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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 15:04:05 UTC

Update Date

2021-09-26 23:10:13 UTC

HMDB ID

HMDB0255431

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Nalfurafine

Description

N-[4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-yl]-3-(furan-3-yl)-N-methylprop-2-enamide belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene. Based on a literature review very few articles have been published on N-[4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0¹,¹³.0⁵,¹⁷.0⁷,¹⁸]octadeca-7(18),8,10-trien-14-yl]-3-(furan-3-yl)-N-methylprop-2-enamide. This compound has been identified in human blood as reported by (PMID: 31557052 ). Nalfurafine is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Nalfurafine 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


  Mrv1652309112117042D          

 35 41  0  0  0  0            999 V2000
    1.4155   -3.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8638   -2.4218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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 31 35  1  0  0  0  0
M  END

HMDB0255431
     RDKit          3D
Nalfurafine
 67 73  0  0  0  0  0  0  0  0999 V2000
    2.4408   -1.4481    0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652309112117042D          

 35 41  0  0  0  0            999 V2000
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 29 27  1  4  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 31 35  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0255431

> <DATABASE_NAME>
hmdb

> <SMILES>
CN(C1CCC2(O)C3CC4=C5C(OC1C25CCN3CC1CC1)=C(O)C=C4)C(=O)C=CC1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C28H32N2O5/c1-29(23(32)7-4-18-9-13-34-16-18)20-8-10-28(33)22-14-19-5-6-21(31)25-24(19)27(28,26(20)35-25)11-12-30(22)15-17-2-3-17/h4-7,9,13,16-17,20,22,26,31,33H,2-3,8,10-12,14-15H2,1H3

> <INCHI_KEY>
XGZZHZMWIXFATA-UHFFFAOYSA-N

> <FORMULA>
C28H32N2O5

> <MOLECULAR_WEIGHT>
476.573

> <EXACT_MASS>
476.231122138

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
51.158558636565644

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-yl]-3-(furan-3-yl)-N-methylprop-2-enamide

> <ALOGPS_LOGP>
3.24

> <JCHEM_LOGP>
2.2386598117876972

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
13.615845904168754

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.292828454162096

> <JCHEM_PKA_STRONGEST_BASIC>
9.505232316263877

> <JCHEM_POLAR_SURFACE_AREA>
86.38000000000001

> <JCHEM_REFRACTIVITY>
131.32649999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-yl]-3-(furan-3-yl)-N-methylprop-2-enamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0255431
     RDKit          3D
Nalfurafine
 67 73  0  0  0  0  0  0  0  0999 V2000
    2.4408   -1.4481    0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3286   -0.0119    0.6626 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667    0.7177    0.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538    2.0028    0.4004 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8535    0.2917    0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0639   -0.1325    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1654    0.8369    0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5088    0.5483    0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1245    1.7651   -0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2254    2.6750   -0.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0189    2.1703    0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0940    0.7437    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874    0.4767    1.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2272    0.8088    1.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669   -0.1687    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0829   -1.4199    1.0847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809   -0.5124    0.4261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1994   -1.7478   -0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9379   -2.0891   -1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488   -3.3150   -1.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5142   -3.6121   -2.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054   -2.6704   -2.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334   -2.9618   -2.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3095   -1.4156   -1.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056   -1.2190   -1.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112    0.1630   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119    1.0227   -1.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531    0.9550   -1.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8783    0.5039   -0.2557 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3216    1.5164    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3774    0.9038    1.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9942    1.6788    2.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7791    1.4356    1.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211    0.5771   -0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0925   -0.2596   -1.6008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0461   -1.8247   -0.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9316   -1.7873    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4509   -1.9544    0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5021   -1.0369    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4326   -1.1749    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9438   -0.4462    0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1912    1.8693   -0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0882    2.7501    0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4406    1.8379    0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6735    1.0087    2.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2713   -0.5948    2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6813    0.7709    2.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1711    1.8709    1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -1.8774    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5549   -0.6961    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0798   -1.6629   -1.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4003   -2.5952    0.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -4.0617   -1.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3220   -4.5738   -2.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874   -2.2580   -2.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895    2.1078   -1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5442    0.6767   -2.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7473    1.9727   -1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030    0.3368   -2.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5293    1.8985    1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7884    2.3671    0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3533   -0.1876    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3420    1.1304    3.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6504    2.7151    2.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6222    0.7249    1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9635    2.2960    0.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567    1.5888   -1.1622 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
  3  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 26 34  1  0
 34 35  1  0
 11  7  2  0
 34 12  1  0
 26 15  1  0
 33 31  1  0
 29 17  1  0
 25 19  1  0
 35 24  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  6 40  1  0
  8 41  1  0
  9 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 20 53  1  0
 21 54  1  0
 23 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 32 63  1  0
 32 64  1  0
 33 65  1  0
 33 66  1  0
 34 67  1  0
M  END

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.642  -5.666   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       1.612  -4.521   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.089  -3.056   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.046  -1.936   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.630  -0.552   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.448  -0.278   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.549   1.188   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.077   1.168   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.635  -0.229   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.659  -1.435   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.031  -1.204   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.631  -2.757   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.873  -3.696   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.201  -2.868   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.785  -3.043   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.756  -1.819   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.174  -0.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.378  -4.465   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.454  -0.087   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.188   1.570   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       3.534   2.286   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       3.792   3.805   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.605   4.787   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.087   5.044   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.069   6.230   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       2.658   1.044   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.106  -4.840   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -0.371  -6.305   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -0.924  -3.695   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.431  -4.015   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -3.460  -2.870   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -4.992  -3.030   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -5.618  -1.623   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -4.473  -0.593   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.139  -1.363   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4   12                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11   26                                             
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10    6   12   19                                             
CONECT   12   11    3   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   10   15                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16    9                                                       
CONECT   18   15                                                            
CONECT   19   11   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    7   22                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23   25                                                       
CONECT   25   24   23                                                       
CONECT   26    6                                                            
CONECT   27    2   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   35                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   31                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

COMPND    HMDB0255431
HETATM    1  C1  UNL     1       2.441  -1.448   0.781  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.329  -0.012   0.663  1.00  0.00           N  
HETATM    3  C2  UNL     1       3.567   0.718   0.527  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.354   2.003   0.400  1.00  0.00           O  
HETATM    5  C3  UNL     1       4.853   0.292   0.503  1.00  0.00           C  
HETATM    6  C4  UNL     1       6.064  -0.133   0.484  1.00  0.00           C  
HETATM    7  C5  UNL     1       7.165   0.837   0.212  1.00  0.00           C  
HETATM    8  C6  UNL     1       8.509   0.548   0.098  1.00  0.00           C  
HETATM    9  C7  UNL     1       9.124   1.765  -0.172  1.00  0.00           C  
HETATM   10  O2  UNL     1       8.225   2.675  -0.209  1.00  0.00           O  
HETATM   11  C8  UNL     1       7.019   2.170   0.019  1.00  0.00           C  
HETATM   12  C9  UNL     1       1.094   0.744   0.673  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.287   0.477   1.864  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.227   0.809   1.656  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.667  -0.169   0.655  1.00  0.00           C  
HETATM   16  O3  UNL     1      -1.083  -1.420   1.085  1.00  0.00           O  
HETATM   17  C13 UNL     1      -3.081  -0.512   0.426  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.199  -1.748  -0.442  1.00  0.00           C  
HETATM   19  C15 UNL     1      -1.938  -2.089  -1.158  1.00  0.00           C  
HETATM   20  C16 UNL     1      -1.749  -3.315  -1.714  1.00  0.00           C  
HETATM   21  C17 UNL     1      -0.514  -3.612  -2.310  1.00  0.00           C  
HETATM   22  C18 UNL     1       0.505  -2.670  -2.334  1.00  0.00           C  
HETATM   23  O4  UNL     1       1.733  -2.962  -2.922  1.00  0.00           O  
HETATM   24  C19 UNL     1       0.310  -1.416  -1.766  1.00  0.00           C  
HETATM   25  C20 UNL     1      -0.906  -1.219  -1.222  1.00  0.00           C  
HETATM   26  C21 UNL     1      -1.011   0.163  -0.646  1.00  0.00           C  
HETATM   27  C22 UNL     1      -1.812   1.023  -1.576  1.00  0.00           C  
HETATM   28  C23 UNL     1      -3.253   0.955  -1.438  1.00  0.00           C  
HETATM   29  N2  UNL     1      -3.878   0.504  -0.256  1.00  0.00           N  
HETATM   30  C24 UNL     1      -4.322   1.516   0.670  1.00  0.00           C  
HETATM   31  C25 UNL     1      -5.377   0.904   1.605  1.00  0.00           C  
HETATM   32  C26 UNL     1      -5.994   1.679   2.701  1.00  0.00           C  
HETATM   33  C27 UNL     1      -6.779   1.436   1.434  1.00  0.00           C  
HETATM   34  C28 UNL     1       0.421   0.577  -0.640  1.00  0.00           C  
HETATM   35  O5  UNL     1       1.092  -0.260  -1.601  1.00  0.00           O  
HETATM   36  H1  UNL     1       3.046  -1.825  -0.085  1.00  0.00           H  
HETATM   37  H2  UNL     1       2.932  -1.787   1.721  1.00  0.00           H  
HETATM   38  H3  UNL     1       1.451  -1.954   0.805  1.00  0.00           H  
HETATM   39  H4  UNL     1       4.502  -1.037   0.863  1.00  0.00           H  
HETATM   40  H5  UNL     1       6.433  -1.175   0.640  1.00  0.00           H  
HETATM   41  H6  UNL     1       8.944  -0.446   0.210  1.00  0.00           H  
HETATM   42  H7  UNL     1      10.191   1.869  -0.320  1.00  0.00           H  
HETATM   43  H8  UNL     1       6.088   2.750   0.044  1.00  0.00           H  
HETATM   44  H9  UNL     1       1.441   1.838   0.721  1.00  0.00           H  
HETATM   45  H10 UNL     1       0.673   1.009   2.744  1.00  0.00           H  
HETATM   46  H11 UNL     1       0.271  -0.595   2.134  1.00  0.00           H  
HETATM   47  H12 UNL     1      -1.681   0.771   2.639  1.00  0.00           H  
HETATM   48  H13 UNL     1      -1.171   1.871   1.309  1.00  0.00           H  
HETATM   49  H14 UNL     1      -1.754  -1.877   1.663  1.00  0.00           H  
HETATM   50  H15 UNL     1      -3.555  -0.696   1.413  1.00  0.00           H  
HETATM   51  H16 UNL     1      -4.080  -1.663  -1.098  1.00  0.00           H  
HETATM   52  H17 UNL     1      -3.400  -2.595   0.280  1.00  0.00           H  
HETATM   53  H18 UNL     1      -2.522  -4.062  -1.722  1.00  0.00           H  
HETATM   54  H19 UNL     1      -0.322  -4.574  -2.749  1.00  0.00           H  
HETATM   55  H20 UNL     1       2.487  -2.258  -2.928  1.00  0.00           H  
HETATM   56  H21 UNL     1      -1.489   2.108  -1.495  1.00  0.00           H  
HETATM   57  H22 UNL     1      -1.544   0.677  -2.629  1.00  0.00           H  
HETATM   58  H23 UNL     1      -3.747   1.973  -1.654  1.00  0.00           H  
HETATM   59  H24 UNL     1      -3.703   0.337  -2.298  1.00  0.00           H  
HETATM   60  H25 UNL     1      -3.529   1.899   1.344  1.00  0.00           H  
HETATM   61  H26 UNL     1      -4.788   2.367   0.155  1.00  0.00           H  
HETATM   62  H27 UNL     1      -5.353  -0.188   1.690  1.00  0.00           H  
HETATM   63  H28 UNL     1      -6.342   1.130   3.628  1.00  0.00           H  
HETATM   64  H29 UNL     1      -5.650   2.715   2.956  1.00  0.00           H  
HETATM   65  H30 UNL     1      -7.622   0.725   1.482  1.00  0.00           H  
HETATM   66  H31 UNL     1      -6.963   2.296   0.750  1.00  0.00           H  
HETATM   67  H32 UNL     1       0.457   1.589  -1.162  1.00  0.00           H  
CONECT    1    2   36   37   38
CONECT    2    3   12
CONECT    3    4    4    5
CONECT    5    6    6   39
CONECT    6    7   40
CONECT    7    8   11   11
CONECT    8    9    9   41
CONECT    9   10   42
CONECT   10   11
CONECT   11   43
CONECT   12   13   34   44
CONECT   13   14   45   46
CONECT   14   15   47   48
CONECT   15   16   17   26
CONECT   16   49
CONECT   17   18   29   50
CONECT   18   19   51   52
CONECT   19   20   20   25
CONECT   20   21   53
CONECT   21   22   22   54
CONECT   22   23   24
CONECT   23   55
CONECT   24   25   25   35
CONECT   25   26
CONECT   26   27   34
CONECT   27   28   56   57
CONECT   28   29   58   59
CONECT   29   30
CONECT   30   31   60   61
CONECT   31   32   33   62
CONECT   32   33   63   64
CONECT   33   65   66
CONECT   34   35   67
END

HMDB0255431
     RDKit          3D
Nalfurafine
 67 73  0  0  0  0  0  0  0  0999 V2000
    2.4408   -1.4481    0.7805 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3286   -0.0119    0.6626 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5667    0.7177    0.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538    2.0028    0.4004 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8535    0.2917    0.5027 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0639   -0.1325    0.4841 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1654    0.8369    0.2117 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5088    0.5483    0.0980 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1245    1.7651   -0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2254    2.6750   -0.2088 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0189    2.1703    0.0189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0940    0.7437    0.6730 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2874    0.4767    1.8637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2272    0.8088    1.6557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6669   -0.1687    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0829   -1.4199    1.0847 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0809   -0.5124    0.4261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1994   -1.7478   -0.4420 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9379   -2.0891   -1.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7488   -3.3150   -1.7143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5142   -3.6121   -2.3097 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5054   -2.6704   -2.3339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7334   -2.9618   -2.9224 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3095   -1.4156   -1.7660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056   -1.2190   -1.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0112    0.1630   -0.6463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8119    1.0227   -1.5756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2531    0.9550   -1.4381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8783    0.5039   -0.2557 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3216    1.5164    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3774    0.9038    1.6049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9942    1.6788    2.7011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7791    1.4356    1.4335 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4211    0.5771   -0.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0925   -0.2596   -1.6008 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0461   -1.8247   -0.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9316   -1.7873    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4509   -1.9544    0.8050 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5021   -1.0369    0.8629 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4326   -1.1749    0.6401 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9438   -0.4462    0.2101 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1912    1.8693   -0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0882    2.7501    0.0439 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4406    1.8379    0.7213 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6735    1.0087    2.7442 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2713   -0.5948    2.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6813    0.7709    2.6392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1711    1.8709    1.3094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -1.8774    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5549   -0.6961    1.4128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0798   -1.6629   -1.0977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4003   -2.5952    0.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5223   -4.0617   -1.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3220   -4.5738   -2.7494 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4874   -2.2580   -2.9281 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4895    2.1078   -1.4951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5442    0.6767   -2.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7473    1.9727   -1.6539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7030    0.3368   -2.2978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5293    1.8985    1.3440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7884    2.3671    0.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3533   -0.1876    1.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3420    1.1304    3.6285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6504    2.7151    2.9560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6222    0.7249    1.4823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9635    2.2960    0.7497 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567    1.5888   -1.1622 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
  3  5  1  0
  5  6  2  3
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
  2 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 26 34  1  0
 34 35  1  0
 11  7  2  0
 34 12  1  0
 26 15  1  0
 33 31  1  0
 29 17  1  0
 25 19  1  0
 35 24  1  0
  1 36  1  0
  1 37  1  0
  1 38  1  0
  5 39  1  0
  6 40  1  0
  8 41  1  0
  9 42  1  0
 11 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 16 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 20 53  1  0
 21 54  1  0
 23 55  1  0
 27 56  1  0
 27 57  1  0
 28 58  1  0
 28 59  1  0
 30 60  1  0
 30 61  1  0
 31 62  1  0
 32 63  1  0
 32 64  1  0
 33 65  1  0
 33 66  1  0
 34 67  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₈H₃₂N₂O₅

Average Molecular Weight

476.573

Monoisotopic Molecular Weight

476.231122138

IUPAC Name

N-[4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-yl]-3-(furan-3-yl)-N-methylprop-2-enamide

Traditional Name

N-[4-(cyclopropylmethyl)-10,17-dihydroxy-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10-trien-14-yl]-3-(furan-3-yl)-N-methylprop-2-enamide

CAS Registry Number

Not Available

SMILES

CN(C1CCC2(O)C3CC4=C5C(OC1C25CCN3CC1CC1)=C(O)C=C4)C(=O)C=CC1=COC=C1

InChI Identifier

InChI=1S/C28H32N2O5/c1-29(23(32)7-4-18-9-13-34-16-18)20-8-10-28(33)22-14-19-5-6-21(31)25-24(19)27(28,26(20)35-25)11-12-30(22)15-17-2-3-17/h4-7,9,13,16-17,20,22,26,31,33H,2-3,8,10-12,14-15H2,1H3

InChI Key

XGZZHZMWIXFATA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenanthrenes and derivatives. These are polycyclic compounds containing a phenanthrene moiety, which is a tricyclic aromatic compound with three non-linearly fused benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenanthrenes and derivatives

Sub Class

Not Available

Direct Parent

Phenanthrenes and derivatives

Alternative Parents

Substituents

Phenanthrene
Tetralin
Coumaran
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aralkylamine
Piperidine
Tertiary alcohol
Tertiary carboxylic acid amide
Cyclic alcohol
Heteroaromatic compound
Furan
Tertiary aliphatic amine
Carboxamide group
Amino acid or derivatives
Tertiary amine
1,2-aminoalcohol
Carboxylic acid derivative
Ether
Oxacycle
Azacycle
Organoheterocyclic compound
Alcohol
Hydrocarbon derivative
Organic nitrogen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Organonitrogen compound
Organooxygen compound
Amine
Organopnictogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	3.24	ALOGPS
logP	2.24	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	10.29	ChemAxon
pKa (Strongest Basic)	9.51	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	86.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.33 m³·mol⁻¹	ChemAxon
Polarizability	51.16 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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-2H]-	244.332	30932474
DeepCCS	[M+Na]+	219.756	30932474
AllCCS	[M+H]+	214.8	32859911
AllCCS	[M+H-H2O]+	213.1	32859911
AllCCS	[M+NH4]+	216.4	32859911
AllCCS	[M+Na]+	216.8	32859911
AllCCS	[M-H]-	204.0	32859911
AllCCS	[M+Na-2H]-	204.8	32859911
AllCCS	[M+HCOO]-	205.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nalfurafine	CN(C1CCC2(O)C3CC4=C5C(OC1C25CCN3CC1CC1)=C(O)C=C4)C(=O)C=CC1=COC=C1	5251.8	Standard polar	33892256
Nalfurafine	CN(C1CCC2(O)C3CC4=C5C(OC1C25CCN3CC1CC1)=C(O)C=C4)C(=O)C=CC1=COC=C1	3704.8	Standard non polar	33892256
Nalfurafine	CN(C1CCC2(O)C3CC4=C5C(OC1C25CCN3CC1CC1)=C(O)C=C4)C(=O)C=CC1=COC=C1	4139.8	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 - Nalfurafine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-4900300000-0f9ab6808ac4c3bdbbc2	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalfurafine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalfurafine GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalfurafine GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalfurafine GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalfurafine GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalfurafine GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nalfurafine GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	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

Not Available

Chemspider ID

24995700

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73046431

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 Nalfurafine (HMDB0255431)

MOL for HMDB0255431 (Nalfurafine)

3D MOL for HMDB0255431 (Nalfurafine)

3D SDF for HMDB0255431 (Nalfurafine)

3D-SDF for HMDB0255431 (Nalfurafine)

PDB for HMDB0255431 (Nalfurafine)

3D PDB for HMDB0255431 (Nalfurafine)

SMILES for HMDB0255431 (Nalfurafine)

INCHI for HMDB0255431 (Nalfurafine)

Structure for HMDB0255431 (Nalfurafine)

3D Structure for HMDB0255431 (Nalfurafine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra