(2R,3R)-2-Hydroxycitric acid

Details

• Internal ID: b2455f3d-9e7f-4ab2-9e88-7d14387dc088
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: (1R,2R)-1,2-dihydroxypropane-1,2,3-tricarboxylic acid
• SMILES (Canonical): C(C(=O)O)C(C(C(=O)O)O)(C(=O)O)O
• SMILES (Isomeric): C(C(=O)O)[C@@]([C@H](C(=O)O)O)(C(=O)O)O
• InChI: InChI=1S/C6H8O8/c7-2(8)1-6(14,5(12)13)3(9)4(10)11/h3,9,14H,1H2,(H,7,8)(H,10,11)(H,12,13)/t3-,6+/m0/s1
• InChI Key: ZMJBYMUCKBYSCP-BBIVZNJYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₈O₈
• Molecular Weight: 208.12 g/mol
• Exact Mass: 208.02191721 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -2.28
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• (2R,3R)-2-Hydroxycitric acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7075	70.75%
Caco-2	-	0.9785	97.85%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	+	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7275	72.75%
OATP2B1 inhibitior	-	0.8535	85.35%
OATP1B1 inhibitior	+	0.9435	94.35%
OATP1B3 inhibitior	+	0.9516	95.16%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9874	98.74%
P-glycoprotein inhibitior	-	0.9858	98.58%
P-glycoprotein substrate	-	0.9844	98.44%
CYP3A4 substrate	-	0.7169	71.69%
CYP2C9 substrate	+	0.5995	59.95%
CYP2D6 substrate	-	0.8495	84.95%
CYP3A4 inhibition	-	0.8735	87.35%
CYP2C9 inhibition	-	0.9399	93.99%
CYP2C19 inhibition	-	0.9396	93.96%
CYP2D6 inhibition	-	0.9476	94.76%
CYP1A2 inhibition	-	0.9336	93.36%
CYP2C8 inhibition	-	0.9869	98.69%
CYP inhibitory promiscuity	-	0.9904	99.04%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8030	80.30%
Carcinogenicity (trinary)	Non-required	0.7129	71.29%
Eye corrosion	-	0.9100	91.00%
Eye irritation	+	0.6481	64.81%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.8746	87.46%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8257	82.57%
Micronuclear	+	0.6300	63.00%
Hepatotoxicity	+	0.5250	52.50%
skin sensitisation	-	0.8686	86.86%
Respiratory toxicity	-	0.7333	73.33%
Reproductive toxicity	-	0.8222	82.22%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.8656	86.56%
Acute Oral Toxicity (c)	III	0.8407	84.07%
Estrogen receptor binding	-	0.8483	84.83%
Androgen receptor binding	-	0.7016	70.16%
Thyroid receptor binding	-	0.7771	77.71%
Glucocorticoid receptor binding	-	0.5204	52.04%
Aromatase binding	-	0.7660	76.60%
PPAR gamma	-	0.7074	70.74%
Honey bee toxicity	-	0.9442	94.42%
Biodegradation	+	0.8250	82.50%
Crustacea aquatic toxicity	-	0.8900	89.00%
Fish aquatic toxicity	-	0.7856	78.56%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	92.67%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.82%	96.09%
CHEMBL2581	P07339	Cathepsin D	89.89%	98.95%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.19%	99.17%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	81.38%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.09%	85.14%

Plants that contains it

• Cistanche salsa
• Garcinia oblongifolia
• Marrubium velutinum
• Piper wightii
• Trifolium resupinatum

Cross-Links

• PubChem: 13037289
• NPASS: NPC105881
• LOTUS: LTS0218033
• wikiData: Q105379477