NP-MRD: Showing NP-Card for 6beta-angeloyloxyfuranoeremophilan-15-oic acid (NP0025330)

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Record Information

Version

2.0

Created at

2021-06-19 17:28:49 UTC

Updated at

2021-06-29 23:50:13 UTC

NP-MRD ID

NP0025330

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6beta-angeloyloxyfuranoeremophilan-15-oic acid

Provided By

JEOL Database JEOL Logo

Description

(4S,4aS,5S,8aR)-3,4a-dimethyl-4-{[(2E)-2-methylbut-2-enoyl]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. 6beta-angeloyloxyfuranoeremophilan-15-oic acid is found in Ligularia vellerea. 6beta-angeloyloxyfuranoeremophilan-15-oic acid was first documented in 2008 (Tori, M., et al.). Based on a literature review very few articles have been published on (4S,4aS,5S,8aR)-3,4a-dimethyl-4-{[(2E)-2-methylbut-2-enoyl]oxy}-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-5-carboxylic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119283D          

 51 53  0  0  0  0            999 V2000
   -2.9785   -1.4693   -4.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9536   -1.1283   -3.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016    0.0947   -2.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600    1.3978   -3.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506    0.2632   -1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    1.3447   -1.3607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -0.9120   -1.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8575   -0.8964   -0.0088 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9103   -1.9221   -0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5829   -2.2600   -1.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858   -1.6675   -2.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4692   -3.2658   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972   -3.5560    0.1387 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4585   -2.7306    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251   -2.7979    2.0869 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2905   -1.5498    2.4860 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2206   -0.3602    2.7973 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4460    0.8635    3.2689 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3575    1.2803    2.2855 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5697    0.1273    1.8706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5644   -0.1259    2.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -0.5238    4.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8339    0.1365    2.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1911   -1.1651    1.4153 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8294   -2.3318    1.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522   -2.1810   -4.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374   -0.6100   -4.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407   -1.9444   -3.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499   -2.0097   -2.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7886    1.2903   -3.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1362    1.8822   -3.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039    2.0738   -2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    0.0641    0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846   -0.5743   -2.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321   -1.9954   -3.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1843   -1.9671   -3.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1900   -3.8455   -1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0326   -2.8735    2.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5371   -3.7048    2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7896   -1.8098    3.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -0.6461    3.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -0.0926    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403    1.6992    3.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0033    0.6573    4.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284    2.0944    2.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8336    1.7057    1.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1687    0.4909    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -0.0599    3.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1810   -2.6735    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3983   -3.2028    0.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7090   -2.0265    0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  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
 18 19  1  0  0  0  0
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 21 23  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  2  0  0  0  0
 16 40  1  1  0  0  0
  7  5  1  0  0  0  0
 15 14  1  0  0  0  0
  5  6  2  0  0  0  0
 14  9  2  0  0  0  0
  5  3  1  0  0  0  0
  3  4  1  0  0  0  0
 16 24  1  0  0  0  0
  3  2  2  0  0  0  0
 16 15  1  0  0  0  0
  2  1  1  0  0  0  0
 24  8  1  0  0  0  0
 10 11  1  0  0  0  0
 15 38  1  0  0  0  0
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  8 33  1  1  0  0  0
 18 43  1  0  0  0  0
 18 44  1  0  0  0  0
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 19 46  1  0  0  0  0
 20 47  1  6  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 12 37  1  0  0  0  0
 25 49  1  0  0  0  0
 25 50  1  0  0  0  0
 25 51  1  0  0  0  0
 23 48  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  2 29  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -2.9785   -1.4693   -4.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9536   -1.1283   -3.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016    0.0947   -2.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600    1.3978   -3.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506    0.2632   -1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    1.3447   -1.3607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -0.9120   -1.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8575   -0.8964   -0.0088 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9103   -1.9221   -0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5829   -2.2600   -1.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858   -1.6675   -2.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4692   -3.2658   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972   -3.5560    0.1387 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4585   -2.7306    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251   -2.7979    2.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905   -1.5498    2.4860 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2206   -0.3602    2.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    0.8635    3.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    1.2803    2.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697    0.1273    1.8706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5644   -0.1259    2.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -0.5238    4.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8339    0.1365    2.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1911   -1.1651    1.4153 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8294   -2.3318    1.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522   -2.1810   -4.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374   -0.6100   -4.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407   -1.9444   -3.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499   -2.0097   -2.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7886    1.2903   -3.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1362    1.8822   -3.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039    2.0738   -2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    0.0641    0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846   -0.5743   -2.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0326   -2.8735    2.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5371   -3.7048    2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7896   -1.8098    3.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -0.6461    3.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -0.0926    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403    1.6992    3.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0033    0.6573    4.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284    2.0944    2.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1687    0.4909    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -0.0599    3.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7090   -2.0265    0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  9 10  1  0
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 13 14  1  0
 18 19  1  0
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  8  7  1  0
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M  END


  Mrv1652306192119283D          

 51 53  0  0  0  0            999 V2000
   -2.9785   -1.4693   -4.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9536   -1.1283   -3.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016    0.0947   -2.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600    1.3978   -3.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506    0.2632   -1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    1.3447   -1.3607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -0.9120   -1.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8575   -0.8964   -0.0088 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9103   -1.9221   -0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5829   -2.2600   -1.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858   -1.6675   -2.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4692   -3.2658   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972   -3.5560    0.1387 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4585   -2.7306    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251   -2.7979    2.0869 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2905   -1.5498    2.4860 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2206   -0.3602    2.7973 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4460    0.8635    3.2689 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3575    1.2803    2.2855 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5697    0.1273    1.8706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5644   -0.1259    2.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -0.5238    4.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8339    0.1365    2.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.8294   -2.3318    1.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.1362    1.8822   -3.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039    2.0738   -2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    0.0641    0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846   -0.5743   -2.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321   -1.9954   -3.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1843   -1.9671   -3.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1900   -3.8455   -1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0326   -2.8735    2.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5371   -3.7048    2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7896   -1.8098    3.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -0.6461    3.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -0.0926    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403    1.6992    3.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0033    0.6573    4.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284    2.0944    2.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8336    1.7057    1.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1687    0.4909    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -0.0599    3.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1810   -2.6735    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3983   -3.2028    0.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7090   -2.0265    0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0  0  0  0
  9 10  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
 18 19  1  0  0  0  0
 24 25  1  6  0  0  0
 18 17  1  0  0  0  0
  8  7  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 24  1  0  0  0  0
 21 23  1  0  0  0  0
 16 17  1  0  0  0  0
 21 22  2  0  0  0  0
 16 40  1  1  0  0  0
  7  5  1  0  0  0  0
 15 14  1  0  0  0  0
  5  6  2  0  0  0  0
 14  9  2  0  0  0  0
  5  3  1  0  0  0  0
  3  4  1  0  0  0  0
 16 24  1  0  0  0  0
  3  2  2  0  0  0  0
 16 15  1  0  0  0  0
  2  1  1  0  0  0  0
 24  8  1  0  0  0  0
 10 11  1  0  0  0  0
 15 38  1  0  0  0  0
 15 39  1  0  0  0  0
  8 33  1  1  0  0  0
 18 43  1  0  0  0  0
 18 44  1  0  0  0  0
 19 45  1  0  0  0  0
 19 46  1  0  0  0  0
 20 47  1  6  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 12 37  1  0  0  0  0
 25 49  1  0  0  0  0
 25 50  1  0  0  0  0
 25 51  1  0  0  0  0
 23 48  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  4 32  1  0  0  0  0
  2 29  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
 11 34  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025330

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)[C@@]1([H])C([H])([H])C([H])([H])C([H])([H])[C@]2([H])C([H])([H])C3=C(C(=C([H])O3)C([H])([H])[H])[C@@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])[C@]12C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H26O5/c1-5-11(2)19(23)25-17-16-12(3)10-24-15(16)9-13-7-6-8-14(18(21)22)20(13,17)4/h5,10,13-14,17H,6-9H2,1-4H3,(H,21,22)/b11-5+/t13-,14-,17-,20+/m1/s1

> <INCHI_KEY>
YOHUCVRCSMMGNP-QZQBWGCWSA-N

> <FORMULA>
C20H26O5

> <MOLECULAR_WEIGHT>
346.423

> <EXACT_MASS>
346.178023937

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
37.48856529251509

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.19

> <JCHEM_LOGP>
4.503535476333334

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.756178625919551

> <JCHEM_PKA_STRONGEST_BASIC>
-2.726862986676561

> <JCHEM_POLAR_SURFACE_AREA>
76.74

> <JCHEM_REFRACTIVITY>
93.5296

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
   -2.9785   -1.4693   -4.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9536   -1.1283   -3.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016    0.0947   -2.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600    1.3978   -3.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506    0.2632   -1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    1.3447   -1.3607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -0.9120   -1.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8575   -0.8964   -0.0088 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9103   -1.9221   -0.3180 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5829   -2.2600   -1.5293 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3858   -1.6675   -2.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4692   -3.2658   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3972   -3.5560    0.1387 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4585   -2.7306    0.6502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1251   -2.7979    2.0869 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2905   -1.5498    2.4860 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2206   -0.3602    2.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    0.8635    3.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    1.2803    2.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697    0.1273    1.8706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5644   -0.1259    2.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -0.5238    4.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8339    0.1365    2.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1911   -1.1651    1.4153 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8294   -2.3318    1.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522   -2.1810   -4.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374   -0.6100   -4.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407   -1.9444   -3.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499   -2.0097   -2.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7886    1.2903   -3.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1362    1.8822   -3.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039    2.0738   -2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    0.0641    0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846   -0.5743   -2.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321   -1.9954   -3.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1843   -1.9671   -3.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1900   -3.8455   -1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0326   -2.8735    2.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5371   -3.7048    2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7896   -1.8098    3.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -0.6461    3.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -0.0926    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403    1.6992    3.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0033    0.6573    4.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284    2.0944    2.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8336    1.7057    1.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1687    0.4909    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -0.0599    3.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1810   -2.6735    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3983   -3.2028    0.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7090   -2.0265    0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  9 10  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 18 19  1  0
 24 25  1  6
 18 17  1  0
  8  7  1  0
 19 20  1  0
 20 21  1  0
 20 24  1  0
 21 23  1  0
 16 17  1  0
 21 22  2  0
 16 40  1  1
  7  5  1  0
 15 14  1  0
  5  6  2  0
 14  9  2  0
  5  3  1  0
  3  4  1  0
 16 24  1  0
  3  2  2  0
 16 15  1  0
  2  1  1  0
 24  8  1  0
 10 11  1  0
 15 38  1  0
 15 39  1  0
  8 33  1  1
 18 43  1  0
 18 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  6
 17 41  1  0
 17 42  1  0
 12 37  1  0
 25 49  1  0
 25 50  1  0
 25 51  1  0
 23 48  1  0
  4 30  1  0
  4 31  1  0
  4 32  1  0
  2 29  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
 11 34  1  0
 11 35  1  0
 11 36  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -2.978  -1.469  -4.072  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.954  -1.128  -3.037  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.502   0.095  -2.690  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.960   1.398  -3.280  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.451   0.263  -1.633  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.049   1.345  -1.361  0.00  0.00           O+0
HETATM    7  O   UNK     0      -0.158  -0.912  -1.030  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.858  -0.896  -0.009  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.910  -1.922  -0.318  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.583  -2.260  -1.529  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.386  -1.668  -2.873  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.469  -3.266  -1.187  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.397  -3.556   0.139  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.458  -2.731   0.650  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.125  -2.798   2.087  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.291  -1.550   2.486  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.221  -0.360   2.797  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.446   0.864   3.269  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.358   1.280   2.285  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.570   0.127   1.871  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.564  -0.126   2.992  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.323  -0.524   4.118  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.834   0.137   2.624  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.191  -1.165   1.415  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.829  -2.332   1.280  0.00  0.00           C+0
HETATM   26  H   UNK     0      -2.552  -2.181  -4.787  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.337  -0.610  -4.641  0.00  0.00           H+0
HETATM   28  H   UNK     0      -3.841  -1.944  -3.594  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.550  -2.010  -2.539  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.789   1.290  -3.982  0.00  0.00           H+0
HETATM   31  H   UNK     0      -1.136   1.882  -3.815  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.304   2.074  -2.489  0.00  0.00           H+0
HETATM   33  H   UNK     0       1.385   0.064   0.007  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.385  -0.574  -2.818  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.432  -1.995  -3.298  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.184  -1.967  -3.560  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.190  -3.845  -1.748  0.00  0.00           H+0
HETATM   38  H   UNK     0       3.033  -2.874   2.696  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.537  -3.705   2.271  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.790  -1.810   3.428  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.933  -0.646   3.582  0.00  0.00           H+0
HETATM   42  H   UNK     0       2.821  -0.093   1.920  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.140   1.699   3.416  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.003   0.657   4.250  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.228   2.094   2.731  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.834   1.706   1.395  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.169   0.491   1.026  0.00  0.00           H+0
HETATM   48  H   UNK     0      -3.360  -0.060   3.428  0.00  0.00           H+0
HETATM   49  H   UNK     0      -1.181  -2.674   2.259  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.398  -3.203   0.776  0.00  0.00           H+0
HETATM   51  H   UNK     0      -1.709  -2.026   0.702  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    3    1   29                                                  
CONECT    3    5    4    2                                                  
CONECT    4    3   30   31   32                                             
CONECT    5    7    6    3                                                  
CONECT    6    5                                                            
CONECT    7    8    5                                                       
CONECT    8    9    7   24   33                                             
CONECT    9    8   10   14                                                  
CONECT   10    9   12   11                                                  
CONECT   11   10   34   35   36                                             
CONECT   12   10   13   37                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15    9                                                  
CONECT   15   14   16   38   39                                             
CONECT   16   17   40   24   15                                             
CONECT   17   18   16   41   42                                             
CONECT   18   19   17   43   44                                             
CONECT   19   18   20   45   46                                             
CONECT   20   19   21   24   47                                             
CONECT   21   20   23   22                                                  
CONECT   22   21                                                            
CONECT   23   21   48                                                       
CONECT   24   25   20   16    8                                             
CONECT   25   24   49   50   51                                             
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    2                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    4                                                            
CONECT   33    8                                                            
CONECT   34   11                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   15                                                            
CONECT   39   15                                                            
CONECT   40   16                                                            
CONECT   41   17                                                            
CONECT   42   17                                                            
CONECT   43   18                                                            
CONECT   44   18                                                            
CONECT   45   19                                                            
CONECT   46   19                                                            
CONECT   47   20                                                            
CONECT   48   23                                                            
CONECT   49   25                                                            
CONECT   50   25                                                            
CONECT   51   25                                                            
MASTER        0    0    0    0    0    0    0    0   51    0  106    0
END

RDKit          3D

51 53  0  0  0  0  0  0  0  0999 V2000
   -2.9785   -1.4693   -4.0723 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9536   -1.1283   -3.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5016    0.0947   -2.6896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9600    1.3978   -3.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4506    0.2632   -1.6327 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0494    1.3447   -1.3607 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580   -0.9120   -1.0302 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8575   -0.8964   -0.0088 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.2905   -1.5498    2.4860 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2206   -0.3602    2.7973 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4460    0.8635    3.2689 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575    1.2803    2.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697    0.1273    1.8706 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5644   -0.1259    2.9919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3226   -0.5238    4.1183 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8339    0.1365    2.6241 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1911   -1.1651    1.4153 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8294   -2.3318    1.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5522   -2.1810   -4.7867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3374   -0.6100   -4.6407 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8407   -1.9444   -3.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5499   -2.0097   -2.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7886    1.2903   -3.9824 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.3039    2.0738   -2.4890 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3849    0.0641    0.0070 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3846   -0.5743   -2.8177 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4321   -1.9954   -3.2984 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1843   -1.9671   -3.5599 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1900   -3.8455   -1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0326   -2.8735    2.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5371   -3.7048    2.2709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7896   -1.8098    3.4283 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9326   -0.6461    3.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -0.0926    1.9204 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1403    1.6992    3.4161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0033    0.6573    4.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2284    2.0944    2.7309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8336    1.7057    1.3945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1687    0.4909    1.0255 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3602   -0.0599    3.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1810   -2.6735    2.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3983   -3.2028    0.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7090   -2.0265    0.7015 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  9  1  0
  9 10  1  0
 10 12  2  0
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  8  7  1  0
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 11 36  1  0
M  END

View in JSmol

Synonyms

Value	Source
(4S,4AS,5S,8ar)-3,4a-dimethyl-4-{[(2E)-2-methylbut-2-enoyl]oxy}-4H,4ah,5H,6H,7H,8H,8ah,9H-naphtho[2,3-b]furan-5-carboxylate	Generator
4,4a,5,6,7,8,8Abeta,9-octahydro-3,4abeta-dimethyl-4b-(2-methyl-2-butenoyloxy)naphtho[2,3-b]furan-5b-carboxylate	Generator
4,4a,5,6,7,8,8Abeta,9-octahydro-3,4abeta-dimethyl-4b-(2-methyl-2-butenoyloxy)naphtho[2,3-b]furan-5b-carboxylic acid	Generator
4,4a,5,6,7,8,8Abeta,9-octahydro-3,4abeta-dimethyl-4beta-(2-methyl-2-butenoyloxy)naphtho[2,3-b]furan-5beta-carboxylate	Generator
4,4a,5,6,7,8,8Abeta,9-octahydro-3,4abeta-dimethyl-4β-(2-methyl-2-butenoyloxy)naphtho[2,3-b]furan-5β-carboxylate	Generator
4,4a,5,6,7,8,8Abeta,9-octahydro-3,4abeta-dimethyl-4β-(2-methyl-2-butenoyloxy)naphtho[2,3-b]furan-5β-carboxylic acid	Generator

Chemical Formula

C₂₀H₂₆O₅

Average Mass

346.4230 Da

Monoisotopic Mass

346.17802 Da

IUPAC Name

(4S,4aS,5S,8aR)-3,4a-dimethyl-4-{[(2E)-2-methylbut-2-enoyl]oxy}-4H,4aH,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-5-carboxylic acid

Traditional Name

(4S,4aS,5S,8aR)-3,4a-dimethyl-4-{[(2E)-2-methylbut-2-enoyl]oxy}-4H,5H,6H,7H,8H,8aH,9H-naphtho[2,3-b]furan-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)[C@@]1([H])C([H])([H])C([H])([H])C([H])([H])[C@]2([H])C([H])([H])C3=C(C(=C([H])O3)C([H])([H])[H])[C@@]([H])(OC(=O)C(=C(/[H])C([H])([H])[H])\C([H])([H])[H])[C@]12C([H])([H])[H]

InChI Identifier

InChI=1S/C20H26O5/c1-5-11(2)19(23)25-17-16-12(3)10-24-15(16)9-13-7-6-8-14(18(21)22)20(13,17)4/h5,10,13-14,17H,6-9H2,1-4H3,(H,21,22)/b11-5+/t13-,14-,17-,20+/m1/s1

InChI Key

YOHUCVRCSMMGNP-QZQBWGCWSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, C₆D₆ at 65 C, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ligularia vellerea	JEOL database	Tori, M., et al, Phytochem. 69, 1158 (2008)

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
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Heteroaromatic compound
Furan
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organooxygen 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	4.19	ALOGPS
logP	4.5	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	4.76	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.74 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.53 m³·mol⁻¹	ChemAxon
Polarizability	37.49 Å³	ChemAxon
Number of Rings	3	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

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

102078184

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Tori, M., et al. (2008). Tori, M., et al, Phytochem. 69, 1158 (2008). Phytochem..

Showing NP-Card for 6beta-angeloyloxyfuranoeremophilan-15-oic acid (NP0025330)

MOL for NP0025330 (6beta-angeloyloxyfuranoeremophilan-15-oic acid)

3D MOL for NP0025330 (6beta-angeloyloxyfuranoeremophilan-15-oic acid)

3D SDF for NP0025330 (6beta-angeloyloxyfuranoeremophilan-15-oic acid)

3D-SDF for NP0025330 (6beta-angeloyloxyfuranoeremophilan-15-oic acid)

PDB for NP0025330 (6beta-angeloyloxyfuranoeremophilan-15-oic acid)

3D PDB for NP0025330 (6beta-angeloyloxyfuranoeremophilan-15-oic acid)

SMILES for NP0025330 (6beta-angeloyloxyfuranoeremophilan-15-oic acid)

INCHI for NP0025330 (6beta-angeloyloxyfuranoeremophilan-15-oic acid)

Structure for NP0025330 (6beta-angeloyloxyfuranoeremophilan-15-oic acid)

3D Structure for NP0025330 (6beta-angeloyloxyfuranoeremophilan-15-oic acid)