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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-24 05:53:15 UTC

Update Date

2022-09-22 18:35:00 UTC

HMDB ID

HMDB0303946

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(-)-maackiain-3-O-glucoside

Description

(-)-maackiain-3-o-glucoside, also known as trifolrhizin, is a member of the class of compounds known as pterocarpans. Pterocarpans are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids (-)-maackiain-3-o-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). (-)-maackiain-3-o-glucoside can be found in a number of food items such as pepper (c. pubescens), loquat, nopal, and kiwi, which makes (-)-maackiain-3-o-glucoside a potential biomarker for the consumption of these food products.

Structure

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


  Mrv1533007131514022D          

 39 44  0  0  1  0            999 V2000
    0.9678    2.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    2.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    0.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0867    2.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867   -0.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743    0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405    1.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059    1.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    1.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292    1.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    1.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8901    0.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3582    2.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7573    1.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7863    2.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7637   -0.0049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3025   -0.6890    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4795   -0.6316    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1177    0.1098    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0749    1.7647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5789    0.7938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9485   -0.8037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6644   -1.4304    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0184   -1.3157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7053    0.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    0.2819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5325    0.9754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5794    2.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    1.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5830    2.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4019    0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7131    1.0233    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1255   -0.7464    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8414   -1.3731    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3435   -0.5743    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6878    2.4932    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2441    0.8512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  9  1  1  0  0  0  0
  9  3  2  0  0  0  0
 10  2  1  0  0  0  0
 11  4  2  0  0  0  0
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 13  3  1  0  0  0  0
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 20 37  1  1  0  0  0
 21 38  1  1  0  0  0
 22 39  1  6  0  0  0
M  END

HMDB0303946
     RDKit          3D
(-)-maackiain-3-O-glucoside
 54 59  0  0  0  0  0  0  0  0999 V2000
   -7.4660    0.4803    2.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5013   -0.4101    1.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1287    0.2618    1.4757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2045   -0.6456    1.0513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574   -0.2318   -0.0482 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6006   -1.2565   -0.3930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555   -1.3050   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510   -2.4887   -0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243   -2.5577   -0.9978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5319   -1.4475   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9311   -0.2666   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4561   -0.2177   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7561    0.8249   -0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682    0.9929   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6795   -0.2434   -1.2113 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8710   -0.1290   -0.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9024    0.7636   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8281   -0.3743    1.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7862   -1.2748    1.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9438   -0.2736    2.3792 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.0467    1.3993    0.8917 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.2566    2.4458    1.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0176    0.7446    1.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8936    0.6960    0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2317   -3.3989   -1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.4993    1.8194   -0.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7213   -2.0879    2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2394   -0.7491   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8143   -0.8062   -2.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
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 21 16  1  0
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  1 33  1  0
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  5 37  1  1
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 12 40  1  0
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 28 50  1  0
 29 51  1  6
 30 52  1  0
 31 53  1  6
 32 54  1  0
M  END


  Mrv1533007131514022D          

 39 44  0  0  1  0            999 V2000
    0.9678    2.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    2.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    0.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0867    2.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867   -0.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743    0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405    1.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059    1.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    1.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292    1.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    1.0807    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8901    0.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3582    2.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7573    1.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7863    2.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7637   -0.0049    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.1177    0.1098    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0749    1.7647    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5789    0.7938    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9485   -0.8037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.2441    0.8512    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  9  1  1  0  0  0  0
  9  3  2  0  0  0  0
 10  2  1  0  0  0  0
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 22 20  1  0  0  0  0
 23  6  1  0  0  0  0
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 27  7  1  0  0  0  0
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 31 14  1  0  0  0  0
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 12 33  1  1  0  0  0
 17 34  1  6  0  0  0
 18 35  1  1  0  0  0
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 22 39  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0303946

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12COC3=C(C=CC(O[C@]4([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]4([H])O)=C3)[C@]1([H])OC1=CC3=C(OCO3)C=C21

> <INCHI_IDENTIFIER>
InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2/t12-,17+,18+,19-,20+,21-,22+/m0/s1

> <INCHI_KEY>
VGSYCWGXBYZLLE-QEEQPWONSA-N

> <FORMULA>
C22H22O10

> <MOLECULAR_WEIGHT>
446.408

> <EXACT_MASS>
446.121296908

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
43.94438071422702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-16-yloxy]oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.70

> <JCHEM_LOGP>
0.022060036333333283

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.196090792974335

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.200140018647128

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810923437225645

> <JCHEM_POLAR_SURFACE_AREA>
136.3

> <JCHEM_REFRACTIVITY>
104.50919999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
trifolirhizin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303946
     RDKit          3D
(-)-maackiain-3-O-glucoside
 54 59  0  0  0  0  0  0  0  0999 V2000
   -7.4660    0.4803    2.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5013   -0.4101    1.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1287    0.2618    1.4757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2045   -0.6456    1.0513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574   -0.2318   -0.0482 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6006   -1.2565   -0.3930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555   -1.3050   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510   -2.4887   -0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243   -2.5577   -0.9978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5319   -1.4475   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9311   -0.2666   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4561   -0.2177   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7561    0.8249   -0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682    0.9929   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6795   -0.2434   -1.2113 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8710   -0.1290   -0.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9024    0.7636   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8988    0.6576    0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8281   -0.3743    1.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7862   -1.2748    1.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7690   -1.1714    0.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6229   -1.9229    0.3211 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0086   -1.5247   -0.8802 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9438   -0.2736    2.3792 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6259    0.9277    2.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0467    1.3993    0.8917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4942    0.0595   -1.1451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8980    0.0869   -2.3971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1053    1.3818   -0.7752 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3083    1.6153   -1.4288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1974    1.5320    0.7095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2566    2.4458    1.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0176    0.7446    1.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3486   -1.2281    2.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8098   -0.8959    0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8635    0.5292    2.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8936    0.6960    0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2317   -3.3989   -1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732   -3.4938   -1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884    0.7158    0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4993    1.8194   -0.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091    1.3227   -2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0636   -0.2900   -2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9770    1.5846   -1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7213   -2.0879    2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -2.2962   -1.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5101    1.6493    2.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7155    0.7475    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2394   -0.7491   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8143   -0.8062   -2.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3901    2.1719   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5723    2.5544   -1.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2028    2.0006    0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9272    3.0223    0.4795 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  2  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  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
  5 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31  3  1  0
 12  7  1  0
 23 15  1  0
 23 10  1  0
 21 16  1  0
 26 18  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  1
  5 37  1  1
  8 38  1  0
  9 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  6
 17 44  1  0
 20 45  1  0
 23 46  1  6
 25 47  1  0
 25 48  1  0
 27 49  1  6
 28 50  1  0
 29 51  1  6
 30 52  1  0
 31 53  1  6
 32 54  1  0
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       1.806   4.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.343   4.464   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.992   1.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.387   1.625   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.495   4.703   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.829  -0.116   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.925   0.633   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.142   3.034   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.131   2.973   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.204   3.187   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.081   2.441   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.601   2.017   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.528   1.803   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.135   3.980   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.747   2.348   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.801   3.887   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.292  -0.009   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.431  -1.286   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.895  -1.179   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.220   0.205   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.740   3.294   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.081   1.482   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -5.504  -1.500   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -3.107  -2.670   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -0.034  -2.456   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       1.317   0.312   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       4.389   0.526   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      12.194   1.821   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      12.281   4.311   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.405   2.866   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       6.688   4.507   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -2.617   1.375   0.000  0.00  0.00           O+0
HETATM   33  H   UNK     0       5.065   1.910   0.000  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.968  -1.393   0.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.571  -2.563   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.756   0.098   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.641  -1.072   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0       5.017   4.654   0.000  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.456   1.589   0.000  0.00  0.00           H+0
CONECT    1    2    9                                                       
CONECT    2    1   10                                                       
CONECT    3    9   13                                                       
CONECT    4   11   15                                                       
CONECT    5   14   16                                                       
CONECT    6   17   23                                                       
CONECT    7   12   27                                                       
CONECT    8   28   29                                                       
CONECT    9    1    3   30                                                  
CONECT   10    2   13   21                                                  
CONECT   11    4   12   14                                                  
CONECT   12    7   11   21   33                                             
CONECT   13    3   10   27                                                  
CONECT   14    5   11   31                                                  
CONECT   15    4   16   28                                                  
CONECT   16    5   15   29                                                  
CONECT   17    6   18   32   34                                             
CONECT   18   17   19   24   35                                             
CONECT   19   18   20   25   36                                             
CONECT   20   19   22   26   37                                             
CONECT   21   10   12   31   38                                             
CONECT   22   20   30   32   39                                             
CONECT   23    6                                                            
CONECT   24   18                                                            
CONECT   25   19                                                            
CONECT   26   20                                                            
CONECT   27    7   13                                                       
CONECT   28    8   15                                                       
CONECT   29    8   16                                                       
CONECT   30    9   22                                                       
CONECT   31   14   21                                                       
CONECT   32   17   22                                                       
CONECT   33   12                                                            
CONECT   34   17                                                            
CONECT   35   18                                                            
CONECT   36   19                                                            
CONECT   37   20                                                            
CONECT   38   21                                                            
CONECT   39   22                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   88    0
END

COMPND    HMDB0303946
HETATM    1  O1  UNL     1      -7.466   0.480   2.023  1.00  0.00           O  
HETATM    2  C1  UNL     1      -6.501  -0.410   1.594  1.00  0.00           C  
HETATM    3  C2  UNL     1      -5.129   0.262   1.476  1.00  0.00           C  
HETATM    4  O2  UNL     1      -4.205  -0.646   1.051  1.00  0.00           O  
HETATM    5  C3  UNL     1      -3.457  -0.232  -0.048  1.00  0.00           C  
HETATM    6  O3  UNL     1      -2.601  -1.256  -0.393  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.255  -1.305  -0.507  1.00  0.00           C  
HETATM    8  C5  UNL     1      -0.651  -2.489  -0.876  1.00  0.00           C  
HETATM    9  C6  UNL     1       0.724  -2.558  -0.998  1.00  0.00           C  
HETATM   10  C7  UNL     1       1.532  -1.448  -0.754  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.931  -0.267  -0.385  1.00  0.00           C  
HETATM   12  C9  UNL     1      -0.456  -0.218  -0.268  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.756   0.825  -0.148  1.00  0.00           O  
HETATM   14  C10 UNL     1       2.868   0.993  -1.042  1.00  0.00           C  
HETATM   15  C11 UNL     1       3.679  -0.243  -1.211  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.871  -0.129  -0.324  1.00  0.00           C  
HETATM   17  C13 UNL     1       5.902   0.764  -0.301  1.00  0.00           C  
HETATM   18  C14 UNL     1       6.899   0.658   0.631  1.00  0.00           C  
HETATM   19  C15 UNL     1       6.828  -0.374   1.542  1.00  0.00           C  
HETATM   20  C16 UNL     1       5.786  -1.275   1.519  1.00  0.00           C  
HETATM   21  C17 UNL     1       4.769  -1.171   0.572  1.00  0.00           C  
HETATM   22  O5  UNL     1       3.623  -1.923   0.321  1.00  0.00           O  
HETATM   23  C18 UNL     1       3.009  -1.525  -0.880  1.00  0.00           C  
HETATM   24  O6  UNL     1       7.944  -0.274   2.379  1.00  0.00           O  
HETATM   25  C19 UNL     1       8.626   0.928   2.075  1.00  0.00           C  
HETATM   26  O7  UNL     1       8.047   1.399   0.892  1.00  0.00           O  
HETATM   27  C20 UNL     1      -4.494   0.059  -1.145  1.00  0.00           C  
HETATM   28  O8  UNL     1      -3.898   0.087  -2.397  1.00  0.00           O  
HETATM   29  C21 UNL     1      -5.105   1.382  -0.775  1.00  0.00           C  
HETATM   30  O9  UNL     1      -6.308   1.615  -1.429  1.00  0.00           O  
HETATM   31  C22 UNL     1      -5.197   1.532   0.710  1.00  0.00           C  
HETATM   32  O10 UNL     1      -4.257   2.446   1.216  1.00  0.00           O  
HETATM   33  H1  UNL     1      -8.018   0.745   1.229  1.00  0.00           H  
HETATM   34  H2  UNL     1      -6.349  -1.228   2.357  1.00  0.00           H  
HETATM   35  H3  UNL     1      -6.810  -0.896   0.670  1.00  0.00           H  
HETATM   36  H4  UNL     1      -4.864   0.529   2.541  1.00  0.00           H  
HETATM   37  H5  UNL     1      -2.894   0.696   0.164  1.00  0.00           H  
HETATM   38  H6  UNL     1      -1.232  -3.399  -1.082  1.00  0.00           H  
HETATM   39  H7  UNL     1       1.173  -3.494  -1.288  1.00  0.00           H  
HETATM   40  H8  UNL     1      -0.888   0.716   0.022  1.00  0.00           H  
HETATM   41  H9  UNL     1       3.499   1.819  -0.658  1.00  0.00           H  
HETATM   42  H10 UNL     1       2.509   1.323  -2.040  1.00  0.00           H  
HETATM   43  H11 UNL     1       4.064  -0.290  -2.257  1.00  0.00           H  
HETATM   44  H12 UNL     1       5.977   1.585  -1.011  1.00  0.00           H  
HETATM   45  H13 UNL     1       5.721  -2.088   2.229  1.00  0.00           H  
HETATM   46  H14 UNL     1       3.217  -2.296  -1.673  1.00  0.00           H  
HETATM   47  H15 UNL     1       8.510   1.649   2.911  1.00  0.00           H  
HETATM   48  H16 UNL     1       9.715   0.747   1.902  1.00  0.00           H  
HETATM   49  H17 UNL     1      -5.239  -0.749  -1.147  1.00  0.00           H  
HETATM   50  H18 UNL     1      -3.814  -0.806  -2.796  1.00  0.00           H  
HETATM   51  H19 UNL     1      -4.390   2.172  -1.151  1.00  0.00           H  
HETATM   52  H20 UNL     1      -6.572   2.554  -1.200  1.00  0.00           H  
HETATM   53  H21 UNL     1      -6.203   2.001   0.927  1.00  0.00           H  
HETATM   54  H22 UNL     1      -3.927   3.022   0.479  1.00  0.00           H  
CONECT    1    2   33
CONECT    2    3   34   35
CONECT    3    4   31   36
CONECT    4    5
CONECT    5    6   27   37
CONECT    6    7
CONECT    7    8    8   12
CONECT    8    9   38
CONECT    9   10   10   39
CONECT   10   11   23
CONECT   11   12   12   13
CONECT   12   40
CONECT   13   14
CONECT   14   15   41   42
CONECT   15   16   23   43
CONECT   16   17   17   21
CONECT   17   18   44
CONECT   18   19   19   26
CONECT   19   20   24
CONECT   20   21   21   45
CONECT   21   22
CONECT   22   23
CONECT   23   46
CONECT   24   25
CONECT   25   26   47   48
CONECT   27   28   29   49
CONECT   28   50
CONECT   29   30   31   51
CONECT   30   52
CONECT   31   32   53
CONECT   32   54
END

HMDB0303946
     RDKit          3D
(-)-maackiain-3-O-glucoside
 54 59  0  0  0  0  0  0  0  0999 V2000
   -7.4660    0.4803    2.0227 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5013   -0.4101    1.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1287    0.2618    1.4757 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2045   -0.6456    1.0513 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4574   -0.2318   -0.0482 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6006   -1.2565   -0.3930 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2555   -1.3050   -0.5067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6510   -2.4887   -0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7243   -2.5577   -0.9978 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5319   -1.4475   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9311   -0.2666   -0.3854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4561   -0.2177   -0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7561    0.8249   -0.1483 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8682    0.9929   -1.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6795   -0.2434   -1.2113 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.8710   -0.1290   -0.3236 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9024    0.7636   -0.3015 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8988    0.6576    0.6305 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8281   -0.3743    1.5420 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7862   -1.2748    1.5186 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7690   -1.1714    0.5716 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6229   -1.9229    0.3211 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0086   -1.5247   -0.8802 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.9438   -0.2736    2.3792 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6259    0.9277    2.0753 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0467    1.3993    0.8917 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4942    0.0595   -1.1451 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8980    0.0869   -2.3971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1053    1.3818   -0.7752 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.3083    1.6153   -1.4288 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1974    1.5320    0.7095 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2566    2.4458    1.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0176    0.7446    1.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3486   -1.2281    2.3567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8098   -0.8959    0.6704 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8635    0.5292    2.5405 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8936    0.6960    0.1639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2317   -3.3989   -1.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1732   -3.4938   -1.2878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8884    0.7158    0.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4993    1.8194   -0.6579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5091    1.3227   -2.0401 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0636   -0.2900   -2.2569 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9770    1.5846   -1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7213   -2.0879    2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2169   -2.2962   -1.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5101    1.6493    2.9113 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7155    0.7475    1.9022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2394   -0.7491   -1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8143   -0.8062   -2.7962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3901    2.1719   -1.1507 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5723    2.5544   -1.1996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2028    2.0006    0.9266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9272    3.0223    0.4795 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  2  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  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 19 24  1  0
 24 25  1  0
 25 26  1  0
  5 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31  3  1  0
 12  7  1  0
 23 15  1  0
 23 10  1  0
 21 16  1  0
 26 18  1  0
  1 33  1  0
  2 34  1  0
  2 35  1  0
  3 36  1  1
  5 37  1  1
  8 38  1  0
  9 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  6
 17 44  1  0
 20 45  1  0
 23 46  1  6
 25 47  1  0
 25 48  1  0
 27 49  1  6
 28 50  1  0
 29 51  1  6
 30 52  1  0
 31 53  1  6
 32 54  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Maackiain 3-O-glucoside	Kegg

Chemical Formula

C₂₂H₂₂O₁₀

Average Molecular Weight

446.408

Monoisotopic Molecular Weight

446.121296908

IUPAC Name

(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(1R,12R)-5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-16-yloxy]oxane-3,4,5-triol

Traditional Name

trifolirhizin

CAS Registry Number

Not Available

SMILES

[H][C@@]12COC3=C(C=CC(O[C@]4([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]4([H])O)=C3)[C@]1([H])OC1=CC3=C(OCO3)C=C21

InChI Identifier

InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2/t12-,17+,18+,19-,20+,21-,22+/m0/s1

InChI Key

VGSYCWGXBYZLLE-QEEQPWONSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Pterocarpan
Isoflavanol
Isoflavan
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Coumaran
Benzodioxole
Benzofuran
Alkyl aryl ether
Benzenoid
Monosaccharide
Oxane
Secondary alcohol
Polyol
Ether
Acetal
Organoheterocyclic compound
Oxacycle
Primary alcohol
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

pterocarpans (CHEBI:9714 )
pterocarpans (C10538 )
Pterocarpanes (C10538 )

Ontology

Not Available

Exogenous (HMDB: HMDB0303946)

Herbs and Spices (FooDB: FOOD00866)

Nut

Almond (FooDB: FOOD00148)
Brazil nut (FooDB: FOOD00024)
Cashew nut (FooDB: FOOD00011)
Chestnut (FooDB: FOOD00045)
Hazelnut (FooDB: FOOD00376)
Peanut (FooDB: FOOD00016)
Pecan nut (FooDB: FOOD00044)
Pine nut (FooDB: FOOD00138)
Pistachio (FooDB: FOOD00140)
Walnut (FooDB: FOOD00608)
Acorn (FooDB: FOOD00282)
Beech nut (FooDB: FOOD00299)
Butternut (FooDB: FOOD00316)
Chinese chestnut (FooDB: FOOD00331)
European chestnut (FooDB: FOOD00363)
Hickory nut (FooDB: FOOD00377)
Macadamia nut (FooDB: FOOD00525)
Mixed nuts (FooDB: FOOD00771)
Pili nut (FooDB: FOOD00432)
Colorado pinyon (FooDB: FOOD00433)
Black walnut (FooDB: FOOD00093)
Common walnut (FooDB: FOOD00094)
Japanese chestnut (FooDB: FOOD00385)
Common hazelnut (FooDB: FOOD00062)
Macadamia nut (M. tetraphylla) (FooDB: FOOD00225)
Japanese walnut (FooDB: FOOD00240)
Nuts (FooDB: FOOD00869)

Fruit

Pome

Drupe

Apricot (FooDB: FOOD00144)
Prunus (Cherry, Plum) (FooDB: FOOD00143)
Nectarine (FooDB: FOOD00229)
Peach (FooDB: FOOD00149)
European plum (FooDB: FOOD00147)
Sour cherry (FooDB: FOOD00146)
Sweet cherry (FooDB: FOOD00145)
Common chokecherry (FooDB: FOOD00562)
Peach (var.) (FooDB: FOOD00230)

Tropical fruit

Berry

Bilberry (FooDB: FOOD00193)
Rubus (Blackberry, Raspberry) (FooDB: FOOD00160)
Vaccinium (Blueberry, Cranberry, Huckleberry) (FooDB: FOOD00188)
Blackcurrant (FooDB: FOOD00155)
Redcurrant (FooDB: FOOD00156)
Elderberry (FooDB: FOOD00358)
Gooseberry (FooDB: FOOD00157)
Grape (FooDB: FOOD00369)
Lingonberry (FooDB: FOOD00194)
Loganberry (FooDB: FOOD00400)
Strawberry (FooDB: FOOD00083)
Boysenberry (FooDB: FOOD00542)
American cranberry (FooDB: FOOD00192)
Common grape (FooDB: FOOD00204)
Strawberry guava (FooDB: FOOD00482)
Black mulberry (FooDB: FOOD00117)
Red raspberry (FooDB: FOOD00162)
Muscadine grape (FooDB: FOOD00203)
Salmonberry (FooDB: FOOD00456)
Alaska blueberry (FooDB: FOOD00380)
Sea-buckthornberry (FooDB: FOOD00087)
Black elderberry (FooDB: FOOD00166)
Black crowberry (FooDB: FOOD00075)
Black huckleberry (FooDB: FOOD00084)
Mulberry (FooDB: FOOD00116)
Black chokeberry (FooDB: FOOD00136)
Cloudberry (FooDB: FOOD00161)
Black raspberry (FooDB: FOOD00163)
Rowanberry (FooDB: FOOD00176)
Lowbush blueberry (FooDB: FOOD00189)
Sparkleberry (FooDB: FOOD00190)
Highbush blueberry (FooDB: FOOD00191)
Arctic blackberry (FooDB: FOOD00207)
Bayberry (FooDB: FOOD00209)
Elliott's blueberry (FooDB: FOOD00210)
Canada blueberry (FooDB: FOOD00211)
Bog bilberry (FooDB: FOOD00212)
Buffalo currant (FooDB: FOOD00213)
European cranberry (FooDB: FOOD00217)
Deerberry (FooDB: FOOD00218)
Cascade huckleberry (FooDB: FOOD00220)
Oval-leaf huckleberry (FooDB: FOOD00221)
Evergreen huckleberry (FooDB: FOOD00222)
Red huckleberry (FooDB: FOOD00223)
Summer grape (FooDB: FOOD00227)
Fox grape (FooDB: FOOD00228)
Half-highbush blueberry (FooDB: FOOD00248)
Jostaberry (FooDB: FOOD00257)
Sweet rowanberry (FooDB: FOOD00265)
Skunk currant (FooDB: FOOD00267)
Squashberry (FooDB: FOOD00344)
Ohelo berry (FooDB: FOOD00419)
Chinese bayberry (FooDB: FOOD00852)
Saskatoon berry (FooDB: FOOD00884)
Nanking cherry (FooDB: FOOD00885)

Other fruit

Date (FooDB: FOOD00135)
Fig (FooDB: FOOD00081)
Jujube (FooDB: FOOD00388)

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Persian lime (FooDB: FOOD00543)
Pummelo (FooDB: FOOD00055)
Grapefruit/Pummelo hybrid (FooDB: FOOD00255)
Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Vegetable

Shoot vegetable

Fruit vegetable

Eggplant (FooDB: FOOD00174)
Avocado (FooDB: FOOD00130)
Groundcherry (FooDB: FOOD00371)
Olive (FooDB: FOOD00121)
Pepper (FooDB: FOOD00040)
Garden tomato (FooDB: FOOD00171)
Mexican groundcherry (FooDB: FOOD00491)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Garden tomato (var.) (FooDB: FOOD00173)
Cherry tomato (FooDB: FOOD00172)
Pepper (C. baccatum) (FooDB: FOOD00231)
Pepper (C. chinense) (FooDB: FOOD00232)
Pepper (Capsicum) (FooDB: FOOD00233)
Pepper (C. frutescens) (FooDB: FOOD00428)
Pepper (C. pubescens) (FooDB: FOOD00849)
Orange bell pepper (FooDB: FOOD00879)

Root vegetable

Cabbage

Leaf vegetable

Lettuce (FooDB: FOOD00095)
Swiss chard (FooDB: FOOD00237)
Garden cress (FooDB: FOOD00099)
Endive (FooDB: FOOD00048)
Spinach (FooDB: FOOD00178)
Common beet (FooDB: FOOD00025)
Garland chrysanthemum (FooDB: FOOD00333)
Jute (FooDB: FOOD00389)
Lambsquarters (FooDB: FOOD00394)
New Zealand spinach (FooDB: FOOD00415)
Swamp cabbage (FooDB: FOOD00091)
Rocket salad (ssp.) (FooDB: FOOD00077)
Yautia (FooDB: FOOD00510)
Romaine lettuce (FooDB: FOOD00888)
Rocket salad (FooDB: FOOD00244)
Chicory leaves (FooDB: FOOD00250)
Corn salad (FooDB: FOOD00340)
Malabar spinach (FooDB: FOOD00404)
Ostrich fern (FooDB: FOOD00556)
Green vegetables (FooDB: FOOD00872)

Mushroom

Tuber

Onion-family vegetable

Leek (FooDB: FOOD00007)
Allium (FooDB: FOOD00005)
Wild leek (FooDB: FOOD00396)
Shallot (FooDB: FOOD00243)
Garden onion (FooDB: FOOD00006)
Garden onion (var.) (FooDB: FOOD00226)
Onion-family vegetables (FooDB: FOOD00855)
Green onion (FooDB: FOOD00963)
Red onion (FooDB: FOOD00962)

Other vegetable

Okra (FooDB: FOOD00420)
Horseradish tree (FooDB: FOOD00379)
Sacred lotus (FooDB: FOOD00402)
Tree fern (FooDB: FOOD00797)
Chinese water chestnut (FooDB: FOOD00332)
Nopal (FooDB: FOOD00416)
Carob (FooDB: FOOD00321)
Agave (FooDB: FOOD00563)
Narrowleaf cattail (FooDB: FOOD00564)
Giant butterbur (FooDB: FOOD00314)
Sesbania flower (FooDB: FOOD00469)

Stalk vegetable

Brassica

Brassicas (FooDB: FOOD00857)

Cereal and cereal product

Other bread

Other bread (FooDB: FOOD00269)

Cereal

Cereal product

Dough

Sourdough (FooDB: FOOD00275)

Cereals and cereal products (FooDB: FOOD00858)

Pulse

Bean

Lentil

Lentils (FooDB: FOOD00098)

Pea

Other pulse

White lupine (FooDB: FOOD00403)
Lupine (FooDB: FOOD00104)

Pulses (FooDB: FOOD00867)

Soy

Soy bean (FooDB: FOOD00085)

Soy product

Other soy product (FooDB: FOOD00271)

Abalone (FooDB: FOOD00279)
Conch (FooDB: FOOD00611)

Gourd

Chayote (FooDB: FOOD00325)
Cucumber (FooDB: FOOD00065)
Muskmelon (FooDB: FOOD00064)
Cucurbita (FooDB: FOOD00066)
Watermelon (FooDB: FOOD00052)
Bitter gourd (FooDB: FOOD00115)
Calabash (FooDB: FOOD00318)
Towel gourd (FooDB: FOOD00492)
Winter squash (FooDB: FOOD00283)
Butternut squash (FooDB: FOOD00317)
Wax gourd (FooDB: FOOD00499)
Green zucchini (FooDB: FOOD00875)
Yellow zucchini (FooDB: FOOD00876)
Japanese pumpkin (FooDB: FOOD00886)
Sunburst squash (pattypan squash) (FooDB: FOOD00874)
Tinda (FooDB: FOOD00559)
Horned melon (FooDB: FOOD00761)

Tea

Herbal tea

Greenthread tea (FooDB: FOOD00820)

Cocoa and cocoa product

Cocoa

Cocoa bean (FooDB: FOOD00182)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.7	ALOGPS
logP	0.022	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	12.2	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	136.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	104.51 m³·mol⁻¹	ChemAxon
Polarizability	43.94 Å³	ChemAxon
Number of Rings	6	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
AllCCS	[M+H]+	202.059	32859911
AllCCS	[M+H-H2O]+	199.869	32859911
AllCCS	[M+Na]+	204.639	32859911
AllCCS	[M+NH4]+	204.066	32859911
AllCCS	[M-H]-	199.815	32859911
AllCCS	[M+Na-2H]-	200.086	32859911
AllCCS	[M+HCOO]-	200.54	32859911
DeepCCS	[M-2H]-	233.573	30932474
DeepCCS	[M+Na]+	207.345	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.3012 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.25 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1808.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	233.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	144.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	198.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	92.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	353.4 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	444.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	376.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	786.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	429.5 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	1305.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	289.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	267.6 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	411.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	276.5 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	125.2 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-maackiain-3-O-glucoside 10V, Positive-QTOF	splash10-000j-0090400000-75ae044d090e725b8203	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-maackiain-3-O-glucoside 20V, Positive-QTOF	splash10-000i-0190000000-cba38a674f564ab650b7	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-maackiain-3-O-glucoside 40V, Positive-QTOF	splash10-00ri-4690000000-693118d786f2f353d617	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-maackiain-3-O-glucoside 10V, Negative-QTOF	splash10-000t-0150900000-ba9d8706eb127f6c7aa0	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-maackiain-3-O-glucoside 20V, Negative-QTOF	splash10-001i-1290200000-4d898ca193ddf83b14db	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-maackiain-3-O-glucoside 40V, Negative-QTOF	splash10-0ue9-2190000000-e124f13533de6b0ffd63	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-maackiain-3-O-glucoside 10V, Positive-QTOF	splash10-000i-0090100000-83968ec23630583f26a1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-maackiain-3-O-glucoside 20V, Positive-QTOF	splash10-000i-0090100000-1a0cb437a29152fcd075	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-maackiain-3-O-glucoside 40V, Positive-QTOF	splash10-000j-3194100000-251a5aff2b7f6797bda6	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-maackiain-3-O-glucoside 10V, Negative-QTOF	splash10-001i-0090100000-cb0ebb59bf4f59942431	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-maackiain-3-O-glucoside 20V, Negative-QTOF	splash10-001i-1090200000-4fc6d197894c929d8b28	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-maackiain-3-O-glucoside 40V, Negative-QTOF	splash10-001i-1190100000-8633e2f91d31fad2693f	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442827

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1856091

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for (-)-maackiain-3-O-glucoside (HMDB0303946)

MOL for HMDB0303946 ((-)-maackiain-3-O-glucoside)

3D MOL for HMDB0303946 ((-)-maackiain-3-O-glucoside)

3D SDF for HMDB0303946 ((-)-maackiain-3-O-glucoside)

3D-SDF for HMDB0303946 ((-)-maackiain-3-O-glucoside)

PDB for HMDB0303946 ((-)-maackiain-3-O-glucoside)

3D PDB for HMDB0303946 ((-)-maackiain-3-O-glucoside)

SMILES for HMDB0303946 ((-)-maackiain-3-O-glucoside)

INCHI for HMDB0303946 ((-)-maackiain-3-O-glucoside)

Structure for HMDB0303946 ((-)-maackiain-3-O-glucoside)

3D Structure for HMDB0303946 ((-)-maackiain-3-O-glucoside)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

MS/MS Spectra