Trimethyl citrate

Details

• Internal ID: e461b2d2-469f-4543-83d1-ad6989416e8f
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: trimethyl 2-hydroxypropane-1,2,3-tricarboxylate
• SMILES (Canonical): COC(=O)CC(CC(=O)OC)(C(=O)OC)O
• SMILES (Isomeric): COC(=O)CC(CC(=O)OC)(C(=O)OC)O
• InChI: InChI=1S/C9H14O7/c1-14-6(10)4-9(13,8(12)16-3)5-7(11)15-2/h13H,4-5H2,1-3H3
• InChI Key: HDDLVZWGOPWKFW-UHFFFAOYSA-N
• Popularity: 53 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₄O₇
• Molecular Weight: 234.20 g/mol
• Exact Mass: 234.07395278 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: -1.00
• Atomic LogP (AlogP): -0.98
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 5

Synonyms

• 1587-20-8
• trimethyl 2-hydroxypropane-1,2,3-tricarboxylate
• Citric acid, trimethyl ester
• 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, trimethyl ester
• Citric Acid Trimethyl Ester
• UNII-2P8176332L
• EINECS 216-449-2
• MFCD00025889
• NSC 75824
• NSC-75824
• 1,2,3-trimethyl 2-hydroxypropane-1,2,3-tricarboxylate
• 2P8176332L
• 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, 1,2,3-trimethyl ester
• 3-Hydroxy-3-methoxycarbonylpentanedioic acid, dimethyl ester
• TRIMETHYLCITRATE
• Citric acid trimethyl
• Trimethyl2-hydroxypropane-1,2,3-tricarboxylate
• NCIOpen2_004149
• SCHEMBL168730
• CHEMBL455514
• Trimethyl citrate, >=98.0%
• DTXSID2061804
• HDDLVZWGOPWKFW-UHFFFAOYSA-
• HDDLVZWGOPWKFW-UHFFFAOYSA-N
• NSC75824
• AKOS015901740
• CS-W014165
• AS-12383
• FT-0726449
• EN300-749076
• W11576
• J-009525
• Trimethyl 2-hydroxy-1,2,3-propanetricarboxylate #
• Q27255361
• 1,3-Propanetricarboxylic acid, 2-hydroxy-, trimethyl ester
• 3-hydroxy-3-methoxycarbonyl-pentanedioic acid dimethyl ester
• 1,2,3-Propanetricarboxylicacid, 2-hydroxy-, 1,2,3-trimethyl ester
• InChI=1/C9H14O7/c1-14-6(10)4-9(13,8(12)16-3)5-7(11)15-2/h13H,4-5H2,1-3H3

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9182	91.82%
Caco-2	+	0.8276	82.76%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7725	77.25%
OATP2B1 inhibitior	-	0.8504	85.04%
OATP1B1 inhibitior	+	0.9307	93.07%
OATP1B3 inhibitior	+	0.9406	94.06%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	-	0.9223	92.23%
P-glycoprotein inhibitior	-	0.9398	93.98%
P-glycoprotein substrate	-	0.9564	95.64%
CYP3A4 substrate	-	0.6294	62.94%
CYP2C9 substrate	-	0.8062	80.62%
CYP2D6 substrate	-	0.8424	84.24%
CYP3A4 inhibition	-	0.9399	93.99%
CYP2C9 inhibition	-	0.9478	94.78%
CYP2C19 inhibition	-	0.9363	93.63%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.9572	95.72%
CYP2C8 inhibition	-	0.9480	94.80%
CYP inhibitory promiscuity	-	0.9850	98.50%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.5915	59.15%
Carcinogenicity (trinary)	Non-required	0.7452	74.52%
Eye corrosion	+	0.5672	56.72%
Eye irritation	+	0.7584	75.84%
Skin irritation	-	0.6873	68.73%
Skin corrosion	-	0.9557	95.57%
Ames mutagenesis	-	0.8300	83.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5649	56.49%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.5440	54.40%
skin sensitisation	-	0.5948	59.48%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	-	0.8420	84.20%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	+	0.6151	61.51%
Acute Oral Toxicity (c)	III	0.7946	79.46%
Estrogen receptor binding	-	0.7495	74.95%
Androgen receptor binding	-	0.6541	65.41%
Thyroid receptor binding	-	0.6503	65.03%
Glucocorticoid receptor binding	-	0.6601	66.01%
Aromatase binding	-	0.7189	71.89%
PPAR gamma	-	0.7244	72.44%
Honey bee toxicity	-	0.9213	92.13%
Biodegradation	+	0.5750	57.50%
Crustacea aquatic toxicity	-	0.7250	72.50%
Fish aquatic toxicity	-	0.7554	75.54%

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	94.32%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.20%	85.14%
CHEMBL4040	P28482	MAP kinase ERK2	90.38%	83.82%
CHEMBL3401	O75469	Pregnane X receptor	84.34%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.87%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.87%	96.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.85%	94.33%

Plants that contains it

• Cratoxylum cochinchinense
• Dioscorea japonica
• Dioscorea oppositifolia
• Dioscorea polystachya
• Gastrodia elata
• Lonicera caerulea
• Prunus mume
• Tagetes erecta

Cross-Links

• PubChem: 74112
• NPASS: NPC68743
• LOTUS: LTS0099326
• wikiData: Q27255361