Thyroxine

Details

• Internal ID: 39a54420-a386-4361-956c-7baacc5f94e8
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Amino acids, peptides, and analogues > Alpha amino acids and derivatives > Phenylalanine and derivatives
• IUPAC Name: (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
• InChI: InChI=1S/C15H11I4NO4/c16-8-4-7(5-9(17)13(8)21)24-14-10(18)1-6(2-11(14)19)3-12(20)15(22)23/h1-2,4-5,12,21H,3,20H2,(H,22,23)/t12-/m0/s1
• InChI Key: XUIIKFGFIJCVMT-LBPRGKRZSA-N
• Popularity: 73,892 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₁I₄NO₄
• Molecular Weight: 776.87 g/mol
• Exact Mass: 776.6867 g/mol
• Topological Polar Surface Area (TPSA): 92.80 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 4.56
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• thyroxin
• L Thyroxin beta
• L Thyrox
• L Thyroxine Roche
• L Thyroxin Henning
• Levothyroxin Delalande
• RefChem:5946
• L-3,5,5'-tetraiodothyronine
• 2-amino-3-(4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)propanoic acid
• Tyrosine, O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-
• L-thyroxine
• levothyroxine
• 51-48-9
• Levothyroxin
• Tetraiodothyronine
• 3,3',5,5'-Tetraiodo-L-thyronine
• Thyratabs
• Thyreoideum
• Thyroxinal
• Thyrax
• Thyroxine iodine
• 3,5,3',5'-Tetraiodo-L-thyronine
• (-)-Thyroxine
• L-Thyroxin
• L-T4
• Thyroxine (l)
• O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-L-tyrosine
• DL-Thyroxin
• Thyroxine (VAN)
• Laevothyroxinum
• t4
• Levothyroxinum (acid)
• Laevothyroxinum (acid)
• 3,5,3',5'-Tetraiodothyronine
• Thryroxine, l-
• Thyroxine, L-
• L-3,5,3',5'-Tetraiodothyronine
• MFCD00002595
• Forthyron (TN)
• Levothyroxinum
• 3,3',5,5''-Tetraiodo-L-thyronine
• CCRIS 6739
• Henning
• HSDB 3108
• 3,5,3'5'-Tetraiodo-L-thyronine
• NSC 36397
• Prestwick_548
• L-Tyrosine, O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-
• 4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodo-L-phenylalanine
• CHEBI:18332
• Synthetic levothyroxine
• O-(4-Hydroxy-3,5-diidophenyl)-3,5-diiodo-L-tyrosine
• (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoic acid
• 3-(4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)alanine
• beta-((3,5-Diiodo-4-hydroxyphenoxy)-3,5-diiodophenyl)alanine
• 3-[4-(4-Hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]-L-alanine
• CHEMBL1624
• O-(4-Hydroxy-3,5-diiodophenyl)-3,5-diiodotyrosine
• Q51BO43MG4
• DTXSID8023214
• THX
• NSC-36397
• (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]propanoic acid
• NCGC00164336-01
• DTXCID603214
• Levothyroxine;T4
• (S)-2-amino-3-(4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)propanoic acid
• LT4
• SMR000059176
• T44
• Levothyroxine (BAN)
• EINECS 200-101-1
• Levothyroxine [INN:BAN]
• Synthroid (*Sodium salt*)
• BRN 2228515
• Thyroxine (100% pure T4 reference standard (free of T3))
• UNII-Q51BO43MG4
• SR-01000759430
• 2ceo
• CAS-51-48-9
• Spectrum_001076
• 1hk1
• 1hk2
• 1hk3
• 1hk4
• 1hk5
• 1y0x
• CPD000059176
• L-Thyroxine, free acid
• L-Thyroxine (Standard)
• SpecPlus_000871
• THYROXINE [MI]
• Prestwick0_000403
• Prestwick1_000403
• Prestwick2_000403
• Prestwick3_000403
• Spectrum2_000573
• Spectrum3_000611
• Spectrum4_000128
• Spectrum5_001500
• bmse000923
• Epitope ID:123889
• LEVOTHYROXINE [HSDB]
• BIDD:PXR0161
• Levothroid (*Sodium salt*)
• SCHEMBL23098
• BSPBio_000326
• BSPBio_002142
• KBioGR_000516
• KBioSS_001556
• LEVOTHYROXINE [VANDF]
• MLS000028647
• MLS002548901
• DivK1c_006967
• SPECTRUM1500774
• SPBio_000386
• SPBio_002265
• LEVOTHYROXINE [USP-RS]
• LEVOTHYROXINE [WHO-DD]
• BPBio1_000360
• GTPL2635
• orb1310221
• KBio1_001911
• KBio2_001556
• KBio2_004124
• KBio2_006692
• KBio3_001642
• HMS1569A08
• HMS1921I06
• HMS2090P18
• HMS2092K12
• HMS2096A08
• HMS2233J18
• HMS3259M11
• HMS3713A08
• L-Thyroxine, >=98% (HPLC)
• Pharmakon1600-01500774
• Tox21_112101
• Tox21_302156
• BDBM50301375
• CCG-38738
• HY-18341R
• NSC757434
• s2599
• AKOS015905129
• Tox21_112101_1
• AC-7504
• CS-1819
• DB00451
• FL34087
• NC00485
• NSC-757434
• SDCCGMLS-0066571.P001
• 2-amino-3-[4-(4-hydroxy-3,5-diiodo-phenoxy)-3,5-diiodo-phenyl]-propanoic acid
• 3,3'',5,5''-tetraiodo-L-thyronine
• 3,5,3'',5''-tetraiodo-L-thyronine
• SK&F 1-6528
• NCGC00094852-03
• NCGC00164336-02
• NCGC00164336-03
• NCGC00164336-04
• NCGC00164336-05
• NCGC00164336-06
• NCGC00255368-01
• AC-10465
• AS-81045
• HY-18341
• SY035142
• SBI-0051608.P002
• DB-006261
• NS00067050
• SW196731-3
• C01829
• D08125
• D78141
• EN300-708765
• AB00052176-08
• AB00052176_09
• AB00052176_10
• 002T595
• Q773449
• SR-05000001567
• LIOTHYRONINE SODIUM IMPURITY A [EP IMPURITY]
• SR-01000759430-2
• SR-05000001567-1
• BRD-K30685142-001-05-5
• BRD-K30685142-001-08-9
• BRD-K30685142-001-14-7
• BRD-K30685142-001-15-4
• BRD-K30685142-001-16-2
• BRD-K30685142-001-17-0
• Thyroxine (T4), IRMM(R) certified Reference Material
• L-Thyroxine, powder, BioReagent, suitable for cell culture
• L-Tyrosine,O-(4-hydroxy-3,5-diiodophenyl)-3,5-diiodo-
• Levothyroxine, United States Pharmacopeia (USP) Reference Standard
• (-)-3-(4-(4-HYDROXY-3,5-DIIODOPHENOXY)-3,5-DIIODOPHENYL)ALANINE
• (2S)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3, 5-diiodophenyl]propanoic acid
• (S)-2-amino-3-(4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl)propanoicacid
• Levothyroxine, Pharmaceutical Secondary Standard; Certified Reference Material

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9674	96.74%
Caco-2	-	0.7889	78.89%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	+	0.5571	55.71%
Subcellular localzation	Mitochondria	0.6085	60.85%
OATP2B1 inhibitior	+	1.0000	100.00%
OATP1B1 inhibitior	-	0.3989	39.89%
OATP1B3 inhibitior	+	0.9226	92.26%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9072	90.72%
P-glycoprotein inhibitior	-	0.8381	83.81%
P-glycoprotein substrate	-	0.9362	93.62%
CYP3A4 substrate	-	0.6470	64.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7530	75.30%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.7037	70.37%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.5924	59.24%
CYP2C8 inhibition	+	0.9817	98.17%
CYP inhibitory promiscuity	-	0.8459	84.59%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.6571	65.71%
Carcinogenicity (trinary)	Non-required	0.6124	61.24%
Eye corrosion	-	0.9953	99.53%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.8386	83.86%
Skin corrosion	-	0.9726	97.26%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4598	45.98%
Micronuclear	+	0.7174	71.74%
Hepatotoxicity	-	0.5900	59.00%
skin sensitisation	-	0.6857	68.57%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.7780	77.80%
Acute Oral Toxicity (c)	III	0.7657	76.57%
Estrogen receptor binding	+	0.8943	89.43%
Androgen receptor binding	+	0.5307	53.07%
Thyroid receptor binding	+	0.8461	84.61%
Glucocorticoid receptor binding	+	0.8805	88.05%
Aromatase binding	+	0.7656	76.56%
PPAR gamma	+	0.8762	87.62%
Honey bee toxicity	-	0.8548	85.48%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	0.9732	97.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	400 nM	Kd	via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	707.9 nM; 89.1 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL2061	P19793	Retinoid X receptor alpha	930 nM	Kd	via Super-PRED
CHEMBL1860	P10827	Thyroid hormone receptor alpha	19 nM	EC50	via Super-PRED
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	5.6 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.80%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.10%	91.11%
CHEMBL3060	Q9Y345	Glycine transporter 2	94.74%	99.17%
CHEMBL2581	P07339	Cathepsin D	93.25%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.35%	94.45%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.03%	96.95%
CHEMBL3864	Q06124	Protein-tyrosine phosphatase 2C	86.76%	94.42%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	84.56%	97.88%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.08%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.30%	95.50%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.17%	95.89%
CHEMBL1255126	O15151	Protein Mdm4	81.02%	90.20%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.88%	86.33%
CHEMBL3401	O75469	Pregnane X receptor	80.18%	94.73%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 5819
• NPASS: NPC197239
• ChEMBL: CHEMBL1624
• LOTUS: LTS0233381
• wikiData: Q773449