(+)-Quinic acid

Details

• Internal ID: cc789934-91ed-49b1-9b0f-cf76b03d63e1
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Alcohols and polyols > Cyclitols and derivatives > Quinic acids and derivatives
• IUPAC Name: (3S,5S)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
• SMILES (Canonical): C1C(C(C(CC1(C(=O)O)O)O)O)O
• SMILES (Isomeric): C1[C@@H](C([C@H](CC1(C(=O)O)O)O)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?/m0/s1
• InChI Key: AAWZDTNXLSGCEK-ZHQZDSKASA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇H₁₂O₆
• Molecular Weight: 192.17 g/mol
• Exact Mass: 192.06338810 g/mol
• Topological Polar Surface Area (TPSA): 118.00 Ų
• XlogP: -2.40
• Atomic LogP (AlogP): -2.32
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 1

Synonyms

• 36413-60-2
• (3S,5S)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid
• CHEBI:36124
• NSC 1115
• EINECS 253-023-5
• AI3-63020
• 1D-1(OH),3,4/5-tetrahydroxycyclohexanecarboxylic acid
• (1R,3S,4R,5S)-1,3,4,5-tetrahydroxycyclohexanecarboxylic acid
• 1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid (1alpha,3alpha,4alpha,5beta)-
• Prestwick3_001103
• BSPBio_001206
• MLS002154154
• BPBio1_001328
• CHEMBL444501
• AAWZDTNXLSGCEK-DRMQKGJZSA-N
• Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1.alpha.,3.alpha.,4.alpha.,5.beta.)-
• Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1.alpha.,3R,4.alpha.,5R)-rel-
• DTXSID701337780
• HMS2098M08
• HMS2235F23
• NCGC00142589-01
• SMR001233454
• AB00514049
• SR-01000838829
• SR-01000838829-2
• Q27116711
• rel-(1|A,3R,4|A,5R)-1,3,4,5-Tetrahydroxycyclohexanecarboxylic acid
• Cyclohexanecarboxylic acid, 1,3,4,5-tetrahydroxy-, (1alpha,3alpha,4alpha,5beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6293	62.93%
Caco-2	-	0.9566	95.66%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8107	81.07%
OATP2B1 inhibitior	-	0.8476	84.76%
OATP1B1 inhibitior	+	0.9838	98.38%
OATP1B3 inhibitior	+	0.9544	95.44%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9730	97.30%
P-glycoprotein inhibitior	-	0.9886	98.86%
P-glycoprotein substrate	-	0.9685	96.85%
CYP3A4 substrate	-	0.6473	64.73%
CYP2C9 substrate	+	0.5995	59.95%
CYP2D6 substrate	-	0.8495	84.95%
CYP3A4 inhibition	-	0.9509	95.09%
CYP2C9 inhibition	-	0.9665	96.65%
CYP2C19 inhibition	-	0.9593	95.93%
CYP2D6 inhibition	-	0.9623	96.23%
CYP1A2 inhibition	-	0.9757	97.57%
CYP2C8 inhibition	-	0.9933	99.33%
CYP inhibitory promiscuity	-	0.9958	99.58%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6890	68.90%
Eye corrosion	-	0.9783	97.83%
Eye irritation	-	0.5567	55.67%
Skin irritation	+	0.5273	52.73%
Skin corrosion	-	0.8540	85.40%
Ames mutagenesis	-	0.9400	94.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7736	77.36%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5073	50.73%
skin sensitisation	-	0.7081	70.81%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.5111	51.11%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	+	0.4762	47.62%
Acute Oral Toxicity (c)	III	0.7314	73.14%
Estrogen receptor binding	-	0.8123	81.23%
Androgen receptor binding	-	0.8173	81.73%
Thyroid receptor binding	-	0.7532	75.32%
Glucocorticoid receptor binding	-	0.7287	72.87%
Aromatase binding	-	0.8576	85.76%
PPAR gamma	-	0.8523	85.23%
Honey bee toxicity	-	0.9163	91.63%
Biodegradation	+	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	-	0.4696	46.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.38%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	86.89%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	83.36%	91.19%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.41%	96.38%
CHEMBL221	P23219	Cyclooxygenase-1	82.38%	90.17%

Plants that contains it

• Angelica acutiloba
• Angelica gigas
• Angelica sinensis
• Artemisia annua
• Artemisia carvifolia
• Cichorium intybus
• Cichorium pumilum
• Citrus × aurantium
• Euphorbia hirta
• Ginkgo biloba
• Hippophae rhamnoides
• Hypericum perforatum
• Pogostemon cablin
• Pyrrosia hastata
• Pyrrosia lingua
• Pyrrosia petiolosa
• Rubia argyi
• Sarcandra glabra
• Saussurea involucrata
• Staphylea arguta
• Uncaria macrophylla
• Uncaria rhynchophylla
• Uncaria sinensis
• Ziziphus jujuba

Cross-Links

• PubChem: 37439
• NPASS: NPC47993