NP-MRD: Showing NP-Card for 3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid (NP0186667)

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Record Information

Version

2.0

Created at

2022-09-04 02:36:24 UTC

Updated at

2022-09-04 02:36:24 UTC

NP-MRD ID

NP0186667

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid

Description

3,4A-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-5-carboxylic acid belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. 3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid is found in Othonna arborescens. Based on a literature review very few articles have been published on 3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-5-carboxylic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042204362D          

 31 33  0  0  0  0            999 V2000
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 26 30  1  0  0  0  0
 16 30  1  0  0  0  0
  8 30  1  0  0  0  0
 30 31  1  0  0  0  0
M  END

     RDKit          3D

 63 65  0  0  0  0  0  0  0  0999 V2000
   -3.3961   -1.6242   -2.7400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6260   -2.5666   -1.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9522   -2.2255   -0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2196   -3.2638   -0.0816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9565   -0.8057   -0.4200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5894    0.0568   -1.0743 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2651   -0.3871    0.6975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058    0.9411    1.1682 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9517    1.0606    2.4707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2749    1.1988    2.8082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4438    1.2791    1.8845 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2784    1.2496    4.1896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0628    1.1513    4.6598 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2403    1.0362    3.6467 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2453    0.8987    3.7221 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8564    0.6063    2.3983 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3312    0.9009    2.4497 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0204    0.7139    1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9778    0.3773    0.0824 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5843    0.2027   -1.1829 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4492   -0.9808   -1.8942 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7672   -1.8877   -1.3665 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1010   -1.1475   -3.2398 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5825   -0.9765   -3.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8620   -2.5819   -3.7046 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    1.5170    0.0864 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2240    1.5566   -1.1694 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3392    0.7551   -2.1267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7119    2.5799   -1.3369 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1795    1.4653    1.3356 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0570    2.8925    1.8786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759   -0.8867   -3.1920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2322   -1.1315   -2.2154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7998   -2.1772   -3.6120 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6191   -3.6258   -2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3159   -2.8091    0.4189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8030   -4.0525   -0.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8092   -3.6971    0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7679    1.5796    0.4699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9802    2.2612    2.0407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1390    0.4303    2.0030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0443    1.3339    0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1763    1.3571    4.7945 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4983    0.0642    4.4140 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6967    1.8026    4.1744 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6703   -0.4723    2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4633    1.9490    2.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8155    0.2635    3.2290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7890   -0.0990    1.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5097    1.6642    0.8559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4310   -0.5534    0.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6752   -0.4400   -3.9531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0220   -1.9606   -2.8090 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0191   -0.5351   -3.9731 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7430   -0.3011   -2.1632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1918   -3.2397   -2.8679 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7881   -2.7715   -3.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4237   -2.7644   -4.6384 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6294    2.4491    0.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3627    2.6147   -2.0865 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8107    3.1245    2.6317 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1310    3.5758    1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9548    3.0548    2.3021 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 14  2  0
 14 15  1  0
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 17 18  1  0
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 23 24  1  0
 23 25  1  0
 19 26  1  0
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 27 29  1  0
 27 28  2  0
 26 30  1  0
 30 31  1  1
 14 13  1  0
 13 12  1  0
 12 10  2  0
 10 11  1  0
 30  8  1  0
 10  9  1  0
 30 16  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  4 36  1  0
  4 37  1  0
  4 38  1  0
  8 39  1  6
 15 44  1  0
 15 45  1  0
 16 46  1  6
 17 47  1  0
 17 48  1  0
 18 49  1  0
 18 50  1  0
 19 51  1  1
 23 52  1  0
 24 53  1  0
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 24 55  1  0
 25 56  1  0
 25 57  1  0
 25 58  1  0
 26 59  1  1
 29 60  1  0
 31 61  1  0
 31 62  1  0
 31 63  1  0
 12 43  1  0
 11 40  1  0
 11 41  1  0
 11 42  1  0
M  END


  Mrv1652309042204362D          

 31 33  0  0  0  0            999 V2000
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8974    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1274    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6425   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  4  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
  9 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
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 21 23  1  0  0  0  0
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 23 25  1  0  0  0  0
 19 26  1  0  0  0  0
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 27 29  1  0  0  0  0
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 16 30  1  0  0  0  0
  8 30  1  0  0  0  0
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M  END
> <DATABASE_ID>
NP0186667

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC1C2=C(CC3CCC(OC(=O)C(C)C)C(C(O)=O)C13C)OC=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O7/c1-7-13(4)23(28)31-20-18-14(5)11-29-17(18)10-15-8-9-16(30-22(27)12(2)3)19(21(25)26)24(15,20)6/h7,11-12,15-16,19-20H,8-10H2,1-6H3,(H,25,26)

> <INCHI_KEY>
FQWWVFXVGRJJTK-UHFFFAOYSA-N

> <FORMULA>
C24H32O7

> <MOLECULAR_WEIGHT>
432.513

> <EXACT_MASS>
432.21480337

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
45.950899090035115

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-5-carboxylic acid

> <JCHEM_LOGP>
4.957371945

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.702663102570708

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7268457872743435

> <JCHEM_POLAR_SURFACE_AREA>
103.04

> <JCHEM_REFRACTIVITY>
113.39799999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-5-carboxylic acid

> <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       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.799   2.016   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.275   3.481   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.705   0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.799  -0.476   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   30                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   30                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   19   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   26   16    8   31                                             
CONECT   31   30                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
3,4a-Dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-5-carboxylate	Generator

Chemical Formula

C₂₄H₃₂O₇

Average Mass

432.5130 Da

Monoisotopic Mass

432.21480 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC1C2=C(CC3CCC(OC(=O)C(C)C)C(C(O)=O)C13C)OC=C2C

InChI Identifier

InChI=1S/C24H32O7/c1-7-13(4)23(28)31-20-18-14(5)11-29-17(18)10-15-8-9-16(30-22(27)12(2)3)19(21(25)26)24(15,20)6/h7,11-12,15-16,19-20H,8-10H2,1-6H3,(H,25,26)

InChI Key

FQWWVFXVGRJJTK-UHFFFAOYSA-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
Othonna arborescens	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Furoeremophilane sesquiterpenoid
Naphthofuran
Benzofuran
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Heteroaromatic compound
Furan
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Carboxylic acid
Carboxylic acid derivative
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

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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162985633

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid (NP0186667)

MOL for NP0186667 (3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid)

3D MOL for NP0186667 (3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid)

3D SDF for NP0186667 (3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid)

3D-SDF for NP0186667 (3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid)

PDB for NP0186667 (3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid)

3D PDB for NP0186667 (3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid)

SMILES for NP0186667 (3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid)

INCHI for NP0186667 (3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid)

Structure for NP0186667 (3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid)

3D Structure for NP0186667 (3,4a-dimethyl-4-[(2-methylbut-2-enoyl)oxy]-6-[(2-methylpropanoyl)oxy]-4h,5h,6h,7h,8h,8ah,9h-naphtho[2,3-b]furan-5-carboxylic acid)