Liothyronine

Details

• Internal ID: 376246e0-a5de-444a-b8b7-ebaf63b03a19
• 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-iodophenoxy)-3,5-diiodophenyl]propanoic acid
• InChI: InChI=1S/C15H12I3NO4/c16-9-6-8(1-2-13(9)20)23-14-10(17)3-7(4-11(14)18)5-12(19)15(21)22/h1-4,6,12,20H,5,19H2,(H,21,22)/t12-/m0/s1
• InChI Key: AUYYCJSJGJYCDS-LBPRGKRZSA-N
• Popularity: 41,786 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂I₃NO₄
• Molecular Weight: 650.97 g/mol
• Exact Mass: 650.7901 g/mol
• Topological Polar Surface Area (TPSA): 92.80 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 3.95
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• triiodothyronine
• 3,3',5-Triiodo-L-thyronine
• 6893-02-3
• Tresitope
• Liothyronin
• 3,5,3'-triiodothyronine
• triothyrone
• Liothyroninum
• Liotironina
• Lyothyronine
• 3,5,3'-Triiodo-L-thyronine
• T3
• L-Liothyronine
• O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine
• Cyronine
• L-T3
• 3,3',5-Triiodothyronine
• 3,5,3'TRIIODOTHYRONINE
• L-3,5,3'-Triiodothyronine
• L-3,3',5-TriioDOThyronine
• Rathyronine, (s)-
• (2S)-2-amino-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]propanoic acid
• (S)-2-amino-3-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)propanoic acid
• CHEBI:18258
• Liotironina [INN-Spanish]
• Triiodo-L-thyronine
• L-Tyrosine, O-(4-hydroxy-3-iodophenyl)-3,5-diiodo-
• Liothyronine (GMP)
• Liothyronine (INN)
• 06LU7C9H1V
• DTXSID8023216
• 4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenylalanine
• HSDB 3110
• EINECS 229-999-3
• NSC 80203
• NSC-80203
• Thyronine, 3,3',5-triiodo-, L-
• Liothyroninum [INN-Latin]
• BRN 2710227
• CHEMBL1544
• UNII-06LU7C9H1V
• 4-(3-Iodo-4-hydroxyphenoxy)-3,5-diiodophenylalanine
• 4-(4-hydroxy-3-iodophenoxy)-3,5-diiodo-L-phenylalanine
• DTXCID403216
• 3,5,3'-triiodothyronine, l-
• L-triiodothyronine
• Alanine, 3-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)-, L-
• LIOTHYRONINE [INN]
• Liothyroninum (INN-Latin)
• Liotironina (INN-Spanish)
• O-(4-Hydroxy-3-iodophenyl-3,5-diiodo-L-tyrosine
• T-3
• LIOTHYRONINE (USP-RS)
• LIOTHYRONINE [USP-RS]
• T3 (amino acid)
• LIOTHYRONINE (USP IMPURITY)
• LIOTHYRONINE [USP IMPURITY]
• Liothyronine [INN:BAN]
• Euthroid-1
• Euthroid-2
• Euthroid-3
• Thyrolar-1
• Thyrolar-2
• Thyrolar-3
• (+)-Triiodothyronine
• CAS-6893-02-3
• Euthroid-0.5
• Thyrolar-0.5
• T3 (VAN)
• Thyrolar-0.25
• Triiodothyronine, l-
• 3,5,3'-Tri-iodo-L-thyronine
• Triiodothyronine (T3)
• SR-05000000455
• 3,3',5-Triiodo-D-thyronine
• NSC80203
• NSC-46046
• Therapeutic T3
• 3,3',5-Triiodothyronine, L-
• 4-(3-iodo-4-hydroxy-phenoxy)-3,5-diiodophenylalanine
• 1xzx
• (2S)-2-AMINO-3-(4-(4-HYDROXY-3-IODOPHENOXY)-3,5-DIIODOPHENYL)PROPANOIC ACID
• Prestwick_135
• MFCD00002593
• Spectrum_001445
• L-3-(4-(4-Hydroxy-3-iodophenoxy)-3,5-diiodophenyl)alanine
• Triiodothyronine;3,3',5-Triiodo-L-thyronine;T3
• THYROLAR-5
• Prestwick0_000853
• Prestwick1_000853
• Prestwick2_000853
• Prestwick3_000853
• Spectrum2_001984
• Spectrum3_001887
• Spectrum4_000326
• Spectrum5_001793
• LIOTHYRONINE [MI]
• Epitope ID:131324
• LIOTHYRONINE [HSDB]
• SCHEMBL8300
• NCIStruc1_000449
• LIOTHYRONINE [VANDF]
• REGID_for_CID_5920
• BSPBio_000865
• BSPBio_003394
• KBioGR_000671
• KBioGR_002568
• KBioSS_001925
• KBioSS_002577
• MLS000028458
• 3,5,3'-triodo-L-thyronine
• LIOTHYRONINE [WHO-DD]
• SPBio_002167
• SPBio_002786
• BPBio1_000953
• GTPL2634
• HY-A0070AG
• L-3,3',5-triiodo-Thyronine
• BCBcMAP01_000192
• BDBM18860
• HY-A0070A
• KBio2_001925
• KBio2_002568
• KBio2_004493
• KBio2_005136
• KBio2_007061
• KBio2_007704
• KBio3_002897
• KBio3_003046
• H03AA02
• cMAP_000088
• HMS1570L07
• HMS2097L07
• HMS2235A22
• HMS3714L07
• TRIIODOTHYRONINE (T3 OR LIOTHYRONINE, ACTIVE) (6-11%)
• Tox21_110029
• Tox21_301943
• HB7470
• NCGC00013556
• s5726
• 3,5,3'-triiodo-L-thyronine (T3)
• (S)-2-Amino-3-(4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl)propanoicacid
• AKOS016003266
• 3,3',5-Triiodo-L-thyronine, 95%
• AM83597
• CCG-220853
• CS-4141
• DB00279
• L-3,3',5-Triiodothyronine, free acid
• SMP1_000179
• NCGC00013556-01
• NCGC00013556-02
• NCGC00013556-03
• NCGC00013556-04
• NCGC00013556-05
• NCGC00013556-15
• NCGC00096669-01
• NCGC00096669-02
• NCGC00255336-01
• [125I]T3
• AC-31935
• AS-17446
• SMR000058402
• SBI-0206718.P001
• CS-0622788
• T0453
• C02465
• D08128
• EN300-123970
• A836290
• Q327362
• SR-01000003143
• SR-01000003143-4
• SR-05000000455-2
• SR-05000000455-3
• 3,3 inverted exclamation mark ,5-Triiodo-L-thyronine
• BRD-K89152108-001-03-3
• LEVOTHYROXINE SODIUM IMPURITY A [EP IMPURITY]
• 3,3',5-Triiodo-L-thyronine, >=95% (HPLC), powder
• Z1557400301
• D-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]alanine
• L-3-[4-(4-hydroxy-3-iodophenoxy)-3,5-diiodophenyl]-Alanine
• Liothyronine, United States Pharmacopeia (USP) Reference Standard
• 3,3',5 Triiodothyronine (T3), IRMM(R) certified Reference Material
• O-(4-Hydroxy-3-iodophenyl)-3,5-diiodo-L-tyrosine,labeled with(125i)iodine
• Liothyronine, Pharmaceutical Secondary Standard; Certified Reference Material
• 57164-27-9

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9674	96.74%
Caco-2	-	0.8562	85.62%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.6085	60.85%
OATP2B1 inhibitior	-	0.6223	62.23%
OATP1B1 inhibitior	+	0.8527	85.27%
OATP1B3 inhibitior	+	0.9226	92.26%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8842	88.42%
P-glycoprotein inhibitior	-	0.9166	91.66%
P-glycoprotein substrate	-	0.9459	94.59%
CYP3A4 substrate	-	0.6882	68.82%
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	+	0.9470	94.70%
CYP inhibitory promiscuity	-	0.8459	84.59%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.6571	65.71%
Carcinogenicity (trinary)	Non-required	0.6124	61.24%
Eye corrosion	-	0.9953	99.53%
Eye irritation	-	0.9638	96.38%
Skin irritation	-	0.8386	83.86%
Skin corrosion	-	0.9726	97.26%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5806	58.06%
Micronuclear	+	0.7174	71.74%
Hepatotoxicity	-	0.9601	96.01%
skin sensitisation	-	0.6857	68.57%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.9625	96.25%
Nephrotoxicity	-	0.6194	61.94%
Acute Oral Toxicity (c)	III	0.7657	76.57%
Estrogen receptor binding	+	0.8907	89.07%
Androgen receptor binding	+	0.6497	64.97%
Thyroid receptor binding	+	0.8205	82.05%
Glucocorticoid receptor binding	+	0.8970	89.70%
Aromatase binding	-	0.4916	49.16%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.8520	85.20%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6250	62.50%
Fish aquatic toxicity	+	0.9732	97.32%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5162	Q6W5P4	Neuropeptide S receptor	794.3 nM	Potency	via Super-PRED
CHEMBL235	P37231	Peroxisome proliferator-activated receptor gamma	710 nM	Kd	via Super-PRED
CHEMBL204	P00734	Thrombin	1.2 nM	EC50	via Super-PRED
CHEMBL1860	P10827	Thyroid hormone receptor alpha	0.24 nM; 0.058 nM	IC50; Kd	via Super-PRED; via Super-PRED
CHEMBL1947	P10828	Thyroid hormone receptor beta-1	0.081 nM; 0.103 nM; 0.26 nM	Kd; IC50; IC50	via Super-PRED; via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.55%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.95%	96.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	95.38%	99.17%
CHEMBL1951	P21397	Monoamine oxidase A	92.47%	91.49%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.78%	96.95%
CHEMBL2581	P07339	Cathepsin D	86.98%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.98%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.70%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.50%	94.62%
CHEMBL4208	P20618	Proteasome component C5	84.92%	90.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	84.30%	97.21%
CHEMBL1255126	O15151	Protein Mdm4	80.17%	90.20%
CHEMBL236	P41143	Delta opioid receptor	80.03%	99.35%

Plants that contains it

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Cross-Links

• PubChem: 5920
• LOTUS: LTS0118570
• wikiData: Q327362