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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:57:47 UTC

Update Date

2022-03-07 02:55:51 UTC

HMDB ID

HMDB0038629

Secondary Accession Numbers

HMDB38629

Metabolite Identification

Common Name

Litebamine

Description

Litebamine 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. Litebamine is a very strong basic compound (based on its pKa). Outside of the human body, litebamine has been detected, but not quantified in, fruits. This could make litebamine a potential biomarker for the consumption of these foods.

Structure

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

HMDB0038629
     RDKit          3D
Litebamine
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.2097   -1.1261   -1.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2759   -0.0576   -0.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1723    0.5491    0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844    0.0761   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075    0.6769    0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9369    1.7442    1.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8698    2.3956    1.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795    1.9843    1.5266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831    0.9370    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    0.5286    0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0536   -0.5120   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9825   -1.1774   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058   -2.2335   -1.9780 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -0.7754   -0.7651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2795   -1.5470   -1.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5009   -2.8119   -0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5089    0.2673    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4161   -0.9713   -0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4007    0.0350   -0.6246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7249   -0.4130   -0.8877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770    0.5475    0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861    1.2536    0.9445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236    2.1821    1.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    1.5922    1.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5913    2.0654    1.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6230   -1.9360   -0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2240   -1.5013   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7379   -0.8053   -2.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -0.6943   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312    3.2031    2.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2787    2.4783    1.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0792   -2.5855   -2.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5198   -2.5962    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6790   -3.4741   -0.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772   -3.2219   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5881   -1.9500   -0.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911   -1.0632   -2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4492    0.1595   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0348   -0.2058   -1.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8893   -1.4892   -0.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4796   -0.2041    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0944    1.3150    0.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417    1.2361    2.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9927    2.2733    0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2907    3.0164    2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    2.8357    2.0392 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 17  5  1  0
 17  9  1  0
 22 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 25 46  1  0
M  END


  Mrv0541 05061310332D          

 25 28  0  0  0  0            999 V2000
    8.2588   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477   -2.8518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782   -3.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9381    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482    0.2664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3685   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1786   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5878   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1279   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9086   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0182   -0.5132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6680   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0984   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0477   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3178   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4782   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5583   -2.0723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7482   -1.9164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4486   -0.9809    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2376   -0.5132    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8284   -2.8518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7777   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2081   -2.5400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  7  6  1  0  0  0  0
 11  4  1  0  0  0  0
 11  8  2  0  0  0  0
 12  6  1  0  0  0  0
 13  5  1  0  0  0  0
 13 12  2  0  0  0  0
 14  9  2  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 17 16  2  0  0  0  0
 18 13  1  0  0  0  0
 18 14  1  0  0  0  0
 19 15  2  0  0  0  0
 20 18  2  0  0  0  0
 20 19  1  0  0  0  0
 21  1  1  0  0  0  0
 21  7  1  0  0  0  0
 21 10  1  0  0  0  0
 22 16  1  0  0  0  0
 23 19  1  0  0  0  0
 24  2  1  0  0  0  0
 24 17  1  0  0  0  0
 25  3  1  0  0  0  0
 25 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038629

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=C2C=CC3=C4CCN(C)CC4=C(O)C(OC)=C3C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H21NO4/c1-21-7-6-12-13-5-4-11-8-16(22)17(24-2)9-14(11)18(13)20(25-3)19(23)15(12)10-21/h4-5,8-9,22-23H,6-7,10H2,1-3H3

> <INCHI_KEY>
QOWFEPGZJDCIKG-UHFFFAOYSA-N

> <FORMULA>
C20H21NO4

> <MOLECULAR_WEIGHT>
339.385

> <EXACT_MASS>
339.147058165

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
36.926689401350735

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9,13-dimethoxy-5-methyl-5-azatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1,7,9,11,13,15,17-heptaene-8,14-diol

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
2.806824756684445

> <ALOGPS_LOGS>
-3.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
9.811700591417347

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.98829515483833

> <JCHEM_PKA_STRONGEST_BASIC>
7.457172527070641

> <JCHEM_POLAR_SURFACE_AREA>
62.16000000000001

> <JCHEM_REFRACTIVITY>
97.69889999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9,13-dimethoxy-5-methyl-5-azatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1,7,9,11,13,15,17-heptaene-8,14-diol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038629
     RDKit          3D
Litebamine
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.2097   -1.1261   -1.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2759   -0.0576   -0.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1723    0.5491    0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844    0.0761   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075    0.6769    0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9369    1.7442    1.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8698    2.3956    1.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795    1.9843    1.5266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831    0.9370    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    0.5286    0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0536   -0.5120   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9825   -1.1774   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058   -2.2335   -1.9780 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -0.7754   -0.7651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2795   -1.5470   -1.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5009   -2.8119   -0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5089    0.2673    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4161   -0.9713   -0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4007    0.0350   -0.6246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7249   -0.4130   -0.8877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770    0.5475    0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861    1.2536    0.9445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236    2.1821    1.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    1.5922    1.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5913    2.0654    1.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6230   -1.9360   -0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2240   -1.5013   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7379   -0.8053   -2.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -0.6943   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312    3.2031    2.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2787    2.4783    1.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0792   -2.5855   -2.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5198   -2.5962    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6790   -3.4741   -0.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772   -3.2219   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5881   -1.9500   -0.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911   -1.0632   -2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4492    0.1595   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0348   -0.2058   -1.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8893   -1.4892   -0.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4796   -0.2041    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0944    1.3150    0.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417    1.2361    2.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9927    2.2733    0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2907    3.0164    2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    2.8357    2.0392 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 17  5  1  0
 17  9  1  0
 22 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 25 46  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      15.416  -2.122   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.822  -5.323   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.359  -6.197   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.351   0.788   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.863   0.497   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.888  -0.085   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.400  -0.376   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.831  -0.085   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.839  -2.995   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.896  -2.995   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.343  -0.376   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.880  -1.249   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.367  -0.958   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.847  -1.831   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.384  -2.704   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.822  -1.249   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.327  -2.704   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.359  -2.122   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.375  -3.868   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.863  -3.577   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      13.904  -1.831   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0       2.310  -0.958   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      10.880  -5.323   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       3.318  -3.868   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       7.855  -4.741   0.000  0.00  0.00           O+0
CONECT    1   21                                                            
CONECT    2   24                                                            
CONECT    3   25                                                            
CONECT    4    5   11                                                       
CONECT    5    4   13                                                       
CONECT    6    7   12                                                       
CONECT    7    6   21                                                       
CONECT    8   11   16                                                       
CONECT    9   14   17                                                       
CONECT   10   15   21                                                       
CONECT   11    4    8   14                                                  
CONECT   12    6   13   15                                                  
CONECT   13    5   12   18                                                  
CONECT   14    9   11   18                                                  
CONECT   15   10   12   19                                                  
CONECT   16    8   17   22                                                  
CONECT   17    9   16   24                                                  
CONECT   18   13   14   20                                                  
CONECT   19   15   20   23                                                  
CONECT   20   18   19   25                                                  
CONECT   21    1    7   10                                                  
CONECT   22   16                                                            
CONECT   23   19                                                            
CONECT   24    2   17                                                       
CONECT   25    3   20                                                       
MASTER        0    0    0    0    0    0    0    0   25    0   56    0
END

COMPND    HMDB0038629
HETATM    1  C1  UNL     1       5.210  -1.126  -1.275  1.00  0.00           C  
HETATM    2  O1  UNL     1       5.276  -0.058  -0.379  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.172   0.549   0.187  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.884   0.076  -0.148  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.807   0.677   0.415  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.937   1.744   1.303  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.870   2.396   1.856  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.379   1.984   1.527  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.583   0.937   0.660  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.850   0.529   0.322  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.054  -0.512  -0.547  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.983  -1.177  -1.100  1.00  0.00           C  
HETATM   13  O2  UNL     1      -1.206  -2.234  -1.978  1.00  0.00           O  
HETATM   14  C12 UNL     1       0.320  -0.775  -0.765  1.00  0.00           C  
HETATM   15  O3  UNL     1       1.280  -1.547  -1.388  1.00  0.00           O  
HETATM   16  C13 UNL     1       1.501  -2.812  -0.662  1.00  0.00           C  
HETATM   17  C14 UNL     1       0.509   0.267   0.095  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.416  -0.971  -0.946  1.00  0.00           C  
HETATM   19  N1  UNL     1      -4.401   0.035  -0.625  1.00  0.00           N  
HETATM   20  C16 UNL     1      -5.725  -0.413  -0.888  1.00  0.00           C  
HETATM   21  C17 UNL     1      -4.277   0.548   0.697  1.00  0.00           C  
HETATM   22  C18 UNL     1      -2.986   1.254   0.944  1.00  0.00           C  
HETATM   23  C19 UNL     1       3.224   2.182   1.608  1.00  0.00           C  
HETATM   24  C20 UNL     1       4.316   1.592   1.058  1.00  0.00           C  
HETATM   25  O4  UNL     1       5.591   2.065   1.394  1.00  0.00           O  
HETATM   26  H1  UNL     1       4.623  -1.936  -0.791  1.00  0.00           H  
HETATM   27  H2  UNL     1       6.224  -1.501  -1.486  1.00  0.00           H  
HETATM   28  H3  UNL     1       4.738  -0.805  -2.242  1.00  0.00           H  
HETATM   29  H4  UNL     1       2.834  -0.694  -0.859  1.00  0.00           H  
HETATM   30  H5  UNL     1       1.031   3.203   2.527  1.00  0.00           H  
HETATM   31  H6  UNL     1      -1.279   2.478   1.939  1.00  0.00           H  
HETATM   32  H7  UNL     1      -2.079  -2.586  -2.267  1.00  0.00           H  
HETATM   33  H8  UNL     1       1.520  -2.596   0.426  1.00  0.00           H  
HETATM   34  H9  UNL     1       0.679  -3.474  -0.933  1.00  0.00           H  
HETATM   35  H10 UNL     1       2.477  -3.222  -0.942  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.588  -1.950  -0.488  1.00  0.00           H  
HETATM   37  H12 UNL     1      -3.391  -1.063  -2.058  1.00  0.00           H  
HETATM   38  H13 UNL     1      -6.449   0.160  -0.246  1.00  0.00           H  
HETATM   39  H14 UNL     1      -6.035  -0.206  -1.930  1.00  0.00           H  
HETATM   40  H15 UNL     1      -5.889  -1.489  -0.608  1.00  0.00           H  
HETATM   41  H16 UNL     1      -4.480  -0.204   1.491  1.00  0.00           H  
HETATM   42  H17 UNL     1      -5.094   1.315   0.824  1.00  0.00           H  
HETATM   43  H18 UNL     1      -2.842   1.236   2.062  1.00  0.00           H  
HETATM   44  H19 UNL     1      -2.993   2.273   0.553  1.00  0.00           H  
HETATM   45  H20 UNL     1       3.291   3.016   2.306  1.00  0.00           H  
HETATM   46  H21 UNL     1       5.665   2.836   2.039  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3
CONECT    3    4    4   24
CONECT    4    5   29
CONECT    5    6    6   17
CONECT    6    7   23
CONECT    7    8    8   30
CONECT    8    9   31
CONECT    9   10   10   17
CONECT   10   11   22
CONECT   11   12   12   18
CONECT   12   13   14
CONECT   13   32
CONECT   14   15   17   17
CONECT   15   16
CONECT   16   33   34   35
CONECT   18   19   36   37
CONECT   19   20   21
CONECT   20   38   39   40
CONECT   21   22   41   42
CONECT   22   43   44
CONECT   23   24   24   45
CONECT   24   25
CONECT   25   46
END

HMDB0038629
     RDKit          3D
Litebamine
 46 49  0  0  0  0  0  0  0  0999 V2000
    5.2097   -1.1261   -1.2749 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2759   -0.0576   -0.3786 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1723    0.5491    0.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844    0.0761   -0.1478 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8075    0.6769    0.4145 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9369    1.7442    1.3031 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8698    2.3956    1.8565 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3795    1.9843    1.5266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5831    0.9370    0.6605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8500    0.5286    0.3223 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0536   -0.5120   -0.5466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9825   -1.1774   -1.0999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2058   -2.2335   -1.9780 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3196   -0.7754   -0.7651 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2795   -1.5470   -1.3884 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5009   -2.8119   -0.6616 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5089    0.2673    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4161   -0.9713   -0.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4007    0.0350   -0.6246 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7249   -0.4130   -0.8877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2770    0.5475    0.6968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9861    1.2536    0.9445 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236    2.1821    1.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3156    1.5922    1.0579 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5913    2.0654    1.3942 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6230   -1.9360   -0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2240   -1.5013   -1.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7379   -0.8053   -2.2420 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8339   -0.6943   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312    3.2031    2.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2787    2.4783    1.9393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0792   -2.5855   -2.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5198   -2.5962    0.4259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6790   -3.4741   -0.9334 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4772   -3.2219   -0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5881   -1.9500   -0.4878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3911   -1.0632   -2.0584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4492    0.1595   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0348   -0.2058   -1.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8893   -1.4892   -0.6077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4796   -0.2041    1.4908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0944    1.3150    0.8242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8417    1.2361    2.0624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9927    2.2733    0.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2907    3.0164    2.3056 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6655    2.8357    2.0392 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 11 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  6 23  1  0
 23 24  2  0
 24 25  1  0
 24  3  1  0
 17  5  1  0
 17  9  1  0
 22 10  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  7 30  1  0
  8 31  1  0
 13 32  1  0
 16 33  1  0
 16 34  1  0
 16 35  1  0
 18 36  1  0
 18 37  1  0
 20 38  1  0
 20 39  1  0
 20 40  1  0
 21 41  1  0
 21 42  1  0
 22 43  1  0
 22 44  1  0
 23 45  1  0
 25 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,3,4-Tetrahydro-9,11-dimethoxy-2-methylnaphth[2,1-F]isoquinoline-8,12-diol, 9ci	HMDB
Litebamine	MeSH

Chemical Formula

C₂₀H₂₁NO₄

Average Molecular Weight

339.385

Monoisotopic Molecular Weight

339.147058165

IUPAC Name

9,13-dimethoxy-5-methyl-5-azatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1,7,9,11,13,15,17-heptaene-8,14-diol

Traditional Name

9,13-dimethoxy-5-methyl-5-azatetracyclo[8.8.0.0²,⁷.0¹¹,¹⁶]octadeca-1,7,9,11,13,15,17-heptaene-8,14-diol

CAS Registry Number

137031-56-2

SMILES

COC1=C(O)C=C2C=CC3=C4CCN(C)CC4=C(O)C(OC)=C3C2=C1

InChI Identifier

InChI=1S/C20H21NO4/c1-21-7-6-12-13-5-4-11-8-16(22)17(24-2)9-14(11)18(13)20(25-3)19(23)15(12)10-21/h4-5,8-9,22-23H,6-7,10H2,1-3H3

InChI Key

QOWFEPGZJDCIKG-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
Tetrahydroisoquinoline
Anisole
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Tertiary amine
Tertiary aliphatic amine
Azacycle
Ether
Organoheterocyclic compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038629)

Cellular substructure

Membrane (HMDB: HMDB0038629)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038629)

Source

Exogenous

Food

Food (HMDB: HMDB0038629)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0038629)

Not Available

Nutrient (HMDB: HMDB0038629)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	218 - 220 °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	0.061 g/L	ALOGPS
logP	3.04	ALOGPS
logP	2.81	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	7.46	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	97.7 m³·mol⁻¹	ChemAxon
Polarizability	36.93 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	178.022	31661259
DarkChem	[M-H]-	179.224	31661259
DeepCCS	[M+H]+	185.835	30932474
DeepCCS	[M-H]-	183.421	30932474
DeepCCS	[M-2H]-	217.776	30932474
DeepCCS	[M+Na]+	193.352	30932474
AllCCS	[M+H]+	180.5	32859911
AllCCS	[M+H-H2O]+	177.3	32859911
AllCCS	[M+NH4]+	183.4	32859911
AllCCS	[M+Na]+	184.3	32859911
AllCCS	[M-H]-	187.3	32859911
AllCCS	[M+Na-2H]-	186.8	32859911
AllCCS	[M+HCOO]-	186.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Litebamine	COC1=C(O)C=C2C=CC3=C4CCN(C)CC4=C(O)C(OC)=C3C2=C1	4419.1	Standard polar	33892256
Litebamine	COC1=C(O)C=C2C=CC3=C4CCN(C)CC4=C(O)C(OC)=C3C2=C1	2936.4	Standard non polar	33892256
Litebamine	COC1=C(O)C=C2C=CC3=C4CCN(C)CC4=C(O)C(OC)=C3C2=C1	3437.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Litebamine,1TMS,isomer #1	COC1=CC2=C(C=CC3=C4CCN(C)CC4=C(O)C(OC)=C32)C=C1O[Si](C)(C)C	3038.2	Semi standard non polar	33892256
Litebamine,1TMS,isomer #2	COC1=CC2=C(C=CC3=C4CCN(C)CC4=C(O[Si](C)(C)C)C(OC)=C32)C=C1O	3026.1	Semi standard non polar	33892256
Litebamine,2TMS,isomer #1	COC1=CC2=C(C=CC3=C4CCN(C)CC4=C(O[Si](C)(C)C)C(OC)=C32)C=C1O[Si](C)(C)C	2928.1	Semi standard non polar	33892256
Litebamine,1TBDMS,isomer #1	COC1=CC2=C(C=CC3=C4CCN(C)CC4=C(O)C(OC)=C32)C=C1O[Si](C)(C)C(C)(C)C	3248.5	Semi standard non polar	33892256
Litebamine,1TBDMS,isomer #2	COC1=CC2=C(C=CC3=C4CCN(C)CC4=C(O[Si](C)(C)C(C)(C)C)C(OC)=C32)C=C1O	3246.7	Semi standard non polar	33892256
Litebamine,2TBDMS,isomer #1	COC1=CC2=C(C=CC3=C4CCN(C)CC4=C(O[Si](C)(C)C(C)(C)C)C(OC)=C32)C=C1O[Si](C)(C)C(C)(C)C	3320.2	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 - Litebamine GC-MS (Non-derivatized) - 70eV, Positive	splash10-022a-0179000000-2ae81d91140428ca464d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Litebamine GC-MS (2 TMS) - 70eV, Positive	splash10-01b9-1100900000-5b74f617eb994eddce28	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Litebamine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Litebamine 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 - Litebamine 10V, Positive-QTOF	splash10-0006-0009000000-2fa686604c1dfe3244ae	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litebamine 20V, Positive-QTOF	splash10-0005-0069000000-b02a143482696a1dc7b2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litebamine 40V, Positive-QTOF	splash10-000b-1091000000-57031a477d9daf18cf17	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litebamine 10V, Negative-QTOF	splash10-000i-0009000000-383da05728a7b575de13	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litebamine 20V, Negative-QTOF	splash10-000i-0009000000-5ee23596f949a88b0928	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litebamine 40V, Negative-QTOF	splash10-0f6x-0092000000-bb6b639991b805823a64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litebamine 10V, Positive-QTOF	splash10-0006-0009000000-952964009ca467e58825	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litebamine 20V, Positive-QTOF	splash10-0007-0059000000-f138139b4610fc6bde78	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litebamine 40V, Positive-QTOF	splash10-02t9-2094000000-f247240968c27f560f86	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litebamine 10V, Negative-QTOF	splash10-000i-0009000000-a9f00908271fb71883c3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litebamine 20V, Negative-QTOF	splash10-000i-0009000000-4c2c8e405236115a9cd4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Litebamine 40V, Negative-QTOF	splash10-029l-0093000000-35f438df67e570781659	2021-09-22	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

FDB018023

KNApSAcK ID

C00028482

Chemspider ID

170528

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

196885

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 Litebamine (HMDB0038629)

MOL for HMDB0038629 (Litebamine)

3D MOL for HMDB0038629 (Litebamine)

3D SDF for HMDB0038629 (Litebamine)

3D-SDF for HMDB0038629 (Litebamine)

PDB for HMDB0038629 (Litebamine)

3D PDB for HMDB0038629 (Litebamine)

SMILES for HMDB0038629 (Litebamine)

INCHI for HMDB0038629 (Litebamine)

Structure for HMDB0038629 (Litebamine)

3D Structure for HMDB0038629 (Litebamine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra