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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:23:29 UTC

Update Date

2022-03-07 02:56:03 UTC

HMDB ID

HMDB0039039

Secondary Accession Numbers

HMDB39039

Metabolite Identification

Common Name

(R)-Apiumetin glucoside

Description

(R)-Apiumetin glucoside belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety (R)-Apiumetin glucoside has been detected, but not quantified in, green vegetables and wild celeries (Apium graveolens). This could make (R)-apiumetin glucoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Apiumetin glucoside.

Structure

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


  Mrv0541 05061310482D          

 29 32  0  0  0  0            999 V2000
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2168    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13  4  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  2  0  0  0  0
 19 17  2  0  0  0  0
 19 18  1  0  0  0  0
 20 16  1  0  0  0  0
 21  7  1  0  0  0  0
 22 13  2  0  0  0  0
 23 14  1  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 11  1  0  0  0  0
 26 18  1  0  0  0  0
 27 12  1  0  0  0  0
 27 20  1  0  0  0  0
 28 13  1  0  0  0  0
 28 17  1  0  0  0  0
 29 19  1  0  0  0  0
 29 20  1  0  0  0  0
M  END

HMDB0039039
     RDKit          3D
(R)-Apiumetin glucoside
 51 54  0  0  0  0  0  0  0  0999 V2000
   -3.2055   -3.2488    1.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9576   -2.2743    0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4307   -2.2983    0.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4624   -1.1171   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012    0.1304    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7629    1.0748    0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    2.4467    0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6191    3.0806   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5162    4.4640   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895    5.0371   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044    4.2437   -1.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6690    4.6936   -1.8435 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4664    2.9495   -1.3025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5819    2.3379   -0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359    0.9536   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4439    0.2686   -1.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987   -0.0819   -0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6997    0.4283   -0.9281 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7314    0.1604   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0017   -0.1992   -0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0350   -0.4671    0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534   -0.8594    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9399   -0.3029    2.1524 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5941   -1.9986    0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139   -3.1265    0.1539 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6211   -1.6099   -0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1536   -1.9022   -1.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7468    0.2992   -0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0593   -1.0503   -0.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1359   -3.2523    0.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062   -4.0615    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490   -1.3310    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7117   -3.1058    1.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0136   -2.4133    0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8989   -1.0311   -1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8245    0.4664    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5943   -0.0520    1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5202    3.0621    0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388    5.0098    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875    6.0962   -0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3209    0.2477    0.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9820    1.1225    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8194   -1.1021   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2772    0.6306   -1.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5777   -1.2378   -0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479   -1.3037    1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4270    0.5046    2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -2.3221    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139   -3.2290   -0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6145   -2.0128   -0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7125   -2.7172   -2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 15 28  2  0
 28 29  1  0
 29  4  1  0
 28  6  1  0
 14  8  2  0
 26 17  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
M  END


  Mrv0541 05061310482D          

 29 32  0  0  0  0            999 V2000
   -1.8659    0.8085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8659    2.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4534    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2168    3.5854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2135    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5023    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    5.6479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    4.8229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0734    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  8  1  2  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  5  1  0  0  0  0
 10  6  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  7  1  0  0  0  0
 13  4  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17  9  1  0  0  0  0
 18 10  2  0  0  0  0
 19 17  2  0  0  0  0
 19 18  1  0  0  0  0
 20 16  1  0  0  0  0
 21  7  1  0  0  0  0
 22 13  2  0  0  0  0
 23 14  1  0  0  0  0
 24 15  1  0  0  0  0
 25 16  1  0  0  0  0
 26 11  1  0  0  0  0
 26 18  1  0  0  0  0
 27 12  1  0  0  0  0
 27 20  1  0  0  0  0
 28 13  1  0  0  0  0
 28 17  1  0  0  0  0
 29 19  1  0  0  0  0
 29 20  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039039

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CC2=C(O1)C(OC1OC(CO)C(O)C(O)C1O)=C1OC(=O)C=CC1=C2

> <INCHI_IDENTIFIER>
InChI=1S/C20H22O9/c1-8(2)11-6-10-5-9-3-4-13(22)28-17(9)19(18(10)26-11)29-20-16(25)15(24)14(23)12(7-21)27-20/h3-5,11-12,14-16,20-21,23-25H,1,6-7H2,2H3

> <INCHI_KEY>
VPAPSBNFWBXZLU-UHFFFAOYSA-N

> <FORMULA>
C20H22O9

> <MOLECULAR_WEIGHT>
406.3833

> <EXACT_MASS>
406.126382302

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_AVERAGE_POLARIZABILITY>
40.23015136480146

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(prop-1-en-2-yl)-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,7H-furo[3,2-g]chromen-7-one

> <ALOGPS_LOGP>
-0.00

> <JCHEM_LOGP>
0.1283216059999998

> <ALOGPS_LOGS>
-2.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.195995297663739

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.199886092905503

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923662274655

> <JCHEM_POLAR_SURFACE_AREA>
134.91000000000003

> <JCHEM_REFRACTIVITY>
98.56159999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.51e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(prop-1-en-2-yl)-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H-furo[3,2-g]chromen-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039039
     RDKit          3D
(R)-Apiumetin glucoside
 51 54  0  0  0  0  0  0  0  0999 V2000
   -3.2055   -3.2488    1.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9576   -2.2743    0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4307   -2.2983    0.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4624   -1.1171   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012    0.1304    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7629    1.0748    0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    2.4467    0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6191    3.0806   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5162    4.4640   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895    5.0371   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044    4.2437   -1.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6690    4.6936   -1.8435 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4664    2.9495   -1.3025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5819    2.3379   -0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359    0.9536   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4439    0.2686   -1.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987   -0.0819   -0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6997    0.4283   -0.9281 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7314    0.1604   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0017   -0.1992   -0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0350   -0.4671    0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534   -0.8594    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9399   -0.3029    2.1524 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5941   -1.9986    0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139   -3.1265    0.1539 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6211   -1.6099   -0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1536   -1.9022   -1.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7468    0.2992   -0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0593   -1.0503   -0.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1359   -3.2523    0.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062   -4.0615    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490   -1.3310    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7117   -3.1058    1.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0136   -2.4133    0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8989   -1.0311   -1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8245    0.4664    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5943   -0.0520    1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5202    3.0621    0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388    5.0098    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875    6.0962   -0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3209    0.2477    0.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9820    1.1225    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8194   -1.1021   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2772    0.6306   -1.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5777   -1.2378   -0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479   -1.3037    1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4270    0.5046    2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -2.3221    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139   -3.2290   -0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6145   -2.0128   -0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7125   -2.7172   -2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 15 28  2  0
 28 29  1  0
 29  4  1  0
 28  6  1  0
 14  8  2  0
 26 17  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  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      -3.483   1.509   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.483   4.176   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.531   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.804   5.923   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.713   2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.864   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.471   6.693   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.531   3.613   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.471   8.233   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.137   9.003   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.197   8.233   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.197   3.613   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.197   6.693   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.138   6.693   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       7.865   4.383   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.804   9.003   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -0.137  10.543   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       2.530   9.003   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -0.268   4.089   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -0.137   5.923   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.198   4.383   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    4    9                                                       
CONECT    4    3   13                                                       
CONECT    5    9   10                                                       
CONECT    6   10   11                                                       
CONECT    7   12   21                                                       
CONECT    8    1    2   11                                                  
CONECT    9    3    5   17                                                  
CONECT   10    5    6   18                                                  
CONECT   11    6    8   26                                                  
CONECT   12    7   14   27                                                  
CONECT   13    4   22   28                                                  
CONECT   14   12   15   23                                                  
CONECT   15   14   16   24                                                  
CONECT   16   15   20   25                                                  
CONECT   17    9   19   28                                                  
CONECT   18   10   19   26                                                  
CONECT   19   17   18   29                                                  
CONECT   20   16   27   29                                                  
CONECT   21    7                                                            
CONECT   22   13                                                            
CONECT   23   14                                                            
CONECT   24   15                                                            
CONECT   25   16                                                            
CONECT   26   11   18                                                       
CONECT   27   12   20                                                       
CONECT   28   13   17                                                       
CONECT   29   19   20                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   64    0
END

COMPND    HMDB0039039
HETATM    1  C1  UNL     1      -3.205  -3.249   1.101  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.958  -2.274   0.661  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.431  -2.298   0.955  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.462  -1.117  -0.126  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.801   0.130   0.700  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.763   1.075   0.220  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.724   2.447   0.235  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.619   3.081  -0.286  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.516   4.464  -0.302  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.389   5.037  -0.835  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.604   4.244  -1.338  1.00  0.00           C  
HETATM   12  O1  UNL     1       1.669   4.694  -1.843  1.00  0.00           O  
HETATM   13  O2  UNL     1       0.466   2.950  -1.302  1.00  0.00           O  
HETATM   14  C12 UNL     1      -0.582   2.338  -0.808  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.636   0.954  -0.816  1.00  0.00           C  
HETATM   16  O3  UNL     1       0.444   0.269  -1.358  1.00  0.00           O  
HETATM   17  C14 UNL     1       1.499  -0.082  -0.488  1.00  0.00           C  
HETATM   18  O4  UNL     1       2.700   0.428  -0.928  1.00  0.00           O  
HETATM   19  C15 UNL     1       3.731   0.160  -0.073  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.002  -0.199  -0.854  1.00  0.00           C  
HETATM   21  O5  UNL     1       6.035  -0.467   0.025  1.00  0.00           O  
HETATM   22  C17 UNL     1       3.453  -0.859   0.974  1.00  0.00           C  
HETATM   23  O6  UNL     1       2.940  -0.303   2.152  1.00  0.00           O  
HETATM   24  C18 UNL     1       2.594  -1.999   0.531  1.00  0.00           C  
HETATM   25  O7  UNL     1       3.314  -3.126   0.154  1.00  0.00           O  
HETATM   26  C19 UNL     1       1.621  -1.610  -0.559  1.00  0.00           C  
HETATM   27  O8  UNL     1       2.154  -1.902  -1.809  1.00  0.00           O  
HETATM   28  C20 UNL     1      -1.747   0.299  -0.293  1.00  0.00           C  
HETATM   29  O9  UNL     1      -2.059  -1.050  -0.175  1.00  0.00           O  
HETATM   30  H1  UNL     1      -2.136  -3.252   0.900  1.00  0.00           H  
HETATM   31  H2  UNL     1      -3.606  -4.062   1.663  1.00  0.00           H  
HETATM   32  H3  UNL     1      -5.749  -1.331   1.404  1.00  0.00           H  
HETATM   33  H4  UNL     1      -5.712  -3.106   1.636  1.00  0.00           H  
HETATM   34  H5  UNL     1      -6.014  -2.413   0.023  1.00  0.00           H  
HETATM   35  H6  UNL     1      -3.899  -1.031  -1.121  1.00  0.00           H  
HETATM   36  H7  UNL     1      -4.825   0.466   0.515  1.00  0.00           H  
HETATM   37  H8  UNL     1      -3.594  -0.052   1.772  1.00  0.00           H  
HETATM   38  H9  UNL     1      -3.520   3.062   0.636  1.00  0.00           H  
HETATM   39  H10 UNL     1      -2.339   5.010   0.111  1.00  0.00           H  
HETATM   40  H11 UNL     1      -0.288   6.096  -0.859  1.00  0.00           H  
HETATM   41  H12 UNL     1       1.321   0.248   0.551  1.00  0.00           H  
HETATM   42  H13 UNL     1       3.982   1.123   0.459  1.00  0.00           H  
HETATM   43  H14 UNL     1       4.819  -1.102  -1.479  1.00  0.00           H  
HETATM   44  H15 UNL     1       5.277   0.631  -1.532  1.00  0.00           H  
HETATM   45  H16 UNL     1       6.578  -1.238  -0.308  1.00  0.00           H  
HETATM   46  H17 UNL     1       4.448  -1.304   1.275  1.00  0.00           H  
HETATM   47  H18 UNL     1       3.427   0.505   2.416  1.00  0.00           H  
HETATM   48  H19 UNL     1       1.955  -2.322   1.404  1.00  0.00           H  
HETATM   49  H20 UNL     1       3.214  -3.229  -0.824  1.00  0.00           H  
HETATM   50  H21 UNL     1       0.614  -2.013  -0.405  1.00  0.00           H  
HETATM   51  H22 UNL     1       1.713  -2.717  -2.200  1.00  0.00           H  
CONECT    1    2    2   30   31
CONECT    2    3    4
CONECT    3   32   33   34
CONECT    4    5   29   35
CONECT    5    6   36   37
CONECT    6    7    7   28
CONECT    7    8   38
CONECT    8    9   14   14
CONECT    9   10   10   39
CONECT   10   11   40
CONECT   11   12   12   13
CONECT   13   14
CONECT   14   15
CONECT   15   16   28   28
CONECT   16   17
CONECT   17   18   26   41
CONECT   18   19
CONECT   19   20   22   42
CONECT   20   21   43   44
CONECT   21   45
CONECT   22   23   24   46
CONECT   23   47
CONECT   24   25   26   48
CONECT   25   49
CONECT   26   27   50
CONECT   27   51
CONECT   28   29
END

HMDB0039039
     RDKit          3D
(R)-Apiumetin glucoside
 51 54  0  0  0  0  0  0  0  0999 V2000
   -3.2055   -3.2488    1.1011 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9576   -2.2743    0.6609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4307   -2.2983    0.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4624   -1.1171   -0.1255 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8012    0.1304    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7629    1.0748    0.2196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    2.4467    0.2347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6191    3.0806   -0.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5162    4.4640   -0.3022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3895    5.0371   -0.8353 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6044    4.2437   -1.3375 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6690    4.6936   -1.8435 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4664    2.9495   -1.3025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5819    2.3379   -0.8085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6359    0.9536   -0.8164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4439    0.2686   -1.3578 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4987   -0.0819   -0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6997    0.4283   -0.9281 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7314    0.1604   -0.0728 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0017   -0.1992   -0.8543 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0350   -0.4671    0.0251 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4534   -0.8594    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9399   -0.3029    2.1524 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5941   -1.9986    0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3139   -3.1265    0.1539 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6211   -1.6099   -0.5591 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1536   -1.9022   -1.8094 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7468    0.2992   -0.2931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0593   -1.0503   -0.1746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1359   -3.2523    0.9001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6062   -4.0615    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7490   -1.3310    1.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7117   -3.1058    1.6357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0136   -2.4133    0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8989   -1.0311   -1.1205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8245    0.4664    0.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5943   -0.0520    1.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5202    3.0621    0.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3388    5.0098    0.1108 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875    6.0962   -0.8586 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3209    0.2477    0.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9820    1.1225    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8194   -1.1021   -1.4785 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2772    0.6306   -1.5324 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5777   -1.2378   -0.3081 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479   -1.3037    1.2752 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4270    0.5046    2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9548   -2.3221    1.4044 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2139   -3.2290   -0.8238 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6145   -2.0128   -0.4054 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7125   -2.7172   -2.2003 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 19 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  0
 15 28  2  0
 28 29  1  0
 29  4  1  0
 28  6  1  0
 14  8  2  0
 26 17  1  0
  1 30  1  0
  1 31  1  0
  3 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  5 36  1  0
  5 37  1  0
  7 38  1  0
  9 39  1  0
 10 40  1  0
 17 41  1  0
 19 42  1  0
 20 43  1  0
 20 44  1  0
 21 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  0
 25 49  1  0
 26 50  1  0
 27 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-2,3-dihydro-9-O-beta-Glucosyloxy-2-isopropenyl-7H-furo[3,2-g][1]benzopyran-7-one	HMDB

Chemical Formula

C₂₀H₂₂O₉

Average Molecular Weight

406.3833

Monoisotopic Molecular Weight

406.126382302

IUPAC Name

2-(prop-1-en-2-yl)-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H,7H-furo[3,2-g]chromen-7-one

Traditional Name

2-(prop-1-en-2-yl)-9-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H,3H-furo[3,2-g]chromen-7-one

CAS Registry Number

115356-05-3

SMILES

CC(=C)C1CC2=C(O1)C(OC1OC(CO)C(O)C(O)C1O)=C1OC(=O)C=CC1=C2

InChI Identifier

InChI=1S/C20H22O9/c1-8(2)11-6-10-5-9-3-4-13(22)28-17(9)19(18(10)26-11)29-20-16(25)15(24)14(23)12(7-21)27-20/h3-5,11-12,14-16,20-21,23-25H,1,6-7H2,2H3

InChI Key

VPAPSBNFWBXZLU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Coumarin glycosides

Direct Parent

Coumarin glycosides

Alternative Parents

Substituents

Coumarin o-glycoside
Coumarin-8-o-glycoside
Phenolic glycoside
Furanocoumarin
Linear furanocoumarin
Psoralen
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Coumaran
Alkyl aryl ether
Pyranone
Benzenoid
Monosaccharide
Pyran
Oxane
Heteroaromatic compound
Secondary alcohol
Lactone
Acetal
Organoheterocyclic compound
Oxacycle
Ether
Polyol
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Primary alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039039)
Cytoplasm (HMDB: HMDB0039039)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039039)

Source

Exogenous

Exogenous (HMDB: HMDB0039039)

Food

Food (HMDB: HMDB0039039)

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Endogenous

Plant

Plant (HMDB: HMDB0039039)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039039)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	165 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	517 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	2.51 g/L	ALOGPS
logP	0	ALOGPS
logP	0.13	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	134.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	98.56 m³·mol⁻¹	ChemAxon
Polarizability	40.23 Å³	ChemAxon
Number of Rings	4	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]+	194.133	31661259
DarkChem	[M-H]-	190.888	31661259
DeepCCS	[M+H]+	193.35	30932474
DeepCCS	[M-H]-	190.992	30932474
DeepCCS	[M-2H]-	225.278	30932474
DeepCCS	[M+Na]+	200.767	30932474
AllCCS	[M+H]+	195.0	32859911
AllCCS	[M+H-H2O]+	192.3	32859911
AllCCS	[M+NH4]+	197.4	32859911
AllCCS	[M+Na]+	198.1	32859911
AllCCS	[M-H]-	194.3	32859911
AllCCS	[M+Na-2H]-	194.4	32859911
AllCCS	[M+HCOO]-	194.7	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.	4.21 minutes	32390414
Predicted by Siyang on May 30, 2022	11.0323 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.66 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	103.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1451.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	210.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	120.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	182.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	66.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	338.8 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	382.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	188.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	719.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	360.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1212.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	227.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	258.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	411.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	360.5 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	43.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-Apiumetin glucoside	CC(=C)C1CC2=C(O1)C(OC1OC(CO)C(O)C(O)C1O)=C1OC(=O)C=CC1=C2	3746.3	Standard polar	33892256
(R)-Apiumetin glucoside	CC(=C)C1CC2=C(O1)C(OC1OC(CO)C(O)C(O)C1O)=C1OC(=O)C=CC1=C2	3299.9	Standard non polar	33892256
(R)-Apiumetin glucoside	CC(=C)C1CC2=C(O1)C(OC1OC(CO)C(O)C(O)C1O)=C1OC(=O)C=CC1=C2	3685.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-Apiumetin glucoside,1TMS,isomer #1	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O)=C2O1	3456.1	Semi standard non polar	33892256
(R)-Apiumetin glucoside,1TMS,isomer #2	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O)=C2O1	3462.8	Semi standard non polar	33892256
(R)-Apiumetin glucoside,1TMS,isomer #3	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O)=C2O1	3482.0	Semi standard non polar	33892256
(R)-Apiumetin glucoside,1TMS,isomer #4	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C)=C2O1	3460.8	Semi standard non polar	33892256
(R)-Apiumetin glucoside,2TMS,isomer #1	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O)=C2O1	3399.8	Semi standard non polar	33892256
(R)-Apiumetin glucoside,2TMS,isomer #2	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O)=C2O1	3425.2	Semi standard non polar	33892256
(R)-Apiumetin glucoside,2TMS,isomer #3	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C)C(O)C(O)C3O[Si](C)(C)C)=C2O1	3390.1	Semi standard non polar	33892256
(R)-Apiumetin glucoside,2TMS,isomer #4	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)=C2O1	3409.7	Semi standard non polar	33892256
(R)-Apiumetin glucoside,2TMS,isomer #5	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)=C2O1	3406.1	Semi standard non polar	33892256
(R)-Apiumetin glucoside,2TMS,isomer #6	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)=C2O1	3416.0	Semi standard non polar	33892256
(R)-Apiumetin glucoside,3TMS,isomer #1	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)=C2O1	3392.7	Semi standard non polar	33892256
(R)-Apiumetin glucoside,3TMS,isomer #2	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)=C2O1	3393.3	Semi standard non polar	33892256
(R)-Apiumetin glucoside,3TMS,isomer #3	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)=C2O1	3381.9	Semi standard non polar	33892256
(R)-Apiumetin glucoside,3TMS,isomer #4	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)=C2O1	3368.0	Semi standard non polar	33892256
(R)-Apiumetin glucoside,4TMS,isomer #1	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)=C2O1	3386.6	Semi standard non polar	33892256
(R)-Apiumetin glucoside,1TBDMS,isomer #1	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O)=C2O1	3673.4	Semi standard non polar	33892256
(R)-Apiumetin glucoside,1TBDMS,isomer #2	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)=C2O1	3691.0	Semi standard non polar	33892256
(R)-Apiumetin glucoside,1TBDMS,isomer #3	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)=C2O1	3701.6	Semi standard non polar	33892256
(R)-Apiumetin glucoside,1TBDMS,isomer #4	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)=C2O1	3685.3	Semi standard non polar	33892256
(R)-Apiumetin glucoside,2TBDMS,isomer #1	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)=C2O1	3837.2	Semi standard non polar	33892256
(R)-Apiumetin glucoside,2TBDMS,isomer #2	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)=C2O1	3853.1	Semi standard non polar	33892256
(R)-Apiumetin glucoside,2TBDMS,isomer #3	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)=C2O1	3826.2	Semi standard non polar	33892256
(R)-Apiumetin glucoside,2TBDMS,isomer #4	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)=C2O1	3849.4	Semi standard non polar	33892256
(R)-Apiumetin glucoside,2TBDMS,isomer #5	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)=C2O1	3854.0	Semi standard non polar	33892256
(R)-Apiumetin glucoside,2TBDMS,isomer #6	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)=C2O1	3854.2	Semi standard non polar	33892256
(R)-Apiumetin glucoside,3TBDMS,isomer #1	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)=C2O1	4014.7	Semi standard non polar	33892256
(R)-Apiumetin glucoside,3TBDMS,isomer #2	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)=C2O1	4029.6	Semi standard non polar	33892256
(R)-Apiumetin glucoside,3TBDMS,isomer #3	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)=C2O1	3990.3	Semi standard non polar	33892256
(R)-Apiumetin glucoside,3TBDMS,isomer #4	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)=C2O1	3978.6	Semi standard non polar	33892256
(R)-Apiumetin glucoside,4TBDMS,isomer #1	C=C(C)C1CC2=CC3=C(OC(=O)C=C3)C(OC3OC(CO[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)=C2O1	4191.1	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 - (R)-Apiumetin glucoside GC-MS (Non-derivatized) - 70eV, Positive	splash10-059i-8219000000-17910f8be6c3344d3b5a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Apiumetin glucoside GC-MS (4 TMS) - 70eV, Positive	splash10-0059-1121109000-e55d1832dbe6419fa2ad	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-Apiumetin glucoside 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 - (R)-Apiumetin glucoside 10V, Positive-QTOF	splash10-052b-0193300000-5afa41100aa159f2f7b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin glucoside 20V, Positive-QTOF	splash10-0002-0490000000-52590c4294ad9bf6484b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin glucoside 40V, Positive-QTOF	splash10-0f95-4690000000-83b3d59c36350a3acc2c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin glucoside 10V, Negative-QTOF	splash10-0a4l-2566900000-9c9a920e443ba73586a2	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin glucoside 20V, Negative-QTOF	splash10-0007-1691000000-36880190142779d76e9c	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin glucoside 40V, Negative-QTOF	splash10-0005-5950000000-0c9830dbd6ff6c33e9bc	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin glucoside 10V, Negative-QTOF	splash10-0a4i-0000900000-375482ee149d5b8f1eb0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin glucoside 20V, Negative-QTOF	splash10-0a4l-1096300000-7e86ed6ee5b3f9145e88	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin glucoside 40V, Negative-QTOF	splash10-0fb9-1790000000-05415fa6d85a98a92c2e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin glucoside 10V, Positive-QTOF	splash10-0002-0090000000-4fffaf6eeac8a5102257	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin glucoside 20V, Positive-QTOF	splash10-0002-0090000000-64b942d40eb28ee65a84	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-Apiumetin glucoside 40V, Positive-QTOF	splash10-052k-4493000000-554e4707ba9f8241b5b0	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018536

KNApSAcK ID

C00019835

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

14033997

PDB ID

Not Available

ChEBI ID

176002

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1873731

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 (R)-Apiumetin glucoside (HMDB0039039)

MOL for HMDB0039039 ((R)-Apiumetin glucoside)

3D MOL for HMDB0039039 ((R)-Apiumetin glucoside)

3D SDF for HMDB0039039 ((R)-Apiumetin glucoside)

3D-SDF for HMDB0039039 ((R)-Apiumetin glucoside)

PDB for HMDB0039039 ((R)-Apiumetin glucoside)

3D PDB for HMDB0039039 ((R)-Apiumetin glucoside)

SMILES for HMDB0039039 ((R)-Apiumetin glucoside)

INCHI for HMDB0039039 ((R)-Apiumetin glucoside)

Structure for HMDB0039039 ((R)-Apiumetin glucoside)

3D Structure for HMDB0039039 ((R)-Apiumetin glucoside)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra