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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:10:57 UTC

Update Date

2022-03-07 02:54:25 UTC

HMDB ID

HMDB0035230

Secondary Accession Numbers

HMDB35230

Metabolite Identification

Common Name

Aurantricholide B

Description

Aurantricholide B belongs to the class of organic compounds known as furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moiety. Aurantricholide B has been detected, but not quantified in, a few different foods, such as common mushrooms (Agaricus bisporus), mushrooms, and oyster mushrooms (Pleurotus ostreatus). This could make aurantricholide b a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Aurantricholide B.

Structure

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

HMDB0035230
     RDKit          3D
Aurantricholide B
 33 36  0  0  0  0  0  0  0  0999 V2000
    2.1720   -3.6484    0.1327 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1581   -2.8774    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1006   -3.2087    0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8654   -2.1437    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2270   -1.9102    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321   -0.6159    0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0900   -0.4277    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5902    0.8585    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9656    1.0795    0.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7004    1.9300    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649    3.1933   -0.0409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3286    1.7032   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8197    0.4211    0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5066    0.2268    0.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023   -0.9760    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.5038    0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4813   -0.6925    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958   -0.7753   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.0078   -1.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7950    0.8501   -0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9484    1.6104   -0.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9783    0.9215    0.9423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    0.1610    1.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9187   -2.7230    0.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7996   -1.2381    0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5829    0.2848    0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6632    4.0018   -0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7178    2.5738   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0635   -1.4257   -1.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0990   -0.0374   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8195    2.5331   -0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939    1.6164    1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114    0.2460    1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 16  2  1  0
 23 17  1  0
 15  4  1  0
 13  6  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 18 29  1  0
 19 30  1  0
 21 31  1  0
 22 32  1  0
 23 33  1  0
M  END


  Mrv0541 05061308192D          

 23 26  0  0  0  0            999 V2000
    0.1536    3.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    3.1465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1014    4.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    3.9312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9083    4.5442    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
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1633    5.3289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  4  2  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  5  1  0  0  0  0
  9  6  1  0  0  0  0
 10  3  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  2  0  0  0  0
 12  7  2  0  0  0  0
 12 11  1  0  0  0  0
 13  7  1  0  0  0  0
 13  9  2  0  0  0  0
 14  6  2  0  0  0  0
 15  8  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 15  1  0  0  0  0
 18 10  1  0  0  0  0
 19 11  1  0  0  0  0
 20 12  1  0  0  0  0
 21 17  2  0  0  0  0
 22 13  1  0  0  0  0
 22 16  1  0  0  0  0
 23 14  1  0  0  0  0
 23 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035230

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC=C(C=C1)C1=C2OC3=C(C=C2OC1=O)C=C(O)C(O)=C3

> <INCHI_IDENTIFIER>
InChI=1S/C17H10O6/c18-10-3-1-8(2-4-10)15-16-14(23-17(15)21)6-9-5-11(19)12(20)7-13(9)22-16/h1-7,18-20H

> <INCHI_KEY>
QIZCPKIKTOBRLA-UHFFFAOYSA-N

> <FORMULA>
C17H10O6

> <MOLECULAR_WEIGHT>
310.2577

> <EXACT_MASS>
310.047738052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
30.544873228563123

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7-dihydroxy-3-(4-hydroxyphenyl)-2H-furo[3,2-b]chromen-2-one

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.587445331333333

> <ALOGPS_LOGS>
-3.86

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.810676060218153

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.936994032433281

> <JCHEM_PKA_STRONGEST_BASIC>
-5.4100814194979225

> <JCHEM_POLAR_SURFACE_AREA>
96.22

> <JCHEM_REFRACTIVITY>
82.2676

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.29e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7-dihydroxy-3-(4-hydroxyphenyl)furo[3,2-b]chromen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0035230
     RDKit          3D
Aurantricholide B
 33 36  0  0  0  0  0  0  0  0999 V2000
    2.1720   -3.6484    0.1327 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1581   -2.8774    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1006   -3.2087    0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8654   -2.1437    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2270   -1.9102    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321   -0.6159    0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0900   -0.4277    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5902    0.8585    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9656    1.0795    0.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7004    1.9300    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649    3.1933   -0.0409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3286    1.7032   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8197    0.4211    0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5066    0.2268    0.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023   -0.9760    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.5038    0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4813   -0.6925    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958   -0.7753   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.0078   -1.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7950    0.8501   -0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9484    1.6104   -0.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9783    0.9215    0.9423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    0.1610    1.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9187   -2.7230    0.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7996   -1.2381    0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5829    0.2848    0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6632    4.0018   -0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7178    2.5738   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0635   -1.4257   -1.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0990   -0.0374   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8195    2.5331   -0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939    1.6164    1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114    0.2460    1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 16  2  1  0
 23 17  1  0
 15  4  1  0
 13  6  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 18 29  1  0
 19 30  1  0
 21 31  1  0
 22 32  1  0
 23 33  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       0.287   6.698   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.250   5.873   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.189   8.162   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.726   7.338   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.744   5.553   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.695   8.483   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.171   9.947   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       7.865   1.303   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -2.713   2.843   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       2.530   4.383   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -0.268   1.597   0.000  0.00  0.00           O+0
CONECT    1    3    8                                                       
CONECT    2    4    8                                                       
CONECT    3    1   10                                                       
CONECT    4    2   10                                                       
CONECT    5    9   11                                                       
CONECT    6    9   14                                                       
CONECT    7   12   13                                                       
CONECT    8    1    2   15                                                  
CONECT    9    5    6   13                                                  
CONECT   10    3    4   18                                                  
CONECT   11    5   12   19                                                  
CONECT   12    7   11   20                                                  
CONECT   13    7    9   22                                                  
CONECT   14    6   16   23                                                  
CONECT   15    8   16   17                                                  
CONECT   16   14   15   22                                                  
CONECT   17   15   21   23                                                  
CONECT   18   10                                                            
CONECT   19   11                                                            
CONECT   20   12                                                            
CONECT   21   17                                                            
CONECT   22   13   16                                                       
CONECT   23   14   17                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   52    0
END

COMPND    HMDB0035230
HETATM    1  O1  UNL     1       2.172  -3.648   0.133  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.158  -2.877   0.118  1.00  0.00           C  
HETATM    3  O2  UNL     1      -0.101  -3.209   0.162  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.865  -2.144   0.127  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.227  -1.910   0.149  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.732  -0.616   0.100  1.00  0.00           C  
HETATM    7  C5  UNL     1      -4.090  -0.428   0.129  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.590   0.859   0.082  1.00  0.00           C  
HETATM    9  O3  UNL     1      -5.966   1.080   0.112  1.00  0.00           O  
HETATM   10  C7  UNL     1      -3.700   1.930   0.005  1.00  0.00           C  
HETATM   11  O4  UNL     1      -4.265   3.193  -0.041  1.00  0.00           O  
HETATM   12  C8  UNL     1      -2.329   1.703  -0.023  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.820   0.421   0.026  1.00  0.00           C  
HETATM   14  O5  UNL     1      -0.507   0.227   0.003  1.00  0.00           O  
HETATM   15  C10 UNL     1       0.002  -0.976   0.049  1.00  0.00           C  
HETATM   16  C11 UNL     1       1.295  -1.504   0.046  1.00  0.00           C  
HETATM   17  C12 UNL     1       2.481  -0.692   0.011  1.00  0.00           C  
HETATM   18  C13 UNL     1       3.296  -0.775  -1.122  1.00  0.00           C  
HETATM   19  C14 UNL     1       4.433  -0.008  -1.199  1.00  0.00           C  
HETATM   20  C15 UNL     1       4.795   0.850  -0.174  1.00  0.00           C  
HETATM   21  O6  UNL     1       5.948   1.610  -0.279  1.00  0.00           O  
HETATM   22  C16 UNL     1       3.978   0.921   0.942  1.00  0.00           C  
HETATM   23  C17 UNL     1       2.827   0.161   1.048  1.00  0.00           C  
HETATM   24  H1  UNL     1      -2.919  -2.723   0.210  1.00  0.00           H  
HETATM   25  H2  UNL     1      -4.800  -1.238   0.190  1.00  0.00           H  
HETATM   26  H3  UNL     1      -6.583   0.285   0.174  1.00  0.00           H  
HETATM   27  H4  UNL     1      -3.663   4.002  -0.093  1.00  0.00           H  
HETATM   28  H5  UNL     1      -1.718   2.574  -0.089  1.00  0.00           H  
HETATM   29  H6  UNL     1       3.064  -1.426  -1.936  1.00  0.00           H  
HETATM   30  H7  UNL     1       5.099  -0.037  -2.052  1.00  0.00           H  
HETATM   31  H8  UNL     1       5.819   2.533  -0.719  1.00  0.00           H  
HETATM   32  H9  UNL     1       4.294   1.616   1.733  1.00  0.00           H  
HETATM   33  H10 UNL     1       2.211   0.246   1.930  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   16
CONECT    3    4
CONECT    4    5    5   15
CONECT    5    6   24
CONECT    6    7    7   13
CONECT    7    8   25
CONECT    8    9   10   10
CONECT    9   26
CONECT   10   11   12
CONECT   11   27
CONECT   12   13   13   28
CONECT   13   14
CONECT   14   15
CONECT   15   16   16
CONECT   16   17
CONECT   17   18   18   23
CONECT   18   19   29
CONECT   19   20   20   30
CONECT   20   21   22
CONECT   21   31
CONECT   22   23   23   32
CONECT   23   33
END

HMDB0035230
     RDKit          3D
Aurantricholide B
 33 36  0  0  0  0  0  0  0  0999 V2000
    2.1720   -3.6484    0.1327 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1581   -2.8774    0.1178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1006   -3.2087    0.1620 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8654   -2.1437    0.1270 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2270   -1.9102    0.1495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321   -0.6159    0.0996 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0900   -0.4277    0.1288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5902    0.8585    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9656    1.0795    0.1116 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7004    1.9300    0.0050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2649    3.1933   -0.0409 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3286    1.7032   -0.0227 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8197    0.4211    0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5066    0.2268    0.0028 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0023   -0.9760    0.0489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2950   -1.5038    0.0456 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4813   -0.6925    0.0107 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2958   -0.7753   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.0078   -1.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7950    0.8501   -0.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9484    1.6104   -0.2791 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9783    0.9215    0.9423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8268    0.1610    1.0477 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9187   -2.7230    0.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7996   -1.2381    0.1903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5829    0.2848    0.1736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6632    4.0018   -0.0929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7178    2.5738   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0635   -1.4257   -1.9361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0990   -0.0374   -2.0515 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8195    2.5331   -0.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2939    1.6164    1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2114    0.2460    1.9296 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 20 22  1  0
 22 23  2  0
 16  2  1  0
 23 17  1  0
 15  4  1  0
 13  6  1  0
  5 24  1  0
  7 25  1  0
  9 26  1  0
 11 27  1  0
 12 28  1  0
 18 29  1  0
 19 30  1  0
 21 31  1  0
 22 32  1  0
 23 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6,7-Dihydroxy-3-(4-hydroxyphenyl)-2H-furo[3,2-b][1]benzopyran-2-one, 9ci	HMDB

Chemical Formula

C₁₇H₁₀O₆

Average Molecular Weight

310.2577

Monoisotopic Molecular Weight

310.047738052

IUPAC Name

6,7-dihydroxy-3-(4-hydroxyphenyl)-2H-furo[3,2-b]chromen-2-one

Traditional Name

6,7-dihydroxy-3-(4-hydroxyphenyl)furo[3,2-b]chromen-2-one

CAS Registry Number

264923-56-0

SMILES

OC1=CC=C(C=C1)C1=C2OC3=C(C=C2OC1=O)C=C(O)C(O)=C3

InChI Identifier

InChI=1S/C17H10O6/c18-10-3-1-8(2-4-10)15-16-14(23-17(15)21)6-9-5-11(19)12(20)7-13(9)22-16/h1-7,18-20H

InChI Key

QIZCPKIKTOBRLA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanocoumarins. These are polycyclic aromatic compounds containing a furan ring fused to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Furanocoumarins

Direct Parent

Furanocoumarins

Alternative Parents

Substituents

Furanocoumarin
Benzopyran
1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Furan
Heteroaromatic compound
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0035230)
Cell membrane (HMDB: HMDB0035230)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035230)

Source

Exogenous

Exogenous (HMDB: HMDB0035230)

Food

Food (HMDB: HMDB0035230)

Plant (HMDB: HMDB0035230)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0035230)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	320 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	5320 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.043 g/L	ALOGPS
logP	3.05	ALOGPS
logP	2.59	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	7.94	ChemAxon
pKa (Strongest Basic)	-5.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	96.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	82.27 m³·mol⁻¹	ChemAxon
Polarizability	30.54 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	170.0	31661259
DarkChem	[M-H]-	170.404	31661259
DeepCCS	[M+H]+	174.504	30932474
DeepCCS	[M-H]-	172.147	30932474
DeepCCS	[M-2H]-	205.856	30932474
DeepCCS	[M+Na]+	181.083	30932474
AllCCS	[M+H]+	171.6	32859911
AllCCS	[M+H-H2O]+	167.9	32859911
AllCCS	[M+NH4]+	175.0	32859911
AllCCS	[M+Na]+	176.0	32859911
AllCCS	[M-H]-	169.8	32859911
AllCCS	[M+Na-2H]-	168.6	32859911
AllCCS	[M+HCOO]-	167.6	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.62 minutes	32390414
Predicted by Siyang on May 30, 2022	11.1209 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.5 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1507.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	287.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	140.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	283.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	478.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	365.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	211.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	815.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	331.6 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1147.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	273.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	399.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	405.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	171.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Aurantricholide B	OC1=CC=C(C=C1)C1=C2OC3=C(C=C2OC1=O)C=C(O)C(O)=C3	4822.4	Standard polar	33892256
Aurantricholide B	OC1=CC=C(C=C1)C1=C2OC3=C(C=C2OC1=O)C=C(O)C(O)=C3	3075.1	Standard non polar	33892256
Aurantricholide B	OC1=CC=C(C=C1)C1=C2OC3=C(C=C2OC1=O)C=C(O)C(O)=C3	3455.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Aurantricholide B,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=C3OC4=CC(O)=C(O)C=C4C=C3OC2=O)C=C1	3449.5	Semi standard non polar	33892256
Aurantricholide B,1TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(C=C1O)OC1=C(C3=CC=C(O)C=C3)C(=O)OC1=C2	3427.1	Semi standard non polar	33892256
Aurantricholide B,1TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=C3OC(=O)C(C4=CC=C(O)C=C4)=C3O2)C=C1O	3415.0	Semi standard non polar	33892256
Aurantricholide B,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=C3OC4=CC(O[Si](C)(C)C)=C(O)C=C4C=C3OC2=O)C=C1	3459.8	Semi standard non polar	33892256
Aurantricholide B,2TMS,isomer #2	C[Si](C)(C)OC1=CC=C(C2=C3OC4=CC(O)=C(O[Si](C)(C)C)C=C4C=C3OC2=O)C=C1	3437.6	Semi standard non polar	33892256
Aurantricholide B,2TMS,isomer #3	C[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C)OC1=C(C3=CC=C(O)C=C3)C(=O)OC1=C2	3353.0	Semi standard non polar	33892256
Aurantricholide B,3TMS,isomer #1	C[Si](C)(C)OC1=CC=C(C2=C3OC4=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C=C4C=C3OC2=O)C=C1	3317.0	Semi standard non polar	33892256
Aurantricholide B,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C3OC4=CC(O)=C(O)C=C4C=C3OC2=O)C=C1	3699.3	Semi standard non polar	33892256
Aurantricholide B,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O)OC1=C(C3=CC=C(O)C=C3)C(=O)OC1=C2	3680.8	Semi standard non polar	33892256
Aurantricholide B,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C3OC(=O)C(C4=CC=C(O)C=C4)=C3O2)C=C1O	3675.1	Semi standard non polar	33892256
Aurantricholide B,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C3OC4=CC(O[Si](C)(C)C(C)(C)C)=C(O)C=C4C=C3OC2=O)C=C1	3944.7	Semi standard non polar	33892256
Aurantricholide B,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C3OC4=CC(O)=C(O[Si](C)(C)C(C)(C)C)C=C4C=C3OC2=O)C=C1	3918.1	Semi standard non polar	33892256
Aurantricholide B,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OC1=C(C3=CC=C(O)C=C3)C(=O)OC1=C2	3874.5	Semi standard non polar	33892256
Aurantricholide B,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(C2=C3OC4=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C=C4C=C3OC2=O)C=C1	4017.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Aurantricholide B GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-0691000000-0d3d828fa22904a5734a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aurantricholide B GC-MS (3 TMS) - 70eV, Positive	splash10-0ir0-3100920000-02cd9c14d2f9e94de2fb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Aurantricholide B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantricholide B 10V, Positive-QTOF	splash10-03di-0019000000-20b6281c64ca40d02583	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantricholide B 20V, Positive-QTOF	splash10-03di-1059000000-eb373dbfe219eaa9c73d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantricholide B 40V, Positive-QTOF	splash10-0043-2590000000-76022461dcac78d7e895	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantricholide B 10V, Negative-QTOF	splash10-0a4i-0209000000-7626372742e3e4529fc1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantricholide B 20V, Negative-QTOF	splash10-0a4i-0039000000-8ecb34f484202bd831a6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantricholide B 40V, Negative-QTOF	splash10-0ce9-2790000000-bb5df01a380d4be9f835	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantricholide B 10V, Positive-QTOF	splash10-03di-0009000000-28600f1becbfb2f043c7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantricholide B 20V, Positive-QTOF	splash10-03di-0009000000-28600f1becbfb2f043c7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantricholide B 40V, Positive-QTOF	splash10-0a4i-0590000000-9816245439cf553ba601	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantricholide B 10V, Negative-QTOF	splash10-0a4i-0009000000-f9b5f854b100ac09f3d3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantricholide B 20V, Negative-QTOF	splash10-0a4i-0009000000-f9b5f854b100ac09f3d3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Aurantricholide B 40V, Negative-QTOF	splash10-0a4r-1392000000-c4c4058f2870f5c8c78a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

FDB013886

KNApSAcK ID

C00054767

Chemspider ID

9453310

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11278310

PDB ID

Not Available

ChEBI ID

174228

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1848511

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Aurantricholide B (HMDB0035230)

MOL for HMDB0035230 (Aurantricholide B)

3D MOL for HMDB0035230 (Aurantricholide B)

3D SDF for HMDB0035230 (Aurantricholide B)

3D-SDF for HMDB0035230 (Aurantricholide B)

PDB for HMDB0035230 (Aurantricholide B)

3D PDB for HMDB0035230 (Aurantricholide B)

SMILES for HMDB0035230 (Aurantricholide B)

INCHI for HMDB0035230 (Aurantricholide B)

Structure for HMDB0035230 (Aurantricholide B)

3D Structure for HMDB0035230 (Aurantricholide B)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra