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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 19:45:52 UTC

Update Date

2021-09-26 23:15:08 UTC

HMDB ID

HMDB0258333

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Skimmianine

Description

4,7,8-trimethoxyfuro[2,3-b]quinoline belongs to the class of organic compounds known as furanoquinolines. Furanoquinolines are compounds containing a furan ring fused to a quinoline. 4,7,8-trimethoxyfuro[2,3-b]quinoline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 4,7,8-trimethoxyfuro[2,3-b]quinoline. This compound has been identified in human blood as reported by (PMID: 31557052 ). Skimmianine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Skimmianine is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0258333
     RDKit          3D
Skimmianine
 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.8772    2.6089   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4337    1.3174   -0.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869    0.9947    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1400    1.9855   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1896    1.6392    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052    0.3617    0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9326    0.0544    0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9059    1.0096    0.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5526    1.3657   -0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2906   -1.2386    0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212   -1.8600    0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2309   -3.1879    1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9460   -3.3539    1.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155   -2.2332    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104   -1.8958    0.7276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720   -0.6318    0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7070   -0.3009    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7018   -1.2464    0.4479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2236   -2.0231   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6869    2.7865   -1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3938    3.3962    0.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9784    2.6522   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    3.0132   -0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9583    2.4026   -0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0425    0.9913   -1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105    1.0332   -0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6021    2.4850   -0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097   -1.4080    0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0150   -3.9322    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7836   -3.0373   -0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3166   -2.1653   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1233   -1.5830   -1.5895 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  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17  3  1  0
 16  6  1  0
 14 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 19 30  1  0
 19 31  1  0
 19 32  1  0
M  END

  Mrv1533005011511252D          

 19 21  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8419   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -1.4924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  7 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 10 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
  6 16  1  0  0  0  0
 16 17  2  0  0  0  0
  3 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0258333

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C(OC)=C3C=COC3=NC2=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C14H13NO4/c1-16-10-5-4-8-11(13(10)18-3)15-14-9(6-7-19-14)12(8)17-2/h4-7H,1-3H3

> <INCHI_KEY>
SLSIBLKBHNKZTB-UHFFFAOYSA-N

> <FORMULA>
C14H13NO4

> <MOLECULAR_WEIGHT>
259.261

> <EXACT_MASS>
259.084457903

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
26.53245127978839

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,7,8-trimethoxyfuro[2,3-b]quinoline

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
2.184472129999999

> <ALOGPS_LOGS>
-3.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
1.779285304660056

> <JCHEM_POLAR_SURFACE_AREA>
53.72

> <JCHEM_REFRACTIVITY>
68.16260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.69e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
skimmianine

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258333
     RDKit          3D
Skimmianine
 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.8772    2.6089   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4337    1.3174   -0.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869    0.9947    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1400    1.9855   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1896    1.6392    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052    0.3617    0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9326    0.0544    0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9059    1.0096    0.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5526    1.3657   -0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2906   -1.2386    0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212   -1.8600    0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2309   -3.1879    1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9460   -3.3539    1.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155   -2.2332    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104   -1.8958    0.7276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720   -0.6318    0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7070   -0.3009    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7018   -1.2464    0.4479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2236   -2.0231   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6869    2.7865   -1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3938    3.3962    0.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9784    2.6522   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    3.0132   -0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9583    2.4026   -0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0425    0.9913   -1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105    1.0332   -0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6021    2.4850   -0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097   -1.4080    0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0150   -3.9322    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7836   -3.0373   -0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3166   -2.1653   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1233   -1.5830   -1.5895 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  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17  3  1  0
 16  6  1  0
 14 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 19 30  1  0
 19 31  1  0
 19 32  1  0
M  END

HEADER    PROTEIN                                 01-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   01-MAY-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.133  -0.294   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.038  -1.540   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       8.133  -2.786   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       5.335  -3.080   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   17                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   16                                                  
CONECT    7    6    8   10                                                  
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    7   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    6   17                                                  
CONECT   17   16    3   18                                                  
CONECT   18   17   19                                                       
CONECT   19   18                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

COMPND    HMDB0258333
HETATM    1  C1  UNL     1      -3.877   2.609  -0.385  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.434   1.317  -0.103  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.087   0.995   0.036  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.140   1.986  -0.109  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.190   1.639   0.034  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.605   0.362   0.311  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.933   0.054   0.446  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.906   1.010   0.310  1.00  0.00           O  
HETATM    9  C7  UNL     1       3.553   1.366  -0.870  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.291  -1.239   0.723  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.521  -1.860   0.915  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.231  -3.188   1.163  1.00  0.00           C  
HETATM   13  O3  UNL     1       1.946  -3.354   1.125  1.00  0.00           O  
HETATM   14  C11 UNL     1       1.316  -2.233   0.867  1.00  0.00           C  
HETATM   15  N1  UNL     1       0.010  -1.896   0.728  1.00  0.00           N  
HETATM   16  C12 UNL     1      -0.372  -0.632   0.455  1.00  0.00           C  
HETATM   17  C13 UNL     1      -1.707  -0.301   0.315  1.00  0.00           C  
HETATM   18  O4  UNL     1      -2.702  -1.246   0.448  1.00  0.00           O  
HETATM   19  C14 UNL     1      -3.224  -2.023  -0.588  1.00  0.00           C  
HETATM   20  H1  UNL     1      -3.687   2.786  -1.484  1.00  0.00           H  
HETATM   21  H2  UNL     1      -3.394   3.396   0.232  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.978   2.652  -0.271  1.00  0.00           H  
HETATM   23  H4  UNL     1      -1.414   3.013  -0.329  1.00  0.00           H  
HETATM   24  H5  UNL     1       0.958   2.403  -0.076  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.043   0.991  -1.769  1.00  0.00           H  
HETATM   26  H7  UNL     1       4.611   1.033  -0.797  1.00  0.00           H  
HETATM   27  H8  UNL     1       3.602   2.485  -0.956  1.00  0.00           H  
HETATM   28  H9  UNL     1       4.510  -1.408   0.880  1.00  0.00           H  
HETATM   29  H10 UNL     1       4.015  -3.932   1.355  1.00  0.00           H  
HETATM   30  H11 UNL     1      -2.784  -3.037  -0.605  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.317  -2.165  -0.412  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.123  -1.583  -1.590  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4   17
CONECT    4    5   23
CONECT    5    6    6   24
CONECT    6    7   16
CONECT    7    8   10   10
CONECT    8    9
CONECT    9   25   26   27
CONECT   10   11   14
CONECT   11   12   12   28
CONECT   12   13   29
CONECT   13   14
CONECT   14   15   15
CONECT   15   16
CONECT   16   17   17
CONECT   17   18
CONECT   18   19
CONECT   19   30   31   32
END

HMDB0258333
     RDKit          3D
Skimmianine
 32 34  0  0  0  0  0  0  0  0999 V2000
   -3.8772    2.6089   -0.3849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4337    1.3174   -0.1031 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0869    0.9947    0.0358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1400    1.9855   -0.1089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1896    1.6392    0.0338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052    0.3617    0.3111 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9326    0.0544    0.4459 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9059    1.0096    0.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5526    1.3657   -0.8704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2906   -1.2386    0.7232 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5212   -1.8600    0.9151 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2309   -3.1879    1.1634 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9460   -3.3539    1.1252 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3155   -2.2332    0.8671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0104   -1.8958    0.7276 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3720   -0.6318    0.4547 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7070   -0.3009    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7018   -1.2464    0.4479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2236   -2.0231   -0.5885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6869    2.7865   -1.4836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3938    3.3962    0.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9784    2.6522   -0.2710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4140    3.0132   -0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9583    2.4026   -0.0756 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0425    0.9913   -1.7686 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6105    1.0332   -0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6021    2.4850   -0.9561 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5097   -1.4080    0.8800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0150   -3.9322    1.3551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7836   -3.0373   -0.6049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3166   -2.1653   -0.4118 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1233   -1.5830   -1.5895 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  1  0
  8  9  1  0
  7 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 17  3  1  0
 16  6  1  0
 14 10  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  5 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 19 30  1  0
 19 31  1  0
 19 32  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4,7,8-Trimethoxy-furo(2,3-b)quinoline	MeSH

Chemical Formula

C₁₄H₁₃NO₄

Average Molecular Weight

259.261

Monoisotopic Molecular Weight

259.084457903

IUPAC Name

4,7,8-trimethoxyfuro[2,3-b]quinoline

Traditional Name

skimmianine

CAS Registry Number

Not Available

SMILES

COC1=CC=C2C(OC)=C3C=COC3=NC2=C1OC

InChI Identifier

InChI=1S/C14H13NO4/c1-16-10-5-4-8-11(13(10)18-3)15-14-9(6-7-19-14)12(8)17-2/h4-7H,1-3H3

InChI Key

SLSIBLKBHNKZTB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoquinolines. Furanoquinolines are compounds containing a furan ring fused to a quinoline.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Quinolines and derivatives

Sub Class

Furanoquinolines

Direct Parent

Furanoquinolines

Alternative Parents

Substituents

Furanoquinoline
Furopyridine
Anisole
Alkyl aryl ether
Pyridine
Benzenoid
Furan
Heteroaromatic compound
Oxacycle
Azacycle
Ether
Organic oxygen compound
Organic nitrogen compound
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

organic heterotricyclic compound (CHEBI:9172 )
oxacycle (CHEBI:9172 )
organonitrogen heterocyclic compound (CHEBI:9172 )
alkaloid antibiotic (CHEBI:9172 )
Quinoline alkaloids (C10740 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.05	ALOGPS
logP	2.18	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Basic)	1.78	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	53.72 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.16 m³·mol⁻¹	ChemAxon
Polarizability	26.53 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	160.907	30932474
DeepCCS	[M-H]-	158.549	30932474
DeepCCS	[M-2H]-	191.436	30932474
DeepCCS	[M+Na]+	167.0	30932474
AllCCS	[M+H]+	157.6	32859911
AllCCS	[M+H-H2O]+	153.6	32859911
AllCCS	[M+NH4]+	161.2	32859911
AllCCS	[M+Na]+	162.2	32859911
AllCCS	[M-H]-	162.0	32859911
AllCCS	[M+Na-2H]-	161.6	32859911
AllCCS	[M+HCOO]-	161.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Skimmianine	COC1=CC=C2C(OC)=C3C=COC3=NC2=C1OC	3019.1	Standard polar	33892256
Skimmianine	COC1=CC=C2C(OC)=C3C=COC3=NC2=C1OC	2243.3	Standard non polar	33892256
Skimmianine	COC1=CC=C2C(OC)=C3C=COC3=NC2=C1OC	2408.6	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 - Skimmianine GC-MS (Non-derivatized) - 70eV, Positive	splash10-00pl-0290000000-e8eb10a08a0f038dccda	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Skimmianine 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Skimmianine 20V, Positive-QTOF	splash10-01t9-0090000000-8d3fa15864b28744f48c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Skimmianine 10V, Positive-QTOF	splash10-03di-0090000000-464d9f2b0b52ec3c9207	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Skimmianine 10V, Positive-QTOF	splash10-03di-0090000000-0546245b50be26e33ced	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Skimmianine 40V, Positive-QTOF	splash10-0kcr-0930000000-67f34594aac1a9a0e7cb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Skimmianine 40V, Positive-QTOF	splash10-0kcs-0940000000-43dd4143855880fbbe35	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Skimmianine 20V, Positive-QTOF	splash10-004i-0190000000-edfffb1ab3bc5116e00c	2021-09-20	HMDB team, MONA	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

C00002198

Chemspider ID

6502

KEGG Compound ID

C10740

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Skimmianine (HMDB0258333)

MOL for HMDB0258333 (Skimmianine)

3D MOL for HMDB0258333 (Skimmianine)

3D SDF for HMDB0258333 (Skimmianine)

3D-SDF for HMDB0258333 (Skimmianine)

PDB for HMDB0258333 (Skimmianine)

3D PDB for HMDB0258333 (Skimmianine)

SMILES for HMDB0258333 (Skimmianine)

INCHI for HMDB0258333 (Skimmianine)

Structure for HMDB0258333 (Skimmianine)

3D Structure for HMDB0258333 (Skimmianine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra