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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:35:47 UTC

Update Date

2022-03-07 02:52:29 UTC

HMDB ID

HMDB0030264

Secondary Accession Numbers

HMDB30264

Metabolite Identification

Common Name

(R)-Roemerine

Description

(R)-Roemerine, also known as remerin or aporeine, belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof. Based on a literature review a significant number of articles have been published on (R)-Roemerine.

Structure

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

HMDB0030264
     RDKit          3D
(R)-Roemerine
 38 42  0  0  0  0  0  0  0  0999 V2000
    3.3763   -1.1621   -0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7658   -0.2285    0.0677 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1713    1.0731   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3431    2.1744    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981    1.8720    0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0547    2.9385    0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3051    2.6940    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8045    1.3934    0.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9156    0.3495    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4578    0.5944    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3896   -0.5121    0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8828   -1.6836   -0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5225   -2.0154   -0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656   -3.3308   -0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -3.6267   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -2.5960    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7788   -1.2834    0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4400   -1.0023    0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1811    1.4249    0.4768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5243    2.7771    0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4170    3.5277    0.5970 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4408   -0.8095   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4580   -2.1858   -0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274   -1.1122   -1.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2400    1.2065   -1.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188    1.2281    0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931    3.0773   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6682    2.4511    1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657    3.9736    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3997   -0.8692    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8978   -1.4609   -1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741   -2.6166   -0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2139   -4.0928   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6010   -4.6677   -0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2284   -2.9031    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5386   -0.5683    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4349    3.0673    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5706    2.9043   -0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  8 19  1  0
 19 20  1  0
 20 21  1  0
 11  2  1  0
 18 13  1  0
 10  5  1  0
 21  7  1  0
 18  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 20 38  1  0
M  END


  Mrv0541 05061305072D          

 21 25  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    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
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354    2.1307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    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
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149    2.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710    1.3770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  6  1  0  0  0  0
 11  4  2  0  0  0  0
 11  8  1  0  0  0  0
 12  6  1  0  0  0  0
 12  9  2  0  0  0  0
 13  5  2  0  0  0  0
 13 11  1  0  0  0  0
 14  8  1  0  0  0  0
 15  9  1  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
 17 13  1  0  0  0  0
 17 16  2  0  0  0  0
 18 15  2  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
 19  7  1  0  0  0  0
 19 14  1  0  0  0  0
 20 10  1  0  0  0  0
 20 15  1  0  0  0  0
 21 10  1  0  0  0  0
 21 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030264

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO2/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17/h2-5,9,14H,6-8,10H2,1H3

> <INCHI_KEY>
JCTYWRARKVGOBK-UHFFFAOYSA-N

> <FORMULA>
C18H17NO2

> <MOLECULAR_WEIGHT>
279.3331

> <EXACT_MASS>
279.125928793

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.907699437952864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaene

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
3.324645495333333

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
7.517678948711366

> <JCHEM_POLAR_SURFACE_AREA>
21.700000000000003

> <JCHEM_REFRACTIVITY>
81.79319999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.02e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0030264
     RDKit          3D
(R)-Roemerine
 38 42  0  0  0  0  0  0  0  0999 V2000
    3.3763   -1.1621   -0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7658   -0.2285    0.0677 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1713    1.0731   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3431    2.1744    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981    1.8720    0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0547    2.9385    0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3051    2.6940    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8045    1.3934    0.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9156    0.3495    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4578    0.5944    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3896   -0.5121    0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8828   -1.6836   -0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5225   -2.0154   -0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656   -3.3308   -0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -3.6267   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -2.5960    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7788   -1.2834    0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4400   -1.0023    0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1811    1.4249    0.4768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5243    2.7771    0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4170    3.5277    0.5970 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4408   -0.8095   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4580   -2.1858   -0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274   -1.1122   -1.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2400    1.2065   -1.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188    1.2281    0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931    3.0773   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6682    2.4511    1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657    3.9736    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3997   -0.8692    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8978   -1.4609   -1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741   -2.6166   -0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2139   -4.0928   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6010   -4.6677   -0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2284   -2.9031    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5386   -0.5683    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4349    3.0673    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5706    2.9043   -0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  8 19  1  0
 19 20  1  0
 20 21  1  0
 11  2  1  0
 18 13  1  0
 10  5  1  0
 21  7  1  0
 18  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 20 38  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       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.853   3.977   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.667  -3.080   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       4.321   3.816   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.479   2.570   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   11                                                       
CONECT    5    3   13                                                       
CONECT    6    7   12                                                       
CONECT    7    6   19                                                       
CONECT    8   11   14                                                       
CONECT    9   12   15                                                       
CONECT   10   20   21                                                       
CONECT   11    4    8   13                                                  
CONECT   12    6    9   16                                                  
CONECT   13    5   11   17                                                  
CONECT   14    8   16   19                                                  
CONECT   15    9   18   20                                                  
CONECT   16   12   14   17                                                  
CONECT   17   13   16   18                                                  
CONECT   18   15   17   21                                                  
CONECT   19    1    7   14                                                  
CONECT   20   10   15                                                       
CONECT   21   10   18                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

COMPND    HMDB0030264
HETATM    1  C1  UNL     1       3.376  -1.162  -0.851  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.766  -0.229   0.068  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.171   1.073  -0.216  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.343   2.174   0.358  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.898   1.872   0.382  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.055   2.939   0.479  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.305   2.694   0.505  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.805   1.393   0.432  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.916   0.350   0.334  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.458   0.594   0.311  1.00  0.00           C  
HETATM   11  C10 UNL     1       1.390  -0.512   0.335  1.00  0.00           C  
HETATM   12  C11 UNL     1       0.883  -1.684  -0.425  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.523  -2.015  -0.126  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.966  -3.331  -0.201  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.290  -3.627  -0.039  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.191  -2.596   0.202  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.779  -1.283   0.284  1.00  0.00           C  
HETATM   18  C17 UNL     1      -1.440  -1.002   0.120  1.00  0.00           C  
HETATM   19  O1  UNL     1      -3.181   1.425   0.477  1.00  0.00           O  
HETATM   20  C18 UNL     1      -3.524   2.777   0.137  1.00  0.00           C  
HETATM   21  O2  UNL     1      -2.417   3.528   0.597  1.00  0.00           O  
HETATM   22  H1  UNL     1       4.441  -0.810  -0.983  1.00  0.00           H  
HETATM   23  H2  UNL     1       3.458  -2.186  -0.453  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.927  -1.112  -1.863  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.240   1.207  -1.332  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.219   1.228   0.145  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.493   3.077  -0.270  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.668   2.451   1.382  1.00  0.00           H  
HETATM   29  H8  UNL     1       0.366   3.974   0.538  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.400  -0.869   1.433  1.00  0.00           H  
HETATM   31  H10 UNL     1       0.898  -1.461  -1.535  1.00  0.00           H  
HETATM   32  H11 UNL     1       1.474  -2.617  -0.230  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.214  -4.093  -0.392  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.601  -4.668  -0.104  1.00  0.00           H  
HETATM   35  H14 UNL     1      -4.228  -2.903   0.319  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.539  -0.568   0.477  1.00  0.00           H  
HETATM   37  H16 UNL     1      -4.435   3.067   0.662  1.00  0.00           H  
HETATM   38  H17 UNL     1      -3.571   2.904  -0.955  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   11
CONECT    3    4   25   26
CONECT    4    5   27   28
CONECT    5    6    6   10
CONECT    6    7   29
CONECT    7    8    8   21
CONECT    8    9   19
CONECT    9   10   10   18
CONECT   10   11
CONECT   11   12   30
CONECT   12   13   31   32
CONECT   13   14   14   18
CONECT   14   15   33
CONECT   15   16   16   34
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   19   20
CONECT   20   21   37   38
END

HMDB0030264
     RDKit          3D
(R)-Roemerine
 38 42  0  0  0  0  0  0  0  0999 V2000
    3.3763   -1.1621   -0.8514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7658   -0.2285    0.0677 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1713    1.0731   -0.2161 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3431    2.1744    0.3578 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8981    1.8720    0.3823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0547    2.9385    0.4791 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3051    2.6940    0.5052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8045    1.3934    0.4324 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9156    0.3495    0.3336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4578    0.5944    0.3114 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3896   -0.5121    0.3347 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8828   -1.6836   -0.4249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5225   -2.0154   -0.1261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656   -3.3308   -0.2010 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2902   -3.6267   -0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1909   -2.5960    0.2021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7788   -1.2834    0.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4400   -1.0023    0.1199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1811    1.4249    0.4768 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5243    2.7771    0.1373 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4170    3.5277    0.5970 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4408   -0.8095   -0.9831 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4580   -2.1858   -0.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9274   -1.1122   -1.8632 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2400    1.2065   -1.3323 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2188    1.2281    0.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4931    3.0773   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6682    2.4511    1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3657    3.9736    0.5380 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3997   -0.8692    1.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8978   -1.4609   -1.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4741   -2.6166   -0.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2139   -4.0928   -0.3916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6010   -4.6677   -0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2284   -2.9031    0.3192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5386   -0.5683    0.4765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4349    3.0673    0.6619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5706    2.9043   -0.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  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  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
  8 19  1  0
 19 20  1  0
 20 21  1  0
 11  2  1  0
 18 13  1  0
 10  5  1  0
 21  7  1  0
 18  9  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  4 28  1  0
  6 29  1  0
 11 30  1  0
 12 31  1  0
 12 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 20 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1-(3-Furanyl)-2,4-pentanediol	HMDB
3-(1,4-Dihydroxypentyl)furan	HMDB
(-)-Aporheine	HMDB
(-)-Remerine	HMDB
(-)-Roemerine	HMDB
1,2-(Methylenedioxy)-6a-beta-aporphine	HMDB
L-Roemerine	HMDB
Remerin	HMDB
Remerine	HMDB
Remerine (alkaloid)	HMDB
Roemerin	HMDB
Roemerine	HMDB
Roemerine, (S)-isomer	HMDB
Aporeine	HMDB
Roemerine hydrochloride, (R)-isomer	HMDB

Chemical Formula

C₁₈H₁₇NO₂

Average Molecular Weight

279.3331

Monoisotopic Molecular Weight

279.125928793

IUPAC Name

11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaene

Traditional Name

11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaene

CAS Registry Number

548-08-3

SMILES

CN1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C31

InChI Identifier

InChI=1S/C18H17NO2/c1-19-7-6-12-9-15-18(21-10-20-15)17-13-5-3-2-4-11(13)8-14(19)16(12)17/h2-5,9,14H,6-8,10H2,1H3

InChI Key

JCTYWRARKVGOBK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Aralkylamine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Acetal
Azacycle
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
Organic nitrogen 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: HMDB0030264)

Cellular substructure

Membrane (HMDB: HMDB0030264)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030264)

Source

Endogenous

Endogenous (HMDB: HMDB0030264)

Plant

Plant (HMDB: HMDB0030264)
Coffea (HMDB: HMDB0030264)

Exogenous

Food

Food (HMDB: HMDB0030264)

Tea

Coffee and coffee product

Coffee

Arabica coffee (FooDB: FOOD00059)
Robusta coffee (FooDB: FOOD00060)

Coffee and coffee products (FooDB: FOOD00861)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	102 - 103 °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	0.1 g/L	ALOGPS
logP	2.9	ALOGPS
logP	3.32	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	7.52	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	21.7 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	81.79 m³·mol⁻¹	ChemAxon
Polarizability	30.91 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	165.429	31661259
DarkChem	[M-H]-	164.954	31661259
DeepCCS	[M-2H]-	192.59	30932474
DeepCCS	[M+Na]+	168.018	30932474
AllCCS	[M+H]+	165.1	32859911
AllCCS	[M+H-H2O]+	161.4	32859911
AllCCS	[M+NH4]+	168.6	32859911
AllCCS	[M+Na]+	169.5	32859911
AllCCS	[M-H]-	174.0	32859911
AllCCS	[M+Na-2H]-	173.0	32859911
AllCCS	[M+HCOO]-	172.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Roemerine	CN1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C31	3530.1	Standard polar	33892256
(R)-Roemerine	CN1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C31	2355.6	Standard non polar	33892256
(R)-Roemerine	CN1CCC2=CC3=C(OCO3)C3=C2C1CC1=CC=CC=C31	2549.8	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 - (R)-Roemerine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0imr-0090000000-745953c37c4239cdc051	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Roemerine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Roemerine 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 - (R)-Roemerine 6V, Positive-QTOF	splash10-001i-0090000000-635e5cee65a67747a8ce	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Roemerine 6V, Positive-QTOF	splash10-000t-0290000000-ccf3533cffb2440f079e	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Roemerine 6V, Positive-QTOF	splash10-001i-0090000000-0ca707052198b44d23d7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Roemerine 6V, Positive-QTOF	splash10-0006-0970000000-4696f1ff2275021fcba9	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Roemerine 6V, Positive-QTOF	splash10-000l-0910000000-a23cc1980f2163040272	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Roemerine 6V, Positive-QTOF	splash10-000l-0910000000-65c234023369d5e3ee68	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Roemerine 6V, Positive-QTOF	splash10-0006-0970000000-0a241e898ac444e63119	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Roemerine 6V, Positive-QTOF	splash10-0006-0980000000-626b8ace095c82f06ab4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Roemerine 6V, Positive-QTOF	splash10-001i-0090000000-7b0a7cfdf2ce2bd3ef62	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Roemerine 6V, Positive-QTOF	splash10-000w-0290000000-5c7bf3e6d0931f8358e2	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Roemerine 6V, Positive-QTOF	splash10-000t-0190000000-4ada27fdba5172875778	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Roemerine 6V, Positive-QTOF	splash10-000l-0910000000-969678333f7aa9ea0ce7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - (R)-Roemerine 6V, Positive-QTOF	splash10-000w-0290000000-8b98bdfac700a8194289	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Roemerine 10V, Positive-QTOF	splash10-001i-0090000000-2154c045ee4269a75c5b	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Roemerine 20V, Positive-QTOF	splash10-001i-0090000000-2141d74364522dacfc31	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Roemerine 40V, Positive-QTOF	splash10-0l1l-2090000000-cc95e5b518edc5612684	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Roemerine 10V, Negative-QTOF	splash10-004i-0090000000-ba19f16e005aad4b2289	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Roemerine 20V, Negative-QTOF	splash10-004i-0090000000-956d58e4bfd1e88ecc3d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Roemerine 40V, Negative-QTOF	splash10-03fr-1090000000-d824d214a83079b6a356	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Roemerine 10V, Negative-QTOF	splash10-004i-0090000000-50cc1ea4c83b57b666b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Roemerine 20V, Negative-QTOF	splash10-004i-0090000000-7ad3112870ebf77c59df	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Roemerine 40V, Negative-QTOF	splash10-01ta-0090000000-739428a703c1b0936ca6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Roemerine 10V, Positive-QTOF	splash10-001i-0090000000-ca9c209963e0693bbfab	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Roemerine 20V, Positive-QTOF	splash10-001i-0090000000-2569b55bdd82be33ca88	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Roemerine 40V, Positive-QTOF	splash10-0uds-0090000000-6f1154831c206e456218	2021-09-24	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

FDB002093

KNApSAcK ID

C00025625

Chemspider ID

205203

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13186539

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 (R)-Roemerine (HMDB0030264)

MOL for HMDB0030264 ((R)-Roemerine)

3D MOL for HMDB0030264 ((R)-Roemerine)

3D SDF for HMDB0030264 ((R)-Roemerine)

3D-SDF for HMDB0030264 ((R)-Roemerine)

PDB for HMDB0030264 ((R)-Roemerine)

3D PDB for HMDB0030264 ((R)-Roemerine)

SMILES for HMDB0030264 ((R)-Roemerine)

INCHI for HMDB0030264 ((R)-Roemerine)

Structure for HMDB0030264 ((R)-Roemerine)

3D Structure for HMDB0030264 ((R)-Roemerine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra