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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 04:09:20 UTC

Update Date

2021-09-23 04:09:21 UTC

HMDB ID

HMDB0301980

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vitexin 6''-O-malonyl 2''-O-xyloside

Description

Vitexin, also known as apigenin 8-C-glucoside or 8-glycosylapigenin, belongs to the class of organic compounds known as flavonoid 8-C-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vitexin is also described as an apigenin flavone glucoside. Vitexin has been found in passion flower, chasteberry, bamboo leaves, millet and Hawthorn. Vitexin has shown a wide range of pharmacological effects, such as antioxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects (PMID: 27693342 ). Vitexin has also been shown to directly inhibit thyroid peroxidase and potentially contributes to goiter (PMID: 1696490 ). It is sometimes called a goitrogen.

Structure

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


  Mrv1652309272007302D          

 31 34  0  0  0  0            999 V2000
 9998.383410000.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8115 9998.3198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2356 9998.3198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.805110002.0388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.383410003.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.669210002.8675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.238710001.6306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.238710003.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.811510004.1044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.236010000.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.521510000.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5215 9999.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2360 9999.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9505 9999.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.950510000.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.810510000.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.095910000.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0959 9999.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8104 9999.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.091410001.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.377110002.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.662510001.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.662510000.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.377010000.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.091510000.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.811510003.2803    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.096910002.8678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.096910002.0426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.811510001.6301    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.526110002.0426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.526110002.8678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 20  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  2  0  0  0  0
 19 12  2  0  0  0  0
 15 23  1  0  0  0  0
 20  4  1  0  0  0  0
 13  3  2  0  0  0  0
 19  2  1  0  0  0  0
  1 17  1  0  0  0  0
 26 27  1  0  0  0  0
 26 31  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30  7  1  1  0  0  0
 31  8  1  6  0  0  0
 26  9  1  1  0  0  0
 27  5  1  6  0  0  0
 29 16  1  6  0  0  0
M  END

HMDB0301980
     RDKit          3D
Vitexin 6''-O-malonyl 2''-O-xyloside
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.9008   -3.9988    1.1464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207   -2.8906    0.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2309   -1.7850    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7219   -0.5352    0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6529    0.5877    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1613    1.8631   -0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0421    2.9246   -0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4025    2.7848   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3132    3.8450   -0.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922    1.5369    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171    0.4676    0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4348   -0.4485    0.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345   -1.4439    0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6990   -1.2549    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448    0.1318   -0.2663 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9163    0.4460    0.9582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164    1.5156    0.8309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2539    2.0095    2.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9631    1.0397    2.8579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9568    1.1418    0.0097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7693    2.2975   -0.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5750    0.5574   -1.2999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5562   -0.3436   -1.8008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2072    0.0397   -1.3910 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5446    0.6747   -2.5229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6050   -2.3072    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557   -2.1503   -0.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662   -3.5625    0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1983   -3.8136    0.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5955   -5.0628    1.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0657   -2.7333    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837   -1.9072    0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1122    1.9880   -0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533    3.9229   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7091    4.0729   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9615    1.3212    0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4578   -0.4938    0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4224    0.8275   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3018    2.3977    0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    2.8835    1.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4381    2.3801    2.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8885    1.0030    2.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5424    0.4277    0.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2131    3.0571   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6819    1.4216   -2.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0755   -1.0652   -2.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -1.0237   -1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9828    0.0369   -2.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5908   -2.9127    0.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194   -4.4132    0.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4257   -5.4575    1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 14 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31  2  1  0
 11  5  1  0
 31 13  1  0
 24 15  1  0
  3 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 15 38  1  6
 17 39  1  6
 18 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  1
 21 44  1  0
 22 45  1  6
 23 46  1  0
 24 47  1  6
 25 48  1  0
 27 49  1  0
 28 50  1  0
 30 51  1  0
M  END


  Mrv1652309272007302D          

 31 34  0  0  0  0            999 V2000
 9998.383410000.8039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8115 9998.3198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.2356 9998.3198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10004.805110002.0388    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.383410003.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.669210002.8675    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.238710001.6306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.238710003.2798    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.811510004.1044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.236010000.7999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.521510000.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.5215 9999.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.2360 9999.1499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.9505 9999.5624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.950510000.3875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.810510000.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.095910000.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.0959 9999.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.8104 9999.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.091410001.6289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.377110002.0414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.662510001.6288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.662510000.8038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.377010000.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.091510000.8039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.811510003.2803    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.096910002.8678    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9999.096910002.0426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.811510001.6301    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.526110002.0426    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.526110002.8678    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
  5  6  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 20  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 16  2  0  0  0  0
 19 12  2  0  0  0  0
 15 23  1  0  0  0  0
 20  4  1  0  0  0  0
 13  3  2  0  0  0  0
 19  2  1  0  0  0  0
  1 17  1  0  0  0  0
 26 27  1  0  0  0  0
 26 31  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 30  7  1  1  0  0  0
 31  8  1  6  0  0  0
 26  9  1  1  0  0  0
 27  5  1  6  0  0  0
 29 16  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0301980

> <DATABASE_NAME>
hmdb

> <SMILES>
OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1

> <INCHI_KEY>
SGEWCQFRYRRZDC-VPRICQMDSA-N

> <FORMULA>
C21H20O10

> <MOLECULAR_WEIGHT>
432.3775

> <EXACT_MASS>
432.10564686

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
41.51851326617695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

> <ALOGPS_LOGP>
0.36

> <JCHEM_LOGP>
-0.05063177133333335

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.001064878830134

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.172757071127353

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9791926292654134

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
106.03219999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.73e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vitexin

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0301980
     RDKit          3D
Vitexin 6''-O-malonyl 2''-O-xyloside
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.9008   -3.9988    1.1464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207   -2.8906    0.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2309   -1.7850    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7219   -0.5352    0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6529    0.5877    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1613    1.8631   -0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0421    2.9246   -0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4025    2.7848   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3132    3.8450   -0.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922    1.5369    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171    0.4676    0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4348   -0.4485    0.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345   -1.4439    0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6990   -1.2549    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448    0.1318   -0.2663 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9163    0.4460    0.9582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164    1.5156    0.8309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2539    2.0095    2.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9631    1.0397    2.8579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9568    1.1418    0.0097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7693    2.2975   -0.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5750    0.5574   -1.2999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5562   -0.3436   -1.8008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2072    0.0397   -1.3910 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5446    0.6747   -2.5229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6050   -2.3072    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557   -2.1503   -0.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662   -3.5625    0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1983   -3.8136    0.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5955   -5.0628    1.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0657   -2.7333    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837   -1.9072    0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1122    1.9880   -0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533    3.9229   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7091    4.0729   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9615    1.3212    0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4578   -0.4938    0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4224    0.8275   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3018    2.3977    0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    2.8835    1.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4381    2.3801    2.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8885    1.0030    2.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5424    0.4277    0.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2131    3.0571   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6819    1.4216   -2.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0755   -1.0652   -2.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -1.0237   -1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9828    0.0369   -2.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5908   -2.9127    0.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194   -4.4132    0.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4257   -5.4575    1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 14 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31  2  1  0
 11  5  1  0
 31 13  1  0
 24 15  1  0
  3 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 15 38  1  6
 17 39  1  6
 18 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  1
 21 44  1  0
 22 45  1  6
 23 46  1  0
 24 47  1  6
 25 48  1  0
 27 49  1  0
 28 50  1  0
 30 51  1  0
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8663.6498668.167   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8666.3158663.530   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8668.9738663.530   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8675.6368670.472   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0    8663.6498672.789   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0    8662.3168672.019   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8668.9798669.711   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8668.9798672.789   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8666.3158674.328   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8668.9748668.160   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0    8667.6408667.390   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8667.6408665.850   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8668.9748665.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8670.3088665.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8670.3088667.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.3138668.160   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8664.9798667.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8664.9798665.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8666.3138665.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8674.3048669.707   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8672.9718670.477   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8671.6378669.707   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8671.6378668.167   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8672.9708667.397   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8674.3048668.167   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8666.3158672.790   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8664.9818672.020   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0    8664.9818670.480   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0    8666.3158669.710   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8667.6498670.480   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8667.6498672.020   0.000  0.00  0.00           C+0
CONECT    1   17                                                            
CONECT    2   19                                                            
CONECT    3   13                                                            
CONECT    4   20                                                            
CONECT    5    6   27                                                       
CONECT    6    5                                                            
CONECT    7   30                                                            
CONECT    8   31                                                            
CONECT    9   26                                                            
CONECT   10   11   15                                                       
CONECT   11   12   10   16                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14    3                                                  
CONECT   14   13   15                                                       
CONECT   15   14   10   23                                                  
CONECT   16   17   11   29                                                  
CONECT   17   16   18    1                                                  
CONECT   18   17   19                                                       
CONECT   19   18   12    2                                                  
CONECT   20   21   25    4                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   15                                                  
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   27   31    9                                                  
CONECT   27   26   28    5                                                  
CONECT   28   27   29                                                       
CONECT   29   30   28   16                                                  
CONECT   30   29   31    7                                                  
CONECT   31   26   30    8                                                  
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

COMPND    HMDB0301980
HETATM    1  O1  UNL     1       2.901  -3.999   1.146  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.421  -2.891   0.826  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.231  -1.785   0.655  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.722  -0.535   0.293  1.00  0.00           C  
HETATM    5  C4  UNL     1       3.653   0.588   0.128  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.161   1.863  -0.181  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.042   2.925  -0.363  1.00  0.00           C  
HETATM    8  C7  UNL     1       5.402   2.785  -0.255  1.00  0.00           C  
HETATM    9  O2  UNL     1       6.313   3.845  -0.438  1.00  0.00           O  
HETATM   10  C8  UNL     1       5.892   1.537   0.046  1.00  0.00           C  
HETATM   11  C9  UNL     1       5.017   0.468   0.233  1.00  0.00           C  
HETATM   12  O3  UNL     1       1.435  -0.448   0.123  1.00  0.00           O  
HETATM   13  C10 UNL     1       0.634  -1.444   0.267  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.699  -1.255   0.042  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.245   0.132  -0.266  1.00  0.00           C  
HETATM   16  O4  UNL     1      -1.916   0.446   0.958  1.00  0.00           O  
HETATM   17  C13 UNL     1      -2.716   1.516   0.831  1.00  0.00           C  
HETATM   18  C14 UNL     1      -3.254   2.010   2.184  1.00  0.00           C  
HETATM   19  O5  UNL     1      -3.963   1.040   2.858  1.00  0.00           O  
HETATM   20  C15 UNL     1      -3.957   1.142   0.010  1.00  0.00           C  
HETATM   21  O6  UNL     1      -4.769   2.297  -0.143  1.00  0.00           O  
HETATM   22  C16 UNL     1      -3.575   0.557  -1.300  1.00  0.00           C  
HETATM   23  O7  UNL     1      -4.556  -0.344  -1.801  1.00  0.00           O  
HETATM   24  C17 UNL     1      -2.207   0.040  -1.391  1.00  0.00           C  
HETATM   25  O8  UNL     1      -1.545   0.675  -2.523  1.00  0.00           O  
HETATM   26  C18 UNL     1      -1.605  -2.307   0.171  1.00  0.00           C  
HETATM   27  O9  UNL     1      -2.956  -2.150  -0.034  1.00  0.00           O  
HETATM   28  C19 UNL     1      -1.166  -3.562   0.526  1.00  0.00           C  
HETATM   29  C20 UNL     1       0.198  -3.814   0.767  1.00  0.00           C  
HETATM   30  O10 UNL     1       0.595  -5.063   1.112  1.00  0.00           O  
HETATM   31  C21 UNL     1       1.066  -2.733   0.629  1.00  0.00           C  
HETATM   32  H1  UNL     1       4.284  -1.907   0.805  1.00  0.00           H  
HETATM   33  H2  UNL     1       2.112   1.988  -0.264  1.00  0.00           H  
HETATM   34  H3  UNL     1       3.653   3.923  -0.597  1.00  0.00           H  
HETATM   35  H4  UNL     1       6.709   4.073  -1.354  1.00  0.00           H  
HETATM   36  H5  UNL     1       6.962   1.321   0.152  1.00  0.00           H  
HETATM   37  H6  UNL     1       5.458  -0.494   0.464  1.00  0.00           H  
HETATM   38  H7  UNL     1      -0.422   0.828  -0.368  1.00  0.00           H  
HETATM   39  H8  UNL     1      -2.302   2.398   0.314  1.00  0.00           H  
HETATM   40  H9  UNL     1      -3.947   2.883   1.971  1.00  0.00           H  
HETATM   41  H10 UNL     1      -2.438   2.380   2.798  1.00  0.00           H  
HETATM   42  H11 UNL     1      -4.889   1.003   2.555  1.00  0.00           H  
HETATM   43  H12 UNL     1      -4.542   0.428   0.607  1.00  0.00           H  
HETATM   44  H13 UNL     1      -4.213   3.057  -0.459  1.00  0.00           H  
HETATM   45  H14 UNL     1      -3.682   1.422  -2.041  1.00  0.00           H  
HETATM   46  H15 UNL     1      -4.076  -1.065  -2.287  1.00  0.00           H  
HETATM   47  H16 UNL     1      -2.254  -1.024  -1.748  1.00  0.00           H  
HETATM   48  H17 UNL     1      -0.983   0.037  -2.986  1.00  0.00           H  
HETATM   49  H18 UNL     1      -3.591  -2.913   0.058  1.00  0.00           H  
HETATM   50  H19 UNL     1      -1.819  -4.413   0.641  1.00  0.00           H  
HETATM   51  H20 UNL     1       1.426  -5.458   1.314  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   31
CONECT    3    4    4   32
CONECT    4    5   12
CONECT    5    6    6   11
CONECT    6    7   33
CONECT    7    8    8   34
CONECT    8    9   10
CONECT    9   35
CONECT   10   11   11   36
CONECT   11   37
CONECT   12   13
CONECT   13   14   14   31
CONECT   14   15   26
CONECT   15   16   24   38
CONECT   16   17
CONECT   17   18   20   39
CONECT   18   19   40   41
CONECT   19   42
CONECT   20   21   22   43
CONECT   21   44
CONECT   22   23   24   45
CONECT   23   46
CONECT   24   25   47
CONECT   25   48
CONECT   26   27   28   28
CONECT   27   49
CONECT   28   29   50
CONECT   29   30   31   31
CONECT   30   51
END

HMDB0301980
     RDKit          3D
Vitexin 6''-O-malonyl 2''-O-xyloside
 51 54  0  0  0  0  0  0  0  0999 V2000
    2.9008   -3.9988    1.1464 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4207   -2.8906    0.8261 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2309   -1.7850    0.6553 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7219   -0.5352    0.2927 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6529    0.5877    0.1281 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1613    1.8631   -0.1806 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0421    2.9246   -0.3632 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4025    2.7848   -0.2555 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3132    3.8450   -0.4378 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8922    1.5369    0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0171    0.4676    0.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4348   -0.4485    0.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6345   -1.4439    0.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6990   -1.2549    0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2448    0.1318   -0.2663 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9163    0.4460    0.9582 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7164    1.5156    0.8309 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2539    2.0095    2.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9631    1.0397    2.8579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9568    1.1418    0.0097 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7693    2.2975   -0.1431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5750    0.5574   -1.2999 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.5562   -0.3436   -1.8008 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2072    0.0397   -1.3910 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5446    0.6747   -2.5229 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6050   -2.3072    0.1709 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9557   -2.1503   -0.0335 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1662   -3.5625    0.5256 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1983   -3.8136    0.7670 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5955   -5.0628    1.1122 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0657   -2.7333    0.6291 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2837   -1.9072    0.8053 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1122    1.9880   -0.2638 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6533    3.9229   -0.5969 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7091    4.0729   -1.3539 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9615    1.3212    0.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4578   -0.4938    0.4643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4224    0.8275   -0.3680 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3018    2.3977    0.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9473    2.8835    1.9708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4381    2.3801    2.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8885    1.0030    2.5546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5424    0.4277    0.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2131    3.0571   -0.4586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6819    1.4216   -2.0412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0755   -1.0652   -2.2867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2539   -1.0237   -1.7481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9828    0.0369   -2.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5908   -2.9127    0.0580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8194   -4.4132    0.6415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4257   -5.4575    1.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  4 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 17 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 14 26  1  0
 26 27  1  0
 26 28  2  0
 28 29  1  0
 29 30  1  0
 29 31  2  0
 31  2  1  0
 11  5  1  0
 31 13  1  0
 24 15  1  0
  3 32  1  0
  6 33  1  0
  7 34  1  0
  9 35  1  0
 10 36  1  0
 11 37  1  0
 15 38  1  6
 17 39  1  6
 18 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  1
 21 44  1  0
 22 45  1  6
 23 46  1  0
 24 47  1  6
 25 48  1  0
 27 49  1  0
 28 50  1  0
 30 51  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Apigenin 8-C-glucoside	ChEBI
8-Glycosyl-apigenin	MeSH
8-Glycosylapigenin	MeSH
8-beta-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	PhytoBank
8-β-D-Glucopyranosyl-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one	PhytoBank
5,7,4'-Trihydroxyflavone 8-C-beta-D-glucopyranoside	PhytoBank
5,7,4'-Trihydroxyflavone 8-C-β-D-glucopyranoside	PhytoBank
5,7,4’-Trihydroxyflavone 8-C-β-D-glucopyranoside	PhytoBank
8-C-Glucosylapigenin	PhytoBank
8-C-beta-D-Glucopyranosylapigenin	PhytoBank
8-C-β-D-Glucopyranosylapigenin	PhytoBank
Apigenin 8-C-beta-D-glucoside	PhytoBank
Apigenin 8-C-β-D-glucoside	PhytoBank
Apigenin 8-C-beta-glucopyranoside	PhytoBank
Apigenin 8-C-β-glucopyranoside	PhytoBank
Apigenin-8-C-beta-D-glucopyranoside	PhytoBank
Apigenin-8-C-β-D-glucopyranoside	PhytoBank
Orientoside	PhytoBank
Vitexina	PhytoBank
Vitexine	PhytoBank

Chemical Formula

C₂₁H₂₀O₁₀

Average Molecular Weight

432.3775

Monoisotopic Molecular Weight

432.10564686

IUPAC Name

5,7-dihydroxy-2-(4-hydroxyphenyl)-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

Traditional Name

vitexin

CAS Registry Number

Not Available

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=C2OC(=CC(=O)C2=C(O)C=C1O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C21H20O10/c22-7-14-17(27)18(28)19(29)21(31-14)16-11(25)5-10(24)15-12(26)6-13(30-20(15)16)8-1-3-9(23)4-2-8/h1-6,14,17-19,21-25,27-29H,7H2/t14-,17-,18+,19-,21+/m1/s1

InChI Key

SGEWCQFRYRRZDC-VPRICQMDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid 8-c-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid 8-C-glycosides

Alternative Parents

Substituents

Flavonoid-8-c-glycoside
Hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavone
Phenolic glycoside
Hexose monosaccharide
Glycosyl compound
C-glycosyl compound
Chromone
1-benzopyran
Benzopyran
Pyranone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Pyran
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Oxane
Heteroaromatic compound
Vinylogous acid
Secondary alcohol
Ether
Dialkyl ether
Organoheterocyclic compound
Oxacycle
Polyol
Primary alcohol
Organic oxide
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

C-glycosyl compound (CHEBI:16954 )
trihydroxyflavone (CHEBI:16954 )
flavones (C01460 )
Flavones and Flavonols (C01460 )

Ontology

Not Available

Exogenous (HMDB: HMDB0301980)

Food

Vegetable

Leaf vegetable

Common beet (FooDB: FOOD00025)

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	0.36	ALOGPS
logP	-0.051	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	6.17	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	106.03 m³·mol⁻¹	ChemAxon
Polarizability	41.52 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	203.867	32859911
AllCCS	[M+H-H2O]+	201.169	32859911
AllCCS	[M+Na]+	207.067	32859911
AllCCS	[M+NH4]+	206.355	32859911
AllCCS	[M-H]-	202.277	32859911
AllCCS	[M+Na-2H]-	202.812	32859911
AllCCS	[M+HCOO]-	203.561	32859911
DeepCCS	[M+H]+	197.064	30932474
DeepCCS	[M-H]-	195.168	30932474
DeepCCS	[M-2H]-	228.41	30932474
DeepCCS	[M+Na]+	202.929	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	10.7209 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	5.15 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1775.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	195.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	101.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	158.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	102.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	341.5 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	358.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	563.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	630.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	285.0 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	1275.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	236.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	407.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	344.6 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	236.1 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vitexin 6''-O-malonyl 2''-O-xyloside,3TMS,isomer #19	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3993.3	Semi standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,3TMS,isomer #19	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3989.0	Standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,3TMS,isomer #19	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4924.3	Standard polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TMS,isomer #23	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3855.7	Semi standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TMS,isomer #23	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3955.3	Standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TMS,isomer #23	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4622.6	Standard polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TMS,isomer #25	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)=C3O2)C=C1	3879.9	Semi standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TMS,isomer #25	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)=C3O2)C=C1	3953.5	Standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TMS,isomer #25	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)=C3O2)C=C1	4647.7	Standard polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TMS,isomer #26	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3906.9	Semi standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TMS,isomer #26	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3959.1	Standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TMS,isomer #26	C[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4573.2	Standard polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,5TMS,isomer #17	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)=C3O2)C=C1	3888.3	Semi standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,5TMS,isomer #17	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)=C3O2)C=C1	3913.4	Standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,5TMS,isomer #17	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)=C3O2)C=C1	4413.9	Standard polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,5TMS,isomer #18	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3830.9	Semi standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,5TMS,isomer #18	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	3924.9	Standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,5TMS,isomer #18	C[Si](C)(C)OC1=CC(O[Si](C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	4326.8	Standard polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,5TMS,isomer #19	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C([C@@H]4O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)=C3O2)C=C1	3870.3	Semi standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,5TMS,isomer #19	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C([C@@H]4O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)=C3O2)C=C1	3912.1	Standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,5TMS,isomer #19	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O)C=C(O[Si](C)(C)C)C([C@@H]4O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)=C3O2)C=C1	4359.1	Standard polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,6TMS,isomer #7	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C([C@@H]4O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)=C3O2)C=C1	3891.4	Semi standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,6TMS,isomer #7	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C([C@@H]4O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)=C3O2)C=C1	3885.7	Standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,6TMS,isomer #7	C[Si](C)(C)OC1=CC=C(C2=CC(=O)C3=C(O[Si](C)(C)C)C=C(O[Si](C)(C)C)C([C@@H]4O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]4O[Si](C)(C)C)=C3O2)C=C1	4169.5	Standard polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,3TBDMS,isomer #19	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4655.3	Semi standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,3TBDMS,isomer #19	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4663.2	Standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,3TBDMS,isomer #19	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4998.7	Standard polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TBDMS,isomer #23	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4784.8	Semi standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TBDMS,isomer #23	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4779.4	Standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TBDMS,isomer #23	CC(C)(C)[Si](C)(C)OC1=CC(O[Si](C)(C)C(C)(C)C)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4814.8	Standard polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TBDMS,isomer #26	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4722.1	Semi standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TBDMS,isomer #26	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4803.4	Standard non polar	33892256
Vitexin 6''-O-malonyl 2''-O-xyloside,4TBDMS,isomer #26	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)C=C(C3=CC=C(O)C=C3)OC2=C1[C@@H]1O[C@H](CO)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	4768.7	Standard polar	33892256

Spectra

Biological Properties

Cellular Locations

Not Available

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Vitexin

METLIN ID

Not Available

PubChem Compound

5280441

PDB ID

Not Available

ChEBI ID

16954

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1667761

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

He M, Min JW, Kong WL, He XH, Li JX, Peng BW: A review on the pharmacological effects of vitexin and isovitexin. Fitoterapia. 2016 Dec;115:74-85. doi: 10.1016/j.fitote.2016.09.011. Epub 2016 Sep 28. [PubMed:27693342 ]
Gaitan E: Goitrogens in food and water. Annu Rev Nutr. 1990;10:21-39. doi: 10.1146/annurev.nu.10.070190.000321. [PubMed:1696490 ]

Showing metabocard for Vitexin 6''-O-malonyl 2''-O-xyloside (HMDB0301980)

MOL for HMDB0301980 (Vitexin 6''-O-malonyl 2''-O-xyloside)

3D MOL for HMDB0301980 (Vitexin 6''-O-malonyl 2''-O-xyloside)

3D SDF for HMDB0301980 (Vitexin 6''-O-malonyl 2''-O-xyloside)

3D-SDF for HMDB0301980 (Vitexin 6''-O-malonyl 2''-O-xyloside)

PDB for HMDB0301980 (Vitexin 6''-O-malonyl 2''-O-xyloside)

3D PDB for HMDB0301980 (Vitexin 6''-O-malonyl 2''-O-xyloside)

SMILES for HMDB0301980 (Vitexin 6''-O-malonyl 2''-O-xyloside)

INCHI for HMDB0301980 (Vitexin 6''-O-malonyl 2''-O-xyloside)

Structure for HMDB0301980 (Vitexin 6''-O-malonyl 2''-O-xyloside)

3D Structure for HMDB0301980 (Vitexin 6''-O-malonyl 2''-O-xyloside)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized