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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:35:23 UTC

Update Date

2022-03-07 02:55:17 UTC

HMDB ID

HMDB0037350

Secondary Accession Numbers

HMDB37350

Metabolite Identification

Common Name

Menthoside

Description

Menthoside belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Menthoside has been detected, but not quantified in, herbs and spices and peppermints (Mentha X piperita). This could make menthoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Menthoside.

Structure

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


  Mrv0541 05061309442D          

 53 58  0  0  0  0            999 V2000
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 53 26  1  0  0  0  0
 53 36  1  0  0  0  0
M  END

HMDB0037350
     RDKit          3D
Menthoside
 89 94  0  0  0  0  0  0  0  0999 V2000
  -10.5145    0.2165    2.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7791    0.6671    1.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 05061309442D          

 53 58  0  0  0  0            999 V2000
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  1  0  0  0  0
  7  5  2  0  0  0  0
  8  2  2  0  0  0  0
  9  3  2  0  0  0  0
 15  1  1  0  0  0  0
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 17  4  2  0  0  0  0
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 53 26  1  0  0  0  0
 53 36  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037350

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1OC(OCC2OC(OC3=CC(O)=C4C(=O)C=C(OC4=C3)C3=CC=C(OC(=O)\C=C\C4=CC(O)=C(O)C=C4)C=C3)C(O)C(O)C2O)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C36H36O17/c1-15-29(42)31(44)33(46)35(49-15)48-14-26-30(43)32(45)34(47)36(53-26)51-19-11-22(39)28-23(40)13-24(52-25(28)12-19)17-4-6-18(7-5-17)50-27(41)9-3-16-2-8-20(37)21(38)10-16/h2-13,15,26,29-39,42-47H,14H2,1H3/b9-3+

> <INCHI_KEY>
VFFCBWDFYBEZAX-YCRREMRBSA-N

> <FORMULA>
C36H36O17

> <MOLECULAR_WEIGHT>
740.6608

> <EXACT_MASS>
740.195249726

> <JCHEM_ACCEPTOR_COUNT>
16

> <JCHEM_AVERAGE_POLARIZABILITY>
74.26311019333076

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-{5-hydroxy-4-oxo-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-2-yl}phenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.611156321666666

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.287289054293888

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.43405824706979

> <JCHEM_PKA_STRONGEST_BASIC>
-3.648685994297134

> <JCHEM_POLAR_SURFACE_AREA>
271.5899999999999

> <JCHEM_REFRACTIVITY>
179.45740000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.14e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-{5-hydroxy-4-oxo-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]chromen-2-yl}phenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037350
     RDKit          3D
Menthoside
 89 94  0  0  0  0  0  0  0  0999 V2000
  -10.5145    0.2165    2.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7791    0.6671    1.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9289    1.6938    1.5397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6945    1.5620    0.8871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8983    2.6623    1.0240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5248    3.2296   -0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7288    2.2942   -1.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5327    1.8893   -0.4971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1630    0.6892   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770    0.5837   -1.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0691   -0.2471   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515   -1.0637    0.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410   -1.9181    1.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6021   -2.6825    2.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707   -1.9495    1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2495   -2.7360    2.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2603   -3.4866    3.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2038   -1.8846    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6681   -1.8430    0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5556   -2.4797    1.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9268   -2.4605    1.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4235   -1.8044    0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7615   -1.7645    0.1587 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4658   -0.5437    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8529    0.5437    0.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8977   -0.6519   -0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7134    0.3595   -0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1356    0.2758   -0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8007   -0.9201   -0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1733   -0.9976   -0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8885    0.1439   -1.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2692    0.0945   -1.4305 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2516    1.3695   -1.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9700    2.5306   -1.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8835    1.4230   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5521   -1.1429   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1987   -1.1777   -0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996   -1.1531    0.3804 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -1.1426    0.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6799   -0.3288   -0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5489    0.6640   -2.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6193   -0.0740   -3.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6825    1.9920   -3.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3793    2.4851   -3.4445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4071    2.9788   -2.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5388    4.0327   -2.0647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0019    0.3795    1.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1686    0.6045    2.9567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7692   -0.8619    1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9850   -1.5304    0.2123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1004   -0.5219    0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9399   -1.6230    0.7161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9631   -0.6057    2.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6281    1.1141    3.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5416   -0.1486    2.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5205    1.0275    0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.8642    4.0941    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3698    3.6775   -0.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2846    1.3694   -1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6547   -0.1643   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7270   -1.0813    0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3787   -3.3320    3.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2324   -3.3527    2.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1890   -3.0095    2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5716   -3.0021    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3502   -1.6383   -0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2518    1.3508   -0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2859   -1.8417   -0.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6857   -1.9550   -1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7159   -0.8090   -1.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9699    2.4822   -1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3571    2.3714   -0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9864   -0.6232   -1.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5179   -0.6753   -0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1819    0.3067   -1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5031    0.1120   -2.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7553    0.4114   -3.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2021    1.9370   -4.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4224    3.4665   -3.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3446    3.3520   -2.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9908    3.8806   -1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9350    0.3279    1.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4425    1.5511    3.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9090   -1.5165    2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3504   -2.1012    0.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9662   -0.3833   -0.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7513   -1.5602    0.1529 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
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  2  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 32 34  1  0
 34 35  1  0
 34 36  2  0
 23 37  1  0
 37 38  2  0
 19 39  1  0
 39 40  1  0
 40 41  2  0
  9 42  1  0
 42 43  1  0
 42 44  1  0
 44 45  1  0
 44 46  1  0
 46 47  1  0
  4 48  1  0
 48 49  1  0
 48 50  1  0
 50 51  1  0
 50 52  1  0
 52 53  1  0
 52  2  1  0
 46  7  1  0
 41 11  1  0
 40 15  1  0
 38 20  1  0
 36 29  1  0
  1 54  1  0
  1 55  1  0
  1 56  1  0
  2 57  1  0
  4 58  1  0
  6 59  1  0
  6 60  1  0
  7 61  1  0
  9 62  1  0
 12 63  1  0
 14 64  1  0
 18 65  1  0
 21 66  1  0
 22 67  1  0
 27 68  1  0
 28 69  1  0
 30 70  1  0
 31 71  1  0
 33 72  1  0
 35 73  1  0
 36 74  1  0
 37 75  1  0
 38 76  1  0
 41 77  1  0
 42 78  1  0
 43 79  1  0
 44 80  1  0
 45 81  1  0
 46 82  1  0
 47 83  1  0
 48 84  1  0
 49 85  1  0
 50 86  1  0
 51 87  1  0
 52 88  1  0
 53 89  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      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      17.338  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.004  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.672  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.672  -4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.338  -5.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.003  -2.310   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      20.005  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      20.005  -5.390   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.671  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      21.339  -7.700   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      21.339  -4.620   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      14.671  -0.770   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -6.668 -10.010   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      13.337  -3.080   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2    8   16                                                       
CONECT    3    9   16                                                       
CONECT    4    6   17                                                       
CONECT    5    7   17                                                       
CONECT    6    4   18                                                       
CONECT    7    5   18                                                       
CONECT    8    2   20                                                       
CONECT    9    3   27                                                       
CONECT   10   16   21                                                       
CONECT   11   19   22                                                       
CONECT   12   19   25                                                       
CONECT   13   23   24                                                       
CONECT   14   26   48                                                       
CONECT   15    1   29   49                                                  
CONECT   16    2    3   10                                                  
CONECT   17    4    5   24                                                  
CONECT   18    6    7   50                                                  
CONECT   19   11   12   51                                                  
CONECT   20    8   21   37                                                  
CONECT   21   10   20   38                                                  
CONECT   22   11   28   39                                                  
CONECT   23   13   28   40                                                  
CONECT   24   13   17   52                                                  
CONECT   25   12   28   52                                                  
CONECT   26   14   30   53                                                  
CONECT   27    9   41   50                                                  
CONECT   28   22   23   25                                                  
CONECT   29   15   31   42                                                  
CONECT   30   26   32   43                                                  
CONECT   31   29   33   44                                                  
CONECT   32   30   34   45                                                  
CONECT   33   31   35   46                                                  
CONECT   34   32   36   47                                                  
CONECT   35   33   48   49                                                  
CONECT   36   34   51   53                                                  
CONECT   37   20                                                            
CONECT   38   21                                                            
CONECT   39   22                                                            
CONECT   40   23                                                            
CONECT   41   27                                                            
CONECT   42   29                                                            
CONECT   43   30                                                            
CONECT   44   31                                                            
CONECT   45   32                                                            
CONECT   46   33                                                            
CONECT   47   34                                                            
CONECT   48   14   35                                                       
CONECT   49   15   35                                                       
CONECT   50   18   27                                                       
CONECT   51   19   36                                                       
CONECT   52   24   25                                                       
CONECT   53   26   36                                                       
MASTER        0    0    0    0    0    0    0    0   53    0  116    0
END

COMPND    HMDB0037350
HETATM    1  C1  UNL     1     -10.514   0.217   2.443  1.00  0.00           C  
HETATM    2  C2  UNL     1      -9.779   0.667   1.193  1.00  0.00           C  
HETATM    3  O1  UNL     1      -8.929   1.694   1.540  1.00  0.00           O  
HETATM    4  C3  UNL     1      -7.695   1.562   0.887  1.00  0.00           C  
HETATM    5  O2  UNL     1      -6.898   2.662   1.024  1.00  0.00           O  
HETATM    6  C4  UNL     1      -6.525   3.230  -0.196  1.00  0.00           C  
HETATM    7  C5  UNL     1      -5.729   2.294  -1.057  1.00  0.00           C  
HETATM    8  O3  UNL     1      -4.533   1.889  -0.497  1.00  0.00           O  
HETATM    9  C6  UNL     1      -4.163   0.689  -1.126  1.00  0.00           C  
HETATM   10  O4  UNL     1      -2.777   0.584  -1.060  1.00  0.00           O  
HETATM   11  C7  UNL     1      -2.069  -0.247  -0.238  1.00  0.00           C  
HETATM   12  C8  UNL     1      -2.652  -1.064   0.700  1.00  0.00           C  
HETATM   13  C9  UNL     1      -1.941  -1.918   1.546  1.00  0.00           C  
HETATM   14  O5  UNL     1      -2.602  -2.682   2.436  1.00  0.00           O  
HETATM   15  C10 UNL     1      -0.571  -1.949   1.439  1.00  0.00           C  
HETATM   16  C11 UNL     1       0.249  -2.736   2.208  1.00  0.00           C  
HETATM   17  O6  UNL     1      -0.260  -3.487   3.071  1.00  0.00           O  
HETATM   18  C12 UNL     1       1.641  -2.708   2.038  1.00  0.00           C  
HETATM   19  C13 UNL     1       2.204  -1.885   1.090  1.00  0.00           C  
HETATM   20  C14 UNL     1       3.668  -1.843   0.887  1.00  0.00           C  
HETATM   21  C15 UNL     1       4.556  -2.480   1.720  1.00  0.00           C  
HETATM   22  C16 UNL     1       5.927  -2.461   1.488  1.00  0.00           C  
HETATM   23  C17 UNL     1       6.424  -1.804   0.419  1.00  0.00           C  
HETATM   24  O7  UNL     1       7.761  -1.764   0.159  1.00  0.00           O  
HETATM   25  C18 UNL     1       8.466  -0.544   0.037  1.00  0.00           C  
HETATM   26  O8  UNL     1       7.853   0.544   0.157  1.00  0.00           O  
HETATM   27  C19 UNL     1       9.898  -0.652  -0.228  1.00  0.00           C  
HETATM   28  C20 UNL     1      10.713   0.359  -0.395  1.00  0.00           C  
HETATM   29  C21 UNL     1      12.136   0.276  -0.657  1.00  0.00           C  
HETATM   30  C22 UNL     1      12.801  -0.920  -0.717  1.00  0.00           C  
HETATM   31  C23 UNL     1      14.173  -0.998  -0.973  1.00  0.00           C  
HETATM   32  C24 UNL     1      14.889   0.144  -1.172  1.00  0.00           C  
HETATM   33  O9  UNL     1      16.269   0.095  -1.431  1.00  0.00           O  
HETATM   34  C25 UNL     1      14.252   1.369  -1.119  1.00  0.00           C  
HETATM   35  O10 UNL     1      14.970   2.531  -1.320  1.00  0.00           O  
HETATM   36  C26 UNL     1      12.884   1.423  -0.862  1.00  0.00           C  
HETATM   37  C27 UNL     1       5.552  -1.143  -0.452  1.00  0.00           C  
HETATM   38  C28 UNL     1       4.199  -1.178  -0.198  1.00  0.00           C  
HETATM   39  O11 UNL     1       1.400  -1.153   0.380  1.00  0.00           O  
HETATM   40  C29 UNL     1       0.080  -1.143   0.503  1.00  0.00           C  
HETATM   41  C30 UNL     1      -0.680  -0.329  -0.295  1.00  0.00           C  
HETATM   42  C31 UNL     1      -4.549   0.664  -2.579  1.00  0.00           C  
HETATM   43  O12 UNL     1      -3.619  -0.074  -3.325  1.00  0.00           O  
HETATM   44  C32 UNL     1      -4.682   1.992  -3.232  1.00  0.00           C  
HETATM   45  O13 UNL     1      -3.379   2.485  -3.444  1.00  0.00           O  
HETATM   46  C33 UNL     1      -5.407   2.979  -2.361  1.00  0.00           C  
HETATM   47  O14 UNL     1      -4.539   4.033  -2.065  1.00  0.00           O  
HETATM   48  C34 UNL     1      -7.002   0.379   1.582  1.00  0.00           C  
HETATM   49  O15 UNL     1      -7.169   0.605   2.957  1.00  0.00           O  
HETATM   50  C35 UNL     1      -7.769  -0.862   1.170  1.00  0.00           C  
HETATM   51  O16 UNL     1      -6.985  -1.530   0.212  1.00  0.00           O  
HETATM   52  C36 UNL     1      -9.100  -0.522   0.557  1.00  0.00           C  
HETATM   53  O17 UNL     1      -9.940  -1.623   0.716  1.00  0.00           O  
HETATM   54  H1  UNL     1      -9.963  -0.606   2.960  1.00  0.00           H  
HETATM   55  H2  UNL     1     -10.628   1.114   3.098  1.00  0.00           H  
HETATM   56  H3  UNL     1     -11.542  -0.149   2.220  1.00  0.00           H  
HETATM   57  H4  UNL     1     -10.521   1.027   0.437  1.00  0.00           H  
HETATM   58  H5  UNL     1      -7.931   1.302  -0.163  1.00  0.00           H  
HETATM   59  H6  UNL     1      -5.864   4.094   0.061  1.00  0.00           H  
HETATM   60  H7  UNL     1      -7.370   3.678  -0.755  1.00  0.00           H  
HETATM   61  H8  UNL     1      -6.285   1.369  -1.316  1.00  0.00           H  
HETATM   62  H9  UNL     1      -4.655  -0.164  -0.596  1.00  0.00           H  
HETATM   63  H10 UNL     1      -3.727  -1.081   0.838  1.00  0.00           H  
HETATM   64  H11 UNL     1      -2.379  -3.332   3.107  1.00  0.00           H  
HETATM   65  H12 UNL     1       2.232  -3.353   2.675  1.00  0.00           H  
HETATM   66  H13 UNL     1       4.189  -3.009   2.582  1.00  0.00           H  
HETATM   67  H14 UNL     1       6.572  -3.002   2.209  1.00  0.00           H  
HETATM   68  H15 UNL     1      10.350  -1.638  -0.296  1.00  0.00           H  
HETATM   69  H16 UNL     1      10.252   1.351  -0.330  1.00  0.00           H  
HETATM   70  H17 UNL     1      12.286  -1.842  -0.572  1.00  0.00           H  
HETATM   71  H18 UNL     1      14.686  -1.955  -1.015  1.00  0.00           H  
HETATM   72  H19 UNL     1      16.716  -0.809  -1.466  1.00  0.00           H  
HETATM   73  H20 UNL     1      15.970   2.482  -1.508  1.00  0.00           H  
HETATM   74  H21 UNL     1      12.357   2.371  -0.816  1.00  0.00           H  
HETATM   75  H22 UNL     1       5.986  -0.623  -1.305  1.00  0.00           H  
HETATM   76  H23 UNL     1       3.518  -0.675  -0.862  1.00  0.00           H  
HETATM   77  H24 UNL     1      -0.182   0.307  -1.031  1.00  0.00           H  
HETATM   78  H25 UNL     1      -5.503   0.112  -2.674  1.00  0.00           H  
HETATM   79  H26 UNL     1      -2.755   0.411  -3.340  1.00  0.00           H  
HETATM   80  H27 UNL     1      -5.202   1.937  -4.220  1.00  0.00           H  
HETATM   81  H28 UNL     1      -3.422   3.467  -3.568  1.00  0.00           H  
HETATM   82  H29 UNL     1      -6.345   3.352  -2.835  1.00  0.00           H  
HETATM   83  H30 UNL     1      -3.991   3.881  -1.273  1.00  0.00           H  
HETATM   84  H31 UNL     1      -5.935   0.328   1.379  1.00  0.00           H  
HETATM   85  H32 UNL     1      -7.442   1.551   3.138  1.00  0.00           H  
HETATM   86  H33 UNL     1      -7.909  -1.517   2.051  1.00  0.00           H  
HETATM   87  H34 UNL     1      -6.350  -2.101   0.752  1.00  0.00           H  
HETATM   88  H35 UNL     1      -8.966  -0.383  -0.552  1.00  0.00           H  
HETATM   89  H36 UNL     1     -10.751  -1.560   0.153  1.00  0.00           H  
CONECT    1    2   54   55   56
CONECT    2    3   52   57
CONECT    3    4
CONECT    4    5   48   58
CONECT    5    6
CONECT    6    7   59   60
CONECT    7    8   46   61
CONECT    8    9
CONECT    9   10   42   62
CONECT   10   11
CONECT   11   12   12   41
CONECT   12   13   63
CONECT   13   14   15   15
CONECT   14   64
CONECT   15   16   40
CONECT   16   17   17   18
CONECT   18   19   19   65
CONECT   19   20   39
CONECT   20   21   21   38
CONECT   21   22   66
CONECT   22   23   23   67
CONECT   23   24   37
CONECT   24   25
CONECT   25   26   26   27
CONECT   27   28   28   68
CONECT   28   29   69
CONECT   29   30   30   36
CONECT   30   31   70
CONECT   31   32   32   71
CONECT   32   33   34
CONECT   33   72
CONECT   34   35   36   36
CONECT   35   73
CONECT   36   74
CONECT   37   38   38   75
CONECT   38   76
CONECT   39   40
CONECT   40   41   41
CONECT   41   77
CONECT   42   43   44   78
CONECT   43   79
CONECT   44   45   46   80
CONECT   45   81
CONECT   46   47   82
CONECT   47   83
CONECT   48   49   50   84
CONECT   49   85
CONECT   50   51   52   86
CONECT   51   87
CONECT   52   53   88
CONECT   53   89
END

HMDB0037350
     RDKit          3D
Menthoside
 89 94  0  0  0  0  0  0  0  0999 V2000
  -10.5145    0.2165    2.4428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7791    0.6671    1.1925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9289    1.6938    1.5397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6945    1.5620    0.8871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8983    2.6623    1.0240 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5248    3.2296   -0.1962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7288    2.2942   -1.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5327    1.8893   -0.4971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1630    0.6892   -1.1264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7770    0.5837   -1.0604 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0691   -0.2471   -0.2381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6515   -1.0637    0.7001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9410   -1.9181    1.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6021   -2.6825    2.4359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5707   -1.9495    1.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2495   -2.7360    2.2076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2603   -3.4866    3.0707 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6406   -2.7083    2.0381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2038   -1.8846    1.0900 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6681   -1.8430    0.8869 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5556   -2.4797    1.7200 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9268   -2.4605    1.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4235   -1.8044    0.4189 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7615   -1.7645    0.1587 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4658   -0.5437    0.0373 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8529    0.5437    0.1568 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8977   -0.6519   -0.2277 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7134    0.3595   -0.3950 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1356    0.2758   -0.6565 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8007   -0.9201   -0.7167 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1733   -0.9976   -0.9730 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8885    0.1439   -1.1720 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2692    0.0945   -1.4305 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2516    1.3695   -1.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9700    2.5306   -1.3204 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.8835    1.4230   -0.8624 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5521   -1.1429   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1987   -1.1777   -0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3996   -1.1531    0.3804 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0797   -1.1426    0.5034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6799   -0.3288   -0.2947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5489    0.6640   -2.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6193   -0.0740   -3.3248 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6825    1.9920   -3.2320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3793    2.4851   -3.4445 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4071    2.9788   -2.3613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5388    4.0327   -2.0647 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0019    0.3795    1.5819 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1686    0.6045    2.9567 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7692   -0.8619    1.1697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9850   -1.5304    0.2123 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1004   -0.5219    0.5571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9399   -1.6230    0.7161 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9631   -0.6057    2.9600 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6281    1.1141    3.0980 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5416   -0.1486    2.2205 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5205    1.0275    0.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9313    1.3016   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8642    4.0941    0.0606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3698    3.6775   -0.7550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2846    1.3694   -1.3164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6547   -0.1643   -0.5957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7270   -1.0813    0.8376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3787   -3.3320    3.1075 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2324   -3.3527    2.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1890   -3.0095    2.5821 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5716   -3.0021    2.2095 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3502   -1.6383   -0.2957 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2518    1.3508   -0.3298 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.2859   -1.8417   -0.5721 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.6857   -1.9550   -1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   16.7159   -0.8090   -1.4663 H   0  0  0  0  0  0  0  0  0  0  0  0
   15.9699    2.4822   -1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.3571    2.3714   -0.8161 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9864   -0.6232   -1.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5179   -0.6753   -0.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1819    0.3067   -1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5031    0.1120   -2.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7553    0.4114   -3.3398 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2021    1.9370   -4.2203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4224    3.4665   -3.5683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3446    3.3520   -2.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9908    3.8806   -1.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9350    0.3279    1.3788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4425    1.5511    3.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9090   -1.5165    2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3504   -2.1012    0.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9662   -0.3833   -0.5521 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7513   -1.5602    0.1529 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
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  9 10  1  0
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M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Apigenin 7-O-rutinoside 4'-O-caffeate	HMDB
Apigenin 7-rutinoside-4'-trans-caffeate	HMDB
4-{5-hydroxy-4-oxo-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-2-yl}phenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₃₆H₃₆O₁₇

Average Molecular Weight

740.6608

Monoisotopic Molecular Weight

740.195249726

IUPAC Name

4-{5-hydroxy-4-oxo-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-4H-chromen-2-yl}phenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

4-{5-hydroxy-4-oxo-7-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]methyl}oxan-2-yl)oxy]chromen-2-yl}phenyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

14637-28-6

SMILES

CC1OC(OCC2OC(OC3=CC(O)=C4C(=O)C=C(OC4=C3)C3=CC=C(OC(=O)\C=C\C4=CC(O)=C(O)C=C4)C=C3)C(O)C(O)C2O)C(O)C(O)C1O

InChI Identifier

InChI=1S/C36H36O17/c1-15-29(42)31(44)33(46)35(49-15)48-14-26-30(43)32(45)34(47)36(53-26)51-19-11-22(39)28-23(40)13-24(52-25(28)12-19)17-4-6-18(7-5-17)50-27(41)9-3-16-2-8-20(37)21(38)10-16/h2-13,15,26,29-39,42-47H,14H2,1H3/b9-3+

InChI Key

VFFCBWDFYBEZAX-YCRREMRBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
5-hydroxyflavonoid
Hydroxyflavonoid
Flavone
Phenolic glycoside
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Disaccharide
Glycosyl compound
O-glycosyl compound
Chromone
Benzopyran
Phenol ester
1-benzopyran
Styrene
Catechol
Phenoxy compound
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Pyranone
Pyran
Oxane
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Enoate ester
Heteroaromatic compound
Alpha,beta-unsaturated carboxylic ester
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Carboxylic acid derivative
Acetal
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0037350)
Cytoplasm (HMDB: HMDB0037350)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037350)

Source

Exogenous

Exogenous (HMDB: HMDB0037350)

Food

Food (HMDB: HMDB0037350)

Herb and spice

Herb

Peppermint (FooDB: FOOD00113)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0037350)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0037350)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	271 - 273 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	15.03 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	0.21 g/L	ALOGPS
logP	1.91	ALOGPS
logP	1.61	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	16	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	271.59 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	179.46 m³·mol⁻¹	ChemAxon
Polarizability	74.26 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	254.171	30932474
DeepCCS	[M-H]-	252.346	30932474
DeepCCS	[M-2H]-	286.108	30932474
DeepCCS	[M+Na]+	259.882	30932474
AllCCS	[M+H]+	254.1	32859911
AllCCS	[M+H-H2O]+	253.7	32859911
AllCCS	[M+NH4]+	254.3	32859911
AllCCS	[M+Na]+	254.4	32859911
AllCCS	[M-H]-	247.7	32859911
AllCCS	[M+Na-2H]-	251.5	32859911
AllCCS	[M+HCOO]-	255.7	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.	5.8 minutes	32390414
Predicted by Siyang on May 30, 2022	12.5934 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.0 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	170.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2583.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	187.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	158.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	183.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	103.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	412.4 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	464.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	426.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	872.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	538.5 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	1405.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	316.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	333.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	329.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	340.1 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	101.4 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Menthoside	CC1OC(OCC2OC(OC3=CC(O)=C4C(=O)C=C(OC4=C3)C3=CC=C(OC(=O)\C=C\C4=CC(O)=C(O)C=C4)C=C3)C(O)C(O)C2O)C(O)C(O)C1O	7734.4	Standard polar	33892256
Menthoside	CC1OC(OCC2OC(OC3=CC(O)=C4C(=O)C=C(OC4=C3)C3=CC=C(OC(=O)\C=C\C4=CC(O)=C(O)C=C4)C=C3)C(O)C(O)C2O)C(O)C(O)C1O	5923.3	Standard non polar	33892256
Menthoside	CC1OC(OCC2OC(OC3=CC(O)=C4C(=O)C=C(OC4=C3)C3=CC=C(OC(=O)\C=C\C4=CC(O)=C(O)C=C4)C=C3)C(O)C(O)C2O)C(O)C(O)C1O	7024.7	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016372

KNApSAcK ID

C00004193

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

131752174

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1860061

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Menthoside (HMDB0037350)

MOL for HMDB0037350 (Menthoside)

3D MOL for HMDB0037350 (Menthoside)

3D SDF for HMDB0037350 (Menthoside)

3D-SDF for HMDB0037350 (Menthoside)

PDB for HMDB0037350 (Menthoside)

3D PDB for HMDB0037350 (Menthoside)

SMILES for HMDB0037350 (Menthoside)

INCHI for HMDB0037350 (Menthoside)

Structure for HMDB0037350 (Menthoside)

3D Structure for HMDB0037350 (Menthoside)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized