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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:31:29 UTC

Update Date

2022-03-07 02:56:05 UTC

HMDB ID

HMDB0039156

Secondary Accession Numbers

HMDB39156

Metabolite Identification

Common Name

3beta-Hydroxycinnamolide

Description

3beta-Hydroxycinnamolide belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 3beta-Hydroxycinnamolide 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 3beta-hydroxycinnamolide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3beta-Hydroxycinnamolide.

Structure

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

HMDB0039156
     RDKit          3D
3beta-Hydroxycinnamolide
 40 42  0  0  0  0  0  0  0  0999 V2000
   -2.5247   -1.5388    0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268   -0.5612   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728   -1.0963   -1.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411    0.7663   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8909    0.9934    0.9432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3424    1.9365   -0.5223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054    1.5553   -0.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    0.6671    0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4865    1.5768    1.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9760    0.3576    0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6608    1.2045   -0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446    0.5455   -0.7831 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -0.8100   -0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2391   -1.7596   -1.4071 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078   -0.9814   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -1.9832    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758   -1.8281    0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618   -0.4800    0.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5734   -1.2124    0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4301   -2.5410   -0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149   -1.7089    1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4557   -0.3835   -2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7693   -2.0230   -1.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1166   -1.4099   -1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464    0.6972   -1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483    0.2294    1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4397    2.7340    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    2.3992   -1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062    2.4859   -0.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2557    1.1077   -1.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3043    1.2388    2.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7123    2.6306    1.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5077    1.4738    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6136    0.5234    1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2713    1.0610   -1.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7775    2.2543   -0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109   -2.9573   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4847   -2.1699    1.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4402   -2.6189    0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860   -0.3749    1.7573 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  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  8  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
M  END


  Mrv0541 05061310532D          

 18 20  0  0  0  0            999 V2000
    0.4930    1.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4416    1.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9291   -0.3403    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4083    1.7892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5837    1.8150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2799   -0.2887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1045   -0.3145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8963   -0.2691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7983    1.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3637    0.3610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491    1.1137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1101    0.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5995    0.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3245    1.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5391    0.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9347    0.4640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2295    1.3982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601    0.0428    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  9  4  2  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  9  1  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  3  1  0  0  0  0
 15  7  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 16 12  1  0  0  0  0
 17 13  2  0  0  0  0
 18  8  1  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039156

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)C(O)CCC2(C)C3COC(=O)C3=CCC12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O3/c1-14(2)11-5-4-9-10(8-18-13(9)17)15(11,3)7-6-12(14)16/h4,10-12,16H,5-8H2,1-3H3

> <INCHI_KEY>
BXRHNOVSIVSFJG-UHFFFAOYSA-N

> <FORMULA>
C15H22O3

> <MOLECULAR_WEIGHT>
250.3334

> <EXACT_MASS>
250.15689457

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.47357860524702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-3-one

> <ALOGPS_LOGP>
3.08

> <JCHEM_LOGP>
2.2223947609999994

> <ALOGPS_LOGS>
-2.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.55417804443019

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8068021470996082

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
69.14120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.63e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-hydroxy-6,6,9a-trimethyl-1H,5H,5aH,7H,8H,9H,9bH-naphtho[1,2-c]furan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039156
     RDKit          3D
3beta-Hydroxycinnamolide
 40 42  0  0  0  0  0  0  0  0999 V2000
   -2.5247   -1.5388    0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268   -0.5612   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728   -1.0963   -1.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411    0.7663   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8909    0.9934    0.9432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3424    1.9365   -0.5223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054    1.5553   -0.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    0.6671    0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4865    1.5768    1.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9760    0.3576    0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6608    1.2045   -0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446    0.5455   -0.7831 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -0.8100   -0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2391   -1.7596   -1.4071 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078   -0.9814   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -1.9832    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758   -1.8281    0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618   -0.4800    0.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5734   -1.2124    0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4301   -2.5410   -0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149   -1.7089    1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4557   -0.3835   -2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7693   -2.0230   -1.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1166   -1.4099   -1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464    0.6972   -1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483    0.2294    1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4397    2.7340    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    2.3992   -1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062    2.4859   -0.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2557    1.1077   -1.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3043    1.2388    2.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7123    2.6306    1.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5077    1.4738    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6136    0.5234    1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2713    1.0610   -1.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7775    2.2543   -0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109   -2.9573   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4847   -2.1699    1.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4402   -2.6189    0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860   -0.3749    1.7573 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  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  8  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  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       0.920   3.635   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.824   2.699   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.601  -0.635   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.495   3.340   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.956   3.388   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.522  -0.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.062  -0.587   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.406  -0.502   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.223   1.983   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.412   0.674   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.145   2.079   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.206   0.818   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.719   1.616   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.606   2.127   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.873   0.722   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.745   0.866   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       7.895   2.610   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       6.832   0.080   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   15                                                            
CONECT    4    5    9                                                       
CONECT    5    4   11                                                       
CONECT    6    7   12                                                       
CONECT    7    6   15                                                       
CONECT    8   10   18                                                       
CONECT    9    4   10   13                                                  
CONECT   10    8    9   15                                                  
CONECT   11    5   14   15                                                  
CONECT   12    6   14   16                                                  
CONECT   13    9   17   18                                                  
CONECT   14    1    2   11   12                                             
CONECT   15    3    7   10   11                                             
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18    8   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0039156
HETATM    1  C1  UNL     1      -2.525  -1.539   0.426  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.527  -0.561  -0.217  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.173  -1.096  -1.558  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.241   0.766  -0.260  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.891   0.993   0.943  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.342   1.937  -0.522  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.105   1.555  -0.635  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.555   0.667   0.523  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.486   1.577   1.742  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.976   0.358   0.298  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.661   1.205  -0.763  1.00  0.00           C  
HETATM   12  O2  UNL     1       3.945   0.546  -0.783  1.00  0.00           O  
HETATM   13  C11 UNL     1       3.614  -0.810  -0.868  1.00  0.00           C  
HETATM   14  O3  UNL     1       4.239  -1.760  -1.407  1.00  0.00           O  
HETATM   15  C12 UNL     1       2.308  -0.981  -0.171  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.523  -1.983   0.060  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.276  -1.828   0.798  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.362  -0.480   0.756  1.00  0.00           C  
HETATM   19  H1  UNL     1      -3.573  -1.212   0.221  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.430  -2.541  -0.078  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.315  -1.709   1.482  1.00  0.00           H  
HETATM   22  H4  UNL     1      -1.456  -0.383  -2.386  1.00  0.00           H  
HETATM   23  H5  UNL     1      -1.769  -2.023  -1.808  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.117  -1.410  -1.684  1.00  0.00           H  
HETATM   25  H7  UNL     1      -3.046   0.697  -1.040  1.00  0.00           H  
HETATM   26  H8  UNL     1      -2.948   0.229   1.533  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.440   2.734   0.252  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.636   2.399  -1.487  1.00  0.00           H  
HETATM   29  H11 UNL     1       0.706   2.486  -0.591  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.256   1.108  -1.612  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.304   1.239   2.439  1.00  0.00           H  
HETATM   32  H14 UNL     1       0.712   2.631   1.469  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.508   1.474   2.213  1.00  0.00           H  
HETATM   34  H16 UNL     1       2.614   0.523   1.223  1.00  0.00           H  
HETATM   35  H17 UNL     1       2.271   1.061  -1.773  1.00  0.00           H  
HETATM   36  H18 UNL     1       2.777   2.254  -0.462  1.00  0.00           H  
HETATM   37  H19 UNL     1       1.811  -2.957  -0.307  1.00  0.00           H  
HETATM   38  H20 UNL     1       0.485  -2.170   1.856  1.00  0.00           H  
HETATM   39  H21 UNL     1      -0.440  -2.619   0.422  1.00  0.00           H  
HETATM   40  H22 UNL     1      -0.886  -0.375   1.757  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    4   18
CONECT    3   22   23   24
CONECT    4    5    6   25
CONECT    5   26
CONECT    6    7   27   28
CONECT    7    8   29   30
CONECT    8    9   10   18
CONECT    9   31   32   33
CONECT   10   11   15   34
CONECT   11   12   35   36
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16   16
CONECT   16   17   37
CONECT   17   18   38   39
CONECT   18   40
END

HMDB0039156
     RDKit          3D
3beta-Hydroxycinnamolide
 40 42  0  0  0  0  0  0  0  0999 V2000
   -2.5247   -1.5388    0.4256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5268   -0.5612   -0.2173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1728   -1.0963   -1.5575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2411    0.7663   -0.2601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8909    0.9934    0.9432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3424    1.9365   -0.5223 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1054    1.5553   -0.6354 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5546    0.6671    0.5227 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4865    1.5768    1.7423 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9760    0.3576    0.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6608    1.2045   -0.7631 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9446    0.5455   -0.7831 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6140   -0.8100   -0.8681 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2391   -1.7596   -1.4071 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3078   -0.9814   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5235   -1.9832    0.0604 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2758   -1.8281    0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3618   -0.4800    0.7565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5734   -1.2124    0.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4301   -2.5410   -0.0783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3149   -1.7089    1.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4557   -0.3835   -2.3857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7693   -2.0230   -1.8083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1166   -1.4099   -1.6844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0464    0.6972   -1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9483    0.2294    1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4397    2.7340    0.2524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6358    2.3992   -1.4870 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7062    2.4859   -0.5907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2557    1.1077   -1.6119 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3043    1.2388    2.4389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7123    2.6306    1.4687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5077    1.4738    2.2125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6136    0.5234    1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2713    1.0610   -1.7729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7775    2.2543   -0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8109   -2.9573   -0.3073 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4847   -2.1699    1.8562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4402   -2.6189    0.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8860   -0.3749    1.7573 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  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 18  8  1  0
 15 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  9 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 16 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3b-Hydroxycinnamolide	Generator
3Β-hydroxycinnamolide	Generator
3beta-Hydroxycinnamolide	MeSH
3-Hydroxycinnamolide	MeSH

Chemical Formula

C₁₅H₂₂O₃

Average Molecular Weight

250.3334

Monoisotopic Molecular Weight

250.15689457

IUPAC Name

7-hydroxy-6,6,9a-trimethyl-1H,3H,5H,5aH,6H,7H,8H,9H,9aH,9bH-naphtho[1,2-c]furan-3-one

Traditional Name

7-hydroxy-6,6,9a-trimethyl-1H,5H,5aH,7H,8H,9H,9bH-naphtho[1,2-c]furan-3-one

CAS Registry Number

Not Available

SMILES

CC1(C)C(O)CCC2(C)C3COC(=O)C3=CCC12

InChI Identifier

InChI=1S/C15H22O3/c1-14(2)11-5-4-9-10(8-18-13(9)17)15(11,3)7-6-12(14)16/h4,10-12,16H,5-8H2,1-3H3

InChI Key

BXRHNOVSIVSFJG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Gamma butyrolactone
Cyclic alcohol
Tetrahydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Lactone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039156)

Source

Endogenous

Endogenous (HMDB: HMDB0039156)

Plant

Plant (HMDB: HMDB0039156)

Exogenous

Food

Food (HMDB: HMDB0039156)

Vegetable

Mushroom

Exogenous (HMDB: HMDB0039156)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0039156)

Role

Biological role

Energy source (HMDB: HMDB0039156)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039156)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	164.5 - 167 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.46 g/L	ALOGPS
logP	3.08	ALOGPS
logP	2.22	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.14 m³·mol⁻¹	ChemAxon
Polarizability	27.47 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
DarkChem	[M+H]+	158.163	31661259
DarkChem	[M-H]-	156.77	31661259
DeepCCS	[M-2H]-	194.335	30932474
DeepCCS	[M+Na]+	169.9	30932474
AllCCS	[M+H]+	159.0	32859911
AllCCS	[M+H-H2O]+	155.4	32859911
AllCCS	[M+NH4]+	162.4	32859911
AllCCS	[M+Na]+	163.3	32859911
AllCCS	[M-H]-	165.3	32859911
AllCCS	[M+Na-2H]-	165.4	32859911
AllCCS	[M+HCOO]-	165.6	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.	6.35 minutes	32390414
Predicted by Siyang on May 30, 2022	13.2285 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.17 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2232.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	336.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	164.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	172.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	139.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	505.7 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	632.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	71.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	995.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	418.8 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	1384.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	368.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	401.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	296.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	319.2 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	42.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3beta-Hydroxycinnamolide	CC1(C)C(O)CCC2(C)C3COC(=O)C3=CCC12	3011.3	Standard polar	33892256
3beta-Hydroxycinnamolide	CC1(C)C(O)CCC2(C)C3COC(=O)C3=CCC12	2078.9	Standard non polar	33892256
3beta-Hydroxycinnamolide	CC1(C)C(O)CCC2(C)C3COC(=O)C3=CCC12	2362.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3beta-Hydroxycinnamolide,1TMS,isomer #1	CC1(C)C(O[Si](C)(C)C)CCC2(C)C3COC(=O)C3=CCC12	2247.3	Semi standard non polar	33892256
3beta-Hydroxycinnamolide,1TBDMS,isomer #1	CC1(C)C(O[Si](C)(C)C(C)(C)C)CCC2(C)C3COC(=O)C3=CCC12	2494.1	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 - 3beta-Hydroxycinnamolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-05a9-2890000000-4fdc935f82f82bb03545	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3beta-Hydroxycinnamolide GC-MS (1 TMS) - 70eV, Positive	splash10-05bg-2392000000-aace8d561f9f03035aa9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3beta-Hydroxycinnamolide 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 - 3beta-Hydroxycinnamolide 10V, Positive-QTOF	splash10-0f89-0190000000-e16bf78a993601a3236d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Hydroxycinnamolide 20V, Positive-QTOF	splash10-0f89-0790000000-939ca0eea69845d34457	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Hydroxycinnamolide 40V, Positive-QTOF	splash10-014l-7900000000-ccc2432e0f3d2abc28f0	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Hydroxycinnamolide 10V, Negative-QTOF	splash10-0002-0090000000-7d91d7beb7d11887e8ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Hydroxycinnamolide 20V, Negative-QTOF	splash10-0532-0090000000-44ba4cf144e19f0e6b2f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Hydroxycinnamolide 40V, Negative-QTOF	splash10-0fri-3790000000-edb09f163e297261a887	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Hydroxycinnamolide 10V, Negative-QTOF	splash10-0002-0090000000-0dd1e5565d33dd37f20a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Hydroxycinnamolide 20V, Negative-QTOF	splash10-0002-0090000000-ea5326908444afaa0c01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Hydroxycinnamolide 40V, Negative-QTOF	splash10-0002-0190000000-d7a7297110cd53a1f6be	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Hydroxycinnamolide 10V, Positive-QTOF	splash10-0udi-0090000000-9f35b296e2acad4b97c0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Hydroxycinnamolide 20V, Positive-QTOF	splash10-0uei-0960000000-418d0805ca06774bc82a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Hydroxycinnamolide 40V, Positive-QTOF	splash10-014i-7920000000-09468490141130f6487a	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

FDB018676

KNApSAcK ID

C00020295

Chemspider ID

35014755

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14433053

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for 3beta-Hydroxycinnamolide (HMDB0039156)

MOL for HMDB0039156 (3beta-Hydroxycinnamolide)

3D MOL for HMDB0039156 (3beta-Hydroxycinnamolide)

3D SDF for HMDB0039156 (3beta-Hydroxycinnamolide)

3D-SDF for HMDB0039156 (3beta-Hydroxycinnamolide)

PDB for HMDB0039156 (3beta-Hydroxycinnamolide)

3D PDB for HMDB0039156 (3beta-Hydroxycinnamolide)

SMILES for HMDB0039156 (3beta-Hydroxycinnamolide)

INCHI for HMDB0039156 (3beta-Hydroxycinnamolide)

Structure for HMDB0039156 (3beta-Hydroxycinnamolide)

3D Structure for HMDB0039156 (3beta-Hydroxycinnamolide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra