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Quinic acid
- Family: Plantae - Myrtaceae
- Kingdom: Plantae
- Class: Cyclohexanecarboxylic Acid
| Canonical Smiles | OC1[C@H](O)CC(C[C@H]1O)(O)C(=O)O |
|---|---|
| InChI | 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 |
| InChIKey | AAWZDTNXLSGCEK-LNVDRNJUSA-N |
| Formula | C7H12O6 |
| HBA | 5 |
| HBD | 5 |
| MW | 192.17 |
| Rotatable Bonds | 1 |
| TPSA | 118.22 |
| LogP | -2.32 |
| Number Rings | 1 |
| Number Aromatic Rings | 0 |
| Heavy Atom Count | 13 |
| Formal Charge | 0 |
| Fraction CSP3 | 0.86 |
| Exact Mass | 192.06 |
| Number of Lipinski Rule Violations | 0 |
| # | Species | Family | Kingdom | NCBI Taxonomy ID |
|---|---|---|---|---|
| 1 | Withania somnifera | Solanaceae | Plantae | 126910 |
| 2 | Erigeron floribundus | Asteraceae | Plantae | 91244 |
| 3 | Convolvulus althaeoides | Convolvulaceae | Plantae | 267570 |
| 4 | Cyperus alternifolius | Cyperaceae | Plantae | 4611 |
| 5 | Rosmarinuseriocalyx | Lamiaceae | Plantae | — |
| 6 | Syzygium cumini | Myrtaceae | Plantae | — |
Showing of synonyms
Quinic acid
Quinate
(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
CHEBI:26490
7729-33-1
77-95-2
D-(-)-Quinic acid
(-)-quinic acid
Chinic acid
Kinic acid
Chinasaure
D-QUINIC ACID
D(-)-Quinic acid
L-Quinic acid
L-Quinate
MFCD00003864
(3r,5r)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
(3R,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
Rel-Quinic Acid
CHEBI:17521
NSC1115
SpecPlus_000419
NSC59258
(1S,3R,4S,5R)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
(-)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid
DivK1c_006515
058C04BGYI
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (-)-
NSC-59258
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1R-(1-alpha,3-alpha,4-alpha,5-beta))-
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1R-(1alpha,3alpha,4alpha,5beta))-
SDCCGMLS-0066613.P001
1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid (1R-(1alpha,3alpha,4alpha,5beta)
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1theta-(1alpha,3alpha,4alpha,5beta))-
1L-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylic acid
Quinicacid
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1alpha,3R,4alpha,5R)-
D-(-)-Kinic Acid
D-(-)-Chinic Acid
EINECS 201-072-8
NSC 59258
UNII-058C04BGYI
Chinate
Kinate
1L-1(OH),3,4/5-Tetrahydroxycyclohexanecarboxylate
4gui
4iuo
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1.alpha.,3R,4.alpha.,5R)-
(-)Quinic acid
QIC
D-(-)-Quinic-acid
Spectrum_001413
Spectrum2_001790
Spectrum3_001349
Spectrum4_001867
Spectrum5_000434
QUINIC ACID [MI]
Bmse000306
SCHEMBL39556
BSPBio_003137
KBioGR_002336
KBioSS_001893
SPECTRUM310018
MLS002207201
QUINIC ACID [USP-RS]
QUINIC ACID [WHO-DD]
SPBio_001719
CHEMBL465398
MEGxp0_001735
SCHEMBL1286207
SCHEMBL7923331
D-(-)-Quinic acid, 98%
ACon1_001963
D-(-)-Quinic acid (Standard)
HY-N0464R
KBio1_001459
KBio2_001893
KBio2_004461
KBio2_007029
KBio3_002357
DTXSID70998288
HMS3885A12
HY-N0464
MSK40055
NSC-1115
BBL033519
BDBM50485632
CCG-38438
S3886
STK801928
(-) Quinic acid, analytical standard
AKOS005622501
FQ15911
NCGC00178246-01
NCGC00178246-02
1ST40055
BP-12304
DA-62619
PD087258
SMR001306762
VS-12119
CS-0008991
Q0009
C00296
D-(-)-Quinic acid, purum, >=98.0% (T)
EN300-197153
H10089
Q424931
883DE888-EC82-454C-B69C-8B1F9AC6DAA9
Z1255382952
(1R,3R,4R,5R)-(-)-Tetrahydroxycyclohexanecarboxylic acid
(3R,5R)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylicacid
(1|A,3R,4|A,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid
(3R,5R)-1,3,4,5-tetrakis(oxidanyl)cyclohexane-1-carboxylic acid
Quinic acid, United States Pharmacopeia (USP) Reference Standard
(-)-QUINIC ACID (CONSTITUENT OF CRANBERRY LIQUID PREPARATION) [DSC]
(1alpha,3R,4alpha,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid
Quinic Acid, Pharmaceutical Secondary Standard
Certified Reference Material
Cyclohexanecarboxylic acid,3,4,5-tetrahydroxy-, (1.alpha.,3.alpha.,4.alpha.,5.beta.)-
Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1.alpha., 3.alpha.,4.alpha.,5.beta.)-
- Farrag A.R.H, Abdallah H.M.I, et al. (2019). Antiulcer activity of Cyperus alternifolius in relation to its UPLC-MS metabolite fingerprint: A mechanistic study. Phytomedicine : international journal of phytotherapy and phytopharmacology, 2019, 62, 152970. [View] [PubMed]
- Eldin Elhawary S.S, Elmotyam A.K.E, et al. (2022). Cytotoxic and anti-diabetic potential, metabolic profiling and insilico studies of Syzygium cumini (L.) Skeels belonging to family Myrtaceae. Natural product research,2022, 36(4), 1026-1030. [View] [PubMed]
- Hrichi S, Chaabane-Banaoues R, et al. (2020). Effect of seasonal variation on the chemical composition and antioxidant and antifungal activities of Convolvulus althaeoides L. leaf extract. Arabian Journal of Chemistry, 2020, 13(6), 5651-5668. [View]
- Kandil F, El Sayed N, et al. (1994). Flavonol Glycosides And Phenolics From Withania Somnifera. Phytochemistry, 1994, 37(4), 1215-1216. [View]
- Berto C, Maggi F, et al. (2014). Phenolic constituents of Erigeron floribundus (Asteraceae), a Cameroonian medicinal plant.. Natural Product Communications, 2014, 9(12), 1691-1964. [View] [PubMed]
- Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]
CPRiL:
60676
SMILES: C1CCCCC1
Level: 0
Mol. Weight: 192.17 g/mol
No bioactivities available.
Absorption
- Caco-2 (logPapp)
- -5.38
- Human Oral Bioavailability 20%
- Bioavailable
- Human Intestinal Absorption
- Absorbed
- Madin-Darby Canine Kidney
- -3.76
- Human Oral Bioavailability 50%
- Non-Bioavailable
- P-Glycoprotein Inhibitor
- Non-Inhibitor
- P-Glycoprotein Substrate
- Non-Substrate
- Skin Permeability
- -1.59
Distribution
- Blood-Brain Barrier (CNS)
- -
- Blood-Brain Barrier
- Non-Penetrable
- Fraction Unbound (Human)
- 0.41
- Plasma Protein Binding
- 36.16
- Steady State Volume of Distribution
- -
Metabolism
- Breast Cancer Resistance Protein
- Non-Inhibitor
- CYP 1A2 Inhibitor
- Non-Inhibitor
- CYP 1A2 Substrate
- Non-Substrate
- CYP 2C19 Inhibitor
- Non-Inhibitor
- CYP 2C19 Substrate
- Non-Substrate
- CYP 2C9 Inhibitor
- Non-Inhibitor
- CYP 2C9 Substrate
- Non-Substrate
- CYP 2D6 Inhibitor
- Non-Inhibitor
- CYP 2D6 Substrate
- Non-Substrate
- CYP 3A4 Inhibitor
- Non-Inhibitor
- CYP 3A4 Substrate
- Non-Substrate
- OATP1B1
- Non-Inhibitor
- OATP1B3
- Non-Inhibitor
Excretion
- Clearance
- 1.12
- Organic Cation Transporter 2
- Non-Inhibitor
- Half-Life of Drug
- -
Toxicity
- AMES Mutagenesis
- Safe
- Avian
- Safe
- Bee
- Toxic
- Bioconcentration Factor
- -1.3
- Biodegradation
- Toxic
- Carcinogenesis
- Safe
- Crustacean
- Safe
- Liver Injury I (DILI)
- Safe
- Eye Corrosion
- Safe
- Eye Irritation
- Safe
- Maximum Tolerated Dose
- 2.25
- Liver Injury II
- Safe
- hERG Blockers
- Safe
- Daphnia Maga
- 2.61
- Micronucleos
- Safe
- NR-AhR
- Safe
- NR-AR
- Safe
- NR-AR-LBD
- Safe
- NR-Aromatase
- Safe
- NR-ER
- Safe
- NR-ER-LBD
- Safe
- NR-GR
- Safe
- NR-PPAR-gamma
- Safe
- NR-TR
- Safe
- T. Pyriformis
- -3.98
- Rat (Acute)
- 0.89
- Rat (Chronic Oral)
- 2.96
- Fathead Minnow
- 2.05
- Respiratory Disease
- Safe
- Skin Sensitisation
- Toxic
- SR-ARE
- Safe
- SR-ATAD5
- Safe
- SR-HSE
- Safe
- SR-MMP
- Safe
- SR-p53
- Safe
General Properties
- Boiling Point
- 410.21
- Hydration Free Energy
- -20.77
- Log(D) at pH=7.4
- -3.67
- Log(P)
- -2.81
- Log S
- -0.25
- Log(Vapor Pressure)
- -11.74
- Melting Point
- 161.34
- pKa Acid
- 3.7
- pKa Basic
- 6.73
| Protein Name | UniProt ID | Entry Name | Species | #Pharmacophore Points | Probability (0.7 ≤ Tversky Score ≤ 1.0) |
|---|---|---|---|---|---|
| Thermolysin | P00800 | THER_BACTH | Bacillus thermoproteolyticus | 3 | 0.8536 |
| Shikimate kinase | P9WPY3 | AROK_MYCTU | Mycobacterium tuberculosis | 3 | 0.8276 |
| Shikimate dehydrogenase (NADP(+)) | P56119 | AROE_HELPY | Helicobacter pylori | 3 | 0.8240 |
| 3-dehydroquinate dehydratase | P9WPX7 | AROQ_MYCTU | Mycobacterium tuberculosis | 3 | 0.8218 |
| Beta-glucosidase A | Q08638 | BGLA_THEMA | Thermotoga maritima | 3 | 0.8129 |
| Trichothecene 15-O-acetyltransferase TRI3 | Q9C1B7 | TRI3_FUSSP | Fusarium sporotrichioides | 3 | 0.8080 |
| Lysozyme C II | P11941 | LYSC2_ONCMY | Oncorhynchus mykiss | 3 | 0.8037 |
| ADP-ribosylation factor 1 | P84077 | ARF1_HUMAN | Homo sapiens | 2 | 0.7766 |
| Branched-chain-amino-acid aminotransferase, mitochondrial | O15382 | BCAT2_HUMAN | Homo sapiens | 3 | 0.7684 |
| Aldos-2-ulose dehydratase | P84193 | AUD_PHACH | Phanerodontia chrysosporium | 3 | 0.7676 |
| 2-dehydro-3-deoxyphosphooctonate aldolase | P0A715 | KDSA_ECOLI | Escherichia coli | 3 | 0.7660 |
| Chorismate mutase AroH | P19080 | AROH_BACSU | Bacillus subtilis | 3 | 0.7286 |
| Beta-glucosidase | Q8T0W7 | Q8T0W7_9NEOP | Neotermes koshunensis | 3 | 0.7134 |
| Streptavidin | P22629 | SAV_STRAV | Streptomyces avidinii | 3 | 0.7082 |