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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2009-07-25 00:01:09 UTC

Update Date

2021-09-14 15:47:37 UTC

HMDB ID

HMDB0012468

Secondary Accession Numbers

HMDB12468

Metabolite Identification

Common Name

(-)-Epigallocatechin sulfate

Description

Epigallocatechin sulfate is the sulfated form of epigallocatechin, wherein the sulfate group is attached to the O-3 position. Sulfation is a phase II biotransformation reaction that involves a sulfotransferase enzyme catalyzing the transfer of a sulfo group from a donor cosubstrate, usually 3'-phosphoadenosine-5'-phosphosulfate (PAPS), to a substrate molecule's hydroxyl group (in this case epigallogatechin). Sulfation is involved in a variety of biological processes, including detoxification, hormone regulation, molecular recognition, cell signaling, and viral entry into cells. Epigallocatechin (EGC) is a flavan-3-ol, which are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton. EGC is one of the antioxidant chemicals found in many fruits and teas. This compound possesses an epimer, found notably in green tea, called "gallocatechin" (GC) (PMID: 30917581 ), with the gallate residue being in an isomeric trans position. Other sources of gallocatechin are bananas, persimmon, and pomegranate. This compound had been shown to have moderate affinity to the human cannabinoid receptor, which may contribute to the health benefits found by consuming green tea.

Structure

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


  Mrv0541 02251208042D          

 26 28  0  0  1  0            999 V2000
   10.5539  -12.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3789  -12.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7914  -11.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6164  -11.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0289  -11.1719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0289  -12.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8539  -12.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2664  -13.3154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8539  -14.0298    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0289  -14.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6164  -13.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7914  -13.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2664  -14.7443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8539  -15.4588    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1395  -15.0463    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   14.5684  -15.8713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4414  -16.1732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0914  -13.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5039  -12.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3289  -12.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7414  -11.8864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7414  -13.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5664  -13.3153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3289  -14.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7414  -14.7443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5039  -14.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 18  1  1  0  0  0
  9 10  1  0  0  0  0
  9 13  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 14 17  2  0  0  0  0
 18 19  1  0  0  0  0
 18 26  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  CHG  1  15  -1
M  END

HMDB0012468
     RDKit          3D
(-)-Epigallocatechin sulfate
 39 41  0  0  0  0  0  0  0  0999 V2000
    1.8133    3.4374   -1.8774 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529    3.8924   -1.0564 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.3698    4.4723   -1.9902 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885    5.1056    0.0321 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.0639    2.6435   -0.2051 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5767    1.4496   -0.3251 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1671    0.8724    0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0748   -0.2368    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2901   -0.4386    1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1302   -1.4571    0.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3650   -1.6655    1.4117 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168   -2.2725   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5123   -2.0876   -0.9000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1026   -2.9120   -1.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6788   -1.0550   -0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4606   -0.8242   -1.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2544    0.4053   -1.0148 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5289    0.0800   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922    0.7587    0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3179    0.3784    1.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8145    1.1213    2.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9719   -0.7130    0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1870   -1.1359    1.2385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284   -1.4209   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1089   -2.5167   -0.8433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2144   -1.0099   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4653    1.6414   -1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265    1.6325    1.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274    0.4300    1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5634    0.2260    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1511   -1.1718    1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3466   -3.0912   -0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2266   -2.7761   -2.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4715    0.7256   -2.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075    1.5968    1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6689    0.9508    2.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6144   -0.6513    2.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9907   -2.7787   -0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8316   -1.6053   -1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 17  6  1  0
 26 18  1  0
 15  8  1  0
  6 27  1  6
  7 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 17 34  1  6
 19 35  1  0
 21 36  1  0
 23 37  1  0
 25 38  1  0
 26 39  1  0
M  CHG  1   4  -1
M  END


  Mrv0541 02251208042D          

 26 28  0  0  1  0            999 V2000
   10.5539  -12.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3789  -12.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7914  -11.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6164  -11.8864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0289  -11.1719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0289  -12.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8539  -12.6009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2664  -13.3154    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.8539  -14.0298    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.0289  -14.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6164  -13.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7914  -13.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2664  -14.7443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8539  -15.4588    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1395  -15.0463    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   14.5684  -15.8713    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4414  -16.1732    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0914  -13.3154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5039  -12.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3289  -12.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7414  -11.8864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7414  -13.3153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5664  -13.3153    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3289  -14.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7414  -14.7443    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5039  -14.0298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 18  1  1  0  0  0
  9 10  1  0  0  0  0
  9 13  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 14 17  2  0  0  0  0
 18 19  1  0  0  0  0
 18 26  2  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
M  CHG  1  15  -1
M  END
> <DATABASE_ID>
HMDB0012468

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=CC2=C(O[C@H]([C@H](C2)OS([O-])(=O)=O)C2=CC(O)=C(O)C(O)=C2)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H14O10S/c16-8-1-6-4-12(25-26(21,22)23)15(24-14(6)11(19)5-8)7-2-9(17)13(20)10(18)3-7/h1-3,5,12,15-20H,4H2,(H,21,22,23)/p-1/t12-,15-/m0/s1

> <INCHI_KEY>
PFNBTZIECYHRTC-WFASDCNBSA-M

> <FORMULA>
C15H13O10S

> <MOLECULAR_WEIGHT>
385.323

> <EXACT_MASS>
385.022942326

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
34.238617265957814

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,3S)-6,8-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl sulfate

> <ALOGPS_LOGP>
1.20

> <JCHEM_LOGP>
1.5465274616666662

> <ALOGPS_LOGS>
-2.06

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.750765262230688

> <JCHEM_PKA_STRONGEST_ACIDIC>
-2.263805328236778

> <JCHEM_PKA_STRONGEST_BASIC>
-4.824241524909177

> <JCHEM_POLAR_SURFACE_AREA>
176.80999999999997

> <JCHEM_REFRACTIVITY>
84.85069999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3S)-6,8-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl sulfate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012468
     RDKit          3D
(-)-Epigallocatechin sulfate
 39 41  0  0  0  0  0  0  0  0999 V2000
    1.8133    3.4374   -1.8774 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529    3.8924   -1.0564 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.3698    4.4723   -1.9902 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885    5.1056    0.0321 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.0639    2.6435   -0.2051 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5767    1.4496   -0.3251 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1671    0.8724    0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0748   -0.2368    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2901   -0.4386    1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1302   -1.4571    0.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3650   -1.6655    1.4117 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168   -2.2725   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5123   -2.0876   -0.9000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1026   -2.9120   -1.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6788   -1.0550   -0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4606   -0.8242   -1.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2544    0.4053   -1.0148 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5289    0.0800   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922    0.7587    0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3179    0.3784    1.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8145    1.1213    2.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9719   -0.7130    0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1870   -1.1359    1.2385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284   -1.4209   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1089   -2.5167   -0.8433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2144   -1.0099   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4653    1.6414   -1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265    1.6325    1.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274    0.4300    1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5634    0.2260    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1511   -1.1718    1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3466   -3.0912   -0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2266   -2.7761   -2.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4715    0.7256   -2.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075    1.5968    1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6689    0.9508    2.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6144   -0.6513    2.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9907   -2.7787   -0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8316   -1.6053   -1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 17  6  1  0
 26 18  1  0
 15  8  1  0
  6 27  1  6
  7 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 17 34  1  6
 19 35  1  0
 21 36  1  0
 23 37  1  0
 25 38  1  0
 26 39  1  0
M  CHG  1   4  -1
M  END

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  O   UNK     0      19.701 -23.522   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      21.241 -23.522   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.011 -22.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      23.551 -22.188   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      24.321 -20.854   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      24.321 -23.522   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      25.861 -23.522   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      26.631 -24.855   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.861 -26.189   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.321 -26.189   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.551 -24.855   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.011 -24.855   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      26.631 -27.523   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0      25.861 -28.856   0.000  0.00  0.00           S+0
HETATM   15  O   UNK     0      24.527 -28.086   0.000  0.00  0.00           O-1
HETATM   16  O   UNK     0      27.194 -29.626   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      25.091 -30.190   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      28.171 -24.855   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.941 -23.522   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      30.481 -23.522   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      31.251 -22.188   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      31.251 -24.855   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      32.791 -24.855   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      30.481 -26.189   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      31.251 -27.523   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      28.941 -26.189   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   18                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12    2   11                                                       
CONECT   13    9   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18    8   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   18   24                                                       
MASTER        0    0    0    0    0    0    0    0   26    0   56    0
END

COMPND    HMDB0012468
HETATM    1  O1  UNL     1       1.813   3.437  -1.877  1.00  0.00           O  
HETATM    2  S1  UNL     1       0.653   3.892  -1.056  1.00  0.00           S  
HETATM    3  O2  UNL     1      -0.370   4.472  -1.990  1.00  0.00           O  
HETATM    4  O3  UNL     1       1.089   5.106   0.032  1.00  0.00           O1-
HETATM    5  O4  UNL     1      -0.064   2.643  -0.205  1.00  0.00           O  
HETATM    6  C1  UNL     1       0.577   1.450  -0.325  1.00  0.00           C  
HETATM    7  C2  UNL     1       1.167   0.872   0.926  1.00  0.00           C  
HETATM    8  C3  UNL     1       2.075  -0.237   0.514  1.00  0.00           C  
HETATM    9  C4  UNL     1       3.290  -0.439   1.146  1.00  0.00           C  
HETATM   10  C5  UNL     1       4.130  -1.457   0.772  1.00  0.00           C  
HETATM   11  O5  UNL     1       5.365  -1.666   1.412  1.00  0.00           O  
HETATM   12  C6  UNL     1       3.717  -2.273  -0.259  1.00  0.00           C  
HETATM   13  C7  UNL     1       2.512  -2.088  -0.900  1.00  0.00           C  
HETATM   14  O6  UNL     1       2.103  -2.912  -1.937  1.00  0.00           O  
HETATM   15  C8  UNL     1       1.679  -1.055  -0.508  1.00  0.00           C  
HETATM   16  O7  UNL     1       0.461  -0.824  -1.116  1.00  0.00           O  
HETATM   17  C9  UNL     1      -0.254   0.405  -1.015  1.00  0.00           C  
HETATM   18  C10 UNL     1      -1.529   0.080  -0.360  1.00  0.00           C  
HETATM   19  C11 UNL     1      -2.092   0.759   0.688  1.00  0.00           C  
HETATM   20  C12 UNL     1      -3.318   0.378   1.249  1.00  0.00           C  
HETATM   21  O8  UNL     1      -3.814   1.121   2.307  1.00  0.00           O  
HETATM   22  C13 UNL     1      -3.972  -0.713   0.725  1.00  0.00           C  
HETATM   23  O9  UNL     1      -5.187  -1.136   1.239  1.00  0.00           O  
HETATM   24  C14 UNL     1      -3.428  -1.421  -0.335  1.00  0.00           C  
HETATM   25  O10 UNL     1      -4.109  -2.517  -0.843  1.00  0.00           O  
HETATM   26  C15 UNL     1      -2.214  -1.010  -0.859  1.00  0.00           C  
HETATM   27  H1  UNL     1       1.465   1.641  -1.004  1.00  0.00           H  
HETATM   28  H2  UNL     1       1.726   1.633   1.504  1.00  0.00           H  
HETATM   29  H3  UNL     1       0.427   0.430   1.614  1.00  0.00           H  
HETATM   30  H4  UNL     1       3.563   0.226   1.944  1.00  0.00           H  
HETATM   31  H5  UNL     1       6.151  -1.172   1.004  1.00  0.00           H  
HETATM   32  H6  UNL     1       4.347  -3.091  -0.591  1.00  0.00           H  
HETATM   33  H7  UNL     1       1.227  -2.776  -2.402  1.00  0.00           H  
HETATM   34  H8  UNL     1      -0.472   0.726  -2.054  1.00  0.00           H  
HETATM   35  H9  UNL     1      -1.608   1.597   1.109  1.00  0.00           H  
HETATM   36  H10 UNL     1      -4.669   0.951   2.785  1.00  0.00           H  
HETATM   37  H11 UNL     1      -5.614  -0.651   2.006  1.00  0.00           H  
HETATM   38  H12 UNL     1      -4.991  -2.779  -0.429  1.00  0.00           H  
HETATM   39  H13 UNL     1      -1.832  -1.605  -1.696  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    3    4    5
CONECT    5    6
CONECT    6    7   17   27
CONECT    7    8   28   29
CONECT    8    9    9   15
CONECT    9   10   30
CONECT   10   11   12   12
CONECT   11   31
CONECT   12   13   32
CONECT   13   14   15   15
CONECT   14   33
CONECT   15   16
CONECT   16   17
CONECT   17   18   34
CONECT   18   19   19   26
CONECT   19   20   35
CONECT   20   21   22   22
CONECT   21   36
CONECT   22   23   24
CONECT   23   37
CONECT   24   25   26   26
CONECT   25   38
CONECT   26   39
END

HMDB0012468
     RDKit          3D
(-)-Epigallocatechin sulfate
 39 41  0  0  0  0  0  0  0  0999 V2000
    1.8133    3.4374   -1.8774 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6529    3.8924   -1.0564 S   0  0  0  0  0  6  0  0  0  0  0  0
   -0.3698    4.4723   -1.9902 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885    5.1056    0.0321 O   0  0  0  0  0  1  0  0  0  0  0  0
   -0.0639    2.6435   -0.2051 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5767    1.4496   -0.3251 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1671    0.8724    0.9259 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0748   -0.2368    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2901   -0.4386    1.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1302   -1.4571    0.7722 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3650   -1.6655    1.4117 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7168   -2.2725   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5123   -2.0876   -0.9000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1026   -2.9120   -1.9372 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6788   -1.0550   -0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4606   -0.8242   -1.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2544    0.4053   -1.0148 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5289    0.0800   -0.3602 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0922    0.7587    0.6881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3179    0.3784    1.2489 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8145    1.1213    2.3069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9719   -0.7130    0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1870   -1.1359    1.2385 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4284   -1.4209   -0.3353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1089   -2.5167   -0.8433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2144   -1.0099   -0.8591 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4653    1.6414   -1.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7265    1.6325    1.5037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4274    0.4300    1.6137 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5634    0.2260    1.9441 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1511   -1.1718    1.0040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3466   -3.0912   -0.5906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2266   -2.7761   -2.4019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4715    0.7256   -2.0540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6075    1.5968    1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6689    0.9508    2.7854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6144   -0.6513    2.0057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9907   -2.7787   -0.4291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8316   -1.6053   -1.6957 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  2  0
  2  4  1  0
  2  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  2  0
 17  6  1  0
 26 18  1  0
 15  8  1  0
  6 27  1  6
  7 28  1  0
  7 29  1  0
  9 30  1  0
 11 31  1  0
 12 32  1  0
 14 33  1  0
 17 34  1  6
 19 35  1  0
 21 36  1  0
 23 37  1  0
 25 38  1  0
 26 39  1  0
M  CHG  1   4  -1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2S,3S)-8-Hydroxy-3-(sulfooxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-6-olic acid	Generator
(2S,3S)-8-Hydroxy-3-(sulphooxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-6-olate	Generator
(2S,3S)-8-Hydroxy-3-(sulphooxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-6-olic acid	Generator
EACSul	HMDB
(-)-Epigallocatechin sulfuric acid	Generator
(-)-Epigallocatechin sulphate	Generator
(-)-Epigallocatechin sulphuric acid	Generator

Chemical Formula

C₁₅H₁₃O₁₀S

Average Molecular Weight

385.323

Monoisotopic Molecular Weight

385.022942326

IUPAC Name

(2S,3S)-6,8-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl sulfate

Traditional Name

(2S,3S)-6,8-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl sulfate

CAS Registry Number

Not Available

SMILES

OC1=CC2=C(O[C@H]([C@H](C2)OS([O-])(=O)=O)C2=CC(O)=C(O)C(O)=C2)C(O)=C1

InChI Identifier

InChI=1S/C15H14O10S/c16-8-1-6-4-12(25-26(21,22)23)15(24-14(6)11(19)5-8)7-2-9(17)13(20)10(18)3-7/h1-3,5,12,15-20H,4H2,(H,21,22,23)/p-1/t12-,15-/m0/s1

InChI Key

PFNBTZIECYHRTC-WFASDCNBSA-M

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-sulfated flavonoids. These are flavonoids that are sulfated at the 3-ring position of the flavonoid skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Sulfated flavonoids

Direct Parent

3-sulfated flavonoids

Alternative Parents

Substituents

3-sulfated flavonoid
Hydroxyflavonoid
3'-hydroxyflavonoid
4'-hydroxyflavonoid
6-hydroxyflavonoid
8-hydroxyflavonoid
Flavan-3-ol
Flavan
1-benzopyran
Benzopyran
Chromane
Pyrogallol derivative
Benzenetriol
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Sulfuric acid ester
Alkyl sulfate
Sulfate-ester
Sulfuric acid monoester
Organic sulfuric acid or derivatives
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Source

Endogenous

Endogenous (HMDB: HMDB0012468)

Exogenous

Food

Cocoa and cocoa product

Cocoa and cocoa products (HMDB: HMDB0012468)

Tea

Tea products (HMDB: HMDB0012468)

Nut

Nuts (HMDB: HMDB0012468)

Beverage

Alcoholic beverage

Red wine (HMDB: HMDB0012468)

Fruit

Berries (HMDB: HMDB0012468)

Pome

Apple (HMDB: HMDB0012468)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

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
Water Solubility	3.54 g/L	ALOGPS
logP	1.2	ALOGPS
logP	1.55	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-2.3	ChemAxon
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	176.81 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	84.85 m³·mol⁻¹	ChemAxon
Polarizability	34.24 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M+H]+	182.473	30932474
DeepCCS	[M-H]-	180.077	30932474
DeepCCS	[M-2H]-	212.959	30932474
DeepCCS	[M+Na]+	188.824	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.01 minutes	32390414
Predicted by Siyang on May 30, 2022	11.2471 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.34 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	67.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1127.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	206.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	85.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	135.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	65.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	508.1 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	350.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	654.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	690.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	257.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1207.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	196.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	248.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	586.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	424.2 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	399.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-Epigallocatechin sulfate	OC1=CC2=C(O[C@H]([C@H](C2)OS([O-])(=O)=O)C2=CC(O)=C(O)C(O)=C2)C(O)=C1	6331.1	Standard polar	33892256
(-)-Epigallocatechin sulfate	OC1=CC2=C(O[C@H]([C@H](C2)OS([O-])(=O)=O)C2=CC(O)=C(O)C(O)=C2)C(O)=C1	3288.1	Standard non polar	33892256
(-)-Epigallocatechin sulfate	OC1=CC2=C(O[C@H]([C@H](C2)OS([O-])(=O)=O)C2=CC(O)=C(O)C(O)=C2)C(O)=C1	3648.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(-)-Epigallocatechin sulfate,1TMS,isomer #1	C[Si](C)(C)OC1=CC(O)=C2O[C@@H](C3=CC(O)=C(O)C(O)=C3)[C@@H](OS(=O)(=O)[O-])CC2=C1	3416.5	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,1TMS,isomer #2	C[Si](C)(C)OC1=CC([C@@H]2OC3=C(O)C=C(O)C=C3C[C@@H]2OS(=O)(=O)[O-])=CC(O)=C1O	3401.9	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,1TMS,isomer #3	C[Si](C)(C)OC1=C(O)C=C([C@@H]2OC3=C(O)C=C(O)C=C3C[C@@H]2OS(=O)(=O)[O-])C=C1O	3346.5	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,1TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=CC2=C1O[C@@H](C1=CC(O)=C(O)C(O)=C1)[C@@H](OS(=O)(=O)[O-])C2	3439.9	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(O[C@@H](C3=CC(O)=C(O)C(O)=C3)[C@@H](OS(=O)(=O)[O-])C2)C(O[Si](C)(C)C)=C1	3349.0	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TMS,isomer #2	C[Si](C)(C)OC1=CC(O)=C2O[C@@H](C3=CC(O)=C(O)C(O[Si](C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])CC2=C1	3286.7	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2O[C@@H](C3=CC(O)=C(O[Si](C)(C)C)C(O)=C3)[C@@H](OS(=O)(=O)[O-])CC2=C1	3350.7	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TMS,isomer #4	C[Si](C)(C)OC1=CC([C@@H]2OC3=C(C=C(O)C=C3O[Si](C)(C)C)C[C@@H]2OS(=O)(=O)[O-])=CC(O)=C1O	3361.3	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TMS,isomer #5	C[Si](C)(C)OC1=CC([C@@H]2OC3=C(O)C=C(O)C=C3C[C@@H]2OS(=O)(=O)[O-])=CC(O[Si](C)(C)C)=C1O	3326.2	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TMS,isomer #6	C[Si](C)(C)OC1=CC([C@@H]2OC3=C(O)C=C(O)C=C3C[C@@H]2OS(=O)(=O)[O-])=CC(O)=C1O[Si](C)(C)C	3293.3	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TMS,isomer #7	C[Si](C)(C)OC1=CC(O)=CC2=C1O[C@@H](C1=CC(O)=C(O[Si](C)(C)C)C(O)=C1)[C@@H](OS(=O)(=O)[O-])C2	3291.0	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(O[C@@H](C3=CC(O)=C(O)C(O[Si](C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])C2)C(O[Si](C)(C)C)=C1	3197.9	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(O[C@@H](C3=CC(O)=C(O[Si](C)(C)C)C(O)=C3)[C@@H](OS(=O)(=O)[O-])C2)C(O[Si](C)(C)C)=C1	3294.2	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2O[C@@H](C3=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])CC2=C1	3306.8	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=C2O[C@@H](C3=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])CC2=C1	3304.6	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TMS,isomer #5	C[Si](C)(C)OC1=CC([C@@H]2OC3=C(C=C(O)C=C3O[Si](C)(C)C)C[C@@H]2OS(=O)(=O)[O-])=CC(O[Si](C)(C)C)=C1O	3244.5	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TMS,isomer #6	C[Si](C)(C)OC1=CC([C@@H]2OC3=C(C=C(O)C=C3O[Si](C)(C)C)C[C@@H]2OS(=O)(=O)[O-])=CC(O)=C1O[Si](C)(C)C	3229.0	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TMS,isomer #7	C[Si](C)(C)OC1=CC([C@@H]2OC3=C(O)C=C(O)C=C3C[C@@H]2OS(=O)(=O)[O-])=CC(O[Si](C)(C)C)=C1O[Si](C)(C)C	3241.9	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,4TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(O[C@@H](C3=CC(O[Si](C)(C)C)=C(O)C(O[Si](C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])C2)C(O[Si](C)(C)C)=C1	3264.3	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,4TMS,isomer #2	C[Si](C)(C)OC1=CC2=C(O[C@@H](C3=CC(O)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])C2)C(O[Si](C)(C)C)=C1	3247.4	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,4TMS,isomer #3	C[Si](C)(C)OC1=CC(O)=C2O[C@@H](C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])CC2=C1	3277.1	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,4TMS,isomer #4	C[Si](C)(C)OC1=CC(O)=CC2=C1O[C@@H](C1=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[C@@H](OS(=O)(=O)[O-])C2	3198.2	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,5TMS,isomer #1	C[Si](C)(C)OC1=CC2=C(O[C@@H](C3=CC(O[Si](C)(C)C)=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])C2)C(O[Si](C)(C)C)=C1	3241.8	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2O[C@@H](C3=CC(O)=C(O)C(O)=C3)[C@@H](OS(=O)(=O)[O-])CC2=C1	3742.2	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC([C@@H]2OC3=C(O)C=C(O)C=C3C[C@@H]2OS(=O)(=O)[O-])=CC(O)=C1O	3766.1	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=C(O)C=C([C@@H]2OC3=C(O)C=C(O)C=C3C[C@@H]2OS(=O)(=O)[O-])C=C1O	3705.7	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1O[C@@H](C1=CC(O)=C(O)C(O)=C1)[C@@H](OS(=O)(=O)[O-])C2	3788.6	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(O[C@@H](C3=CC(O)=C(O)C(O)=C3)[C@@H](OS(=O)(=O)[O-])C2)C(O[Si](C)(C)C(C)(C)C)=C1	3860.8	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2O[C@@H](C3=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])CC2=C1	3848.5	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2O[C@@H](C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)[C@@H](OS(=O)(=O)[O-])CC2=C1	3915.0	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC([C@@H]2OC3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)C[C@@H]2OS(=O)(=O)[O-])=CC(O)=C1O	3878.7	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC([C@@H]2OC3=C(O)C=C(O)C=C3C[C@@H]2OS(=O)(=O)[O-])=CC(O[Si](C)(C)C(C)(C)C)=C1O	3876.8	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC([C@@H]2OC3=C(O)C=C(O)C=C3C[C@@H]2OS(=O)(=O)[O-])=CC(O)=C1O[Si](C)(C)C(C)(C)C	3856.2	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1O[C@@H](C1=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[C@@H](OS(=O)(=O)[O-])C2	3853.7	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(O[C@@H](C3=CC(O)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])C2)C(O[Si](C)(C)C(C)(C)C)=C1	3996.7	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(O[C@@H](C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)[C@@H](OS(=O)(=O)[O-])C2)C(O[Si](C)(C)C(C)(C)C)=C1	4052.6	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2O[C@@H](C3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])CC2=C1	4084.9	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2O[C@@H](C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])CC2=C1	4050.9	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC1=CC([C@@H]2OC3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)C[C@@H]2OS(=O)(=O)[O-])=CC(O[Si](C)(C)C(C)(C)C)=C1O	4016.8	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC([C@@H]2OC3=C(C=C(O)C=C3O[Si](C)(C)C(C)(C)C)C[C@@H]2OS(=O)(=O)[O-])=CC(O)=C1O[Si](C)(C)C(C)(C)C	3988.9	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC([C@@H]2OC3=C(O)C=C(O)C=C3C[C@@H]2OS(=O)(=O)[O-])=CC(O[Si](C)(C)C(C)(C)C)=C1O[Si](C)(C)C(C)(C)C	4020.1	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC2=C(O[C@@H](C3=CC(O[Si](C)(C)C(C)(C)C)=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])C2)C(O[Si](C)(C)C(C)(C)C)=C1	4224.4	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC2=C(O[C@@H](C3=CC(O)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])C2)C(O[Si](C)(C)C(C)(C)C)=C1	4192.0	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC(O)=C2O[C@@H](C3=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)[C@@H](OS(=O)(=O)[O-])CC2=C1	4214.9	Semi standard non polar	33892256
(-)-Epigallocatechin sulfate,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1O[C@@H](C1=CC(O[Si](C)(C)C(C)(C)C)=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](OS(=O)(=O)[O-])C2	4154.8	Semi standard non polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epigallocatechin sulfate 10V, Negative-QTOF	splash10-000i-0019000000-d23675a96e9da813f4c6	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epigallocatechin sulfate 20V, Negative-QTOF	splash10-0pbi-0439000000-d2472e812e86e561479a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epigallocatechin sulfate 40V, Negative-QTOF	splash10-00c0-3920000000-6a2d7d8a8670e7efaa17	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epigallocatechin sulfate 10V, Negative-QTOF	splash10-000i-0009000000-e4c1fecc413d44d5ffae	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epigallocatechin sulfate 20V, Negative-QTOF	splash10-014s-2229000000-51a3b9689ffa58e80f29	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-Epigallocatechin sulfate 40V, Negative-QTOF	splash10-00rb-9815000000-b1389a1e35d5667d8c65	2021-09-25	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	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

30776611

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481415

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Ai Z, Liu S, Qu F, Zhang H, Chen Y, Ni D: Effect of Stereochemical Configuration on the Transport and Metabolism of Catechins from Green Tea across Caco-2 Monolayers. Molecules. 2019 Mar 26;24(6). pii: molecules24061185. doi: 10.3390/molecules24061185. [PubMed:30917581 ]

Showing metabocard for (-)-Epigallocatechin sulfate (HMDB0012468)

MOL for HMDB0012468 ((-)-Epigallocatechin sulfate)

3D MOL for HMDB0012468 ((-)-Epigallocatechin sulfate)

3D SDF for HMDB0012468 ((-)-Epigallocatechin sulfate)

3D-SDF for HMDB0012468 ((-)-Epigallocatechin sulfate)

PDB for HMDB0012468 ((-)-Epigallocatechin sulfate)

3D PDB for HMDB0012468 ((-)-Epigallocatechin sulfate)

SMILES for HMDB0012468 ((-)-Epigallocatechin sulfate)

INCHI for HMDB0012468 ((-)-Epigallocatechin sulfate)

Structure for HMDB0012468 ((-)-Epigallocatechin sulfate)

3D Structure for HMDB0012468 ((-)-Epigallocatechin sulfate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

MS/MS Spectra