NP-MRD: Showing NP-Card for Xyloallenolide B (NP0007766)

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Record Information

Version

2.0

Created at

2020-12-09 04:33:31 UTC

Updated at

2021-07-15 16:58:29 UTC

NP-MRD ID

NP0007766

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Xyloallenolide B

Provided By

NPAtlas

Description

5-({[4-(Buta-2,3-dien-1-yloxy)phenyl]methoxy}methyl)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring. Xyloallenolide B is found in Xylaria. Xyloallenolide B was first documented in 2008 (PMID: 18500842). Based on a literature review very few articles have been published on 5-({[4-(buta-2,3-dien-1-yloxy)phenyl]methoxy}methyl)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242119023D          

 50 52  0  0  0  0            999 V2000
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    6.3828    2.7123    0.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242119023D          

 50 52  0  0  0  0            999 V2000
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   -6.3861    1.9004    2.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0941   -1.0889    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266    0.1505    1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  3  0  0  0
 21 23  1  0  0  0  0
 20 24  1  0  0  0  0
  9 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26  6  1  0  0  0  0
 18 13  1  0  0  0  0
 24 16  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  3 29  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  7 32  1  0  0  0  0
  8 33  1  0  0  0  0
 10 34  1  0  0  0  0
 10 35  1  0  0  0  0
 12 36  1  0  0  0  0
 12 37  1  0  0  0  0
 14 38  1  0  0  0  0
 15 39  1  0  0  0  0
 18 40  1  0  0  0  0
 19 41  1  0  0  0  0
 19 42  1  0  0  0  0
 20 43  1  6  0  0  0
 22 44  1  0  0  0  0
 22 45  1  0  0  0  0
 23 46  1  0  0  0  0
 23 47  1  0  0  0  0
 23 48  1  0  0  0  0
 25 49  1  0  0  0  0
 26 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0007766

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C([H])=C=C([H])C([H])([H])OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])OC([H])([H])C1=C([H])C([H])=C2O[C@]([H])(C(=C([H])[H])C([H])([H])[H])C([H])([H])C2=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O3/c1-4-5-12-25-21-9-6-18(7-10-21)15-24-16-19-8-11-22-20(13-19)14-23(26-22)17(2)3/h5-11,13,23H,1-2,12,14-16H2,3H3/t23-/m0/s1

> <INCHI_KEY>
UXMKTBMXHHRKAM-UHFFFAOYSA-N

> <FORMULA>
C23H24O3

> <MOLECULAR_WEIGHT>
348.442

> <EXACT_MASS>
348.172544633

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
40.75468776055403

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-5-({[4-(buta-2,3-dien-1-yloxy)phenyl]methoxy}methyl)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran

> <ALOGPS_LOGP>
5.19

> <JCHEM_LOGP>
5.300591630333333

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.035941653774688

> <JCHEM_POLAR_SURFACE_AREA>
27.69

> <JCHEM_REFRACTIVITY>
105.033

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.12e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-5-({[4-(buta-2,3-dien-1-yloxy)phenyl]methoxy}methyl)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran

> <JCHEM_VEBER_RULE>
1

$$$$

     RDKit          3D

 50 52  0  0  0  0  0  0  0  0999 V2000
    6.9838    3.3394    1.8608 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3828    2.7123    0.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8686    2.0259   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6650    0.9263   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8528    0.0615   -1.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7923   -0.6019   -0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370   -1.4317   -1.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -2.1353   -1.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176   -2.0043    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -2.7344    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -1.8774    0.7623 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0424   -1.4354   -0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1365   -0.5413   -0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996    0.7996   -0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858    1.6534    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2694    1.1545   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5212   -0.1915   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4281   -1.0183   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9949   -0.3701   -0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4808    1.0070   -0.5558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8151    1.3056   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7915    1.6326   -0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0652    1.2402    1.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4962    1.8251    0.0947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3731   -1.1784    0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4604   -0.4754    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5970    4.1451    1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7677    2.9468    2.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9110    2.3667   -0.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4622    1.2933   -1.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2077    0.3933    0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253   -1.5108   -2.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3778   -2.7718   -1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1717   -3.6023    0.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983   -3.0409    1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -2.2885   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872   -0.8395   -0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0712    1.2500   -0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625    2.7113    0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5656   -2.0787   -0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2730   -0.7067    0.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2852   -1.1027   -1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3807    1.1696   -1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6655    1.6958   -1.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8076    1.8640   -0.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0196    0.1845    1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1010    1.5963    1.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3861    1.9004    2.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0941   -1.0889    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266    0.1505    1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  3
 21 23  1  0
 20 24  1  0
  9 25  1  0
 25 26  2  0
 26  6  1  0
 18 13  1  0
 24 16  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  6
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 25 49  1  0
 26 50  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       6.984   3.339   1.861  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.383   2.712   0.869  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.869   2.026  -0.122  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.665   0.926  -0.644  0.00  0.00           C+0
HETATM    5  O   UNK     0       5.853   0.062  -1.393  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.792  -0.602  -0.841  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.037  -1.432  -1.663  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.950  -2.135  -1.173  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.618  -2.004   0.158  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.465  -2.734   0.731  0.00  0.00           C+0
HETATM   11  O   UNK     0       0.374  -1.877   0.762  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.042  -1.435  -0.513  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.137  -0.541  -0.347  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.900   0.800  -0.139  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.986   1.653   0.019  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.269   1.155  -0.036  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.521  -0.192  -0.245  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.428  -1.018  -0.398  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.995  -0.370  -0.244  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.481   1.007  -0.556  0.00  0.00           C+0
HETATM   21  C   UNK     0      -6.815   1.306  -0.029  0.00  0.00           C+0
HETATM   22  C   UNK     0      -7.792   1.633  -0.861  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.065   1.240   1.429  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.496   1.825   0.095  0.00  0.00           O+0
HETATM   25  C   UNK     0       3.373  -1.178   0.967  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.460  -0.475   0.475  0.00  0.00           C+0
HETATM   27  H   UNK     0       7.597   4.145   1.558  0.00  0.00           H+0
HETATM   28  H   UNK     0       6.768   2.947   2.818  0.00  0.00           H+0
HETATM   29  H   UNK     0       4.911   2.367  -0.428  0.00  0.00           H+0
HETATM   30  H   UNK     0       7.462   1.293  -1.352  0.00  0.00           H+0
HETATM   31  H   UNK     0       7.208   0.393   0.157  0.00  0.00           H+0
HETATM   32  H   UNK     0       4.325  -1.511  -2.699  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.378  -2.772  -1.823  0.00  0.00           H+0
HETATM   34  H   UNK     0       1.172  -3.602   0.106  0.00  0.00           H+0
HETATM   35  H   UNK     0       1.698  -3.041   1.779  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.232  -2.289  -1.176  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.887  -0.840  -0.953  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.071   1.250  -0.086  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.863   2.711   0.185  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.566  -2.079  -0.564  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.273  -0.707   0.776  0.00  0.00           H+0
HETATM   42  H   UNK     0      -5.285  -1.103  -1.023  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.381   1.170  -1.641  0.00  0.00           H+0
HETATM   44  H   UNK     0      -7.665   1.696  -1.934  0.00  0.00           H+0
HETATM   45  H   UNK     0      -8.808   1.864  -0.505  0.00  0.00           H+0
HETATM   46  H   UNK     0      -7.020   0.185   1.798  0.00  0.00           H+0
HETATM   47  H   UNK     0      -8.101   1.596   1.685  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.386   1.900   2.016  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.094  -1.089   2.014  0.00  0.00           H+0
HETATM   50  H   UNK     0       5.027   0.151   1.131  0.00  0.00           H+0
CONECT    1    2   27   28                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   29                                                  
CONECT    4    3    5   30   31                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   26                                                  
CONECT    7    6    8   32                                                  
CONECT    8    7    9   33                                                  
CONECT    9    8   10   25                                                  
CONECT   10    9   11   34   35                                             
CONECT   11   10   12                                                       
CONECT   12   11   13   36   37                                             
CONECT   13   12   14   18                                                  
CONECT   14   13   15   38                                                  
CONECT   15   14   16   39                                                  
CONECT   16   15   17   24                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13   40                                                  
CONECT   19   17   20   41   42                                             
CONECT   20   19   21   24   43                                             
CONECT   21   20   22   23                                                  
CONECT   22   21   44   45                                                  
CONECT   23   21   46   47   48                                             
CONECT   24   20   16                                                       
CONECT   25    9   26   49                                                  
CONECT   26   25    6   50                                                  
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    3                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    7                                                            
CONECT   33    8                                                            
CONECT   34   10                                                            
CONECT   35   10                                                            
CONECT   36   12                                                            
CONECT   37   12                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   18                                                            
CONECT   41   19                                                            
CONECT   42   19                                                            
CONECT   43   20                                                            
CONECT   44   22                                                            
CONECT   45   22                                                            
CONECT   46   23                                                            
CONECT   47   23                                                            
CONECT   48   23                                                            
CONECT   49   25                                                            
CONECT   50   26                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  104    0
END

RDKit          3D

50 52  0  0  0  0  0  0  0  0999 V2000
    6.9838    3.3394    1.8608 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3828    2.7123    0.8690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8686    2.0259   -0.1220 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6650    0.9263   -0.6441 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8528    0.0615   -1.3932 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7923   -0.6019   -0.8406 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0370   -1.4317   -1.6628 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9500   -2.1353   -1.1727 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6176   -2.0043    0.1578 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4652   -2.7344    0.7306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -1.8774    0.7623 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0424   -1.4354   -0.5125 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1365   -0.5413   -0.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8996    0.7996   -0.1385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858    1.6534    0.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2694    1.1545   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5212   -0.1915   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4281   -1.0183   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9949   -0.3701   -0.2442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4808    1.0070   -0.5558 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.8151    1.3056   -0.0292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7915    1.6326   -0.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0652    1.2402    1.4286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4962    1.8251    0.0947 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3731   -1.1784    0.9671 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4604   -0.4754    0.4748 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5970    4.1451    1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7677    2.9468    2.8180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9110    2.3667   -0.4275 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4622    1.2933   -1.3517 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2077    0.3933    0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253   -1.5108   -2.6994 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3778   -2.7718   -1.8230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1717   -3.6023    0.1056 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6983   -3.0409    1.7787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2315   -2.2885   -1.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8872   -0.8395   -0.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0712    1.2500   -0.0857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8625    2.7113    0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5656   -2.0787   -0.5641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2730   -0.7067    0.7758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2852   -1.1027   -1.0231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3807    1.1696   -1.6411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6655    1.6958   -1.9344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8076    1.8640   -0.5053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0196    0.1845    1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1010    1.5963    1.6852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3861    1.9004    2.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0941   -1.0889    2.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0266    0.1505    1.1305 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  3
 21 23  1  0
 20 24  1  0
  9 25  1  0
 25 26  2  0
 26  6  1  0
 18 13  1  0
 24 16  1  0
  1 27  1  0
  1 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  7 32  1  0
  8 33  1  0
 10 34  1  0
 10 35  1  0
 12 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 18 40  1  0
 19 41  1  0
 19 42  1  0
 20 43  1  6
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
 23 48  1  0
 25 49  1  0
 26 50  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Xyloallenolide b	MeSH

Chemical Formula

C₂₃H₂₄O₃

Average Mass

348.4420 Da

Monoisotopic Mass

348.17254 Da

IUPAC Name

(2S)-5-({[4-(buta-2,3-dien-1-yloxy)phenyl]methoxy}methyl)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran

Traditional Name

(2S)-5-({[4-(buta-2,3-dien-1-yloxy)phenyl]methoxy}methyl)-2-(prop-1-en-2-yl)-2,3-dihydro-1-benzofuran

CAS Registry Number

Not Available

SMILES

CC(=C)C1CC2=C(O1)C=CC(COCC1=CC=C(OCC=C=C)C=C1)=C2

InChI Identifier

InChI=1S/C23H24O3/c1-4-5-12-25-21-9-6-18(7-10-21)15-24-16-19-8-11-22-20(13-19)14-23(26-22)17(2)3/h5-11,13,23H,1-2,12,14-16H2,3H3

InChI Key

UXMKTBMXHHRKAM-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Xylaria	NPAtlas	18500842

Species Where Detected

Species Name	Source	Reference
Xylaria sp. #2508	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarans. Coumarans are compounds containing the coumaran skeleton, which consists of a benzene ring fused to a 2,3-dihydrofuran ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Coumarans

Sub Class

Not Available

Direct Parent

Coumarans

Alternative Parents

Substituents

Coumaran
Benzylether
Phenoxy compound
Phenol ether
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
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	5.19	ALOGPS
logP	5.3	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	27.69 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	105.03 m³·mol⁻¹	ChemAxon
Polarizability	40.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA009747

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

24703341

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

24970515

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Xu F, Zhang Y, Wang J, Pang J, Huang C, Wu X, She Z, Vrijmoed LL, Jones EB, Lin Y: Benzofuran derivatives from the mangrove endophytic Fungus Xylaria sp. (#2508). J Nat Prod. 2008 Jul;71(7):1251-3. doi: 10.1021/np070602x. Epub 2008 May 24. [PubMed:18500842 ]

Showing NP-Card for Xyloallenolide B (NP0007766)

MOL for NP0007766 (Xyloallenolide B)

3D MOL for NP0007766 (Xyloallenolide B)

3D SDF for NP0007766 (Xyloallenolide B)

3D-SDF for NP0007766 (Xyloallenolide B)

PDB for NP0007766 (Xyloallenolide B)

3D PDB for NP0007766 (Xyloallenolide B)

SMILES for NP0007766 (Xyloallenolide B)

INCHI for NP0007766 (Xyloallenolide B)

Structure for NP0007766 (Xyloallenolide B)

3D Structure for NP0007766 (Xyloallenolide B)