Tributyl citrate

Details

• Internal ID: 3edefdb4-ebab-468c-8c34-b9db390a6081
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives
• IUPAC Name: tributyl 2-hydroxypropane-1,2,3-tricarboxylate
• SMILES (Canonical): CCCCOC(=O)CC(CC(=O)OCCCC)(C(=O)OCCCC)O
• SMILES (Isomeric): CCCCOC(=O)CC(CC(=O)OCCCC)(C(=O)OCCCC)O
• InChI: InChI=1S/C18H32O7/c1-4-7-10-23-15(19)13-18(22,17(21)25-12-9-6-3)14-16(20)24-11-8-5-2/h22H,4-14H2,1-3H3
• InChI Key: ZFOZVQLOBQUTQQ-UHFFFAOYSA-N
• Popularity: 200 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₃₂O₇
• Molecular Weight: 360.40 g/mol
• Exact Mass: 360.21480336 g/mol
• Topological Polar Surface Area (TPSA): 99.10 Ų
• XlogP: 2.70
• Atomic LogP (AlogP): 2.53
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 14

Synonyms

• 77-94-1
• Tri-n-butyl citrate
• tributyl 2-hydroxypropane-1,2,3-tricarboxylate
• Butyl citrate
• Citroflex 4
• Citric acid, tributyl ester
• n-Butyl citrate
• 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, tributyl ester
• Morflex tbc
• Citroflex c 4
• NSC 8491
• NSC-8491
• 2-Hydroxy-1,2,3-propanetricarboxylic acid, tributyl ester
• 827D5B1B6S
• 1,2,3-Propanetricarboxylic acid, 2-hydroxy-, 1,2,3-tributyl ester
• Butyl citrate (VAN)
• Citric Acid Tributyl Ester
• C18H32O7
• EINECS 201-071-2
• BRN 1806072
• UNII-827D5B1B6S
• AI3-00394
• ?Tributyl citrate
• Tributyl 2-hydroxy-1,2,3-propanetricarboxylate
• Tributyl citrate [NF]
• EC 201-071-2
• Tributyl2-hydroxypropane-1,2,3-tricarboxylate
• BUTYL CITRATE [MI]
• SCHEMBL24668
• Citric acid tri-n-butyl ester
• Tributyl citrate, >=97.0%
• TRIBUTYL CITRATE [INCI]
• CHEMBL2107619
• DTXSID5051442
• NSC8491
• TRIBUTYL CITRATE [MART.]
• CHEBI:176825
• TRIBUTYL CITRATE [USP-RS]
• MFCD00027217
• AKOS015839595
• TRIBUTYL CITRATE [EP IMPURITY]
• CS-W014478
• DS-4667
• HY-W013762
• C0366
• FT-0631337
• A839297
• Tributyl 2-hydroxy-1,2,3-propanetricarboxylate #
• Q1954892
• W-104292
• TRIBUTYL ACETYLCITRATE IMPURITY A [EP IMPURITY]
• 2-Hydroxy-1,3-propanetricarboxylic acid, tributyl ester
• 1,3-Propanetricarboxylic acid, 2-hydroxy-, tributyl ester
• Tributyl 2-Hydroxypropane-1,2,3-tricarboxylate (Tributyl Citrate)
• Tributyl citrate, United States Pharmacopeia (USP) Reference Standard
• Tributyl citrate, Pharmaceutical Secondary Standard; Certified Reference Material
• InChI=1/C18H32O7/c1-4-7-10-23-15(19)13-18(22,17(21)25-12-9-6-3)14-16(20)24-11-8-5-2/h22H,4-14H2,1-3H
• Tributyl Acetylcitrate Imp. A (EP); Tributyl 2-Hydroxypropane-1,2,3-tricarboxylate; Tributyl Citrate; Tributyl Acetylcitrate Impurity A

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9152	91.52%
Caco-2	+	0.7523	75.23%
Blood Brain Barrier	+	0.7500	75.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8588	85.88%
OATP2B1 inhibitior	-	0.8538	85.38%
OATP1B1 inhibitior	+	0.8712	87.12%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.4603	46.03%
P-glycoprotein inhibitior	-	0.6699	66.99%
P-glycoprotein substrate	-	0.9278	92.78%
CYP3A4 substrate	-	0.5218	52.18%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8698	86.98%
CYP3A4 inhibition	-	0.8610	86.10%
CYP2C9 inhibition	-	0.8468	84.68%
CYP2C19 inhibition	-	0.8234	82.34%
CYP2D6 inhibition	-	0.9373	93.73%
CYP1A2 inhibition	-	0.8769	87.69%
CYP2C8 inhibition	-	0.7830	78.30%
CYP inhibitory promiscuity	-	0.9434	94.34%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.7300	73.00%
Carcinogenicity (trinary)	Non-required	0.6384	63.84%
Eye corrosion	-	0.7394	73.94%
Eye irritation	+	0.7981	79.81%
Skin irritation	-	0.7735	77.35%
Skin corrosion	-	0.9724	97.24%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4884	48.84%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.8262	82.62%
Respiratory toxicity	-	0.9000	90.00%
Reproductive toxicity	-	0.8222	82.22%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	+	0.7369	73.69%
Acute Oral Toxicity (c)	IV	0.4870	48.70%
Estrogen receptor binding	-	0.7851	78.51%
Androgen receptor binding	-	0.6349	63.49%
Thyroid receptor binding	+	0.7579	75.79%
Glucocorticoid receptor binding	-	0.5432	54.32%
Aromatase binding	-	0.5119	51.19%
PPAR gamma	-	0.7613	76.13%
Honey bee toxicity	-	0.9845	98.45%
Biodegradation	+	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8496	84.96%

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	95.10%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.00%	99.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.01%	97.25%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	88.57%	80.78%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	87.82%	97.29%
CHEMBL2581	P07339	Cathepsin D	86.93%	98.95%
CHEMBL2996	Q05655	Protein kinase C delta	82.37%	97.79%
CHEMBL230	P35354	Cyclooxygenase-2	81.93%	89.63%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.19%	86.33%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	80.19%	80.33%

Plants that contains it

• Calophyllum inophyllum
• Lonicera caerulea
• Seriphidium baldshuanicum

Cross-Links

• PubChem: 6507
• LOTUS: LTS0271574
• wikiData: Q1954892