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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 06:57:28 UTC

Update Date

2021-09-23 06:57:28 UTC

HMDB ID

HMDB0302139

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(-)-Norushinsunine

Description

(-)-norushinsunine is a member of the class of compounds known as hydroxy-7-aporphines. Hydroxy-7-aporphines are aporphines containing a hydroxyl group at the 7-position (-)-norushinsunine is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-norushinsunine can be found in cherimoya, custard apple, and sugar apple, which makes (-)-norushinsunine a potential biomarker for the consumption of these food products.

Structure

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

HMDB0302139
     RDKit          3D
(-)-Norushinsunine
 36 40  0  0  0  0  0  0  0  0999 V2000
    0.1021   -3.4947    0.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681   -2.1293   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3888   -1.5119   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5337   -2.3342   -0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7786   -1.7683   -0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8967   -0.4079   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915    0.4124    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5316   -0.1503   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3528    0.6620    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123    2.0318    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6720    2.7668    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145    2.1938    0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0381    0.8256    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8862    0.0581    0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0122   -1.4003    0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -1.9319   -0.1315 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2429   -0.9856   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3353    0.1230    0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3198    4.1316    0.4713 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9604    4.1992   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926    2.9645    0.2497 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645   -3.9693   -0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605   -2.0841   -1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982   -3.4185   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437   -2.4232   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8955    0.0213   -0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9088    1.4410    0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291    2.7826    0.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9154   -1.7094    1.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -2.7140    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9025   -0.4994   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2118   -1.4664   -0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107    0.8283    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5599   -0.3044    1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5388    5.0620    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    4.1989   -1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
 20 21  1  0
 15  2  1  0
  8  3  1  0
 14  9  1  0
 21 10  1  0
 18 13  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 12 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
M  END


  Mrv0541 02241208452D          

 21 25  0  0  0  0            999 V2000
   -1.1322    2.0221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232    2.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0805    1.6176    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3232    0.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1622    0.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8086   -0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6468   -1.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2131   -1.7794    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0221   -1.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1839   -0.7277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5367   -0.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7794    0.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1322    1.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5367   -1.1322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1839   -0.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0221    0.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2131    0.4041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5659   -0.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7277   -0.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1614   -1.4558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3232   -2.2648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 13  2  0  0  0  0
  5  6  2  0  0  0  0
  5 18  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  7 20  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  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
 14 15  2  0  0  0  0
 14 19  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302139

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C2NCCC3=CC4=C(OCO4)C(C4=C1C=CC=C4)=C23

> <INCHI_IDENTIFIER>
InChI=1S/C17H15NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-4,7,15-16,18-19H,5-6,8H2

> <INCHI_KEY>
CKIYSMRPIBQTHQ-UHFFFAOYSA-N

> <FORMULA>
C17H15NO3

> <MOLECULAR_WEIGHT>
281.3059

> <EXACT_MASS>
281.105193351

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.834926452344234

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaen-13-ol

> <ALOGPS_LOGP>
1.14

> <JCHEM_LOGP>
2.0226014109999992

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.81936659136652

> <JCHEM_PKA_STRONGEST_BASIC>
8.855579327441925

> <JCHEM_POLAR_SURFACE_AREA>
50.72

> <JCHEM_REFRACTIVITY>
77.706

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaen-13-ol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302139
     RDKit          3D
(-)-Norushinsunine
 36 40  0  0  0  0  0  0  0  0999 V2000
    0.1021   -3.4947    0.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681   -2.1293   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3888   -1.5119   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5337   -2.3342   -0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7786   -1.7683   -0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8967   -0.4079   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915    0.4124    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5316   -0.1503   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3528    0.6620    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123    2.0318    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6720    2.7668    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145    2.1938    0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0381    0.8256    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8862    0.0581    0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0122   -1.4003    0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -1.9319   -0.1315 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2429   -0.9856   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3353    0.1230    0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3198    4.1316    0.4713 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9604    4.1992   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926    2.9645    0.2497 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645   -3.9693   -0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605   -2.0841   -1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982   -3.4185   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437   -2.4232   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8955    0.0213   -0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9088    1.4410    0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291    2.7826    0.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9154   -1.7094    1.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -2.7140    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9025   -0.4994   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2118   -1.4664   -0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107    0.8283    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5599   -0.3044    1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5388    5.0620    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    4.1989   -1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
 20 21  1  0
 15  2  1  0
  8  3  1  0
 14  9  1  0
 21 10  1  0
 18 13  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 12 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -2.113   3.775   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.603   4.228   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.150   3.020   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.603   1.811   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.303   0.301   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.509  -0.754   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.207  -2.264   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -2.264  -3.322   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -3.775  -2.869   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.077  -1.358   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.869  -0.301   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.322   1.207   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.113   2.264   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.869  -2.113   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.077  -1.207   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.775   0.301   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.264   0.754   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.056  -0.152   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.358  -1.660   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.301  -2.717   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       0.603  -4.228   0.000  0.00  0.00           O+0
CONECT    1    2   13                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6   18                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8   20                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13    1    4   12                                                  
CONECT   14   15   19                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18    5   17   19                                                  
CONECT   19   14   18   20                                                  
CONECT   20    7   19   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   50    0
END

COMPND    HMDB0302139
HETATM    1  O1  UNL     1       0.102  -3.495   0.023  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.068  -2.129  -0.321  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.389  -1.512  -0.172  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.534  -2.334  -0.300  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.779  -1.768  -0.265  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.897  -0.408  -0.107  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.791   0.412   0.022  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.532  -0.150  -0.010  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.353   0.662   0.235  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.512   2.032   0.290  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.672   2.767   0.434  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.914   2.194   0.517  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.038   0.826   0.460  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.886   0.058   0.319  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.012  -1.400   0.364  1.00  0.00           C  
HETATM   16  N1  UNL     1      -2.270  -1.932  -0.132  1.00  0.00           N  
HETATM   17  C15 UNL     1      -3.243  -0.986  -0.514  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.335   0.123   0.535  1.00  0.00           C  
HETATM   19  O2  UNL     1      -0.320   4.132   0.471  1.00  0.00           O  
HETATM   20  C17 UNL     1       0.960   4.199  -0.182  1.00  0.00           C  
HETATM   21  O3  UNL     1       1.493   2.964   0.250  1.00  0.00           O  
HETATM   22  H1  UNL     1       0.465  -3.969  -0.766  1.00  0.00           H  
HETATM   23  H2  UNL     1      -0.160  -2.084  -1.434  1.00  0.00           H  
HETATM   24  H3  UNL     1       2.398  -3.418  -0.425  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.644  -2.423  -0.366  1.00  0.00           H  
HETATM   26  H5  UNL     1       4.895   0.021  -0.084  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.909   1.441   0.143  1.00  0.00           H  
HETATM   28  H7  UNL     1      -2.829   2.783   0.628  1.00  0.00           H  
HETATM   29  H8  UNL     1      -0.915  -1.709   1.477  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.619  -2.714   0.464  1.00  0.00           H  
HETATM   31  H10 UNL     1      -2.902  -0.499  -1.474  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.212  -1.466  -0.648  1.00  0.00           H  
HETATM   33  H12 UNL     1      -4.111   0.828   0.184  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.560  -0.304   1.515  1.00  0.00           H  
HETATM   35  H14 UNL     1       1.539   5.062   0.143  1.00  0.00           H  
HETATM   36  H15 UNL     1       0.742   4.199  -1.274  1.00  0.00           H  
CONECT    1    2   22
CONECT    2    3   15   23
CONECT    3    4    4    8
CONECT    4    5   24
CONECT    5    6    6   25
CONECT    6    7   26
CONECT    7    8    8   27
CONECT    8    9
CONECT    9   10   10   14
CONECT   10   11   21
CONECT   11   12   12   19
CONECT   12   13   28
CONECT   13   14   14   18
CONECT   14   15
CONECT   15   16   29
CONECT   16   17   30
CONECT   17   18   31   32
CONECT   18   33   34
CONECT   19   20
CONECT   20   21   35   36
END

HMDB0302139
     RDKit          3D
(-)-Norushinsunine
 36 40  0  0  0  0  0  0  0  0999 V2000
    0.1021   -3.4947    0.0229 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0681   -2.1293   -0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3888   -1.5119   -0.1721 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5337   -2.3342   -0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7786   -1.7683   -0.2655 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8967   -0.4079   -0.1070 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7915    0.4124    0.0215 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5316   -0.1503   -0.0103 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3528    0.6620    0.2348 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5123    2.0318    0.2903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6720    2.7668    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9145    2.1938    0.5170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0381    0.8256    0.4598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8862    0.0581    0.3185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0122   -1.4003    0.3637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2700   -1.9319   -0.1315 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2429   -0.9856   -0.5145 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3353    0.1230    0.5354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3198    4.1316    0.4713 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9604    4.1992   -0.1824 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4926    2.9645    0.2497 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4645   -3.9693   -0.7660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1605   -2.0841   -1.4341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3982   -3.4185   -0.4251 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6437   -2.4232   -0.3662 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8955    0.0213   -0.0838 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9088    1.4410    0.1432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8291    2.7826    0.6284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9154   -1.7094    1.4772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6193   -2.7140    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9025   -0.4994   -1.4740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2118   -1.4664   -0.6476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1107    0.8283    0.1843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5599   -0.3044    1.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5388    5.0620    0.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    4.1989   -1.2740 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
 20 21  1  0
 15  2  1  0
  8  3  1  0
 14  9  1  0
 21 10  1  0
 18 13  1  0
  1 22  1  0
  2 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
 12 28  1  0
 15 29  1  0
 16 30  1  0
 17 31  1  0
 17 32  1  0
 18 33  1  0
 18 34  1  0
 20 35  1  0
 20 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₇H₁₅NO₃

Average Molecular Weight

281.3059

Monoisotopic Molecular Weight

281.105193351

IUPAC Name

3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaen-13-ol

Traditional Name

3,5-dioxa-11-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14(19),15,17-hexaen-13-ol

CAS Registry Number

Not Available

SMILES

OC1C2NCCC3=CC4=C(OCO4)C(C4=C1C=CC=C4)=C23

InChI Identifier

InChI=1S/C17H15NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-4,7,15-16,18-19H,5-6,8H2

InChI Key

CKIYSMRPIBQTHQ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxy-7-aporphines. These are aporphines containing a hydroxyl group at the 7-position.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Hydroxy-7-aporphines

Direct Parent

Hydroxy-7-aporphines

Alternative Parents

Substituents

Hydroxy-7-aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Aralkylamine
Benzenoid
1,2-aminoalcohol
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Secondary aliphatic amine
Acetal
Secondary amine
Organic oxygen compound
Amine
Organic nitrogen compound
Alcohol
Organonitrogen compound
Organooxygen compound
Organopnictogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Not Available

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	1.14	ALOGPS
logP	2.02	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.82	ChemAxon
pKa (Strongest Basic)	8.86	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	50.72 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	77.71 m³·mol⁻¹	ChemAxon
Polarizability	29.83 Å³	ChemAxon
Number of Rings	5	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
AllCCS	[M+H]+	165.888	32859911
AllCCS	[M+H-H2O]+	162.218	32859911
AllCCS	[M+Na]+	170.276	32859911
AllCCS	[M+NH4]+	169.296	32859911
AllCCS	[M-H]-	171.397	32859911
AllCCS	[M+Na-2H]-	170.444	32859911
AllCCS	[M+HCOO]-	169.526	32859911
DeepCCS	[M-2H]-	198.986	30932474
DeepCCS	[M+Na]+	174.551	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Norushinsunine,2TMS,isomer #1	C[Si](C)(C)OC1C2=CC=CC=C2C2=C3OCOC3=CC3=C2C1N([Si](C)(C)C)CC3	2631.8	Semi standard non polar	33892256
(-)-Norushinsunine,2TMS,isomer #1	C[Si](C)(C)OC1C2=CC=CC=C2C2=C3OCOC3=CC3=C2C1N([Si](C)(C)C)CC3	2660.1	Standard non polar	33892256
(-)-Norushinsunine,2TMS,isomer #1	C[Si](C)(C)OC1C2=CC=CC=C2C2=C3OCOC3=CC3=C2C1N([Si](C)(C)C)CC3	3279.9	Standard polar	33892256
(-)-Norushinsunine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C2=CC=CC=C2C2=C3OCOC3=CC3=C2C1N([Si](C)(C)C(C)(C)C)CC3	3048.5	Semi standard non polar	33892256
(-)-Norushinsunine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C2=CC=CC=C2C2=C3OCOC3=CC3=C2C1N([Si](C)(C)C(C)(C)C)CC3	3110.3	Standard non polar	33892256
(-)-Norushinsunine,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C2=CC=CC=C2C2=C3OCOC3=CC3=C2C1N([Si](C)(C)C(C)(C)C)CC3	3527.2	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Norushinsunine 10V, Positive-QTOF	splash10-03e9-0090000000-37e6b842589bcb0a9ad5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Norushinsunine 20V, Positive-QTOF	splash10-03di-0090000000-eff1c3da0c904505fe2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Norushinsunine 40V, Positive-QTOF	splash10-001i-2790000000-db33095b516fa8835e84	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Norushinsunine 10V, Negative-QTOF	splash10-001i-0090000000-2d8bb661bca93a062ccd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Norushinsunine 20V, Negative-QTOF	splash10-01q9-0090000000-819801ca69d129d77e23	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Norushinsunine 40V, Negative-QTOF	splash10-06sl-2190000000-6a7fe41f9adfca0f8b93	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Norushinsunine 10V, Negative-QTOF	splash10-001i-0090000000-cd1939612c9ef5597ee0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Norushinsunine 20V, Negative-QTOF	splash10-001i-0090000000-712beeee8df97ec94593	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Norushinsunine 40V, Negative-QTOF	splash10-01ta-0090000000-ead0133d2345b2d48a49	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Norushinsunine 10V, Positive-QTOF	splash10-001i-0090000000-3b4cac44e39678d48174	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Norushinsunine 20V, Positive-QTOF	splash10-001i-0090000000-cbdce8f67132e70cc8b6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Norushinsunine 40V, Positive-QTOF	splash10-0udi-0090000000-a46810c466cd3b43caa1	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB002073

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5319820

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

Not Available

Showing metabocard for (-)-Norushinsunine (HMDB0302139)

MOL for HMDB0302139 ((-)-Norushinsunine)

3D MOL for HMDB0302139 ((-)-Norushinsunine)

3D SDF for HMDB0302139 ((-)-Norushinsunine)

3D-SDF for HMDB0302139 ((-)-Norushinsunine)

PDB for HMDB0302139 ((-)-Norushinsunine)

3D PDB for HMDB0302139 ((-)-Norushinsunine)

SMILES for HMDB0302139 ((-)-Norushinsunine)

INCHI for HMDB0302139 ((-)-Norushinsunine)

Structure for HMDB0302139 ((-)-Norushinsunine)

3D Structure for HMDB0302139 ((-)-Norushinsunine)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra