polarizability	38.64 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

58837439

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24796587

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rial C, Varela RM, Molinillo JMG, Lopez-Raez JA, Macias FA: A new UHPLC-MS/MS method for the direct determination of strigolactones in root exudates and extracts. Phytochem Anal. 2019 Jan;30(1):110-116. doi: 10.1002/pca.2796. Epub 2018 Oct 2. [PubMed:30280444 ]
Boutet-Mercey S, Perreau F, Roux A, Clave G, Pillot JP, Schmitz-Afonso I, Touboul D, Mouille G, Rameau C, Boyer FD: Validated Method for Strigolactone Quantification by Ultra High-Performance Liquid Chromatography - Electrospray Ionisation Tandem Mass Spectrometry Using Novel Deuterium Labelled Standards. Phytochem Anal. 2018 Jan;29(1):59-68. doi: 10.1002/pca.2714. Epub 2017 Aug 29. [PubMed:28851101 ]
Galili S, Hershenhorn J, Smirnov E, Yoneyama K, Xie X, Amir-Segev O, Bellalou A, Dor E: Characterization of a Chickpea Mutant Resistant to Phelipanche aegyptiaca Pers. and Orobanche crenata Forsk. Plants (Basel). 2021 Nov 23;10(12). pii: plants10122552. doi: 10.3390/plants10122552. [PubMed:34961023 ]
Bharti N, Tripathi S, Bhatla SC: Photomodulation of strigolactone biosynthesis and accumulation during sunflower seedling growth. Plant Signal Behav. 2015;10(8):e1049792. doi: 10.1080/15592324.2015.1049792. [PubMed:26252191 ]
Fernandez-Aparicio M, Kisugi T, Xie X, Rubiales D, Yoneyama K: Low strigolactone root exudation: a novel mechanism of broomrape (Orobanche and Phelipanche spp.) resistance available for faba bean breeding. J Agric Food Chem. 2014 Jul 23;62(29):7063-71. doi: 10.1021/jf5027235. Epub 2014 Jul 9. [PubMed:24974726 ]
LOTUS database [Link]

Showing NP-Card for (3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate (NP0208116)

MOL for NP0208116 ((3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate)

3D MOL for NP0208116 ((3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate)

3D SDF for NP0208116 ((3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate)

3D-SDF for NP0208116 ((3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate)

PDB for NP0208116 ((3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate)

3D PDB for NP0208116 ((3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate)

SMILES for NP0208116 ((3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate)

INCHI for NP0208116 ((3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate)

Structure for NP0208116 ((3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate)

3D Structure for NP0208116 ((3e,3as,4s,8bs)-8,8-dimethyl-3-({[(2r)-4-methyl-5-oxo-2h-furan-2-yl]oxy}methylidene)-2-oxo-3ah,4h,5h,6h,7h,8bh-indeno[1,2-b]furan-4-yl acetate)