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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:09 UTC

Update Date

2022-03-07 02:53:06 UTC

HMDB ID

HMDB0031744

Secondary Accession Numbers

HMDB31744

Metabolite Identification

Common Name

Artocarbene

Description

Artocarbene belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids. Based on a literature review a significant number of articles have been published on Artocarbene.

Structure

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

HMDB0031744
     RDKit          3D
Artocarbene
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.6969    2.5907    0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9220    1.0959    0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8197    0.5818    1.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6625    1.0332   -0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1853    0.3555   -1.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173   -0.3563   -1.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747   -1.0830   -2.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0848   -1.1317   -3.7599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1679   -1.7398   -2.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5877   -1.7264   -1.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5637   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926   -2.3676   -0.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0208   -1.2469    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850   -1.4203    1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9898   -0.4075    2.4399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377    0.9014    2.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2437    1.9683    2.8537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2807    1.1267    0.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8754    0.0770   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3449    0.4314   -1.2529 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0283   -0.9982   -0.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -0.3289   -0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136    0.3915    0.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390    2.7695    1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473    2.9623    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6854    3.0662    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4268   -0.2772    1.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5209    1.3840    2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1886    0.2812    2.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6151    1.5328   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288    0.3035   -2.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9348   -0.7283   -4.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208   -2.3042   -3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487   -3.4998   -1.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6066   -3.1731   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7364   -2.4384    2.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.5542    3.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1063    2.9027    2.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1597    2.1655    0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2510    1.3900   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5203   -0.9659    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 10 21  1  0
 21 22  2  0
 22 23  1  0
 23  2  1  0
 22  6  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 21 41  1  0
M  END

  Mrv0541 05061306062D          

 23 25  0  0  0  0            999 V2000
   -0.0980    1.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4323    2.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  2  0  0  0  0
  8  7  2  0  0  0  0
 12  3  1  0  0  0  0
 12  9  2  0  0  0  0
 12 10  1  0  0  0  0
 13  4  1  0  0  0  0
 13  5  1  0  0  0  0
 14  6  1  0  0  0  0
 14 11  2  0  0  0  0
 15  7  1  0  0  0  0
 16 11  1  0  0  0  0
 16 13  2  0  0  0  0
 17  9  1  0  0  0  0
 17 15  2  0  0  0  0
 18 10  2  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  0  0  0  0
 19  2  1  0  0  0  0
 19  8  1  0  0  0  0
 20 14  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  1  0  0  0  0
 23 18  1  0  0  0  0
 23 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031744

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)OC2=CC(\C=C/C3=C(O)C=C(O)C=C3)=CC(O)=C2C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C19H18O4/c1-19(2)8-7-15-17(22)9-12(10-18(15)23-19)3-4-13-5-6-14(20)11-16(13)21/h3-11,20-22H,1-2H3/b4-3-

> <INCHI_KEY>
VPKBRABQIHPIEA-ARJAWSKDSA-N

> <FORMULA>
C19H18O4

> <MOLECULAR_WEIGHT>
310.3438

> <EXACT_MASS>
310.120509064

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.76590129906675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(Z)-2-(5-hydroxy-2,2-dimethyl-2H-chromen-7-yl)ethenyl]benzene-1,3-diol

> <ALOGPS_LOGP>
4.00

> <JCHEM_LOGP>
4.303014288333333

> <ALOGPS_LOGS>
-4.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.492371026230431

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.904262505228886

> <JCHEM_PKA_STRONGEST_BASIC>
-4.916041480693913

> <JCHEM_POLAR_SURFACE_AREA>
69.92

> <JCHEM_REFRACTIVITY>
91.84889999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.86e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(Z)-2-(5-hydroxy-2,2-dimethylchromen-7-yl)ethenyl]benzene-1,3-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0031744
     RDKit          3D
Artocarbene
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.6969    2.5907    0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9220    1.0959    0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8197    0.5818    1.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6625    1.0332   -0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1853    0.3555   -1.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173   -0.3563   -1.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747   -1.0830   -2.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0848   -1.1317   -3.7599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1679   -1.7398   -2.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5877   -1.7264   -1.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5637   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926   -2.3676   -0.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0208   -1.2469    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850   -1.4203    1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9898   -0.4075    2.4399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377    0.9014    2.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2437    1.9683    2.8537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2807    1.1267    0.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8754    0.0770   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3449    0.4314   -1.2529 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0283   -0.9982   -0.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -0.3289   -0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136    0.3915    0.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390    2.7695    1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473    2.9623    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6854    3.0662    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4268   -0.2772    1.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5209    1.3840    2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1886    0.2812    2.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6151    1.5328   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288    0.3035   -2.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9348   -0.7283   -4.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208   -2.3042   -3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487   -3.4998   -1.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6066   -3.1731   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7364   -2.4384    2.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.5542    3.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1063    2.9027    2.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1597    2.1655    0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2510    1.3900   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5203   -0.9659    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 10 21  1  0
 21 22  2  0
 22 23  1  0
 23  2  1  0
 22  6  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 21 41  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      -0.183   3.583   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.807   5.297   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667   9.240   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       8.002   9.240   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   19                                                            
CONECT    3    4   12                                                       
CONECT    4    3   13                                                       
CONECT    5    6   13                                                       
CONECT    6    5   14                                                       
CONECT    7    8   15                                                       
CONECT    8    7   19                                                       
CONECT    9   12   17                                                       
CONECT   10   12   18                                                       
CONECT   11   14   16                                                       
CONECT   12    3    9   10                                                  
CONECT   13    4    5   16                                                  
CONECT   14    6   11   20                                                  
CONECT   15    7   17   18                                                  
CONECT   16   11   13   21                                                  
CONECT   17    9   15   22                                                  
CONECT   18   10   15   23                                                  
CONECT   19    1    2    8   23                                             
CONECT   20   14                                                            
CONECT   21   16                                                            
CONECT   22   17                                                            
CONECT   23   18   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   50    0
END

COMPND    HMDB0031744
HETATM    1  C1  UNL     1      -2.697   2.591   0.958  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.922   1.096   0.691  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.820   0.582   1.813  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.663   1.033  -0.583  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.185   0.356  -1.603  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.917  -0.356  -1.523  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.375  -1.083  -2.570  1.00  0.00           C  
HETATM    8  O1  UNL     1      -2.085  -1.132  -3.760  1.00  0.00           O  
HETATM    9  C8  UNL     1      -0.168  -1.740  -2.443  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.588  -1.726  -1.276  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.749  -2.564  -1.196  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.793  -2.368  -0.476  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.021  -1.247   0.375  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.585  -1.420   1.618  1.00  0.00           C  
HETATM   15  C14 UNL     1       3.990  -0.407   2.440  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.838   0.901   2.028  1.00  0.00           C  
HETATM   17  O2  UNL     1       4.244   1.968   2.854  1.00  0.00           O  
HETATM   18  C16 UNL     1       3.281   1.127   0.793  1.00  0.00           C  
HETATM   19  C17 UNL     1       2.875   0.077  -0.032  1.00  0.00           C  
HETATM   20  O3  UNL     1       2.345   0.431  -1.253  1.00  0.00           O  
HETATM   21  C18 UNL     1       0.028  -0.998  -0.245  1.00  0.00           C  
HETATM   22  C19 UNL     1      -1.187  -0.329  -0.356  1.00  0.00           C  
HETATM   23  O4  UNL     1      -1.714   0.392   0.701  1.00  0.00           O  
HETATM   24  H1  UNL     1      -2.239   2.769   1.931  1.00  0.00           H  
HETATM   25  H2  UNL     1      -2.047   2.962   0.141  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.685   3.066   0.814  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.427  -0.277   1.469  1.00  0.00           H  
HETATM   28  H5  UNL     1      -4.521   1.384   2.125  1.00  0.00           H  
HETATM   29  H6  UNL     1      -3.189   0.281   2.693  1.00  0.00           H  
HETATM   30  H7  UNL     1      -4.615   1.533  -0.734  1.00  0.00           H  
HETATM   31  H8  UNL     1      -3.729   0.303  -2.554  1.00  0.00           H  
HETATM   32  H9  UNL     1      -2.935  -0.728  -4.004  1.00  0.00           H  
HETATM   33  H10 UNL     1       0.221  -2.304  -3.304  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.749  -3.500  -1.834  1.00  0.00           H  
HETATM   35  H12 UNL     1       3.607  -3.173  -0.531  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.736  -2.438   2.010  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.433  -0.554   3.416  1.00  0.00           H  
HETATM   38  H15 UNL     1       4.106   2.903   2.497  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.160   2.165   0.466  1.00  0.00           H  
HETATM   40  H17 UNL     1       2.251   1.390  -1.524  1.00  0.00           H  
HETATM   41  H18 UNL     1       0.520  -0.966   0.700  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   23
CONECT    3   27   28   29
CONECT    4    5    5   30
CONECT    5    6   31
CONECT    6    7    7   22
CONECT    7    8    9
CONECT    8   32
CONECT    9   10   10   33
CONECT   10   11   21
CONECT   11   12   12   34
CONECT   12   13   35
CONECT   13   14   14   19
CONECT   14   15   36
CONECT   15   16   16   37
CONECT   16   17   18
CONECT   17   38
CONECT   18   19   19   39
CONECT   19   20
CONECT   20   40
CONECT   21   22   22   41
CONECT   22   23
END

HMDB0031744
     RDKit          3D
Artocarbene
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.6969    2.5907    0.9578 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9220    1.0959    0.6909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8197    0.5818    1.8131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6625    1.0332   -0.5829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1853    0.3555   -1.6034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9173   -0.3563   -1.5228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3747   -1.0830   -2.5700 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0848   -1.1317   -3.7599 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1679   -1.7398   -2.4426 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5877   -1.7264   -1.2762 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7494   -2.5637   -1.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7926   -2.3676   -0.4762 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0208   -1.2469    0.3752 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5850   -1.4203    1.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9898   -0.4075    2.4399 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8377    0.9014    2.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2437    1.9683    2.8537 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2807    1.1267    0.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8754    0.0770   -0.0318 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3449    0.4314   -1.2529 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0283   -0.9982   -0.2446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -0.3289   -0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7136    0.3915    0.7009 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2390    2.7695    1.9308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473    2.9623    0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6854    3.0662    0.8145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4268   -0.2772    1.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5209    1.3840    2.1251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1886    0.2812    2.6928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6151    1.5328   -0.7336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7288    0.3035   -2.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9348   -0.7283   -4.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2208   -2.3042   -3.3043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7487   -3.4998   -1.8342 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6066   -3.1731   -0.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7364   -2.4384    2.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330   -0.5542    3.4165 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1063    2.9027    2.4965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1597    2.1655    0.4659 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2510    1.3900   -1.5236 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5203   -0.9659    0.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 10 21  1  0
 21 22  2  0
 22 23  1  0
 23  2  1  0
 22  6  1  0
 19 13  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  8 32  1  0
  9 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 15 37  1  0
 17 38  1  0
 18 39  1  0
 20 40  1  0
 21 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
7-(2,4-Dihydroxystyryl)-5-hydroxy-2,2-dimethyl-2H-1-benzopyran	HMDB

Chemical Formula

C₁₉H₁₈O₄

Average Molecular Weight

310.3438

Monoisotopic Molecular Weight

310.120509064

IUPAC Name

4-[(Z)-2-(5-hydroxy-2,2-dimethyl-2H-chromen-7-yl)ethenyl]benzene-1,3-diol

Traditional Name

4-[(Z)-2-(5-hydroxy-2,2-dimethylchromen-7-yl)ethenyl]benzene-1,3-diol

CAS Registry Number

194144-02-0

SMILES

CC1(C)OC2=CC(\C=C/C3=C(O)C=C(O)C=C3)=CC(O)=C2C=C1

InChI Identifier

InChI=1S/C19H18O4/c1-19(2)8-7-15-17(22)9-12(10-18(15)23-19)3-4-13-5-6-14(20)11-16(13)21/h3-11,20-22H,1-2H3/b4-3-

InChI Key

VPKBRABQIHPIEA-ARJAWSKDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbenes. These are organic compounds containing a 1,2-diphenylethylene moiety. Stilbenes (C6-C2-C6 ) are derived from the common phenylpropene (C6-C3) skeleton building block. The introduction of one or more hydroxyl groups to a phenyl ring lead to stilbenoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Not Available

Direct Parent

Stilbenes

Alternative Parents

Substituents

Stilbene
2,2-dimethyl-1-benzopyran
Benzopyran
1-benzopyran
Styrene
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Monocyclic benzene moiety
Benzenoid
Oxacycle
Ether
Organoheterocyclic compound
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0031744)
Cell membrane (HMDB: HMDB0031744)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031744)

Source

Endogenous

Endogenous (HMDB: HMDB0031744)

Plant

Plant (HMDB: HMDB0031744)

Exogenous

Food

Food (HMDB: HMDB0031744)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0031744)

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	3.59 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	0.019 g/L	ALOGPS
logP	4	ALOGPS
logP	4.3	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	8.9	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	69.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	91.85 m³·mol⁻¹	ChemAxon
Polarizability	32.77 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	181.932	30932474
DeepCCS	[M-H]-	179.574	30932474
DeepCCS	[M-2H]-	213.665	30932474
DeepCCS	[M+Na]+	188.893	30932474
AllCCS	[M+H]+	175.6	32859911
AllCCS	[M+H-H2O]+	171.9	32859911
AllCCS	[M+NH4]+	179.0	32859911
AllCCS	[M+Na]+	180.0	32859911
AllCCS	[M-H]-	175.3	32859911
AllCCS	[M+Na-2H]-	174.9	32859911
AllCCS	[M+HCOO]-	174.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artocarbene	CC1(C)OC2=CC(\C=C/C3=C(O)C=C(O)C=C3)=CC(O)=C2C=C1	4143.9	Standard polar	33892256
Artocarbene	CC1(C)OC2=CC(\C=C/C3=C(O)C=C(O)C=C3)=CC(O)=C2C=C1	2890.2	Standard non polar	33892256
Artocarbene	CC1(C)OC2=CC(\C=C/C3=C(O)C=C(O)C=C3)=CC(O)=C2C=C1	3194.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artocarbene,1TMS,isomer #1	CC1(C)C=CC2=C(O)C=C(/C=C\C3=CC=C(O)C=C3O[Si](C)(C)C)C=C2O1	2918.2	Semi standard non polar	33892256
Artocarbene,1TMS,isomer #2	CC1(C)C=CC2=C(O)C=C(/C=C\C3=CC=C(O[Si](C)(C)C)C=C3O)C=C2O1	2904.6	Semi standard non polar	33892256
Artocarbene,1TMS,isomer #3	CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O)C=C3O)C=C2O[Si](C)(C)C)O1	2943.8	Semi standard non polar	33892256
Artocarbene,2TMS,isomer #1	CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O)C=C3O[Si](C)(C)C)C=C2O[Si](C)(C)C)O1	2866.5	Semi standard non polar	33892256
Artocarbene,2TMS,isomer #2	CC1(C)C=CC2=C(O)C=C(/C=C\C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C=C2O1	2848.1	Semi standard non polar	33892256
Artocarbene,2TMS,isomer #3	CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O[Si](C)(C)C)C=C3O)C=C2O[Si](C)(C)C)O1	2848.3	Semi standard non polar	33892256
Artocarbene,3TMS,isomer #1	CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)C=C2O[Si](C)(C)C)O1	2877.6	Semi standard non polar	33892256
Artocarbene,1TBDMS,isomer #1	CC1(C)C=CC2=C(O)C=C(/C=C\C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C=C2O1	3221.7	Semi standard non polar	33892256
Artocarbene,1TBDMS,isomer #2	CC1(C)C=CC2=C(O)C=C(/C=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C=C2O1	3200.4	Semi standard non polar	33892256
Artocarbene,1TBDMS,isomer #3	CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O)C=C3O)C=C2O[Si](C)(C)C(C)(C)C)O1	3257.5	Semi standard non polar	33892256
Artocarbene,2TBDMS,isomer #1	CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)O1	3444.1	Semi standard non polar	33892256
Artocarbene,2TBDMS,isomer #2	CC1(C)C=CC2=C(O)C=C(/C=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C=C2O1	3420.5	Semi standard non polar	33892256
Artocarbene,2TBDMS,isomer #3	CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O)C=C2O[Si](C)(C)C(C)(C)C)O1	3424.9	Semi standard non polar	33892256
Artocarbene,3TBDMS,isomer #1	CC1(C)C=CC2=C(C=C(/C=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)C=C2O[Si](C)(C)C(C)(C)C)O1	3652.3	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 - Artocarbene GC-MS (Non-derivatized) - 70eV, Positive	splash10-01pn-0291000000-fec585b94f70aed3bc28	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artocarbene GC-MS (3 TMS) - 70eV, Positive	splash10-0ik9-1004590000-32fc410853eab601e92f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artocarbene 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 - Artocarbene 10V, Positive-QTOF	splash10-03di-0029000000-47594a3184680821d581	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarbene 20V, Positive-QTOF	splash10-03di-1294000000-c4e865644b22b20c5c91	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarbene 40V, Positive-QTOF	splash10-0rki-4590000000-1db94ce0baddec135a46	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarbene 10V, Negative-QTOF	splash10-0a4i-0019000000-addcc9a5916d8529dd1b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarbene 20V, Negative-QTOF	splash10-0a4i-0169000000-fbc33dc71f03101f4ba9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarbene 40V, Negative-QTOF	splash10-0a6r-1690000000-123738ebbc562d562077	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarbene 10V, Positive-QTOF	splash10-03di-0019000000-f93d01a5595bb135c374	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarbene 20V, Positive-QTOF	splash10-03yi-0193000000-bafc978f9cddbc157c43	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarbene 40V, Positive-QTOF	splash10-0gb9-0290000000-d796470d38c60873f612	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarbene 10V, Negative-QTOF	splash10-0a4i-0009000000-a5477ba8add3d375c008	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarbene 20V, Negative-QTOF	splash10-0a4i-1049000000-4a9280f76345399d14a4	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artocarbene 40V, Negative-QTOF	splash10-03dr-0190000000-df70e97dedf508bdefb0	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

FDB008413

KNApSAcK ID

C00054483

Chemspider ID

30776916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751188

PDB ID

Not Available

ChEBI ID

174233

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1827681

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 Artocarbene (HMDB0031744)

MOL for HMDB0031744 (Artocarbene)

3D MOL for HMDB0031744 (Artocarbene)

3D SDF for HMDB0031744 (Artocarbene)

3D-SDF for HMDB0031744 (Artocarbene)

PDB for HMDB0031744 (Artocarbene)

3D PDB for HMDB0031744 (Artocarbene)

SMILES for HMDB0031744 (Artocarbene)

INCHI for HMDB0031744 (Artocarbene)

Structure for HMDB0031744 (Artocarbene)

3D Structure for HMDB0031744 (Artocarbene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra