Tributyl phosphate

Details

• Internal ID: cab8735e-5acf-4cd6-b221-4e2feef41d1a
• Taxonomy: Organic acids and derivatives > Organic phosphoric acids and derivatives > Phosphate esters > Alkyl phosphates > Trialkyl phosphates
• IUPAC Name: tributyl phosphate
• SMILES (Canonical): CCCCOP(=O)(OCCCC)OCCCC
• SMILES (Isomeric): CCCCOP(=O)(OCCCC)OCCCC
• InChI: InChI=1S/C12H27O4P/c1-4-7-10-14-17(13,15-11-8-5-2)16-12-9-6-3/h4-12H2,1-3H3
• InChI Key: STCOOQWBFONSKY-UHFFFAOYSA-N
• Popularity: 5,138 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₂H₂₇O₄P
• Molecular Weight: 266.31 g/mol
• Exact Mass: 266.16469634 g/mol
• Topological Polar Surface Area (TPSA): 44.80 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 4.54
• H-Bond Acceptor: 4
• H-Bond Donor: 0
• Rotatable Bonds: 12

Synonyms

• 126-73-8
• Tri-n-butyl phosphate
• Tributylphosphate
• Butyl phosphate
• Phosphoric acid tributyl ester
• Tributylphosphat
• Celluphos 4
• Disflamoll TB
• Phosphoric acid, tributyl ester
• tbpa
• Tributilfosfato
• Tributylfosfaat
• Tributyle (phosphate de)
• TBP
• Butyl phosphate, tri-
• Tributoxyphosphine oxide
• Tri-N-butylphosphate
• Tributylfosfat
• Butyl phosphate, ((BuO)3PO)
• Tributylfosfat [Czech]
• Tributylfosfaat [Dutch]
• Phosphoric acid tri-n-butyl ester
• Tributilfosfato [Italian]
• Tributylphosphat [German]
• NSC 8484
• CCRIS 6106
• DTXSID3021986
• HSDB 1678
• Tributyle (phosphate de) [French]
• MCS 2495
• EINECS 204-800-2
• UNII-95UAS8YAF5
• BRN 1710584
• 95UAS8YAF5
• AI3-00399
• CHEBI:35019
• Tributyl ester of phosphoric acid
• TRI-N-BUTYL-D27 PHOSPHATE
• NSC-8484
• EC 204-800-2
• 4-01-00-01531 (Beilstein Handbook Reference)
• DTXCID701986
• CAS-126-73-8
• TNBP
• Tributylphsophate
• Kronitex TBP
• Phosphate de tributyle
• Tributyle(phosphate de)
• Phosphoric acid tributyl
• TBP (CHRIS Code)
• tris(1-butyl) phosphate
• Tributyl phosphate, 97%
• Tributyl phosphate, 99%
• bmse000777
• Syn-O-Ad 8412
• SCHEMBL18570
• Tributyl phosphate, >=99%
• BIDD:ER0345
• Tributyl phosphate, all isomers
• TRIBUTYL PHOSPHATE [MI]
• CHEMBL1371096
• NSC8484
• TRIBUTYL PHOSPHATE [HSDB]
• Phosphoric acid, tri-n-butyl ester
• Tox21_201872
• Tox21_300107
• LS-705
• MFCD00009436
• WLN: 4OPO & O4 & O4
• AKOS015995460
• TRI-N-BUTYL PHOSPHATE [MART.]
• Tributyl phosphate, analytical standard
• NCGC00091588-01
• NCGC00091588-02
• NCGC00091588-03
• NCGC00091588-04
• NCGC00254202-01
• NCGC00259421-01
• FT-0657452
• P0266
• TRI-N-BUTYL PHOSPHATE [EP MONOGRAPH]
• Tributyl phosphate 10 microg/mL in Cyclohexane
• Tributyl Phosphate 1000 microg/mL in Methanol
• Tributyl phosphate, puriss., >=99.0% (GC)
• Tributyl phosphate, SAJ first grade, >=99.0%
• Tributyl phosphate, Selectophore(TM), >=98.0%
• A805594
• Q613394
• J-005429
• F1905-7225
• Tributyl phosphate, 10 mug/mL in hexane, analytical standard
• Tri-n-butyl phosphate, European Pharmacopoeia (EP) Reference Standard
• Tributyl phosphate, Pharmaceutical Secondary Standard; Certified Reference Material
• InChI=1/C12H27O4P/c1-4-7-10-14-17(13,15-11-8-5-2)16-12-9-6-3/h4-12H2,1-3H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9538	95.38%
Caco-2	+	0.8561	85.61%
Blood Brain Barrier	+	0.8750	87.50%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6359	63.59%
OATP2B1 inhibitior	-	0.8516	85.16%
OATP1B1 inhibitior	+	0.9506	95.06%
OATP1B3 inhibitior	+	0.9462	94.62%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.8303	83.03%
P-glycoprotein inhibitior	-	0.9269	92.69%
P-glycoprotein substrate	-	0.9617	96.17%
CYP3A4 substrate	-	0.6082	60.82%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7353	73.53%
CYP3A4 inhibition	-	0.8952	89.52%
CYP2C9 inhibition	-	0.8767	87.67%
CYP2C19 inhibition	-	0.8655	86.55%
CYP2D6 inhibition	-	0.9352	93.52%
CYP1A2 inhibition	-	0.8922	89.22%
CYP2C8 inhibition	-	0.9706	97.06%
CYP inhibitory promiscuity	-	0.9058	90.58%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.5800	58.00%
Carcinogenicity (trinary)	Non-required	0.4754	47.54%
Eye corrosion	+	0.9693	96.93%
Eye irritation	+	0.9818	98.18%
Skin irritation	-	0.5586	55.86%
Skin corrosion	-	0.8904	89.04%
Ames mutagenesis	-	0.9700	97.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6952	69.52%
Micronuclear	-	0.6300	63.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.9343	93.43%
Respiratory toxicity	-	0.9667	96.67%
Reproductive toxicity	-	0.7333	73.33%
Mitochondrial toxicity	-	0.9875	98.75%
Nephrotoxicity	+	0.8071	80.71%
Acute Oral Toxicity (c)	III	0.8339	83.39%
Estrogen receptor binding	-	0.8039	80.39%
Androgen receptor binding	-	0.8290	82.90%
Thyroid receptor binding	-	0.6208	62.08%
Glucocorticoid receptor binding	-	0.9058	90.58%
Aromatase binding	-	0.8405	84.05%
PPAR gamma	-	0.7486	74.86%
Honey bee toxicity	-	0.6839	68.39%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5152	51.52%
Fish aquatic toxicity	+	0.8802	88.02%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL340	P08684	Cytochrome P450 3A4	15848.9 nM; 15848.9 nM	Potency; Potency	via CMAUP; via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	93.37%	97.29%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.55%	97.25%
CHEMBL1907	P15144	Aminopeptidase N	92.36%	93.31%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.15%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.48%	98.95%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	87.34%	85.94%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.23%	99.17%
CHEMBL3230	O95977	Sphingosine 1-phosphate receptor Edg-6	86.78%	94.01%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	85.34%	92.86%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	84.28%	80.78%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.10%	96.95%
CHEMBL255	P29275	Adenosine A2b receptor	82.07%	98.59%

Plants that contains it

• Isodon henryi

Cross-Links

• PubChem: 31357
• NPASS: NPC120097
• ChEMBL: CHEMBL1371096