(1R,2R)-1-hydroxypropane-1,2,3-tricarboxylic acid

Details

• Internal ID: 3227e5ab-bbcc-4fe8-9dca-11038ebeb0fe
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: (1R,2R)-1-hydroxypropane-1,2,3-tricarboxylic acid
• SMILES (Canonical): C(C(C(C(=O)O)O)C(=O)O)C(=O)O
• SMILES (Isomeric): C([C@H]([C@H](C(=O)O)O)C(=O)O)C(=O)O
• InChI: InChI=1S/C6H8O7/c7-3(8)1-2(5(10)11)4(9)6(12)13/h2,4,9H,1H2,(H,7,8)(H,10,11)(H,12,13)/t2-,4-/m1/s1
• InChI Key: ODBLHEXUDAPZAU-VVJJHMBFSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆H₈O₇
• Molecular Weight: 192.12 g/mol
• Exact Mass: 192.02700259 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -1.39
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 5

Synonyms

• (1R,2R)-Isocitric acid
• (1R,2R)-1-hydroxypropane-1,2,3-tricarboxylic acid
• 1187-17-3
• (-)-erythro-form
• L-Alloisocitric acid
• (-)-Alloisocitric acid
• CHEBI:43291
• 3-carboxy-3,4-dideoxy-D-erythro-pentaric acid
• Q27104505

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7424	74.24%
Caco-2	-	0.9846	98.46%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6836	68.36%
OATP2B1 inhibitior	-	0.8523	85.23%
OATP1B1 inhibitior	+	0.9576	95.76%
OATP1B3 inhibitior	+	0.9515	95.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9902	99.02%
P-glycoprotein inhibitior	-	0.9855	98.55%
P-glycoprotein substrate	-	0.9872	98.72%
CYP3A4 substrate	-	0.7419	74.19%
CYP2C9 substrate	+	0.6015	60.15%
CYP2D6 substrate	-	0.8368	83.68%
CYP3A4 inhibition	-	0.8948	89.48%
CYP2C9 inhibition	-	0.9610	96.10%
CYP2C19 inhibition	-	0.9639	96.39%
CYP2D6 inhibition	-	0.9488	94.88%
CYP1A2 inhibition	-	0.9467	94.67%
CYP2C8 inhibition	-	0.9865	98.65%
CYP inhibitory promiscuity	-	0.9910	99.10%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8230	82.30%
Carcinogenicity (trinary)	Non-required	0.7434	74.34%
Eye corrosion	-	0.8721	87.21%
Eye irritation	+	0.8123	81.23%
Skin irritation	+	0.5094	50.94%
Skin corrosion	-	0.8592	85.92%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8032	80.32%
Micronuclear	-	0.5000	50.00%
Hepatotoxicity	+	0.6425	64.25%
skin sensitisation	-	0.9352	93.52%
Respiratory toxicity	-	0.8889	88.89%
Reproductive toxicity	-	0.8667	86.67%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.6619	66.19%
Acute Oral Toxicity (c)	III	0.7630	76.30%
Estrogen receptor binding	-	0.8677	86.77%
Androgen receptor binding	-	0.7432	74.32%
Thyroid receptor binding	-	0.8538	85.38%
Glucocorticoid receptor binding	-	0.6046	60.46%
Aromatase binding	-	0.8577	85.77%
PPAR gamma	-	0.8323	83.23%
Honey bee toxicity	-	0.9154	91.54%
Biodegradation	+	0.6500	65.00%
Crustacea aquatic toxicity	-	0.9400	94.00%
Fish aquatic toxicity	-	0.7744	77.44%

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	92.76%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.34%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.85%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	86.03%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.35%	99.17%

Plants that contains it

• Alstonia muelleriana
• Angelica decursiva
• Aquilaria sinensis
• Coreopsis nodosa
• Couroupita guianensis
• Dacrydium cupressinum
• Digitalis purpurea
• Glycine tomentella
• Kalanchoe fedtschenkoi
• Nicotiana undulata
• Panax ginseng
• Passiflora incarnata
• Senecio paludaffinis
• Seriphidium cinum
• Trigonella grandiflora
• Tripolium pannonicum
• Uvaria calamistrata

Cross-Links

• PubChem: 439238
• NPASS: NPC67132
• LOTUS: LTS0029029
• wikiData: Q27104505