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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:07:26 UTC

Update Date

2022-03-07 02:55:55 UTC

HMDB ID

HMDB0038778

Secondary Accession Numbers

HMDB38778

Metabolite Identification

Common Name

Batatasin I

Description

Batatasin I belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached. Batatasin I has been detected, but not quantified in, root vegetables. This could make batatasin I a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Batatasin I.

Structure

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

HMDB0038778
     RDKit          3D
Batatasin I
 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.5136    1.1481   -0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7852   -0.0385   -0.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833   -0.0744   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966   -1.2649   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3103   -1.2645   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7192   -2.4807   -0.2567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3674   -3.7097   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6546   -0.0763   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3483    1.1179    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7062    2.3141    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6521    2.3946    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    1.2111    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7312    1.2322    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885    0.0919    0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8595    0.1513    0.2903 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787    1.3551    0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8878   -1.1089    0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5623   -2.3191    0.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4821   -1.1876   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7435   -0.0459    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203    1.1262   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4255    1.6143    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5700    0.9629   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1206    1.9245   -0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665   -2.1835   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6735   -3.8674   -1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -3.8241    0.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193   -4.5073   -0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2758    3.2344    0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1978    3.3106    0.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1949    2.2201    0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6578    1.1123    0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3830    1.9680   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3105    1.8731    1.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5642   -2.3112    0.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451   -2.1520   -0.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    2.0531   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  9 21  2  0
 21  3  1  0
 20  8  1  0
 20 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
M  END


  Mrv0541 05061310392D          

 21 23  0  0  0  0            999 V2000
    0.7954   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3954   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -0.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5079   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7454   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1579   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2079   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9829   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.2539    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
 10  4  1  0  0  0  0
 10  7  2  0  0  0  0
 11  5  1  0  0  0  0
 11  6  2  0  0  0  0
 12  6  1  0  0  0  0
 12  8  2  0  0  0  0
 13  9  2  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 15  7  1  0  0  0  0
 15 14  2  0  0  0  0
 16  8  1  0  0  0  0
 17 11  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  2  0  0  0  0
 18 14  1  0  0  0  0
 19  1  1  0  0  0  0
 19 12  1  0  0  0  0
 20  2  1  0  0  0  0
 20 15  1  0  0  0  0
 21  3  1  0  0  0  0
 21 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038778

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(OC)=C2C(C=CC3=CC(OC)=C(O)C=C23)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H16O4/c1-19-12-6-11-5-4-10-7-15(20-2)14(18)9-13(10)17(11)16(8-12)21-3/h4-9,18H,1-3H3

> <INCHI_KEY>
KGYHMWVRKYFQQR-UHFFFAOYSA-N

> <FORMULA>
C17H16O4

> <MOLECULAR_WEIGHT>
284.3065

> <EXACT_MASS>
284.104859

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
30.33243023177865

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5,7-trimethoxyphenanthren-3-ol

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
3.1756202106666667

> <ALOGPS_LOGS>
-4.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.682222018133464

> <JCHEM_PKA_STRONGEST_BASIC>
-4.388450771073492

> <JCHEM_POLAR_SURFACE_AREA>
47.92

> <JCHEM_REFRACTIVITY>
80.3289

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
batatasin I

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038778
     RDKit          3D
Batatasin I
 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.5136    1.1481   -0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7852   -0.0385   -0.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833   -0.0744   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966   -1.2649   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3103   -1.2645   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7192   -2.4807   -0.2567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3674   -3.7097   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6546   -0.0763   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3483    1.1179    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7062    2.3141    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6521    2.3946    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    1.2111    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7312    1.2322    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885    0.0919    0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8595    0.1513    0.2903 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787    1.3551    0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8878   -1.1089    0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5623   -2.3191    0.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4821   -1.1876   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7435   -0.0459    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203    1.1262   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4255    1.6143    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5700    0.9629   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1206    1.9245   -0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665   -2.1835   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6735   -3.8674   -1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -3.8241    0.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193   -4.5073   -0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2758    3.2344    0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1978    3.3106    0.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1949    2.2201    0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6578    1.1123    0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3830    1.9680   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3105    1.8731    1.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5642   -2.3112    0.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451   -2.1520   -0.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    2.0531   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  9 21  2  0
 21  3  1  0
 20  8  1  0
 20 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  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       1.485  -2.874   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.805  -0.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.415  -4.207   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.415   1.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.875   1.127   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.565  -0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.725  -0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.565  -2.874   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.185  -2.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.185  -0.206   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.105  -0.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.795  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      10.725  -2.874   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.495  -1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.105  -2.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.495  -4.207   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.255  -1.540   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.035  -1.540   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.875  -4.207   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4    5   10                                                       
CONECT    5    4   11                                                       
CONECT    6   11   12                                                       
CONECT    7   10   15                                                       
CONECT    8   12   16                                                       
CONECT    9   13   14                                                       
CONECT   10    4    7   13                                                  
CONECT   11    5    6   17                                                  
CONECT   12    6    8   19                                                  
CONECT   13    9   10   17                                                  
CONECT   14    9   15   18                                                  
CONECT   15    7   14   20                                                  
CONECT   16    8   17   21                                                  
CONECT   17   11   13   16                                                  
CONECT   18   14                                                            
CONECT   19    1   12                                                       
CONECT   20    2   15                                                       
CONECT   21    3   16                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0038778
HETATM    1  C1  UNL     1      -5.514   1.148  -0.216  1.00  0.00           C  
HETATM    2  O1  UNL     1      -4.785  -0.039  -0.277  1.00  0.00           O  
HETATM    3  C2  UNL     1      -3.383  -0.074  -0.200  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.697  -1.265  -0.264  1.00  0.00           C  
HETATM    5  C4  UNL     1      -1.310  -1.265  -0.185  1.00  0.00           C  
HETATM    6  O2  UNL     1      -0.719  -2.481  -0.257  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.367  -3.710  -0.400  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.655  -0.076  -0.045  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.348   1.118   0.019  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.706   2.314   0.160  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.652   2.395   0.244  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.351   1.211   0.182  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.731   1.232   0.262  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.489   0.092   0.207  1.00  0.00           C  
HETATM   15  O3  UNL     1       4.860   0.151   0.290  1.00  0.00           O  
HETATM   16  C13 UNL     1       5.579   1.355   0.436  1.00  0.00           C  
HETATM   17  C14 UNL     1       2.888  -1.109   0.068  1.00  0.00           C  
HETATM   18  O4  UNL     1       3.562  -2.319   0.002  1.00  0.00           O  
HETATM   19  C15 UNL     1       1.482  -1.188  -0.019  1.00  0.00           C  
HETATM   20  C16 UNL     1       0.744  -0.046   0.038  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.720   1.126  -0.058  1.00  0.00           C  
HETATM   22  H1  UNL     1      -5.426   1.614   0.804  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.570   0.963  -0.425  1.00  0.00           H  
HETATM   24  H3  UNL     1      -5.121   1.924  -0.920  1.00  0.00           H  
HETATM   25  H4  UNL     1      -3.266  -2.183  -0.377  1.00  0.00           H  
HETATM   26  H5  UNL     1      -1.674  -3.867  -1.453  1.00  0.00           H  
HETATM   27  H6  UNL     1      -2.234  -3.824   0.284  1.00  0.00           H  
HETATM   28  H7  UNL     1      -0.619  -4.507  -0.168  1.00  0.00           H  
HETATM   29  H8  UNL     1      -1.276   3.234   0.207  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.198   3.311   0.355  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.195   2.220   0.375  1.00  0.00           H  
HETATM   32  H11 UNL     1       6.658   1.112   0.501  1.00  0.00           H  
HETATM   33  H12 UNL     1       5.383   1.968  -0.455  1.00  0.00           H  
HETATM   34  H13 UNL     1       5.311   1.873   1.389  1.00  0.00           H  
HETATM   35  H14 UNL     1       4.564  -2.311   0.060  1.00  0.00           H  
HETATM   36  H15 UNL     1       1.045  -2.152  -0.127  1.00  0.00           H  
HETATM   37  H16 UNL     1      -3.299   2.053  -0.011  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   25
CONECT    5    6    8    8
CONECT    6    7
CONECT    7   26   27   28
CONECT    8    9   20
CONECT    9   10   21   21
CONECT   10   11   11   29
CONECT   11   12   30
CONECT   12   13   13   20
CONECT   13   14   31
CONECT   14   15   17   17
CONECT   15   16
CONECT   16   32   33   34
CONECT   17   18   19
CONECT   18   35
CONECT   19   20   20   36
CONECT   21   37
END

HMDB0038778
     RDKit          3D
Batatasin I
 37 39  0  0  0  0  0  0  0  0999 V2000
   -5.5136    1.1481   -0.2162 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7852   -0.0385   -0.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3833   -0.0744   -0.2004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966   -1.2649   -0.2643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3103   -1.2645   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7192   -2.4807   -0.2567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3674   -3.7097   -0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6546   -0.0763   -0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3483    1.1179    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7062    2.3141    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6521    2.3946    0.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3506    1.2111    0.1817 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7312    1.2322    0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4885    0.0919    0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8595    0.1513    0.2903 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5787    1.3551    0.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8878   -1.1089    0.0683 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5623   -2.3191    0.0019 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4821   -1.1876   -0.0188 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7435   -0.0459    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7203    1.1262   -0.0584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4255    1.6143    0.8037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5700    0.9629   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1206    1.9245   -0.9201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2665   -2.1835   -0.3766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6735   -3.8674   -1.4525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2339   -3.8241    0.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6193   -4.5073   -0.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2758    3.2344    0.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1978    3.3106    0.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1949    2.2201    0.3746 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6578    1.1123    0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3830    1.9680   -0.4555 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3105    1.8731    1.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5642   -2.3112    0.0599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0451   -2.1520   -0.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2994    2.0531   -0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
  9 21  2  0
 21  3  1  0
 20  8  1  0
 20 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
 10 29  1  0
 11 30  1  0
 13 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
 18 35  1  0
 19 36  1  0
 21 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,5,7-Trimethoxyphenanthren-3-ol	Kegg
2,5,7-Trimethoxy-3-phenanthrenol	HMDB
3-Hydroxy-2,5,7-trimethoxyphenanthrene	HMDB
6-Hydroxy-2,4,7-trimethoxyphenanthrene	HMDB, MeSH
Chikusetsu saponin iva	HMDB

Chemical Formula

C₁₇H₁₆O₄

Average Molecular Weight

284.3065

Monoisotopic Molecular Weight

284.104859

IUPAC Name

2,5,7-trimethoxyphenanthren-3-ol

Traditional Name

batatasin I

CAS Registry Number

51415-00-0

SMILES

COC1=CC(OC)=C2C(C=CC3=CC(OC)=C(O)C=C23)=C1

InChI Identifier

InChI=1S/C17H16O4/c1-19-12-6-11-5-4-10-7-15(20-2)14(18)9-13(10)17(11)16(8-12)21-3/h4-9,18H,1-3H3

InChI Key

KGYHMWVRKYFQQR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrols. Phenanthrols are compounds containing a phenanthrene (or its hydrogenated derivative) to which a hydroxyl group is attached.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Phenanthrols

Direct Parent

Phenanthrols

Alternative Parents

Substituents

Phenanthrol
2-naphthol
Naphthalene
Anisole
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

phenanthrol (CHEBI:2996 )
phenanthrenes (C10246 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038778)
Cell membrane (HMDB: HMDB0038778)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038778)

Source

Exogenous

Exogenous (HMDB: HMDB0038778)

Food

Food (HMDB: HMDB0038778)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Endogenous

Plant

Plant (HMDB: HMDB0038778)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0038778)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	148.5 - 149.6 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.6 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	0.013 g/L	ALOGPS
logP	3.32	ALOGPS
logP	3.18	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.68	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	47.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	80.33 m³·mol⁻¹	ChemAxon
Polarizability	30.33 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]+	167.688	31661259
DarkChem	[M-H]-	170.236	31661259
DeepCCS	[M-2H]-	205.773	30932474
DeepCCS	[M+Na]+	181.192	30932474
AllCCS	[M+H]+	166.1	32859911
AllCCS	[M+H-H2O]+	162.5	32859911
AllCCS	[M+NH4]+	169.5	32859911
AllCCS	[M+Na]+	170.5	32859911
AllCCS	[M-H]-	171.4	32859911
AllCCS	[M+Na-2H]-	170.9	32859911
AllCCS	[M+HCOO]-	170.4	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	15.1952 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.95 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2413.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	394.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	206.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	222.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	276.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	767.4 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	800.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	91.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1211.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	635.8 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	1634.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	483.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	560.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	421.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	338.1 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	16.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Batatasin I	COC1=CC(OC)=C2C(C=CC3=CC(OC)=C(O)C=C23)=C1	4434.8	Standard polar	33892256
Batatasin I	COC1=CC(OC)=C2C(C=CC3=CC(OC)=C(O)C=C23)=C1	2601.5	Standard non polar	33892256
Batatasin I	COC1=CC(OC)=C2C(C=CC3=CC(OC)=C(O)C=C23)=C1	2833.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Batatasin I,1TMS,isomer #1	COC1=CC(OC)=C2C(=C1)C=CC1=CC(OC)=C(O[Si](C)(C)C)C=C12	2753.2	Semi standard non polar	33892256
Batatasin I,1TBDMS,isomer #1	COC1=CC(OC)=C2C(=C1)C=CC1=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C=C12	2947.5	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 - Batatasin I GC-MS (Non-derivatized) - 70eV, Positive	splash10-0le9-0190000000-cabc1e692202bbda6cd7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Batatasin I GC-MS (1 TMS) - 70eV, Positive	splash10-006x-2049000000-640a9db5f0177e652770	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Batatasin I GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Batatasin I 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 - Batatasin I 10V, Positive-QTOF	splash10-000i-0090000000-84b72041a898c4ef022f	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Batatasin I 20V, Positive-QTOF	splash10-000i-0090000000-9b4ff8cc587f2f9b91a2	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Batatasin I 40V, Positive-QTOF	splash10-0fe0-0090000000-d3bc25e072d95b830695	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Batatasin I 10V, Negative-QTOF	splash10-001i-0090000000-3567405bf967eb29df58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Batatasin I 20V, Negative-QTOF	splash10-001i-0090000000-fbfb7624050d6566ef39	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Batatasin I 40V, Negative-QTOF	splash10-000i-0090000000-783515b0d862e6ddd149	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Batatasin I 10V, Negative-QTOF	splash10-001i-0090000000-c5832dccd44e0984ddaa	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Batatasin I 20V, Negative-QTOF	splash10-001i-0090000000-d2620cc2a874137a4126	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Batatasin I 40V, Negative-QTOF	splash10-0udi-0090000000-1dabf1cb8bfc07abd244	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Batatasin I 10V, Positive-QTOF	splash10-000i-0090000000-c8e37af3f9b3dd2352c0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Batatasin I 20V, Positive-QTOF	splash10-000i-0090000000-668ea0bc44f4d1e7c2d1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Batatasin I 40V, Positive-QTOF	splash10-0iml-0190000000-f34b3ad404825ae01369	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442694

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1871251

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 Batatasin I (HMDB0038778)

MOL for HMDB0038778 (Batatasin I)

3D MOL for HMDB0038778 (Batatasin I)

3D SDF for HMDB0038778 (Batatasin I)

3D-SDF for HMDB0038778 (Batatasin I)

PDB for HMDB0038778 (Batatasin I)

3D PDB for HMDB0038778 (Batatasin I)

SMILES for HMDB0038778 (Batatasin I)

INCHI for HMDB0038778 (Batatasin I)

Structure for HMDB0038778 (Batatasin I)

3D Structure for HMDB0038778 (Batatasin I)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra