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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:30 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0003072

Secondary Accession Numbers

HMDB03072

Metabolite Identification

Common Name

Quinic acid

Description

Quinic acid, also known as quinate, 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. Quinic acid is a sugar acid. It is also a cyclitol, or cyclic polyol. More specifically, quinic acid is a crystalline acid obtained from cinchona bark, coffee beans, tobacco leaves, carrot leaves, apples, peaches, pears, plums, vegetables, etc. Quinic acid can also be made synthetically by hydrolysis of chlorogenic acid. Quinic acid is implicated in the perceived acidity of coffee.

Structure

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


  Mrv1652309042000282D          

 13 13  0  0  0  0            999 V2000
10000.1518 9999.9041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.8661 9999.4913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.151810000.7298    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.1518 9999.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2909 9999.9041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7209 9997.4272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.2909 9998.2528    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7208 9999.9037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0064 9999.4913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.0064 9998.6663    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.7208 9998.2539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.4353 9998.6663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4353 9999.4913    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  8  9  1  0  0  0  0
  8 13  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  1 13  1  0  0  0  0
 13  4  1  6  0  0  0
  9  5  1  6  0  0  0
 10  7  1  6  0  0  0
 11  6  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0003072

> <DATABASE_NAME>
hmdb

> <SMILES>
O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1

> <INCHI_KEY>
AAWZDTNXLSGCEK-WYWMIBKRSA-N

> <FORMULA>
C7H12O6

> <MOLECULAR_WEIGHT>
192.1666

> <EXACT_MASS>
192.063388116

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
17.024273068093038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid

> <ALOGPS_LOGP>
-2.46

> <JCHEM_LOGP>
-2.695289832666667

> <ALOGPS_LOGS>
0.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.018080332672671

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.461222738658171

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2311063356576595

> <JCHEM_POLAR_SURFACE_AREA>
118.22000000000001

> <JCHEM_REFRACTIVITY>
39.7052

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.65e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-quinic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0    8666.9508666.488   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0    8668.2838665.717   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8666.9508668.029   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8666.9508664.946   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8661.6108666.488   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8664.2798661.864   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8661.6108663.405   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8664.2798666.487   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8662.9458665.717   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8662.9458664.177   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8664.2798663.407   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8665.6138664.177   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8665.6138665.717   0.000  0.00  0.00           C+0
CONECT    1    2    3   13                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4   13                                                            
CONECT    5    9                                                            
CONECT    6   11                                                            
CONECT    7   10                                                            
CONECT    8    9   13                                                       
CONECT    9    8   10    5                                                  
CONECT   10    9   11    7                                                  
CONECT   11   10   12    6                                                  
CONECT   12   11   13                                                       
CONECT   13    8   12    1    4                                             
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
Chinic acid	ChEBI
D-Quinic acid	ChEBI
Kinic acid	ChEBI
(-)-Quinic acid	Kegg
Chinate	Generator
D-Quinate	Generator
Kinate	Generator
(-)-Quinate	Generator
Quinate	Generator
(1alpha,3R,4alpha,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid	HMDB
(1Α,3R,4α,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid	HMDB
1,3,4,5-Tetrahydroxycyclohexane-1-carboxylic acid	HMDB
1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid	HMDB
D-(-)-Quinic acid	HMDB
Hexahydro-1,3,4,5-tetrahydroxybenzoic acid	HMDB
Quinic acid	ChEBI

Chemical Formula

C₇H₁₂O₆

Average Molecular Weight

192.1666

Monoisotopic Molecular Weight

192.063388116

IUPAC Name

(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid

Traditional Name

(-)-quinic acid

CAS Registry Number

77-95-2

SMILES

O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5-,7+/m1/s1

InChI Key

AAWZDTNXLSGCEK-WYWMIBKRSA-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
Cyclohexanol
Hydroxy acid
Alpha-hydroxy acid
Tertiary alcohol
Secondary alcohol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

quinic acid (CHEBI:17521 )

Ontology

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	162.5 °C	Not Available
Boiling Point	438.42 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	290 mg/mL at 9 °C	Not Available
LogP	1.19	RADZICKA,A & WOLFENDEN,R (1988)

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Baker	138.474	30932474
[M+H]+	Baker	146.349	30932474
[M-H]-	Not Available	135.4	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000394
[M+H]+	Not Available	146.349	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000394

Predicted Molecular Properties

Property	Value	Source
Water Solubility	765 g/L	ALOGPS
logP	-2.5	ALOGPS
logP	-2.7	ChemAxon
logS	0.6	ALOGPS
pKa (Strongest Acidic)	3.46	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	118.22 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	39.71 m³·mol⁻¹	ChemAxon
Polarizability	17.02 Å³	ChemAxon
Number of Rings	1	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
DeepCCS	[M+H]+	141.958	30932474
DeepCCS	[M-H]-	139.725	30932474
DeepCCS	[M-2H]-	173.096	30932474
DeepCCS	[M+Na]+	147.871	30932474
AllCCS	[M+H]+	143.4	32859911
AllCCS	[M+H-H2O]+	139.4	32859911
AllCCS	[M+NH4]+	147.2	32859911
AllCCS	[M+Na]+	148.3	32859911
AllCCS	[M-H]-	136.0	32859911
AllCCS	[M+Na-2H]-	136.9	32859911
AllCCS	[M+HCOO]-	137.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Quinic acid	O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O	3342.2	Standard polar	33892256
Quinic acid	O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O	1648.2	Standard non polar	33892256
Quinic acid	O[C@@H]1C[C@@](O)(C[C@@H](O)[C@H]1O)C(O)=O	1903.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Quinic acid,1TMS,isomer #1	C[Si](C)(C)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](O)[C@H]1O	1761.4	Semi standard non polar	33892256
Quinic acid,1TMS,isomer #2	C[Si](C)(C)O[C@]1(C(=O)O)C[C@@H](O)[C@H](O)[C@H](O)C1	1824.9	Semi standard non polar	33892256
Quinic acid,1TMS,isomer #3	C[Si](C)(C)O[C@@H]1C[C@@](O)(C(=O)O)C[C@@H](O)[C@@H]1O	1761.4	Semi standard non polar	33892256
Quinic acid,1TMS,isomer #4	C[Si](C)(C)O[C@H]1[C@H](O)C[C@](O)(C(=O)O)C[C@H]1O	1763.9	Semi standard non polar	33892256
Quinic acid,1TMS,isomer #5	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@H](O)C1	1797.7	Semi standard non polar	33892256
Quinic acid,2TMS,isomer #1	C[Si](C)(C)O[C@@H]1C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O)[C@H]1O	1802.0	Semi standard non polar	33892256
Quinic acid,2TMS,isomer #10	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)C1	1766.7	Semi standard non polar	33892256
Quinic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)C1	1740.8	Semi standard non polar	33892256
Quinic acid,2TMS,isomer #3	C[Si](C)(C)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]1O	1788.6	Semi standard non polar	33892256
Quinic acid,2TMS,isomer #4	C[Si](C)(C)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](O)[C@H]1O[Si](C)(C)C	1778.3	Semi standard non polar	33892256
Quinic acid,2TMS,isomer #5	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O)[C@@H](O)[C@H](O)C1	1773.7	Semi standard non polar	33892256
Quinic acid,2TMS,isomer #6	C[Si](C)(C)O[C@H]1[C@H](O)C[C@](O[Si](C)(C)C)(C(=O)O)C[C@H]1O	1835.8	Semi standard non polar	33892256
Quinic acid,2TMS,isomer #7	C[Si](C)(C)O[C@@H]1C[C@@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O)[C@@H]1O	1802.0	Semi standard non polar	33892256
Quinic acid,2TMS,isomer #8	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](O)[C@H](O)[C@H](O[Si](C)(C)C)C1	1740.8	Semi standard non polar	33892256
Quinic acid,2TMS,isomer #9	C[Si](C)(C)O[C@H]1[C@H](O)C[C@](O)(C(=O)O)C[C@H]1O[Si](C)(C)C	1778.3	Semi standard non polar	33892256
Quinic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C)C1	1761.3	Semi standard non polar	33892256
Quinic acid,3TMS,isomer #10	C[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	1776.8	Semi standard non polar	33892256
Quinic acid,3TMS,isomer #2	C[Si](C)(C)O[C@@H]1C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]1O	1849.9	Semi standard non polar	33892256
Quinic acid,3TMS,isomer #3	C[Si](C)(C)O[C@@H]1C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O)[C@H]1O[Si](C)(C)C	1826.9	Semi standard non polar	33892256
Quinic acid,3TMS,isomer #4	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)C1	1780.7	Semi standard non polar	33892256
Quinic acid,3TMS,isomer #5	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	1776.8	Semi standard non polar	33892256
Quinic acid,3TMS,isomer #6	C[Si](C)(C)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1778.9	Semi standard non polar	33892256
Quinic acid,3TMS,isomer #7	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](O)[C@H](O)[C@H](O[Si](C)(C)C)C1	1761.3	Semi standard non polar	33892256
Quinic acid,3TMS,isomer #8	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O)C1	1808.4	Semi standard non polar	33892256
Quinic acid,3TMS,isomer #9	C[Si](C)(C)O[C@H]1[C@H](O)C[C@](O[Si](C)(C)C)(C(=O)O)C[C@H]1O[Si](C)(C)C	1826.9	Semi standard non polar	33892256
Quinic acid,4TMS,isomer #1	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C)C1	1804.1	Semi standard non polar	33892256
Quinic acid,4TMS,isomer #2	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	1821.3	Semi standard non polar	33892256
Quinic acid,4TMS,isomer #3	C[Si](C)(C)O[C@@H]1C[C@](O[Si](C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C)[C@H]1O[Si](C)(C)C	1842.1	Semi standard non polar	33892256
Quinic acid,4TMS,isomer #4	C[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	1811.3	Semi standard non polar	33892256
Quinic acid,4TMS,isomer #5	C[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C)C[C@@H](O)[C@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	1821.3	Semi standard non polar	33892256
Quinic acid,5TMS,isomer #1	C[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)C1	1890.0	Semi standard non polar	33892256
Quinic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](O)[C@H]1O	2010.6	Semi standard non polar	33892256
Quinic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@]1(C(=O)O)C[C@@H](O)[C@H](O)[C@H](O)C1	2073.3	Semi standard non polar	33892256
Quinic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@](O)(C(=O)O)C[C@@H](O)[C@@H]1O	2010.6	Semi standard non polar	33892256
Quinic acid,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)C[C@](O)(C(=O)O)C[C@H]1O	2025.7	Semi standard non polar	33892256
Quinic acid,1TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@H](O)C1	2062.9	Semi standard non polar	33892256
Quinic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O)[C@H]1O	2217.3	Semi standard non polar	33892256
Quinic acid,2TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C1	2242.5	Semi standard non polar	33892256
Quinic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	2215.8	Semi standard non polar	33892256
Quinic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2220.3	Semi standard non polar	33892256
Quinic acid,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2223.5	Semi standard non polar	33892256
Quinic acid,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](O)[C@H](O)C1	2253.4	Semi standard non polar	33892256
Quinic acid,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]1O	2279.6	Semi standard non polar	33892256
Quinic acid,2TBDMS,isomer #7	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O)[C@@H]1O	2217.3	Semi standard non polar	33892256
Quinic acid,2TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	2215.8	Semi standard non polar	33892256
Quinic acid,2TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)C[C@](O)(C(=O)O)C[C@H]1O[Si](C)(C)C(C)(C)C	2223.5	Semi standard non polar	33892256
Quinic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	2459.0	Semi standard non polar	33892256
Quinic acid,3TBDMS,isomer #10	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O)C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	2471.5	Semi standard non polar	33892256
Quinic acid,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O	2486.6	Semi standard non polar	33892256
Quinic acid,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O)[C@H]1O[Si](C)(C)C(C)(C)C	2488.9	Semi standard non polar	33892256
Quinic acid,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	2473.1	Semi standard non polar	33892256
Quinic acid,3TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	2471.5	Semi standard non polar	33892256
Quinic acid,3TBDMS,isomer #6	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@](O)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2467.3	Semi standard non polar	33892256
Quinic acid,3TBDMS,isomer #7	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	2459.0	Semi standard non polar	33892256
Quinic acid,3TBDMS,isomer #8	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O)C1	2481.7	Semi standard non polar	33892256
Quinic acid,3TBDMS,isomer #9	CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@H]1O[Si](C)(C)C(C)(C)C	2488.9	Semi standard non polar	33892256
Quinic acid,4TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)C1	2703.1	Semi standard non polar	33892256
Quinic acid,4TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	2697.9	Semi standard non polar	33892256
Quinic acid,4TBDMS,isomer #3	CC(C)(C)[Si](C)(C)O[C@@H]1C[C@](O[Si](C)(C)C(C)(C)C)(C(=O)O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@H]1O[Si](C)(C)C(C)(C)C	2718.6	Semi standard non polar	33892256
Quinic acid,4TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	2688.9	Semi standard non polar	33892256
Quinic acid,4TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)[C@@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	2697.9	Semi standard non polar	33892256
Quinic acid,5TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@]1(O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](O[Si](C)(C)C(C)(C)C)[C@H](O[Si](C)(C)C(C)(C)C)C1	2905.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Quinic acid GC-MS (5 TMS)	splash10-052b-1985000000-8de0c4f44a72e6fbc96b	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Quinic 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid LC-ESI-QQ 10V, negative-QTOF	splash10-0006-0900000000-39db9f9b730da813fb9c	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid LC-ESI-QQ 20V, negative-QTOF	splash10-0006-0900000000-43c4a73703e8d9acb9cc	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid LC-ESI-QQ 30V, negative-QTOF	splash10-000l-9500000000-ad9d1a4974316f4287b7	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid LC-ESI-QQ 40V, negative-QTOF	splash10-000i-9000000000-2d0277beaea1df617fd1	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid LC-ESI-QQ 50V, negative-QTOF	splash10-052u-9000000000-4ba8c5bdcfbf22e97376	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid LC-ESI-QTOF 32V, negative-QTOF	splash10-0006-3900000000-4856018e3baabc156682	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid n/a 13V, negative-QTOF	splash10-00g0-4900000000-13ef137e25793e6d56f5	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid Orbitrap 6V, negative-QTOF	splash10-0006-0900000000-dd50fbf948027ea3e0d5	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid Orbitrap 8V, negative-QTOF	splash10-0006-2900000000-1b219b4bc23ceb567be5	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid Orbitrap 9V, negative-QTOF	splash10-000f-6900000000-88d72e01e21d18218079	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid Orbitrap 11V, negative-QTOF	splash10-000l-9300000000-15b00e8335fc4f38aa06	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid n/a 13V, negative-QTOF	splash10-000i-8900000000-747475beaab808790b34	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid n/a 13V, negative-QTOF	splash10-0a4i-9000000000-3f979a5a82ec557199d2	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid n/a 13V, negative-QTOF	splash10-000i-9200000000-6cf6b1cdb1b4daf8e75e	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid n/a 13V, negative-QTOF	splash10-001i-9000000000-d6d7beafc7ee2bb2a192	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid n/a 13V, negative-QTOF	splash10-01ox-7900000000-68aea84a1f89134ebc22	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid n/a 13V, negative-QTOF	splash10-001l-9000000000-d9f7d56a5b6bd6463464	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid Orbitrap 3V, negative-QTOF	splash10-00di-0900000000-fed70c7dae6c6f23bae9	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Quinic acid Orbitrap 4V, negative-QTOF	splash10-00di-1900000000-e16e362b004ea0384f15	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinic acid 10V, Positive-QTOF	splash10-002g-0900000000-6090e29697cceb8ed703	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinic acid 20V, Positive-QTOF	splash10-004j-0900000000-ff720a1f9f0dbc98acff	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinic acid 40V, Positive-QTOF	splash10-004i-5900000000-5c1c1803314d0b1f64e1	2015-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinic acid 10V, Negative-QTOF	splash10-0007-0900000000-6b41698b204f0ce3d11f	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinic acid 20V, Negative-QTOF	splash10-0002-3900000000-23b1cc2c351b0b724523	2015-09-15	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Quinic acid 40V, Negative-QTOF	splash10-05i1-9700000000-00093da94309c2fb169a	2015-09-15	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2020-03-04	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Placenta
Spleen

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	24740205	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24801555	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25762808	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Feces	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	20669995	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.5 (0.0-1.0) uM	Adult (>18 years old)	Both	Prostate Cancer	19212411	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal adenoma	27510537	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Bladder cancer	28157703	details

Associated Disorders and Diseases

Disease References

Prostate cancer
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Colorectal cancer
Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ] Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]

Associated OMIM IDs

176807 (Prostate cancer)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Quinic_acid

METLIN ID

Not Available

PubChem Compound

6508

PDB ID

Not Available

ChEBI ID

17521

Food Biomarker Ontology

Not Available

VMH ID

QUINT

MarkerDB ID

Not Available

Good Scents ID

rw1049921

References

Synthesis Reference

Nagai, Naoshi; Kuboyama, Hisaharu; Enya, Masahiro. Method for preparation of quinic acid and its esters. Jpn. Kokai Tokkyo Koho (2000), 7 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Wittemer SM, Ploch M, Windeck T, Muller SC, Drewelow B, Derendorf H, Veit M: Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans. Phytomedicine. 2005 Jan;12(1-2):28-38. [PubMed:15693705 ]
Akesson C, Lindgren H, Pero RW, Leanderson T, Ivars F: Quinic acid is a biologically active component of the Uncaria tomentosa extract C-Med 100. Int Immunopharmacol. 2005 Jan;5(1):219-29. [PubMed:15589483 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Quinic acid (HMDB0003072)

MOL for HMDB0003072 (Quinic acid)

3D MOL for HMDB0003072 (Quinic acid)

3D SDF for HMDB0003072 (Quinic acid)

3D-SDF for HMDB0003072 (Quinic acid)

PDB for HMDB0003072 (Quinic acid)

3D PDB for HMDB0003072 (Quinic acid)

SMILES for HMDB0003072 (Quinic acid)

INCHI for HMDB0003072 (Quinic acid)

Structure for HMDB0003072 (Quinic acid)

3D Structure for HMDB0003072 (Quinic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra