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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:44:19 UTC

Update Date

2021-09-23 19:44:19 UTC

HMDB ID

HMDB0302684

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Feruloylquinic acid

Description

3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl 1,3,4,5-tetrahydroxycyclohexane-1-carboxylate belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. Based on a literature review very few articles have been published on 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl 1,3,4,5-tetrahydroxycyclohexane-1-carboxylate.

Structure

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

  Mrv1533004251503482D          

 26 27  0  0  0  0            999 V2000
   -4.5926    1.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782    1.3218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782    0.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637    0.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637   -0.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -1.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -1.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347   -2.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347   -3.2157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -1.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058   -2.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058   -3.2157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087   -1.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908   -2.7534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1216   -1.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1605   -0.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3698    0.0610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9730   -0.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2552    0.3476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5033   -1.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3158   -0.9164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2211   -1.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782   -1.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5926   -0.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5926    0.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3071    0.4968    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
  5 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END

HMDB0302684
     RDKit          3D
Feruloylquinic acid
 46 47  0  0  0  0  0  0  0  0999 V2000
    5.4720    1.3620    2.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3586    0.7670    1.4531 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9409    0.0602    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -0.1100    0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -0.8137   -1.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7834   -1.0063   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320   -0.5176   -0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4351   -0.7530   -0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1488   -1.4169   -2.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6297   -0.2656   -0.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9523   -0.4841   -0.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2153   -1.1450   -1.6316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347    0.0557    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5506    0.7590    1.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9236    1.0161   -0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7604    1.7209    0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4935    2.7622   -0.0522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6109    0.7301    1.2486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9491    1.0049    0.8956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3435   -0.6964    0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1210   -1.0675   -0.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9154   -1.0480    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418   -1.3611   -1.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4672   -1.1930   -1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8860   -0.4843   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2613   -0.3273   -0.2253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7325    2.0016    1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0865    1.9708    3.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917    0.5727    2.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8964    0.3424    0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475   -1.5903   -2.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0396    0.0439    0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622    0.0816    2.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5356    0.4089   -1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3211    1.7939   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0159    2.1752    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8288    3.3153    0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5444    0.9200    2.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9647    1.1066   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7437   -1.3259    1.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5824   -1.7023   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4457   -1.4747    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8400   -1.8846   -0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8290   -1.9226   -2.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1812   -1.6375   -2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8952   -0.7435   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
  5 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  3  1  0
 22 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 26 46  1  0
M  END

  Mrv1533004251503482D          

 26 27  0  0  0  0            999 V2000
   -4.5926    1.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782    1.3218    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782    0.4968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637    0.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1637   -0.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -1.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4492   -1.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347   -2.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7347   -3.2157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0203   -1.9782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058   -2.3907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058   -3.2157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4087   -1.9782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6908   -2.7534    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1216   -1.3462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1605   -0.5710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3698    0.0610    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9730   -0.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2552    0.3476    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5033   -1.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3158   -0.9164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2211   -1.8349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8782   -1.1532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5926   -0.7407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5926    0.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3071    0.4968    0.0000 O   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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 13 22  1  0  0  0  0
  5 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
  3 25  1  0  0  0  0
 25 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302684

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(C=CC(=O)OC(=O)C2(O)CC(O)C(O)C(O)C2)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C17H20O9/c1-25-13-6-9(2-4-10(13)18)3-5-14(21)26-16(23)17(24)7-11(19)15(22)12(20)8-17/h2-6,11-12,15,18-20,22,24H,7-8H2,1H3

> <INCHI_KEY>
MOKUYUICRPXHER-UHFFFAOYSA-N

> <FORMULA>
C17H20O9

> <MOLECULAR_WEIGHT>
368.338

> <EXACT_MASS>
368.110732224

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
35.61157837818828

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl 1,3,4,5-tetrahydroxycyclohexane-1-carboxylate

> <ALOGPS_LOGP>
0.06

> <JCHEM_LOGP>
-0.652934816333333

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.10123252396582

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.863915231912367

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2311208796397777

> <JCHEM_POLAR_SURFACE_AREA>
153.75

> <JCHEM_REFRACTIVITY>
88.0038

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.09e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl 1,3,4,5-tetrahydroxycyclohexane-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302684
     RDKit          3D
Feruloylquinic acid
 46 47  0  0  0  0  0  0  0  0999 V2000
    5.4720    1.3620    2.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3586    0.7670    1.4531 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9409    0.0602    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -0.1100    0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -0.8137   -1.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7834   -1.0063   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320   -0.5176   -0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4351   -0.7530   -0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1488   -1.4169   -2.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6297   -0.2656   -0.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9523   -0.4841   -0.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2153   -1.1450   -1.6316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347    0.0557    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5506    0.7590    1.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9236    1.0161   -0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7604    1.7209    0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4935    2.7622   -0.0522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6109    0.7301    1.2486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9491    1.0049    0.8956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3435   -0.6964    0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1210   -1.0675   -0.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9154   -1.0480    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418   -1.3611   -1.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4672   -1.1930   -1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8860   -0.4843   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2613   -0.3273   -0.2253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7325    2.0016    1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0865    1.9708    3.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917    0.5727    2.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8964    0.3424    0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475   -1.5903   -2.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0396    0.0439    0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622    0.0816    2.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5356    0.4089   -1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3211    1.7939   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0159    2.1752    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8288    3.3153    0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5444    0.9200    2.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9647    1.1066   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7437   -1.3259    1.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5824   -1.7023   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4457   -1.4747    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8400   -1.8846   -0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8290   -1.9226   -2.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1812   -1.6375   -2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8952   -0.7435   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
  5 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  3  1  0
 22 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 26 46  1  0
M  END

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -8.573   3.237   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -7.239   2.467   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -7.239   0.927   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.906   0.157   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.906  -1.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.572  -2.153   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.572  -3.693   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.238  -4.463   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.238  -6.003   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.905  -3.693   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.571  -4.463   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.571  -6.003   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.763  -3.693   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.290  -5.140   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -0.227  -2.513   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.300  -1.066   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.690   0.114   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.816  -0.798   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.343   0.649   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.806  -1.978   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       4.323  -1.711   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.279  -3.425   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.239  -2.153   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -8.573  -1.383   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -8.573   0.157   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -9.907   0.927   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   25                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   23                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15   22                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   13                                                       
CONECT   23    5   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24    3   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   54    0
END

COMPND    HMDB0302684
HETATM    1  C1  UNL     1       5.472   1.362   2.367  1.00  0.00           C  
HETATM    2  O1  UNL     1       6.359   0.767   1.453  1.00  0.00           O  
HETATM    3  C2  UNL     1       5.941   0.060   0.348  1.00  0.00           C  
HETATM    4  C3  UNL     1       4.585  -0.110   0.066  1.00  0.00           C  
HETATM    5  C4  UNL     1       4.173  -0.814  -1.035  1.00  0.00           C  
HETATM    6  C5  UNL     1       2.783  -1.006  -1.352  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.832  -0.518  -0.604  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.435  -0.753  -0.988  1.00  0.00           C  
HETATM    9  O2  UNL     1       0.149  -1.417  -2.024  1.00  0.00           O  
HETATM   10  O3  UNL     1      -0.630  -0.266  -0.243  1.00  0.00           O  
HETATM   11  C8  UNL     1      -1.952  -0.484  -0.600  1.00  0.00           C  
HETATM   12  O4  UNL     1      -2.215  -1.145  -1.632  1.00  0.00           O  
HETATM   13  C9  UNL     1      -3.035   0.056   0.226  1.00  0.00           C  
HETATM   14  O5  UNL     1      -2.551   0.759   1.326  1.00  0.00           O  
HETATM   15  C10 UNL     1      -3.924   1.016  -0.577  1.00  0.00           C  
HETATM   16  C11 UNL     1      -4.760   1.721   0.499  1.00  0.00           C  
HETATM   17  O6  UNL     1      -5.494   2.762  -0.052  1.00  0.00           O  
HETATM   18  C12 UNL     1      -5.611   0.730   1.249  1.00  0.00           C  
HETATM   19  O7  UNL     1      -6.949   1.005   0.896  1.00  0.00           O  
HETATM   20  C13 UNL     1      -5.344  -0.696   0.874  1.00  0.00           C  
HETATM   21  O8  UNL     1      -6.121  -1.067  -0.244  1.00  0.00           O  
HETATM   22  C14 UNL     1      -3.915  -1.048   0.701  1.00  0.00           C  
HETATM   23  C15 UNL     1       5.142  -1.361  -1.874  1.00  0.00           C  
HETATM   24  C16 UNL     1       6.467  -1.193  -1.595  1.00  0.00           C  
HETATM   25  C17 UNL     1       6.886  -0.484  -0.487  1.00  0.00           C  
HETATM   26  O9  UNL     1       8.261  -0.327  -0.225  1.00  0.00           O  
HETATM   27  H1  UNL     1       4.732   2.002   1.830  1.00  0.00           H  
HETATM   28  H2  UNL     1       6.086   1.971   3.082  1.00  0.00           H  
HETATM   29  H3  UNL     1       4.992   0.573   2.964  1.00  0.00           H  
HETATM   30  H4  UNL     1       3.896   0.342   0.761  1.00  0.00           H  
HETATM   31  H5  UNL     1       2.547  -1.590  -2.264  1.00  0.00           H  
HETATM   32  H6  UNL     1       2.040   0.044   0.273  1.00  0.00           H  
HETATM   33  H7  UNL     1      -2.362   0.082   2.025  1.00  0.00           H  
HETATM   34  H8  UNL     1      -4.536   0.409  -1.246  1.00  0.00           H  
HETATM   35  H9  UNL     1      -3.321   1.794  -1.069  1.00  0.00           H  
HETATM   36  H10 UNL     1      -4.016   2.175   1.190  1.00  0.00           H  
HETATM   37  H11 UNL     1      -5.829   3.315   0.698  1.00  0.00           H  
HETATM   38  H12 UNL     1      -5.544   0.920   2.339  1.00  0.00           H  
HETATM   39  H13 UNL     1      -6.965   1.107  -0.089  1.00  0.00           H  
HETATM   40  H14 UNL     1      -5.744  -1.326   1.719  1.00  0.00           H  
HETATM   41  H15 UNL     1      -5.582  -1.702  -0.790  1.00  0.00           H  
HETATM   42  H16 UNL     1      -3.446  -1.475   1.628  1.00  0.00           H  
HETATM   43  H17 UNL     1      -3.840  -1.885  -0.052  1.00  0.00           H  
HETATM   44  H18 UNL     1       4.829  -1.923  -2.752  1.00  0.00           H  
HETATM   45  H19 UNL     1       7.181  -1.638  -2.278  1.00  0.00           H  
HETATM   46  H20 UNL     1       8.895  -0.743  -0.865  1.00  0.00           H  
CONECT    1    2   27   28   29
CONECT    2    3
CONECT    3    4    4   25
CONECT    4    5   30
CONECT    5    6   23   23
CONECT    6    7    7   31
CONECT    7    8   32
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   12   13
CONECT   13   14   15   22
CONECT   14   33
CONECT   15   16   34   35
CONECT   16   17   18   36
CONECT   17   37
CONECT   18   19   20   38
CONECT   19   39
CONECT   20   21   22   40
CONECT   21   41
CONECT   22   42   43
CONECT   23   24   44
CONECT   24   25   25   45
CONECT   25   26
CONECT   26   46
END

HMDB0302684
     RDKit          3D
Feruloylquinic acid
 46 47  0  0  0  0  0  0  0  0999 V2000
    5.4720    1.3620    2.3675 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3586    0.7670    1.4531 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9409    0.0602    0.3480 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5846   -0.1100    0.0658 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1731   -0.8137   -1.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7834   -1.0063   -1.3520 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8320   -0.5176   -0.6039 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4351   -0.7530   -0.9879 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1488   -1.4169   -2.0245 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6297   -0.2656   -0.2432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9523   -0.4841   -0.6000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2153   -1.1450   -1.6316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0347    0.0557    0.2259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5506    0.7590    1.3259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9236    1.0161   -0.5773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7604    1.7209    0.4987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4935    2.7622   -0.0522 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6109    0.7301    1.2486 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9491    1.0049    0.8956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3435   -0.6964    0.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1210   -1.0675   -0.2436 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9154   -1.0480    0.7005 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418   -1.3611   -1.8739 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4672   -1.1930   -1.5953 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8860   -0.4843   -0.4872 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2613   -0.3273   -0.2253 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7325    2.0016    1.8295 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0865    1.9708    3.0822 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9917    0.5727    2.9641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8964    0.3424    0.7608 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5475   -1.5903   -2.2637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0396    0.0439    0.2726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3622    0.0816    2.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5356    0.4089   -1.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3211    1.7939   -1.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0159    2.1752    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8288    3.3153    0.6985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5444    0.9200    2.3395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9647    1.1066   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7437   -1.3259    1.7195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5824   -1.7023   -0.7901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4457   -1.4747    1.6277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8400   -1.8846   -0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8290   -1.9226   -2.7516 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1812   -1.6375   -2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8952   -0.7435   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  3
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
  5 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 25  3  1  0
 22 13  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  7 32  1  0
 14 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 21 41  1  0
 22 42  1  0
 22 43  1  0
 23 44  1  0
 24 45  1  0
 26 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(4-Hydroxy-3-methoxyphenyl)prop-2-enoyl 1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid	Generator
Feruloylquinate	Generator

Chemical Formula

C₁₇H₂₀O₉

Average Molecular Weight

368.338

Monoisotopic Molecular Weight

368.110732224

IUPAC Name

3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl 1,3,4,5-tetrahydroxycyclohexane-1-carboxylate

Traditional Name

3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl 1,3,4,5-tetrahydroxycyclohexane-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC1=CC(C=CC(=O)OC(=O)C2(O)CC(O)C(O)C(O)C2)=CC=C1O

InChI Identifier

InChI=1S/C17H20O9/c1-25-13-6-9(2-4-10(13)18)3-5-14(21)26-16(23)17(24)7-11(19)15(22)12(20)8-17/h2-6,11-12,15,18-20,22,24H,7-8H2,1H3

InChI Key

MOKUYUICRPXHER-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, And 5, as well as a carboxylic acid at position 1.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Quinic acids and derivatives

Alternative Parents

Substituents

Quinic acid
Cinnamic acid or derivatives
Coumaric acid or derivatives
Hydroxycinnamic acid or derivatives
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
Styrene
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Cyclohexanol
Benzenoid
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Carboxylic acid anhydride
Tertiary alcohol
Secondary alcohol
Polyol
Carboxylic acid derivative
Ether
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302684)

Food

Cereal and cereal product

Cereal

Barley (FooDB: FOOD00088)
Corn (FooDB: FOOD00205)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	0.06	ALOGPS
logP	-0.65	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.86	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	153.75 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	88 m³·mol⁻¹	ChemAxon
Polarizability	35.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	186.066	32859911
AllCCS	[M+H-H2O]+	183.268	32859911
AllCCS	[M+Na]+	189.387	32859911
AllCCS	[M+NH4]+	188.648	32859911
AllCCS	[M-H]-	182.478	32859911
AllCCS	[M+Na-2H]-	182.717	32859911
AllCCS	[M+HCOO]-	183.116	32859911
DeepCCS	[M+H]+	176.114	30932474
DeepCCS	[M-H]-	173.645	30932474
DeepCCS	[M-2H]-	208.048	30932474
DeepCCS	[M+Na]+	183.636	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloylquinic acid 10V, Positive-QTOF	splash10-004i-0903000000-a1eb3a65a0c58a22debc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloylquinic acid 20V, Positive-QTOF	splash10-004i-0901000000-099f5ae33019e6c41ed5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloylquinic acid 40V, Positive-QTOF	splash10-056r-1900000000-3429b2d9897941bc1e3a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloylquinic acid 10V, Negative-QTOF	splash10-004i-0902000000-ac4aeffef5a807bcaeff	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloylquinic acid 20V, Negative-QTOF	splash10-00bd-0911000000-3fe4f1a7721118117fd8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloylquinic acid 40V, Negative-QTOF	splash10-002b-2900000000-5cd37740768e4a6ba3bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloylquinic acid 10V, Positive-QTOF	splash10-0159-0309000000-ea153f4dcce6de93fa08	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloylquinic acid 20V, Positive-QTOF	splash10-0002-1900000000-e000c30688cd31e0d062	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloylquinic acid 40V, Positive-QTOF	splash10-004j-9510000000-b725e0cb443cab439bf0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloylquinic acid 10V, Negative-QTOF	splash10-014l-0907000000-2efc6d6e9de9e182b523	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloylquinic acid 20V, Negative-QTOF	splash10-003r-0953000000-ff75b95c2ad7dfd99677	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Feruloylquinic acid 40V, Negative-QTOF	splash10-00m0-3921000000-71245c353f8b20ed3b89	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005768

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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

Not Available

Showing metabocard for Feruloylquinic acid (HMDB0302684)

MOL for HMDB0302684 (Feruloylquinic acid)

3D MOL for HMDB0302684 (Feruloylquinic acid)

3D SDF for HMDB0302684 (Feruloylquinic acid)

3D-SDF for HMDB0302684 (Feruloylquinic acid)

PDB for HMDB0302684 (Feruloylquinic acid)

3D PDB for HMDB0302684 (Feruloylquinic acid)

SMILES for HMDB0302684 (Feruloylquinic acid)

INCHI for HMDB0302684 (Feruloylquinic acid)

Structure for HMDB0302684 (Feruloylquinic acid)

3D Structure for HMDB0302684 (Feruloylquinic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra