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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-22 21:18:35 UTC

Update Date

2021-09-22 21:18:36 UTC

HMDB ID

HMDB0301812

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Lappaol A

Description

4-{[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]methyl}-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety. Based on a literature review very few articles have been published on 4-{[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]methyl}-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241221452D          

 39 43  0  0  0  0            999 V2000
    4.7278    2.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3922    2.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8047    1.3880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2527    0.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5852    1.9309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9721    2.4830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1437    3.2899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306    3.8420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7021    4.6489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4867    4.9039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6582    5.7108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0998    4.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8844    4.6068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4975    4.0547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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 37 38  1  0  0  0  0
 36 39  2  0  0  0  0
 18 39  1  0  0  0  0
M  END

HMDB0301812
     RDKit          3D
Lappaol A
 71 75  0  0  0  0  0  0  0  0999 V2000
    6.4613   -0.9360   -2.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6963    0.5680    3.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270    0.2983    4.1768 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4659    1.7958    1.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828    0.9856    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    0.7904   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241221452D          

 39 43  0  0  0  0            999 V2000
    4.7278    2.8561    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
  8 16  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 29 32  2  0  0  0  0
 24 32  1  0  0  0  0
 23 33  1  0  0  0  0
 20 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 21 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 36 39  2  0  0  0  0
 18 39  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301812

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CC2COC(=O)C2CC2=CC=C(O)C(OC)=C2)=CC2=C1OC(C2CO)C1=CC=C(O)C(OC)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C30H32O9/c1-35-25-11-16(4-6-23(25)32)9-20-19(15-38-30(20)34)8-17-10-21-22(14-31)28(39-29(21)27(12-17)37-3)18-5-7-24(33)26(13-18)36-2/h4-7,10-13,19-20,22,28,31-33H,8-9,14-15H2,1-3H3

> <INCHI_KEY>
PYLYQTVVQXPBIJ-UHFFFAOYSA-N

> <FORMULA>
C30H32O9

> <MOLECULAR_WEIGHT>
536.5697

> <EXACT_MASS>
536.204632622

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
56.39687426425935

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]methyl}-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
3.77041961

> <ALOGPS_LOGS>
-4.96

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.229150900939528

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.626365079534489

> <JCHEM_PKA_STRONGEST_BASIC>
-2.71366921736099

> <JCHEM_POLAR_SURFACE_AREA>
123.91000000000003

> <JCHEM_REFRACTIVITY>
142.45469999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.88e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]methyl}-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301812
     RDKit          3D
Lappaol A
 71 75  0  0  0  0  0  0  0  0999 V2000
    6.4613   -0.9360   -2.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1303   -0.7435   -1.0346 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5292   -0.7814    0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1725   -1.0246    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5619   -1.0625    1.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1181   -1.3035    1.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349   -0.1425    1.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963    0.5680    3.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270    0.2983    4.1768 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5814    1.5406    2.6372 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4659    1.7958    1.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828    0.9856    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    0.7904   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6727    0.2515   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4987   -1.1058   -0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7512   -1.6260   -1.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9426   -2.9892   -1.3441 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -3.8353   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8214   -0.7227   -1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6476    0.6275   -1.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    1.1311   -0.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9751    1.3265   -1.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0087    2.1356   -2.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2349    2.7481   -2.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9079    0.1677   -1.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8743    0.1937   -0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537   -0.1992    0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4869   -0.1607    1.9423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7767    0.2880    1.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7073    0.3267    2.6867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1236    0.6855    0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4218    1.1241    0.1636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7376    1.5250   -1.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1612    0.6293   -0.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1586   -0.9949   -1.5584 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2881   -0.8646    2.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6376   -0.6250    2.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2825   -0.5793    1.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6398   -0.3393    1.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8420   -1.8734   -2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7722   -0.1031   -2.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1501   -1.1619   -3.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059   -1.1853   -0.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8452   -2.0559    0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0061   -1.8992    2.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756   -0.4766    1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3841    1.6471    0.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139    2.9079    1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3839    1.6582    1.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928    1.8105   -1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243    0.1572   -1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3655   -1.7666   -0.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -3.5297   -1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804   -4.8793   -1.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5870   -3.8130   -0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    2.1817   -0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1268    1.9223   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    1.4260   -3.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687    2.8587   -2.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1994    3.7348   -2.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4956    0.2203   -2.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5655   -0.5453    1.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2446   -0.4663    2.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4654    0.0378    3.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0157    2.2799   -1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7795    1.8922   -1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6691    0.6433   -1.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4653    0.9492   -1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8236   -0.8915    3.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2173   -0.4670    3.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0594   -0.3163    0.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 31 34  2  0
 25 35  1  0
  5 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 38  3  1  0
 12  7  1  0
 21 14  1  0
 34 26  1  0
 35 19  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  4 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 18 53  1  0
 18 54  1  0
 18 55  1  0
 21 56  1  0
 22 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 25 61  1  0
 27 62  1  0
 28 63  1  0
 30 64  1  0
 33 65  1  0
 33 66  1  0
 33 67  1  0
 34 68  1  0
 36 69  1  0
 37 70  1  0
 39 71  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0       8.825   5.331   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       8.199   3.925   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.969   2.591   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       7.938   1.446   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.692   3.604   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.548   4.635   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.868   6.141   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.724   7.172   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.044   8.678   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.509   9.154   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.829  10.660   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.653   8.123   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.118   8.599   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      10.262   7.569   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.333   6.617   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.023   1.509   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.793   2.843   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -7.333   2.843   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -5.023   4.176   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -5.793   5.510   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.023   6.844   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.483   4.176   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.744   0.132   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       0.287  -1.012   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    2    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   16                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14                                                            
CONECT   16   13    8                                                       
CONECT   17    5   18                                                       
CONECT   18   17   19   39                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   33                                                  
CONECT   21   20   22   36                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   33                                                  
CONECT   24   23   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29   31                                                       
CONECT   31   30                                                            
CONECT   32   29   24                                                       
CONECT   33   23   20   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   21   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36   18                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

COMPND    HMDB0301812
HETATM    1  C1  UNL     1       6.461  -0.936  -2.259  1.00  0.00           C  
HETATM    2  O1  UNL     1       7.130  -0.743  -1.035  1.00  0.00           O  
HETATM    3  C2  UNL     1       6.529  -0.781   0.196  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.172  -1.025   0.242  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.562  -1.062   1.500  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.118  -1.303   1.637  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.235  -0.143   1.771  1.00  0.00           C  
HETATM    8  C7  UNL     1       2.696   0.568   3.031  1.00  0.00           C  
HETATM    9  O2  UNL     1       2.327   0.298   4.177  1.00  0.00           O  
HETATM   10  O3  UNL     1       3.581   1.541   2.637  1.00  0.00           O  
HETATM   11  C8  UNL     1       3.466   1.796   1.235  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.283   0.986   0.839  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.041   0.790  -0.599  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.673   0.252  -0.865  1.00  0.00           C  
HETATM   15  C12 UNL     1       0.499  -1.106  -0.986  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.751  -1.626  -1.220  1.00  0.00           C  
HETATM   17  O4  UNL     1      -0.943  -2.989  -1.344  1.00  0.00           O  
HETATM   18  C14 UNL     1       0.183  -3.835  -1.224  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.821  -0.723  -1.327  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.648   0.628  -1.207  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.377   1.131  -0.970  1.00  0.00           C  
HETATM   22  C18 UNL     1      -2.975   1.327  -1.370  1.00  0.00           C  
HETATM   23  C19 UNL     1      -3.009   2.136  -2.630  1.00  0.00           C  
HETATM   24  O5  UNL     1      -4.235   2.748  -2.728  1.00  0.00           O  
HETATM   25  C20 UNL     1      -3.908   0.168  -1.494  1.00  0.00           C  
HETATM   26  C21 UNL     1      -4.874   0.194  -0.371  1.00  0.00           C  
HETATM   27  C22 UNL     1      -4.554  -0.199   0.912  1.00  0.00           C  
HETATM   28  C23 UNL     1      -5.487  -0.161   1.942  1.00  0.00           C  
HETATM   29  C24 UNL     1      -6.777   0.288   1.661  1.00  0.00           C  
HETATM   30  O6  UNL     1      -7.707   0.327   2.687  1.00  0.00           O  
HETATM   31  C25 UNL     1      -7.124   0.685   0.391  1.00  0.00           C  
HETATM   32  O7  UNL     1      -8.422   1.124   0.164  1.00  0.00           O  
HETATM   33  C26 UNL     1      -8.738   1.525  -1.160  1.00  0.00           C  
HETATM   34  C27 UNL     1      -6.161   0.629  -0.600  1.00  0.00           C  
HETATM   35  O8  UNL     1      -3.159  -0.995  -1.558  1.00  0.00           O  
HETATM   36  C28 UNL     1       5.288  -0.865   2.652  1.00  0.00           C  
HETATM   37  C29 UNL     1       6.638  -0.625   2.566  1.00  0.00           C  
HETATM   38  C30 UNL     1       7.282  -0.579   1.332  1.00  0.00           C  
HETATM   39  O9  UNL     1       8.640  -0.339   1.227  1.00  0.00           O  
HETATM   40  H1  UNL     1       5.842  -1.873  -2.136  1.00  0.00           H  
HETATM   41  H2  UNL     1       5.772  -0.103  -2.497  1.00  0.00           H  
HETATM   42  H3  UNL     1       7.150  -1.162  -3.090  1.00  0.00           H  
HETATM   43  H4  UNL     1       4.606  -1.185  -0.670  1.00  0.00           H  
HETATM   44  H5  UNL     1       2.845  -2.056   0.868  1.00  0.00           H  
HETATM   45  H6  UNL     1       3.006  -1.899   2.606  1.00  0.00           H  
HETATM   46  H7  UNL     1       1.176  -0.477   1.913  1.00  0.00           H  
HETATM   47  H8  UNL     1       4.384   1.647   0.676  1.00  0.00           H  
HETATM   48  H9  UNL     1       3.214   2.908   1.199  1.00  0.00           H  
HETATM   49  H10 UNL     1       1.384   1.658   1.186  1.00  0.00           H  
HETATM   50  H11 UNL     1       2.093   1.811  -1.086  1.00  0.00           H  
HETATM   51  H12 UNL     1       2.724   0.157  -1.155  1.00  0.00           H  
HETATM   52  H13 UNL     1       1.365  -1.767  -0.904  1.00  0.00           H  
HETATM   53  H14 UNL     1       0.993  -3.530  -1.944  1.00  0.00           H  
HETATM   54  H15 UNL     1      -0.080  -4.879  -1.515  1.00  0.00           H  
HETATM   55  H16 UNL     1       0.587  -3.813  -0.170  1.00  0.00           H  
HETATM   56  H17 UNL     1      -0.195   2.182  -0.869  1.00  0.00           H  
HETATM   57  H18 UNL     1      -3.127   1.922  -0.455  1.00  0.00           H  
HETATM   58  H19 UNL     1      -2.908   1.426  -3.483  1.00  0.00           H  
HETATM   59  H20 UNL     1      -2.169   2.859  -2.673  1.00  0.00           H  
HETATM   60  H21 UNL     1      -4.199   3.735  -2.747  1.00  0.00           H  
HETATM   61  H22 UNL     1      -4.496   0.220  -2.456  1.00  0.00           H  
HETATM   62  H23 UNL     1      -3.566  -0.545   1.138  1.00  0.00           H  
HETATM   63  H24 UNL     1      -5.245  -0.466   2.949  1.00  0.00           H  
HETATM   64  H25 UNL     1      -7.465   0.038   3.622  1.00  0.00           H  
HETATM   65  H26 UNL     1      -8.016   2.280  -1.541  1.00  0.00           H  
HETATM   66  H27 UNL     1      -9.779   1.892  -1.252  1.00  0.00           H  
HETATM   67  H28 UNL     1      -8.669   0.643  -1.862  1.00  0.00           H  
HETATM   68  H29 UNL     1      -6.465   0.949  -1.589  1.00  0.00           H  
HETATM   69  H30 UNL     1       4.824  -0.891   3.651  1.00  0.00           H  
HETATM   70  H31 UNL     1       7.217  -0.467   3.481  1.00  0.00           H  
HETATM   71  H32 UNL     1       9.059  -0.316   0.311  1.00  0.00           H  
CONECT    1    2   40   41   42
CONECT    2    3
CONECT    3    4    4   38
CONECT    4    5   43
CONECT    5    6   36   36
CONECT    6    7   44   45
CONECT    7    8   12   46
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   47   48
CONECT   12   13   49
CONECT   13   14   50   51
CONECT   14   15   15   21
CONECT   15   16   52
CONECT   16   17   19   19
CONECT   17   18
CONECT   18   53   54   55
CONECT   19   20   35
CONECT   20   21   21   22
CONECT   21   56
CONECT   22   23   25   57
CONECT   23   24   58   59
CONECT   24   60
CONECT   25   26   35   61
CONECT   26   27   27   34
CONECT   27   28   62
CONECT   28   29   29   63
CONECT   29   30   31
CONECT   30   64
CONECT   31   32   34   34
CONECT   32   33
CONECT   33   65   66   67
CONECT   34   68
CONECT   36   37   69
CONECT   37   38   38   70
CONECT   38   39
CONECT   39   71
END

HMDB0301812
     RDKit          3D
Lappaol A
 71 75  0  0  0  0  0  0  0  0999 V2000
    6.4613   -0.9360   -2.2585 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1303   -0.7435   -1.0346 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5292   -0.7814    0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1725   -1.0246    0.2416 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5619   -1.0625    1.4999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1181   -1.3035    1.6367 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2349   -0.1425    1.7706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6963    0.5680    3.0314 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3270    0.2983    4.1768 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5814    1.5406    2.6372 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4659    1.7958    1.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828    0.9856    0.8394 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0408    0.7904   -0.5987 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6727    0.2515   -0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4987   -1.1058   -0.9860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7512   -1.6260   -1.2199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9426   -2.9892   -1.3441 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -3.8353   -1.2241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8214   -0.7227   -1.3274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6476    0.6275   -1.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3768    1.1311   -0.9704 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9751    1.3265   -1.3697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0087    2.1356   -2.6301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2349    2.7481   -2.7278 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9079    0.1677   -1.4941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8743    0.1937   -0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5537   -0.1992    0.9124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4869   -0.1607    1.9423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7767    0.2880    1.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7073    0.3267    2.6867 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1236    0.6855    0.3914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4218    1.1241    0.1636 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7376    1.5250   -1.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1612    0.6293   -0.5999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1586   -0.9949   -1.5584 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2881   -0.8646    2.6520 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6376   -0.6250    2.5659 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2825   -0.5793    1.3315 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6398   -0.3393    1.2269 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8420   -1.8734   -2.1364 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7722   -0.1031   -2.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1501   -1.1619   -3.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6059   -1.1853   -0.6703 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8452   -2.0559    0.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0061   -1.8992    2.6056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756   -0.4766    1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3841    1.6471    0.6763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139    2.9079    1.1991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3839    1.6582    1.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0928    1.8105   -1.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7243    0.1572   -1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3655   -1.7666   -0.9042 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934   -3.5297   -1.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0804   -4.8793   -1.5151 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5870   -3.8130   -0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1953    2.1817   -0.8691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1268    1.9223   -0.4553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9078    1.4260   -3.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1687    2.8587   -2.6733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1994    3.7348   -2.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4956    0.2203   -2.4562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5655   -0.5453    1.1382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2446   -0.4663    2.9495 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4654    0.0378    3.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0157    2.2799   -1.5408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7795    1.8922   -1.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6691    0.6433   -1.8623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4653    0.9492   -1.5890 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8236   -0.8915    3.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2173   -0.4670    3.4814 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0594   -0.3163    0.3108 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 16 19  2  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 22 25  1  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  1  0
 31 34  2  0
 25 35  1  0
  5 36  2  0
 36 37  1  0
 37 38  2  0
 38 39  1  0
 38  3  1  0
 12  7  1  0
 21 14  1  0
 34 26  1  0
 35 19  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  4 43  1  0
  6 44  1  0
  6 45  1  0
  7 46  1  0
 11 47  1  0
 11 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 18 53  1  0
 18 54  1  0
 18 55  1  0
 21 56  1  0
 22 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 25 61  1  0
 27 62  1  0
 28 63  1  0
 30 64  1  0
 33 65  1  0
 33 66  1  0
 33 67  1  0
 34 68  1  0
 36 69  1  0
 37 70  1  0
 39 71  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₀H₃₂O₉

Average Molecular Weight

536.5697

Monoisotopic Molecular Weight

536.204632622

IUPAC Name

4-{[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]methyl}-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

Traditional Name

4-{[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]methyl}-3-[(4-hydroxy-3-methoxyphenyl)methyl]oxolan-2-one

CAS Registry Number

62333-08-8

SMILES

COC1=CC(CC2COC(=O)C2CC2=CC=C(O)C(OC)=C2)=CC2=C1OC(C2CO)C1=CC=C(O)C(OC)=C1

InChI Identifier

InChI=1S/C30H32O9/c1-35-25-11-16(4-6-23(25)32)9-20-19(15-38-30(20)34)8-17-10-21-22(14-31)28(39-29(21)27(12-17)37-3)18-5-7-24(33)26(13-18)36-2/h4-7,10-13,19-20,22,28,31-33H,8-9,14-15H2,1-3H3

InChI Key

PYLYQTVVQXPBIJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-arylbenzofuran flavonoids. These are phenylpropanoids containing the 2-phenylbenzofuran moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

2-arylbenzofuran flavonoids

Sub Class

Not Available

Direct Parent

2-arylbenzofuran flavonoids

Alternative Parents

Substituents

2-arylbenzofuran flavonoid
Dibenzylbutyrolactone
Lignan lactone
Tetrahydrofuran lignan
9,9p-epoxylignan
Furanoid lignan
Norlignan skeleton
Neolignan skeleton
Methoxyphenol
Coumaran
Benzofuran
Methoxybenzene
Phenoxy compound
Anisole
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Tetrahydrofuran
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Ether
Carboxylic acid derivative
Primary alcohol
Carbonyl group
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Burdock (FooDB: FOOD00017)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.59	ALOGPS
logP	3.77	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	9.63	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	123.91 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	142.45 m³·mol⁻¹	ChemAxon
Polarizability	56.4 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	230.964	32859911
AllCCS	[M+H-H2O]+	229.032	32859911
AllCCS	[M+Na]+	233.235	32859911
AllCCS	[M+NH4]+	232.731	32859911
AllCCS	[M-H]-	228.079	32859911
AllCCS	[M+Na-2H]-	230.038	32859911
AllCCS	[M+HCOO]-	232.348	32859911
DeepCCS	[M+H]+	214.989	30932474
DeepCCS	[M-H]-	212.594	30932474
DeepCCS	[M-2H]-	245.477	30932474
DeepCCS	[M+Na]+	220.902	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lappaol A 10V, Positive-QTOF	splash10-00kr-0003290000-742ec8a7034acea94f43	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lappaol A 20V, Positive-QTOF	splash10-00kr-0339760000-e4f8621120d527af08bf	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lappaol A 40V, Positive-QTOF	splash10-0ufr-0901000000-ce7da13e2385ce5b1d6e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lappaol A 10V, Negative-QTOF	splash10-000i-0000090000-8424fc7c6457ea442f7b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lappaol A 20V, Negative-QTOF	splash10-00kr-0102790000-b640934d15897ef3c9f4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lappaol A 40V, Negative-QTOF	splash10-009i-0212930000-e134d447434448162274	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lappaol A 10V, Positive-QTOF	splash10-000i-0300290000-77b1e04094a6e8af3d00	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lappaol A 20V, Positive-QTOF	splash10-0a4r-1900130000-d376f86d592fac762a22	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lappaol A 40V, Positive-QTOF	splash10-00ku-3525930000-09f8d052ee8027b022ea	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lappaol A 10V, Negative-QTOF	splash10-000i-0000090000-6375bcd31d9df5a121f6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lappaol A 20V, Negative-QTOF	splash10-00kr-0101690000-abdb5e7927777489613e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Lappaol A 40V, Negative-QTOF	splash10-0f8a-1427390000-46820c472af216b59a8e	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001449

KNApSAcK ID

Not Available

Chemspider ID

286852

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

323894

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Lappaol A (HMDB0301812)

MOL for HMDB0301812 (Lappaol A)

3D MOL for HMDB0301812 (Lappaol A)

3D SDF for HMDB0301812 (Lappaol A)

3D-SDF for HMDB0301812 (Lappaol A)

PDB for HMDB0301812 (Lappaol A)

3D PDB for HMDB0301812 (Lappaol A)

SMILES for HMDB0301812 (Lappaol A)

INCHI for HMDB0301812 (Lappaol A)

Structure for HMDB0301812 (Lappaol A)

3D Structure for HMDB0301812 (Lappaol A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra