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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:20:10 UTC

Update Date

2022-03-07 02:54:07 UTC

HMDB ID

HMDB0034489

Secondary Accession Numbers

HMDB34489

Metabolite Identification

Common Name

(+)-Norushinsunine N-oxide

Description

(+)-Norushinsunine N-oxide, also known as 1,2-dehydro-a-cyperone or 1,4,11-eudesmatrien-3-one, belongs to the class of organic compounds known as hydroxy-7-aporphines. These are aporphines containing a hydroxyl group at the 7-position. Based on a literature review a significant number of articles have been published on (+)-Norushinsunine N-oxide.

Structure

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

HMDB0034489
     RDKit          3D
(+)-Norushinsunine N-oxide
 40 44  0  0  0  0  0  0  0  0999 V2000
   -3.2634   -1.6707    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3422   -0.6303   -0.3723 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.9453   -0.9797   -1.6264 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.0671    0.5936   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901    1.6674    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1138    1.8218    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5151    3.0152    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8473    3.0443   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842    1.8838   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9591    0.6863    0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054    0.6279    0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1952   -0.5745    0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4429   -1.8406    0.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9378   -2.7515   -0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105   -1.7333    0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7091   -2.9556    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571   -2.9961    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7091   -1.8148   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0824   -0.5872   -0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7067   -0.5736    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8710    2.2444   -0.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0257    3.6600   -0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6924    4.1392   -0.4805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3290   -1.2960    0.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2616   -2.5481   -0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722   -1.9425    1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1638    0.4783   -0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003    1.0564   -1.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201    1.3058    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1443    2.5799    0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0956    3.9228    0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -0.4354    1.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5296   -2.3883    1.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7619   -3.6623   -0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1707   -3.8802    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676   -3.9645    0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804   -1.8296   -0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6612    0.2945   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5402    3.9755    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5556    4.0574   -1.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9 21  1  0
 21 22  1  0
 22 23  1  0
 12  2  1  0
 20 15  1  0
 11  6  1  0
 23  8  1  0
 20 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  7 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 22 39  1  0
 22 40  1  0
M  CHG  2   2   1   3  -1
M  END


  Mrv0541 05061307502D          

 23 27  0  0  0  0            999 V2000
    1.9592    3.1070    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    2.4750    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
    0.7145    2.0625    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
    3.1354   -1.3057    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    2.1434    1.2375    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
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    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
    1.4289    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8986    3.1070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3149   -1.2195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4710   -0.5520    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
 10  6  1  0  0  0  0
 10  8  2  0  0  0  0
 11  4  2  0  0  0  0
 12  5  2  0  0  0  0
 12 11  1  0  0  0  0
 13  8  1  0  0  0  0
 14 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  2  0  0  0  0
 16 14  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  1  0  0  0  0
 18 13  2  0  0  0  0
 18 15  1  0  0  0  0
 19  1  1  0  0  0  0
 19  7  1  0  0  0  0
 19 16  1  0  0  0  0
 20 17  1  0  0  0  0
 21 19  2  0  0  0  0
 22  9  1  0  0  0  0
 22 13  1  0  0  0  0
 23  9  1  0  0  0  0
 23 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034489

> <DATABASE_NAME>
hmdb

> <SMILES>
CN1(=O)CCC2=CC3=C(OCO3)C3=C2C1C(O)C1=CC=CC=C31

> <INCHI_IDENTIFIER>
InChI=1S/C18H17NO4/c1-19(21)7-6-10-8-13-18(23-9-22-13)15-11-4-2-3-5-12(11)17(20)16(19)14(10)15/h2-5,8,16-17,20H,6-7,9H2,1H3

> <INCHI_KEY>
PQQSHMZUVWGXSV-UHFFFAOYSA-N

> <FORMULA>
C18H17NO4

> <MOLECULAR_WEIGHT>
311.3319

> <EXACT_MASS>
311.115758037

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.50571348513683

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
13-hydroxy-11-methyl-3,5-dioxa-11λ⁵-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-one

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
1.281274165

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.50480206292192

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.231753448081836

> <JCHEM_PKA_STRONGEST_BASIC>
0.8830118597058808

> <JCHEM_POLAR_SURFACE_AREA>
65.57000000000001

> <JCHEM_REFRACTIVITY>
85.04559999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.78e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-hydroxy-11-methyl-3,5-dioxa-11λ⁵-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034489
     RDKit          3D
(+)-Norushinsunine N-oxide
 40 44  0  0  0  0  0  0  0  0999 V2000
   -3.2634   -1.6707    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3422   -0.6303   -0.3723 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.9453   -0.9797   -1.6264 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.0671    0.5936   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901    1.6674    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1138    1.8218    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5151    3.0152    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8473    3.0443   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842    1.8838   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9591    0.6863    0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054    0.6279    0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1952   -0.5745    0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4429   -1.8406    0.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9378   -2.7515   -0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105   -1.7333    0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7091   -2.9556    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571   -2.9961    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7091   -1.8148   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0824   -0.5872   -0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7067   -0.5736    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8710    2.2444   -0.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0257    3.6600   -0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6924    4.1392   -0.4805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3290   -1.2960    0.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2616   -2.5481   -0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722   -1.9425    1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1638    0.4783   -0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003    1.0564   -1.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201    1.3058    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1443    2.5799    0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0956    3.9228    0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -0.4354    1.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5296   -2.3883    1.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7619   -3.6623   -0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1707   -3.8802    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676   -3.9645    0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804   -1.8296   -0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6612    0.2945   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5402    3.9755    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5556    4.0574   -1.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9 21  1  0
 21 22  1  0
 22 23  1  0
 12  2  1  0
 20 15  1  0
 11  6  1  0
 23  8  1  0
 20 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  7 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 22 39  1  0
 22 40  1  0
M  CHG  2   2   1   3  -1
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       3.657   5.800   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   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.853  -2.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   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       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -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       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       2.667   4.620   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0       5.335   6.160   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.677   5.800   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       4.321  -2.276   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       6.479  -1.030   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   12                                                       
CONECT    6    7   10                                                       
CONECT    7    6   19                                                       
CONECT    8   10   13                                                       
CONECT    9   22   23                                                       
CONECT   10    6    8   14                                                  
CONECT   11    4   12   15                                                  
CONECT   12    5   11   17                                                  
CONECT   13    8   18   22                                                  
CONECT   14   10   15   16                                                  
CONECT   15   11   14   18                                                  
CONECT   16   14   17   19                                                  
CONECT   17   12   16   20                                                  
CONECT   18   13   15   23                                                  
CONECT   19    1    7   16   21                                             
CONECT   20   17                                                            
CONECT   21   19                                                            
CONECT   22    9   13                                                       
CONECT   23    9   18                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   54    0
END

COMPND    HMDB0034489
HETATM    1  C1  UNL     1      -3.263  -1.671   0.078  1.00  0.00           C  
HETATM    2  N1  UNL     1      -2.342  -0.630  -0.372  1.00  0.00           N1+
HETATM    3  O1  UNL     1      -1.945  -0.980  -1.626  1.00  0.00           O1-
HETATM    4  C2  UNL     1      -3.067   0.594  -0.457  1.00  0.00           C  
HETATM    5  C3  UNL     1      -2.590   1.667   0.501  1.00  0.00           C  
HETATM    6  C4  UNL     1      -1.114   1.822   0.238  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.515   3.015   0.010  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.847   3.044  -0.222  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.584   1.884  -0.222  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.959   0.686   0.011  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.405   0.628   0.247  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.195  -0.574   0.514  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.443  -1.841   0.490  1.00  0.00           C  
HETATM   14  O2  UNL     1      -0.938  -2.752  -0.453  1.00  0.00           O  
HETATM   15  C12 UNL     1       1.011  -1.733   0.246  1.00  0.00           C  
HETATM   16  C13 UNL     1       1.709  -2.956   0.258  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.057  -2.996   0.042  1.00  0.00           C  
HETATM   18  C15 UNL     1       3.709  -1.815  -0.187  1.00  0.00           C  
HETATM   19  C16 UNL     1       3.082  -0.587  -0.211  1.00  0.00           C  
HETATM   20  C17 UNL     1       1.707  -0.574   0.013  1.00  0.00           C  
HETATM   21  O3  UNL     1       2.871   2.244  -0.476  1.00  0.00           O  
HETATM   22  C18 UNL     1       3.026   3.660  -0.413  1.00  0.00           C  
HETATM   23  O4  UNL     1       1.692   4.139  -0.480  1.00  0.00           O  
HETATM   24  H1  UNL     1      -4.329  -1.296   0.057  1.00  0.00           H  
HETATM   25  H2  UNL     1      -3.262  -2.548  -0.613  1.00  0.00           H  
HETATM   26  H3  UNL     1      -3.072  -1.942   1.127  1.00  0.00           H  
HETATM   27  H4  UNL     1      -4.164   0.478  -0.274  1.00  0.00           H  
HETATM   28  H5  UNL     1      -3.000   1.056  -1.486  1.00  0.00           H  
HETATM   29  H6  UNL     1      -2.720   1.306   1.549  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.144   2.580   0.283  1.00  0.00           H  
HETATM   31  H8  UNL     1      -1.096   3.923   0.010  1.00  0.00           H  
HETATM   32  H9  UNL     1      -1.633  -0.435   1.548  1.00  0.00           H  
HETATM   33  H10 UNL     1      -0.530  -2.388   1.477  1.00  0.00           H  
HETATM   34  H11 UNL     1      -0.762  -3.662  -0.163  1.00  0.00           H  
HETATM   35  H12 UNL     1       1.171  -3.880   0.442  1.00  0.00           H  
HETATM   36  H13 UNL     1       3.568  -3.964   0.058  1.00  0.00           H  
HETATM   37  H14 UNL     1       4.780  -1.830  -0.361  1.00  0.00           H  
HETATM   38  H15 UNL     1       3.661   0.294  -0.397  1.00  0.00           H  
HETATM   39  H16 UNL     1       3.540   3.976   0.523  1.00  0.00           H  
HETATM   40  H17 UNL     1       3.556   4.057  -1.307  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3    4   12
CONECT    4    5   27   28
CONECT    5    6   29   30
CONECT    6    7    7   11
CONECT    7    8   31
CONECT    8    9    9   23
CONECT    9   10   21
CONECT   10   11   11   20
CONECT   11   12
CONECT   12   13   32
CONECT   13   14   15   33
CONECT   14   34
CONECT   15   16   16   20
CONECT   16   17   35
CONECT   17   18   18   36
CONECT   18   19   37
CONECT   19   20   20   38
CONECT   21   22
CONECT   22   23   39   40
END

HMDB0034489
     RDKit          3D
(+)-Norushinsunine N-oxide
 40 44  0  0  0  0  0  0  0  0999 V2000
   -3.2634   -1.6707    0.0780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3422   -0.6303   -0.3723 N   0  0  0  0  0  4  0  0  0  0  0  0
   -1.9453   -0.9797   -1.6264 O   0  0  0  0  0  1  0  0  0  0  0  0
   -3.0671    0.5936   -0.4572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5901    1.6674    0.5006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1138    1.8218    0.2379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5151    3.0152    0.0099 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8473    3.0443   -0.2218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5842    1.8838   -0.2217 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9591    0.6863    0.0111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4054    0.6279    0.2466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1952   -0.5745    0.5135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4429   -1.8406    0.4902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9378   -2.7515   -0.4532 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105   -1.7333    0.2464 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7091   -2.9556    0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0571   -2.9961    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7091   -1.8148   -0.1869 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0824   -0.5872   -0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7067   -0.5736    0.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8710    2.2444   -0.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0257    3.6600   -0.4133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6924    4.1392   -0.4805 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3290   -1.2960    0.0569 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2616   -2.5481   -0.6129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0722   -1.9425    1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1638    0.4783   -0.2739 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003    1.0564   -1.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7201    1.3058    1.5487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1443    2.5799    0.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0956    3.9228    0.0104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6333   -0.4354    1.5479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5296   -2.3883    1.4770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7619   -3.6623   -0.1630 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1707   -3.8802    0.4422 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676   -3.9645    0.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7804   -1.8296   -0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6612    0.2945   -0.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5402    3.9755    0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5556    4.0574   -1.3075 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
  9 21  1  0
 21 22  1  0
 22 23  1  0
 12  2  1  0
 20 15  1  0
 11  6  1  0
 23  8  1  0
 20 10  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  4 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  7 31  1  0
 12 32  1  0
 13 33  1  0
 14 34  1  0
 16 35  1  0
 17 36  1  0
 18 37  1  0
 19 38  1  0
 22 39  1  0
 22 40  1  0
M  CHG  2   2   1   3  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2-Dehydro-a-cyperone	HMDB
1,2-Dehydro-α-cyperone	HMDB
(+)-Eudesma-1,4,11-trien-3-one	HMDB
(4AS-cis)-5,6,7,8-tetrahydro-1,4a-dimethyl-7-(1-methylethenyl)-2(4ah)-naphthalenone	HMDB
1,4,11-Eudesmatrien-3-one	HMDB
1,4,11-Selinatrien-3-one	HMDB

Chemical Formula

C₁₈H₁₇NO₄

Average Molecular Weight

311.3319

Monoisotopic Molecular Weight

311.115758037

IUPAC Name

13-hydroxy-11-methyl-3,5-dioxa-11λ⁵-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-one

Traditional Name

13-hydroxy-11-methyl-3,5-dioxa-11λ⁵-azapentacyclo[10.7.1.0²,⁶.0⁸,²⁰.0¹⁴,¹⁹]icosa-1(20),2(6),7,14,16,18-hexaen-11-one

CAS Registry Number

Not Available

SMILES

CN1(=O)CCC2=CC3=C(OCO3)C3=C2C1C(O)C1=CC=CC=C31

InChI Identifier

InChI=1S/C18H17NO4/c1-19(21)7-6-10-8-13-18(23-9-22-13)15-11-4-2-3-5-12(11)17(20)16(19)14(10)15/h2-5,8,16-17,20H,6-7,9H2,1H3

InChI Key

PQQSHMZUVWGXSV-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
Benzenoid
Trialkyl amine oxide
Secondary alcohol
Oxacycle
Azacycle
Organoheterocyclic compound
Trisubstituted n-oxide
N-oxide
Acetal
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Organic zwitterion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0034489)
Cytoplasm (HMDB: HMDB0034489)

Source

Exogenous

Exogenous (HMDB: HMDB0034489)

Food

Food (HMDB: HMDB0034489)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0034489)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	177 - 179 °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	0.088 g/L	ALOGPS
logP	0.4	ALOGPS
logP	1.28	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	13.23	ChemAxon
pKa (Strongest Basic)	0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	65.57 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	85.05 m³·mol⁻¹	ChemAxon
Polarizability	32.51 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
DarkChem	[M+H]+	166.188	31661259
DarkChem	[M-H]-	165.61	31661259
DeepCCS	[M-2H]-	198.021	30932474
DeepCCS	[M+Na]+	173.248	30932474
AllCCS	[M+H]+	171.7	32859911
AllCCS	[M+H-H2O]+	168.3	32859911
AllCCS	[M+NH4]+	174.9	32859911
AllCCS	[M+Na]+	175.8	32859911
AllCCS	[M-H]-	178.6	32859911
AllCCS	[M+Na-2H]-	177.8	32859911
AllCCS	[M+HCOO]-	177.0	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.47 minutes	32390414
Predicted by Siyang on May 30, 2022	10.3351 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.9 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	55.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1339.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	220.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	157.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	177.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	90.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	316.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	354.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	428.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	843.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	259.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1237.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	255.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	401.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	344.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	15.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-Norushinsunine N-oxide	CN1(=O)CCC2=CC3=C(OCO3)C3=C2C1C(O)C1=CC=CC=C31	3588.9	Standard polar	33892256
(+)-Norushinsunine N-oxide	CN1(=O)CCC2=CC3=C(OCO3)C3=C2C1C(O)C1=CC=CC=C31	2481.1	Standard non polar	33892256
(+)-Norushinsunine N-oxide	CN1(=O)CCC2=CC3=C(OCO3)C3=C2C1C(O)C1=CC=CC=C31	2808.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-Norushinsunine N-oxide,1TMS,isomer #1	C[N+]1([O-])CCC2=CC3=C(OCO3)C3=C2C1C(O[Si](C)(C)C)C1=CC=CC=C13	2657.6	Semi standard non polar	33892256
(+)-Norushinsunine N-oxide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C2=CC=CC=C2C2=C3OCOC3=CC3=C2C1[N+](C)([O-])CC3	2904.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Norushinsunine N-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0017-0090000000-28ec1c65a82594597b1f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Norushinsunine N-oxide GC-MS (1 TMS) - 70eV, Positive	splash10-00xr-4039000000-47d9a05065c9cb9a1b80	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Norushinsunine N-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-Norushinsunine N-oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 10V, Positive-QTOF	splash10-03di-0029000000-b20de51f96980777ea97	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 20V, Positive-QTOF	splash10-03dl-0095000000-9558c50cea58ed1eb01c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 40V, Positive-QTOF	splash10-0ik9-0390000000-17f980b55123a731b792	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 10V, Negative-QTOF	splash10-03di-0009000000-5f478af9fe23ca0c0a99	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 20V, Negative-QTOF	splash10-03di-0009000000-0ca7b2da4155ee2ac2de	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 40V, Negative-QTOF	splash10-03di-8069000000-5a2749c549d162cffb6f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 10V, Positive-QTOF	splash10-03di-0009000000-4631b5d1b4d93faf70b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 20V, Positive-QTOF	splash10-01ox-0095000000-3e2ccf94088105534dcc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 40V, Positive-QTOF	splash10-0309-0090000000-ee36a9fef69537f49ce3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 10V, Negative-QTOF	splash10-03di-0009000000-43e89ef889a2eb4f124e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 20V, Negative-QTOF	splash10-03di-0009000000-43e89ef889a2eb4f124e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Norushinsunine N-oxide 40V, Negative-QTOF	splash10-03di-0009000000-43e89ef889a2eb4f124e	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB012978

KNApSAcK ID

C00012761

Chemspider ID

35013723

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13891870

PDB ID

Not Available

ChEBI ID

174973

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 (+)-Norushinsunine N-oxide (HMDB0034489)

MOL for HMDB0034489 ((+)-Norushinsunine N-oxide)

3D MOL for HMDB0034489 ((+)-Norushinsunine N-oxide)

3D SDF for HMDB0034489 ((+)-Norushinsunine N-oxide)

3D-SDF for HMDB0034489 ((+)-Norushinsunine N-oxide)

PDB for HMDB0034489 ((+)-Norushinsunine N-oxide)

3D PDB for HMDB0034489 ((+)-Norushinsunine N-oxide)

SMILES for HMDB0034489 ((+)-Norushinsunine N-oxide)

INCHI for HMDB0034489 ((+)-Norushinsunine N-oxide)

Structure for HMDB0034489 ((+)-Norushinsunine N-oxide)

3D Structure for HMDB0034489 ((+)-Norushinsunine N-oxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra