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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:50 UTC

Update Date

2022-03-07 02:49:15 UTC

HMDB ID

HMDB0002375

Secondary Accession Numbers

HMDB02375

Metabolite Identification

Common Name

Chicoric acid

Description

Chicoric acid (CAS: 6537-80-0) is found in the fresh aerial parts of different chicory varieties: green chicory (c.v. Catalogna), two red chicory varieties (radicchio rosso di Chioggia and radicchio rosso di Treviso), and Witloof or Belgian endive. Cichorium sp. L. is a member of the sunflower family (Asteraceae or Compositae), which also includes globe and Jerusalem artichokes, lettuce, and many ornamental plants. It is indigenous to Europe, western Asia, Egypt, and North America. In popular medicine, Cichorium intybus L. has been used to treat skin disorders, such as gout, because of its antihepatotoxic activity. Animal studies have revealed that preparations from chicory roots can lower serum and liver lipid concentration in rats. Cichorium aqueous extracts from roots and aerial parts have been reported for antibacterial activity. Chicory is used as a vegetable, fresh or cooked, while the ground and roasted roots are widely used for blending with coffee powder (PMID: 16076140 ). Chicoric acid inhibits human immunodeficiency virus type 1 integration in vivo and is a noncompetitive but reversible inhibitor of HIV-1 integrase in vitro (PMID: 15302207 ).

Structure

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


  Mrv1652307191923412D          

 34 35  0  0  0  0            999 V2000
10001.108310000.9607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.393910000.5482    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.679910000.9607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.966110000.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.252210000.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.538410000.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.108610003.0216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.680810002.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9661 9999.7238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3939 9999.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6799 9999.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1083 9999.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.821410000.5482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.536510000.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.249610000.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.962710000.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.3929 9998.4881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.8190 9999.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.536510001.7851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.108310001.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.821410002.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.393910002.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.109210002.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.394710001.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.394710000.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.109210000.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.823710000.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.823710001.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.106710000.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.392310000.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.677610000.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.6776 9999.7236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.3922 9999.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.1067 9999.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  1 20  1  6  0  0  0
  2  3  1  0  0  0  0
  2 10  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  2  0  0  0  0
 15 16  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 23  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 29  1  0  0  0  0
 16 31  1  0  0  0  0
 33 17  1  0  0  0  0
 34 18  1  0  0  0  0
  6 27  1  0  0  0  0
 23  7  1  0  0  0  0
 24  8  1  0  0  0  0
M  END

HMDB0002375
     RDKit          3D
Chicoric acid
 52 53  0  0  0  0  0  0  0  0999 V2000
    2.7853    2.7593    0.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3783    2.0092   -0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917    0.6340   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4929   -0.1908   -1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9571   -1.5507   -1.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665   -2.1750   -0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2980   -3.4694   -0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897   -4.2120   -1.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2140   -5.5425   -2.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8729   -3.6231   -2.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789   -4.3961   -3.8475 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4569   -2.3050   -2.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4587    2.5334   -1.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722    3.8883   -1.1056 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3217    4.6514   -2.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547    4.0020   -3.2763 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1545    5.9901   -2.5333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    3.8456   -0.8697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7773    3.0644    0.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820    1.9374    0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708    1.6354   -0.8393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8751    1.1121    1.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536    0.0633    1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198   -0.8349    2.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953   -0.6892    3.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9797   -1.5861    4.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7911   -2.6214    4.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2018   -3.5401    5.2769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2345   -2.8020    3.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0614   -3.8696    2.7253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8511   -1.9174    2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0406    5.2115   -0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884    5.4969    0.4919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1138    6.2152   -1.6010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6006    0.2858    0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599    0.2481   -2.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2803   -1.6202    0.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0186   -3.9401   -0.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8034   -6.0265   -2.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7069   -4.0693   -4.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7388   -1.9252   -3.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827    4.3143   -0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9379    6.3713   -3.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0648    3.3648   -1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4826    1.3255    2.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0594   -0.1610    0.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9538    0.1407    3.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092   -1.4131    5.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7993   -4.3197    5.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3843   -4.0014    1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1941   -2.0476    1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0685    7.1776   -1.3607 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  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 18 32  1  0
 32 33  2  0
 32 34  1  0
 12  5  1  0
 31 24  1  0
  3 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  1
 17 43  1  0
 18 44  1  6
 22 45  1  0
 23 46  1  0
 25 47  1  0
 26 48  1  0
 28 49  1  0
 30 50  1  0
 31 51  1  0
 34 52  1  0
M  END


  Mrv1652307191923412D          

 34 35  0  0  0  0            999 V2000
10001.108310000.9607    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.393910000.5482    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.679910000.9607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.966110000.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.252210000.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.538410000.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.108610003.0216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9994.680810002.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9661 9999.7238    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.3939 9999.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6799 9999.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.1083 9999.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.821410000.5482    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.536510000.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.249610000.5482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.962710000.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.3929 9998.4881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10006.8190 9999.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.536510001.7851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.108310001.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.821410002.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.393910002.1972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.109210002.1979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.394710001.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.394710000.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.109210000.5477    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.823710000.9602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.823710001.7854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.106710000.5488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.392310000.9612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.677610000.5487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10004.6776 9999.7236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.3922 9999.3111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10006.1067 9999.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  1  0  0  0  0
  1 20  1  6  0  0  0
  2  3  1  0  0  0  0
  2 10  1  6  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  9  2  0  0  0  0
  5  6  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 19  2  0  0  0  0
 15 16  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 23  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 29  1  0  0  0  0
 16 31  1  0  0  0  0
 33 17  1  0  0  0  0
 34 18  1  0  0  0  0
  6 27  1  0  0  0  0
 23  7  1  0  0  0  0
 24  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002375

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)[C@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)[C@@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1

> <INCHI_KEY>
YDDGKXBLOXEEMN-IABMMNSOSA-N

> <FORMULA>
C22H18O12

> <MOLECULAR_WEIGHT>
474.3711

> <EXACT_MASS>
474.07982604

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
44.09365132505789

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid

> <ALOGPS_LOGP>
3.48

> <JCHEM_LOGP>
3.0247202606666663

> <ALOGPS_LOGS>
-4.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.684576453831155

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.7169409199418117

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283762525890698

> <JCHEM_POLAR_SURFACE_AREA>
208.11999999999998

> <JCHEM_REFRACTIVITY>
113.2724

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.30e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
cichoric acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002375
     RDKit          3D
Chicoric acid
 52 53  0  0  0  0  0  0  0  0999 V2000
    2.7853    2.7593    0.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3783    2.0092   -0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917    0.6340   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4929   -0.1908   -1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9571   -1.5507   -1.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665   -2.1750   -0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2980   -3.4694   -0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897   -4.2120   -1.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2140   -5.5425   -2.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8729   -3.6231   -2.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789   -4.3961   -3.8475 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4569   -2.3050   -2.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4587    2.5334   -1.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722    3.8883   -1.1056 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3217    4.6514   -2.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547    4.0020   -3.2763 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1545    5.9901   -2.5333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    3.8456   -0.8697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7773    3.0644    0.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820    1.9374    0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708    1.6354   -0.8393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8751    1.1121    1.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536    0.0633    1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198   -0.8349    2.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953   -0.6892    3.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9797   -1.5861    4.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7911   -2.6214    4.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2018   -3.5401    5.2769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2345   -2.8020    3.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0614   -3.8696    2.7253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8511   -1.9174    2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0406    5.2115   -0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884    5.4969    0.4919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1138    6.2152   -1.6010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6006    0.2858    0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599    0.2481   -2.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2803   -1.6202    0.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0186   -3.9401   -0.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8034   -6.0265   -2.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7069   -4.0693   -4.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7388   -1.9252   -3.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827    4.3143   -0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9379    6.3713   -3.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0648    3.3648   -1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4826    1.3255    2.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0594   -0.1610    0.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9538    0.1407    3.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092   -1.4131    5.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7993   -4.3197    5.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3843   -4.0014    1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1941   -2.0476    1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0685    7.1776   -1.3607 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  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 18 32  1  0
 32 33  2  0
 32 34  1  0
 12  5  1  0
 31 24  1  0
  3 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  1
 17 43  1  0
 18 44  1  6
 22 45  1  0
 23 46  1  0
 25 47  1  0
 26 48  1  0
 28 49  1  0
 30 50  1  0
 31 51  1  0
 34 52  1  0
M  END

HEADER    PROTEIN                                 19-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUL-19         0                                  
HETATM    1  C   UNK     0    8668.7358668.460   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.4028667.690   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8666.0698668.460   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0    8664.7378667.690   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8663.4048668.460   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8662.0728667.690   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8659.4038672.307   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8656.7378670.768   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8664.7378666.151   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0    8667.4028666.151   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8666.0698665.383   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8668.7358665.383   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8670.0678667.690   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8671.4018668.460   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8672.7338667.690   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8674.0648668.460   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0    8676.7338663.844   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0    8679.3958665.383   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0    8671.4018669.999   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0    8668.7358669.999   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0    8670.0678670.768   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0    8667.4028670.768   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0    8659.4048670.769   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8658.0708669.999   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0    8658.0708668.459   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0    8659.4048667.689   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0    8660.7388668.459   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0    8660.7388669.999   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0    8678.0668667.691   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0    8676.7328668.461   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0    8675.3988667.691   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0    8675.3988666.151   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0    8676.7328665.381   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0    8678.0668666.151   0.000  0.00  0.00           C+0
CONECT    1    2   13   20                                                  
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5   27                                                       
CONECT    7   23                                                            
CONECT    8   24                                                            
CONECT    9    4                                                            
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    1   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   31                                                       
CONECT   17   33                                                            
CONECT   18   34                                                            
CONECT   19   14                                                            
CONECT   20    1   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   24   28    7                                                  
CONECT   24   23   25    8                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28    6                                                  
CONECT   28   27   23                                                       
CONECT   29   30   34                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   16                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   17                                                  
CONECT   34   33   29   18                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   70    0
END

COMPND    HMDB0002375
HETATM    1  O1  UNL     1       2.785   2.759   0.575  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.378   2.009  -0.349  1.00  0.00           C  
HETATM    3  C2  UNL     1       2.892   0.634  -0.449  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.493  -0.191  -1.404  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.957  -1.551  -1.558  1.00  0.00           C  
HETATM    6  C5  UNL     1       3.867  -2.175  -0.746  1.00  0.00           C  
HETATM    7  C6  UNL     1       4.298  -3.469  -0.906  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.790  -4.212  -1.957  1.00  0.00           C  
HETATM    9  O2  UNL     1       4.214  -5.543  -2.147  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.873  -3.623  -2.798  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.379  -4.396  -3.847  1.00  0.00           O  
HETATM   12  C9  UNL     1       2.457  -2.305  -2.605  1.00  0.00           C  
HETATM   13  O4  UNL     1       1.459   2.533  -1.228  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.972   3.888  -1.106  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.322   4.651  -2.307  1.00  0.00           C  
HETATM   16  O5  UNL     1       1.855   4.002  -3.276  1.00  0.00           O  
HETATM   17  O6  UNL     1       1.154   5.990  -2.533  1.00  0.00           O  
HETATM   18  C12 UNL     1      -0.521   3.846  -0.870  1.00  0.00           C  
HETATM   19  O7  UNL     1      -0.777   3.064   0.316  1.00  0.00           O  
HETATM   20  C13 UNL     1      -1.582   1.937   0.274  1.00  0.00           C  
HETATM   21  O8  UNL     1      -2.071   1.635  -0.839  1.00  0.00           O  
HETATM   22  C14 UNL     1      -1.875   1.112   1.440  1.00  0.00           C  
HETATM   23  C15 UNL     1      -2.654   0.063   1.281  1.00  0.00           C  
HETATM   24  C16 UNL     1      -3.020  -0.835   2.359  1.00  0.00           C  
HETATM   25  C17 UNL     1      -2.595  -0.689   3.667  1.00  0.00           C  
HETATM   26  C18 UNL     1      -2.980  -1.586   4.665  1.00  0.00           C  
HETATM   27  C19 UNL     1      -3.791  -2.621   4.323  1.00  0.00           C  
HETATM   28  O9  UNL     1      -4.202  -3.540   5.277  1.00  0.00           O  
HETATM   29  C20 UNL     1      -4.235  -2.802   3.038  1.00  0.00           C  
HETATM   30  O10 UNL     1      -5.061  -3.870   2.725  1.00  0.00           O  
HETATM   31  C21 UNL     1      -3.851  -1.917   2.071  1.00  0.00           C  
HETATM   32  C22 UNL     1      -1.041   5.212  -0.685  1.00  0.00           C  
HETATM   33  O11 UNL     1      -1.488   5.497   0.492  1.00  0.00           O  
HETATM   34  O12 UNL     1      -1.114   6.215  -1.601  1.00  0.00           O  
HETATM   35  H1  UNL     1       3.601   0.286   0.259  1.00  0.00           H  
HETATM   36  H2  UNL     1       1.760   0.248  -2.093  1.00  0.00           H  
HETATM   37  H3  UNL     1       4.280  -1.620   0.083  1.00  0.00           H  
HETATM   38  H4  UNL     1       5.019  -3.940  -0.249  1.00  0.00           H  
HETATM   39  H5  UNL     1       3.803  -6.026  -2.933  1.00  0.00           H  
HETATM   40  H6  UNL     1       1.707  -4.069  -4.521  1.00  0.00           H  
HETATM   41  H7  UNL     1       1.739  -1.925  -3.309  1.00  0.00           H  
HETATM   42  H8  UNL     1       1.483   4.314  -0.228  1.00  0.00           H  
HETATM   43  H9  UNL     1       0.938   6.371  -3.444  1.00  0.00           H  
HETATM   44  H10 UNL     1      -1.065   3.365  -1.691  1.00  0.00           H  
HETATM   45  H11 UNL     1      -1.483   1.325   2.416  1.00  0.00           H  
HETATM   46  H12 UNL     1      -3.059  -0.161   0.281  1.00  0.00           H  
HETATM   47  H13 UNL     1      -1.954   0.141   3.904  1.00  0.00           H  
HETATM   48  H14 UNL     1      -2.609  -1.413   5.677  1.00  0.00           H  
HETATM   49  H15 UNL     1      -4.799  -4.320   5.077  1.00  0.00           H  
HETATM   50  H16 UNL     1      -5.384  -4.001   1.789  1.00  0.00           H  
HETATM   51  H17 UNL     1      -4.194  -2.048   1.050  1.00  0.00           H  
HETATM   52  H18 UNL     1      -1.068   7.178  -1.361  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   35
CONECT    4    5   36
CONECT    5    6    6   12
CONECT    6    7   37
CONECT    7    8    8   38
CONECT    8    9   10
CONECT    9   39
CONECT   10   11   12   12
CONECT   11   40
CONECT   12   41
CONECT   13   14
CONECT   14   15   18   42
CONECT   15   16   16   17
CONECT   17   43
CONECT   18   19   32   44
CONECT   19   20
CONECT   20   21   21   22
CONECT   22   23   23   45
CONECT   23   24   46
CONECT   24   25   25   31
CONECT   25   26   47
CONECT   26   27   27   48
CONECT   27   28   29
CONECT   28   49
CONECT   29   30   31   31
CONECT   30   50
CONECT   31   51
CONECT   32   33   33   34
CONECT   34   52
END

HMDB0002375
     RDKit          3D
Chicoric acid
 52 53  0  0  0  0  0  0  0  0999 V2000
    2.7853    2.7593    0.5746 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3783    2.0092   -0.3493 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917    0.6340   -0.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4929   -0.1908   -1.4041 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9571   -1.5507   -1.5581 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8665   -2.1750   -0.7458 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2980   -3.4694   -0.9064 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7897   -4.2120   -1.9574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2140   -5.5425   -2.1471 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8729   -3.6231   -2.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3789   -4.3961   -3.8475 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4569   -2.3050   -2.6051 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4587    2.5334   -1.2276 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9722    3.8883   -1.1056 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3217    4.6514   -2.3071 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8547    4.0020   -3.2763 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1545    5.9901   -2.5333 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5208    3.8456   -0.8697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7773    3.0644    0.3160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820    1.9374    0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0708    1.6354   -0.8393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8751    1.1121    1.4398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6536    0.0633    1.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198   -0.8349    2.3593 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5953   -0.6892    3.6674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9797   -1.5861    4.6650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7911   -2.6214    4.3233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2018   -3.5401    5.2769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2345   -2.8020    3.0378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0614   -3.8696    2.7253 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8511   -1.9174    2.0712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0406    5.2115   -0.6849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4884    5.4969    0.4919 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1138    6.2152   -1.6010 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6006    0.2858    0.2591 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7599    0.2481   -2.0930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2803   -1.6202    0.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0186   -3.9401   -0.2493 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8034   -6.0265   -2.9327 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7069   -4.0693   -4.5213 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7388   -1.9252   -3.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4827    4.3143   -0.2277 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9379    6.3713   -3.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0648    3.3648   -1.6913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4826    1.3255    2.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0594   -0.1610    0.2813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9538    0.1407    3.9039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6092   -1.4131    5.6773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7993   -4.3197    5.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3843   -4.0014    1.7887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1941   -2.0476    1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0685    7.1776   -1.3607 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  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  2  0
 18 32  1  0
 32 33  2  0
 32 34  1  0
 12  5  1  0
 31 24  1  0
  3 35  1  0
  4 36  1  0
  6 37  1  0
  7 38  1  0
  9 39  1  0
 11 40  1  0
 12 41  1  0
 14 42  1  1
 17 43  1  0
 18 44  1  6
 22 45  1  0
 23 46  1  0
 25 47  1  0
 26 48  1  0
 28 49  1  0
 30 50  1  0
 31 51  1  0
 34 52  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Chicate	Generator
Chicic acid	Generator
L-Chicoric acid	HMDB
(-)-L-Chicoric acid	HMDB
2,3-Bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)butanedioic acid	HMDB
(-)-Chicoric acid	HMDB
Cichoric acid	HMDB
Dicaffeoyltartaric acid	HMDB
L-Chicate	HMDB
L-Chicic acid	HMDB
CICHate	HMDB
CICHic acid	HMDB
(2R,3R)-2,3-Bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioate	HMDB
(2R,3R)-2,3-Bis[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]butanedioic acid	HMDB
(2R,3R)-2,3-Bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]butanedioic acid	HMDB
trans-Caffeoyltartaric acid	HMDB
(2R,3R)-2,3-Bis(((2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-butanedioic acid	MeSH
Chicoric acid	MeSH

Chemical Formula

C₂₂H₁₈O₁₂

Average Molecular Weight

474.3711

Monoisotopic Molecular Weight

474.07982604

IUPAC Name

(2R,3R)-2,3-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})butanedioic acid

Traditional Name

cichoric acid

CAS Registry Number

70831-56-0

SMILES

OC(=O)[C@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)[C@@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O

InChI Identifier

InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1

InChI Key

YDDGKXBLOXEEMN-IABMMNSOSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monosaccharide
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Carboxylic acid
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

organooxygen compound (CHEBI:3594 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0002375)

Source

Exogenous

Exogenous (HMDB: HMDB0002375)

Food

Vegetable

Leaf vegetable

Lettuce (FooDB: FOOD00095)

Root vegetable

Chicory (FooDB: FOOD00049)

Process

Not Available

Role

Industrial application

Antiviral agent (HMDB: HMDB0002375)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Immunological adjuvant (HMDB: HMDB0002375)

Agriculture

Pesticide (HMDB: HMDB0002375)

AntiHIV-integrase (HMDB: HMDB0002375)
Hyaluronidase inhibitor (HMDB: HMDB0002375)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	25.62 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.043 g/L	ALOGPS
logP	3.48	ALOGPS
logP	3.02	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	2.72	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	208.12 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	113.27 m³·mol⁻¹	ChemAxon
Polarizability	44.09 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	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
DeepCCS	[M+H]+	199.947	30932474
DeepCCS	[M-H]-	197.551	30932474
DeepCCS	[M-2H]-	230.76	30932474
DeepCCS	[M+Na]+	205.859	30932474
AllCCS	[M+H]+	205.4	32859911
AllCCS	[M+H-H2O]+	203.3	32859911
AllCCS	[M+NH4]+	207.3	32859911
AllCCS	[M+Na]+	207.9	32859911
AllCCS	[M-H]-	200.9	32859911
AllCCS	[M+Na-2H]-	201.5	32859911
AllCCS	[M+HCOO]-	202.2	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.62 minutes	32390414
Predicted by Siyang on May 30, 2022	12.4896 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.99 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	72.9 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1603.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	192.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	94.4 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	136.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	76.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	534.5 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	358.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	549.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	860.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	413.4 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	1424.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	222.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	498.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	185.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	231.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Chicoric acid	OC(=O)[C@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)[C@@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O	7729.7	Standard polar	33892256
Chicoric acid	OC(=O)[C@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)[C@@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O	4115.8	Standard non polar	33892256
Chicoric acid	OC(=O)[C@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)[C@@H](OC(=O)\C=C\C1=CC(O)=C(O)C=C1)C(O)=O	4552.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Chicoric acid,1TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O	4450.4	Semi standard non polar	33892256
Chicoric acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(=O)O)=CC=C1O	4403.8	Semi standard non polar	33892256
Chicoric acid,1TMS,isomer #3	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(=O)O)C=C1O	4418.2	Semi standard non polar	33892256
Chicoric acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O	4268.4	Semi standard non polar	33892256
Chicoric acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O	4268.6	Semi standard non polar	33892256
Chicoric acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O	4268.1	Semi standard non polar	33892256
Chicoric acid,2TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O	4268.3	Semi standard non polar	33892256
Chicoric acid,2TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O[Si](C)(C)C	4368.9	Semi standard non polar	33892256
Chicoric acid,2TMS,isomer #6	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)C(=O)O)C=C1O	4318.5	Semi standard non polar	33892256
Chicoric acid,2TMS,isomer #7	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)C(=O)O)=CC=C1O	4316.1	Semi standard non polar	33892256
Chicoric acid,2TMS,isomer #8	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(=O)O)C=C1O[Si](C)(C)C	4365.2	Semi standard non polar	33892256
Chicoric acid,2TMS,isomer #9	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O)=C2)C(=O)O)C=C1O	4319.1	Semi standard non polar	33892256
Chicoric acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O	4228.7	Semi standard non polar	33892256
Chicoric acid,3TMS,isomer #10	C[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(=O)O)=CC=C1O	4269.2	Semi standard non polar	33892256
Chicoric acid,3TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O	4214.4	Semi standard non polar	33892256
Chicoric acid,3TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O	4215.4	Semi standard non polar	33892256
Chicoric acid,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O[Si](C)(C)C	4146.0	Semi standard non polar	33892256
Chicoric acid,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O	4215.5	Semi standard non polar	33892256
Chicoric acid,3TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O	4212.4	Semi standard non polar	33892256
Chicoric acid,3TMS,isomer #7	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	4145.9	Semi standard non polar	33892256
Chicoric acid,3TMS,isomer #8	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O	4228.9	Semi standard non polar	33892256
Chicoric acid,3TMS,isomer #9	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(=O)O)C=C1O	4273.8	Semi standard non polar	33892256
Chicoric acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O	4221.5	Semi standard non polar	33892256
Chicoric acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O	4219.3	Semi standard non polar	33892256
Chicoric acid,4TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	4142.2	Semi standard non polar	33892256
Chicoric acid,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O	4221.7	Semi standard non polar	33892256
Chicoric acid,4TMS,isomer #5	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)C(=O)O[Si](C)(C)C	4182.7	Semi standard non polar	33892256
Chicoric acid,4TMS,isomer #6	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	4189.1	Semi standard non polar	33892256
Chicoric acid,4TMS,isomer #7	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O	4219.4	Semi standard non polar	33892256
Chicoric acid,4TMS,isomer #8	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	4186.6	Semi standard non polar	33892256
Chicoric acid,4TMS,isomer #9	C[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)C(=O)O)C=C1O[Si](C)(C)C	4292.4	Semi standard non polar	33892256
Chicoric acid,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O	4241.5	Semi standard non polar	33892256
Chicoric acid,5TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	4191.1	Semi standard non polar	33892256
Chicoric acid,5TMS,isomer #3	C[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	4195.0	Semi standard non polar	33892256
Chicoric acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O	4721.5	Semi standard non polar	33892256
Chicoric acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(=O)O)=CC=C1O	4651.1	Semi standard non polar	33892256
Chicoric acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(=O)O)C=C1O	4657.0	Semi standard non polar	33892256
Chicoric acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O	4792.9	Semi standard non polar	33892256
Chicoric acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O	4798.9	Semi standard non polar	33892256
Chicoric acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C(=O)O	4792.9	Semi standard non polar	33892256
Chicoric acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O	4798.9	Semi standard non polar	33892256
Chicoric acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C	4882.6	Semi standard non polar	33892256
Chicoric acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)O)C=C1O	4849.6	Semi standard non polar	33892256
Chicoric acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)O)=CC=C1O	4848.1	Semi standard non polar	33892256
Chicoric acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O)C(O)=C2)C(=O)O)C=C1O[Si](C)(C)C(C)(C)C	4814.7	Semi standard non polar	33892256
Chicoric acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)C(=O)O)C=C1O	4847.6	Semi standard non polar	33892256
Chicoric acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)C(=O)O	4942.6	Semi standard non polar	33892256
Chicoric acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC1=CC(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)O)=CC=C1O	5017.8	Semi standard non polar	33892256
Chicoric acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C(=O)O	5025.0	Semi standard non polar	33892256
Chicoric acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O	5017.9	Semi standard non polar	33892256
Chicoric acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C	4930.0	Semi standard non polar	33892256
Chicoric acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C1)C(=O)O	5018.0	Semi standard non polar	33892256
Chicoric acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O	5011.9	Semi standard non polar	33892256
Chicoric acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C	4934.9	Semi standard non polar	33892256
Chicoric acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)[C@H](OC(=O)/C=C/C1=CC=C(O)C(O)=C1)[C@@H](OC(=O)/C=C/C1=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O	4943.3	Semi standard non polar	33892256
Chicoric acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)C(=O)O)C=C1O	5026.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Chicoric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chicoric acid 10V, Positive-QTOF	splash10-01t9-0751900000-666c40c43f01514fc635	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chicoric acid 20V, Positive-QTOF	splash10-03di-0951200000-b0d53c5e3a31d06f1e1d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chicoric acid 40V, Positive-QTOF	splash10-06sj-0910000000-a5421d18e088b260e7ad	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chicoric acid 10V, Negative-QTOF	splash10-0200-0871900000-2624a942972fa2025a0e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chicoric acid 20V, Negative-QTOF	splash10-004i-0930100000-93e452919696a8a1ccbf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chicoric acid 40V, Negative-QTOF	splash10-03fr-0910000000-ed7ecbd57a50e1e58cd2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chicoric acid 10V, Negative-QTOF	splash10-03di-0891300000-62e53736ddd9284622f7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chicoric acid 20V, Negative-QTOF	splash10-00l2-0890000000-f195fd16e0897353b3b5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chicoric acid 40V, Negative-QTOF	splash10-0019-0910000000-c72bb53cd6a92d5b6682	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chicoric acid 10V, Positive-QTOF	splash10-03fr-0800900000-108837d18a9adaf37a5c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chicoric acid 20V, Positive-QTOF	splash10-03di-0910100000-47b49e2f821895747336	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Chicoric acid 40V, Positive-QTOF	splash10-01ws-0900000000-e30270e27bc6f20240a5	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

Not Available

BiGG ID

Not Available

Wikipedia Link

Cichoric acid

METLIN ID

Not Available

PubChem Compound

5281764

PDB ID

Not Available

ChEBI ID

3594

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1701531

References

Synthesis Reference

Zhao, He; Burke, Terrence R., Jr. Facile syntheses of (2R,3R)-(-)- and (2S,3S)-(+)-chicoric acids. Synthetic Communications (1998), 28(4), 737-740.

Material Safety Data Sheet (MSDS)

Not Available

General References

Innocenti M, Gallori S, Giaccherini C, Ieri F, Vincieri FF, Mulinacci N: Evaluation of the phenolic content in the aerial parts of different varieties of Cichorium intybus L. J Agric Food Chem. 2005 Aug 10;53(16):6497-502. [PubMed:16076140 ]
Reinke RA, Lee DJ, McDougall BR, King PJ, Victoria J, Mao Y, Lei X, Reinecke MG, Robinson WE Jr: L-chicoric acid inhibits human immunodeficiency virus type 1 integration in vivo and is a noncompetitive but reversible inhibitor of HIV-1 integrase in vitro. Virology. 2004 Sep 1;326(2):203-19. [PubMed:15302207 ]

Showing metabocard for Chicoric acid (HMDB0002375)

MOL for HMDB0002375 (Chicoric acid)

3D MOL for HMDB0002375 (Chicoric acid)

3D SDF for HMDB0002375 (Chicoric acid)

3D-SDF for HMDB0002375 (Chicoric acid)

PDB for HMDB0002375 (Chicoric acid)

3D PDB for HMDB0002375 (Chicoric acid)

SMILES for HMDB0002375 (Chicoric acid)

INCHI for HMDB0002375 (Chicoric acid)

Structure for HMDB0002375 (Chicoric acid)

3D Structure for HMDB0002375 (Chicoric acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra