NP-MRD: Showing NP-Card for (1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione (NP0196972)

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Record Information

Version

2.0

Created at

2022-09-04 15:09:13 UTC

Updated at

2022-09-04 15:09:13 UTC

NP-MRD ID

NP0196972

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione

Description

(1'S,3R,3'R,4'S,5S,5'S)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]Tridecan]-9'(13')-ene-2,8'-dione belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. (1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione is found in Teucrium betonicum. Based on a literature review very few articles have been published on (1'S,3R,3'R,4'S,5S,5'S)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]Tridecan]-9'(13')-ene-2,8'-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042217092D          

 28 32  0  0  1  0            999 V2000
    2.5332    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9551    0.1456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1563    0.3520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9357    1.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139    1.7355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5782   -0.2365    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3576    0.5585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2206   -0.0300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7988   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5782   -1.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1563   -2.0020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2206   -1.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7988   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5975   -1.2379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8181   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399   -2.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4412   -2.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1757   -0.6494    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8122   -0.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5080   -0.5677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2756   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4820    0.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3055    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6080   -0.1835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9715   -0.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -1.3665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781   -1.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2717   -2.2157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  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
  6 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 14 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END

     RDKit          3D

 52 56  0  0  0  0  0  0  0  0999 V2000
    1.2740    2.1688    0.1617 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2523    1.2607   -0.4965 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0879    1.8267   -0.2814 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2557    3.0633   -1.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405    4.0456   -0.8568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2376    0.9029   -0.5958 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4021    0.9619   -2.0022 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3576    1.4599   -0.0457 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1052    0.7180    0.8066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2355   -0.7038    0.3880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2878   -1.3519    0.3505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9609   -1.3336   -0.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9706   -0.4939   -0.2662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5914   -1.0871   -0.1986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6748   -2.0839    0.9409 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4752   -3.2714    0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8185   -2.8116   -0.0896 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4738   -0.1123    0.0647 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7735   -0.6328   -0.5372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6296   -1.0934    0.5938 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0416   -0.7016    0.3685 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6365   -0.3554   -0.8440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9562   -0.0655   -0.5842 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1737   -0.2186    0.6973 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -0.5972    1.2958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1198   -0.4317    1.7215 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8290   -0.0133    1.5071 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167    0.4054    2.3764 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6828    2.9171   -0.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1474    1.5959    0.5580 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8321    2.6914    1.0369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5193    1.2497   -1.5931 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1706    2.1669    0.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2715    2.7647   -2.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2788    3.4936   -0.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6355    4.5500   -0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2373    1.3850   -2.2626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7954    0.7908    1.8817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1553    1.1316    0.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3996   -1.7026   -1.1238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2571   -1.5987    1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2889   -2.4084    1.3175 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8715   -3.7431   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6452   -3.9699    1.2816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8936   -3.1150   -1.1578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6319   -3.2991    0.4501 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5815   -1.4470   -1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3254    0.1610   -1.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5974   -2.2011    0.6954 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1668   -0.3154   -1.8188 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7044    0.2377   -1.2932 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9673   -0.7894    2.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  3  6  1  0
  6  7  1  6
  6  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 16  1  0
 16 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 26  1  0
 26 27  1  0
 27 28  2  0
 20 21  1  0
 21 25  2  0
 25 24  1  0
 24 23  1  0
 23 22  2  0
 18  2  1  0
 18 27  1  1
 22 21  1  0
 13  6  1  0
 17 12  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  2 32  1  6
  3 33  1  1
  4 34  1  0
  4 35  1  0
  5 36  1  0
  7 37  1  0
  9 38  1  0
  9 39  1  0
 14 40  1  6
 15 41  1  0
 15 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  0
 17 46  1  0
 19 47  1  0
 19 48  1  0
 20 49  1  1
 25 52  1  0
 23 51  1  0
 22 50  1  0
M  END


  Mrv1652309042217092D          

 28 32  0  0  1  0            999 V2000
    2.5332    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9551    0.1456    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1563    0.3520    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9357    1.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5139    1.7355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5782   -0.2365    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3576    0.5585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2206   -0.0300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7988   -0.6186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5782   -1.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1563   -2.0020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2206   -1.6200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7988   -1.0314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5975   -1.2379    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8181   -2.0329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2399   -2.6214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4412   -2.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1757   -0.6494    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8122   -0.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5080   -0.5677    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2756   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4820    0.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3055    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6080   -0.1835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9715   -0.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3016   -1.3665    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4781   -1.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2717   -2.2157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  6  0  0  0
  4  5  1  0  0  0  0
  3  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  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
  6 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 12 17  1  0  0  0  0
 14 18  1  0  0  0  0
  2 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 21 25  2  0  0  0  0
 20 26  1  0  0  0  0
 26 27  1  0  0  0  0
 18 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0196972

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@@H](CO)[C@]2(O)OCC(=O)C3=C2[C@H](CCC3)[C@@]11C[C@H](OC1=O)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H24O7/c1-11-15(8-22)21(25)18-13(16(23)10-27-21)3-2-4-14(18)20(11)7-17(28-19(20)24)12-5-6-26-9-12/h5-6,9,11,14-15,17,22,25H,2-4,7-8,10H2,1H3/t11-,14+,15-,17+,20-,21+/m1/s1

> <INCHI_KEY>
SREQLCNIKCZUGQ-OZSRSVASSA-N

> <FORMULA>
C21H24O7

> <MOLECULAR_WEIGHT>
388.416

> <EXACT_MASS>
388.152203113

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
39.30985539106549

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,3R,3'R,4'S,5S,5'S)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0^{5,13}]tridecan]-9'(13')-ene-2,8'-dione

> <JCHEM_LOGP>
1.6875693596666674

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.385881782140665

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.154946669972142

> <JCHEM_PKA_STRONGEST_BASIC>
-2.676396415157309

> <JCHEM_POLAR_SURFACE_AREA>
106.19999999999999

> <JCHEM_REFRACTIVITY>
96.89609999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,3R,3'R,4'S,5S,5'S)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0^{5,13}]tridecan]-9'(13')-ene-2,8'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0       4.729   1.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.649   0.272   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.158   0.657   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.747   2.141   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       2.826   3.240   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.079  -0.441   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.667   1.042   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -0.412  -0.056   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.491  -1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.079  -2.639   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.158  -3.737   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.412  -3.024   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.491  -1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.982  -2.311   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.394  -3.795   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.315  -4.893   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.824  -4.508   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.061  -1.212   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.249  -0.232   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.548  -1.060   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.981  -0.495   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.366   0.996   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.904   1.090   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.468  -0.343   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.280  -1.322   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.163  -2.551   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.626  -2.645   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       4.240  -4.136   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8   13                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12    6   14                                                  
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   14    2   19   27                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   26                                                  
CONECT   21   20   22   25                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   21                                                       
CONECT   26   20   27                                                       
CONECT   27   26   18   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₂₄O₇

Average Mass

388.4160 Da

Monoisotopic Mass

388.15220 Da

IUPAC Name

(1'S,3R,3'R,4'S,5S,5'S)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0^{5,13}]tridecan]-9'(13')-ene-2,8'-dione

Traditional Name

(1'S,3R,3'R,4'S,5S,5'S)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0^{5,13}]tridecan]-9'(13')-ene-2,8'-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H](CO)[C@]2(O)OCC(=O)C3=C2[C@H](CCC3)[C@@]11C[C@H](OC1=O)C1=COC=C1

InChI Identifier

InChI=1S/C21H24O7/c1-11-15(8-22)21(25)18-13(16(23)10-27-21)3-2-4-14(18)20(11)7-17(28-19(20)24)12-5-6-26-9-12/h5-6,9,11,14-15,17,22,25H,2-4,7-8,10H2,1H3/t11-,14+,15-,17+,20-,21+/m1/s1

InChI Key

SREQLCNIKCZUGQ-OZSRSVASSA-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
Teucrium betonicum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Gamma butyrolactone
Cyclic alcohol
Furan
Tetrahydrofuran
Heteroaromatic compound
Lactone
Ketone
Hemiacetal
Carboxylic acid ester
Monocarboxylic acid or derivatives
Oxacycle
Carboxylic acid derivative
Primary alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	1.69	ChemAxon
pKa (Strongest Acidic)	11.15	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	106.2 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	96.9 m³·mol⁻¹	ChemAxon
Polarizability	39.31 Å³	ChemAxon
Number of Rings	5	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

8538279

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10362830

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione (NP0196972)

MOL for NP0196972 ((1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione)

3D MOL for NP0196972 ((1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione)

3D SDF for NP0196972 ((1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione)

3D-SDF for NP0196972 ((1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione)

PDB for NP0196972 ((1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione)

3D PDB for NP0196972 ((1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione)

SMILES for NP0196972 ((1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione)

INCHI for NP0196972 ((1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione)

Structure for NP0196972 ((1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione)

3D Structure for NP0196972 ((1's,3r,3'r,4's,5s,5's)-5-(furan-3-yl)-5'-hydroxy-4'-(hydroxymethyl)-3'-methyl-6'-oxaspiro[oxolane-3,2'-tricyclo[7.3.1.0⁵,¹³]tridecan]-9'(13')-ene-2,8'-dione)