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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 23:25:58 UTC

Update Date

2022-09-22 18:35:11 UTC

HMDB ID

HMDB0038149

Secondary Accession Numbers

HMDB38149

Metabolite Identification

Common Name

Nepetaside

Description

Nepetaside belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone. Based on a literature review a small amount of articles have been published on Nepetaside.

Structure

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

HMDB0038149
     RDKit          3D
Nepetaside
 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.5393   -0.4319   -1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1589   -1.1694   -0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2476   -0.8905    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9425    0.1335    1.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726    0.9883    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7275    1.9118    2.4190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9085    0.7644    0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844    1.0418    0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0647    2.3240    0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6560   -0.1127    0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414    0.3180   -0.5258 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6082   -0.1297   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941    0.9412    0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7370    0.8202   -0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4337    1.6975    0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1195    1.2959    2.2630 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3104   -0.5497    0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5767   -0.5657   -0.5269 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778   -1.6105   -0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2230   -2.3425   -1.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2614   -0.9418   -1.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7709   -0.2036   -2.3419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6614   -0.9039   -0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8692   -0.7651    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1060    0.4931   -1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2343   -1.0231   -2.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6918   -0.1419   -2.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1480   -2.2622   -0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4277   -1.8171    1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2201   -0.6671    0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300    1.2230   -0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3045    1.1958    1.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4679    2.1245   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427    2.9430   -0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4317    2.9677    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279   -0.7678    1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5114   -0.7753    0.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0235    1.2817   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1069    2.7559    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5391    1.6932    0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430    2.0605    2.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4699   -0.7812    1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3047   -0.6859    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1128   -2.2961    0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2907   -3.3016   -1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -1.7996   -1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3911   -0.4818   -3.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3198   -1.9527   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7644   -0.3958   -1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360   -1.2088    1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 10 23  1  0
 23 24  1  0
 24  2  1  0
 24  7  1  0
 21 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
M  END


  Mrv0541 05061310152D          

 24 26  0  0  0  0            999 V2000
    3.2789    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249   -1.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -2.4454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7676   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574   -3.1599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801   -2.4454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0051   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1801    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699   -1.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  8  6  1  0  0  0  0
  9  3  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 11  1  0  0  0  0
 16 14  1  0  0  0  0
 17  4  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 14  1  0  0  0  0
 21 15  2  0  0  0  0
 22  5  1  0  0  0  0
 22 15  1  0  0  0  0
 23  9  1  0  0  0  0
 23 16  1  0  0  0  0
 24 10  1  0  0  0  0
 24 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038149

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C(CC2C1C(=O)OCC2C)OC1OC(CO)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O8/c1-6-5-22-15(21)11-7(2)9(3-8(6)11)23-16-14(20)13(19)12(18)10(4-17)24-16/h6-14,16-20H,3-5H2,1-2H3

> <INCHI_KEY>
CUIDBUWFCFYEPL-UHFFFAOYSA-N

> <FORMULA>
C16H26O8

> <MOLECULAR_WEIGHT>
346.3728

> <EXACT_MASS>
346.162767808

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
35.14612101004255

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4,7-dimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydrocyclopenta[c]pyran-1-one

> <ALOGPS_LOGP>
-1.03

> <JCHEM_LOGP>
-1.0226404123333337

> <ALOGPS_LOGS>
-1.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.200090334720134

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.210562078675087

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810835427867586

> <JCHEM_POLAR_SURFACE_AREA>
125.68000000000002

> <JCHEM_REFRACTIVITY>
79.857

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.26e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,7-dimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydro-3H-cyclopenta[c]pyran-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038149
     RDKit          3D
Nepetaside
 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.5393   -0.4319   -1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1589   -1.1694   -0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2476   -0.8905    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9425    0.1335    1.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726    0.9883    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7275    1.9118    2.4190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9085    0.7644    0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844    1.0418    0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0647    2.3240    0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6560   -0.1127    0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414    0.3180   -0.5258 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6082   -0.1297   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941    0.9412    0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7370    0.8202   -0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4337    1.6975    0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1195    1.2959    2.2630 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3104   -0.5497    0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5767   -0.5657   -0.5269 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778   -1.6105   -0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2230   -2.3425   -1.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2614   -0.9418   -1.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7709   -0.2036   -2.3419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6614   -0.9039   -0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8692   -0.7651    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1060    0.4931   -1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2343   -1.0231   -2.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6918   -0.1419   -2.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1480   -2.2622   -0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4277   -1.8171    1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2201   -0.6671    0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300    1.2230   -0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3045    1.1958    1.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4679    2.1245   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427    2.9430   -0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4317    2.9677    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279   -0.7678    1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5114   -0.7753    0.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0235    1.2817   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1069    2.7559    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5391    1.6932    0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430    2.0605    2.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4699   -0.7812    1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3047   -0.6859    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1128   -2.2961    0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2907   -3.3016   -1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -1.7996   -1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3911   -0.4818   -3.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3198   -1.9527   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7644   -0.3958   -1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360   -1.2088    1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 10 23  1  0
 23 24  1  0
 24  2  1  0
 24  7  1  0
 21 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.121   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.846  -1.941   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.877  -4.565   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.322  -0.476   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.107  -3.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.433  -3.231   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.203  -1.897   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.433  -0.564   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.107  -0.564   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.107  -5.898   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.203  -4.565   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -3.743  -1.897   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -2.203   0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.454   0.000   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       0.877   0.770   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       0.877  -1.897   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    8    9                                                       
CONECT    4   10   17                                                       
CONECT    5    6   22                                                       
CONECT    6    1    5    8                                                  
CONECT    7    2    9   11                                                  
CONECT    8    3    6   11                                                  
CONECT    9    3    7   23                                                  
CONECT   10    4   12   24                                                  
CONECT   11    7    8   15                                                  
CONECT   12   10   13   18                                                  
CONECT   13   12   14   19                                                  
CONECT   14   13   16   20                                                  
CONECT   15   11   21   22                                                  
CONECT   16   14   23   24                                                  
CONECT   17    4                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   14                                                            
CONECT   21   15                                                            
CONECT   22    5   15                                                       
CONECT   23    9   16                                                       
CONECT   24   10   16                                                       
MASTER        0    0    0    0    0    0    0    0   24    0   52    0
END

COMPND    HMDB0038149
HETATM    1  C1  UNL     1      -4.539  -0.432  -1.487  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.159  -1.169  -0.228  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.248  -0.891   0.792  1.00  0.00           C  
HETATM    4  O1  UNL     1      -4.942   0.134   1.691  1.00  0.00           O  
HETATM    5  C4  UNL     1      -3.873   0.988   1.609  1.00  0.00           C  
HETATM    6  O2  UNL     1      -3.728   1.912   2.419  1.00  0.00           O  
HETATM    7  C5  UNL     1      -2.908   0.764   0.525  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.484   1.042   0.865  1.00  0.00           C  
HETATM    9  C7  UNL     1      -1.065   2.324   0.180  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.656  -0.113   0.318  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.341   0.318  -0.526  1.00  0.00           O  
HETATM   12  C9  UNL     1       1.608  -0.130  -0.222  1.00  0.00           C  
HETATM   13  O4  UNL     1       2.394   0.941   0.123  1.00  0.00           O  
HETATM   14  C10 UNL     1       3.737   0.820  -0.079  1.00  0.00           C  
HETATM   15  C11 UNL     1       4.434   1.697   0.972  1.00  0.00           C  
HETATM   16  O5  UNL     1       4.119   1.296   2.263  1.00  0.00           O  
HETATM   17  C12 UNL     1       4.310  -0.550   0.067  1.00  0.00           C  
HETATM   18  O6  UNL     1       5.577  -0.566  -0.527  1.00  0.00           O  
HETATM   19  C13 UNL     1       3.478  -1.610  -0.614  1.00  0.00           C  
HETATM   20  O7  UNL     1       4.223  -2.342  -1.503  1.00  0.00           O  
HETATM   21  C14 UNL     1       2.261  -0.942  -1.276  1.00  0.00           C  
HETATM   22  O8  UNL     1       2.771  -0.204  -2.342  1.00  0.00           O  
HETATM   23  C15 UNL     1      -1.661  -0.904  -0.497  1.00  0.00           C  
HETATM   24  C16 UNL     1      -2.869  -0.765   0.350  1.00  0.00           C  
HETATM   25  H1  UNL     1      -5.106   0.493  -1.225  1.00  0.00           H  
HETATM   26  H2  UNL     1      -5.234  -1.023  -2.129  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.692  -0.142  -2.104  1.00  0.00           H  
HETATM   28  H4  UNL     1      -4.148  -2.262  -0.509  1.00  0.00           H  
HETATM   29  H5  UNL     1      -5.428  -1.817   1.387  1.00  0.00           H  
HETATM   30  H6  UNL     1      -6.220  -0.667   0.299  1.00  0.00           H  
HETATM   31  H7  UNL     1      -3.230   1.223  -0.434  1.00  0.00           H  
HETATM   32  H8  UNL     1      -1.305   1.196   1.946  1.00  0.00           H  
HETATM   33  H9  UNL     1      -0.468   2.124  -0.734  1.00  0.00           H  
HETATM   34  H10 UNL     1      -1.943   2.943  -0.099  1.00  0.00           H  
HETATM   35  H11 UNL     1      -0.432   2.968   0.848  1.00  0.00           H  
HETATM   36  H12 UNL     1      -0.328  -0.768   1.134  1.00  0.00           H  
HETATM   37  H13 UNL     1       1.511  -0.775   0.696  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.024   1.282  -1.061  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.107   2.756   0.853  1.00  0.00           H  
HETATM   40  H16 UNL     1       5.539   1.693   0.810  1.00  0.00           H  
HETATM   41  H17 UNL     1       3.843   2.061   2.841  1.00  0.00           H  
HETATM   42  H18 UNL     1       4.470  -0.781   1.154  1.00  0.00           H  
HETATM   43  H19 UNL     1       6.305  -0.686   0.145  1.00  0.00           H  
HETATM   44  H20 UNL     1       3.113  -2.296   0.196  1.00  0.00           H  
HETATM   45  H21 UNL     1       4.291  -3.302  -1.304  1.00  0.00           H  
HETATM   46  H22 UNL     1       1.638  -1.800  -1.633  1.00  0.00           H  
HETATM   47  H23 UNL     1       2.391  -0.482  -3.214  1.00  0.00           H  
HETATM   48  H24 UNL     1      -1.320  -1.953  -0.610  1.00  0.00           H  
HETATM   49  H25 UNL     1      -1.764  -0.396  -1.463  1.00  0.00           H  
HETATM   50  H26 UNL     1      -2.736  -1.209   1.339  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   24   28
CONECT    3    4   29   30
CONECT    4    5
CONECT    5    6    6    7
CONECT    7    8   24   31
CONECT    8    9   10   32
CONECT    9   33   34   35
CONECT   10   11   23   36
CONECT   11   12
CONECT   12   13   21   37
CONECT   13   14
CONECT   14   15   17   38
CONECT   15   16   39   40
CONECT   16   41
CONECT   17   18   19   42
CONECT   18   43
CONECT   19   20   21   44
CONECT   20   45
CONECT   21   22   46
CONECT   22   47
CONECT   23   24   48   49
CONECT   24   50
END

HMDB0038149
     RDKit          3D
Nepetaside
 50 52  0  0  0  0  0  0  0  0999 V2000
   -4.5393   -0.4319   -1.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1589   -1.1694   -0.2284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2476   -0.8905    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9425    0.1335    1.6906 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8726    0.9883    1.6090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7275    1.9118    2.4190 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9085    0.7644    0.5245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4844    1.0418    0.8651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0647    2.3240    0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6560   -0.1127    0.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3414    0.3180   -0.5258 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6082   -0.1297   -0.2221 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3941    0.9412    0.1235 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7370    0.8202   -0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4337    1.6975    0.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1195    1.2959    2.2630 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3104   -0.5497    0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5767   -0.5657   -0.5269 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4778   -1.6105   -0.6142 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2230   -2.3425   -1.5030 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2614   -0.9418   -1.2757 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7709   -0.2036   -2.3419 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6614   -0.9039   -0.4965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8692   -0.7651    0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1060    0.4931   -1.2250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2343   -1.0231   -2.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6918   -0.1419   -2.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1480   -2.2622   -0.5089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4277   -1.8171    1.3871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2201   -0.6671    0.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300    1.2230   -0.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3045    1.1958    1.9461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4679    2.1245   -0.7340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9427    2.9430   -0.0988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4317    2.9677    0.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3279   -0.7678    1.1340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5114   -0.7753    0.6958 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0235    1.2817   -1.0612 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1069    2.7559    0.8527 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5391    1.6932    0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8430    2.0605    2.8412 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4699   -0.7812    1.1535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3047   -0.6859    0.1449 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1128   -2.2961    0.1964 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2907   -3.3016   -1.3039 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381   -1.7996   -1.6329 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3911   -0.4818   -3.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3198   -1.9527   -0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7644   -0.3958   -1.4633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7360   -1.2088    1.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 10 23  1  0
 23 24  1  0
 24  2  1  0
 24  7  1  0
 21 12  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  7 31  1  0
  8 32  1  0
  9 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 12 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 17 42  1  0
 18 43  1  0
 19 44  1  0
 20 45  1  0
 21 46  1  0
 22 47  1  0
 23 48  1  0
 23 49  1  0
 24 50  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
(-)-Nepetaside	HMDB

Chemical Formula

C₁₆H₂₆O₈

Average Molecular Weight

346.3728

Monoisotopic Molecular Weight

346.162767808

IUPAC Name

4,7-dimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-octahydrocyclopenta[c]pyran-1-one

Traditional Name

4,7-dimethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-hexahydro-3H-cyclopenta[c]pyran-1-one

CAS Registry Number

114076-56-1

SMILES

CC1C(CC2C1C(=O)OCC2C)OC1OC(CO)C(O)C(O)C1O

InChI Identifier

InChI=1S/C16H26O8/c1-6-5-22-15(21)11-7(2)9(3-8(6)11)23-16-14(20)13(19)12(18)10(4-17)24-16/h6-14,16-20H,3-5H2,1-2H3

InChI Key

CUIDBUWFCFYEPL-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene glycosides. These are prenol lipids containing a carbohydrate moiety glycosidically bound to a terpene backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Terpene glycosides

Alternative Parents

Substituents

Terpene glycoside
Terpene lactone
Hexose monosaccharide
Glycosyl compound
Iridoid-skeleton
O-glycosyl compound
Bicyclic monoterpenoid
Monoterpenoid
Delta valerolactone
Delta_valerolactone
Monosaccharide
Oxane
Lactone
Secondary alcohol
Carboxylic acid ester
Polyol
Carboxylic acid derivative
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Alcohol
Organic oxide
Hydrocarbon derivative
Primary alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	204 - 205 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	128800 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	32.6 g/L	ALOGPS
logP	-1	ALOGPS
logP	-1	ChemAxon
logS	-1	ALOGPS
pKa (Strongest Acidic)	12.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	125.68 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	79.86 m³·mol⁻¹	ChemAxon
Polarizability	35.15 Å³	ChemAxon
Number of Rings	3	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
DarkChem	[M+H]+	180.087	31661259
DarkChem	[M-H]-	177.072	31661259
DeepCCS	[M+H]+	179.797	30932474
DeepCCS	[M-H]-	177.439	30932474
DeepCCS	[M-2H]-	210.959	30932474
DeepCCS	[M+Na]+	186.186	30932474
AllCCS	[M+H]+	181.7	32859911
AllCCS	[M+H-H2O]+	178.8	32859911
AllCCS	[M+NH4]+	184.3	32859911
AllCCS	[M+Na]+	185.1	32859911
AllCCS	[M-H]-	180.7	32859911
AllCCS	[M+Na-2H]-	180.8	32859911
AllCCS	[M+HCOO]-	181.0	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.	2.71 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2213 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.02 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	134.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1717.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	195.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	89.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	163.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	62.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	294.9 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	379.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	192.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	669.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	323.6 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	1087.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	224.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	237.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	349.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	243.8 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	248.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nepetaside	CC1C(CC2C1C(=O)OCC2C)OC1OC(CO)C(O)C(O)C1O	3547.5	Standard polar	33892256
Nepetaside	CC1C(CC2C1C(=O)OCC2C)OC1OC(CO)C(O)C(O)C1O	2705.6	Standard non polar	33892256
Nepetaside	CC1C(CC2C1C(=O)OCC2C)OC1OC(CO)C(O)C(O)C1O	2967.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nepetaside,1TMS,isomer #1	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O)CC12	2899.5	Semi standard non polar	33892256
Nepetaside,1TMS,isomer #2	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O)CC12	2905.1	Semi standard non polar	33892256
Nepetaside,1TMS,isomer #3	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O)CC12	2900.5	Semi standard non polar	33892256
Nepetaside,1TMS,isomer #4	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C)CC12	2900.4	Semi standard non polar	33892256
Nepetaside,2TMS,isomer #1	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O)CC12	2913.5	Semi standard non polar	33892256
Nepetaside,2TMS,isomer #2	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O)CC12	2917.9	Semi standard non polar	33892256
Nepetaside,2TMS,isomer #3	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O[Si](C)(C)C)CC12	2890.8	Semi standard non polar	33892256
Nepetaside,2TMS,isomer #4	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)CC12	2904.3	Semi standard non polar	33892256
Nepetaside,2TMS,isomer #5	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)CC12	2897.1	Semi standard non polar	33892256
Nepetaside,2TMS,isomer #6	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)CC12	2907.4	Semi standard non polar	33892256
Nepetaside,3TMS,isomer #1	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)CC12	2867.7	Semi standard non polar	33892256
Nepetaside,3TMS,isomer #2	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)CC12	2846.3	Semi standard non polar	33892256
Nepetaside,3TMS,isomer #3	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)CC12	2841.8	Semi standard non polar	33892256
Nepetaside,3TMS,isomer #4	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)CC12	2848.7	Semi standard non polar	33892256
Nepetaside,4TMS,isomer #1	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)CC12	2778.3	Semi standard non polar	33892256
Nepetaside,1TBDMS,isomer #1	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O)CC12	3146.3	Semi standard non polar	33892256
Nepetaside,1TBDMS,isomer #2	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)CC12	3146.1	Semi standard non polar	33892256
Nepetaside,1TBDMS,isomer #3	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)CC12	3146.0	Semi standard non polar	33892256
Nepetaside,1TBDMS,isomer #4	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)CC12	3135.2	Semi standard non polar	33892256
Nepetaside,2TBDMS,isomer #1	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)CC12	3352.5	Semi standard non polar	33892256
Nepetaside,2TBDMS,isomer #2	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)CC12	3359.9	Semi standard non polar	33892256
Nepetaside,2TBDMS,isomer #3	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)CC12	3331.8	Semi standard non polar	33892256
Nepetaside,2TBDMS,isomer #4	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)CC12	3338.5	Semi standard non polar	33892256
Nepetaside,2TBDMS,isomer #5	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)CC12	3336.5	Semi standard non polar	33892256
Nepetaside,2TBDMS,isomer #6	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)CC12	3342.9	Semi standard non polar	33892256
Nepetaside,3TBDMS,isomer #1	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)CC12	3531.2	Semi standard non polar	33892256
Nepetaside,3TBDMS,isomer #2	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)CC12	3524.3	Semi standard non polar	33892256
Nepetaside,3TBDMS,isomer #3	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)CC12	3518.8	Semi standard non polar	33892256
Nepetaside,3TBDMS,isomer #4	CC1COC(=O)C2C(C)C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)CC12	3513.8	Semi standard non polar	33892256
Nepetaside,4TBDMS,isomer #1	CC1COC(=O)C2C(C)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)CC12	3703.6	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 - Nepetaside GC-MS (Non-derivatized) - 70eV, Positive	splash10-08i9-7497000000-9a797b13d76058dadd6e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nepetaside GC-MS (4 TMS) - 70eV, Positive	splash10-00xr-2400169000-0cb3b94098a768406de7	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nepetaside GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nepetaside 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 - Nepetaside 10V, Positive-QTOF	splash10-00ks-0905000000-72d86d00be62ab907867	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetaside 20V, Positive-QTOF	splash10-00kr-0900000000-6180db475af51bf5a052	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetaside 40V, Positive-QTOF	splash10-014u-5900000000-1cf5b1299bdfc1b7f52f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetaside 10V, Negative-QTOF	splash10-000t-1809000000-709fa73380a7cfe5d130	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetaside 20V, Negative-QTOF	splash10-001i-1901000000-64d9d6f8cb4e75e4e9b2	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetaside 40V, Negative-QTOF	splash10-001r-3900000000-34b8e8b9828f8c3271e9	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetaside 10V, Negative-QTOF	splash10-0002-0009000000-49d51033851b8149b756	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetaside 20V, Negative-QTOF	splash10-052b-9537000000-36e41df86e064cacda9b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetaside 40V, Negative-QTOF	splash10-0a4i-9431000000-946c136ac5f6f7d2235b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetaside 10V, Positive-QTOF	splash10-00kb-0809000000-d0b521973fac096fe042	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetaside 20V, Positive-QTOF	splash10-014i-0901000000-f39870fca51caa284de0	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetaside 40V, Positive-QTOF	splash10-02t9-4900000000-3ca51e1d156883484c90	2021-09-25	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Asthma	33739820	details

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

FDB017377

KNApSAcK ID

C00010642

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

14020067

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1866041

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Nepetaside (HMDB0038149)

MOL for HMDB0038149 (Nepetaside)

3D MOL for HMDB0038149 (Nepetaside)

3D SDF for HMDB0038149 (Nepetaside)

3D-SDF for HMDB0038149 (Nepetaside)

PDB for HMDB0038149 (Nepetaside)

3D PDB for HMDB0038149 (Nepetaside)

SMILES for HMDB0038149 (Nepetaside)

INCHI for HMDB0038149 (Nepetaside)

Structure for HMDB0038149 (Nepetaside)

3D Structure for HMDB0038149 (Nepetaside)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra