NP-MRD: Showing NP-Card for (1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione (NP0213840)

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Record Information

Version

2.0

Created at

2022-09-05 12:56:49 UTC

Updated at

2022-09-05 12:56:49 UTC

NP-MRD ID

NP0213840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione

Description

BACCHOTRICUNEATIN A belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione is found in Baccharis incarum, Baccharis neaei, Baccharis polifolia, Baccharis salicifolia, Baccharis spicata, Laennecia coulteri and Liatris spicata. (1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione was first documented in 2005 (PMID: 16402545). Based on a literature review a small amount of articles have been published on BACCHOTRICUNEATIN A (PMID: 23906773) (PMID: 20422996).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052214562D          

 25 29  0  0  1  0            999 V2000
    2.0906    0.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283   -0.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8232    0.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.2533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2506    0.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2994    1.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0977    1.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5423    0.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -0.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933   -1.0774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360   -2.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659   -1.1426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4709   -1.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107   -1.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.3836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5662   -1.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495   -1.3211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4330   -0.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -0.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0693    0.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    1.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581    0.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957    0.0611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  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  0  0  0  0
  5  9  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  6  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 16 25  1  0  0  0  0
  2 25  1  0  0  0  0
M  END

     RDKit          3D

 47 51  0  0  0  0  0  0  0  0999 V2000
    0.4895    1.5780    0.0521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2370    0.1302   -0.1582 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3471   -0.6576    0.5017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6081   -0.7151   -0.2693 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.8242   -0.3521    0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0674   -0.1756   -0.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9349    0.1485    0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2611    0.1628    2.0388 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0046   -0.1281    1.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6160    0.0844   -1.4341 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741    0.2777   -2.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5747    0.8537   -3.2968 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2214   -0.2212   -1.6563 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9692    0.2985   -2.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2972   -0.0874   -1.7588 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2552    0.2490   -0.2709 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4512    1.7338   -0.1708 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7971    1.8256   -0.7131 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4914    0.6927   -0.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7097    0.4240   -0.3878 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4998   -0.1750    0.4221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5606   -1.0392    1.3935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3209   -1.7161    1.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1912   -0.6516    1.8037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0892   -0.3822    0.3493 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1556    2.0662    0.8047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357    1.7370    0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5284    2.1568   -0.9191 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5469   -0.1409    1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9595   -1.6774    0.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7700   -1.7737   -0.6108 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3119   -0.2709   -1.1352 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9883    0.3520    0.7980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2052   -0.1919    2.5917 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1925   -1.3365   -1.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332    1.4004   -2.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9589   -0.1490   -3.3909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0893    0.5420   -2.2034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5386   -1.1503   -1.8933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5464    2.1192    0.8469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8531    2.3333   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4994   -1.2955    1.8360 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5100   -1.8761    3.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0858   -2.6261    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4886    0.1947    2.4263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3144   -1.1204    2.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0925   -1.4507   -0.1038 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6
  2  3  1  0
  3  4  1  0
  4 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 16 15  1  6
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  4  5  1  0
  5  9  2  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
 13  2  1  0
 21 16  1  0
  6  5  1  0
 25  2  1  0
 25 16  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  6
 13 35  1  1
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 17 40  1  0
 17 41  1  0
 22 42  1  0
 23 43  1  0
 23 44  1  0
 24 45  1  0
 24 46  1  0
 25 47  1  6
  9 34  1  0
  7 33  1  0
  6 32  1  0
M  END


  Mrv1652309052214562D          

 25 29  0  0  1  0            999 V2000
    2.0906    0.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1283   -0.3184    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8232    0.1262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5557   -0.2533    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2506    0.1913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2994    1.0149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0977    1.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5423    0.5281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0188   -0.1095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5933   -1.0774    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8984   -1.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360   -2.3462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1659   -1.1426    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4709   -1.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9107   -1.3650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7008   -0.3836    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5662   -1.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495   -1.3211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6190   -0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4330   -0.4489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0317   -0.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0693    0.8201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6256    1.2647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3581    0.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3957    0.0611    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  6  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  0  0  0  0
  5  9  2  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 11  1  6  0  0  0
  2 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 25 24  1  6  0  0  0
 16 25  1  0  0  0  0
  2 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@]12C[C@@H](OC(=O)[C@@H]1CC[C@@]13COC(=O)C1=CCC[C@H]23)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O5/c1-19-9-15(12-6-8-23-10-12)25-18(22)13(19)5-7-20-11-24-17(21)14(20)3-2-4-16(19)20/h3,6,8,10,13,15-16H,2,4-5,7,9,11H2,1H3/t13-,15+,16+,19-,20+/m0/s1

> <INCHI_KEY>
BLXXJMVVAYFKDR-FQCQXKDLSA-N

> <FORMULA>
C20H22O5

> <MOLECULAR_WEIGHT>
342.391

> <EXACT_MASS>
342.146723808

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
47

> <JCHEM_AVERAGE_POLARIZABILITY>
35.442761778875635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,7R,9R,10R)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0^{1,14}.0^{4,9}]heptadec-13-ene-5,15-dione

> <JCHEM_LOGP>
3.0637318556666675

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8885633957130588

> <JCHEM_POLAR_SURFACE_AREA>
65.74000000000001

> <JCHEM_REFRACTIVITY>
89.0737

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,7R,9R,10R)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0^{1,14}.0^{4,9}]heptadec-13-ene-5,15-dione

> <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       3.903   0.944   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.973  -0.594   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.270   0.236   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.637  -0.473   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.935   0.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.026   1.894   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.516   2.283   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.346   0.986   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.368  -0.204   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.708  -2.011   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.410  -2.841   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.481  -4.380   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.043  -2.133   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.746  -2.963   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.700  -2.548   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.308  -0.716   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.057  -2.235   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.466  -2.466   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.156  -1.089   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.675  -0.838   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -0.059  -0.008   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.129   1.531   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.168   2.361   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.535   1.652   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.605   0.114   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   13   25                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5                                                       
CONECT   10    4   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    2   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21   25                                             
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   16   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   16    2                                                  
MASTER        0    0    0    0    0    0    0    0   25    0   58    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₂O₅

Average Mass

342.3910 Da

Monoisotopic Mass

342.14672 Da

IUPAC Name

(1S,4R,7R,9R,10R)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0^{1,14}.0^{4,9}]heptadec-13-ene-5,15-dione

Traditional Name

(1S,4R,7R,9R,10R)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0^{1,14}.0^{4,9}]heptadec-13-ene-5,15-dione

CAS Registry Number

Not Available

SMILES

C[C@]12C[C@@H](OC(=O)[C@@H]1CC[C@@]13COC(=O)C1=CCC[C@H]23)C1=COC=C1

InChI Identifier

InChI=1S/C20H22O5/c1-19-9-15(12-6-8-23-10-12)25-18(22)13(19)5-7-20-11-24-17(21)14(20)3-2-4-16(19)20/h3,6,8,10,13,15-16H,2,4-5,7,9,11H2,1H3/t13-,15+,16+,19-,20+/m0/s1

InChI Key

BLXXJMVVAYFKDR-FQCQXKDLSA-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
Baccharis incarum	LOTUS Database	35616633
Baccharis neaei	LOTUS Database	35616633
Baccharis polifolia	LOTUS Database	35616633
Baccharis salicifolia	LOTUS Database	35616633
Baccharis spicata	LOTUS Database	35616633
Laennecia coulteri	LOTUS Database	35616633
Liatris spicata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
Naphthalene
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxane
Pyran
Oxolane
Heteroaromatic compound
Furan
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
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	3.06	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.74 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.07 m³·mol⁻¹	ChemAxon
Polarizability	35.44 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

C00036406

Chemspider ID

20057730

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14021509

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Rodriguez MV, Sortino MA, Ivancovich JJ, Pellegrino JM, Favier LS, Raimondi MP, Gattuso MA, Zacchino SA: Detection of synergistic combinations of Baccharis extracts with terbinafine against Trichophyton rubrum with high throughput screening synergy assay (HTSS) followed by 3D graphs. Behavior of some of their components. Phytomedicine. 2013 Oct 15;20(13):1230-9. doi: 10.1016/j.phymed.2013.06.015. Epub 2013 Jul 30. [PubMed:23906773 ]
Fan X, Lin S, Zhu C, Hu J, Liu Y, Chen X, Chen N, Wang W, Shi J: [Terpenoids of Heteroplexis micocephala and their bioactivities]. Zhongguo Zhong Yao Za Zhi. 2010 Feb;35(3):315-22. doi: 10.4268/cjcmm20100313. [PubMed:20422996 ]
Gonzalez-Coloma A, Guadano A, Tonn CE, Sosa ME: Antifeedant/insecticidal terpenes from asteraceae and labiatae species native to Argentinean semi-arid lands. Z Naturforsch C J Biosci. 2005 Nov-Dec;60(11-12):855-61. doi: 10.1515/znc-2005-11-1207. [PubMed:16402545 ]
LOTUS database [Link]

Showing NP-Card for (1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione (NP0213840)

MOL for NP0213840 ((1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione)

3D MOL for NP0213840 ((1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione)

3D SDF for NP0213840 ((1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione)

3D-SDF for NP0213840 ((1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione)

PDB for NP0213840 ((1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione)

3D PDB for NP0213840 ((1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione)

SMILES for NP0213840 ((1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione)

INCHI for NP0213840 ((1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione)

Structure for NP0213840 ((1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione)

3D Structure for NP0213840 ((1s,4r,7r,9r,10r)-7-(furan-3-yl)-9-methyl-6,16-dioxatetracyclo[8.7.0.0¹,¹⁴.0⁴,⁹]heptadec-13-ene-5,15-dione)