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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:21:59 UTC

Update Date

2022-03-07 02:56:02 UTC

HMDB ID

HMDB0039014

Secondary Accession Numbers

HMDB39014

Metabolite Identification

Common Name

Nepetariaside

Description

Nepetariaside 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 Nepetariaside.

Structure

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

HMDB0039014
     RDKit          3D
Nepetariaside
 52 53  0  0  0  0  0  0  0  0999 V2000
   -2.0587    2.2031   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118    1.0253   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2512    1.2075    1.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865    0.2449    1.4339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7031    0.1206    0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501    0.5898    1.1764 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771    0.6270    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8802    1.7326   -0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985    1.6751   -1.3337 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3195   -0.6952   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5833   -1.0979    0.1962 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3463   -1.7789    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6439   -2.3708    1.3572 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9186   -1.3077    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2022   -2.0864    1.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6770   -0.2815   -0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -0.2354   -1.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6918   -0.2329   -1.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1062   -0.4656   -0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040    0.6455    0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -0.9097    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9209   -1.0936    1.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932   -0.8697    2.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1392   -1.5989    2.2375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6592    2.1059   -1.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944    3.1026   -0.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    2.4389    0.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774    1.2350   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2728    2.2274    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8114    1.3855    2.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5346    0.7933   -0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8086    0.9375    1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963    1.5986   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8740    2.7253   -0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7291    2.3674   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666   -0.5547   -1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2698   -0.8591   -0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3931   -2.5848   -0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5517   -2.7871    1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4191   -1.5112   -0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7126   -2.8869    1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264   -1.0021   -0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8821    0.7045   -2.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7874   -1.0491   -2.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0281   -1.0794   -2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1737    0.6586   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468   -1.3261   -0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3792    0.9745    1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8609    1.5381   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8822    0.4068    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639   -2.0186   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359   -2.5880    2.5053 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 14  5  1  0
 21 16  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
  5 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 24 52  1  0
M  END


  Mrv0541 02241215082D          

 24 25  0  0  0  0            999 V2000
   -1.3189    1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8239    1.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3189    0.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717   -0.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5668   -1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039    2.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438    1.5253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1438    0.7003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039    0.2881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5460    0.6182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8039   -0.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2467   -0.4532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3296    0.1232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1547   -0.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4017   -0.8661    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4017    1.3603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6496    0.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4739    0.3703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0510    1.0303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5460   -0.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7218   -0.3711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2268   -1.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4739   -1.8553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2160   -2.0203    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 17  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 21  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039014

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(COC1OC(CO)C(O)C(O)C1O)C1CCC(C)C1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H28O8/c1-7-3-4-9(11(7)15(21)22)8(2)6-23-16-14(20)13(19)12(18)10(5-17)24-16/h7-14,16-20H,3-6H2,1-2H3,(H,21,22)

> <INCHI_KEY>
NCBSGBLITRBNGW-UHFFFAOYSA-N

> <FORMULA>
C16H28O8

> <MOLECULAR_WEIGHT>
348.3887

> <EXACT_MASS>
348.178417872

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
35.67521868454952

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-5-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)cyclopentane-1-carboxylic acid

> <ALOGPS_LOGP>
-1.13

> <JCHEM_LOGP>
-0.3783467399999995

> <ALOGPS_LOGS>
-1.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.210973802512761

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.147411102257892

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810834118012046

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
81.75670000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-5-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)cyclopentane-1-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039014
     RDKit          3D
Nepetariaside
 52 53  0  0  0  0  0  0  0  0999 V2000
   -2.0587    2.2031   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118    1.0253   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2512    1.2075    1.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865    0.2449    1.4339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7031    0.1206    0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501    0.5898    1.1764 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771    0.6270    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8802    1.7326   -0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985    1.6751   -1.3337 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3195   -0.6952   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5833   -1.0979    0.1962 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3463   -1.7789    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6439   -2.3708    1.3572 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9186   -1.3077    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2022   -2.0864    1.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6770   -0.2815   -0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -0.2354   -1.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6918   -0.2329   -1.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1062   -0.4656   -0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040    0.6455    0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -0.9097    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9209   -1.0936    1.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932   -0.8697    2.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1392   -1.5989    2.2375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6592    2.1059   -1.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944    3.1026   -0.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    2.4389    0.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774    1.2350   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2728    2.2274    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8114    1.3855    2.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5346    0.7933   -0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8086    0.9375    1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963    1.5986   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8740    2.7253   -0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7291    2.3674   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666   -0.5547   -1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2698   -0.8591   -0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3931   -2.5848   -0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5517   -2.7871    1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4191   -1.5112   -0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7126   -2.8869    1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264   -1.0021   -0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8821    0.7045   -2.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7874   -1.0491   -2.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0281   -1.0794   -2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1737    0.6586   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468   -1.3261   -0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3792    0.9745    1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8609    1.5381   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8822    0.4068    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639   -2.0186   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359   -2.5880    2.5053 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 14  5  1  0
 21 16  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
  5 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 24 52  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  C   UNK     0      -2.462   3.308   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.538   2.078   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.462   0.846   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.001  -0.538   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.925  -1.923   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.234   3.771   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.002   2.847   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.002   1.307   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.234   0.538   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -6.619   1.154   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      -5.234  -1.001   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.461  -0.846   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.615   0.230   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.155  -0.077   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.617  -1.617   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.617   2.539   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       3.079   0.999   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.618   0.691   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.695   1.923   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.619  -1.001   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.081  -0.693   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.157  -1.923   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.618  -3.463   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       6.003  -3.771   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5   12                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    1    6    8                                                  
CONECT    8    3    7    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    4   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   17                                                  
CONECT   15   14   22                                                       
CONECT   16   17                                                            
CONECT   17   14   16   18                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18                                                            
CONECT   20   21                                                            
CONECT   21   18   20   22                                                  
CONECT   22   15   21   23                                                  
CONECT   23   22   24                                                       
CONECT   24   23                                                            
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0039014
HETATM    1  C1  UNL     1      -2.059   2.203  -0.132  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.112   1.025  -0.029  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.251   1.208   1.186  1.00  0.00           C  
HETATM    4  O1  UNL     1       0.687   0.245   1.434  1.00  0.00           O  
HETATM    5  C4  UNL     1       1.703   0.121   0.489  1.00  0.00           C  
HETATM    6  O2  UNL     1       2.850   0.590   1.176  1.00  0.00           O  
HETATM    7  C5  UNL     1       3.977   0.627   0.411  1.00  0.00           C  
HETATM    8  C6  UNL     1       3.880   1.733  -0.613  1.00  0.00           C  
HETATM    9  O3  UNL     1       5.098   1.675  -1.334  1.00  0.00           O  
HETATM   10  C7  UNL     1       4.319  -0.695  -0.222  1.00  0.00           C  
HETATM   11  O4  UNL     1       5.583  -1.098   0.196  1.00  0.00           O  
HETATM   12  C8  UNL     1       3.346  -1.779   0.130  1.00  0.00           C  
HETATM   13  O5  UNL     1       3.644  -2.371   1.357  1.00  0.00           O  
HETATM   14  C9  UNL     1       1.919  -1.308   0.190  1.00  0.00           C  
HETATM   15  O6  UNL     1       1.202  -2.086   1.104  1.00  0.00           O  
HETATM   16  C10 UNL     1      -1.677  -0.282  -0.315  1.00  0.00           C  
HETATM   17  C11 UNL     1      -2.195  -0.235  -1.784  1.00  0.00           C  
HETATM   18  C12 UNL     1      -3.692  -0.233  -1.703  1.00  0.00           C  
HETATM   19  C13 UNL     1      -4.106  -0.466  -0.284  1.00  0.00           C  
HETATM   20  C14 UNL     1      -4.804   0.646   0.384  1.00  0.00           C  
HETATM   21  C15 UNL     1      -2.796  -0.910   0.341  1.00  0.00           C  
HETATM   22  C16 UNL     1      -2.921  -1.094   1.763  1.00  0.00           C  
HETATM   23  O7  UNL     1      -2.093  -0.870   2.662  1.00  0.00           O  
HETATM   24  O8  UNL     1      -4.139  -1.599   2.238  1.00  0.00           O  
HETATM   25  H1  UNL     1      -2.659   2.106  -1.045  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.394   3.103  -0.316  1.00  0.00           H  
HETATM   27  H3  UNL     1      -2.584   2.439   0.788  1.00  0.00           H  
HETATM   28  H4  UNL     1      -0.377   1.235  -0.884  1.00  0.00           H  
HETATM   29  H5  UNL     1       0.273   2.227   1.026  1.00  0.00           H  
HETATM   30  H6  UNL     1      -0.811   1.386   2.125  1.00  0.00           H  
HETATM   31  H7  UNL     1       1.535   0.793  -0.377  1.00  0.00           H  
HETATM   32  H8  UNL     1       4.809   0.938   1.106  1.00  0.00           H  
HETATM   33  H9  UNL     1       3.096   1.599  -1.363  1.00  0.00           H  
HETATM   34  H10 UNL     1       3.874   2.725  -0.136  1.00  0.00           H  
HETATM   35  H11 UNL     1       5.729   2.367  -1.046  1.00  0.00           H  
HETATM   36  H12 UNL     1       4.367  -0.555  -1.318  1.00  0.00           H  
HETATM   37  H13 UNL     1       6.270  -0.859  -0.473  1.00  0.00           H  
HETATM   38  H14 UNL     1       3.393  -2.585  -0.631  1.00  0.00           H  
HETATM   39  H15 UNL     1       4.552  -2.787   1.340  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.419  -1.511  -0.809  1.00  0.00           H  
HETATM   41  H17 UNL     1       1.713  -2.887   1.337  1.00  0.00           H  
HETATM   42  H18 UNL     1      -0.826  -1.002  -0.388  1.00  0.00           H  
HETATM   43  H19 UNL     1      -1.882   0.705  -2.274  1.00  0.00           H  
HETATM   44  H20 UNL     1      -1.787  -1.049  -2.387  1.00  0.00           H  
HETATM   45  H21 UNL     1      -4.028  -1.079  -2.378  1.00  0.00           H  
HETATM   46  H22 UNL     1      -4.174   0.659  -2.154  1.00  0.00           H  
HETATM   47  H23 UNL     1      -4.847  -1.326  -0.315  1.00  0.00           H  
HETATM   48  H24 UNL     1      -4.379   0.974   1.347  1.00  0.00           H  
HETATM   49  H25 UNL     1      -4.861   1.538  -0.279  1.00  0.00           H  
HETATM   50  H26 UNL     1      -5.882   0.407   0.637  1.00  0.00           H  
HETATM   51  H27 UNL     1      -2.764  -2.019  -0.031  1.00  0.00           H  
HETATM   52  H28 UNL     1      -4.136  -2.588   2.505  1.00  0.00           H  
CONECT    1    2   25   26   27
CONECT    2    3   16   28
CONECT    3    4   29   30
CONECT    4    5
CONECT    5    6   14   31
CONECT    6    7
CONECT    7    8   10   32
CONECT    8    9   33   34
CONECT    9   35
CONECT   10   11   12   36
CONECT   11   37
CONECT   12   13   14   38
CONECT   13   39
CONECT   14   15   40
CONECT   15   41
CONECT   16   17   21   42
CONECT   17   18   43   44
CONECT   18   19   45   46
CONECT   19   20   21   47
CONECT   20   48   49   50
CONECT   21   22   51
CONECT   22   23   23   24
CONECT   24   52
END

HMDB0039014
     RDKit          3D
Nepetariaside
 52 53  0  0  0  0  0  0  0  0999 V2000
   -2.0587    2.2031   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1118    1.0253   -0.0285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2512    1.2075    1.1858 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6865    0.2449    1.4339 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7031    0.1206    0.4886 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8501    0.5898    1.1764 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9771    0.6270    0.4110 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8802    1.7326   -0.6128 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0985    1.6751   -1.3337 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3195   -0.6952   -0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5833   -1.0979    0.1962 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3463   -1.7789    0.1301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6439   -2.3708    1.3572 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9186   -1.3077    0.1901 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2022   -2.0864    1.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6770   -0.2815   -0.3147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1947   -0.2354   -1.7835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6918   -0.2329   -1.7028 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1062   -0.4656   -0.2839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8040    0.6455    0.3842 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7957   -0.9097    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9209   -1.0936    1.7626 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0932   -0.8697    2.6621 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1392   -1.5989    2.2375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6592    2.1059   -1.0445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3944    3.1026   -0.3157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5842    2.4389    0.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3774    1.2350   -0.8842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2728    2.2274    1.0257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8114    1.3855    2.1252 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5346    0.7933   -0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8086    0.9375    1.1062 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0963    1.5986   -1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8740    2.7253   -0.1361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7291    2.3674   -1.0455 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3666   -0.5547   -1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2698   -0.8591   -0.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3931   -2.5848   -0.6311 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5517   -2.7871    1.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4191   -1.5112   -0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7126   -2.8869    1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8264   -1.0021   -0.3884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8821    0.7045   -2.2745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7874   -1.0491   -2.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0281   -1.0794   -2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1737    0.6586   -2.1544 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8468   -1.3261   -0.3146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3792    0.9745    1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8609    1.5381   -0.2790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8822    0.4068    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7639   -2.0186   -0.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1359   -2.5880    2.5053 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  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
  2 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 14  5  1  0
 21 16  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
  5 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 12 38  1  0
 13 39  1  0
 14 40  1  0
 15 41  1  0
 16 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 20 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 24 52  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Daunosamine	HMDB
2-Methyl-5-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)cyclopentane-1-carboxylate	Generator

Chemical Formula

C₁₆H₂₈O₈

Average Molecular Weight

348.3887

Monoisotopic Molecular Weight

348.178417872

IUPAC Name

2-methyl-5-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)cyclopentane-1-carboxylic acid

Traditional Name

2-methyl-5-(1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)cyclopentane-1-carboxylic acid

CAS Registry Number

110344-61-1

SMILES

CC(COC1OC(CO)C(O)C(O)C1O)C1CCC(C)C1C(O)=O

InChI Identifier

InChI=1S/C16H28O8/c1-7-3-4-9(11(7)15(21)22)8(2)6-23-16-14(20)13(19)12(18)10(5-17)24-16/h7-14,16-20H,3-6H2,1-2H3,(H,21,22)

InChI Key

NCBSGBLITRBNGW-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
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Monocyclic monoterpenoid
Monoterpenoid
Monosaccharide
Oxane
Secondary alcohol
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Acetal
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Polyol
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Primary alcohol
Alcohol
Organooxygen compound
Carbonyl group
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0039014)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039014)

Source

Endogenous

Endogenous (HMDB: HMDB0039014)

Plant

Plant (HMDB: HMDB0039014)

Animal

Animal (HMDB: HMDB0039014)

Exogenous

Food

Food (HMDB: HMDB0039014)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0039014)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0039014)

Cellular process

Cell signaling (HMDB: HMDB0039014)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0039014)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0039014)

Nutrient

Nutrient (HMDB: HMDB0039014)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039014)

Emulsifier (HMDB: HMDB0039014)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	139 - 141 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	9200 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	12.2 g/L	ALOGPS
logP	-1.1	ALOGPS
logP	-0.38	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	4.15	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	81.76 m³·mol⁻¹	ChemAxon
Polarizability	35.68 Å³	ChemAxon
Number of Rings	2	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]+	180.348	31661259
DarkChem	[M-H]-	176.459	31661259
DeepCCS	[M+H]+	186.478	30932474
DeepCCS	[M-H]-	184.12	30932474
DeepCCS	[M-2H]-	217.006	30932474
DeepCCS	[M+Na]+	192.571	30932474
AllCCS	[M+H]+	183.0	32859911
AllCCS	[M+H-H2O]+	180.3	32859911
AllCCS	[M+NH4]+	185.6	32859911
AllCCS	[M+Na]+	186.4	32859911
AllCCS	[M-H]-	181.1	32859911
AllCCS	[M+Na-2H]-	181.4	32859911
AllCCS	[M+HCOO]-	182.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nepetariaside	CC(COC1OC(CO)C(O)C(O)C1O)C1CCC(C)C1C(O)=O	3692.4	Standard polar	33892256
Nepetariaside	CC(COC1OC(CO)C(O)C(O)C1O)C1CCC(C)C1C(O)=O	2838.3	Standard non polar	33892256
Nepetariaside	CC(COC1OC(CO)C(O)C(O)C1O)C1CCC(C)C1C(O)=O	2811.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nepetariaside,1TMS,isomer #1	CC(COC1OC(CO[Si](C)(C)C)C(O)C(O)C1O)C1CCC(C)C1C(=O)O	2850.1	Semi standard non polar	33892256
Nepetariaside,1TMS,isomer #2	CC(COC1OC(CO)C(O[Si](C)(C)C)C(O)C1O)C1CCC(C)C1C(=O)O	2832.5	Semi standard non polar	33892256
Nepetariaside,1TMS,isomer #3	CC(COC1OC(CO)C(O)C(O[Si](C)(C)C)C1O)C1CCC(C)C1C(=O)O	2811.6	Semi standard non polar	33892256
Nepetariaside,1TMS,isomer #4	CC(COC1OC(CO)C(O)C(O)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O	2827.2	Semi standard non polar	33892256
Nepetariaside,1TMS,isomer #5	CC(COC1OC(CO)C(O)C(O)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C	2828.7	Semi standard non polar	33892256
Nepetariaside,2TMS,isomer #1	CC(COC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O)C1CCC(C)C1C(=O)O	2823.7	Semi standard non polar	33892256
Nepetariaside,2TMS,isomer #10	CC(COC1OC(CO)C(O)C(O)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C	2762.6	Semi standard non polar	33892256
Nepetariaside,2TMS,isomer #2	CC(COC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O)C1CCC(C)C1C(=O)O	2808.8	Semi standard non polar	33892256
Nepetariaside,2TMS,isomer #3	CC(COC1OC(CO[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O	2820.7	Semi standard non polar	33892256
Nepetariaside,2TMS,isomer #4	CC(COC1OC(CO[Si](C)(C)C)C(O)C(O)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C	2774.0	Semi standard non polar	33892256
Nepetariaside,2TMS,isomer #5	CC(COC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)C1CCC(C)C1C(=O)O	2803.0	Semi standard non polar	33892256
Nepetariaside,2TMS,isomer #6	CC(COC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O	2797.9	Semi standard non polar	33892256
Nepetariaside,2TMS,isomer #7	CC(COC1OC(CO)C(O[Si](C)(C)C)C(O)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C	2775.3	Semi standard non polar	33892256
Nepetariaside,2TMS,isomer #8	CC(COC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O	2813.7	Semi standard non polar	33892256
Nepetariaside,2TMS,isomer #9	CC(COC1OC(CO)C(O)C(O[Si](C)(C)C)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C	2760.0	Semi standard non polar	33892256
Nepetariaside,3TMS,isomer #1	CC(COC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)C1CCC(C)C1C(=O)O	2777.4	Semi standard non polar	33892256
Nepetariaside,3TMS,isomer #10	CC(COC1OC(CO)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C	2705.8	Semi standard non polar	33892256
Nepetariaside,3TMS,isomer #2	CC(COC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O	2815.9	Semi standard non polar	33892256
Nepetariaside,3TMS,isomer #3	CC(COC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C	2708.2	Semi standard non polar	33892256
Nepetariaside,3TMS,isomer #4	CC(COC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O	2784.0	Semi standard non polar	33892256
Nepetariaside,3TMS,isomer #5	CC(COC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C	2696.7	Semi standard non polar	33892256
Nepetariaside,3TMS,isomer #6	CC(COC1OC(CO[Si](C)(C)C)C(O)C(O)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C	2708.5	Semi standard non polar	33892256
Nepetariaside,3TMS,isomer #7	CC(COC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O	2791.5	Semi standard non polar	33892256
Nepetariaside,3TMS,isomer #8	CC(COC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C	2697.6	Semi standard non polar	33892256
Nepetariaside,3TMS,isomer #9	CC(COC1OC(CO)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C	2705.3	Semi standard non polar	33892256
Nepetariaside,4TMS,isomer #1	CC(COC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O	2820.4	Semi standard non polar	33892256
Nepetariaside,4TMS,isomer #2	CC(COC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C	2646.5	Semi standard non polar	33892256
Nepetariaside,4TMS,isomer #3	CC(COC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C	2716.4	Semi standard non polar	33892256
Nepetariaside,4TMS,isomer #4	CC(COC1OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C	2635.8	Semi standard non polar	33892256
Nepetariaside,4TMS,isomer #5	CC(COC1OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C	2637.2	Semi standard non polar	33892256
Nepetariaside,5TMS,isomer #1	CC(COC1OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C	2687.1	Semi standard non polar	33892256
Nepetariaside,1TBDMS,isomer #1	CC(COC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O)C1CCC(C)C1C(=O)O	3083.9	Semi standard non polar	33892256
Nepetariaside,1TBDMS,isomer #2	CC(COC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O)C1CCC(C)C1C(=O)O	3088.0	Semi standard non polar	33892256
Nepetariaside,1TBDMS,isomer #3	CC(COC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O)C1CCC(C)C1C(=O)O	3072.4	Semi standard non polar	33892256
Nepetariaside,1TBDMS,isomer #4	CC(COC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O	3082.3	Semi standard non polar	33892256
Nepetariaside,1TBDMS,isomer #5	CC(COC1OC(CO)C(O)C(O)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3068.7	Semi standard non polar	33892256
Nepetariaside,2TBDMS,isomer #1	CC(COC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O)C1CCC(C)C1C(=O)O	3267.6	Semi standard non polar	33892256
Nepetariaside,2TBDMS,isomer #10	CC(COC1OC(CO)C(O)C(O)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3226.7	Semi standard non polar	33892256
Nepetariaside,2TBDMS,isomer #2	CC(COC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O)C1CCC(C)C1C(=O)O	3259.2	Semi standard non polar	33892256
Nepetariaside,2TBDMS,isomer #3	CC(COC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O	3259.3	Semi standard non polar	33892256
Nepetariaside,2TBDMS,isomer #4	CC(COC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3212.4	Semi standard non polar	33892256
Nepetariaside,2TBDMS,isomer #5	CC(COC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O)C1CCC(C)C1C(=O)O	3267.2	Semi standard non polar	33892256
Nepetariaside,2TBDMS,isomer #6	CC(COC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O	3266.4	Semi standard non polar	33892256
Nepetariaside,2TBDMS,isomer #7	CC(COC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3233.9	Semi standard non polar	33892256
Nepetariaside,2TBDMS,isomer #8	CC(COC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O	3277.8	Semi standard non polar	33892256
Nepetariaside,2TBDMS,isomer #9	CC(COC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3213.3	Semi standard non polar	33892256
Nepetariaside,3TBDMS,isomer #1	CC(COC1OC(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)C1O)C1CCC(C)C1C(=O)O	3457.0	Semi standard non polar	33892256
Nepetariaside,3TBDMS,isomer #10	CC(COC1OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3424.4	Semi standard non polar	33892256
Nepetariaside,3TBDMS,isomer #2	CC(COC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O	3463.8	Semi standard non polar	33892256
Nepetariaside,3TBDMS,isomer #3	CC(COC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3410.7	Semi standard non polar	33892256
Nepetariaside,3TBDMS,isomer #4	CC(COC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O	3457.0	Semi standard non polar	33892256
Nepetariaside,3TBDMS,isomer #5	CC(COC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3391.3	Semi standard non polar	33892256
Nepetariaside,3TBDMS,isomer #6	CC(COC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3401.8	Semi standard non polar	33892256
Nepetariaside,3TBDMS,isomer #7	CC(COC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O	3457.4	Semi standard non polar	33892256
Nepetariaside,3TBDMS,isomer #8	CC(COC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3407.7	Semi standard non polar	33892256
Nepetariaside,3TBDMS,isomer #9	CC(COC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3409.7	Semi standard non polar	33892256
Nepetariaside,4TBDMS,isomer #1	CC(COC1OC(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)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O	3687.4	Semi standard non polar	33892256
Nepetariaside,4TBDMS,isomer #2	CC(COC1OC(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)C1O)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3593.7	Semi standard non polar	33892256
Nepetariaside,4TBDMS,isomer #3	CC(COC1OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3634.1	Semi standard non polar	33892256
Nepetariaside,4TBDMS,isomer #4	CC(COC1OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3597.0	Semi standard non polar	33892256
Nepetariaside,4TBDMS,isomer #5	CC(COC1OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C)C1CCC(C)C1C(=O)O[Si](C)(C)C(C)(C)C	3601.1	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 - Nepetariaside GC-MS (Non-derivatized) - 70eV, Positive	splash10-0ac9-9535000000-f81e4c70e74a2670b8ee	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nepetariaside GC-MS (4 TMS) - 70eV, Positive	splash10-00di-4311239000-501786327dbf4cd3272e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nepetariaside GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nepetariaside 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 - Nepetariaside 10V, Positive-QTOF	splash10-00l2-0809000000-fd86b7b0a20801b5b591	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetariaside 20V, Positive-QTOF	splash10-014r-1901000000-8ffe2712179d36d23a0d	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetariaside 40V, Positive-QTOF	splash10-01bc-8910000000-90d5cd7b7e69bc69edcf	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetariaside 10V, Negative-QTOF	splash10-0002-1519000000-57d1fd1d9ffb5d2e9fb0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetariaside 20V, Negative-QTOF	splash10-03mr-3913000000-dd62ef2cc5d93a449c33	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetariaside 40V, Negative-QTOF	splash10-0a4u-9600000000-07f923095dcbfe06eee8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetariaside 10V, Positive-QTOF	splash10-0udj-0219000000-b75082cb7d4512181545	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetariaside 20V, Positive-QTOF	splash10-00dl-2901000000-d1d03221a0ff09636188	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetariaside 40V, Positive-QTOF	splash10-052g-9500000000-99b228cd2acfe1aae8ac	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetariaside 10V, Negative-QTOF	splash10-0002-0009000000-4ec41ecd14c916a04423	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetariaside 20V, Negative-QTOF	splash10-0f6w-3479000000-8360f82eb67ece4d6da8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nepetariaside 40V, Negative-QTOF	splash10-052f-9610000000-55abd34c64ead7a37dca	2021-09-24	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
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018508

KNApSAcK ID

C00056847

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

131752511

PDB ID

Not Available

ChEBI ID

175434

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1873531

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 Nepetariaside (HMDB0039014)

MOL for HMDB0039014 (Nepetariaside)

3D MOL for HMDB0039014 (Nepetariaside)

3D SDF for HMDB0039014 (Nepetariaside)

3D-SDF for HMDB0039014 (Nepetariaside)

PDB for HMDB0039014 (Nepetariaside)

3D PDB for HMDB0039014 (Nepetariaside)

SMILES for HMDB0039014 (Nepetariaside)

INCHI for HMDB0039014 (Nepetariaside)

Structure for HMDB0039014 (Nepetariaside)

3D Structure for HMDB0039014 (Nepetariaside)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra